Composition

Abstract

The composition includes (i) rebaudioside M, (ii) a glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. Sweetened compositions include the composition and at least one other sweetener, and sweetened consumables contain the composition or the sweetened composition. Methods of making the composition, sweetened compositions, and sweetened consumables are also provided. Methods of using the composition to reduce the amount of sugar present in a sweetened consumable, enhance the sweetness of the sweetened composition and sweetened consumable, and / or modify the characteristics of a sweetened consumable are further provided.

Description

[Technical Field]

[0001] Cross-references to related applications This application is a continuation-in-part application of U.S. application number 16 / 617,687, filed on November 27, 2019, which is a national stage application of international application PCT / EP2018 / 064324 filed on 31 May 2018, claiming priority from U.S. provisional patent application 62 / 514,482, filed on 2 June 2017, and 62 / 549,242, filed on 23 August 2017, all of which are incorporated herein by reference in their entirety.

[0002] Technical field The present invention generally relates to the use of one or more low-potency sweeteners to improve one or more sweetening characteristics of one or more high-intensity sweeteners. Thus, the present invention also relates to compositions comprising a mixture of at least one high-intensity sweetener and at least one low-potency sweetener. The present invention further relates to the use of a combination of at least one high-intensity sweetener and at least one low-potency sweetener as a sweetening modifier when used in combination with at least one other sweetener and / or as a sweetener. The present invention further relates to the use of one or more mogrosides as sweetening enhancers in a sweetened composition and the sweetened composition. The present invention further relates to methods for producing the sweeteners and compositions disclosed herein. [Background technology]

[0003] background Sweetness in edible products, which are products intended to be taken orally either for permanent consumption or temporarily to be spit out, is often a desired characteristic. Traditionally, sweetness has been provided by the addition of one or more sweeteners, particularly low-potency, nutrient-rich sweeteners, such as sugar alcohols like sucrose (table sugar), fructose, glucose, xylose, arabinose, rhamnose, erythritol, xylitol, mannitol, sorbitol, and inositol, as well as sugar syrups like high-fructose corn syrup and corn syrup. These produce a considerable sweetness without any undesirable aftertaste. However, it is desirable to reduce the amount of these sweeteners used in order to lower the calorie value of edible products. Therefore, it is desirable to provide alternative sweeteners that can maintain the same or a similar sweet flavor while reducing the calorie value of edible products.

[0004] High-intensity sweeteners (HIS) are used for this purpose. High-intensity sweeteners, which may be natural or artificial, possess a sweetness that can be hundreds of times greater than that of sucrose, and thus can theoretically replace very large amounts of sugar in a composition. Examples of high-intensity sweeteners include sucralose, saccharin, aspartame, acesulfame potassium (AceK), neotame, advantame, stevioside, rebaudioside A, rebaudioside D, or steviol glycosides, including steviol glycoside mixtures containing rebaudioside A and / or stevioside as the main component. However, these substances generally have the drawback that they may impart undesirable off-tastes to food products, typically bitter, metallic, or licorice flavors, or an undesirable lingering sweetness.

[0005] Sucrose provides a short, intense upfront sweetness without any significant off-notes or aftertaste, and then fades. Rebaudioside M (Reb M or reb M) is used as a sucrose alternative sweetener to reduce the calorie content of food products. Compared to sucrose, Reb M has a delayed, slight upfront sweetness that transitions into an intense sweet impact, followed by a rapid decrease in sweetness and an undesirable, lingering off-note or aftertaste, typically bitter, metallic, or licorice. Reb M also gives a lingering dry and / or astringent mouthfeel.

[0006] Furthermore, while Reb M can impart intense sweetness to food products at lower concentrations compared to sucrose, it also exhibits lower water solubility compared to other natural and artificial sweeteners, typically those used in the food and beverage industry. This lower water solubility of Reb M is a negative characteristic that limits its technical feasibility and industrial-scale use. Therefore, it is desirable to provide alternative and / or improved sweetness-modifying compositions and sweetened compositions that address one or more of these problems. [Overview of the Initiative]

[0007] overview According to the first aspect of the present invention, One or more high-intensity sweeteners selected from the group consisting of steviol glycosides and / or mogrosides; and One or more low-intensity sweeteners selected from the group consisting of cellobiose, psicose, cyclamate, and / or 11-O-mogroside V; A composition that modifies sweetness, comprising The sweetening composition here increases the sweetness of the sweetened composition beyond the sweetness of the sweetening composition alone; and / or Herein, a sweetening-modifying composition is provided in which the ratio of one or more high-intensity sweeteners (one or more) to one or more low-intensity sweeteners (one or more) is in the range of about 2:1 to about 12:1.

[0008] According to a second aspect of the present invention, At least one sweetener present in an amount equivalent to or greater than approximately 1.5% (w / v) sucrose equivalent; and A composition for modifying sweetness according to any aspect or embodiment of the present invention. A composition containing sweetness is provided.

[0009] A third aspect of the present invention is provided, which involves the use of one or more low-potency sweeteners selected from the group consisting of cellobiose, psicose, cyclamate and / or 11-O-mogroside V to improve one or more sweetening characteristics of a sweetened composition comprising one or more high-potency sweeteners selected from the group consisting of steviol glycosides and / or mogrosides, wherein the total concentration of the one or more low-potency sweeteners and one or more high-potency sweeteners used herein has a sweetness of less than 1.5% (w / v) sucrose equivalent.

[0010] A fourth aspect of the present invention relates to a method for enhancing the sweetness of a sweetened composition, comprising: providing a base composition comprising at least one sweetener present in an amount equal to or exceeding the sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent; and adding one or more high-intensity sweeteners selected from the group consisting of steviol glycosides and / or mogrosides and one or more low-intensity sweeteners selected from the group consisting of cellobiose, psicose, cyclamate and / or 11-O-mogroside V, wherein one or more high-intensity sweeteners (one or more) The method is provided wherein the ratio of ) to one or more low-potency sweeteners (one or more) is from about 2:1 to about 12:1; and / or thereafter, one or more high-potency sweeteners (one or more) are added in a total amount equivalent to or greater than about 15 ppm, and optionally equivalent to or less than about 50 ppm, and one or more low-potency sweeteners (one or more) are added in a total amount equivalent to or greater than about 2 ppm, and optionally equivalent to or less than about 12 ppm; and / or thereafter, the total concentration to which one or more high-potency sweeteners (one or more) and one or more low-potency sweeteners (one or more) are added has a sweetness of less than 1.5% (w / v) sucrose equivalent.

[0011] A fifth aspect of the present invention is provided, a method for preparing a sweetness-modifying composition according to any aspect or embodiment of the present invention, the method comprising combining one or more high-intensity sweeteners and one or more low-efficacy sweeteners.

[0012] A sixth aspect of the present invention is provided, which is a method for preparing a sweetened composition according to any aspect or embodiment of the present invention, the method comprising combining a base composition, one or more high-intensity sweeteners, one or more low-intensity sweeteners, and at least one other sweetener.

[0013] A seventh aspect of the present invention is provided, which provides a sweetened composition comprising at least one sweetener present in an amount equivalent to or greater than 1.5% (w / v) sucrose equivalent; and one or more sweeteners selected from mogroside IV, siamenoside, and neomogroside.

[0014] According to an eighth aspect of the present invention, the use of one or more of mogroside IV, siamenoside, and neomogroside is provided to enhance the sweetness of a sweetened composition. Thus, in a further aspect, a method is provided for enhancing the sweetness of a sweetened composition, the method comprising providing a base composition and adding at least one sweetener and one or more sweeteners selected from mogroside IV, siamenoside, and neomogroside.

[0015] A ninth aspect of the present invention is provided, which is a method for preparing a sweetened composition according to any aspect or embodiment of the present invention, the method comprising combining a base composition, one or more sweeteners selected from mogroside IV, siamenoside and neomogroside, and at least one other sweetener.

[0016] According to a tenth aspect of the present invention, a sweetened composition comprising one or more mogrosides is provided. The one or more mogrosides may be present, for example, as a sweetness enhancer and thus in an amount having less than 1.5% (w / v) sucrose equivalent sweetness. The sweetened composition would then further comprise at least one sweetener present in an amount having sweetness equivalent to or greater than 1.5% (w / v) sucrose equivalent.

[0017] According to an eleventh aspect of the present invention, the use of one or more mogrosides is provided to enhance the sweetness of a sweetened composition. Thus, a method is provided for enhancing the sweetness of a sweetened composition, the method comprising providing a base composition and adding at least one sweetener and one or more mogrosides.

[0018] According to a twelfth aspect of the present invention, a method is provided for preparing a sweetened composition according to any aspect or embodiment of the present invention, the method comprising combining a base composition, one or more mogrosides, and at least one other sweetener.

[0019] In any aspect of the present invention, one or more high-intensity sweeteners may include or not include mogroside V, and / or one or more low-intensity sweeteners may include or not include 11-O-mogroside V. In any aspect of the present invention, the ratio of one or more high-intensity sweeteners to one or more low-intensity sweeteners is from about 2:1 to about 12:1. In any aspect of the present invention, the ratio of one or more high-intensity sweeteners to one or more low-intensity sweeteners is from about 5:1 to about 12:1. In any aspect of the present invention, the ratio of one or more high-intensity sweeteners to one or more low-intensity sweeteners may be from about 6:1 to about 10:1.

[0020] In any aspect of the present invention, one or more high-intensity sweeteners may be present in a total amount ranging from about 15 ppm to about 30 ppm, and / or one or more low-intensity sweeteners may be present in a total amount ranging from about 2 ppm to about 10 ppm. In any aspect of the present invention, one or more high-intensity sweeteners may be present in a total amount ranging from about 22 ppm to about 28 ppm, and / or one or more low-intensity sweeteners may be present in a total amount ranging from about 2 ppm to about 5 ppm. In some embodiments of aspects 7 to 12 of the present invention, one or more mogrosides or one or more sweeteners may be present in an amount ranging from about 15 ppm to about 50 ppm. In some embodiments, one or more mogrosides or one or more sweeteners may be present in an amount ranging from about 15 ppm to about 35 ppm.

[0021] In any aspect of the present invention, a combination of one or more high-intensity sweeteners and one or more low-intensity sweeteners may have a sweetness of less than about 1.5% (w / v) sucrose equivalent on its own. In particular, the concentrations of one or more high-intensity sweeteners and one or more low-intensity sweeteners in a sweetened composition may have a sweetness of less than about 1.5% (w / v) sucrose equivalent. In some embodiments of aspects 7 to 12 of the present invention, one or more mogrosides or one or more sweeteners may have a total sweetness of less than about 1.5% (w / v) sucrose equivalent. In some embodiments, one or more sweeteners increase the sweetness of the sweetened composition to a degree exceeding the total sweetness of one or more sweeteners alone.

[0022] In any aspect of the present invention, a combination of one or more high-intensity sweeteners and one or more low-efficacy sweeteners may increase the sweetness of the sweetened composition beyond the sweetness of the combination alone. In any aspect of the present invention, a combination of one or more high-intensity sweeteners and one or more low-efficacy sweeteners may increase the sweetness of the composition to an amount equivalent to or greater than about 1.25% (w / v) sucrose equivalent. In any aspect of the present invention, one or more low-potency sweeteners reduce the lingering sweet flavor of a sweetened composition containing one or more high-potency sweeteners compared to the lingering sweet flavor of a sweetened composition containing one or more low-potency sweeteners in the complete absence of one or more low-potency sweeteners.

[0023] In any aspect of the present invention, one or more low-potency sweeteners reduce the bitter and / or astringent flavor of a sweetened composition containing one or more high-potency sweeteners compared to the bitter and / or astringent flavor of a sweetened composition containing one or more low-potency sweeteners in the complete absence of one or more low-potency sweeteners. One or more of the sweeteners used (for example, all of them) may be natural or synthetic (artificial). One or more of the sweeteners may be produced, for example, by a biological process, an enzymatic process, or a synthetic process.

[0024] According to another exemplary aspect of the present invention, the provided composition comprises (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. The composition may also comprise a sweetening composition or a sweetening-modifying composition. According to one embodiment, the amount of glucosylated steviol glycoside present in the composition is greater than the amount of rebaudioside M present in the composition. According to another exemplary aspect of the present invention, the provided is a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier, wherein the ratio of the glucosylated steviol glycoside to the rebaudioside M in the composition is from 1:1.1 to 1:1.5.

[0025] According to another exemplary aspect of the present invention, the provided is a sweetened composition comprising at least one sweetener and a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. According to one embodiment, the amount of glucosylated steviol glycoside present in the composition is greater than the amount of rebaudioside M present in the composition. According to another exemplary aspect of the present invention, the provided is a sweetened composition comprising at least one sweetener and a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside and (iii) an effective amount of a taste modifier, wherein the ratio of the glucosylated steviol glycoside to the rebaudioside M in the composition is from 1:1.1 to 1:1.5.

[0026] According to another exemplary aspect of the present invention, what is provided is the use of a composition that improves one or more characteristics of a sweetened composition, the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. According to one embodiment, the amount of glucosylated steviol glycoside present in the composition is greater than the amount of rebaudioside M present in the composition. According to one embodiment, the use of a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier is to improve the sweetness characteristics of the sweetened composition.

[0027] According to another exemplary aspect of the present invention, what is provided is the use of a composition that improves one or more characteristics of a sweetened composition, the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier, wherein the ratio of the rebaudioside M to the glucosylated steviol glycoside in the sweetened composition is from 1:1.1 to 1:1.5. According to one embodiment, the use of a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier is to improve the sweetness characteristics of the sweetened composition.

[0028] According to another exemplary aspect of the present invention, the provided method is for enhancing the sweetness of a sweetened composition, the method comprising providing a base composition comprising at least one sweetener present in an amount equal to or exceeding the sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. According to one embodiment, the amount of glucosylated steviol glycoside present in the composition is greater than the amount of rebaudioside M present in the composition.

[0029] According to another exemplary aspect of the present invention, the provided method is for enhancing the sweetness of a sweetened composition, the method comprising providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier, wherein the ratio of the rebaudioside M to the glucosylated steviol glycoside in the composition is between 1:1.1 and 1:1.5.

[0030] According to another exemplary aspect of the present invention, the provided sweetened consumable comprises a food or beverage base composition containing at least one sweetener present in an amount equal to or exceeding its sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, wherein the composition comprises (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. According to one embodiment, the amount of glucosylated steviol glycoside present in the composition is greater than the amount of rebaudioside M present in the composition.

[0031] According to another exemplary aspect of the present invention, the provided sweetened consumable comprises a food or beverage base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, wherein the composition comprises (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier, wherein the ratio of the rebaudioside M to the glucosylated steviol glycoside in the sweetening composition is between 1:1.1 and 1:1.5.

[0032] According to another exemplary aspect of the present invention, the provided method is a method for reducing the amount of sugar in a sweetened composition, the method comprising providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, and adding a composition to the base composition, the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. According to one embodiment, the amount of glucosylated steviol glycoside present in the composition is greater than the amount of rebaudioside M present in the composition.

[0033] According to another exemplary aspect of the present invention, the provided method is a method for reducing the amount of sugar in a sweetened composition, the method comprising providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, and adding a composition to the base composition, the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier, wherein the ratio of the rebaudioside M to the glucosylated steviol glycoside in the composition is between 1:1.1 and 1:1.5.

[0034] According to another exemplary aspect of the present invention, what is provided is a composition comprising (i) rebaudioside M and (ii) an effective amount of a taste modifier. According to another exemplary aspect of the present invention, the provided is a sweetened composition comprising at least one sweetener and (i) rebaudioside M and (ii) an effective amount of a taste modifier.

[0035] According to another exemplary aspect of the present invention, the provided product is a sweetened consumable comprising a food or beverage base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, wherein the composition comprises (i) rebaudioside M and (ii) an effective amount of a taste modifier. According to another exemplary aspect of the present invention, what is provided is the use of a composition that improves one or more characteristics of a sweetened composition, wherein the composition comprises (i) rebaudioside M and (ii) an effective amount of a taste modifier. The use of the composition is to improve the sweetness characteristics of the sweetened composition.

[0036] According to another exemplary aspect of the present invention, the provided is a method for enhancing the sweetness of a sweetened composition, the method comprising providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, the composition comprising (i) rebaudioside M and (ii) an effective amount of a taste modifier.

[0037] According to another exemplary aspect of the present invention, the provided method is a method for reducing the amount of sugar in a sweetened composition, the method comprising providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, and adding a composition to the base composition, the composition comprising (i) rebaudioside M and (ii) an effective amount of a taste modifier. According to another exemplary aspect of the present invention, what is provided is a composition comprising (i) a glucosylated steviol glycoside and (ii) an effective amount of a taste modifier.

[0038] According to another exemplary aspect of the present invention, the provided is a sweetened composition comprising at least one sweetener and a composition comprising (i) a glucosylated steviol glycoside and (ii) an effective amount of a taste modifier. According to another exemplary aspect of the present invention, the provided sweetened consumable comprises a food or beverage base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, wherein the composition comprises (i) a glucosylated steviol glycoside and (ii) an effective amount of a taste modifier.

[0039] According to another exemplary aspect of the present invention, what is provided is the use of a composition that improves one or more characteristics of a sweetened composition, the composition comprising (i) a glucosylated steviol glycoside and (ii) an effective amount of a taste modifier. The use of the composition is to improve the sweetness characteristics of the sweetened composition. According to another exemplary aspect of the present invention, the provided method is for enhancing the sweetness of a sweetened composition, the method comprising providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, the composition comprising (i) a glucosylated steviol glycoside and (ii) an effective amount of a taste modifier.

[0040] According to another exemplary aspect of the present invention, the provided method is a method for reducing the amount of sugar in a sweetened composition, the method comprising providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, and adding a composition to the base composition, the composition comprising (i) a glucosylated steviol glycoside and (ii) an effective amount of a taste modifier.

[0041] Any aspect of the present invention may provide one or more of the following advantages: • Increased sweetness in the composition; • Enhanced sweetness in a composition containing at least one sweetener; • A reduction in the amount of high-calorie sweeteners needed to achieve the desired sweetness; • Improvement of one or more sweetness characteristics to achieve a similar sweet flavor using sugar (sucrose); • To reduce the lingering sweetness (for example, by reducing the length of time the sweet flavor persists and / or by reducing the intensity of the sweet flavor more quickly); • To reduce bitter flavors and / or licorice flavors and / or metallic flavors; - To reduce the perception of dryness and / or astringency in the mouth; • Improving the impact of sweetness (e.g., increasing the maximum intensity of sweet flavor and / or decreasing the duration of the detected sweet flavor) (e.g., reducing lingering sweetness).

[0042] Details, examples, and preferences provided with respect to one or more of the defined aspects of the Invention will be further described herein and will apply equally to all aspects of the Invention. Any combination of the embodiments, examples, and preferences described herein in all its viable variations is covered herein unless otherwise indicated elsewhere herein or expressly refuted elsewhere in the context. [Brief explanation of the drawing]

[0043] Simple description of the drawing [Figure 1] Figure 1 shows the chromatogram of the monk fruit extract (extract 2 in Table 1 below). [Figure 2] Figure 2 shows the chemical structures of mogrosides 1-6; [Figure 3-1] Figure 3 shows the LC-MS analysis of commercial monk fruit extract; [Figure 3-2] Figure 3 shows the LC-MS analysis of commercial monk fruit extract; [Figure 4-1] Figure 4 shows heteronuclear single-quantum coherence-total correlation spectroscopy (HSQC-TOCSY) (hsqcgpmlph) of iso-mogroside VI at various mixing times (d9). A: 10 ms mixing time. B: 30 ms mixing time. C: 60 ms mixing time. D: 100 ms mixing time. Due to the overlap between H-1 of Glc II and H-6a of Glc III, the HSQC-TOCSY correlation strength of Glc II was not analyzed here. [Figure 4-2]Figure 4 shows heteronuclear single-quantum coherence-total correlation spectroscopy (HSQC-TOCSY) (hsqcgpmlph) of iso-mogroside VI at various mixing times (d9). A: 10 ms mixing time. B: 30 ms mixing time. C: 60 ms mixing time. D: 100 ms mixing time. Due to the overlap between H-1 of Glc II and H-6a of Glc III, the HSQC-TOCSY correlation strength of Glc II was not analyzed here.

[0044] [Figure 5] Figure 5 shows the quantification of the HSQC-TOCSY (hsqcgpmlph) peak intensity of isomogroside VI glucopyranosyl at various mixing times. (*The C-3 and C-5 signals on HSQC-TOCSY overlap at a mixing time of 100 ms. Therefore, the sum of the C-3 and C-5 integrals was used in the bar graph.)

[0045] [Figure 6]Figure 6 shows a strategy for elucidating mogroside glycans (*The number of C-2 to C-6 appearing under a given mixing time may vary slightly when the peak intensity of HSQC-TOCSY is adjusted. The order of linkage can be further determined by observing the increase in the intensity of C-2 to C-6 in experiments with various mixing times.**Natural glycosylation on C-3 of mogroside glucopyranosyl does not exist to date. C-3 glycosylation on glucopyranosyl causes a downshift from δ76 to δ81 and can be easily determined by HSQC-TOCSY experiments). The sequence of steps in Figure 6 can be outlined below: In step 1, heteronuclear multi-bond correlation spectroscopy (HMBC) was used to determine the anormeric C-1 and H-1 of the sugar. We begin with linking the sugar to the aglycone. In step 2, HSQC-TOCSY was used with a mixing time of 100 ms to determine all groups C-2 to C-6. HSQC-COSY or HSQC-TOCSY (d9=10 ms) to assign C-2. HSQC-TOCSY (d9=30 ms) to assign C-3. HSQC-TOCSY (d9=60 ms) to assign C-4. HSQC-TOCSY (d9=100 ms) to assign C-5 and C-6. In step 3, if a C-2 downshift from approximately δ75 to approximately δ81, a C-4 downshift from approximately δ71 to approximately δ81, or a C-6 downshift from approximately δ62 to approximately δ69 is observed, HMBC is checked for glycosylation at these positions. **If a C-2 downshift from approximately δ75 to approximately δ81, a C-4 downshift from approximately δ71 to approximately δ81, or a C-6 downshift from approximately δ62 to approximately δ69 is observed, confirm HMBC for glycosylation at these positions.**

[0046] [Figure 7] Figure 7 shows the chemical structure of iso-mogroside VI, which has the chemical formula C66H112O34 and an exact mass of 1448.70. This chemical structure is designated by formula I; and [Figure 8]Figure 8 shows the chemical structure of 11-epi-mogroside V, which has the chemical formula C60H102O29 and an exact mass of 1286.65. This chemical structure is designated by formula II.

[0047] Detailed description The present invention is based on the surprising finding that a combination of one or more high-intensity sweeteners (e.g., mogroside V) and one or more low-intensity sweeteners (e.g., 11-O-mogroside V) can synergistically interact with at least one other sweetener (e.g., sucrose) to obtain a composition having a sweetness greater than the sum of the individual sweeteners' sweetnesses. The present invention is further based on the surprising finding that one or more low-intensity sweeteners will offset one or more negative sweetness characteristics of one or more high-intensity sweeteners. For example, a combination of one or more high-intensity sweeteners (e.g., mogroside V) and one or more low-intensity sweeteners (e.g., 11-O-mogroside V) would provide improved sweetness characteristics in a sweetened composition (i.e., a composition containing at least one other sweetener, such as sucrose, in an amount exceeding its sweetness perception threshold and / or equivalent to or greater than about 1.5% (w / v) sucrose equivalents) compared to using one or more high-intensity sweeteners alone. Thus, for example, the sweetness characteristics may be closer to those of sucrose.

[0048] Accordingly, various compositions are provided herein that include sweetened compositions comprising at least one sweetener and one or more high-intensity sweeteners and one or more low-intensity sweeteners, in particular in an amount exceeding the sweetness recognition threshold and / or an amount equivalent to or greater than about 1.5% (w / v) sucrose equivalent, as disclosed herein. Sweetened compositions may also be referred to as edible compositions. Various uses of one or more high-intensity sweeteners and one or more low-intensity sweeteners as disclosed herein, and methods for preparing the various compositions disclosed herein, are also provided herein.

[0049] The present invention is further based on the surprising finding that mogrosides, such as mogroside IV, siamenoside, and neomogroside, can act as sweetness enhancers (i.e., they can increase the sweetness of a composition that has been sweetened beyond the sweetness of the sweetness enhancer alone). Therefore, various compositions containing one or more of mogroside IV, siamenoside, and neomogroside, in particular sweetened compositions, are provided herein.

[0050] composition Various compositions comprising at least one high-intensity sweetener and at least one low-intensity sweetener are provided herein. Compositions comprising one or more mogrosides, for example, one or more of mogroside IV, siamenoside, and neomogroside are also provided herein. In some embodiments, the compositions are edible compositions.

[0051] In one embodiment, a sweetness-modifying composition is provided which comprises, or comprises, at least one high-intensity sweetener selected from the group consisting of steviol glycosides and / or mogrosides and at least one low-efficacy sweetener selected from the group consisting of cellobiose, psicose, cyclamate and / or 11-O-mogroside V. In one embodiment, the sweetness-modifying composition comprises, or comprises, one high-intensity sweetener and one low-efficacy sweetener. The sweetness-modifying composition may be, for example, a concentrate, which is diluted in a sweetened (e.g., edible) composition to impart a desired sweetness to the edible composition. The term “sweetened composition” means a composition which comprises at least one sweetener present in an amount exceeding its sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent.

[0052] In one embodiment, a sweetened composition (e.g., an edible composition) is provided that contains one or more mogrosides, for example, one or more of mogroside IV, siamenoside, and neomogroside. In another embodiment, a sweetened composition (e.g., an edible composition) is provided that contains at least one high-intensity sweetener and at least one low-efficacy sweetener. The combination of high-intensity sweeteners (one or more) and low-efficacy sweeteners (one or more) may be referred to as a sweetening composition. One or more mogrosides, for example, one or more of mogroside IV, siamenoside, and neomogroside, may also be referred to herein as a sweetening composition. In one embodiment, a sweetened composition is provided which comprises, or comprises, a sweetening-modifying composition, at least one sweetener present in an amount exceeding the sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, as well as at least one high-intensity sweetener and at least one low-efficacy sweetener. The sweetened composition may, for example, be an edible composition.

[0053] When used particularly in reference to sweetening compositions, the term “enhancing” refers to the effect of a sweetening composition synergistically imparting sweetness when used in combination with at least one other sweetener. A sweetening composition increases the sweetness of a composition to which it has been sweetened beyond the sweetness of the sweetening composition alone. In other words, the sweetness of a composition containing at least one sweetener and at least one sweetening composition is greater than the sum of the sweetness of all the sweeteners in the composition. The sweetening compositions described herein are used in (e.g., edible) compositions to which sweetness has been imparted at an amount that does not have detectable sweetness or flavor that is perceived as sweet (below its sweetness perception threshold). Typically, sweetening compositions with a sweetness of less than 1.5% (w / v) sucrose equivalent are accepted by FEMA (Federal Food Flavor Manufacturers Association) as “essentially unsweetened.” Sweetening modifiers may also be referred to as sweetness enhancers.

[0054] A sweetened composition comprising a sweetening composition as disclosed herein and at least one sweetener in an amount exceeding the sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent may have a sweetness equivalent to or greater than about 1.0% (w / v) sucrose equivalent than the sweetness of the sweetened composition in the absence of the sweetening composition. For example, a sweetened composition may have a sweetness equivalent to or greater than about 1.1% (w / v), or equivalent to or greater than about 1.15% (w / v), or equivalent to or greater than about 1.2% (w / v), or equivalent to or greater than about 1.25% (w / v) sucrose equivalent than the sweetness of the sweetened composition in the absence of the sweetening composition. In other words, a sweetening composition may increase the sweetness of a composition that has been sweetened by an amount equivalent to or greater than approximately 1% (w / v), or equivalent to or greater than approximately 1.1% (w / v), or equivalent to or greater than approximately 1.15% (w / v), or equivalent to or greater than approximately 1.2% (w / v), or equivalent to or greater than approximately 1.25% (w / v) sucrose equivalent. A comparative composition is identical to the sweetening composition except that it does not include the sweetening composition.

[0055] The term "sucrose equivalent" refers to the sweetness equivalent of a composition containing at least one non-sucrose sweetener relative to a reference sucrose solution. Typically, a flavor panelist is trained to detect the sweetness of a reference sucrose solution containing 1% to 15% sucrose (w / v). Other non-sucrose sweeteners are then tasted in a series of dilutions to determine the concentration of non-sucrose sweeteners that are as sweet as (i.e., isosweet) a given sucrose reference. The term "isosweet" refers to a composition having equivalent sweetness. Typically, the sweetness of a given composition is measured relative to a sucrose solution. “A Systematic Study of Concentration-Response Relationships of Sweeteners,” GE DuBois, DE Walters, SS Schiffman, ZS Warwick, BJ Booth, SD Pecore, K. Gibes, BT Carr, and LM Brands, in Sweeteners: Discovery, Molecular Design and Chemoreception, DE Walters, FT Orthoefer, and GE DuBois, Eds., American Chemical Society, Washington, DC (1991), pp 261-276.

[0056] A combination of one or more high-intensity sweeteners and one or more low-efficacy sweeteners (one or more) (for example, a sweetness-modifying composition) may have a sweetness of, for example, less than about 1.5% (w / v) sucrose equivalent. For example, a combination of one or more high-intensity sweeteners and one or more low-efficacy sweeteners (for example, a sweetness-modifying composition) may have a sweetness equivalent to or less than about 1.45% (w / v) sucrose equivalent, or equivalent to or less than about 1.4% (w / v) sucrose equivalent, or equivalent to or less than about 1.35% (w / v) sucrose equivalent, or equivalent to or less than about 1.3% (w / v) sucrose equivalent. For example, a combination of one or more high-intensity sweeteners and one or more low-efficacy sweeteners (e.g., a sweetness-modifying composition) may have a sweetness equivalent to or greater than approximately 1% (w / v) sucrose equivalent, or equivalent to or greater than approximately 1.1% (w / v) sucrose equivalent, or equivalent to or greater than approximately 1.15% (w / v) sucrose equivalent, or equivalent to or greater than approximately 1.2% (w / v) sucrose equivalent, or equivalent to or greater than approximately 1.25% (w / v) sucrose equivalent, or equivalent to or greater than approximately 1.3% (w / v) sucrose equivalent.

[0057] One or more mogrosides, for example, one or more sweeteners selected from mogroside IV, siamenoside, and neomogroside, may have a sweetness of, for example, less than about 1.5% (w / v) sucrose equivalent. For example, one or more mogrosides, for example, one or more sweeteners selected from mogroside IV, siamenoside, and neomogroside, may have a sweetness equivalent to or less than about 1.45% (w / v) sucrose equivalent, or equivalent to or less than about 1.4% (w / v) sucrose equivalent, or equivalent to or less than about 1.35% (w / v) sucrose equivalent, or equivalent to or less than about 1.3% (w / v) sucrose equivalent. For example, one or more mogrosides, such as one or more sweeteners selected from mogroside IV, siamenoside, and neomogroside, may have a sweetness equivalent to or greater than approximately 1% (w / v) sucrose equivalent, or approximately 1.1% (w / v) sucrose equivalent, or approximately 1.15% (w / v) sucrose equivalent, or approximately 1.2% (w / v) sucrose equivalent, or approximately 1.25% (w / v) sucrose equivalent, or approximately 1.3% (w / v) sucrose equivalent, or approximately 1.3% (w / v) sucrose equivalent.

[0058] Each of the sweeteners and sweeteners used in the compositions disclosed herein may be natural or synthetic (artificial) sweeteners. Examples of mogrosides that do not exist in nature (i.e., synthetic) are disclosed in WO2017 / 075257, which is incorporated herein by reference. The term “natural sweetener” means a sweetener obtained from nature, which includes mixtures that may be enzymatically treated (e.g., glycosylated) to form compounds not found in nature (this does not include enzymatically treated and purified compounds). For example, a modified extract having a mogrol glycoside distribution different from (e.g., enhanced) the naturally occurring mogrol glycoside distribution may be classified as natural. For example, a mixture of glucosylated steviol glycosides and / or glucosylated mogrosides may be classified as natural. Each of the sweeteners used in the compositions disclosed herein may be of food origin. "Food-derived" products refer to products prepared under typical cooking conditions, such as using temperatures similar to those used in the cooking method. In some embodiments, both the high-intensity and low-efficacy sweeteners used in the compositions disclosed herein (e.g., the sweetness-modifying compositions disclosed herein) are natural sweeteners. In some embodiments, all sweeteners used in the compositions disclosed herein are natural.

[0059] The sweeteners disclosed herein may be used in pure or purified form, and may be chemically synthesized, produced by biotechnological processes (e.g., fermentation), or isolated from natural sources (e.g., plant sources including, but not limited to, fruits, sugarcane, and sugar beets).

[0060] One or more mogrosides, for example, one or more of mogroside IV, siamenoside, and neomogroside, may have a purity of, for example, at least 80 wt%. For example, one or more mogrosides, for example, one or more of mogroside IV, siamenoside, and neomogroside, may have a purity of at least about 85 wt%, or at least about 90 wt%, or at least about 95 wt%, or at least about 98 wt%, or at least about 99 wt%. For example, one or more mogrosides, for example, one or more of mogroside IV, siamenoside, and neomogroside, may have a purity of up to 100 wt%, or up to 99 wt%.

[0061] The term "high-intensity sweetener" refers to a compound having a sweetness at least 100 times that of sucrose. In one embodiment, a high-intensity sweetener has a sweetness at least about 120 times, or at least about 140 times, or at least about 150 times, or at least about 160 times, or at least about 180 times, or at least about 200 times, or at least about 220 times, or at least about 240 times, or at least about 250 times, or at least about 260 times, or at least about 280 times, or at least about 300 times, or at least about 320 times, or at least about 340 times, or at least about 350 times, or at least about 360 times, or at least about 380 times, or at least about 400 times, or at least about 420 times, or at least about 440 times, or at least about 450 times that of sucrose. High-intensity sweeteners may have a sweetness that is, for example, up to 1000 times that of sucrose. High-intensity sweeteners have a sweetness that is at least 100 times that of sucrose, but in the context of their use in sweetness-modifying compositions as described herein, they will be used in compositions that are sweetened in amounts that are undetectable or not perceived as sweet (amounts that provide sweetness less than 1.5% (w / v) sucrose equivalent, which are accepted by FEMA as "essentially unsweetened").

[0062] One or more high-intensity sweeteners (one or more) may be, for example, one or more steviol glycosides and / or one or more mogrosides. For example, one or more high-intensity sweeteners may be a mixture of steviol glycosides and mogrosides. For example, one or more high-intensity sweeteners may be one or more steviol glycosides. For example, one or more high-intensity sweeteners (one or more) may be one or more mogrosides. In some embodiments, mogrosides may work better than steviol glycosides in terms of sweetness enhancement and off-note reduction (e.g., reducing a lingering sweet aftertaste).

[0063] High-intensity sweeteners may, for example, be one or more steviol glycosides (singular or plural). Examples of steviol glycosides include, for example, stevioside (CAS: 57817-89-7), rebaudioside A (CAS: 58543-16-1), rebaudioside B (CAS: 58543-17-2), rebaudioside C (CAS: 63550-99-2), rebaudioside D (CAS: 63279-13-0), rebaudioside E (CAS: 63279-14-1), rebaudioside F (CAS: 438045-89-7), rebaudioside G (CAS: 127345-21-5), rebaudioside H, and rebaudioside This includes Rebaudioside I (CAS: 1220616-34-1), Rebaudioside J, Rebaudioside K, Rebaudioside L, Rebaudioside M (CAS: 1220616-44-3), Rebaudioside N (CAS: 1220616-46-5), Rebaudioside O (CAS: 1220616-48-7), Dulcoside A (CAS: 64432-06-0), Dulcoside B (CAS: 63550-99-2), Rubusoside (CAS: 64849-39-4), and Naringin Dihydrochalcone (CAS: 18916-17-1).

[0064] The high-intensity sweetener may be, for example, one or more mogrosides. In one embodiment, the high-intensity sweetener may be one or more of the mogrosides listed herein. In one embodiment, the high-intensity sweetener may be one or more of mogroside IV, siamenoside, neomogroside, and mogroside V (including all their isomers). For example, the high-intensity sweetener may be a mixture of mogroside IV, siamenoside, and mogroside V (including all their isomers). One or more mogrosides may be obtained from, for example, monk fruit extract or be readily available.

[0065] The term "low-potency sweetener" refers to a compound that has a sweetness less than 100 times that of sucrose. In one embodiment, a low-potency sweetener has a sweetness up to approximately 95 times, or up to approximately 90 times, or up to approximately 85 times that of sucrose. One or more low-potency sweeteners are selected from one or more of cellobiose, psicose, cyclamate, and / or 11-O-mogroside V (CAS: 126105-11-1). For example, one or more low-intensity sweeteners may be one or more of cellobiose, psicose, and 11-O-mogroside V.

[0066] In one embodiment, one or more high-intensity sweeteners include or are high-intensity mogrosides. In one embodiment, one or more low-intensity sweeteners include or are low-intensity mogrosides. In one embodiment, one or more high-intensity sweeteners include or are high-intensity mogrosides, and one or more low-intensity sweeteners include or are low-intensity mogrosides. In one embodiment, one or more high-intensity sweeteners include or are mogroside V. In one embodiment, one or more low-efficacy sweeteners include or are 11-O-mogroside V. In one embodiment, one or more high-intensity sweeteners include or are mogroside V, and one or more low-efficacy sweeteners include or are 11-O-mogroside V.

[0067] Mogrosides are a group of triterpene glycosides and can be obtained from the fruit of the monk fruit (Siraitia grosvenorii), also known as arhat fruit, longevity fruit, or swingle fruit. Mogrosides make up approximately 1% of the pulp of the fresh fruit. Through extraction, extracts in powder form containing up to 80% mogrosides can be obtained. Mogroside extracts include globunolin II, globunolin I, 11-O-mogroside II(I), 11-O-mogroside II(II), 11-O-mogroside II(III), mogroside II(I), mogroside II(II), mogroside II(III), 11-dehydroxy-mogroside III, 11-O-mogroside III, mogroside III(I), mogroside III(II), mogroside IV(I) (cyamenoside), mog It contains mogroside IV(II), mogroside IV(III), mogroside IV(IV), deoxymogroside V(I), deoxymogroside V(II), 11-O-mogroside V(I), mogroside V isomers, mogroside V, iso-mogroside V, 7-O-mogroside V, 11-O-mogroside VI, mogroside VI(I), mogroside VI(II), mogroside VI(III) (neomogroside), and mogroside VI(IV). The exact amount of mogroside V will vary depending on the maturation of the fruit and / or the extraction process used.

[0068] Mogrosides (singular or plural) include both naturally occurring and non-naturally occurring mogrosides. Examples of mogrosides include, for example, globunolin II, globunolin I, 11-O-mogroside II(I), 11-O-mogroside II(II), 11-O-mogroside II(III), mogroside II(I), mogroside II(II), mogroside II(III), 11-dehydroxy-mogroside III, 11-O-mogroside III, mogroside III(I), mogroside III(II), mogroside IIIe, mogroside IIIx, and mogroside IV(I). This includes (siamenoside), mogroside IV(II), mogroside IV(III), mogroside IV(IV), deoxymogroside V(I), deoxymogroside V(II), 11-O-mogroside V(I), mogroside V isomers, mogroside V, iso-mogroside V, 7-O-mogroside V, 11-O-mogroside VI, mogroside VI(I), mogroside VI(II), mogroside VI(III) (neomogroside), and mogroside VI(IV). Mogrosides (singular or plural) may be obtained or available, for example, from monk fruit extract.

[0069] Mogroside V (CAS: 88901-36-4) is a glycoside of cucurbitan derivatives, with chemical formula C 60 H 102 O 29 It has the chemical structure shown below. Mogroside V can be found in certain plant extracts, such as extracts from the fruit of Siraitia grosvenorii. Pure mogroside V has been found to be at least 400 times sweeter than sucrose. [ka]

[0070] Siamenoside (CAS: 126105-12-2) is a cucurbitan found in the fruit of Siraitia grosvenorii and has the following chemical structure. [ka]

[0071] Mogroside IV (CAS: 89590-95-4) is a triterpene heteroside found in the fruit of Siraitia grosvenorii and has the following chemical structure. [ka]

[0072] Neomogroside (CAS: 189307-15-1) is a cucurbitan glycoside also found in the fruits of Siraitia grosvenorii, and has the following chemical structure. [ka]

[0073] 11-O-Mogroside V (CAS: 126105-11-1) is derived from mogroside V and has the following chemical structure. It is also found in plant extracts, such as extracts from the fruit of Siraitia grosvenorii. 11-O-Mogroside V has been found to have a sweetness approximately 84 times that of sucrose. [ka]

[0074] The ratio of one or more high-intensity sweeteners to one or more low-intensity sweeteners is equivalent to or greater than approximately 2:1. For example, the ratio of one or more high-intensity sweeteners to one or more low-intensity sweeteners may be equivalent to or greater than approximately 2.5:1, or equivalent to or greater than approximately 3:1, or equivalent to or greater than approximately 3.5:1, or equivalent to or greater than approximately 4:1, or equivalent to or greater than approximately 4.5:1, or equivalent to or greater than approximately 5:1, or equivalent to or greater than approximately 5.5:1, or equivalent to or greater than approximately 6:1, or equivalent to or greater than approximately 6.5:1, or equivalent to or greater than approximately 7:1, or equivalent to or greater than approximately 7.5:1, or equivalent to or greater than approximately 8:1. The ratio of high-intensity sweeteners to low-efficacy sweeteners is equivalent to or less than approximately 12:1. For example, the ratio of one or more high-intensity sweeteners to one or more low-efficacy sweeteners may be equivalent to or less than approximately 11.5:1, or equivalent to or less than approximately 11:1, or equivalent to or less than approximately 10.5:1, or equivalent to or less than approximately 10:1, or equivalent to or less than approximately 9.5:1, or equivalent to or less than approximately 9:1, or equivalent to or less than approximately 8.5:1. For example, the ratio of one or more high-intensity sweeteners to one or more low-intensity sweeteners may range from approximately 5:1 to approximately 11:1, or from approximately 6:1 to approximately 10:1, or from approximately 6.5:1 to approximately 9.5:1, or from approximately 7:1 to approximately 9:1, or from approximately 7.5:1 to approximately 8.5:1.

[0075] In one embodiment, the ratio of one or more high-intensity sweeteners to one or more low-intensity sweeteners is approximately 2:1 to approximately 12:1, or approximately 4:1 to approximately 12:1, or approximately 5:1 to approximately 12:1, or approximately 6:1 to approximately 10:1, or approximately 7:1 to approximately 9:1. The ratio may be by weight or by volume. The ratio applies only to high-intensity and low-intensity sweeteners and low-intensity sweeteners used in a sweetened composition (amounts below the sweetness recognition threshold or amounts less than 1.5% (w / v) sucrose equivalent).

[0076] One or more high-intensity sweeteners may be present in the composition in a total amount equivalent to or greater than approximately 15 ppm. For example, one or more high-intensity sweeteners may be present in the composition in a total amount equivalent to or greater than approximately 16 ppm, or equivalent to or greater than approximately 17 ppm, or equivalent to or greater than approximately 18 ppm, or equivalent to or greater than approximately 19 ppm, or equivalent to or greater than approximately 20 ppm, or equivalent to or greater than approximately 21 ppm, or equivalent to or greater than approximately 22 ppm, or equivalent to or greater than approximately 23 ppm, or equivalent to or greater than approximately 24 ppm, or equivalent to or greater than approximately 25 ppm. For example, one or more high-intensity sweeteners may be present in the composition in a total amount equivalent to or less than approximately 50 ppm, or approximately 48 ppm, or approximately 46 ppm, or approximately 45 ppm, or approximately 44 ppm, or approximately 42 ppm, or approximately 40 ppm, or approximately 38 ppm, or approximately 36 ppm, or approximately 35 ppm, or approximately 34 ppm, or approximately 32 ppm, or approximately 30 ppm. For example, one or more high-intensity sweeteners may be present in the composition in a total amount ranging from approximately 15 ppm to approximately 50 ppm, or from approximately 15 ppm to approximately 45 ppm, or from approximately 15 ppm to approximately 40 ppm, or from approximately 15 ppm to approximately 35 ppm, or from approximately 15 ppm to approximately 30 ppm.For example, one or more high-intensity sweeteners may be present in the composition in a total amount ranging from about 15 ppm to about 30 ppm, or from about 20 ppm to about 30 ppm, or from about 22 ppm to about 28 ppm, or from about 23 ppm to about 27 ppm, or from about 24 ppm to about 26 ppm. For example, one or more high-intensity sweeteners may be present in the composition in a total amount of about 20 ppm or about 25 ppm. The composition may be a sweetened composition containing, for example, at least one sweetener in an amount that exceeds its sweetness recognition threshold and / or has a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent.

[0077] One or more low-potency sweeteners may be present in the composition in a total amount equivalent to or greater than approximately 2 ppm. For example, one or more low-potency sweeteners may be present in the composition in a total amount equivalent to or greater than approximately 3 ppm. For example, one or more low-potency sweeteners may be present in the composition in a total amount equivalent to or less than approximately 12 ppm, or equivalent to or less than approximately 11 ppm, or equivalent to or less than approximately 10 ppm, or equivalent to or less than approximately 9 ppm, or equivalent to or less than approximately 8 ppm, or equivalent to or less than approximately 7 ppm, or equivalent to or less than approximately 6 ppm, or equivalent to or less than approximately 5 ppm. For example, one or more low-potency sweeteners may be present in the composition in a total amount ranging from about 2 ppm to about 12 ppm, or from about 2 ppm to about 10 ppm, or from about 2 ppm to about 5 ppm, for example, in a total amount of about 3 ppm. The composition may also contain at least one sweetener other than, for example, a combination of high-potency sweeteners and low-potency sweeteners (e.g., sweetness-modifying compositions) as disclosed herein.

[0078] The concentration range may be particularly suitable for liquid compositions, such as beverages or compositions that do not contain any proteins or fats. In compositions having a base such as milk and yogurt, or other compositions that do not contain proteins or fats, one or more high-intensity sweeteners and one or more low-efficacy sweeteners may be used at higher concentrations. For example, concentrations about 1.5 times higher than those used in liquid compositions or compositions that do not contain any proteins or fats may be used. For example, concentrations about 1.5 to 3 times higher than those used in liquid compositions or compositions that do not contain any proteins or fats may be used.

[0079] Therefore, for example, one or more high-intensity sweeteners may be present in a composition (e.g., a composition having a base such as milk and yogurt, or other compositions containing protein and / or fat) in a total amount ranging from about 20 ppm to about 75 ppm, for example, a total amount ranging from about 22 ppm to about 74 ppm, or a total amount ranging from about 24 ppm to about 72 ppm, or a total amount ranging from about 25 ppm to about 70 ppm, or a total amount ranging from about 26 ppm to about 68 ppm, or a total amount ranging from about 28 ppm to about 66 ppm, or a total amount ranging from about 30 ppm to about 65 ppm, or a total amount ranging from about 30 ppm to about 55 ppm, or a total amount ranging from about 30 ppm to about 50 ppm, or a total amount ranging from about 30 ppm to about 45 ppm.

[0080] Therefore, for example, one or more low-potency sweeteners may be present in a composition (e.g., a composition having a base such as milk and yogurt, or other compositions containing protein and / or fat) in a total amount ranging from about 3 ppm to about 20 ppm, or from about 4 ppm to about 18 ppm, or from about 4 ppm to about 16 ppm, or from about 5 ppm to about 15 ppm, or from about 6 ppm to about 15 ppm.

[0081] In one embodiment, a sweetened composition comprises a sweetening composition consisting of at least one sweetener in an amount having a sweetness exceeding its sweetness recognition threshold and / or greater than about 1.5% (w / v) sucrose equivalent, one or more high-intensity sweeteners as specified herein in an amount of 15 ppm to about 50 ppm, and one or more low-efficacy sweeteners as specified herein in an amount of 2 ppm to 12 ppm. In one embodiment, an edible composition comprises a sweetening composition consisting of at least one sweetener, one or more high-intensity sweeteners as specified herein in an amount of 15 ppm to about 30 ppm, and one or more low-efficacy sweeteners as specified herein in an amount of 2 ppm to 10 ppm. In one embodiment, the edible composition comprises a sweetening composition comprising at least one sweetener and one or more high-intensity sweeteners as specified herein in an amount of 20 ppm to about 30 ppm and one or more low-efficacy sweeteners as specified herein in an amount of 2 ppm to 10 ppm. In one embodiment, the edible composition comprises a sweetening composition comprising at least one sweetener and one or more high-intensity sweeteners as specified herein in an amount of 22 ppm to about 28 ppm and one or more low-efficacy sweeteners as specified herein in an amount of 2 ppm to 5 ppm. In one embodiment, the high-intensity sweetener is mogroside V. In one embodiment, the low-efficacy sweetener is 11-O-mogroside V.

[0082] One or more mogrosides, for example, one or more of mogroside IV, siamenoside, and neomogroside, may be present in a sweetened composition in a total amount equivalent to or greater than, for example, about 15 ppm. For example, one or more mogrosides, such as mogroside IV, siamenoside, and neomogroside, may be present in a sweetened composition in an amount equivalent to or greater than approximately 16 ppm, or equivalent to or greater than approximately 17 ppm, or equivalent to or greater than approximately 18 ppm, or equivalent to or greater than approximately 19 ppm, or equivalent to or greater than approximately 20 ppm, or equivalent to or greater than approximately 21 ppm, or equivalent to or greater than approximately 22 ppm, or equivalent to or greater than approximately 23 ppm, or equivalent to or greater than approximately 24 ppm, or equivalent to or greater than approximately 25 ppm. For example, one or more mogrosides, such as mogroside IV, siamenoside, and neomogroside, may be present in a sweetened composition in a total amount equivalent to or less than about 50 ppm, for example, a total amount equivalent to or less than about 45 ppm, for example, a total amount equivalent to or less than about 40 ppm, for example, a total amount equivalent to or less than about 35 ppm. For example, one or more mogrosides, such as mogroside IV, siamenoside, and neomogroside, may be present in a sweetened composition in a total amount ranging from about 15 ppm to about 50 ppm, or from about 15 ppm to about 45 ppm, or from about 15 ppm to about 40 ppm, or from about 15 ppm to about 35 ppm, or from about 20 ppm to about 35 ppm, or from about 20 ppm to about 30 ppm.

[0083] The term "ppm" refers to one millionth of a compound by weight (singular or plural), for example, the weight (in milligrams) (i.e., mg / Kg) of such compound per kilogram of a product containing mogroside V, or the weight (in milligrams) (i.e., mg / L) of such compound per liter of a product containing mogroside V (e.g., the oral consumables / foodstuffs of this disclosure), or one millionth of a compound by volume (singular or plural), for example, the volume (in milliliters) (i.e., ml / L) of such compound per liter of a product containing a compound such as mogroside V.

[0084] The sweetening compositions described herein may, for example, include high-intensity and low-intensity sweeteners at higher concentrations, which are then diluted in the sweetened composition to obtain the concentrations described herein. A sweetened composition contains at least one sweetener in an amount equivalent to or greater than its sweetness threshold, and / or having a sweetness equivalent to or greater than approximately 1.5% (w / v) sucrose equivalent. The term “sweetness threshold” refers to the lowest known concentration of a compound that can be perceived as sweet by human taste. A sweetness equivalent to or greater than approximately 1.5% (w / v) sucrose equivalent is accepted by FEMA as “essentially sweet.”

[0085] At least one sweetener may be nutritious or non-nutritious. Nutrient sweeteners add calories to foods containing them, while non-nutritious sweeteners are very low in calories or contain no calories at all. In contrast to non-nutritious sweeteners that contain less than 2% of the calories by sugar equivalent, aspartame, the only approved nutritious high-intensity sweetener, contains more than 2% of the calories by sugar equivalent.

[0086] At least one sweetener may be selected from, for example, one or more sugar alcohols such as sucrose, fructose, glucose, xylose, arabinose, rhamnose, tagatose, allulose, trehalose, isomaltulose, acesulfame potassium (AceK), aspartame, steviol glycoside(s), sucralose, high-fructose corn syrup, starch syrup, saccharin, sucralose, neotame, advantame, monk fruit extract, neohesperidin, dihydrochalcone, naringin dihydrochalcone, neohesperidin dihydrochalcone, rubusoside, rebaudioside A, stevioside, stevia, trilobatin, and erythritol, xylitol, mannitol, sorbitol, and inositol. Examples of sweeteners that may be used in sweetened compositions are disclosed, for example, in WO2016 / 038617, which is incorporated herein by reference. At least one sweetener may be selected from, for example, one or more of sucrose, high-fructose corn syrup, acesulfame potassium (AceK), aspartame, steviol glycosides (singular or plural), and / or sucralose.

[0087] Methods for sweetening consumables using a sufficient amount of sweetener are well known in the art. Depending on the consumable, the amount of sweetener may be reduced by adding sweetening compositions as disclosed herein. For example, a reduction of about 1° to about 4° or more in Brix value may be achieved.

[0088] At least one other sweetener present in an amount equivalent to or greater than the sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent may be used, for example, in a composition sweetened to an amount equivalent to or greater than about 0.01% (w / v). For example, at least one other sweetener may be used in a composition sweetened to an amount equivalent to or greater than about 0.1% (w / v), or equivalent to or greater than about 0.5% (w / v), or equivalent to or greater than about 1% (w / v), or equivalent to or greater than about 2% (w / v). For example, at least one other sweetener may be used in the food composition in an amount equivalent to or less than about 20% (w / v), or equivalent to or less than about 15% (w / v), or equivalent to or less than about 10% (w / v), or equivalent to or less than about 8% (w / v), or equivalent to or less than about 6% (w / v), or equivalent to or less than about 5% (w / v). At least one other sweetener present in an amount equivalent to or exceeding the sweetness perception threshold, and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, may be used in a composition (e.g., an edible composition) that is sweetened as disclosed herein in an amount equivalent to about 2% (w / v) to about 15% (w / v) sucrose.

[0089] In one embodiment, a sweetening composition comprising mogroside V and 11-O-mogroside V in a ratio ranging from about 2:1 to about 12:1, for example, in a ratio ranging from about 6:1 to about 10:1, is provided herein. This sweetening composition may be used, for example, as a sweetening enhancer or sweetening modifier in an edible composition. The edible composition may contain at least one other sweetener, such as sucrose. Mogroside V may be used in the edible composition in amounts ranging from about 15 ppm to about 30 ppm, or in amounts ranging from about 20 ppm to about 30 ppm (for example, about 20 ppm or about 25 ppm). 11-O-mogroside V may be used in the edible composition in amounts ranging from about 2 ppm to about 12 ppm, or in amounts ranging from about 2 ppm to about 10 ppm (for example, about 8.5 ppm or about 3 ppm). At least one other sweetener may be present in the edible composition in an amount equivalent to, for example, about 2% (w / v) to about 15% (w / v) sucrose.

[0090] In one exemplary embodiment, the composition comprises (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. For the purposes of this specification, the term “taste modifier” means one or more components that improve the sweet flavor profile of a reduced-sugar sweetened composition or sweetened consumable to which it is added. In one exemplary embodiment, without limitation, the taste modifier (iii) of the composition may comprise one or more components in an effective amount (one or more) that masks off-notes related to rebaudioside M in the composition and improves mouthfeel.

[0091] The amount of glucosylated steviol glycoside present in the composition may be greater than the amount of rebaudioside M present in the composition. For example, but not limited to, the ratio of rebaudioside M to glucosylated steviol glycoside present in the composition may be in the range of approximately 1:1 to approximately 1:1.5. The ratio of rebaudioside M to glucosylated steviol glycoside in the composition may be selected from any one of the following ratios: 1:1.1, 1:1.2, 1:1.3, 1:1.4, or 1:1.5. For example, but not limited to, the ratio of rebaudioside M to glucosylated steviol glycoside in the composition is 1:1.2.

[0092] A sweetened composition includes a composition comprising at least one sweetener and (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. The amount of glucosylated steviol glycoside present in the composition may be greater than the amount of rebaudioside M present in the composition. In one exemplary embodiment, without limitation, the taste modifier (iii) of the composition may comprise one or more components in an effective amount (one or more) that masks off-notes related to rebaudioside M in the composition and improves the mouthfeel.

[0093] The sweetened consumable may be prepared using a composition containing (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier, or a sweetened composition containing a composition containing (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier. In one embodiment, the sweetened consumable comprises a food or beverage base composition containing at least one sweetener present in an amount equal to or exceeding its sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, and a composition containing (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier, wherein the amount of glucosylated steviol glycoside present in the composition is greater than the amount of rebaudioside M present in the composition. In one exemplary embodiment, without limitation, the taste modifier (iii) of the composition may comprise one or more components in an effective amount (one or more) that masks off-notes related to rebaudioside M in the composition and improves mouthfeel.

[0094] The glucosylated steviol glycosides included in the composition, the sweetened composition, and the sweetened consumables may be selected from any one or more steviol glycosides capable of adding one or more glucose units to the molecule by a glucosylation reaction. As an example, but not limited to, glucosylated steviol glycosides included in the sweetened composition include glucosylated stevioside, glucosylated rebaudioside A, glucosylated rebaudioside B, glucosylated rebaudioside C, glucosylated rebaudioside D, glucosylated rebaudioside E, glucosylated rebaudioside F, and glucosylated rebaudioside. The glycosides may be selected from glucosylated rebaudiol glycosides G, glucosylated rebaudiol glycoside H, glucosylated rebaudiol glycoside I, glucosylated rebaudiol glycoside J, glucosylated rebaudiol glycoside K, glucosylated rebaudiol glycoside L, glucosylated rebaudiol glycoside M, glucosylated rebaudiol glycoside N, glucosylated rebaudiol glycoside O, glucosylated dulcoside A, glucosylated dulcoside B, glucosylated rubusoside, any other glucosylated steviol glycoside derived from an extract of Stevia rebaudiana, and mixtures thereof.

[0095] Glucosylated steviol glycosides may have varying degrees of glucosylation. Therefore, glucosylated steviol glycoside(ii) of the composition may consist of a blend of glucosylated steviol glycosides of the same type and have different or varying degrees of glucosylation. Glucosylated steviol glycoside(ii) of the composition may also consist of a blend of one or more different types of glucosylated steviol glycosides having similar degrees of glucosylation. Glucosylated steviol glycoside(ii) of the composition may further consist of a blend of one or more different types of glucosylated steviol glycosides, each having different or varying degrees of glucosylation.

[0096] The glucosylated steviol glycoside may include a blend of at least one glucosylated steviol glycoside and at least one residual steviol glycoside. The residual steviol glycoside refers to an unreacted, unglucosylated steviol glycoside. Residual steviol glycosides may include residual stevioside, residual rebaudioside A, residual rebaudioside B, residual rebaudioside C, residual rebaudioside D, residual rebaudioside E, residual rebaudioside F, residual rebaudioside G, residual rebaudioside H, residual rebaudioside I, residual rebaudioside J, residual rebaudioside K, residual rebaudioside L, residual rebaudioside M, residual rebaudioside N, residual rebaudioside O, residual dulcoside A, residual dulcoside B, residual rubusoside, any other residual steviol glycoside derived from Stevia rebaudiana extract, and mixtures thereof. A blend of at least one glucosylated steviol glycoside and at least one residual steviol glycoside may contain about 1 percent and 15 percent of at least one residual steviol glycoside. According to one embodiment, a blend of at least one glucosylated steviol glycoside and at least one residual steviol glycoside may contain at least one residual steviol glycoside in amounts of about 1 percent to 10 percent, or about 1 percent to about 8 percent, or about 1 percent to about 6 percent, or about 1 percent to about 4 percent, or about 1 percent to about 2 percent.

[0097] Glucosylated steviol glycosides may be prepared by preparing a reaction mixture of one or more steviol glycosides, a source of glucose units to be added to the steviol glycoside molecules, an enzyme to catalyze the glucosylation reaction, and a suitable solvent. According to one embodiment, glucosylated steviol glycosides are prepared by preparing a reaction mixture of one or more steviol glycosides, starch as a source of glucose units to be added to the steviol glycoside molecules, a CGTase (cyclodextrin glucanotransferase) to catalyze the glucosylation reaction, and water as a solvent. The glycosylation reaction is carried out on the reaction mixture, and the resulting product is purified and dried. As an example, glucosylated steviol glycosides may also be prepared according to the disclosure of JP2001-120218, which is incorporated by reference. Alpha-glycosylsteviol glycoside (alpha-GS) is prepared by alpha-adding glucose to a stevia extract containing at least 1.5 times more RebA than stevioside using cyclodextrin glucosyltransferase.

[0098] The taste modifier may comprise one or more compounds from a broad range of types. According to one exemplary embodiment, the taste modifier (iii) of the composition comprises betaine. Betaine is an amphoteric quaternary ammonium compound and its derivatives, represented by the following general formula: [ka]

[0099] According to other exemplary embodiments, the taste-modifying substance (iii) of the composition includes a substance represented by the following formula and its derivatives: [ka] Here, X in the formula is -OH, -O(CO)R, -OPO3H2, -PO3H2, -OSO3H, -SO3H, and R is a C2-C group containing at least one carboxylic acid group and its derivatives. 10 It is a compound. This substance is fully described in WO2006 / 009428, which is incorporated herein by reference.

[0100] According to other exemplary embodiments, the taste modifier (iii) of the composition is one or more carboxylic acid-amino acid conjugates and derivatives thereof represented by the following formulas: [ka] The edible derivatives thereof are included, where R1 is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue having 9 to 25 carbon atoms including 1 to 6 double bonds, where R1 and the carbonyl group attached thereto are carboxylic acid residues, and m is 0 or 1. The edible derivatives may include, without limitation, edible salts, including those commonly used in the food and beverage industry, such as chlorides, sulfates, phosphates, gluconates, sodium salts, citrates, carbonates, acetates, and lactates. These carboxylic acid-amino acid conjugates are fully described in WO2013 / 148991, which is incorporated herein by reference.

[0101] According to other exemplary embodiments, the taste modifier (iii) of the composition is one or more carboxylic acid-amino acid conjugates and derivatives thereof represented by the following formulas: [ka] and its edible derivatives, wherein R1 is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds, 1The carbonyl group attached thereto is a carboxylic acid residue, where m is 0 or 1. Edible derivatives include, but are not limited to, chlorides, sulfates, phosphates, gluconates, sodium salts, citrates, carbonates, acetates, and lactates, including edible salts of those typically used in the food and beverage industry. These carboxylic acid-amino acid conjugates are fully described in WO2013 / 149022, which is incorporated herein by reference.

[0102] According to other exemplary embodiments, the taste modifier (iii) of the composition is one or more carboxylic acid-amino acid conjugates and derivatives thereof represented by the following formulas: [ka] and its edible derivatives, wherein R1 is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds, 1 The carbonyl group attached thereto is a carboxylic acid residue, where m is 0 or 1. Edible derivatives include, but are not limited to, chlorides, sulfates, phosphates, gluconates, sodium salts, citrates, carbonates, acetates, and lactates, including edible salts of those typically used in the food and beverage industry. These carboxylic acid-amino acid conjugates are fully described in WO2013 / 149019, which is incorporated herein by reference.

[0103] According to other exemplary embodiments, the taste modifier (iii) of the composition comprises one or more compounds represented by the following formulas and their derivatives: [ka] [ka] [ka] [ka] [ka] The compounds described above are fully described in WO2008 / 119197 and WO2008 / 119196, which are fully incorporated herein by reference.

[0104] According to other exemplary embodiments, the taste modifier (iii) of the composition comprises one or more chlorogenic acids. The term chlorogenic acid refers to a quinic acid conjugate comprising one or more compounds from the family of esters formed between cis and trans cinnamic acids (e.g., caffeic acid, ferulic acid, p-coumaric acid, sinapic acid) and quinic acid. A quinic acid conjugate is represented by the following formula: [ka] Here, an exemplary quinic acid conjugate is defined by the R group substitution shown in the table below: [ka] The use of chlorogenic acid as a taste modifier is fully described in WO2002 / 100192, which is fully incorporated herein by reference.

[0105] According to other exemplary embodiments, the taste modifier (iii) of the composition comprises one or more phenylpyridyl ketones represented by the following formula: [ka] In the formula, R1 is H, OH, O(CH2)2OH, OCH2OCH3 or [Chem.] It may also be so. R2 may be selected from the range of 5-membered and 6-membered heterocycles, and in the formula, R3 may be H or OH. The structure and use of phenylpyridyl ketone as a taste-modifying substance are fully described in WO2012 / 123475 and WO2009 / 105906, which are hereby incorporated herein by reference in their entirety.

[0106] According to another exemplary aspect, the taste-modifying substance (iii) of the composition may include rebaudioside A as described in WO2007 / 121605, WO2008 / 049256 and WO2009 / 023975, and a blend of rebaudioside A and stevioside as described in WO2013 / 060746, all of which are incorporated by reference.

[0107] According to another exemplary aspect, the taste-modifying substance (iii) of the composition may include one or more compounds defined by the following formula and their derivatives (such as their salts): [Chem.] In the formula, R 1 is H, methyl or ethyl; R 2 is H, OH, fluorine, a C1-C4 straight-chain or branched alkyl, a C1-C6 alkoxy (where the alkyl group is straight-chain or branched), or a C3-C5 cycloalkyl moiety: R 3 is H, methoxy, methyl or ethyl; or R 2 and R 3 together form a cross-linking moiety -O-CH2-O- between the phenyl carbon atoms to which they are attached; R 4 is OH or methoxy; and R 5 and R 6 is independently H or methyl; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 The following applies: (i)R 2 and R 3 When they come together and form a bridged moiety -O-CH2-O- between the phenyl carbon atoms to which they are bonded, R 1 , R 5 , R 6 H is H, and R 4 is OH, and (ii)R 4 is OH, and R 1 ~R 3 When H, R 5 , R 6 At least one of them is methyl. These compounds are fully described in WO2011 / 004016, which is fully incorporated herein by reference.

[0108] In other exemplary embodiments, the taste modifier (iii) of the composition may include one or more compounds and derivatives thereof (such as salts thereof) defined by the following formula: R 1 -CR 7 (OR 4 )-CO-NR 2 -CR 8 R 3 -X-OR 5 (I) R 6 -CR 7 (OR 4 )-CO-Az (II) During the ceremony: X represents a covalent bond; C1-C5 alkyl or C2-C5 alkenyl (each optionally substituted with 1-4 substituents selected from hydroxyl, C1-C3 alkyl, and C1-C3 alkenyl); R1 and R 7 This independently represents hydrogen; or a C1-C8 alkyl, C2-C8 alkenyl, or C3-C8 cycloalkyl (each optionally substituted with 1 to 8 substituents selected from hydroxyl, oxo, C1-C3 alkyl; C2-C3 alkenyl, and C1-C3 carboxyl); R 2 is hydrogen; or C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, or C1-C6 acyl (each optionally substituted with 1-6 substituents selected from hydroxyl, C1-C3 alkyl, and C2-C3 alkenyl); R 3 and R 8 These independently represent hydrogen; hydroxyl; or C1-C8 alkyl, C2-C8 alkenyl, or C3-C8 cycloalkyl (each optionally substituted with 1 to 8 substituents selected from hydroxyl, C1-C3 alkyl, and C2-C3 alkenyl); R 4 represents hydrogen, C1-C3 acyl, or C1-C3 alkyl; R 5 is a phosphate group selected from hydrogen, C1-C3 acyl, C1-C3 alkyl, monophosphate, diphosphate, and triphosphate, or a C2-C5 carboxyl (which may be further optionally substituted with 1-3 substituents selected from hydroxyl, oxo, and C1-C3 carboxyls); R 6 This represents a C2-C6 alkyl or C4-C6 cycloalkyl (each optionally substituted with 1 to 6 hydroxyl groups and each optionally substituted with 1 to 4 substituents selected from C1-C3 alkyl and C1-C3 carboxyl groups); and Az represents an amino acid residue; and the CO-Az bond represents an amide bond. However, R 1 -CR 7 (OR 4 )-CO- does not represent a hexose or heptose sugar acid residue containing more than 4 hydroxyl groups. These compounds are fully described in WO2005 / 102071 and WO / 2006 / 009425, which are fully incorporated herein by reference.

[0109] In other exemplary embodiments, the taste modifier (iii) of the composition may contain choline chloride in an amount ranging from 500 ppb to 500 ppm, specifically in an amount ranging from about 10 ppm to about 50 ppm, as described in WO2011 / 073187 (incorporated by reference). In other exemplary embodiments, the taste modifier (iii) of the composition may include gamma-aminobutyric acid as described in WO2011 / 039340 (incorporated by reference).

[0110] In other exemplary embodiments, the taste modifier (iii) of the composition may include a mega-lipid complex, as described in WO2016 / 062743 (incorporated by reference). A mega-lipid complex refers to a composition prepared from arachidonic acid-rich unicellular oils. Unicellular oils are edible oils extracted from unicellular microorganisms such as algae, bacteria, and yeasts. Methods for preparing mega-lipid complexes are also described in U.S. 5,178,892 and U.S. 2007 / 009642. Each of rebaudioside M and glucosylated steviol glucoside may be present in the composition in amounts greater than, less than, or equivalent to their respective sweetness perception thresholds.

[0111] According to one exemplary embodiment, both rebaudioside M and glucosylated steviol glucoside are present in the composition in amounts below their respective sweetness perception thresholds. In one exemplary embodiment, both rebaudioside M and glucosylated steviol glucoside are present in the composition in amounts greater than their respective sweetness perception thresholds.

[0112] In one exemplary embodiment, rebaudioside M is present in the composition in an amount greater than its sweetness recognition threshold, and glucosylated steviol glucoside is present in an amount less than its sweetness recognition threshold. In one exemplary embodiment, rebaudioside M is present in the composition in an amount below its sweetness recognition threshold, and glucosylated steviol glucoside is present in an amount above its sweetness recognition threshold.

[0113] In one exemplary embodiment, rebaudioside M is present in the composition in an amount of about 50 to about 360 ppm, and glucosylated steviol glycoside is present in the composition in an amount of about 60 to about 430 ppm. In one exemplary embodiment, rebaudioside M is present in the composition in an amount greater than 0 and up to about 25 ppm, and glucosylated steviol glycoside is present in the composition in an amount greater than 0 and up to about 100 ppm.

[0114] In one exemplary embodiment, rebaudioside M is present in the composition in an amount of about 50 to about 360 ppm, and glucosylated steviol glycoside is present in the composition in an amount greater than 0 and up to about 100 ppm. In one exemplary embodiment, rebaudioside M is present in the composition in an amount greater than 0 and up to about 25 ppm, and glucosylated steviol glycoside is present in the composition in an amount of about 60 to about 430 ppm.

[0115] According to one embodiment, the amount of (i) rebaudioside M present in the composition is approximately 50 ppm to approximately 360 ppm, and not limited to these, but approximately 50 to approximately 300 ppm, approximately 50 ppm to approximately 250 ppm, approximately 50 ppm to approximately 200 ppm, approximately 50 ppm to approximately 150 ppm, approximately 50 ppm to approximately 100 ppm, approximately 100 ppm to approximately 360 ppm, approximately 100 ppm to approximately 300 ppm, approximately 100 ppm to approximately 250 ppm, and approximately 100 ppm to approximately 2 It is within all ranges within this range, encompassing up to 00 ppm, approximately 100 ppm to approximately 150 ppm, approximately 150 ppm to approximately 360 ppm, approximately 150 ppm to approximately 300 ppm, approximately 150 ppm to approximately 250 ppm, approximately 150 ppm to approximately 200 ppm, approximately 200 ppm to approximately 360 ppm, approximately 200 ppm to approximately 300 ppm, approximately 200 ppm to approximately 250 ppm, 250 ppm to approximately 360 ppm, and approximately 250 ppm to approximately 300 ppm.

[0116] According to one embodiment, the amount of (i) rebaudioside M present in the composition is from more than 0 ppm to about 25 ppm, and not limited to, but from more than 0 ppm to about 24 ppm, from more than 0 ppm to about 23 ppm, from more than 0 ppm to about 22 ppm, from more than 0 ppm to about 21 ppm, from more than 0 ppm to about 20 ppm, and from more than 0 ppm to about 1 Up to 9 ppm, from above 0 ppm to approximately 18 ppm, from above 0 ppm to approximately 17 ppm, from above 0 ppm to approximately 16 ppm, from above 0 ppm to approximately 15 ppm, from above 0 ppm to approximately 14 ppm, from above 0 ppm to approximately 13 ppm, from above 0 ppm to approximately 12 ppm, from above 0 ppm to approximately 11 ppm, from above 0 ppm to approximately 10 ppm Up to pm, from more than 0 ppm to approximately 9 ppm, from more than 0 ppm to approximately 8 ppm, from more than 0 ppm to approximately 7 ppm, from more than 0 ppm to approximately 6 ppm, from more than 0 ppm to approximately 5 ppm, from more than 0 ppm to approximately 4 ppm, from more than 0 ppm to approximately 3 ppm, from more than 0 ppm to approximately 2 ppm, from more than 0 ppm to approximately 1 ppm, approximately 5 ppm It is within all ranges within this range, encompassing approximately 25 ppm, approximately 5 ppm to approximately 20 ppm, approximately 5 ppm to approximately 15 ppm, approximately 5 ppm to approximately 10 ppm, approximately 10 ppm to approximately 25 ppm, approximately 10 ppm to approximately 20 ppm, approximately 10 ppm to approximately 15 ppm, approximately 15 ppm to approximately 25 ppm, approximately 15 ppm to approximately 20 ppm, and approximately 20 ppm to approximately 25 ppm.

[0117] According to one embodiment, the amount of (ii) glucosylated steviol glycoside in the composition is about 60 ppm to about 430 ppm, and not limited to these, but about 60 to about 400 ppm, about 60 ppm to about 350 ppm, about 60 ppm to about 300 ppm, about 60 ppm to about 250 ppm, about 60 ppm to about 200 ppm, about 60 ppm to about 150 ppm, about 60 ppm From m to approximately 100 ppm, from approximately 60 ppm to approximately 75 ppm, from approximately 100 ppm to approximately 430 ppm, from approximately 100 ppm to approximately 400 ppm, from approximately 100 ppm to approximately 350 ppm, from approximately 100 ppm to approximately 300 ppm, from approximately 100 ppm to approximately 250 ppm, from approximately 100 ppm to approximately 200 ppm, from approximately 100 ppm to approximately 150 ppm, from approximately 150 ppm to approximately 430 ppm, From approximately 150 ppm to approximately 400 ppm, from 150 ppm to approximately 350 ppm, from approximately 150 ppm to approximately 300 ppm, from approximately 150 ppm to approximately 250 ppm, from approximately 150 ppm to approximately 200 ppm, from approximately 200 ppm to approximately 430 ppm, from approximately 200 ppm to approximately 350 ppm, from approximately 200 ppm to approximately 300 ppm, from approximately 200 ppm to approximately 250 ppm, from approximately 250 ppm to approximately 43 It is within all ranges within this range, encompassing up to 0 ppm, approximately 250 ppm to approximately 400 ppm, approximately 250 ppm to approximately 350 ppm, approximately 250 ppm to approximately 300 ppm, approximately 300 ppm to approximately 430 ppm, approximately 300 ppm to approximately 400 ppm, approximately 300 ppm to approximately 350 ppm, approximately 350 ppm to approximately 430 ppm, and approximately 350 ppm to approximately 400 ppm.

[0118] According to one embodiment, the amount of (ii) glucosylated steviol glycoside in the composition is from more than 0 ppm to about 28 ppm, and not limited to, but from more than 0 ppm to about 27 ppm, from more than 0 ppm to about 26 ppm, from more than 0 ppm to about 25 ppm, from more than 0 ppm to about 24 ppm, from more than 0 ppm to about 23 ppm, from more than 0 ppm to about 22 ppm, and from 0 ppm. From a moderate amount up to approximately 21 ppm, from an amount greater than 0 ppm up to approximately 20 ppm, from an amount greater than 0 ppm up to approximately 19 ppm, from an amount greater than 0 ppm up to approximately 18 ppm, from an amount greater than 0 ppm up to approximately 17 ppm, from an amount greater than 0 ppm up to approximately 16 ppm, from an amount greater than 0 ppm up to approximately 15 ppm, from an amount greater than 0 ppm up to approximately 14 ppm, from an amount greater than 0 ppm up to approximately 13 ppm, from an amount greater than 0 ppm up to approximately 12 ppm, 0 ppm From more than ppm up to approximately 11 ppm, from more than 0 ppm up to approximately 10 ppm, from more than 0 ppm up to approximately 9 ppm, from more than 0 ppm up to approximately 8 ppm, from more than 0 ppm up to approximately 7 ppm, from more than 0 ppm up to approximately 6 ppm, from more than 0 ppm up to approximately 5 ppm, from more than 0 ppm up to approximately 4 ppm, from more than 0 ppm up to approximately 3 ppm, from more than 0 ppm up to approximately 2 ppm, more than 0 ppm It is within the range encompassing approximately 1 ppm from 5 ppm, approximately 5 ppm to approximately 25 ppm, approximately 5 ppm to approximately 20 ppm, approximately 5 ppm to approximately 15 ppm, approximately 5 ppm to approximately 10 ppm, approximately 10 ppm to approximately 25 ppm, approximately 10 ppm to approximately 20 ppm, approximately 10 ppm to approximately 15 ppm, approximately 15 ppm to approximately 25 ppm, approximately 15 ppm to approximately 20 ppm, and approximately 20 ppm to approximately 25 ppm.

[0119] According to one exemplary embodiment, rebaudioside M is present in the composition in an amount ranging from about 80 to about 100 ppm, and glucosylated steviol glycoside is present in the composition in an amount ranging from 100 ppm to about 120 ppm. According to another exemplary embodiment, rebaudioside M is present in the composition in an amount ranging from about 90 to about 100 ppm, and glucosylated steviol glycoside is present in the composition in an amount ranging from 110 ppm to about 120 ppm. In one embodiment, the amount of (iii) taste-modifying substances present in the composition is between approximately 500 ppm and approximately 4000 ppm, or between approximately 500 ppm and approximately 3500 ppm, or between approximately 500 ppm and approximately 3000 ppm, or between approximately 500 ppm and approximately 2500 ppm, or between approximately 500 ppm and approximately 2000 ppm, or between approximately 500 ppm and approximately 1500 ppm, or between approximately 500 ppm and approximately 1000 ppm, or between approximately 1000 ppm and approximately 4000 ppm, or between approximately 1000 ppm and approximately 3000 ppm, or between approximately 1000 ppm and approximately 2000 ppm, or between approximately 2000 ppm and approximately 4000 ppm, or between approximately 2000 ppm and approximately 3000 ppm.

[0120] The composition would be used to replace 5 percent or more, or 10 percent or more, or 20 percent or more, or 30 percent or more, or 40 percent or more, or 50 percent or more, or 60 percent or more, or 70 percent or more, or 80 percent or more, or 90 percent or more, of the sugar in a sweetened consumable. According to one embodiment, the composition would be used to replace about 30 percent to about 100 percent of the sugar in a sweetened consumable. According to one exemplary embodiment, the composition would be used to replace about 30 percent to about 90 percent, or about 30 percent to about 80 percent, or about 30 percent to about 70 percent, or about 30 percent to about 60 percent, or about 30 percent to about 50 percent, of the sugar in a sweetened consumable. In other exemplary embodiments, the composition would be used to replace about 50 percent to about 100 percent, or about 50 percent to about 90 percent, or about 50 percent to about 80 percent, or about 50 percent to about 70 percent, or about 50 percent to about 60 percent of the sugar in a sweetened consumable. In other exemplary embodiments, the composition would be used to replace about 30 percent, or about 50 percent, or about 70 percent, or about 80 percent, or about 100 percent of the sugar in a sweetened consumable. The amounts of rebaudioside M and glucosylated steviol glycoside present in the composition are effective in replacing the desired amount of sugar.

[0121] According to one exemplary embodiment, the combined amount of (i) rebaudioside M and (ii) glucosylated steviol glycoside is between approximately 85 percent and approximately 95 percent, and all amounts within this range, and the amount of (iii) taste modifier is between approximately 5 percent and approximately 15 percent, and all amounts within this range, or the combined amount of (i) rebaudioside M and (ii) glucosylated steviol glycoside is between approximately 86 percent and approximately 95 percent, and the amount of (iii) taste modifier is between approximately 5 percent and approximately 14 percent, or the combined amount of (i) rebaudioside M and (ii) glucosylated steviol glycoside is between approximately 87 percent and approximately 95 percent, and the amount of (iii) taste modifier is approximately 5 The amounts are (i) rebaudioside M and (ii) glucosylated steviol glycoside combined, ranging from approximately 10 percent to about 13 percent, or (i) rebaudioside M and (ii) glucosylated steviol glycoside combined, ranging from approximately 88 percent to about 95 percent, and (iii) the amount of taste modifiers ranging from approximately 5 percent to about 12 percent, or (i) rebaudioside M and (ii) glucosylated steviol glycoside combined, ranging from approximately 89 percent to about 95 percent, and (iii) the amount of taste modifiers ranging from approximately 5 percent to about 11 percent, or (i) rebaudioside M and (ii) glucosylated steviol glycoside combined, ranging from approximately 80 percent to about 95 percent, and (iii) the amount of taste modifiers ranging from approximately 5 percent to about 10 percent.

[0122] Sweetened consumables such as carbonated soft drinks or non-carbonated fruit juices may include a beverage base containing at least 30 percent to 70 percent and all amounts within this range of sweeteners, or a food or beverage base in amounts of approximately 40 percent to 65 percent, or a food or beverage base in amounts of approximately 40 percent to 50 percent. The sweetened consumables are compositions containing approximately 0.1 percent to approximately 0.6 percent of (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier, or compositions containing approximately 0.1 percent to approximately 0.5 percent and any amount within this range of (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier, or compositions containing approximately 0.1 percent to approximately 0.4 percent of (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier, or approximately 0.1 percent to approximately 0.3 percent of (i) rebaudioside The composition may include (ii) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier, or a composition containing about 0.1 percent to about 0.2 percent of (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier, or a composition containing about 0.1 percent to about 0.15 percent of (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier, or a composition containing about 0.1 percent to about 0.125 percent of (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier.

[0123] The sweetened milk beverage may contain a composition containing (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier in amounts ranging from approximately 0.05 percent to approximately 0.3 percent of the milk beverage base and the whole milk beverage, or approximately 0.05 percent to approximately 0.275 percent of the whole milk beverage, or approximately 0.05 percent to approximately 0.25 percent of the whole milk beverage, or approximately 0.05 percent to approximately 0.2 percent of the whole milk beverage, or approximately 0.05 percent to approximately 0.15 percent of the whole milk beverage, or approximately 0.05 percent to approximately 0.1 percent of the whole milk beverage.

[0124] The sweetened yogurt composition may contain (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier in amounts ranging from about 0.05 percent to about 0.2 percent of the yogurt base and the total yogurt composition, or from about 0.1 percent to about 0.2 percent of the total yogurt composition, or from about 0.1 percent to about 0.185 percent of the total yogurt composition, or from about 0.1 percent to about 0.15 percent of the total yogurt composition, or from about 0.1 percent to about 0.125 percent of the total yogurt composition, or from about 0.05 percent to about 0.1 percent of the total yogurt composition.

[0125] At least one sweetener included in a sweetened composition or sweetened consumable may be selected from one or more of the nutrient-rich and non-nutrient-rich sweeteners described herein. The composition may be in any preferred form, for example, a solid (e.g., powder, granules, tablets), a solution (e.g., aqueous solution), an emulsion, or a suspension. For example, the composition may further contain a diluent or filler such as dietary fiber.

[0126] Food compositions as disclosed herein include, for example, the following: - Wet / liquid soups, whether concentrated or in a container, including frozen soups. For the purposes of this definition, soup(singular or plural) means a food prepared from cooking meat, poultry, fish, vegetables, grains, fruits and other ingredients in liquid, which may include visible pieces of some or all of these ingredients. It may be clear (as broth) or thick (as chowder), smooth, pureed or chunky, ready-to-serve, semi-concentrated or concentrated, and hot or cold, and may be served as the first course of a meal, or as a main course or as a snack between meals (to be drunk little by little like a beverage). Soup may be used as an ingredient to balance other meal components and may range from broth (consommé) to sauce (cream or cheese-based soup).

[0127] - Concentrated liquid products encompassing powders, granules, pastes, concentrated bouillons, bouillons and pressed cube bouillon-like products; dehydrated foods and cooking foods encompassing cooking aids such as tablets or powders or granules, which are sold as finished products or individually as ingredients, sauces and recipe mixes (regardless of technology) within a product. - Meal solution products such as dehydrated and freeze-dried soups, including dehydrated soup mixes, dehydrated instant soups, and dehydrated ready-to-cook soups; dehydrated or ambient preparations of ready-made dishes; and meals and single-serve entrees, including pasta, potato, and rice dishes.

[0128] - Meal embellishment products such as sauces or sauce mixes, including salad recipe mixes, sold as seasonings, marinades, salad dressings, salad toppings, dips, breadcrumbs, batter mixes, shelf-stable spreads, barbecue sauces, liquid recipe mixes, concentrates, finished products, or as ingredients within products, whether dehydrated, liquid, or frozen. - Not limited to, alcoholic and non-alcoholic ready-to-drink and dry powder beverages, carbonated and non-carbonated beverages, beverages including carbonated water, fruit or vegetable juices, and beverage mixes and concentrates containing alcoholic and non-alcoholic beverages.

[0129] - Confectionery products, such as cakes, cookies, pies, candies, chewing gum, gelatin, ice cream, sorbet, pudding, jam, jelly, salad dressings, and other condiments, grains and herbs, and other breakfast foods, canned fruits and fruit sauces, etc. - Dairy products such as milk, cheese, and yogurt. - For example, a pharmaceutical composition which may be in the form of a syrup, emulsion, suspension, solution or other liquid form. - For example, dental compositions including mouth fresheners, gargles, mouthwashes, toothpastes, toothpastes (tooth polish), dentifrice, mouth sprays, and dental floss. - Edible gel composition

[0130] The compositions disclosed herein may further comprise a base composition. For example, the edible compositions disclosed herein may further comprise an edible base composition. This refers to all components necessary for the composition, except for combinations of high-intensity sweeteners and low-efficacy sweeteners (e.g., sweetness-modifying compositions). The base composition may be a sweetened base composition comprising, for example, at least one other sweetener present in an amount equivalent to or greater than its sweetness perception threshold and / or an amount having sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent. These will naturally vary in both properties and proportions depending on the properties and use of the composition, but they may be well known in the art and used in proportions recognized in the art. Thus, formulation of such base compositions for all conceivable purposes is within the ordinary skill of the art.

[0131] The components in the base composition are not limited to these, but may include anti-caking agents, anti-foaming agents, antioxidants, binders, colorants, diluents, disintegrants, emulsifiers, encapsulants or formulations, enzymes, fats, flavor enhancers, flavoring agents, rubber, lubricants, polysaccharides, preservatives, proteins, solubilizers, solvents, stabilizers, sugar derivatives, surfactants, sweeteners, vitamins, waxes, etc. Solvents that may be used are known to those skilled in the art and include, for example, ethanol, ethylene glycol, propylene glycol, glycerin, and triacetin. Encapsulators and rubbers include maltodextrin, gum arabic, alginic acid, gelatin, modified starch, and polysaccharides.

[0132] Examples of additives, excipients, carriers, diluents, or solvents for flavor or fragrance compounds can be found, for example, in "Perfume and Flavour Materials of Natural Origin," S. Arctander, Ed., Elizabeth, NJ, 1960; "Perfume and Flavour Chemicals," S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; "Flavourings," E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998; and "CTFA Cosmetic Ingredient Handbook," JM Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0133] The proportion of one or more high-intensity sweeteners and one or more low-intensity sweeteners (one or more) in combination (e.g., a sweetness-modifying composition) or one or more sweetness enhancers selected from mogroside IV, siamenoside, and neomogroside will depend on the properties of the composition and the desired degree and characteristics of sweetness. Those skilled in the art can easily determine the appropriate proportions in all cases using only simple, unoriginal experimental methods. The amounts and proportions disclosed herein are illustrative only, and flavorists may seek specific effects by working outside this scope; they should be considered only as indicators.

[0134] The pH of the compositions disclosed herein may be any pH that does not adversely affect the flavor of the sweetener blend. For example, the pH may be in the range of about 1.8 to about 8, or about 2 to about 5. Those skilled in the art will be able to identify suitable concentrations of each sweetener and use them according to the pH of the composition.

[0135] The use of one or more low-potency sweeteners in combination with one or more high-intensity sweeteners may improve one or more sweetness characteristics in the sweetened composition compared to, for example, the use of one or more high-intensity sweeteners alone. Therefore, the sweetened compositions disclosed herein may have one or more improved sweetness characteristics compared to, for example, a sweetened composition in the absence of one or more low-potency sweeteners. The use of one or more sweetness enhancers selected from mogroside IV, siamenoside, and neomogroside may improve one or more sweetness characteristics in the sweetened composition compared to, for example, the use of a different sweetness enhancer such as monk fruit extract instead of one or more of mogroside IV, siamenoside, and neomogroside.

[0136] The sweetened compositions disclosed herein may have one or more sweetening characteristics that are more similar to sucrose, for example, compared to sweetened compositions in the absence of one or more low-potency sweeteners, or compared to sweetened compositions containing different sweetening enhancers. The sweetened compositions disclosed herein may have a less lingering sweet flavor compared, for example, to sweetened compositions in the absence of one or more low-potency sweeteners, or to sweetened compositions containing different sweeteners.

[0137] The sweetened compositions disclosed herein may have reduced bitter flavors, and / or astringent flavors, and / or metallic flavors, and / or licorice flavors, compared, for example, to sweetened compositions in the absence of one or more low-potency sweeteners, or to sweetened compositions containing different sweeteners. The sweetened compositions disclosed herein may have a stronger sweetness impact compared, for example, to sweetened compositions in the absence of one or more low-potency sweeteners, or to sweetened compositions containing different sweetness enhancers. The compositions with comparative sweetness are identical except that they do not contain any of the one or more low-efficacy sweeteners, or they are identical except that they contain a different sweetener instead of one or more mogrosides, such as mogroside IV, siamenoside, and neomogroside.

[0138] use Provided herein is the use of a combination of one or more high-intensity sweeteners and one or more low-intensity sweeteners to enhance the sweetness of a composition comprising at least one other sweetener present in an amount equivalent to or greater than the sweetness perception threshold, and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent. The combination of one or more high-intensity sweeteners and one or more low-intensity sweeteners has a sweetness of less than 1.5% (w / v) sucrose equivalent. One or more high-intensity sweeteners, one or more low-intensity sweeteners and at least one other sweetener may be in any form disclosed herein.

[0139] The use of one or more mogrosides, e.g., one or more of mogrosides, such as mogroside IV, siamenoside, and neomogroside, is provided herein to enhance the sweetness of a composition comprising at least one other sweetener present in an amount equivalent to or greater than the sweetness threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent.

[0140] Therefore, a method is provided for enhancing the sweetness of a sweetened composition, the method comprising: providing a base composition containing at least one sweetener in an amount having a sweetness exceeding its sweetness recognition threshold and / or an amount having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent; and adding at least one low-efficacy sweetener, at least one high-intensity sweetener; or adding one or more mogrosides, for example, one or more of mogroside IV, siamenoside, and neomogroside. Each component of the final composition may be added in any order to obtain the desired final composition. The method may also include, for example, mixing the components.

[0141] One or more high-intensity sweeteners and / or a combination of one or more high-intensity sweeteners and one or more low-efficacy sweeteners (for example, a sweetening composition), and / or one or more mogrosides, such as one or more of mogroside IV, siamenoside, and neomogroside, may increase the sweetness of the sweetened composition to an amount equivalent to or greater than, for example, about 1.0% (w / v) sucrose equivalent. For example, one or more high-intensity sweeteners and / or combinations of one or more high-intensity sweeteners and one or more low-efficacy sweeteners, and / or one or more mogrosides, such as one or more of mogroside IV, siamenoside, and neomogroside, may increase the sweetness of a sweetened composition by an amount equivalent to or greater than approximately 1.1% (w / v) sucrose equivalent, or equivalent to or greater than approximately 1.15% (w / v) sucrose equivalent, or equivalent to or greater than approximately 1.2% (w / v) sucrose equivalent, or equivalent to or greater than approximately 1.25% (w / v) sucrose equivalent. The composition may, for example, include at least one other sweetener.

[0142] The use of one or more low-potency sweeteners to improve one or more sweetness characteristics of a composition sweetened with one or more high-potency sweeteners is also provided herein. The one or more high-potency sweeteners and one or more low-potency sweeteners are used in amounts having a sweetness of less than about 1.5% (w / v) sucrose equivalent.

[0143] In one embodiment, the use of a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier is also provided, for the purpose of improving one or more sweetness characteristics of a sweetened composition compared to each or more sweetness characteristics of the sweetened composition in the absence of the composition. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition. In one embodiment, the use of a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier is also provided, for the purpose of improving the upfront sweetness of a sweetened composition compared to the upfront sweetness of a sweetened composition in the absence of the composition. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition.

[0144] In one embodiment, the use of a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier is also provided, for the purpose of reducing the bitter off-note of a sweetened composition compared to the bitter off-note of the sweetened composition in the absence of the composition. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition. In one embodiment, the use of a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier is also provided, for the purpose of reducing the dry and / or astringent taste of a sweetened composition compared to the dry and / or astringent taste of a sweetened composition in the absence of the composition. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition.

[0145] In one embodiment, the use of a composition comprising (i) rebaudioside M or glucosylated steviol glycoside and (ii) an effective amount of a taste modifier is also provided, for the purpose of improving each of the sweetness characteristics(s) of a sweetened composition compared to one or more sweetness characteristics(s) of a sweetened composition in the absence of the composition. In one embodiment, the use of a composition comprising (i) rebaudioside M or glucosylated steviol glycoside and (ii) an effective amount of a taste modifier is also provided for the purpose of improving the upfront sweetness of a sweetened composition compared to the upfront sweetness of a sweetened composition in the absence of the composition. In one embodiment, the use of a composition comprising (i) rebaudioside M or glucosylated steviol glycoside and (ii) an effective amount of a taste modifier is also provided for reducing the amount of sugar in a sweetened composition.

[0146] In one embodiment, the use of a composition comprising (i) rebaudioside M or glucosylated steviol glycoside and (ii) an effective amount of a taste modifier is also provided for the purpose of reducing the bitter off-note of a sweetened composition compared to the bitter off-note of the sweetened composition in the absence of the composition. In one embodiment, the use of a composition comprising (i) rebaudioside M or glucosylated steviol glycoside and (ii) an effective amount of a taste modifier is also provided for reducing the dry and / or astringent taste of a sweetened composition compared to the dry and / or astringent taste of a sweetened composition in the absence of the composition.

[0147] Therefore, a method is provided to improve one or more sweetness characteristics of a composition that has been sweetened with one or more high-intensity sweeteners in an amount having a sweetness of less than 1.5% (w / v) sucrose equivalent, the method comprising providing a composition containing one or more high-intensity sweeteners, and adding one or more low-efficacy sweeteners. Each component of the final composition may be added in any order to obtain the desired final composition. The method may, for example, include mixing the components. Improving one or more sweetness characteristics of a composition that has been sweetened with a high-intensity sweetener may provide, for example, a sweetness characteristic that is more equivalent to that of sucrose.

[0148] In one embodiment, the provided method enhances the sweetness of a sweetened composition, comprising: providing a base composition containing at least one sweetener present in an amount equal to or exceeding its sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent; and adding the composition to the base composition, a sweetness-modifying composition containing (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition.

[0149] In one embodiment, the provided method is to improve one or more sweetness characteristics of a sweetened composition, comprising: providing a base composition comprising at least one sweetener present in an amount equal to or exceeding the sweetness recognition threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent; and adding the composition to the base composition, a sweetness-modifying composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition.

[0150] In one embodiment, the provided method is to improve the upfront sweetness of a sweetened composition, comprising: providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent; and adding the composition to the base composition, a sweetness-modifying composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition.

[0151] In one embodiment, the provided method for reducing the lingering bitter, metallic and / or licorice off-notes of a sweetened composition is to provide a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, and to add the composition to a composition comprising the base composition, (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition.

[0152] In one embodiment, the provided method is to improve the dry and / or astringent mouthfeel of a sweetened composition, comprising: providing a base composition comprising at least one sweetener present in an amount equal to or exceeding its sweetness perception threshold and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent; and adding the composition to the base composition, a sweetening composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) an effective amount of a taste modifier. The amounts and ratios of rebaudioside M and glucosylated steviol glycoside present in the composition are any of those described herein for the composition.

[0153] Astringency is defined by the American Society for Testing and Materials (ASTM, 2004) as a complex of sensations resulting from the contraction, stretching, or wrinkling of epithelium as a result of exposure to substances such as alum and tannins. Astringency molecules are thought to react with salivary proteins, particularly proline-rich proteins and glycoproteins that act as natural lubricants, such as mucin, causing their precipitation and aggregation, and consequently leading to a loss of smoothness and the rough, "sandpaper-like," or dry sensation associated with astringency in the mouth. Astringency can be inherently present in certain consumables, such as tea, wine, yogurt, and plant proteins. Astringency can also be introduced into consumables as a result of adding certain ingredients, such as vitamins, minerals, amino acids, proteins, peptides, or antioxidants. While these ingredients may be employed as additives with the intention of improving health and food safety, or for nutritional reasons, they can also be associated with the perception of astringency and undesirable mouthfeel characteristics.

[0154] Mouthfeel (or "mouth feel") refers to the physical sensations experienced or felt in the mouth, created by food and beverages, or by compositions added to food or beverages. Mouthfeel may also refer to the mouthfeel in contact with the tongue, palate, teeth, rubber, or throat. Mouthfeel is considered to be distinct in nature from flavor, but is considered to have an equal or even greater impact on a person's enjoyment or preference for one food over another. Typical mouthfeel descriptors used to describe perceived sensations include acidity (metallic, citrusy, bright), density (dense, fluffy), dryness (arid, burnt), granularity (fine, powdery, grainy, chalky), stickiness (chewy, tough), hardness (chewy, soft), weight (full, heavy), irritation (prickly, throbbing), mouth coating (oily, buttery), roughness (abrasive, textured), slipperiness (sticky, stringy), smoothness (glossy, velvety), uniformity (uniform, uneven), and viscosity (full-bodied, light-bodied).

[0155] Sweetness characteristics may also refer to the flavor profile, which describes the intensity of the flavor and the characteristics of the perception of a given compound. Examples of sweetness flavor characteristics include sweetness intensity, bitterness, and black licorice. Sweetness characteristics may also refer to the temporal profile, which describes the change in the perception of sweetness over time. All sweeteners exhibit characteristic onset time (AT) and disappearance time (ET). In contrast to carbohydrate sweeteners, most high-potency sweeteners exhibit an extended ET (long-lasting). Generally, the detected sucrose equivalent rises sharply to the maximum response level and then tapers over time. The longer the taper, the greater the lingering sweetness after the detected compound.

[0156] In one embodiment, one or more low-potency sweeteners may be used to reduce the lingering sweet flavor of a sweetened composition containing one or more high-intensity sweeteners. In other words, low-potency sweeteners may be used to reduce the disappearance time (ET) of a sweetened composition containing one or more high-intensity sweeteners. This relates to the undesirable lingering of a sweet flavor in the mouth after the composition has been first ingested or spat out. A lingering sweet flavor may refer, for example, to the length of time it persists after the sweet flavor is first detected, how quickly its intensity decreases or fades after the sweet flavor is first detected, and its intensity after the sweet flavor is detected. One or more low-potency sweeteners may, for example, reduce the length of time the sweet flavor persists after it is first detected, and / or increase the rate at which it decreases after it is first detected, and / or reduce its intensity after it is first detected.

[0157] In one embodiment, one or more low-potency sweeteners may be used to reduce the bitter and / or astringent and / or metallic and / or licorice flavor of a sweetened composition containing one or more high-potency sweeteners. The term "licorice" refers to the sweet flavor of the compound. In one embodiment, one or more low-potency sweeteners may be used to enhance the sweetness impact of a sweetened composition containing one or more high-intensity sweeteners. The sweetness impact relates to the length of time before the sweetness is first detected and the intensity at which the sweetness is first detected. One or more low-potency sweeteners may, for example, decrease the amount of time before the sweetness is first detected and / or increase the intensity at which the sweetness is first detected. The degree of sweetness and other sweetness characteristics described herein may be evaluated by a tasting panel of skilled experts, such as those described in the following examples.

[0158] Manufacturing method Methods for preparing the compositions disclosed herein are further provided herein. The compositions may conform to any embodiment disclosed herein. The method may include combining the components of the desired composition in desired proportions, and optionally mixing the components together. The components may be combined and mixed in any preferred order. Those skilled in the art will identify a suitable method for preparing the composition (for example, a suitable order for combining or mixing the components) depending on the properties of the composition and the desired degree and characteristics of sweetness. The method may include, for example, providing a desired base composition and adding a sweetener thereto.

[0159] Each of the sweeteners disclosed herein may be produced by a synthetic process, or by a biological (e.g., enzymatic) or fermentation process, or may be isolated from a natural source such as a plant or fruit. The process may include, for example, contacting at least one mogrol precursor substrate with a mogroside pathway enzyme. The enzyme may be present, for example, in a cell lysate or in a host cell (e.g., a recombinant host cell). The enzyme may be, for example, a UGT enzyme (UDP-glucuronosyltransferase).

[0160] For example, mogroside compounds may be prepared by biosynthetic pathways disclosed in WO2013 / 076577 or WO2014 / 086842 (the contents of which are incorporated herein by reference). For example, mogroside V may be produced by the biosynthetic pathway disclosed in Itkin et al., "The biosynthetic pathway of the nonsugar, high-intensity sweetener mogroside V from Siraitia grosvenorii", 7 November 2016, E7619 - E7628 and WO2016 / 038617 (the contents of which are incorporated herein by reference). For example, a mogroside compound may be prepared by modifying another mogroside compound (e.g., by redistributing the glycoside content). For instance, a mogroside compound may be prepared by redistributing the glycoside content of another mogroside compound using an acid or enzyme as disclosed in WO2014 / 150127 (the contents of which are incorporated herein by reference).

[0161] The process may include, for example, the extraction of one or more sweetener compounds from a natural source such as a plant or fruit. This may be followed, for example, by a purification step to produce a high-intensity sweetener, a low-intensity sweetener, or a mixture of sweeteners (for example, a mixture of high-intensity sweeteners such as a mixture of mogrosides). The extract may have, for example, a relatively high content of mogroside V and / or 11-O-mogroside V (for example, at least about 30 wt% or at least about 40 wt%). This may involve fractionation, for example, by flash chromatography. One or more mogroside compounds (for example, mogroside V) may be obtained from the fruit of the monk fruit (Siraitia grosvenorii).

[0162] When a fermentation process is used to produce a target product (e.g., a target mogroside product), the target can be extracted from an aqueous fermentation reaction medium using a suitable solvent (e.g., heptane) and subsequently fractionated. The chemical composition of each fraction can be quantitatively measured by GC / MS (gas chromatography-mass spectrometry). The fractions can be blended to produce desired mogroside compounds (e.g., mogroside V and 11-O-mogroside V) for use in flavoring or other applications. The acceptance of the final blend product can be verified by direct comparison with a reference mogroside flavor product (e.g., an existing natural flavor product available from a commercial supplier).

[0163] example Example 1 method Monk fruit extracts obtained from Blue California (Tomas, Rancho Santa Margarita, California) (extract 4), Azile LLC (Rolling Hills Est, California) (extracts 1 and 2), and Chr. Olesen Group (Gentofte, Denmark) (extract 3) were analyzed, and the compounds present in the extracts were identified. The extract sample solution was prepared by dissolving 16.52 μg of the sample in 25.0 mL of solvent (acetonitrile / water 20 / 80 v / v). 100 μL of this solution was transferred to an HPLC vial, and 900 μL of solvent was added (66.1 ppm solution). 10 μL of the sample solution was transferred to an HPLC vial, and 990 μL of solvent was added (6.61 ppm solution). Both the 66.1 and 6.61 ppm solutions were injected twice onto an LC-MS.

[0164] A calibration (reference) solution of mogroside V was prepared by dissolving 9.22 mg of mogroside V (98.5% mogroside V obtained from AAPIN chemicals Ltd., Oxfordshire, UK) in 10.0 mL of solvent (acetonitrile / water 20 / 80 v / v). The stock solution was stored in a freezer and used to prepare mogroside V solutions at various concentrations (0.11 ppm, 0.34 ppm, 1.02 ppm, 3.07 ppm, and 9.22 ppm). These solutions were also injected twice onto an LC-MS. 2 μL of each solution was injected onto an Acquity C18 BEH 1.7 μm 150 x 2.1 mm column (Waters, Milford, Massachusetts, United States) at 40°C. The compounds were eluted using a mixture of acetonitrile and 0.1% formic acid in water, starting at 20% acetonitrile and progressing to a maximum of 50% acetonitrile over 14 minutes. The gradient returned to its starting value at 1 minute and stabilized at 5 minutes. The flow rate was set to 400 μL throughout the entire run.

[0165] The eluted compounds were detected using liquid chromatography-mass spectrometry (LC / MS). The mass spectrometer was operated in ESI negative mode, measuring 150–2000 Amu at a resolution of 70000. Gas flow rates were 60 for the sheath, 20 for the aux, and 3 for the sweep. The capillary temperature and aux gas heater temperature were set to 380°C and 400°C, respectively.

[0166] The percentage of each component in the extract was calculated using the following equation and calibrated against the curves of calibrated mogroside V (reference) solutions of various concentrations described above.

number

[0167] result Figure 1 shows the chromatogram of the Momordica grosvenori extract (extract 2 in Table 1 below). Table 1 shows the compositions of four different Momordica grosvenori extracts. Mogroside V is the mogroside with the highest concentration among all four extracts (about 45 wt% in extract 1).

Table 1-1

Table 1-2

Table 1-3

[0168] Example 2 Method The Momordica grosvenori fruit extract (extract 1 in Example 1 above) obtained from Azile LCC (Rolling Hills Est, California) containing about 68 wt% mogroside was fractionated by reverse-phase (C-18) flash chromatography. The compounds were eluted using a mixture of MeOH in water starting with 30% methanol (MeOH), followed by a linear gradient of 30 - 80% MeOH, and then finally flushing the column with 80% MeOH. The solvent was introduced at a flow rate of 30 ml / min throughout the separation procedure. The eluted compounds were visualized using a UV detector set at 210 nm and a corona light scattering detector. The % of each component in the extract was calculated using the equation described in Example 1 above.

[0169] The collected fractions were pooled according to Table 2 below and then freeze-dried into powder. The powders corresponding to the various pooled fractions, as given in Table 2, were dissolved at various concentrations on top of 5% sucrose. The flavors of these samples were compared to a 5% sucrose control by three expert panelists (skilled flavorists). Thus, the sweetness-enhancing effect of each fraction or pooled fraction in 5% sucrose was determined.

[0170] result The results are shown in the table below. The entire extract was collected into 22 fractions. Fractions 1-10 do not contain mogroside V. [Table 2-1] [Table 2-2]

[0171] Fractions 1-10 and 19-22 possess the off-flavor characteristic of monk fruit, and do not have an impact that enhances sweetness. A better sweetness-enhancing effect was observed in fractions 12-17, which primarily contained mogrosides. When fractions contained almost pure mogroside V, the lingering, dirty, fermented notes were more pronounced in fractions 14 and 15, among others. Therefore, pure mogroside V has an inherently lingering off-taste.

[0172] Fraction 12 had the cleanest sweetness, but lacked upfront due to a lower percentage of mogroside V. Fraction 13 had a better sweet quality but was slightly more astringent. 11-O-mogroside V and mogroside V are the two main mogroids in these two fractions, but are present in different ratios (F12 mogroside V:11-O-mogroside V is 4:9, and F13 mogroside V:11-O-mogroside V is 13:3). Mogroside V was determined to be 425 times sweeter than sucrose and was extremely sweet, while 11-O-mogroside V was evaluated to be 84 times sweeter than sucrose.

[0173] Example 3 Method The Momordica grosvenori fruit extract (Extract 1 of Example 1 above) containing about 68 wt% mogroside obtained from Azile LCC (Rolling Hills Est, California) was fractionated, and the composition of each fraction was determined by the chromatography method described above for Example 1. Each fraction was combined with a 5% sucrose solution, and the flavors of three samples were compared by three expert panelists (experienced flavorists) with a 5% sucrose control.

[0174] Results Table 3 shows the chemical compositions of fractions 11 - 20 of the extract. [Table 3-1] [Table 3-2] [Table 3-3]

[0175] Table 4 shows the tasting results for fractions 12 - 15. The results are the same as those obtained in Example 2. [Table 4]

[0176] Example 4 Mogroside V and 11-O-mogroside V were isolated from the Momordica grosvenori extract using an Agilent 1100 preparative HPLC system and a Phenomenex Luna C18 (2) column (5 μm, 210X21.4 mm), and combined to form solutions of various concentrations. These solutions were combined with solutions containing 5% (w / v) sucrose and 0.03% (w / v) citric acid to give test samples, which were then evaluated by a sweetness-sensitive flavor panel of five experts (skilled flavorists).

[0177] The results are shown in Table 5 below. [Table 5]

[0178] Surprisingly, blending 11-O-mogroside V with mogroside V was found to improve the quality of sweetness compared to mogroside V alone. Adding 11-O-mogroside V to mogroside V helped reduce lingering sweetness (weakening the aftertaste of sweetness) and astringent, bitter aftertaste compared to mogroside V alone. Thus, 11-O-mogroside V produced a sweetness flavor more similar to sugar than mogroside V alone (i.e., it helps provide a temporal profile closer to sugar). This makes it possible to obtain higher sweetness using higher concentrations of mogroside V while eliminating the disadvantages associated with using higher concentrations of this sweetener (e.g., lingering, bitter, and astringent aftertaste). This was surprising considering that mogroside V is the most potent mogroside sweetener, while 11-O-mogroside V is far less potent.

[0179] Example 5 A sweetness-sensitive flavor panel ranked the sweetness of a solution of the sweetener mixture ("Mixture 1") against a wide range of sucrose concentrations to determine the sucrose equivalents. Mixture 1 was a combination of fractions 11-18 from Example 2 and contained 8.16 wt% 11-O-mogroside V and 61.6 wt% mogroside V. The results are shown in Table 6 below. [Table 6]

[0180] The data demonstrate that Mixture 1 has a sweetness of less than 1% sucrose equivalent, which is accepted by FEMA as "essentially unsweetened" (as determined by the seven panelists). Therefore, since Mixture 1 has no detectable sweetness at any of these levels, it is suitable for use as a sweetening modifier or blend at the indicated concentrations. A concentration (35 ppm) of mixture 1, which has an iso-sweetness threshold close to 1%, was selected and added to a 5% (w / v) sucrose solution. This solution was then ranked against 5%, 6%, 6.5%, and 7% (w / v) sucrose solutions. This was repeated for a 45 ppm monk fruit extract. The average score for each solution was determined. The results are shown in Table 7 below. [Table 7]

[0181] Surprisingly, the increase in sweetness of the 5% (w / v) sucrose solution to which they were added was greater than the increase in sweetness of the sweeteners alone, indicating that mixture 1 and monk fruit extract act as sweetness enhancers. The flavors of mixture 1 at various concentrations were tested by a panel of three experts (skilled flavorists) in solutions containing 5% sucrose and 0.03% citric acid. The flavors were compared to the monk fruit extract used in Example 2 (obtained by Azile LCC (Rolling Hills Est, California) (extract 1 in Example 1 above) and containing approximately 68 wt% mogrosides) (also combined with a 5% sucrose and 0.03% citric acid solution). The results are shown in Table 8.

[0182] [Table 8] In general, mixture 1 offers superior sweetness quality (less baggage, sweeter) compared to monk fruit extract.

[0183] Example 6 A sweetness-sensitive flavor panel ranked the sweetness of solutions of various sweeteners (mogroside V, mogroside IV, siamenoside, neomogroside, 11-O-mogroside V) against a wide range of sucrose concentrations to determine their sucrose equivalents. The sweeteners were obtained using an Agilent 1100 preparative HPLC system and a Phenomenex Luna C18 (2) column (5 μm, 210 x 21.4 mm). The results are shown in Tables 9-13. [Table 9]

[0184] [Table 10] [Table 11]

[0185] [Table 12] [Table 13]

[0186] The data demonstrate that mogroside V (25 ppm), mogroside IV (30 ppm), siamenoside (25 ppm), mogroside V (25 ppm) combined with 11-O-mogroside V (3 ppm), and neomogroside (30 ppm) all have a sweetness of less than 1.5% sucrose equivalent (as determined by seven panelists), which is accepted by FEMA as "essentially unsweetened." Therefore, since they do not have any detectable sweetness at these levels, these compounds and mixtures are suitable for use as sweetness modifiers at the indicated concentrations.

[0187] The sweeteners tested were selected at an isosweetness threshold close to that of a 1% solution and added to a 5% (w / v) sucrose solution. These solutions were then ranked against 5%, 6%, 6.5%, and 7% (w / v) sucrose solutions. The average score for each solution was determined. The results are shown in Table 14 below. [Table 14] Surprisingly, the increase in sweetness of the 5% (w / v) sucrose solution to which they were added was greater than that of the sweeteners alone, indicating that mogroside V, siamenoside, neomogroside, and mogroside V act as sweetness enhancers.

[0188] The flavors of these sweeteners were tested by a panel of three experts (skilled flavorists) in a solution containing 5% sucrose and 0.03% citric acid. The flavors were compared to the monk fruit extract used in Example 2 (obtained from Azile LLC (Rolling Hills Est, California) (Extract 1 in Example 1 above), and containing approximately 68 wt% mogroside). Mogroside IV, siamenoside, and neomogroside all outperformed the monk fruit extract in terms of sweetness quality when added to 5% sucrose and 0.03% citric acid. These three compounds provide a sugary flavor with less lingering sweetness. Siamenoside was described as having a "sweeter body, sweeter, slightly more rounded upfront, and rounder, lingering sweetness." Mogroside IV was described as having a "good and similar sweetness to mogroside V." Neomogroside was described as having a "sweet taste with a slightly bitter aftertaste." The results for mogroside V are shown in Table 15.

[0189] [Table 15] In general, tasters agreed that 80% Mogroside V does not have the same well-rounded sweetness profile as monk fruit extract. 80% Mogroside V has a more acidic taste when applied to sugar / acid / aqueous solutions.

[0190] Example 7 method Mogroside V, siamenoside, mogroside IV, and neomogroside were obtained using an Agilent 1100 preparative HPLC system and a Phenomenex Luna C18 (2) column (5 μm, 210 x 21.4 mm). Mogroside V, siamenoside, mogroside IV, and neomogroside were added to a solution containing 5% sucrose and 0.03% citric acid at concentrations of 25 ppm (mogroside V), 25 ppm (siamenoside), 30 ppm (mogroside IV), and 30 ppm (neomogroside), respectively. These test solutions were tasted by a panel of seven experts. Each panelist scored the test solutions in comparison to a base solution (a solution of 5% sucrose and 0.03% citric acid) for various aspects of sweetness (upfront sweetness, overall sweetness, lingering sweetness, astringency, and volatile off-taste).

[0191] A score of 0 indicates that the flavor aspect was the same, 1 indicates slightly higher, 2 indicates higher, 3 indicates much higher, -1 indicates slightly lower, -2 indicates lower, and -3 indicates much lower. The average score for each test solution was calculated for each flavor aspect. The results are shown in Table 16 below. [Table 16]

[0192] Example 8 As shown above, siamenoside, neomogroside, and mogroside IV all possess similar or superior sweetness flavor qualities compared to mogroside V with a top of 5% sucrose and 0.03% citric acid. Therefore, the flavor of 11-O-mogroside V with the flavors of each of these mogrosides is evaluated as shown in Table 17. [Table 17]

[0193] Example 9 The flavor of mogroside V with or without 11-O-mogroside V in various milk or yogurt bases is evaluated as shown in Table 18. The isoconcentration thresholds for mogroside V in milk and yogurt are also evaluated. The milk base (2% fat) contains 2% fat milk and 5% sucrose. The non-fat yogurt base contains plain non-fat yogurt and 5% sucrose. The whole-fat yogurt base contains plain whole-fat yogurt and 5% sucrose. Higher dose levels are used for milk and yogurt compositions due to fat, protein, and other components. Monk fruit extract is used at 75 ppm for these applications.

[0194] [Table 18]

[0195] Example 10 Identification of a new minor cucurbitan glycoside from Siraitia grosvenorii introduction Siraitia grosvenorii (Swingle) C. Jeffrey ex Lu et ZY Zhang is a perennial vine of the Cucurbitaceae family, native to southern China and northern Thailand. The fruit of S. grosvenorii, commonly known as "Luo Han Guo," has been used for centuries in China as a traditional medicine to treat respiratory infections, bronchitis, gastritis, constipation, and other ailments. Modern pharmacological studies have confirmed that S. grosvenorii extracts or their components possess a variety of bioactivities, including antibacterial, anti-inflammatory, anti-diabetic, anti-cancer, and immunostimulant properties.[1] Luo Han Guo is used as a sweetener in food in China. It is now one of the best known natural high-intensity sweeteners in the world. Since the discovery of cucurbitan glycoside mogroside V as the sweetness principle of S. grosvenorii, more than 40 cucurbitan triterpenoids have been reported from S. grosvenorii to date [1-4]. Researchers in the food and flavor industries are actively discovering and adding more new compounds within the mogroside pool in order to find new mogrosides with superior sweetness performance [5-7]. New molecules under the category of known natural sweeteners with superior sweetness performance are highly desired by the food and flavor industries. The commercialization of rebaudioside M (also known as rebaudioside X) is a good example. Even though it is a minor natural product from stevia (less than 0.1%) discovered in 2010, rebaudioside M has rapidly progressed to the commercialization stage thanks to cost reductions due to technological developments in plant biology, molecular biology and enzyme engineering [8, 9]. Rebaudioside M received Letter of No Objection from the US FDA in 2013, 2014, and 2017 for its Generally Recognized as Safe (GRAS) status (GRN No. 473, 512, and 667)[10-12].

[0196] We conducted a study using commercially available monk fruit extracts to find the best-performing mogroside or combination thereof

[13] . Herein, we report two novel minor cucurbitan glycosides from S. grosvenorii and highlight our novel oligosaccharide elucidation strategy based on HSQC-TOCSY experiments using different mixing times.

[0197] material and method General experimental procedure Optical rotation was measured using a Rudolph Autopol IV polarimeter. NMR spectra were recorded using a Bruker DRX Avance 300 or 500 spectrometer. Chemical shifts were given as δ (ppm) with reference to the residual solvent peak. Low-pressure chromatography was performed on a Biotage Flash system SP1. Preparative HPLC was performed on an Agilent 1100 preparative HPLC system with a Phenomenex Lunar C18(2) column (5 μm, 210 x 21.4 mm) or a TSKgel Amido-80 column (5 μm, 300 x 21.5 mm) (Tosoh Bioscience LLC). Analytical HPLC was performed on an Agilent 1100 analytical HPLC system equipped with an ESA corona CAD detector. LC-MS was performed using a Waters Q-Tof micromass spectrometer connected to a Waters 2795 separation module.

[0198] plant material I purchased monk fruit extract (product name Swingle, approximately 60% mogroside) from Blue California Co., Ltd.

[0199] instrument use Chromatographic conditions: Chromatography was performed on a Waters AcquityH UPLC. Separation was performed at 25°C using a 1.0 × 100 mm Acquity UPLC HSS T3 column (Waters) with a particle size of 1.8 mm and a 0.2 mm prefilter. Solvent A was water and solvent B was acetonitrile, both containing 0.1% formic acid. The injection volume was set to 10 μl. The chromatographic flow rate was 200 μl / min. The sample was eluted from the LC column using the following linear gradient (curve number 6): 0-40 min: 90% A - 30% A; 40-45 min: 30-10% A; 45-50 min: 10% A; 50-51 min: 10%-90% A, 51-55 min 90% A for re-equilibrium.

[0200] mass spectrometry The U-HPLC system was connected to a hybrid quadrupole orthogonal time-of-flight (TOF) mass spectrometer (SYNAPT G2 HDMS, Waters MS Technologies, Manchester, UK). The mass spectrometer was configured in positive electrospray ionization mode (ESI). + The experiment was performed using the following parameters: sample cone voltage 40, capillary voltage 0.7kV, source temperature 40°C, desolvation temperature 450°C, desolvation gas flow rate 800 L / h, and cone gas flow rate 50 L / h. Leucine enkephalin was extracted using the lockmass [M+H] at m / z 556.2771. - It was used as such. Sodium formate solution was used for external instrument calibration.

[0201] purification 3 g of monk fruit extract was dissolved in 15 mL of water and loaded onto a pre-equilibrated C-18 Snap cartridge (KP-C18-HS, ​​120 g, 132 mL column volume). The gradient system used (A: water; B: methanol) was as follows: 30% 2 CV, 30%-80% 10 CV, 80%-100% 2 CV, 100% 2 CV. The flow rate was 30 mL / min. 27 mL of each fraction was collected. A total of 12 g of monk fruit from the four loadings was fractionated. All fractions were analyzed by analytical HPLC to identify the fraction containing the target mogroside (homogeneous mobile phase: 24% acetonitrile in water; column: Luna C18 5 μm 4.6 × 150 mm). Fractions 36-38 containing iso-mogroside VI and 11-epi-mogroside V were combined and the solvent was evaporated. Further preparative HPLC purification of fractions 36-38 yielded iso-mogroside VI (1, 22 mg) and 11-epi-mogroside V (2, 17 mg) (24% acetonitrile in water, 10 mL / min, retention times 13.1 min and 14.3 min, respectively). 11-oxo-mogroside V (4) and neo-mogroside (3) were present in flash fractions 39-40, which contained 11-oxo-mogroside V as the main component. On reverse-phase C-18 preparative HPLC, neo-mogroside appeared as a tail shoulder of 11-oxo-mogroside (24% acetonitrile in water, 10 mL / min, retention times 17.0 min and 18.0 min, respectively). Peak front collection yielded 105 mg of compound 11-oxo-mogroside V(4). Further purification of the neomogroside (3, 15 mg) from the shoulder was achieved by preparative HPLC on TSKgel Amido-80 (65% acetonitrile in water, 20 mL / min, rt 15.5 min).

[0202] Iso-mogroside VI(1): White amorphous powder; [α] 20 D -8.2 (c 0.12, MeOH); 1 1H NMR and 13 For 13C spectroscopy data, see Table 1; HRESIMS: m / z 1449.7075 [M+H]ー (C 66 H113O 34 Calculated for 1447.7113, Δ2.6 ppm). Epi-mogroside V(2): White amorphous powder; [α] 20 D +4.5 (c 0.13, MeOH); 1 1H NMR and 13 For 13C spectroscopy data, see Table 1; HRESIMS: m / z 1287.6558 [M+H] ー (C 60 H 103 O 29 Calculated for 1287.6585, Δ2.1 ppm).

[0203] Determination of acid hydrolysis and the absolute configuration of sugars Compound 1 (1.2 mg) or 2 (1.8 mg) was incubated in 1 mL of 1 M HCl at 80°C for 3 hours. After hydrolysis, the solution was extracted with ELISA (1 mL x 3). The remaining aqueous solution was evaporated by blowing nitrogen gas and freeze-drying. The absolute configuration of the sugar in the residue was determined by GS-MS analysis of its O-silylated derivative and compared with the derivatives of D-glucose and L-glucose standards. Briefly, the sugar residue, D-glucose (2 mg) or L-glucose (2 mg) was dissolved in pyridine (0.5 mL). 0.1 M L-cysteine ​​methyl hydrochloride (Aldrich, Milwaukee, WI) in pyridine (0.5 mL) was added to the solution. The mixture was kept at 60°C for 2 hours and dried by blowing nitrogen gas. The residue was added with 1-trimethylsilyl imidazole (Fluka, Buchs, Switzerland) (0.5 mL) and incubated at 60°C for 1 hour. The mixture was partitioned by adding n-hexane and water (1.0 mL each). The n-hexane extract was analyzed by GC-MS under the following conditions: capillary column HP-5MS (30 m × 0.25 mm × 0.25 μm, Agilent); column temperature, 180–230°C with a 5°C / min gradient; injection temperature, 250°C; carrier, He gas; partitioning ratio, 20:1. The O-silylated derivatives of D-glucose and L-glucose showed retention times of 16.02 and 16.39 mins, respectively. By comparing the retention times and cochromatography, it was determined that the sugar residues after oxidative hydrolysis of 1 and 2 were D-glucose.

[0204] Reduction of 11-oxomogroside V using NaBH4 25 mg of 11-oxo-mogroside V(4) was dissolved in 50% dioxane, and 20 mg of NaBH4 was added. The mixture was heated at 50°C for 3 days. The reaction mixture was periodically analyzed by HPLC to monitor the progress of the reaction. After the reaction, the mixture was acidified with acetic acid and concentrated to dryness by blowing nitrogen gas. The residue was redissolved in water and passed through a pre-equilibriumized C-18 SPE column. The methanol eluent from the SPE column was concentrated. The residue was then separated by semi-preparative HPLC. The two reduction products had the same retention time and molecular weight as mogroside V and 11-epi-mogroside V isolated by LC-MS analysis and cochromatography on analytical HPLC. 1-D and 2-D NMR data also confirmed that the structures of the two reduction products were mogroside V and 11-epi-mogroside V.

[0205] Results and discussion Isolation and elucidation of iso-mogroside VI(1) and 11-epi-mogroside V(2) In the process of investigating commercially available monk fruit extracts containing 60% mogrosides by LC-MS, several mogrosides with 6 or 5 sugar moieties in the extracts attracted our attention (Figures 2 and 3). Since there were few reports on the sweetness characterization of mogroside V and VI isomers, we decided to purify and identify these isomers for our evaluation. The concentrations of 1, 2, 3, and 4 in the extract were estimated to be 0.8%, 0.5%, 0.6%, and 4.9%, respectively, according to a universal corona detector. After fractionation on a flash chromatography system and subsequent purification by preparative HPLC, the four targeted mogrosides 1–4 were purified and identified as iso-mogroside VI (1), 11-epi-mogroside V (2), neo-mogroside (3), and 11-oxo-mogroside V (4).

[0206] The molecular formula of 1, and its HR-ESI-MS spectral data ([MH] - m / z, 1447.6957, C 66 H 111 O 34Calculated for C (1447.6957) 66 H 112 O 34 This was hypothesized. The NMR spectral data of 1 suggested a hexasaccharide triterpenoid saponin structure in which 33 of the 66 carbon atoms are assigned to the triterpenoid aglycone and 36 of the 66 carbon atoms are assigned to the 6 hexose moieties. 13 C and 1 The 1H NMR spectrum showed signals for seven singlet tertiary methyl groups, doublet secondary methyl groups, and olefinic methines, suggesting a typical (24R)-cucurbita-5-ene-3β,11α,24,25-tetraol mogrol aglycone (Table 19). 1 H, 13 This was further confirmed by extensive analysis of 1C and 2D (COSY, TOCSY, HSQC, and NOESY) NMR data, as well as comparison with NMR data using the mogroside V standard.

[0207] [Table 19-1] [Table 19-2] [Table 19-3]

[0208] GC-MS analysis of the water-soluble acid hydrolysis product of 1 showed that D-glucose is the only monosaccharide in the structure of 1. The HSQC spectrum clearly showed cross-peaks of the six glucosyl anomers: Glc-I(δ C 106.8 and δ H 4.73), Glc-II(δ C 105.1 and δ H 5.10), Glc-III(δ C 103.7 and δ H 4.85), Glc-IV(δ C 104.6 and δH 4.78), Glc-V (δ C 104.7 and δ H 5.43), Glc-VI (δ C 104.8 and δ H 5.03). The stereochemistry of all six glucopyranosyls was determined to be in the β configuration from their anomeric proton coupling constants 3 J H1、H2 . From the HSQC-TOCSY experiment (hsqcgpmlph) with a mixing time of 100 ms, the signals of the glucoplanosyl carbons can be divided into six groups (Figure 4). The elucidation of the oligosaccharides started from the glucopyranosyl connected at C-3 of the cucurbitane aglycon. Glc-I was determined to be linked to the aglycon C-3 according to the HMBC correlation between its anomeric proton (δ H 4.73, d, J = 7.9 Hz) and the aglycon C-3 (δ C 87.6) and the NOESY correlation between Glc-I H-1 and the aglycon H-3. As determined by HSQC-TOCSY, the 13C signals of Glc-I (δ C 75.1, 77.8, 71.4, 77.2, 70.1) missed the typical C-6 carbon signal at approximately δ C 62. The downfield shift of Glc-I C-6 (δ C70.1) indicated glycosylation at this position. By comparing the HSQC-TOCSY spectrum (hsqcgpmlph) with increasing mixing time at 10, 30, 60, and 100 ms, it can be observed that the relay of magnetization transfer gradually expands from C-2 to C-6 (Figure 4). As shown in Figure 4, HSQC-TOCSY under a mixing time of 10 ms showed a correlation between glucopyranosyl H-1 and C-2. Under a mixing time of 30 ms, a correlation between H-1 and C-3 appeared in addition to the correlation between H-1 and C-2. Under 60 ms, the carbon chain expands to C-4 as indicated by the HSQC-TOCSY correlation. A complete HSQC-TOCSY correlation of H-1 with C-2~C-6 can be observed under 100 ms. Thus, the signals from C-2~C-6 can be uniquely assigned. The linkage of Glc-II to Glc-I is performed using the anomer Glc-II H-1(δ H Glc-I C-6(δ C 70.1) This was established by the correlation of HMBC with Glc-II. 13 C signal (δ C The results for 75.0, 77.8, 71.5, 78.0, and 62.5 suggested the absence of glycosylation on Glc-II. As a result, the sugar chain on aglycone C-3 was supplied as 3-O-(β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl).

[0209] Anomeric proton (δ H 4.85, d, J=7.5Hz) Aglycone carbon signal (δ C The HMBC correlation to 92.3) indicated a connection to the aglycone C-24 of Glc-III H-1. 13 C pattern (δ C The values ​​81.6, 78.3, 71.4, 76.4, and 70.0 suggested C-2 and C-6 glycosylation shifts. Analysis of HSQC-TOCSY with mixing times of 10, 30, 60, and 100 ms yielded sequential assignment and confirmation of C-2 and C-6 low-field shifts. Glc-IV was identified as having its H-1 (δ H4.78, d, J=7.5Hz) Glc-III C-6(δ C Based on the HMBC correlation with 70.0), it was determined that it connects to C-6 of Glc-III. Glc-IV was a typical terminal glucopyranosyl without any substitutions (δ C 74.5, 77.7, 71.2, 78.2, 62.4). The coupling of Glc-V to Glc-III's C-2, and the anomaly Glc-V H-1 (δ H Glc-III C-2(δ C This was established by the correlation of HMBC to 81.6). Glc-V H-1(δ H The relative low-field shift of 5.43) was consistent with previous reports that it has a similar structure. C C-4 in 70-71 13 C chemical shift, Glc-V signal set (δ C It was not found in 104.7, 75.4, 76.4, 82.0, 76.5, 62.6), suggesting glycosylation at C-4. By observing the relay of C-2 to C-6 from HSQC-TOCSY with mixing times of 10, 30, 60 and 100 ms, δ C 82.0 was clearly assigned to C-4 of Glc-V (Figure 4). Glc-V C-4 (δ C 82.0) and Glc-VI's H-1(δ H HMBC cross-peak analysis between (5.03, d, J=7.7Hz) further confirmed that Glc-VI is linked to Glc-V at this position. Glc-VI was a terminal glucopyranosyl without further sugar branching. Based on the above evidence, the structure of iso-mogroside(1) was assigned as 3-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl-mogrol-24-O-β-D-glucopyranosyl-(1→6-[β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl.

[0210] Compound 2 has the following HR-ESI-MS data ([MH] - (m / z, 1285.6429) Molecular formula C 60 H102 O 29 We assigned it. The NMR data of the oligosaccharide portion of 2 could be superimposed with those of mogroside V. Detailed 2-D NMR experiments including HSQC, HMBC, NOESY, COSY, and HSQC-TOCSY confirmed that 2 has the same sugar portion as mogroside V. Next, we turned our attention to the aglycone NMR data. The HMBC correlation between C-11 and H3-19 was found to be similar to that of mogroside V (δ C 77.8) Compared to the C-11 (δ C A significant high-field shift was revealed in compound 2.5). Further assignment of aglycone data by 2-D NMR experiments showed that major 13C chemical shift changes occur for C-8, C-10, and C-12 when compared with data for mogroside V (Table 19). This suggested that C-11 is β-OH instead of α-OH. The stereostructure of the β-OH of compound 2 was further established by NOE correlations with H-8 and H3-18, 19; H-10 and H3-28, H3-30; H-11 and H3-30; H-17 and H3-30. Some natural 11-β-OH cucurbitans and some semi-synthetic 11-β-OH cucurbitans have been previously reported [14, 15]. 13 The 13C NMR data were in good agreement with the data for the semi-synthetic 11-β-OH cucurbitan glycoside recorded with pyridine-d6

[14] . Matsuda et al. 13¹¹C NMR data were obtained at methanol-d4 and were quite different in terms of chemical shifts at C-11, C-8, C-10 and C-12

[15] . To confirm the 11-β-OH structure of 2, a semisynthesis of 2 was carried out by chemical reduction of 11-oxo-mogroside V(4) to the 11-β-OH and 11-α-OH isomers of mogroside V. By LC-MS, HPLC cochromatography and NMR data analysis, the semisynthesized 11-epi-mogroside V was determined to be identical to the isolated 11-epi-mogroside V. Therefore, we determined the structure of 11-epi-mogroside V(2) to be 3-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl-11β-OH-mogrool-24-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranosyl. To our knowledge, this is the first reported natural mogroside containing an 11-β hydroxyl group.

[0211] HSQC-TOCSY with various mixing times for elucidating oligosaccharide chains. Gheysen et al. investigated TOCSY with various mixing times and concluded that 100 ms was the optimal spinlock time for distinguishing between D-glucose, D-galactose, and D-mannose

[16] . Through their results, we found that spinlock time can significantly affect the magnetization transfer efficiency of H-1 in D-glucose. The correlation between H-1 and H-2 through H-6 gradually expanded to H-6 as the spinlock time increased. Motivated by these investigations, we hypothesized that by increasing the spinlock time of HSQC-TOCSY, we should find that the correlation between glucose H-1 and C-2~C-6 gradually expands from C-2 to C-6 as the chain of magnetization transfer expands. HSQC-TOCSY with increased spinlock time provides carbon sequence information, which would be extremely useful for elucidating and assigning oligosaccharides. Figure 4 shows the HSQC-TOCSY (hsqcgpmlph) spectra of iso-mogroside VI with mixing times of 10, 30, 60, and 100 ms. The cross-peaks in Figure 4 were quantified by their integration and compared in Figure 5. Peak intensities (as presented in the integration) may, in some cases, be indicators of their distance from H-1. For example, under experiments with a mixing time of 30 ms, all C-3 peaks are significantly weaker than the C-2 peaks. However, under 60 ms, the C-3 peaks are stronger than the C-2 peaks. To ensure a correct understanding, the carbon sequence should be determined not only by the peak intensity at a given mixing time, but also by an overview of all HSQC-TOCSY spectra with various mixing times.

[0212] Traditionally, the NMR elucidation and assignment of saponin sugar chains begins with the sugar linked to the aglycone. H-1 and C-1 signals of well-separated anomerics can be identified by HMBC or NOESY. Then, COSY correlation and... 3The proton signal of a monosaccharide can be assigned through the agreement of the J(H,H) bond constant. Since a large bond constant (>7Hz) typically indicates two adjacent axial CH bonds, and a small bond constant (<4Hz) indicates an axial-equatorial or equatorial-equatorial CH bond, the type of monosaccharide can be determined. NOE correlation is useful for confirming axial-axial, axial-equatorial, or equatorial-equatorial relationships in stereochemistry. The carbon signals (C-2 to C-6) of a sugar are assigned according to HSQC or HMQC. Because the patterns of chemical shifts of C-1 to C-6 for different types of monosaccharides are characteristic and consistent, the chemical shifts of the carbon signals as determined by HSQC / HMQC are crucial information for determining the monosaccharide type. The glycosylation site on the sugar chain can be identified through findings of changes in the chemical shifts of the carbons and can be further confirmed by HMBC correlation. In summary, existing methods for elucidating saponin sugars are HMBC → C-1, H-1 → COSY → H-2~H-6 → HSQC / HMQC → C-2~C-6, which are then supported and confirmed by binding constant analysis and NOESY experiments.

[0213] 1 H- 1 H TOCSY (Total Correlated Spectroscopy, also known as HOHAHA-Homonuclear Hartmann-Hahn) experiments can be a great help in separating complex glycoproton signals into groups. The transfer of magnetization between TOCSY spin locks from H-1 of the anomer to the end of the furanose or pyranose ring is intervening. 3The J(H,H) scalar coupling constant will depend on the magnitude of the coupling constant. Adjacent axial-axial protons with large coupling constants (>7Hz) will allow for rapid magnetization transfer, while axial-axial or equatorial-equatorial protons with small coupling constants (<4Hz) will significantly reduce transfer efficiency. Therefore, TOCSY experiments can be used not only to group proton signals into spin systems but also to provide stereochemical information about sugars. For example, we can observe the magnetization relay of glucose through H-1 to H-6 at appropriate mixing times. For galactose, even with a mixing time of 200ms, there is no magnetization relay beyond H-4.

[0214] However, in the case of mogrosides with 5 or 6 sets of glucopyranosyl signals, using COSY and TOCSY for H-1 to H-6 linking can be very clever. The proton signals of mogroside glucopyranosyl have very similar chemical shifts, and δ H They appear crowded together in a small range from 3.8 to 4.5. Clearly identifying COSY linkages through such poorly separated proton signals is difficult. The glucopyranosyl carbon signals are also very close together, and the HSQC cross peaks overlap each other to a great extent, which makes deciphering and assigning them even more difficult.

[0215] To date, HSQC-TOCSY has been applied to the elucidation and assignment of saponin structures by grouping carbon signals together into their respective spin systems [17, 18]. Through our investigation, we demonstrate for the first time that signal sequences within glucopyranosyl carbon groups can be identified by applying various mixing times in HSQC-TOCSY experiments.

[0216] Figure 6 summarizes a novel HSQC-TOCSY-based strategy for elucidating the glucopyranosyl oligosaccharide chains of mogrosides, as follows: In Step 1, heteronuclear multi-bond correlation spectroscopy (HMBC) was used to determine C-1 and H-1 of the sugar anomer, starting with the sugar linked to the aglycone. In Step 2, HSQC-TOCSY was used with a mixing time of 100 ms to determine all groups from C-2 to C-6. Assign HSQC-COSY or HSQC-TOCSY (d9=10 ms) to C-2. Assign HSQC-TOCSY (d9=30 ms) to C-3. Assign HSQC-TOCSY (d9=60 ms) to C-4. Assign HSQC-TOCSY (d9=100 ms) to C-5 and C-6. In step 3, if a C-2 downshift from approximately δ75 to approximately δ81, a C-4 downshift from approximately δ71 to approximately δ81, or a C-6 downshift from approximately δ62 to approximately δ69 is observed, confirm HMBC for glycosylation at these positions**. If a C-2 downshift from approximately δ75 to approximately δ81, a C-4 downshift from approximately δ71 to approximately δ81, or a C-6 downshift from approximately δ62 to approximately δ69 is observed, confirm HMBC for glycosylation at these positions**. 1 H bond constant and 13 1-D NMR data, such as 13C carbon signal patterns, and 2-D NMR experiments such as NOESY, HMBC, TOCSY, COSY, and HSQC can support the process and confirm the results. The novel HSQC-TOCSY-based strategy will provide a simple, rapid, and unambiguous method for elucidating and assigning the glucopyranosyl chain of any novel or known mogroside. The strategy may also be applicable for elucidating and assigning other monosaccharides and oligosaccharides.

[0217] Structures of neomogroside and mogroside VI Compound 3 was identified as a neomogroside by extensive 1-D and 2-D NMR analysis, as well as comparison with literature data

[19] . To elucidate the three oligosaccharide chains, the signals were assigned by HSQC-TOCSY and TOCSY experiments with different mixing times of 10, 30, 60, and 100 ms. The linkage of the six sugars was determined by their NOESY and HMBC correlations. The oligosaccharide chain on C-3 of the aglycone can be clearly assigned as β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl. The glucopyranosyl on C-24 of the aglycone branched at β-D-glucopyranosyl-(1→2) and β-D-glucopyranosyl-(1→6).

[0218] Neomogroside was first discovered in S. grosvenorii and described by Si et al.

[19] . A search for neomogroside in Scifinder returned CAS number 189307-15-1. However, despite the referenced literature by Scifinder being a 1996 paper by Si et al., an incorrect structure of neomogroside was given to Scifinder. The incorrect structure of 189307-15-1 was given in Scifinder as 3-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranosyl-mogrool-24-O-β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl (structure 6 in Figure 2). The report by Si et al. on neomogroside was written in Chinese and published in a Chinese journal in 1996. The availability and misinterpretation of this paper likely led to the incorrect structure in SciFinder.

[0219] In Scifinder, neomogroside and mogroside VI had the same CAS number 189307-15-1 and the same structure. Takemoto et al. first reported mogroside VI from S. grosvenorii [2]. However, C 66 H 112 O34 The molecular formula of pure mogroside was used as a reference, but the structure was not determined.[2] Prakash et al. reported the structure and NMR data of mogroside VI as a known compound in their paper published in 2011.[6] In their paper, the structure of mogroside VI was assigned as structure 6 in Figure 2. Prakash stated that the structure of mogroside VI was elucidated by NMR analysis and also by comparison with literature values. However, no citations were given for the literature values.

[0220] For known compounds, comparing NMR data with literature data can be useful for determining the structure. However, the complexity of NMR data for mogrosides makes it difficult to determine their structure primarily by comparing NMR data with literature data. 1 The 1H NMR data showed variations due to the different NMR solvents used (the ratio of pyridine and D2O can cause signal shifts) or simply due to inaccurate assignments.

[0221] 13 The 13C NMR data is very consistent, and 1 Although it has better resolution than 1H NMR data, the structural determination of oligosaccharide chains of known mogrosides is still possible. 13 It is not possible to rely on a direct comparison of 1C NMR data and literature data. Considering the case of neomogrosides, if Glu-VI glucopyranosyl-(1→2) branches on Glu-I, Glu-II, Glu-III, Glu-IV, or GluV, the five isomers are very similar. 13 It will have 13C NMR data. Before the oligosaccharide chain of the mogroside can be uniquely determined, 13 Rather than comparing 13C NMR data with literature data, extensive 2-D NMR analysis should be carefully performed.

[0222] Example 11 Sweetness intensity of iso-mogroside VI and 11-epi-mogroside V method 10 mg of iso-mogroside VI (Figure 7) was dissolved in 31 mL of water to prepare a 100 ppm iso-mogroside VI solution. The concentration of 11-epi-mogroside V (Figure 8) used was 374 ppm (9.34 mg of 11-epi-mogroside V in 25 mL of water). A series of standard sucrose solutions were prepared as sweetness references (0.50%, 0.75%, 1.00%, 1.25%, 1.50%).

[0223] result Four sweetness-sensitive panelists were asked to evaluate 100 ppm iso-mogroside VI and 374 ppm 11-epi-mogroside V and sucrose standards, and to provide sweetness equivalent concentrations relative to sucrose. The average sweetness equivalent concentration of each compound was used to calculate the iso-mogroside efficacy. The iso-mogroside efficacy values ​​for iso-mogroside VI and 11-epi-mogroside V were determined to be 91 times and 35 times the sweetness of sucrose, respectively (100 ppm iso-mogroside VI sweetness equivalent to 0.91% sucrose; 374 ppm 11-epi-mogroside V sweetness equivalent to 1.31% sucrose).

[0224] Example 12 method Iso-mogroside VI and 11-epi-mogroside V were obtained as described in Example 10. Iso-mogroside VI and 11-epi-mogroside V were added to solutions containing 5% sucrose and 0.03% citric acid at a concentration of 25 ppm each. These test solutions were tasted by a panel of seven experts. Each panelist scored the test solution in comparison to the base solution (solution of 5% sucrose and 0.03% citric acid) for various aspects of sweetness (overall sweetness, upfront sweetness, lingering sweetness, astringency, and volatile off-notes). A score of 0 indicates that the aspects of flavor were the same, 1 indicates slightly higher, 2 indicates higher, 3 indicates very high, -1 indicates slightly lower, -2 indicates lower, and -3 indicates very low.

[0225] result The average score for each test solution was calculated for each flavor aspect. The results are shown in Table 20 below. [Table 20]

[0226] Two novel minor cucurbitan glycosides, along with known 11-oxomogrosides and neomogrosides, were purified from a commercially available extract of monk fruit (Siraitia grosvenorii (Swingle) C. Jeffrey ex Lu et ZY Zhang). Extensive NMR and LC-MS analysis, as well as chemical synthesis, revealed the structures of the two novel compounds, isomogroside VI(1) and 11-epimogroside V(2), respectively: 3-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl-mogrool-24-O-(β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl The compounds were identified as sil-(1→2)]-β-D-glucopyranosyl and 3-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl-11β-OH-mogrol-24-O-β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl. The sweetness effects of iso-mogroside VI and 11-epi-mogroside V were determined by each of the following factors. The sweetness was evaluated as 91 times and 35 times that of clout (100 ppm iso-mogroside VI, equivalent in sweetness to 0.91% sucrose; 374 ppm 11-epi-mogroside V, equivalent in sweetness to 1.31% sucrose). Through our process of identifying novel and known mogrosides with 5 or 6 glucopyranosyls, a new strategy for elucidating and assigning glucopyranosyl glycans was developed. The new strategy, based on HSQC-TOCSY experiments with various mixing times, characterized rapid and unambiguous elucidation and assignment of glucopyranosyl oligosaccharides. The previous confusion regarding the structures of neomogroside and mogroside VI was re-examined and clarified after confirmation of the structure of neomogroside by our extensive NMR spectral analysis.

[0227] Example 13 A carbonated soft drink having a composition containing Reb M, glucosylated steviol glycoside, and a taste modifier, with 30% to 100% sugar replacement. Carbonated soft drinks were prepared according to Table 21 below and evaluated by experienced flavorists for their sweetness characteristics and mouthfeel. [Table 21-1] [Table 21-2]

[0228] [Table 22]

[0229] Example 14 A non-carbonated apple beverage having a composition containing Reb M, glucosylated steviol glycoside, and a taste modifier, with 50% and 80% sugar replacement. Non-carbonated apple beverages were prepared according to Table 23 below and evaluated by experienced flavorists for their sweetness characteristics and mouthfeel. [Table 23-1] [Table 23-2]

[0230] [Table 24]

[0231] Example 15 A strawberry milk beverage having a composition containing Reb M, glucosylated steviol glycoside, and a taste modifier, with 50% and 100% sugar replacement. Strawberry milk beverages were prepared according to Table 25 below and evaluated by experienced flavorists for their sweetness characteristics and mouthfeel. [Table 25]

[0232] [Table 26]

[0233] Example 16 Strawberry yogurt having a composition containing Reb M, glucosylated steviol glycoside, and a taste modifier, with 50% and 70% sugar replacement. Strawberry yogurt samples were prepared according to Table 27 below and evaluated by experienced flavorists for their sweetness characteristics and mouthfeel. [Table 27]

[0234] [Table 28]

[0235] The above broadly describes certain aspects of the present invention without limitation. Modifications and alterations that would be readily apparent to those skilled in the art are intended to be within the scope of the present invention as defined in and as provided for in the appended claims.

[0236] reference [ka] [ka]

Claims

1. (i) Rebaudioside M, (ii) Glucosylated steviol glycosides selected from glucosylated stevioside, glucosylated rebaudioside B, glucosylated rebaudioside C, glucosylated rebaudioside D, glucosylated rebaudioside E, glucosylated rebaudioside F, glucosylated rebaudioside G, glucosylated rebaudioside H, glucosylated rebaudioside I, glucosylated rebaudioside J, glucosylated rebaudioside K, glucosylated rebaudioside L, glucosylated rebaudioside M, glucosylated rebaudioside N, glucosylated rebaudioside O, glucosylated dulcoside A, glucosylated dulcoside B, glucosylated rubusoside and mixtures thereof, and (iii) From 500 ppm to 4000 ppm, Betaine; The carboxylic acid-amino acid conjugate represented by the following formula 【Chemistry 1】 During the ceremony R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; The carboxylic acid-amino acid conjugate represented by the following formula 【Chemistry 2】 During the ceremony R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; The carboxylic acid-amino acid conjugate represented by the following formula 【Transformation 3】 In the formula R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; 4-(2,2,3-trimethylcyclopentyl)butanoic acid; Chlorogenic acid; and Compound defined by the following formula I 【Chemistry 4】 R １ is H, methyl, or ethyl; R ２ is H, OH, fluorine, C １ -C ４ a linear or branched alkyl, C １ -C ６ an alkoxy (where the alkyl group is linear or branched), or C ３ -C ５ a cycloalkyl moiety: R ３ is H, methoxy, methyl, or ethyl; Or R ２ and R ３ Together with them, between the phenyl carbon atoms to which they are bonded, the bridging portion -O-CH ２ Forms -O-; R ４ is OH or methoxy; and R ５ and R ６ is independently H or methyl; R １ , R ２ , R ３ , R ４ , R ５ and R ６ The following applies: (i) R ２ and R ３ Together, they form a bridge between the phenyl carbon atoms to which they are bonded, -O-CH ２ When forming -O-, R １ , R ５ , R ６ H is H, and R ４ is OH, and (ii) R ４ is OH, and R １ ~R ３ When H, R ５ , R ６ At least one of them is methyl. Taste modifiers selected from, A composition that imparts sweetness, wherein the ratio of rebaudioside M to glucosylated steviol glycoside present in the sweetening composition is from about 1:1 to about 1:1.

5.

2. The composition according to claim 1, wherein the ratio of rebaudioside M to glucosylated steviol glycoside in the sweetening composition is selected from the group consisting of 1:1.1, 1:1.2, 1:1.3, 1:1.4, and 1:1.

5.

3. The composition according to claim 2, wherein the ratio of rebaudioside M to glucosylated steviol glycoside in the sweetening composition is 1:1.

2.

4. A composition that imparts sweetness improves each of the sweetness characteristics (one or more) of the sweetened composition compared to one or more sweetness characteristics (one or more) of the sweetened composition in the absence of the sweetened composition. Here, the improvement in sweetness characteristics is To enhance the sweetness intensity, To reduce the lingering sweetness, To improve the sweetness of the upfront, To reduce the bitter off-note flavor, To reduce the dry and / or astringent taste, The composition according to claim 1.

5. The composition according to claim 4, wherein the sweetening composition improves the upfront sweetness of the sweetened composition compared to the upfront sweetness of the sweetened composition in the absence of the sweetening composition.

6. The composition according to claim 1, wherein the sweetening composition weakens the bitter off-note flavor of the sweetened composition compared to the bitter off-note flavor of the sweetened composition in the absence of the sweetening composition.

7. The composition according to claim 1, wherein the sweetening composition reduces the dry and / or astringent taste of the sweetened composition compared to the dry and / or astringent taste of the sweetened composition in the absence of the sweetening composition.

8. At least one sweetener, and (i) Rebaudioside M, (ii) Glucosylated steviol glycoside, and (iii) 500 ppm to 4000 ppm, Betaine; The carboxylic acid-amino acid conjugate represented by the following formula 【Transformation 5】 During the ceremony R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; The carboxylic acid-amino acid conjugate represented by the following formula 【Transformation 6】 During the ceremony R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; The carboxylic acid-amino acid conjugate represented by the following formula 【Transformation 7】 In the formula R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; 4-(2,2,3-trimethylcyclopentyl)butanoic acid; Chlorogenic acid; and Compound defined by the following formula I 【Transformation 8】 R １ is H, methyl, or ethyl; R ２ H, OH, fluorine, C １ -C ４ Linear or branched alkyl, C １ -C ６ Alkoxy (where the alkyl group is linear or branched), or C ３ -C ５ This is the cycloalkyl portion: R ３ is H, methoxy, methyl, or ethyl; Or R ２ and R ３ Together with them, between the phenyl carbon atoms to which they are bonded, the bridging portion -O-CH ２ Forms -O-; R ４ is OH or methoxy; and R ５ and R ６ is independently H or methyl; R １ , R ２ , R ３ , R ４ , R ５ and R ６ The following applies: (i) R ２ and R ３ Together, they form a bridge between the phenyl carbon atoms to which they are bonded, -O-CH ２ When forming -O-, R １ , R ５ , R ６ H is H, and R ４ is OH, and (ii) R ４ is OH, and R １ ~R ３ When H, R ５ , R ６ At least one of them is methyl. A composition containing a taste modifier selected from, A composition that contains sweetness, Here, the ratio of rebaudioside M to glucosylated steviol glycoside in the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier is from about 1:1 to about 1:1.

5. The aforementioned composition having been given the sweetness.

9. The sweetened composition according to claim 8, wherein the ratio of the rebaudioside M to the glucosylated steviol glycoside in the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier is selected from the group consisting of 1:1.1, 1:1.2, 1:1.3, 1:1.4, and 1:1.

5.

10. The sweetened composition according to claim 9, wherein the ratio of the rebaudioside M to the glucosylated steviol glycoside in the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier is 1:1.

2.

11. Glucosylated steviol glycosides include glucosylated stevioside, glucosylated rebaudioside A, glucosylated rebaudioside B, glucosylated rebaudioside C, glucosylated rebaudioside D, glucosylated rebaudioside E, glucosylated rebaudioside F, glucosylated rebaudioside G, glucosylated rebaudioside H, and glucosylated rebaudioside. A sweetened composition according to claim 8, selected from the group consisting of side I, glucosylated rebaudioside J, glucosylated rebaudioside K, glucosylated rebaudioside L, glucosylated rebaudioside M, glucosylated rebaudioside N, glucosylated rebaudioside O, glucosylated dulcoside A, glucosylated dulcoside B, and glucosylated rubusoside.

12. A composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier improves one or more sweetness characteristics of a sweetened composition in the absence of the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier, by comparing each of these sweetness characteristics (one or more) of the sweetened composition with one or more sweetness characteristics of the sweetened composition in the absence of the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier. Here, the improvement in sweetness characteristics is To enhance the sweetness intensity, To reduce the lingering sweetness, To improve the sweetness of the upfront, To reduce the bitter off-note flavor; and / or To reduce the dry and / or astringent taste, That is, The sweetened composition according to claim 8.

13. The sweetened composition according to claim 12, wherein a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier improves the upfront sweetness of the sweetened composition compared to the upfront sweetness of the sweetened composition in the absence of the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier.

14. The sweetened composition according to claim 8, wherein a composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier reduces the dry and / or astringent taste of the sweetened composition compared to the dry and / or astringent taste of the sweetened composition in the absence of the composition comprising (i) rebaudioside M, (ii) glucosylated steviol glycoside, and (iii) a taste modifier.

15. The sweetened composition according to claim 8, wherein at least one sweetener is selected from the group consisting of sucrose, fructose, glucose, xylose, arabinose, rhamnose, sugar alcohols, starch syrup, and mixtures thereof.

16. The sweetened composition according to claim 15, wherein the sugar alcohol is selected from the group consisting of erythritol, xylitol, mannitol, sorbitol, and inositol.

17. A method for enhancing the sweetness of a composition that has been sweetened, To provide a base composition containing at least one sweetener in an amount equal to or exceeding the sweetness recognition threshold of the sweetener, and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, and (i) Rebaudioside M, (ii) Glucosylated steviol glycoside, and (iii) 500 ppm to 4000 ppm, Betaine; The carboxylic acid-amino acid conjugate represented by the following formula 【Chemistry 9】 During the ceremony R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; The carboxylic acid-amino acid conjugate represented by the following formula 【Chemistry 10】 During the ceremony R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; The carboxylic acid-amino acid conjugate represented by the following formula 【Chemistry 11】 In the formula R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; 4-(2,2,3-trimethylcyclopentyl)butanoic acid; Chlorogenic acid; and Compound defined by the following formula I 【Chemistry 12】 R １ is H, methyl, or ethyl; R ２ is H, OH, fluorine, C １ -C ４ a straight-chain or branched alkyl, C １ -C ６ an alkoxy (where the alkyl group is straight-chain or branched), or C ３ -C ５ a cycloalkyl moiety: R ３ is H, methoxy, methyl, or ethyl; Or R ２ and R ３ Together with them, between the phenyl carbon atoms to which they are bonded, the bridging portion -O-CH ２ Forms -O-; R ４ is OH or methoxy; and R ５ and R ６ is independently H or methyl; R １ , R ２ , R ３ , R ４ , R ５ and R ６ The following applies: (i) R ２ and R ３ Together, they form a bridge between the phenyl carbon atoms to which they are bonded, -O-CH ２ When forming -O-, R １ , R ５ , R ６ H is H, and R ４ is OH, and (ii) R ４ is OH, and R １ ~R ３ When H, R ５ , R ６ At least one of them is methyl. A composition comprising a taste-modifying substance selected from, wherein the ratio of rebaudioside M to glucosylated steviol glycoside present in the composition is approximately 1:1 to approximately 1:1.5, is added to the base composition. The method, including the method described above.

18. A method for reducing the amount of sugar in a composition that has been sweetened, To provide a base composition containing at least one sweetener in an amount equal to or exceeding the sweetness recognition threshold of the sweetener, and / or having a sweetness equivalent to or greater than about 1.5% (w / v) sucrose equivalent, and (i) Rebaudioside M, (ii) Glucosylated steviol glycoside, and (iii) 500 ppm to 4000 ppm Betaine; The carboxylic acid-amino acid conjugate represented by the following formula 【Chemistry 13】 During the ceremony R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; The carboxylic acid-amino acid conjugate represented by the following formula 【Chemistry 14】 During the ceremony R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; The carboxylic acid-amino acid conjugate represented by the following formula 【Chemistry 15】 In the formula R １ R is an alkyl residue having 6 to 30 carbon atoms, or an alkene residue containing 9 to 25 carbon atoms including 1 to 6 double bonds. １ The carbonyl group attached to it is a carboxylic acid residue, and m is 0 or 1; 4-(2,2,3-trimethylcyclopentyl)butanoic acid; Chlorogenic acid; and Compound defined by the following formula I 【Chemistry 16】 R １ is H, methyl, or ethyl; R ２ H, OH, fluorine, C １ -C ４ Linear or branched alkyl, C １ -C ６ Alkoxy (where the alkyl group is linear or branched), or C ３ -C ５ This is the cycloalkyl portion: R ３ is H, methoxy, methyl, or ethyl; Or R ２ and R ３ Together with them, between the phenyl carbon atoms to which they are bonded, the bridging portion -O-CH ２ Forms -O-; R ４ is OH or methoxy; and R ５ and R ６ is independently H or methyl; R １ , R ２ , R ３ , R ４ , R ５ and R ６ The following applies: (i) R ２ and R ３ Together, they form a bridge between the phenyl carbon atoms to which they are bonded, -O-CH ２ When forming -O-, R １ , R ５ , R ６ H is H, and R ４ is OH, and (ii) R ４ is OH, and R １ ~R ３ When H, R ５ , R ６ At least one of them is methyl. A composition comprising a taste-modifying substance selected from, wherein the ratio of rebaudioside M to glucosylated steviol glycoside present in the composition is approximately 1:1 to approximately 1:1.5, is added to the base composition. The method, including the method described above.

19. The method according to claim 18, wherein the amount of replaced sugar in the sweetened composition is from about 30 percent to about 100 percent.

20. The method according to claim 19, wherein the amount of replaced sugar in the sweetened composition is from about 30 percent to about 70 percent.

21. The method according to claim 19, wherein the amount of replaced sugar in the sweetened composition is from about 50 percent to about 100 percent.

22. The method according to claim 21, wherein the amount of replaced sugar in the sweetened composition is from about 50 percent to about 80 percent.

23. The method according to claim 22, wherein the amount of replaced sugar in the sweetened composition is about 50 percent to about 70 percent.

24. The composition according to claim 1, wherein the glucosylated steviol glycoside comprises a blend of at least one glucosylated steviol glycoside and at least one residual steviol glycoside selected from the group consisting of stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside I, rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, dulcoside B, rubusoside and combinations thereof.

25. The sweetened composition according to claim 11, wherein the glucosylated steviol glycoside comprises a blend of at least one glucosylated steviol glycoside and at least one residual steviol glycoside selected from the group consisting of stevioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, rebaudioside I, rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M, rebaudioside N, rebaudioside O, dulcoside A, dulcoside B, rubusoside and combinations thereof.

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