Method for purifying polymethoxylated flavonoids and compositions obtained therefrom

Abstract

The present disclosure generally relates to a method for obtaining a naturally derived composition rich in polymethoxylated flavonoids (PMF). In some embodiments, the method results in a composition in which PMF constitutes at least 90% by weight of the flavonoid content in the composition, based on the total weight of the flavonoids in the composition. In certain aspects, the present disclosure provides compositions obtained from the present purification method and uses of such compositions to reduce the bitter, astringent or sour taste, or to enhance the sweetness or texture of ingestible compositions, such as flavored food or beverage products. In some embodiments, the present disclosure provides uses of the resulting compositions to reduce the unpleasant taste of limonin, nomilin, or one or more thereof, which may be present at high levels in certain citrus products.

Description

[Technical field]

[0001] The present disclosure generally relates to a method for obtaining a naturally derived composition rich in polymethoxylated flavonoids (PMF). In some embodiments, the method results in a composition in which PMF constitutes at least 90% by weight of the flavonoid content in the composition, based on the total weight of the flavonoids in the composition. In certain aspects, the present disclosure provides compositions obtained from the present purification method and uses of such compositions to reduce the bitter, astringent or sour taste, or to enhance the sweetness or texture of ingestible compositions, such as flavored food or beverage products. In some embodiments, the present disclosure provides uses of the resulting compositions to reduce the unpleasant taste of limonin, nomilin, or one or more thereof, which may be present at high levels in certain citrus products.

[0002] 2. Description of Related Art The taste system provides sensory information about the chemical composition of the outside world. Gustatory transduction is one of the more sophisticated forms of chemically triggered sensation in animals. Taste signaling is found throughout the animal kingdom, from the simplest metazoans to the most complex of vertebrates. Mammals are thought to have five basic taste modalities: sweet, bitter, sour, salty and umami.

[0003] Polymethoxylated flavonoids (PMFs) are a class of compounds that occur naturally in many citrus fruits. Such compounds have a wide range of applications. For example, PMFs may provide many benefits for health and wellness. These compounds can also be used to have specific beneficial effects on the taste of other products. For example, WO 2020 / 025639 describes, among other things, the use of certain PMFs to enhance sweetness. As another example, WO 2020 / 074436 describes, among other things, the use of certain PMFs as texture enhancers and bitterness maskers.

[0004] Extracting such compounds in substantially pure form from citrus fruits is a laborious and expensive process. Producing such compounds by enzymatic conversion from other more readily available compounds in citrus fruits faces the same limitations. Thus, the use of PMFs may be cost-prohibitive for certain applications.

[0005] Alternatively, one may attempt to extract blends of flavonoids from citrus fruits, however, such methods, while offering improvements in terms of cost-effectiveness, result in compositions containing unacceptably high concentrations of certain flavonoids that impart a taste that consumers generally find unpleasant.

[0006] Therefore, there is a continuing need to develop cost-effective methods to obtain PMF without the concomitant yield of other undesirable flavonoids.

[0007] overview The present disclosure relates to the discovery of methods to obtain blends of PMF from natural products with concomitant low levels of other flavonoids that impart flavors that consumers generally find unpleasant.

[0008] In a first aspect, the disclosure provides a method for concentrating polymethoxylated flavonoids, the method comprising the steps of: (a) providing an organic oil comprising polymethoxylated flavonoids and hydroxyl-substituted flavonoids, wherein a concentration of polymethoxylated flavonoids in the organic oil is 30% by weight or less, based on a total weight of the organic oil; and (b) introducing an extraction medium into the organic oil to form a mixture having an aqueous phase and an organic phase, the extraction medium being water and C. 1~6 (c) separating at least a portion of the aqueous phase from the organic phase; and (d) producing two or more fractions of the separated aqueous phase using adsorption chromatography, wherein at least one of the two or more fractions comprises a concentration of polymethoxylated flavonoids of at least 85% by weight on a dry weight basis.

[0009] In a second aspect, the present disclosure provides a taste-modifying composition comprising one or more polymethoxylated flavonoids and one or more hydroxyl-substituted flavonoids. In some embodiments, the composition comprises a polymethoxylated flavonoid at a concentration of at least 85% by weight on a dry weight basis, or both a polymethoxylated flavonoid and a hydroxyl-substituted flavonoid. In some embodiments, the weight ratio of the polymethoxylated flavonoid to the hydroxyl-substituted flavonoid in the composition is at least 9:1. In certain related aspects, the taste-modifying composition is the product of the method of the first aspect or any embodiment thereof.

[0010] In a third aspect, the present disclosure provides the use of the taste-modifying composition of the second aspect and the related aspects above to reduce the bitterness of an ingestible composition. In certain related aspects, the present disclosure provides a method for reducing the bitterness of an ingestible composition, comprising introducing the taste-modifying composition of the second aspect and the related aspects above into the ingestible composition. In some embodiments, the ingestible composition comprises one or more bitter compounds. In some embodiments, the one or more bitter compounds comprise limonoids, such as limonin, nomilin, nomilic acid, or any combination thereof. In some embodiments, the one or more bitter compounds comprise naringin.

[0011] In a fourth aspect, the present disclosure provides the use of the taste-modifying composition of the second aspect and the related aspects above to reduce the astringency of an ingestible composition.In certain related aspects, the present disclosure provides a method of reducing the astringency of an ingestible composition, comprising introducing the taste-modifying composition of the second aspect and the related aspects above into the ingestible composition.In some embodiments, the ingestible composition comprises one or more astringent compounds.

[0012] In a fifth aspect, the present disclosure provides the use of the taste modifying composition of the second aspect and the related aspects above to reduce the sourness of an ingestible composition. In certain related aspects, the present disclosure provides a method of reducing the sourness of an ingestible composition, comprising introducing the taste modifying composition of the second aspect and the related aspects above into the ingestible composition. In some embodiments, the ingestible composition comprises one or more sour compounds, including certain organic acids such as, but not limited to, ascorbic acid, citric acid, lactic acid, malonic acid, malic acid, acetic acid, etc.

[0013] In a sixth aspect, the present disclosure provides use of the taste modifying composition of the second aspect and the related aspects above to enhance the sweetness of an ingestible composition. In certain related aspects, the present disclosure provides a method of enhancing the sweetness of an ingestible composition comprising introducing into the ingestible composition a taste modifying composition of the second aspect and the related aspects above. In some embodiments, the ingestible composition comprises one or more sweeteners including, but not limited to, sucrose, fructose, glucose, galactose, lactose, allulose, erythritol, sucralose, saccharin, acesulfame potassium, aspartame, neotame, steviol glycosides (e.g., rebaudioside A, rebaudioside B, rebaudioside D, rebaudioside E, rebaudioside M, etc.), and megrosides (e.g., mogroside V, isomogroside V, siamenoside I, the α-1,6-isomer of siamenoside I, etc.).

[0014] In a seventh aspect, the present disclosure provides an ingestible composition comprising the taste-modifying composition of the second aspect and the related aspects above. In some embodiments, the taste-modifying composition is present in the ingestible composition in a bitterness-reducing effective amount. In some embodiments thereof, the ingestible composition comprises one or more bitter compounds. In some embodiments thereof, the ingestible composition comprises one or more astringent compounds. In some embodiments thereof, the ingestible composition comprises one or more sour compounds. In some embodiments thereof, the ingestible composition comprises one or more sweeteners. In some embodiments thereof, the ingestible composition is a composition derived from a citrus fruit. In some embodiments, the ingestible composition is a naturally occurring composition. In some other embodiments, the ingestible composition is a non-naturally occurring composition. In some embodiments, the bitter compound is a limonoid, such as limonin, nomilin, nomilic acid, or any combination thereof. In some embodiments, the bitter compound comprises naringin.

[0015] In an eighth aspect, the present disclosure provides a flavored product comprising the ingestible composition of the seventh aspect. In some embodiments, the flavored product is a beverage product, such as soda, flavored water, tea, etc. In some other embodiments, the flavored product is a food product. In some embodiments, the flavored product is an oral care product or a chewing gum.

[0016] In a tenth aspect, the present disclosure provides a method for reducing bitterness of a citrus composition derived from a citrus fruit having huanglongbing disease, the method comprising: (a) extracting the citrus composition from at least a portion of the citrus fruit having huanglongbing disease; and (b) introducing a taste-modifying composition of the second aspect or any of the preceding related aspects to the citrus composition. In some embodiments, the citrus composition comprises an abnormally high concentration of one or more bitter compounds. In some embodiments, the bitter compounds are limonoids, such as limonin, nomilin, nomilic acid, or any combination thereof. In some embodiments, the taste-modifying composition is derived from citrus waste.

[0017] Further aspects and embodiments thereof are described below in the detailed description, drawings, abstract and claims.

[0018] Detailed Description The following detailed description describes various aspects and embodiments provided herein. The description should be read from the perspective of one of ordinary skill in the art. As such, it may not necessarily include information that is known to such a person of ordinary skill in the art.

[0019] definition The following terms and phrases have the meanings set forth below unless otherwise specified herein. This disclosure may use other terms and phrases not expressly defined herein. Such other terms and phrases have the meanings they would have within the context of this disclosure to a person skilled in the art. In some cases, a term or phrase may be defined in the singular or plural. In such cases, it is understood that any term in the singular form can include its plural counterpart, and vice versa, unless expressly indicated to the contrary.

[0020] The term "bitterness" refers to the activation of one or more T2R taste receptors by a particular compound in an ingestible composition. A "bitterness receptor blocker" or "bitterness blocker" refers to a compound that antagonizes the activation of one or more T2R receptors by a bitter compound. A reduction in bitterness refers to a reduction (e.g., partial antagonism) of one or more T2R taste receptors that would otherwise be activated by one or more compounds in the ingestible composition.

[0021] The term "astringency" refers to a trigeminal effect that is perceived as drying and mouth-pushing. Reducing astringency refers to the reduction of this trigeminal effect.

[0022] The term "sour" refers to the mildly unpleasant taste associated with organic acids such as acetic acid (vinegar). Reducing sourness refers to the reduction in the effect of this unpleasant taste.

[0023] The term "sweetness" refers to the activation of the T1R2 / T1R3 taste receptor by a particular compound in the ingestible composition. A "sweet taste receptor enhancer" or "sweetness enhancer" refers to a compound that stimulates the activation of the T1R2 / T1R3 taste receptor by a sweetener. Enhancement of sweetness refers to an increase (e.g., receptor agonism) of the T1R2 / T1R3 taste receptor to a greater extent than it would otherwise be activated by one or more compounds in the ingestible composition.

[0024] The term "polymethoxylated flavonoid" or "PMF" or "PMF compound" refers to a flavonoid compound having one or more methoxy substituents and no hydroxyl substituents. In some embodiments, the polymethoxylated flavonoid is a polymethoxylated flavone, where the numbering follows normal flavone numbering, as shown below: [ka]

[0025] In some embodiments, the PMF compound is one or more of the polymethoxylated flavone compounds listed in Table 1.

[0026] [Table 1]

[0027] The term "hydroxylated flavonoid", "hydroxy-substituted flavonoid", "hydroxyl-substituted flavonoid" or "HF" or "HF compound" refers to a flavonoid compound having at least one hydroxyl substituent. In some embodiments, the hydroxylated flavonoid is a hydroxylated flavone. Non-limiting examples include 5OHSIN (CAS No. 21763-80-4), 5OHHMQ (CAS No. 479-90-3), 5OHNOB (CAS No. 2174-59-6), 5OHTMS (CAS No. 19103-54-9), 5OHHMF (CAS No. 1176-88-1) and 5OHTAN (CAS No. 2798-20-1).

[0028] As used herein, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. For example, reference to a "substituent" includes a single substituent as well as two or more substituents, and the like.

[0029] As used herein, "hydroxy" refers to the -OH substituent and "methoxy" refers to the -OCH3 substituent.

[0030] As used herein, "for example," "for instance," "such as," or "including" are meant to introduce examples that further clarify a more general subject matter. Unless expressly stated otherwise, such examples are provided only as an aid in understanding the embodiments set forth in this disclosure and are not meant to be limiting in any way. These phrases do not imply any kind of preference for the disclosed embodiments.

[0031] As used herein, "comprise" or "comprises" or "comprising" or "comprised of" refers to an open group, meaning that the group can include additional members in addition to those explicitly listed. For example, the phrase "comprising A" means that A must be present, but other members may be present. The terms "include," "have," and "composed of" and their grammatical variations have the same meaning. In contrast, "consist of" or "consists of" or "consisting of" refers to a closed group. For example, the phrase "consisting of A" means that A and only A are present.

[0032] As used herein, "optionally" means that the subsequently described event may or may not occur. In some embodiments, the optional event does not occur. In some other embodiments, the optional event occurs one or more times.

[0033] As used herein, "or" should be given its broadest reasonable interpretation and should not be limited to an either / or configuration. Thus, the phrase "comprising A or B" means that A is present and B is not present, or B is present and A is not present, or both A and B are present. Furthermore, if, for example, A defines a class that can have multiple members, e.g., A1 and A2, one or more members of the class can be present at the same time.

[0034] Chemical structures are often shown using a "skeletal" format, such that the carbon atoms are not explicitly shown and the hydrogen atoms attached to carbon atoms are omitted entirely. For example, the structure [ka] represents butane (i.e., n-butane). Additionally, aromatic groups such as benzene are represented by showing one of the contributing resonance structures. For example, the structure [ka] represents toluene.

[0035] Other terms not included in this subsection are defined elsewhere in this Description.

[0036] PMF concentration method In certain aspects, the present disclosure provides a method for concentrating polymethoxylated flavonoids, comprising the steps of: (a) providing an organic oil comprising polymethoxylated flavonoids and hydroxyl-substituted flavonoids; and (b) introducing an extraction medium into the organic oil to form a mixture having an aqueous phase and an organic phase, wherein the extraction medium is water and C. 1~6 (c) separating at least a portion of the aqueous phase from the organic phase; and (d) generating two or more fractions of the separated aqueous phase using adsorption chromatography, wherein at least one of the two or more fractions comprises a concentration of at least 85% by weight, on a dry weight basis, of polymethoxylated flavonoids, or both polymethoxylated flavonoids and hydroxyl-substituted flavonoids.

[0037] As described above, the method includes extracting and concentrating PMF compounds from an organic oil. The organic oil can be obtained from any suitable source. For example, in some embodiments, the organic oil is a citrus oil. Such citrus oil can be obtained by any suitable method. For example, in some embodiments, the citrus oil is derived from extraction and / or distillation of oil from citrus fruits, including citrus peel. Any suitable citrus fruit can be used, including, but not limited to, orange, lemon, grapefruit, lime, kumquat, pomelo, tangelo, agri, tangerine, yuzu, or any combination thereof. In some embodiments, the citrus oil is orange peel oil. Organic oils generally contain a variety of other compounds in addition to PMFs, including HFs and a variety of other organic compounds. In some embodiments, the concentration of PMFs in the organic oil is 15% by weight or less, or 20% by weight or less, or 25% by weight or less, or 30% by weight or less, or 35% by weight or less, based on the total weight of the organic oil. The organic oil also contains HFs. In some embodiments, the weight ratio of PMF to HF in the organic oil is 12:1 or less, or 14:1 or less, or 16:1 or less, or 18:1 or less. In some embodiments, the concentration of HF in the organic oil is at least 0.5 wt %, based on the total weight of the organic oil.

[0038] The concentration method disclosed herein includes introducing an extraction medium into the organic oil to form a mixture having an aqueous phase and an organic phase. Generally, the extraction medium includes one or more solvents that form a separate phase from the organic oil. Such solvents include water and other water-miscible solvents, such as acetone, acetonitrile, tetrahydrofuran, acetaldehyde, acetone, diethanolamine, dimethylformamide, 1,4-dioxane, ethylamine, furfuryl alcohol, diethylene glycol, triethylene glycol, and other C 1~5 Alcohols such as C 1~5Examples of alcohols include, but are not limited to, methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, and glycerol. In some embodiments, the extraction medium is a mixture of water and one or more C 1~5 In some embodiments, the extraction medium comprises water and ethanol. In some such embodiments, the concentration of ethanol in the extraction medium ranges from 5% to 65% by weight, or from 10% to 60% by weight, or from 20% to 60% by weight, or from 30% to 60% by weight. In some such embodiments, the concentration of water in the extraction medium ranges from 35% to 95% by weight, or from 40% to 90% by weight, or from 40% to 80% by weight, or from 40% to 70% by weight.

[0039] By contacting the organic oil with the extraction medium, certain compounds in the organic oil are extracted into the aqueous phase.For example, in some embodiments, the PMF constitutes at least 50% by weight, or at least 55% by weight, or at least 60% by weight of the flavonoids present in the aqueous phase, based on the total flavonoid content of the aqueous phase.In some embodiments, the weight ratio of PMF to HF in the aqueous phase is 12:1 or less, or 14:1 or less, or 16:1 or less, or 18:1 or less.In some embodiments, the concentration of HF in the aqueous phase is at least 5% by weight, based on the total flavonoid content of the aqueous phase.

[0040] The concentration method disclosed herein includes separating at least a portion of the aqueous phase from the organic phase of the mixture formed after the extraction medium is introduced into the organic oil. The separating can be performed by any suitable means. Generally, the two phases can be separated, resulting in a higher percentage of the aqueous phase being separated. In some embodiments, the separating is performed in a single removal step. In other embodiments, the separating is performed in two or more removal steps.

[0041] The enrichment methods disclosed herein include using adsorption chromatography to generate two or more fractions of the separated aqueous phase, in some embodiments at least three fractions, or at least four fractions, or at least five fractions, or at least six fractions, or at least seven fractions, or at least eight fractions, or at least nine fractions, or at least ten fractions.

[0042] The fractions can be generated by any suitable means. In some embodiments, the fractions are generated by chromatography, where the separated aqueous phase is eluted into a mobile phase in the presence of a stationary phase. In general, different components of the eluted composition (e.g., the separated aqueous phase) have different relative affinities for the aqueous phase and the mobile phase, such that as fractions are collected throughout the course of elution, the fractions tend to contain concentrated amounts of compounds with similar relative affinities. Any suitable chromatographic technique can be used. In some embodiments, the fractions are generated by adsorption chromatography (or liquid-solid chromatography), where the mobile phase is a liquid and the stationary phase is a solid surface, such as a solid support.

[0043] In embodiments where adsorption chromatography is used, any suitable mobile phase and solid support can be used according to the knowledge of those skilled in the art. In some embodiments, the stationary phase is a macroporous resin that is non-polar or only moderately polar. Such stationary phases tend to retard the progression of more non-polar (or hydrophobic) compounds so that these compounds are concentrated in the fractions that are collected later.

[0044] In some embodiments, the mobile phase is a polar medium, such as an aqueous medium. In some embodiments, the mobile phase comprises water and one or more water-miscible solvents. Such water-miscible solvents include acetone, acetonitrile, tetrahydrofuran, acetaldehyde, acetone, diethanolamine, dimethylformamide, 1,4-dioxane, ethylamine, furfuryl alcohol, diethylene glycol, triethylene glycol, and other C 1~5 Alcohols include, but are not limited to, C 1~5 Examples of alcohols include, but are not limited to, methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, and glycerol. In some embodiments, the mobile phase is a mixture of water and one or more C 1~5 In some embodiments, the mobile phase comprises water and ethanol. In some such embodiments, the concentration of ethanol in the mobile phase ranges from 5% to 65% by weight, or from 10% to 60% by weight, or from 20% to 60% by weight, or from 30% to 60% by weight. In some such embodiments, the concentration of water in the mobile phase ranges from 35% to 95% by weight, or from 40% to 90% by weight, or from 40% to 80% by weight, or from 40% to 70% by weight.

[0045] In some embodiments, at least one of the two or more fractions comprises PMF and HF at a concentration of at least 80%, or at least 85%, or at least 87% by weight on a dry weight basis. In some embodiments, the weight ratio of PMF to HF in at least one of the two or more fractions is at least 9:1, at least 10:1, at least 11:1, at least 12:1, or at least 15:1, or at least 17:1, or at least 19:1. In some embodiments, the concentration of HF in at least one of the two or more fractions is 10% or less, 9% or less, 8% or less, 7% or less, or 6% or less, or 5% or less by weight on a dry weight basis.

[0046] In some embodiments, the solvent is partially or completely removed from at least one of the two or more fractions. Solvent removal can be accomplished by any suitable means, including evaporation, drying (by moderate heating), vacuum-assisted methods, etc. Such removal results in either a highly concentrated PMF composition or a dry solid that contains primarily PMF.

[0047] In some embodiments, at least one of the two or more fractions, which may be optionally dried or concentrated by solvent removal, is washed with an alkaline aqueous solution. Any suitable water-soluble base can be used to make the alkaline wash solution. Suitable bases include, but are not limited to, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, calcium oxide, calcium carbonate, potassium carbonate, or any combination thereof. In some embodiments, the alkaline wash solution can also contain certain metal compounds, such as ferric chloride.

[0048] The base can be at any suitable concentration, for example, about 5% by weight of the wash solution based on the total weight of the wash solution.

[0049] In some embodiments, at least one of the two or more fractions, which can be optionally dried or concentrated by solvent removal, is washed to form an insoluble solid in the aqueous medium, which can be collected and dried. The insoluble solid typically has a high concentration of PMF. For example, in some embodiments, the insoluble solid comprises PMF and HF at a concentration of at least 85% by weight, or at least 87% by weight, or at least 90% by weight on a dry weight basis. In some embodiments, the weight ratio of PMF to HF in the insoluble solid is at least 9:1, at least 10:1, at least 11:1, at least 12:1, or at least 15:1, or at least 17:1, or at least 19:1. In some embodiments, the concentration of HF in the insoluble solid is 10% by weight or less, 9% by weight or less, 8% by weight or less, or 7% by weight or less, or 6% by weight or less, or 5% by weight or less on a dry weight basis.

[0050] Additional steps may be applied to the recovered solids to prepare them for storage and to prevent oxidation, thermal decomposition, or photodecomposition.

[0051] Taste-modifying compositions The above method may result in the formation of a composition highly enriched in PMF, as described in certain embodiments above. In some embodiments, the above method results in a PMF-containing composition having reduced off-note intensity.

[0052] Thus, in certain aspects, the present disclosure provides a taste modifying composition comprising one or more PMFs and one or more HFs. In some embodiments, the PMFs are flavone compounds. In some further such embodiments, the PMFs are one or more compounds selected from the group consisting of the six compounds in Table 1 or any combination thereof.

[0053] In some embodiments, the taste-modifying composition comprises a PMF or both a PMF and a HF at a concentration of at least 85% by weight, or at least 87% by weight, or at least 90% by weight, on a dry weight basis. In some embodiments, the weight ratio of PMF to HF in the taste-modifying composition is at least 9:1, at least 10:1, at least 11:1, at least 12:1, or at least 15:1, or at least 17:1, or at least 19:1. In some embodiments, the concentration of HF in the taste-modifying composition is 10% by weight or less, 9% by weight or less, 8% by weight or less, 7% by weight or less, or 6% by weight or less, or 5% by weight or less, on a dry weight basis (excluding the weight of the bulking agent in the solid composition, if present).

[0054] The taste-modifying composition can be in any suitable form. For example, in some embodiments, the taste-modifying composition is a solid, such as a solid in the form of a powder, granules, etc. In some such embodiments, other ingredients such as bulking agents, desiccants, etc. can be added. In some embodiments, the taste-modifying composition is a liquid, and a liquid carrier, such as an aqueous carrier, is introduced to dissolve or suspend the PMF compound.

[0055] In some embodiments, the taste-modifying composition is the product of the method provided above or any embodiment thereof.

[0056] Uses and Methods In certain aspects, the present disclosure provides the use of any of the taste-modifying compositions of the above-mentioned aspects and embodiments to reduce the bitterness of an ingestible composition. In some embodiments thereof, the ingestible composition comprises one or more bitter compounds. In some embodiments thereof, the ingestible composition is a composition derived from a citrus fruit. In some embodiments, the one or more bitter compounds comprise limonoids, such as limonin, nomilin, nomilic acid, or any combination thereof. In some embodiments, the one or more bitter compounds comprise naringin. In certain related aspects, the present disclosure provides a method of reducing the bitterness of an ingestible composition, the method comprising introducing any of the taste-modifying compositions of the above-mentioned aspects and embodiments into the ingestible composition.

[0057] In certain aspects, the present disclosure provides the use of any of the taste-modifying compositions of the above-mentioned aspects and embodiments to reduce the astringency of an ingestible composition. In some embodiments thereof, the ingestible composition comprises one or more astringent compounds. In some embodiments thereof, the ingestible composition is a composition derived from citrus fruit. In certain related aspects, the present disclosure provides a method for reducing the astringency of an ingestible composition, comprising introducing any of the taste-modifying compositions of the above-mentioned aspects and embodiments into the ingestible composition.

[0058] In certain aspects, the present disclosure provides the use of the taste-modifying composition of any of the above aspects and embodiments to reduce the sourness of an ingestible composition. In some embodiments thereof, the ingestible composition comprises one or more sour compounds, such as organic acids. Examples of such organic acids include ascorbic acid, acetic acid, citric acid, lactic acid, malic acid, malonic acid, and the like. In some embodiments thereof, the ingestible composition is a composition derived from citrus fruit. In some embodiments, the ingestible composition is a fermented beverage, such as kombucha. In certain related aspects, the present disclosure provides a method of reducing the sourness of an ingestible composition, the method comprising introducing the taste-modifying composition of any of the above aspects and embodiments into the ingestible composition.

[0059] In certain aspects, the present disclosure provides the use of any of the taste-modifying compositions of the above-mentioned aspects and embodiments to enhance the sweetness of an ingestible composition. In some embodiments thereof, the ingestible composition comprises one or more sweeteners. Suitable sweeteners include natural sweeteners, such as glucose, sucrose, fructose, and high-potency sweeteners, such as aspartame, neotame, sucralose, saccharin, acesulfame potassium, rebaudiosides, mogrosides, and the like. In some embodiments, the ingestible composition is a composition derived from citrus fruits. In certain related aspects, the present disclosure provides a method for enhancing the sweetness of an ingestible composition, comprising introducing any of the taste-modifying compositions of the above-mentioned aspects and embodiments into the ingestible composition.

[0060] In certain aspects, the present disclosure provides the use of any of the taste-modifying compositions of the above-mentioned aspects and embodiments to enhance the texture of an ingestible composition. In some embodiments thereof, the ingestible composition comprises one or more sweeteners. Suitable sweeteners include natural sweeteners, such as glucose, sucrose, fructose, and the like, as well as high-potency sweeteners, such as aspartame, neotame, sucralose, saccharin, acesulfame potassium, rebaudiosides, mogrosides, and the like. In some embodiments, the ingestible composition is a composition derived from citrus fruits. In certain related aspects, the present disclosure provides a method for enhancing the texture of an ingestible composition, comprising introducing any of the taste-modifying compositions of the above-mentioned aspects and embodiments into the ingestible composition.

[0061] The aforementioned uses and methods generally involve the use of a PMF-containing taste-modifying composition in an ingestible composition containing one or more additional ingredients. In certain embodiments of any aspect and embodiment described herein that refers to an ingestible composition, the ingestible composition is a composition that is specially manufactured for the production of a non-naturally occurring product, such as a flavored product, such as a food or beverage product.

[0062] In certain embodiments, the present disclosure provides an ingestible composition comprising the taste-modifying composition of any of the aforementioned aspects and embodiments. In some embodiments, the taste-modifying composition is present in the ingestible composition in a concentration sufficient to reduce bitterness, reduce astringency, reduce sourness, enhance sweetness, or enhance texture. In some embodiments thereof, the ingestible composition comprises one or more bitter compounds. In some embodiments thereof, the ingestible composition comprises one or more astringent compounds. In some embodiments thereof, the ingestible composition comprises one or more sour compounds. In some embodiments thereof, the ingestible composition comprises one or more sweeteners. In some embodiments thereof, the ingestible composition is a composition derived from citrus fruit. In some embodiments, the ingestible composition is a naturally occurring composition. In some other embodiments, the ingestible composition is a non-naturally occurring composition. In some embodiments, the bitter compound is a limonoid, such as limonin, nomilin, nomilic acid, or any combination thereof. In some embodiments, the bitter compound comprises naringin.

[0063] The taste-modifying composition can be present in the ingestible composition at any suitable concentration. For example, in some embodiments, the taste-modifying composition is present in the ingestible composition at a concentration sufficient to provide a concentration of the PMF compound in the ingestible composition in the range of 0.01 ppm to 1000 ppm, or 0.01 ppm to 900 ppm, or 0.01 ppm to 800 ppm, or 0.01 ppm to 700 ppm, or 0.01 ppm to 600 ppm, or 0.1 ppm to 500 ppm, or 0.1 ppm to 400 ppm, or 0.1 ppm to 300 ppm, or 0.1 ppm to 200 ppm, or 1 ppm to 100 ppm, or 1 ppm to 80 ppm, or 1 ppm to 60 ppm, or 1 ppm to 50 ppm, or 1 ppm to 40 ppm.

[0064] The ingestible compositions described herein, whether as compositions or as part of a use or method, in some embodiments include one or more bitter compounds. The bitter compounds can be any suitable bitter compounds commonly found in natural foods. In some embodiments, the bitter compounds are compounds extracted from plants of the Meliaceae family or plants of the Rutacaea family. In some further embodiments, the bitter compounds are extracts of plants of the Rutacaea family and the Citrus genus, such as extracts from orange, lemon, grapefruit, lime, kumquat, pomelo, tangelo, agri, tangerine or yuzu trees or fruits. In some embodiments, the bitter compounds are triterpenes. In some further embodiments, the bitter compounds are tetranortriterpenoids. In some further embodiments, the bitter compounds are limonoids. In some such embodiments, the bitter compounds are limonin, nomilin, nomilic acid, azadirachtin, or any combination thereof. In some embodiments, the bitter compounds are limonin. In some embodiments, the bitter compound is nomilin. In some embodiments, the bitter compound is naringin.

[0065] In certain other embodiments, the ingestible composition comprises a bitter compound and a taste-modifying composition. In some embodiments, the concentration of the PMF compound in the ingestible composition is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda. Bitter compounds include, but are not limited to, active pharmaceutical ingredients (APIs), tannins (such as those found in coffee, tea, wine), caffeine, quinine, catechins, polyphenols, potassium chloride, menthol, or plant starches or proteins, algal proteins or starches, fungal proteins or starches, alcohol, and any combination thereof.

[0066] In certain other embodiments, the ingestible composition comprises an acidic compound and a taste modifying composition. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as soda. Acidic compounds include, but are not limited to, organic acids, such as acetic acid, malonic acid, citric acid, and the like.

[0067] In some cases, it may be possible to reduce the amount of sweetener in the product by reducing the bitterness or enhancing the sweetness.

[0068] In certain other embodiments, the ingestible composition comprises sucrose and a taste-modifying composition. In some such embodiments, the introduction of the PMF compound allows for the use of less sucrose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more sucrose. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda. The sucrose can be introduced in any suitable form, such as natural syrup (sugar cane syrup).

[0069] In certain other embodiments, the ingestible composition comprises fructose (e.g., in the form of high fructose corn syrup) and a taste-modifying composition. In some such embodiments, the introduction of the PMF compound allows for the use of less fructose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more fructose. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda.The fructose can be provided in any suitable form, such as natural syrup, high fructose corn syrup, etc.

[0070] In certain other embodiments, the ingestible composition comprises D-glucose and a taste-modifying composition. In some such embodiments, the introduction of the PMF compound allows for the use of less D-glucose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more D-glucose. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda. The glucose can be introduced in any suitable form, such as a natural syrup.

[0071] In certain other embodiments, the ingestible composition comprises sucralose and a taste-modifying composition. In some such embodiments, the introduction of the PMF compound allows the use of less sucralose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more sucralose. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda.

[0072] In certain other embodiments, the ingestible composition comprises a rebaudioside (e.g., rebaudioside A, rebaudioside B, rebaudioside D, rebaudioside E, rebaudioside M, or any combination thereof) and a taste-modifying composition. In some such embodiments, the introduction of a PMF compound makes it possible to use less rebaudioside (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more rebaudioside. In some embodiments, the concentration of PMF compounds is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda.

[0073] In certain other embodiments, the ingestible composition comprises acesulfame potassium and a taste-modifying composition. In some such embodiments, the introduction of the PMF compound allows for the use of less acesulfame K (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more acesulfame K. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions may be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below: In other embodiments, the ingestible composition is a beverage product, such as a soda.

[0074] In certain other embodiments, the ingestible composition comprises allulose and a taste-modifying composition. In some such embodiments, the introduction of the PMF compound allows the use of less allulose (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more allulose. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda.

[0075] In certain other embodiments, the ingestible composition comprises erythritol and a taste-modifying composition. In some such embodiments, the introduction of the PMF compound allows for the use of less erythritol (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more erythritol. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda.

[0076] In certain other embodiments, the ingestible composition comprises aspartame or neotame and a taste-modifying composition. In some such embodiments, the introduction of the PMF compound allows for the use of less aspartame or neotame (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more aspartame or neotame. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the food products specifically listed below: In other embodiments, the ingestible composition is a beverage product, such as a soda.

[0077] In certain other embodiments, the ingestible composition comprises a mogroside (e.g., mogroside III, mogroside IV, mogroside V, siamenoside, isomogroside V, mogroside IVE, isomogroside V, mogroside IIIE, 11-oxomogroside V, alpha isomer of siamenoside I, and any combination thereof) and a taste-modifying composition. In some such embodiments, the introduction of a PMF compound allows for the use of less mogroside (e.g., more than 10% less, more than 20% less, more than 30% less, more than 40% less, more than 50% less, more than 60% less, or more than 70% less) and still achieve a sweetness level characteristic of a comparable product that uses more mogroside. In some embodiments, the concentration of the PMF compound is 1000 ppm or less, or 900 ppm or less, or 800 ppm or less, or 700 ppm or less, or 600 ppm or less, or 500 ppm or less, or 400 ppm or less, or 300 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 25 ppm or less, or 10 ppm or less. Such ingestible compositions can be in any suitable form. In some embodiments, the ingestible composition is a food product, such as any of the foods specifically listed below. In other embodiments, the ingestible composition is a beverage product, such as a soda. Additional mogroside compounds that may be suitably used are described in U.S. Patent Application Publication No. 2017 / 0119032.

[0078] Thus, in some embodiments, the composition according to any of the above aspects (including any use or method) comprises a taste-modifying composition and one or more sweeteners. In some embodiments, the composition further comprises a vehicle. In some embodiments, the vehicle is water. In some embodiments, the PMF compound is present at a concentration below its sweetness perception threshold.

[0079] For example, in some embodiments, the sweetener is present in an amount of about 0.1% to about 12% by weight. In some embodiments, the sweetener is present in an amount of about 0.2% to about 10% by weight. In some embodiments, the sweetener is present in an amount of about 0.3% to about 8% by weight. In some embodiments, the sweetener is present in an amount of about 0.4% to about 6% by weight. In some embodiments, the sweetener is present in an amount of about 0.5% to about 5% by weight. In some embodiments, the sweetener is present in an amount of about 1% to about 2% by weight. In some embodiments, the sweetener is present in an amount of about 0.1% to about 5% by weight. In some embodiments, the sweetener is present in an amount of about 0.1% to about 4% by weight. In some embodiments, the sweetener is present in an amount of about 0.1% to about 3% by weight. In some embodiments, the sweetener is present in an amount of about 0.1% to about 2% by weight. In some embodiments, the sweetener is present in an amount of about 0.1% to about 1% by weight. In some embodiments, the sweetener is present in an amount of about 0.1% to about 0.5% by weight. In some embodiments, the sweetener is present in an amount of about 0.5% to about 10% by weight. In some embodiments, the sweetener is present in an amount of about 2% to about 8% by weight. In some further embodiments of the embodiments described in this paragraph, the sweetener is sucrose, fructose, glucose, xylitol, erythritol, or a combination thereof.

[0080] In some other embodiments, the sweetener is present in an amount between 10 ppm and 1000 ppm. In some embodiments, the sweetener is present in an amount between 20 ppm and 800 ppm. In some embodiments, the sweetener is present in an amount between 30 ppm and 600 ppm. In some embodiments, the sweetener is present in an amount between 40 ppm and 500 ppm. In some embodiments, the sweetener is present in an amount between 50 ppm and 400 ppm. In some embodiments, the sweetener is present in an amount between 50 ppm and 300 ppm. In some embodiments, the sweetener is present in an amount between 50 ppm and 200 ppm. In some embodiments, the sweetener is present in an amount between 50 ppm and 150 ppm. In some further embodiments of the embodiments described in this paragraph, the sweetener is a steviol glycoside, a mogroside, a derivative of any of the foregoing, such as a glycoside derivative (e.g., glucosylates), or any combination thereof.

[0081] The composition may include any suitable sweetener or combination of sweeteners. In some embodiments, the sweetener is a sweetener composition that includes common carbohydrate sweeteners, such as sucrose, fructose, glucose, and natural sugars, such as corn syrup (including high fructose corn syrup) or other syrups or sweetener concentrates derived from natural fruit and plant sources. In some embodiments, the sweetener is sucrose, fructose, or a combination thereof. In some embodiments, the sweetener is sucrose. In some other embodiments, the sweetener is selected from rare natural sugars, including D-allose, D-psicose, L-ribose, D-tagatose, L-glucose, L-fucose, L-albinose, D-turanose, and D-leucrose. In some embodiments, the sweetener is selected from semi-synthetic "sugar alcohol" sweeteners, such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, etc. In some embodiments, the sweetener is selected from artificial sweeteners such as aspartame, saccharin, acesulfame-K, cyclamate, sucralose, and alitame. In some embodiments, the sweetener is selected from the group consisting of cyclamic acid, mogrosides, tagatose, maltose, galactose, mannose, sucrose, fructose, lactose, neotame and other aspartame derivatives, glucose, D-tryptophan, glycine, maltitol, lactitol, isomalt, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysates (HSH), stevioside, rebaudioside A, other sweet stevia-based glycosides, chemically modified steviol glycosides (such as glucosylated steviol glycosides), mogrosides, chemically modified mogrosides (such as glucosylated mogrosides), carrelame, and other guanidine-based sweeteners. In some embodiments, the sweetener is a combination of two or more of the sweeteners described in this paragraph.In some embodiments, the sweetener may be a combination of two, three, four or five sweeteners disclosed herein.In some embodiments, the sweetener may be sugar.In some embodiments, the sweetener may be a combination of one or more sugars and other natural and artificial sweeteners. In some embodiments, the sweetener is a sugar. In some embodiments, the sugar is cane sugar. In some embodiments, the sugar is beet sugar. In some embodiments, the sugar may be sucrose, fructose, glucose or a combination thereof. In some embodiments, the sugar may be sucrose. In some embodiments, the sugar may be a combination of fructose and glucose.

[0082] Sweeteners can also include, for example, sweetener compositions comprising one or more natural or synthetic carbohydrates, such as corn syrup, high fructose corn syrup, high maltose corn syrup, glucose syrup, sucralose syrup, hydrogenated glucose syrup (HGS), hydrogenated starch hydrolysates (HSH), or other syrups or sweetener concentrates derived from natural fruit and plant sources, or semi-synthetic "sugar alcohol" sweeteners such as polyols. Non-limiting examples of polyols in some embodiments include erythritol, maltitol, mannitol, sorbitol, lactitol, xylitol, isomalt, propylene glycol, glycerol (glycerin), threitol, galactitol, palatinose, reduced isomaltooligosaccharides, reduced xylooligosaccharides, reduced gentiooligosaccharides, reduced maltose syrup, reduced glucose syrup, isomaltulose, maltodextrin, and the like, as well as sugar alcohols, or any other carbohydrates or combinations thereof that can be reduced and do not adversely affect the taste.

[0083] Sweeteners include agave inulin, agave nectar, agave syrup, amazake, brazzein, brown rice syrup, coconut crystals, coconut sugar, coconut syrup, date sugar, fructans (also called inulin fiber, fructooligosaccharides or oligofructose), green stevia powder, stevia rebaudiana (stevia rebaudiana), rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside I, rebaudioside H, rebaudioside L, rebaudioside K, rebaudioside J, rebaudioside N, rebaudioside O, rebaudioside M and other sweet stevia glycosides, stevioside, stevioside, stevioside extract, honey, Jerusalem artichoke syrup, licorice root, Monk fruit (fruit, powder or extract), lucuma (fruit, powder or extract), maple sap (e.g., Acer saccharum, Acer nigrum, Acer rubrum, Acer saccharinum), saccharinum, Acer platanoides, Acer negundo, Acer macrophyllum, Acer grandidentatum, Acer glabrum, Acer mono), maple syrup, maple sugar, walnut sap (including sap extracted from, for example, Juglans cinerea, Juglans nigra, Juglans ailatifolia, Juglans regia), birch sap (including sap extracted from, for example, Betula papyrifera, Betula arganiensis, Betula alleghaniensis, Betula lenta, Betula nigra, Betula populifolia,including sap extracted from Betula pendula), sycamore sap (e.g., sap extracted from Platanus occidentalis), asada sap (e.g., sap extracted from Ostrya virginiana), virginiana), mascovado, molasses (e.g. blackstrap molasses), molasses sugar, monatin, monellin, cane sugar (also called natural sugar, unrefined cane sugar or sucrose), palm sugar, panocha, piloncillo, rapadura, raw sugar, rice syrup, sorghum, sorghum syrup, cassava syrup (also called tapioca syrup), thaumatin, yacon root, malt syrup, barley malt syrup, barley malt flour, beet sugar, cane sugar, crystallized fruit juice crystals, caramel, Carbitol, carob syrup, castor sugar, hydrogenated starch aqueous extract, hydrolyzed canned juice, hydrolyzed starch, invert sugar, anethole, arabinogalactan, arop syrup, P-4000, acesulfame potassium (also called acesulfame K or ace K), alitame (also called acrème), advantame, aspartame, bayunoside, neotame, benzamide derivatives, bernadame, canderel, carre Carrelame and other guanidine sweeteners, vegetable fiber, corn sugar, coupling sugar, curculin, cyclamate, cyclocaryoside I, demerara, dextran, dextrin, malt syrup, dulcin, sucrose, valgin, dulcoside A, dulcoside B, erin, enoxolone, maltodextrin, saccharin, estragole, ethyl maltol, glucine, gluconic acid, gluconolactone, glucosamine, glucoronic acid, glycerol, glycine Glycyphyllin, glycyrrhizin, glycyrrhetinic acid monoglucuronide, golden sugar, yellow sugar, golden syrup, granulated sugar, gynostema, hernandalusine, isomerized liquid sugar, jalab, chicory root dietary fiber, kynurenine derivatives (including N'-formyl-kynurenine, N'-acetyl-kynurenine, 6-chloro-kynurenine), galactitol, litesse, ligicane, lycasin, ragduname, guanidine,Falernum, Mabinrin I, Mabinrin II, Maltol, Multisorb, Maltodextrin, Maltotriol, Mannosamine, Miraculin, Starch syrup, Mogrosides (including, for example, Mogroside IV, Mogroside V, and Neomogroside), Muclodiosides, Nanosugar, Naringin dihydrochalcone, Neohesperidin dihydrochalcone, Nib sugar, Nigero-oligosaccharides, Norbu, Orgate syrup, Osladin, Pekmez, Pentadin, Periandrin I, Perillaldehyde, Perillartine, Petophyllum, Phenylalanine, Phlomisoside I, Phlorogizin, Phlodulcin, Polyglycitol syrup, Polypodoside A, Pterocaryoside A, Pterocaryoside B, Rebiana, Refined syrup, Rub syrup (rub The sweetener may be a natural or synthetic sweetener, including, but not limited to, syrup, rubusoside, selligueain A, sugar (shugr), siamenoside I, siraitia grosvenorii, soy oligosaccharides, splenda, SRI oxime V, steviol glycosides, steviolbioside, stevioside, strogin 1, 2 and 4 sucronates, sucrononate, sugar, suosan, phloridzin, super aspartame, tetrasaccharide, threitol, treacle, trilobtain, tryptophan and derivatives (6-trifluoromethyl-tryptophan, 6-chloro-D-tryptophan), vanilla sugar, volemitol, birch xylose, aspartame-acesulfame, asguline, and combinations or blends of any two or more thereof.

[0084] In yet other embodiments, the sweetener may be a chemically or enzymatically modified natural high-potency sweetener. Modified natural high-potency sweeteners include glycosylated natural high-potency sweeteners, such as glycosyl-, galactosyl- or fructosyl-derivatives containing 1-50 glycoside residues. Glycosylated natural high-potency sweeteners may be prepared by enzymatic transglycosylation reactions catalyzed by various enzymes with transglycosylation activity. In some embodiments, modified sweeteners may be substituted or unsubstituted.

[0085] Additional sweeteners also include combinations of any two or more of any of the aforementioned sweeteners. In some embodiments, the sweetener may include a combination of two, three, four or five sweeteners disclosed herein. In some embodiments, the sweetener may be a sugar. In some embodiments, the sweetener may be a combination of one or more sugars with other natural and artificial sweeteners. In some embodiments, the sweetener is a caloric sweetener, such as sucrose, fructose, xylitol, erythritol or combinations thereof. In some embodiments, the ingestible composition is free of, or substantially free of, stevia-derived sweeteners, such as steviol glycosides, glucosylated steviol glycosides or rebaudiosides (or in some embodiments). For example, in some embodiments, the ingestible composition does not contain stevia-derived sweeteners, or contains stevia-derived sweeteners at a concentration of 1000 ppm or less, or 500 ppm or less, or 200 ppm or less, or 100 ppm or less, or 50 ppm or less, or 20 ppm or less, or 10 ppm or less, or 5 ppm or less, or 3 ppm or less, or 1 ppm or less.

[0086] The ingestible composition or sweetener concentrate may, in certain embodiments, include any additional ingredient or combination of ingredients commonly used in food and beverage products, including, but not limited to, the following: Acids, such as citric acid, phosphoric acid, ascorbic acid, sodium sulfate, lactic acid or tartaric acid; bitter components, such as caffeine, quinine, green tea, catechins, polyphenols, green robusta coffee extract, green coffee extract, potassium chloride, menthol or proteins (e.g. proteins and protein isolates derived from plants, algae or fungi); Colouring agents, such as caramel colour, Red 40, Yellow 5, Yellow 6, Blue 1, Red 3, purple carrot, black carrot juice, purple potato, vegetable juice, fruit juice, beta carotene, turmeric curcumin or titanium dioxide; preservatives, such as sodium benzoate, potassium benzoate, potassium sorbate, sodium metabisulfate, sorbic acid or benzoic acid; Antioxidants, such as ascorbic acid, disodium calcium EDTA, alpha tocopherol, mixed tocopherols, rosemary extract, grape seed extract, resveratrol or sodium hexametaphosphate; Vitamins or functional ingredients such as resveratrol, Co-Q10, omega-3 fatty acids, theanine, choline chloride (cytocholine), Fibersol, inulin (chicory root), taurine, ginseng extract, guanana extract, ginger extract, L-phenylalanine, L-carnitine, L-tartrate, D-glucoronolactone, inositol, bioflavonoids, echinacea, ginkgo biloba, yerba mate, flaxseed oil, garcinia cambogia lind extract, white tea extract, ribose, milk thistle extract, grape seed extract, pyroxyxine HCl (vitamin B6), cyanoobalamin n) (vitamin B12), niacinamide (vitamin B3), biotin, calcium lactate, calcium pantothenate (pantothenic acid), calcium phosphate, calcium carbonate, chromium chloride, chromium polynicotinate, cupric sulfate, folic acid, ferric pyrophosphate, iron, magnesium lactate, magnesium carbonate, magnesium sulfate, monopotassium phosphate, monosodium phosphate, phosphorus, potassium iodide, potassium phosphate, riboflavin, sodium sulfate, sodium gluconate, sodium polyphosphate, sodium bicarbonate, thiamine mononitrate, vitamin D3, vitamin A palmitate, zinc gluconate, zinc lactate or zinc sulfate, etc; Opacifiers, such as ester gun, brominated vegetable oil (BVO) or sucrose acetate isobutyrate (SAIB); Buffers, such as sodium citrate, potassium citrate or salts; Flavorings, such as propylene glycol, ethyl alcohol, glycerin, gum arabic (gum acacia), maltodextrin, modified corn starch, dextrose, natural flavors, natural flavors including other natural flavors (natural flavors WONF), natural and artificial flavors, artificial flavors, silicon dioxide, magnesium carbonate, or tricalcium phosphate; or Starches and stabilizers, such as pectin, xanthan gum, carboxymethylcellulose (CMC), polysorbate 60, polysorbate 80, medium chain triglycerides, cellulose gel, cellulose gum, sodium caseinate, modified food starch, gum arabic (gum acacia), inulin or carrageenan.

[0087] The ingestible composition may have any suitable pH. In some embodiments, the taste-modifying compositions disclosed herein enhance the sweetness of a sweetener under a wide range of pH, for example, from lower to neutral pH. Lower and neutral pH include, but are not limited to, about 2.5 to about 8.5, about 3.0 to about 8.0, about 3.5 to about 7.5, and about 4.0 to about 7. In certain embodiments, the compounds disclosed and described herein, individually or in combination, can enhance the perceived sweetness of a certain concentration of sweetener in a taste test at a compound concentration of about 50 μM, 40 μM, 30 μM, 20 μM, or 10 μM, both at low and neutral pH values. In certain embodiments, the enhancement factor of the compounds disclosed and described herein, individually or in combination, at lower pH is substantially similar to the enhancement factor of the compounds at neutral pH. Such consistent sweetness enhancing properties over a wide range of pH allow for the broad use of the compounds disclosed and described herein, individually or in combination, in a wide variety of foods and beverages.

[0088] The ingestible compositions according to any of the foregoing embodiments may also, in certain embodiments, comprise one or more additional compounds, such as a sweet taste enhancing compound (e.g., hesperetin, hesperetin dihydrochalcone, neohesperidin dihydrochalcone, neohesperitin, phloretin, naringenin, eriodictyol, homoeriodictyol, trilobatin, hesperitin dihydrochalcone glucoside, 3-hydroxybenzoic acid, glucosylated steviol glycoside, (2R,3R)-3-acetoxy-5,7,4'-trihydroxyflavanone, (2R,3R)-3-acetoxy-5,7,3'-trihydroxy-4'-methoxyflavanone, etc.), a bitter taste blocking compound, a umami taste enhancing compound, a sour or licorice taste reducing compound, a salty taste enhancing compound, a cooling effect enhancing compound, or any combination of the foregoing.

[0089] Thus, in some embodiments, the ingestible compositions disclosed herein include a taste-modifying composition according to any of the above embodiments or a combination of the above embodiments, in combination with one or more sweetness enhancing compounds. Such sweetness enhancing compounds include naturally occurring compounds such as hesperetin, hesperitin dihydrochalcone, hesperitin dihydrochalcone glucoside, 3-hydroxybenzoic acid, phloretin, naringenin, rhoifolin, glucosylated steviol glycoside, (2R,3R)-3-acetoxy-5,7,4'-trihydroxyflavanone, (2R,3R)-3-acetoxy-5,7,3'-trihydroxy-4'-methoxamine, and the like. Examples of suitable compounds include, but are not limited to, cyflavanone, or synthetic compounds such as any of the compounds described in U.S. Pat. Nos. 8,541,421, 8,815,956, 9,834,544, 8,592,592, 8,877,922, 9,000,054, and 9,000,051, and U.S. Patent Application Publication No. 2017 / 0119032. In embodiments in which the taste modifying composition is used in combination with a sweetener enhancer, the concentration of the PMF compound used in combination with such sweetener enhancer may be 1:1000 to 1000:1, or 1:100 to 100:1, or 1:50 to 50:1, or 1:25 to 25:1, or 1:10 to 10:1, such as 1:25, 1:24, 1:23, 1:22, 1:21, 1:20, 1:19, 1:18, 1:17, 1:16, 1:1 In some embodiments of any of the preceding embodiments, the taste-modifying composition has a w / w ratio in the range of 1:5, 1:14, 1:13, 1:12, 1:11, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, 20:1, 21:1, 22:1, 23:1, 24:1, or 25:1. In some embodiments of any of the preceding embodiments, the taste-modifying composition is combined with glucosylated steviol glycosides in any of the above ratios.As used herein, the term "glucosylated steviol glycoside" refers to the product of enzymatic glucosylation of natural steviol glycoside compounds. Glucosylation generally occurs through glycosidic bonds such as α-1,2, α-1,4, α-1.6, β-1,2, β-1,4, β-1,6, etc. In some embodiments of any of the preceding embodiments, the TM1 compound (or any food acceptable salt thereof) is combined with N-(1-((4-amino-2,2-dioxo-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)-2-methyl-propan-2-yl)isonicotinamide in any of the ratios described above.

[0090] Similarly, the taste-modifying compositions are also used in some embodiments in combination with umami enhancers, cooling (TRPM8) enhancers, bitterness blockers, acidity regulators, texture enhancers, flavor-masking compounds, or any combination thereof.

[0091] In some aspects related to the previous aspects and embodiments, the present disclosure provides for the use of the taste modifying compositions disclosed herein to enhance the flavor of a flavored composition, such as a flavored article. Such a flavored composition can use any suitable flavor, for example any of the flavors described above.

[0092] Flavoured products and concentrates In certain aspects, the present disclosure provides a flavored product comprising any of the ingestible compositions of the previous aspects. In some embodiments, the flavored product is a beverage product, such as soda, flavored water, tea, etc. In some other embodiments, the flavored product is a food product, such as yogurt.

[0093] In embodiments where the flavored product is a beverage, the beverage may be selected from the group consisting of enhanced sparkling beverages, cola, lemon-lime flavored sparkling beverages, orange flavored sparkling beverages, grape flavored sparkling beverages, strawberry flavored sparkling beverages, pineapple flavored sparkling beverages, ginger ale, root beer, fruit juice, fruit flavored juice, juice drink, nectar, vegetable juice, vegetable flavored juice, sports drink, energy drink, enhanced water drink, enhanced water with vitamins, near water drink, coconut water, tea-based drink, coffee, cocoa drink, beverages containing dairy ingredients, beverages containing cereal extracts, and smoothies. In some embodiments, the beverage may be a soft drink.

[0094] In certain embodiments of any of the aspects and embodiments described herein that refer to a flavored product, the flavored product is a non-naturally occurring product, such as a packaged food or beverage product.

[0095] Further non-limiting examples of food and beverage products or formulations include sweet coatings, frostings, or glazes for such products or any articles included in the soup category, the dried prepared foods category, the beverage category, the ready meal category, the canned or preserved foods category, the frozen prepared foods category, the chilled prepared foods category, the snack foods category, the baked goods category, the confectionery category, the dairy category, the ice cream category, the meal replacements category, the pasta and noodles category, and the sauces, dressings, condiments category, the baby food category, and / or the spreads category.

[0096] In general, the soup category refers to canned / preserved, dehydrated, instant, chilled, UHT and frozen soups. For the purposes of this definition, soup means food prepared from meat, poultry, fish, vegetables, grains, fruits and other ingredients, cooked in a liquid that may contain some or all visible portions of these ingredients. Soups may be clear (as broths) or thick (as chowders), smooth, pureed or chunky, ready to serve, semi-condensed or condensed, and may be served hot or cold, as a first course or as the main course of a meal, or as a snack between meals (sipped in small portions like a beverage). Soups may be used as an ingredient for cooking other meal components and may range from broths (consomme) to sauces (cream or cheese-based soups).

[0097] The dehydrated and prepared foods category generally refers to: (i) cooking aid products, such as powders, granules, pastes, concentrated liquid products, such as concentrated bouillons, bouillons and bouillon-like products in compressed cubes, tablets, powders or granules form, sold separately (regardless of technology) as finished products or as ingredients in products, sauces and recipe mixes; (ii) dietary solution products, such as dehydrated and freeze-dried soups, such as dehydrated soup mixes, dehydrated instant soups, dehydrated semi-cooked soups, dehydrated or packaged ready-made staples and single-serving main dishes including pasta, potato and rice dishes; (iii) meal accompaniment products, such as condiments, marinades, salad dressings, salad toppings, dips, bread crumbs, batter mixes, shelf stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, such as salad recipe mixes, sold in dehydrated, liquid or frozen state, either as finished products or as ingredients in products.

[0098] The beverage category generally refers to beverages, beverage mixes and concentrates, including but not limited to carbonated and non-carbonated beverages, alcoholic and non-alcoholic beverages, ready-to-drink beverages, liquid concentrate formulations for producing beverages such as sodas, and dry powdered beverage pre-mixes. The beverage category also includes alcoholic drinks, soft drinks, sports drinks, isotonic drinks and hot drinks. Alcoholic drinks include but are not limited to beer, cider / perry, FAB, wine and spirits. Soft drinks include carbonated, e.g. cola and non-cola carbonated; fruit juices, e.g. juice, nectar, juice drinks and fruit flavored drinks; bottled water, e.g. sparkling water, spring water and purified water / table water; functional drinks, e.g. which may be carbonated or non-carbonated and include sports drinks, energy drinks or elixir drinks; concentrates, e.g. ready-to-drink measured liquid and powder concentrates. Hot or cold drinks include, but are not limited to, coffee or iced coffee, such as brewed, instant and combination coffees; tea or iced tea, such as black tea, green tea, white tea, oolong tea and flavored teas; and other beverages, including flavored, malt or plant-based powders, granules, blocks or tablets mixed with milk or water.

[0099] The snack food category generally refers to any food that can be a light informal meal, including but not limited to sweet and savory snacks and snack bars. Examples of snack foods include, but are not limited to, fruit snacks, chips / crisps, extruded snacks, tortilla / corn chips, popcorn, pretzels, nuts, and other sweet and savory snacks. Examples of snack bars include, but are not limited to, granola / muesli bars, breakfast bars, energy bars, fruit bars, and other snack bars.

[0100] The baked goods category generally refers to any edible product whose preparation method involves exposure to heat or excessive sunlight. Examples of baked goods include, but are not limited to, bread, buns, cookies, muffins, cereals, toaster pastries, pastries, waffles, tortillas, biscuits, pies, bagels, tarts, quiches, cakes, any baked food product, and any combination thereof.

[0101] The ice cream category generally refers to frozen desserts that contain cream and sugar and flavorings. Examples of ice cream include, but are not limited to, impulse ice cream; take-home ice cream; frozen yogurt and artisanal ice cream; soy, oat, bean (e.g., red bean and mung bean) and rice-based ice cream.

[0102] The confectionery category generally refers to sweet tasting edible products. Examples of confectionery include, but are not limited to, candy, gelatin, chocolate confectionery, sugar confectionery, gum, and the like, and any combination products.

[0103] The meal replacement category generally refers to any food product intended to replace a regular meal, especially for people with health or fitness concerns. Examples of meal replacements include, but are not limited to, slimming products and recovery products.

[0104] The ready meal category generally refers to any food that can be served as a meal without extensive cooking or processing. Ready meals include products to which recipe "skill" has been added by the manufacturer, resulting in a high degree of preparation, completion and convenience. Examples of ready meals include, but are not limited to, canned / preserved, frozen, dried, chilled ready meals; dinner mixes; frozen pizza; chilled pizza; and pre-prepared salads.

[0105] The pasta and noodles category includes any pasta and / or noodles, including but not limited to canned, dried and chilled / fresh pasta; regular, instant, chilled, frozen and snack noodles.

[0106] The canned / preserved foods category includes, but is not limited to, canned / preserved meat and meat products, fish / seafood, vegetables, tomatoes, beans, fruit, ready meals, soups, pasta and other canned / preserved foods.

[0107] The frozen processed foods category includes, but is not limited to, frozen processed red meat, processed poultry, processed fish / seafood, processed vegetables, meat substitutes, processed potatoes, bakery products, desserts, ready meals, pizza, soups, noodles and other frozen foods.

[0108] The dry processed food category includes, but is not limited to, rice, dessert mixes, dry ready meals, dehydrated soups, instant soups, dry pasta, regular noodles and instant noodles. The chilled processed food category includes, but is not limited to, chilled processed meats, processed fish / seafood products, lunch kits, fresh cut fruit, ready meals, pizza, prepared salads, soups, fresh pasta and noodles.

[0109] The sauces, dressings and condiments category includes, but is not limited to, tomato paste and purees, bouillon / stock cubes, herbs and spices, monosodium glutamate (MSG), table sauces, soy-based sauces, pasta sauces, wet / cooking sauces, dry sauces / powder mixes, ketchup, mayonnaise, mustard, salad dressings, vinaigrettes, dips, pickle products and other sauces, dressings and condiments.

[0110] Baby food categories include, but are not limited to, milk or soy-based formulas; cooked, dried and other baby foods.

[0111] Spread categories include, but are not limited to, jams and preserves, honey, chocolate spreads, nut-based spreads and yeast-based spreads.

[0112] The dairy category generally refers to edible products produced from mammalian milk. Examples of dairy products include, but are not limited to, drinking milk products, cheese, yogurt and sour milk drinks, and other dairy products.

[0113] Additional examples of flavored products, particularly food and beverage products or formulations, are provided below. Exemplary ingestible compositions include one or more of confectionery, chocolate confectionery, tablets, countlines, bagged selflines / softlines, boxed assortments, standard boxed assortments, twist wrapped miniatures, and the like. miniatures, seasonal chocolates, chocolates with toys, alfajores, other chocolate confectionery, mints, standard mints, power mints, boiled sweets, pastilles, gums, jellies and chews, toffees, caramel and nougat, medicated confectionery, lollipops, liquorice, other sugar confectionery, bread, packaged / industrial bread, unpackaged / artisan bread, pastries, cakes, packaged / industrial cakes, unpackaged / artisan cakes, cookies, chocolate coated biscuits, sandwich biscuits, filled biscuits, savoury biscuits and crackers, bread substitutes, breakfast cereals, rte cereals, family breakfast cereals, flakes, muesli, other cereals, children's breakfast cereals, hot cereals, ice cream, impulse ice cream, single portion dairy ice cream, single portion water ice cream, multi-pack dairy ice cream, marmalade Chipac water ice cream, take away ice cream, take away dairy ice cream, ice cream desserts, bulk ice cream, take away water ice cream, frozen yogurt, artisanal ice cream, dairy products, milk, raw milk / pasteurized milk, full fat raw milk / pasteurized milk, semi skimmed milk / pasteurized milk, long life / uht milk, full fat long life / uht milk, semi skimmed long life / uht milk, non fat long life / uht milk, goat milk, condensed milk / evaporated milk, plain condensed milk / evaporated milk, flavoured, functional and other condensed milk, flavoured milk drinks, dairy only flavoured milk drinks, flavoured dairy drinks with fruit juice, soy milk, sour milk drinks, fermented dairy drinks, coffee whitener, milk powder, flavoured milk powder drinks, cream, cheese, processed cheese, spreadable processed cheese, non spreadable processed cheese, raw cheese, spreadable raw cheese,Hard Cheese, Packaged Hard Cheese, Unpackaged Hard Cheese, Yogurt, Plain Yogurt / Natural Yogurt, Flavoured Yogurt, Fruit Yogurt, Probiotic Yogurt, Drinking Yogurt, Regular Drinking Yogurt, Probiotic Drinking Yogurt, Refrigerated Shelf Stable Desserts, Dairy Based Desserts, Soy Based Desserts, Chilled Snacks, Fromage Frais and Quark, Plain Fromage Frais and Quark, Flavoured Fromage Frais and Quark, Savory Fromage Frais and Quark, Sweet and Savory Snacks, Fruit Snacks, Chips / Crisps, Extruded Snacks, Tortilla / Corn Chips, Popcorn, Pretzels, Nuts, Other Sweet and Savory Snacks, Snack Bars, Granola Bars, Breakfast Bars, Energy Bars, Fruit Bars, Other Snack Bars, Meal Replacement Products, Slimming Products, Recovery Drinks, Ready Meals, Canned Ready Meals, Frozen Ready Meals, Dried Ready Meals, Chilled Ready Meals, Dinner Mixes, Frozen Pizza, Chilled Pizza, Soups, Canned Soups, Dehydrated Soups, Instant Soups, Chilled soup, Hot soup, Frozen soup, Pasta, Canned pasta, Dried pasta, Chilled / fresh pasta, Noodles, Regular noodles, Instant noodles, Cup / bowl instant noodles, Pouch instant noodles, Chilled noodles, Snack noodles, Canned food, Canned meat and meat products, Canned fish / seafood, Canned vegetables, Canned tomatoes, Canned beans, Canned fruit, Canned ready meals, Canned soup, Canned pasta, Other canned food, Frozen food, Frozen processed red meat, Frozen processed poultry, Frozen processed fish / seafood, Frozen processed vegetables, Frozen meat substitutes, Frozen potatoes, Oven baked potato chips, Other oven baked potato products, Oven Frozen Potatoes, Frozen Bakery Products, Frozen Desserts, Frozen Ready Meals, Frozen Pizza, Frozen Soups, Frozen Noodles, Other Frozen Foods, Dehydrated Foods, Dessert Mixes, Dehydrated Ready Meals, Dehydrated Soups, Instant Soups, Dehydrated Pasta, Plain Noodles, Instant Noodles, Cup / Bowl Instant Noodles, Pouch Instant Noodles, Chilled Foods, Chilled Processed Meat, Chilled Fish / Seafood Products, Chilled Processed Fish, Chilled Coated Fish, Chilled Smoked Fish, Chilled Lunch Kits, Chilled Ready Meals, Chilled Pizza, Chilled Soups, Chilled / Fresh Pasta, Chilled Noodles, Oils and Fats, Olive Oil, Vegetable Seed Oil,cooking fats and oils, butter, margarine, spreadable fats and oils, functional spreadable fats and oils, sauces, dressings and condiments, tomato paste and puree, bouillon / stock cubes, stock cubes, gravy granules, liquid stocks and fonds, herbs and spices, fermented sauces, soy based sauces, pasta sauces, wet sauces, dry sauces / powder mixes, ketchup, mayonnaise, regular mayonnaise, mustard, salad dressings, regular salad dressings, low fat salad dressings, vinaigrettes, dips, pickle products, other sauces, dressings and condiments, baby food, formulas, standard formulas, follow-on formulas, toddler formulas, hypoallergenic formulas, prepared baby foods, dry baby foods, other baby foods, spreads, jams and preserves, honey, chocolate spreads, nut based spreads, and yeast based spreads. Exemplary ingestible compositions include confectionery, bakery products, ice cream, dairy products, sweet and savory snacks, snack bars, meal replacement products, ready meals, soups, pastas, noodles, canned foods, frozen foods, dry foods, chilled foods, fats and oils, baby foods or spreads, or mixtures thereof. Exemplary ingestible compositions also include solid or liquid concentrate compositions for producing breakfast cereals, sweetened beverages, or beverages, ideally allowing for the reduction of the concentration of previously known sugar sweeteners or artificial sweeteners.

[0114] Some embodiments provide chewable compositions that may or may not be intended to be swallowed. In some embodiments, the chewable compositions may be gums, chewing gums, sugar gums, sugarless gums, functional gums, bubble gums, containing the compounds disclosed and described herein, individually or in combination.

[0115] In some embodiments, the taste-modifying compositions disclosed and described herein may be provided individually or in combination, for example, in a flavor concentrate formulation suitable for subsequent processing to produce a ready-to-use (i.e., ready-to-serve) product. By "flavor concentrate formulation" is meant a formulation to be reconstituted with one or more dilution media to become a ready-to-use composition. The term "ready-to-use composition" is used interchangeably herein with "ingestible composition", which means any substance that can be taken by mouth, whether or not it is intended for consumption, alone or together with another substance. In one embodiment, a ready-to-use composition includes a composition that can be directly consumed by a human or animal. A flavor concentrate formulation is typically used by mixing with or diluting with one or more dilution media, e.g., any consumable or ingestible ingredient or product, to impart or modify one or more flavors to the dilution medium. Such a method of use is often referred to as reconstitution. Reconstitution can be carried out in a domestic or industrial environment. For example, a frozen fruit juice concentrate can be reconstituted with water or other aqueous medium by a consumer in the kitchen to obtain a ready-to-use fruit juice beverage. In another example, soft drink syrup concentrates can be reconstituted with water or other aqueous media by manufacturers on a large industrial scale to produce ready-to-use soft drinks. Because flavor concentrate formulations have higher concentrations of flavoring agents or flavor modifiers than ready-to-use compositions, flavor concentrate formulations are typically not suitable for direct consumption without reconstitution. There are many benefits to the use and manufacture of flavor concentrate formulations. For example, one benefit is that flavor concentrate formulations can be reconstituted at the time of use by adding a suitable solvent, solid or liquid, thus reducing the weight and volume of shipping.

[0116] The flavored products according to any of the foregoing embodiments also, in certain embodiments, comprise one or more additional flavor modifying compounds, such as a compound that enhances sweetness, a compound that blocks bitterness, a compound that enhances umami, a compound that reduces sourness, a compound that enhances saltiness, a compound that enhances cooling effect, or any combination of the foregoing.

[0117] In certain embodiments of any of the aspects and embodiments described herein that refer to a sweetening or flavoring concentrate, the sweetening or flavoring concentrate is a composition that is specially manufactured for the production of a non-naturally occurring product, e.g., a flavored product, such as a food or beverage product.

[0118] In one embodiment, the flavor concentrate formulation comprises i) the compound disclosed and described herein, either individually or in combination, ii) a carrier, and iii) optionally at least one adjuvant. The term "carrier" refers to a normally inert accessory substance, such as a solvent, binder, or other inert vehicle, that is used in combination with the compound and one or more optional adjuvants to form a formulation. For example, water or starch can be a carrier for the flavor concentrate formulation. In some embodiments, the carrier is the same as the dilution medium for reconstituting the flavor concentrate formulation, and in other embodiments, the carrier is different from the dilution medium. The term "carrier" as used herein includes, but is not limited to, ingestibly acceptable carriers.

[0119] The term "adjuvant" refers to an additive that supplements, stabilizes, maintains or enhances the intended function or effectiveness of an active ingredient, such as a compound of the present invention. In one embodiment, the at least one adjuvant includes one or more flavoring agents. The flavoring agents may be of any flavor known to the artisan or consumer, such as the flavors of chocolate, coffee, tea, mocha, French vanilla, peanut butter, chai, or combinations thereof. In another embodiment, the at least one adjuvant includes one or more sweeteners. The one or more sweeteners may be any of the sweeteners described in this application. In another embodiment, the at least one adjuvant includes one or more ingredients selected from the group consisting of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, salts, and combinations thereof. Examples of emulsifiers, stabilizers, antimicrobial preservatives, antioxidants, vitamins, minerals, fats, starches, protein concentrates and isolates, and salts are described in U.S. Pat. No. 6,468,576, the contents of which are incorporated herein by reference in their entirety for all purposes.

[0120] In one embodiment, the flavor concentrate formulation may be in a form selected from the group consisting of liquids, including solutions and suspensions, solids, foams, pastes, gels, creams, and combinations thereof, such as liquids containing a certain amount of solids. In one embodiment, the flavor concentrate formulation is in the form of a liquid, including aqueous and non-aqueous. In some embodiments, the flavor concentrate formulation may be carbonated or non-carbonated.

[0121] The flavor concentrate formulation may further include a freezing point depressant, a nucleating agent, or both as at least one adjuvant. A freezing point depressant is a ingestibly acceptable compound or agent that can depress the freezing point of a liquid or solvent to which the compound or agent is added. That is, a liquid or solution containing a freezing point depressant has a lower freezing point than a liquid or solvent without the freezing point depressant. In addition to depressing the starting freezing point, the freezing point depressant can also reduce the water activity of the flavor concentrate formulation. Examples of freezing point depressants include, but are not limited to, carbohydrates, oils, ethyl alcohol, polyols such as glycerol, and combinations thereof. A nucleating agent refers to a ingestibly acceptable compound or agent that can promote nucleation. The presence of a nucleating agent in the flavor concentrate formulation can improve the texture of the frozen blushes of the frozen slush and help maintain the physical properties and performance of the slush at freezing temperatures by increasing the number of desirable ice crystallization centers. Examples of nucleating agents include, but are not limited to, calcium silicate, calcium carbonate, titanium dioxide, and combinations thereof.

[0122] In one embodiment, the flavor concentrate formulation is formulated to have a low water activity to extend shelf life. Water activity is the ratio of the vapor pressure of water in the formulation to the vapor pressure of pure water at the same temperature. In one embodiment, the flavor concentrate formulation has a water activity of less than about 0.85. In another embodiment, the flavor concentrate formulation has a water activity of less than about 0.80. In another embodiment, the flavor concentrate formulation has a water activity of less than about 0.75.

[0123] In one embodiment, the flavor concentrate formulation has the compound at a concentration at least twice as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 5 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 10 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 15 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 20 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 30 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 40 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration at least 50 times as high as the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration of at least 60 times the concentration of the compound in the ready-to-use composition. In one embodiment, the flavor concentrate formulation has the compound at a concentration of up to 100 times the concentration of the compound in the ready-to-use composition.

[0124] Treatment of diseased citrus fruits with the composition In one or more aspects, the disclosure provides a method of reducing the bitterness of a citrus composition derived from a citrus fruit having huanglongbing disease, the method comprising the steps of: (a) extracting the citrus composition from a citrus fruit at least in part having huanglongbing disease; and (b) introducing into the citrus composition a bitterness reducing composition comprising a taste-modifying composition of any of the preceding aspects or embodiments, e.g., in an amount having a bitterness-reducing effective amount of a PMF compound.

[0125] In some embodiments, the citrus composition comprises an abnormally high concentration of one or more bitter compounds, such as abnormally high levels of limonin or nomilin. In some embodiments, the bitter compound is a limonoid, such as limonin, nomilin, nomilic acid, or any combination thereof.

[0126] Blocking bitterness in pharmaceutical APIs Many drug compounds impart a bitter taste, which therefore limits the way in which they can be formulated and administered. Thus, in certain aspects, the present disclosure provides a pharmaceutical composition comprising a bitter tasting pharmacoactive ingredient and the taste modifying composition of any of the above aspects and embodiments. Such pharmaceutical compositions can be in any suitable form for oral administration, such as tablets, lozenges, capsules, powders, liquid solutions, liquid suspensions, etc. Such pharmaceutical compositions can include any suitable pharmaceutical excipients, binders, etc., such as those described in Remington's Pharmaceutical Sciences. In some embodiments, the bitter tasting pharmacoactive ingredient is an ion channel inhibitor, e.g., a proton channel inhibitor. Other examples of bitter tasting APIs whose bitterness is reduced by the taste-modifying compositions disclosed herein include, but are not limited to, atropine, brinzolamide, chloramphenicol, chloroquine, clindamycin, dexamethasone, digoxin, diltiazem, diphenhydramine, docusate, dorzolamide, doxepin, doxylamine, enalapril, erythromycin, esomeprazole, famotidine, gabapentin, ginkgolide A, guaifenesin, L-histidine, lomefloxacin, methylprednisolone, ofloxacin, oleuropein, oxyphenonium, pirenzepine, prednisone, ranitidine, trapidil, trimethoprim, and cetirizine.

[0127] Non-animal protein materials and products made therefrom Products intended to replace or substitute meat or dairy products often rely on a variety of non-animal based ingredients, such as starches, fibers and proteins derived from plants, algae, fungi or combinations thereof, to mimic the texture and flavor of meat or dairy products. Non-limiting examples of non-animal based proteins are plant proteins, such as soy protein, pea protein, bean protein, grain protein, potato protein, etc. Due to the compositional differences between such non-animal based ingredients and animal based ingredients, these products may have a bitter taste that consumers find unpleasant.

[0128] Thus, in certain aspects, the present disclosure provides a flavored product comprising a plant-based material (e.g., a plant-based starch, a plant-based fiber, a plant-based protein, or a combination thereof) and a taste-modifying composition disclosed herein. In some further embodiments, the flavored product can include any of the combinations of features described above for ingestible compositions containing a taste-modifying composition. In some embodiments, the flavored product is a beverage, such as soy milk, almond milk, rice milk, oat milk, a protein drink, a meal replacement drink, or other similar products. In some other embodiments, the flavored product is a meat replacement product, such as a plant-based chicken product (e.g., a plant-based chicken nugget), a plant-based beef product (e.g., a plant-based burger), or the like. In some other embodiments, the flavored product is a protein powder, a meal replacement powder, a plant-based creamer for coffee or tea, or the like. In certain further embodiments, any such product contains additional ingredients and has additional features typically used in the preparation and / or manufacture of such products. For example, such taste modifying compositions may be combined with other flavors and taste modifiers, or even encapsulated in specific materials, according to techniques known in the relevant art. Suitable concentrations of the taste modifying compositions are provided above.

[0129] In some embodiments, the flavored product comprises one or more plant-based proteins that impart a bitter taste that is at least partially reduced by the use of the taste-modifying composition in the product, including, but not limited to, pea protein, soy protein, canola (rapeseed) protein, chickpea protein, mycoprotein, algae protein, faba bean protein, sunflower protein, wheat protein.

[0130] In some alternative embodiments similar to those described above, algae or fungal proteins or starches are used instead, as well as oat protein, potato protein, and the like. In some embodiments, these flavored products also include fiber to provide texture to the product. Fibers suitable for use include, but are not limited to, psyllium fiber, pea fiber, potato fiber, curdlan, soluble corn fiber (dextran and / or maltodextrin), citrus fiber, and combinations thereof. In such products, the taste-modifying composition can be introduced in any suitable manner. In some embodiments, the taste-modifying composition is incorporated into a flavored emulsion, such as a water-in-oil emulsion, along with other flavor-imparting ingredients.

[0131] Non-meat protein materials and products made therefrom Certain non-meat animal proteins, such as dairy proteins and proteins from bone broth, are commonly used in food products and are also sold as the main ingredient of certain protein powders. Such proteins can impart a bitter taste that consumers may not want. This is particularly true for protein isolates, such as whey protein, collagen protein, casein protein, and other protein isolates. Thus, the present disclosure provides an ingestible composition comprising a non-meat animal protein and a taste-modifying composition. In some embodiments, the non-meat animal protein is a bone protein, such as collagen protein, derived from the bones of animals, such as cows, pigs, donkeys, horses, chickens, ducks, goats, geese, rabbits, lambs, sheep, buffalo, ostriches, camels, and the like. In some embodiments, the non-meat animal protein is a milk protein, such as whey protein, casein protein, or any combination thereof. The milk can be the milk of any suitable animal, such as cows, donkeys, horses, sheep, buffalo, camels, and the like.

[0132] The taste-modifying compositions can also be included in certain food or beverage products that contain animal milk or ingredients derived from animal milk, such as cheese, cheese spreads, yogurt, kefir, milk, processed dairy products, cottage cheese, sour cream, butter, etc. EXAMPLES

[0133] The following examples are included to further illustrate the present invention. Of course, the examples should not be construed as specifically limiting the present invention. Variations of these examples within the scope of the claims are within the scope of those skilled in the art and are considered to be within the scope of the invention described and claimed herein. The reader will recognize that, armed with this disclosure, those skilled in the art can prepare and use the present invention without the exhaustive examples.

[0134] Example 1 - Synthesis Method Step 1 - Extraction Citrus Valencia peel oil distillation residue (490.4 g) was mixed with 50% (w / w) aqueous ethanol (2500 g) by stirring at 350 rpm for 3 hours. The top layer of the aqueous ethanol extract was separated from the bottom sediment and filtered through a membrane filter (0.45 μm) to remove the insoluble components. 2650 grams of extract solution was obtained.

[0135] A portion of the extract solution (100.0 g) was concentrated using a rotary evaporator and then freeze-dried in a freeze dryer. The dried extract (3.2 g) was stored at 4°C for chemical composition analysis. This sample was designated as Sample 1A.

[0136] Step 2 - Adsorption Chromatography Adsorption chromatographic purification of the extracted flavonoids was performed using a flash chromatography system (Agela Technologies, FLEXA) equipped with a flash column packed with macroporous resin or MCI gel. The resin was first activated with 95% ethanol and then conditioned with deionized water.

[0137] Then, 300 g of the extraction solution from step 1 was loaded onto the top of a flash column (80 g, 150 mL, ID 3.12 cm × H. 19.5 cm) packed with MCI gel (Mitsubishi Chemical Corporation, CHP20) at a flow rate of 5 mL / min. After adsorption, desorption was carried out using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 8 column volumes. The collected fractions (1st to 8th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis. This sample is designated as sample 2A.

[0138] Then, 300 g of the extraction solution from step 1 was loaded onto the top of a flash column (120 g, 215 mL, ID 3.66 cm × H. 20.4 cm) packed with AB-8 resin at a flow rate of 5 mL / min. After adsorption, desorption was performed using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 5 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (1st to 10th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis. This sample is designated as sample 2B.

[0139] Then, 300 g of the extraction solution from step 1 was loaded onto the top of a flash column (120 g, 215 mL, ID 3.66 cm × H. 20.4 cm) packed with D101 resin at a flow rate of 5 mL / min. After adsorption, desorption was carried out using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (1st to 10th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis. This sample is designated as sample 2C-1.

[0140] The D101 resin after the first cycle of separation was regenerated with dilute sodium hydroxide solution (0.5% w / v) and then 95% ethanol. The ethanol was washed thoroughly with deionized water. Then, 300 g of the extraction solution from step 1 was loaded onto the top of the flash column packed with D101 resin at a flow rate of 5 mL / min (second cycle of separation). After adsorption, desorption was performed using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (1st to 10th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis. This sample is designated as sample 2C-2.

[0141] Then, 300 g of the extraction solution from step 1 was loaded onto the top of a flash column (120 g, 215 mL, ID 3.66 cm × H. 20.4 cm) packed with HP20 resin at a flow rate of 5 mL / min. After adsorption, desorption was carried out using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (1st to 10th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis. This sample is designated as sample 2D-1.

[0142] The HP20 resin after the first cycle of separation was regenerated with 95% aqueous ethanol (w / w) and pure acetone. The acetone was thoroughly washed with 95% aqueous ethanol (w / w). The column was conditioned with deionized water. Then, 300 g of the extract from step 1 was loaded onto the top of the flash column packed with HP20 resin at a flow rate of 5 mL / min (second cycle of separation). After adsorption, desorption was carried out using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (2nd to 10th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis. This sample is designated as sample 2D-2.

[0143] The HP20 resin after the second cycle of separation was regenerated with 95% aqueous ethanol (w / w) and pure acetone. The acetone was thoroughly washed with 95% aqueous ethanol (w / w). The column was conditioned with deionized water. Then, 300 g of the extract from step 1 was loaded onto the top of the flash column packed with HP20 resin at a flow rate of 5 mL / min (third cycle of separation). After adsorption, desorption was carried out using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (2nd to 10th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis. This sample is designated as sample 2D-3.

[0144] The HP20 resin after the third cycle of separation was regenerated with 95% aqueous ethanol (w / w) and pure acetone. The acetone was thoroughly washed with 95% aqueous ethanol (w / w). The column was conditioned with deionized water. Then, 300 g of extract derived from another batch of orange peel oil distillation residue was loaded onto the top of the flash column packed with HP20 resin at a flow rate of 5 mL / min (fourth cycle of separation). After adsorption, desorption was carried out first using 50% aqueous ethanol (w / w) and then using 65% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (50% of the second to tenth bed volumes and 65% of the first to tenth bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product (50% of the second to tenth bed volumes) was designated as sample 2D-4.

[0145] Then, 300 g of the extraction solution from step 1 was loaded onto the top of a flash column (120 g, 215 mL, ID 3.66 cm × H. 20.4 cm) packed with XAD1600 resin at a flow rate of 5 mL / min. After adsorption, desorption was carried out using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (1st to 10th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis. This sample is designated as sample 2E.

[0146] Then, 300 g of the extraction solution from step 1 was loaded onto the top of a flash column (120 g, 215 mL, ID 3.66 cm × H. 20.4 cm) packed with XAD4 resin at a flow rate of 5 mL / min. After adsorption, desorption was carried out using aqueous ethanol of different concentrations (50%, 55% and 65%) successively. The constant flow rate of the mobile phase was 10 mL / min. The elution volume was kept at 10 column volumes for the 50% aqueous ethanol eluate and 5 column volumes for the 55% and 65% aqueous ethanol eluates. The collected fractions (1st to 10th bed volumes 50% and 1st to 5th bed volumes 55%) were concentrated using a rotary evaporator and then dried using a freeze dryer. The dried product was stored at 4 °C for chemical composition analysis, which is designated as sample 2F.

[0147] Step 3 - Base Wash The dried product from step 2 (Sample 2D-2) was treated with dilute sodium hydroxide (5% w / v) by stirring at 350 rpm at 80° C. for 2 hours. The insoluble components were collected, dissolved in ethyl acetate, washed twice using deionized water, and then dried to form the product (Sample 3A).

[0148] Citrus Pera oil distillation residue (518.11 g) was mixed with 50% (w / w) aqueous ethanol (2590 g) by stirring at 350 rpm for 3 h at room temperature. The top layer of the ethanol extract aqueous solution was separated from the bottom sediment and filtered through a membrane filter (0.25 μm) to remove the insoluble components. Then, 2590 g of extract solution was obtained. First, a small amount (100.0 g) of the extract solution was concentrated using a rotary evaporator and further freeze-dried in a freeze dryer. The dried extract (sample 4A, 3.225 g) was stored at 4 °C for chemical composition analysis. Then, 300 g of the extract solution was loaded onto the top of a flash column (220 g, 377 mL, ID 60.6 mm × H. 13.1 mm) packed with HP20 resin at a flow rate of 10 mL / min. After adsorption, desorption was carried out using 50% aqueous ethanol (w / w). The constant flow rate of the mobile phase was 20 mL / min. The elution volume was kept at 10 column volumes. The collected fractions (2nd to 10th bed volumes) were concentrated using a rotary evaporator and then dried using a freeze dryer. 100 mg of the dried product (sample 5D-1) was then stored at 4°C for chemical composition analysis. The remaining dried product, sample 5D-1, was treated with dilute sodium hydroxide (5% w / v) by stirring at 350 rpm, 80°C for 2 hours. The insoluble components were collected, dissolved in ethyl acetate, washed twice using deionized water, and then dried to form the product (sample 6A).

[0149] Analysis method The PMFs were mainly composed of six PMFs listed in Table 1. These six individual PMFs were isolated from orange peel oil distillation residue and used as external standards, and their structures were identified as sinensetin (SIN, CAS number 2306-27-6), hexa-O-methylquercetagetin (HMQ, CAS number 1251-84-9), nobiletin (NOB, CAS number 478-01-3), TOM-scutellarein (TMS, CAS number 1168-42-9), heptamethoxyflavone (HMF, CAS number 1178-24-1) and tangeretin (TAN, CAS number 481-53-8), and their purity (>95%) was confirmed by NMR and LCMS analysis. The major components of hydroxy-substituted flavonoids were their demethyl derivatives. Six of them were isolated from the mixture and determined to be 5-demethylsinensetin (5OHSIN, CAS no. 21763-80-4), 5-demethylHMQ (5OHHMQ, CAS no. 479-90-3), 5-demethylnobiletin (5OHNOB, CAS no. 2174-59-6), 5-demethylTMS (5OHTMS, CAS no. 19103-54-9), 5-demethylheptamethoxyflavone (5OHHMF, CAS no. 1176-88-1), and 5-demethyltangeretin (5OHTAN, CAS no. 2798-20-1). The other minor products were determined to be their hydroxy- or methoxy-isomers. The products were quantitatively analyzed using a reversed-phase method with a RP18 column (Luna C18(2), 150*2.0mm×3μm) and a UV detector. Calibration curves were obtained by running multiple standard solutions on an Agilent UPLC system equipped with a PDA detector. The flavonoid contents in all samples on a dry basis were determined and are shown in Table 2.

[0150] [Table 2]

[0151] Example 2 - Sensory testing Certain PMF compositions were taste tested by a human sensory panel to assess their off-note potency. The panel consisted of seven trained panelists who evaluated the samples at 5 ppm concentration on a scale of 0 to 10, with 0 indicating no off-notes and 10 indicating strong off-notes. The results are listed in Table 3. The off-note intensity decreased after each step of the method.

[0152] [Table 3]

Claims

1. 1. A method for concentrating polymethoxylated flavonoids, comprising: (a) providing an organic oil comprising polymethoxylated flavonoids and hydroxyl-substituted flavonoids, wherein the concentration of polymethoxylated flavonoids in the organic oil is 30% by weight or less, based on the total weight of the organic oil; (b) introducing an extraction medium into the organic oil to form a mixture having an aqueous phase and an organic phase, wherein the extraction medium is water and C １～６ a step of: (c) separating at least a portion of the aqueous phase from the organic phase; (d) generating two or more fractions of the separated aqueous phase using adsorption chromatography, wherein at least one of the two or more fractions comprises polymethoxylated flavonoids or both polymethoxylated flavonoids and hydroxyl-substituted flavonoids at a concentration of at least 85% by weight on a dry weight basis; A method comprising:

2. The method of claim 1 , wherein the polymethoxylated flavonoid is a flavone.

3. 3. The method of claim 2, wherein the polymethoxylated flavonoid is selected from the group consisting of sinensetin, hexamethoxyquercetagetin, nobiletin, tetramethoxyscutellarein, heptamethoxyflavone, tangeretin, and any combination thereof.

4. (e) washing said at least one of said two or more fractions with an alkaline aqueous solution. The method of any one of claims 1 to 3, further comprising:

5. A taste-modifying composition comprising one or more polymethoxylated flavonoids and one or more hydroxyl-substituted flavonoids, comprising a concentration of at least 85% by weight of polymethoxylated flavonoids, or both polymethoxylated flavonoids and hydroxyl-substituted flavonoids, on a dry weight basis.

6. The taste-modifying composition of claim 5 , wherein the polymethoxylated flavonoid is a flavone.

7. 7. The taste-modifying composition of claim 6, wherein the polymethoxylated flavonoid is selected from the group consisting of sinensetin, hexamethoxyquercetagetin, nobiletin, tetramethoxyscutellarein, heptamethoxyflavone, tangeretin, and any combination thereof.

8. 8. The taste-modifying composition of any one of claims 5 to 7, wherein the weight ratio of polymethoxylated flavonoids to hydroxy-substituted flavonoids in the composition is at least 9:

1.

9. 9. Use of the taste-modifying composition of any one of claims 5 to 8 to (a) enhance sweetness, (b) reduce bitterness, or (c) reduce sourness, (d) reduce astringency, or (e) enhance the texture of an ingestible composition.

10. An ingestible product comprising the taste-modifying composition of any one of claims 5 to 8.

11. A flavored product comprising the ingestible composition of claim 10.

12. 12. The flavored product of claim 11 which is a food or beverage product.

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