Process for the manufacture of hop-like bitter beverages and hop-like bitter beverages

Abstract

A process for the manufacture of beverages having a hop-like bitterness or for the hop-like bittering of beverages. The process includes adding to a beverage base at least one of: andrographolide, foliamenthin, menthiafolin, dihydrofoliamenthin, including derivatives thereof, at a concentration of from about 0.1 ppm to about 50 ppm. Use of at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin as a hop-like bittering agent in a beverage. A method for replacing or reducing the amount of hop-derived ingredients in a beverage without the concomitant reduction in hop-like bitterness including adding at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm.

Description

[0001] HOP-LIKE BITTER BEVERAGES

[0002] TECHNICAL FIELD

[0003] The present disclosure relates generally to methods for making hop-like bitter beverages or for the hop-like bittering of beverages, in some cases, with no or a reduced amount of hop-derived ingredients. The present disclosure further relates to compositions and beverages comprising hoplike bittering materials. The present disclosure further relates methods for reducing or replacing hop-derived bittering substances, such as hop extracts and iso-alpha hop acids, in a beverage, such as a beer, without the concomitant reduction in hop-like organoleptic profile, in particular, hoplike bitterness profile.

[0004] BACKGROUND

[0005] Hops (Humulus lupulus / .. ) is a species of flowering plant in the hemp family Cannabaceae, native to West Asia, Europe and North America. As the female cone-shaped flowers (hops) are used to preserve and flavor beer, the species is widely cultivated for the brewing industry. Hops contain alpha acids, such as humulone, cohumulone and adhumulone, which are the source of bitterness in beer, and when boiled, they isomerize into iso-alpha acids which are about 5 times more bitter and provide a more balanced bitterness profile, as compared to non-isomerized alpha acids. However, hops and hop extracts are expensive and both the supply and quality is threatened by bad weather and seasonal changes.

[0006] Accordingly, there is a need for making hop-like bitter beverages having no or a reduced amount of hop-derived ingredients. Cheaper and more readily available bittering agents, such as quinine (Chinchona bark), quassin (Quassia bark), amarogentin and gentiopicrin (gentian root), and naringin (Citrus species) do not have a similar bitterness profile as hops-derived ingredients, and also impart undesirable character when used in beer and beverages normally flavoured with hops-derived ingredients. The present disclosure seeks to address these needs and others. SUMMARY

[0007] In accordance with a first aspect of the present disclosure, there is provided a method for the manufacture of beverages having a hop-like bitterness or for the hop-like bittering of beverages, which process comprises adding to a beverage base at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof, at a concentration of from about 0.1 ppm to about 50 ppm.

[0008] In certain embodiments, the method of the first aspect of the present disclosure further comprises fermenting the beverage.

[0009] In certain embodiments, the method of the first aspect of the present disclosure further comprises adding hop-derived ingredients to the beverage base. In some cases, the hop-derived ingredients comprise hop extract or components thereof, such as alpha acids, including isomerized alpha acids (also referred to as iso-alpha hop acids).

[0010] In accordance with a second aspect of the present disclosure, there is provided a beverage having a hop-like bitterness obtainable by and / or obtained by the method of the first aspect of the present disclosure, including any embodiment thereof.

[0011] In certain embodiments, the beverage of the second aspect of the present disclosure comprises beer, non-alcoholic beer, beer-type beverages, or carbonated soft drinks.

[0012] In certain embodiments, the beverage of the second aspect of the present disclosure is substantially free of iso-alpha hop acids.

[0013] In certain embodiments, the beverage of the second aspect, or any other aspect, of the present disclosure is substantially free of quinine (Chinchona bark), quassin (Quassia bark), amarogentin and / or gentiopicrin (gentian root).

[0014] In accordance with a third aspect of the present disclosure, there is provided the use of at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof, as a hop-like bittering agent in a beverage.

[0015] In accordance with a fourth aspect of the present disclosure, there is provided a method of imparting hop-like bitterness to a beverage, the method comprising adding at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof, to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm.

[0016] In accordance with a fifth aspect of the present disclosure, there is provided a method for replacing or reducing the amount of hop-derived ingredients, such as hop extract, in a beverage without the concomitant reduction in bitterness impact, the method comprising adding at least one of: andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof, to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm.

[0017] In accordance with a sixth aspect of the present disclosure, there is provided a flavour composition comprising at least one of: andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof, which is effective in mimicking the organoleptic properties of hop-derived ingredients, such as hop extract and alpha hop acids, including isomerized alpha hop acids, when the andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof, is present at a concentration of from about 0.1 ppm to about 50 ppm in a beverage.

[0018] These and other features, aspects and advantages of specific embodiments will become evident to those skilled in the art from a reading of the present disclosure.

[0019] BRIEF DESCRIPTION OF DRAWINGS

[0020] FIGURE l is a radar diagram generated from the results of a CATA (Check All That Apply) study showing that the sensory attributes of a beverage containing hop derivatives, such as a hop extract (solid line) and isomerized hop alpha acid (broken line) is similar .

[0021] FIGURE 2 is a radar diagram generated from the results of a CATA study showing that the sensory attributes of isomerized hop alpha acid are very different from a gentian root extract (which is a common bittering agent).

[0022] FIGURE 3 is a radar diagram generated from the results of a CATA study showing that the sensory attributes of a reference beer with added hop extract (solid line) is very similar to the reference beer with different concentrations of added Andrographis extract (broken lines). FIGURE 4 is a radar diagram generated from the results of a CATA study showing that the sensory attributes of a reference beer with added hop extract (solid line) is very similar to the reference beer with different concentrations of Menyanthes (Bogbean) extract (broken lines).

[0023] FIGURE 5 is a radar diagram generated from the results of a CATA study showing that the sensory attributes of a beverage base containing added hop extract (solid line) are very similar to the sensory attributes of the beverage base containing added Andrographis extract (broken line).

[0024] FIGURE 6 is a radar diagram generated from the results of a CATA study showing that the sensory attributes of a beverage base containing added hop extract (solid line) are very different to the sensory attributes of the beverage base containing added quinine (a common bittering substance).

[0025] FIGURE 7 is a radar diagram generated from the results of a CATA study showing that the sensory attributes of a beverage base containing added hop extract (solid line) are very different to the sensory attributes of the beverage base containing added quassia extract (a common bittering substance).

[0026] FIGURE 8 is a radar diagram generated from the results of a CATA study showing that the sensory attributes of a beverage base containing a 50:50 mixture of hop extract and Andrographis extract (broken line) are almost identical to the sensory attributes of the beverage base containing added hop extract alone (solid line).

[0027] DETAILED DESCRIPTION

[0028] Disclosed is a process for the manufacture of beverages having a hop-like bitterness or for the hop-like bittering of beverages, which process comprises adding to a beverage base at least one of: andrographolide, foliamenthin, menthiafolin, dihydrofoliamenthin, including derivatives thereof, at a concentration of from about 0.1 ppm to about 50 ppm. It has been found that andrographolide, foliamenthin, menthiafolin and / or dihydrofoliamenthin, including derivatives thereof, can impart bitterness with an organoleptic profile very similar to hop-derived ingredients, such as hop extract and iso-alpha hop acids, thus improving the enjoyment of beer, non-alcoholic beer, and beer-type beverages with the advantage of a consistent and sustainable source of bitterness.

[0029] In certain embodiments, the methods and compositions disclosed herein include a bittering agent consisting of at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof. In other embodiments, the methods and compositions disclosed herein may include at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin in combination with further bittering agents, such as hop- derived bittering ingredients, for example, hop extract and iso-alpha hop acids.

[0030] It has been found that at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof are useful to mimic the hop-like bitterness profile of beer and beer-type beverages and can be used to impart a hop-like bitterness to replace part or all of hop-derived ingredients either alone or in combination with hop extracts or other natural extracts. As used herein, beer-type beverages include IPA’s, pilsners, ales, lagers, stouts, porters, wheat beers, pale ales, German bocks, all of the foregoing may be alcoholic or nonalcoholic.

[0031] As used herein, hop-like bitterness refers to a bitterness profile that mimics the bitterness profile of a hops extract, including components thereof, such as alpha acids, including isomerized alpha acids. Hop-like bitterness may easily be determined by well-established methods and techniques. For example, hop-like bitterness may be determined in accordance with a CATA (Check All That Apply) methodology, which is a method used in sensory evaluation to understand consumer perceptions of a product or experience. It involves presenting participants with a list of attributes or descriptors related to the product, and asking them to check all the options that they believe apply to the product they are evaluating. CATA is a reliable and proven approach for sensory product characterization and is a widely used technique in sensory science to gather information about how consumers perceive the sensory attributes of products (e.g., taste, texture, aroma). In some cases, CATA may include the following steps: 1. A list of organoleptic descriptors is provided to panelists. 2. Panelists are instructed to check all the options that apply to them. They are not limited to selecting just one or a few options, but can choose as many as they feel are relevant. 3. Data analysis is then conducted to understand the frequency and patterns of selections. In certain embodiments, hop-like bitterness refers to an overall organoleptic profile that mimics the overall organoleptic profile of a hop extract, including components thereof, such as alpha acids, including isomerized alpha acids.

[0032] Andrographolide is a labdane diterpenoid having a chemical formula of C20H30O5 and is represented by the compound according to Formula (I), shown below.

[0033] Formula (I)

[0034] The chemical name of andrographolide is 3a, 14, 15, 18-tetrahydroxy-5 ?, 9 / >H, lOa-labda- 8, 12-dien- 16-oic acid y-lactone. The structure of andrographolide has been analyzed by using X- ray, 1H,13 C-NMR, and ESI-MS. While andrographolide is sparingly soluble in water, it is soluble in acetone, chloroform, ether, and hot ethanol.

[0035] Andrographolide has not been used in beverages, in particular beer-type beverages, at the concentrations disclosed herein to achieve a hop-like bitterness. As demonstrated by the examples, it has been found that andrographolide surprisingly mimics the bitterness profile of hop-derived ingredients, such as alpha acids and iso-alpha acids, when present in a beverage at a concentration of from about 0.1 ppm to about 50 ppm. As also demonstrated by the examples, it has been found that andrographolide surprisingly mimics the overall organoleptic profile of hop-derived ingredients, such as alpha acids and iso-alpha acids, when present in a beverage at a concentration of from about 0.1 ppm to about 50 ppm. Andrographolide can be derived from one or more botanical sources, such as a plant of the genus Andrographis (e.g., Andrographus paniculata), or can be synthetic, or can be a combination of natural extract and synthetic.

[0036] Extracts may be obtained by any method known in the art. In certain embodiments, andrographolide may be obtained by extraction of Andrographis leaf powder by cold maceration in a 1 : 1 mixture of dichloromethane and methanol, and isolation of andrographolide directly from the resulting extract by recrystallisation. The identity of andrographolide can be confirmed through IR, UV, mass and melting point, and co-chromatography with a reference standard on TLC. The purity of andrographolide can be confirmed by TLC, UV absorption spectrum, HPLC, LC-MS, and differential scanning calorimetry.

[0037] In some cases, supercritical fluid extraction employing CCh-ethanol mixture as solvent is used to extract andrographolide from dried material of A. paniculata.

[0038] In certain embodiments, an extract is obtained by extracting dried A. paniculata material with a polar solvent, such as hot water, methanol, ethanol, or mixtures thereof, in particular a mixture of methanol and water, or a mixture of ethanol and water. Extraction can be achieved by several means well-known to those of ordinary skill in the art, such as steeping and filtration or by flow-through extraction systems. Extraction can be achieved across a range of temperatures at which the solvents are liquid, typically ambient temperature (20°C) or slightly elevated temperatures in a range of from about 20° to about 100°C. In certain embodiments, the weight to volume ratio is in the range of about 1 :5 to about 1 : 10 with the extraction time, flow rate, temperature and pressure adjusted according to the equipment used.

[0039] In some cases, the crude extract of A. paniculata material is subjected to a purification treatment. Purification of the crude extract can be achieved by several means. In certain embodiments, the crude extract is purified via sequential precipitation or crystallization from hot water whereby the crude extract is dissolved in hot water (with or without small amounts of ethanol, methanol, or other modifier) and then cooled to induce precipitation and crystallization followed by filtration to obtain the solid material which can be further purified by iterations of the same process. According to certain illustrative embodiments, the crude extract is purified via fractionation on an ion exchange resin (e.g. sephadex resin, HP-20 or DA101) or a C18 silica column or similar product using a water-methanol mixture in a gradient from 100% water to 100% methanol, or a water-ethanol mixture in a gradient from 100% water to 100% ethanol.

[0040] In certain embodiments, the methods and compositions disclosed herein use an Andrographis extract fraction comprising greater than 30% andrographolide, greater than 40% andrographolide, greater than 50% andrographolide, greater than 60% andrographolide, greater than 70% andrographolide, greater than 80% andrographolide, greater than 90% andrographolide, or about 100% andrographolide. In certain embodiments, the methods and compositions disclosed herein use an Andrographis extract fraction comprising about 70% to about 80% andrographolide.

[0041] In certain embodiments, andrographolide may be synthesized via enantioselective total synthesis using an iridium-catalyzed carbonyl reductive coupling to form the key quaternary carbon stereocenter at C4, followed by a diastereoselective alkene reduction to establish the transdecalin ring, and finally a carbonylative lactonization to install the characteristic a-alkylidene-P- hydroxy-y-butyrolactone moiety.

[0042] Dosage of andrographolide or an extract comprising andrographolide in a flavour composition and subsequent dosage in the final beverage is adapted according to the desired degree of bittering and the concentration of andrographolide in the extract in a manner well known to those of ordinary skill in the art. As demonstrated by the examples, it has been found that adding andrographolide to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm mimics the bitterness profile of hop-derived ingredients, such as alpha acids.

[0043] Foliamenthin is represented by the compound according to Formula (II), shown below.

[0044] Formula (II) Foliamenthin is a secoiridoid compound, containing a complex ring system with multiple hydroxyl groups attached. The two isomeric forms of foliamenthin are described as Exaltoside and 7-epiexaltoside. Foliamenthin be derived from one or more botanical sources, such as plants of the family Menyanthaceae (e.g., Menyanlhes trifoliata, Villarsia exaltata), or can be synthetic, or can be a combination of natural extract and synthetic.

[0045] In certain embodiments, an extract is obtained by extracting dried Menyanlhes trifoliata material with a polar solvent, such as hot water, methanol, ethanol, or mixtures thereof, in particular a mixture of methanol and water, or a mixture of ethanol and water. Extraction can be achieved by several means well known to those of ordinary skill in the art, such as steeping and filtration or by flow-through extraction systems. Extraction can be achieved across a range of temperatures at which the solvents are liquid, typically ambient temperature (20°C) or slightly elevated temperatures in range of from about 20° to about 100°C. In certain embodiments, the weight to volume ratio is in the range of about 1 :5 to about 1 : 10 with the extraction time, flow rate, temperature and pressure adjusted according to the equipment used.

[0046] In some cases, the crude extract is subjected to a purification treatment. Purification of the crude extract can be achieved by several means. In certain embodiments, the crude extract is purified via sequential precipitation or crystallization from hot water whereby the crude extract is dissolved in hot water (with or without small amounts of ethanol, methanol, or other modifier) and then cooled to induce precipitation and crystallization followed by filtration to obtain the solid material which can be further purified by iterations of the same process. According to certain illustrative embodiments, the crude extract is purified via fractionation on an ion exchange resin (e.g. sephadex resin, HP-20 or DA101) or a C18 silica column or similar product using a watermethanol mixture in a gradient from 100% water to 100% methanol, or a water-ethanol mixture in a gradient from 100% water to 100% ethanol.

[0047] In certain embodiments, the methods and compositions disclosed herein use a Menyanlhes extract fraction comprising greater than 30% foliamenthin, greater than 40% foliamenthin, greater than 50% foliamenthin, greater than 60% fohamenthin, greater than 70% fohamenthin, greater than 80% foliamenthin, greater than 90% foliamenthin, or about 100% foliamenthin.

[0048] Dosage of foliamenthin or an extract comprising foliamenthin in a flavour composition and subsequent dosage in the final beverage is adapted according to the desired degree of bittering and the concentration of foliamenthin in the extract in a manner well known to those of ordinary skill in the art. It has been found that adding foliamenthin to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm mimics the bitterness profile of hop-derived ingredients, such as alpha acids.

[0049] Dihydrofoliamenthin is represented by the compound according to Formula (III), shown below.

[0050] Formula (III)

[0051] Dihydrofoliamenthin be derived from one or more botanical sources, such as a plant of the genus Menyctnlhes (e.g., Menyctnlhes trifoliata), or can be synthetic, or can be a combination of natural extract and synthetic.

[0052] In certain embodiments, an extract is obtained by extracting dried Menyanlhes trifoliata material with a polar solvent, such as hot water, methanol, ethanol, or mixtures thereof, in particular a mixture of methanol and water, or a mixture of ethanol and water. Extraction can be achieved by several means well known to those of ordinary skill in the art, such as steeping and filtration or by flow-through extraction systems. Extraction can be achieved across a range of temperatures at which the solvents are liquid, typically ambient temperature (20°C) or slightly elevated temperatures in range of from about 20° to about 100°C. In certain embodiments, the weight to volume ratio is in the range of about 1 :5 to about 1 : 10 with the extraction time, flow rate, temperature and pressure adjusted according to the equipment used.

[0053] In some cases, the crude extract is subjected to a purification treatment. Purification of the crude extract can be achieved by several means. In certain embodiments, the crude extract is purified via sequential precipitation or crystallization from hot water whereby the crude extract is dissolved in hot water (with or without small amounts of ethanol, methanol, or other modifier) and then cooled to induce precipitation and crystallization followed by filtration to obtain the solid material which can be further purified by iterations of the same process. According to certain illustrative embodiments, the crude extract is purified via fractionation on an ion exchange resin (e.g. sephadex resin, HP-20 or DA101) or a C18 silica column or similar product using a watermethanol mixture in a gradient from 100% water to 100% methanol or a water-ethanol mixture in a gradient from 100% water to 100% ethanol.

[0054] In certain embodiments, the methods and compositions disclosed herein use an Menyanthes extract fraction comprising greater than 30% dihydrofoliamenthin, greater than 40% dihydrofoliamenthin, greater than 50% dihydrofoliamenthin, greater than 60% dihydrofoliamenthin, greater than 70% dihydrofoliamenthin, greater than 80% dihydrofoliamenthin, greater than 90% dihydrofoliamenthin, or about 100% dihydrofoliamenthin.

[0055] Dosage of dihydrofoliamenthin or an extract comprising dihydrofoliamenthin in a flavour composition and subsequent dosage in the final beverage is adapted according to the desired degree of bittering and the concentration of dihydrofoliamenthin in the extract in a manner well known to those of ordinary skill in the art. It has been found that adding dihydrofoliamenthin to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm mimics the bitterness profile of hop-derived ingredients, such as a hop extract, alpha acids.

[0056] Menthiafolin is represented by the compound according to Formula (IV), shown below.

[0057]

[0058] Formula (IV)

[0059] Menthiafolin is a complex molecule with a chemical structure characterized as a secoiridoid glycoside, containing a fused cyclopentane-pyran ring system with multiple hydroxyl groups, a sugar moiety (glucose), and a side chain with a double bond.

[0060] Menthiafolin can be derived from one or more botanical sources, such as a plant of the genus Menyctnlhes (e.g., Menyctnlhes trifoliata), or can be synthetic, or can be a combination of natural extract and synthetic.

[0061] In certain embodiments, an extract is obtained by extracting dried Menyanlhes trifoliata material with a polar solvent, such as hot water, methanol, ethanol, or mixtures thereof, in particular a mixture of methanol and water, or a mixture of ethanol and water. Extraction can be achieved by several means well known to those of ordinary skill in the art, such as steeping and filtration or by flow-through extraction systems. Extraction can be achieved across a range of temperatures at which the solvents are liquid, typically ambient temperature (20°C) or slightly elevated temperatures in range of from about 20° to about 100°C. In certain embodiments, the weight to volume ratio is in the range of about 1 :5 to about 1 : 10 with the extraction time, flow rate, temperature and pressure adjusted according to the equipment used.

[0062] In some cases, the crude extract is subjected to a purification treatment. Purification of the crude extract can be achieved by several means. In certain embodiments, the crude extract is purified via sequential precipitation or crystallization from hot water whereby the crude extract is dissolved in hot water (with or without small amounts of ethanol, methanol, or other modifier) and then cooled to induce precipitation and crystallization followed by filtration to obtain the solid material which can be further purified by iterations of the same process. According to certain illustrative embodiments, the crude extract is purified via fractionation on an ion exchange resin (e.g. sephadex resin, HP-20 or DA101) or a C18 silica column or similar product using a watermethanol mixture in a gradient from 100% water to 100% methanol, or a water-ethanol mixture in a gradient from 100% water to 100% ethanol.

[0063] In certain embodiments, the methods and compositions disclosed herein use an Menyanthes extract fraction comprising greater than 30% menthiafolin, greater than 40% menthiafolin, greater than 50% menthiafolin, greater than 60% menthiafolin, greater than 70% menthiafolin, greater than 80% menthiafolin, greater than 90% menthiafolin, or about 100% menthiafolin.

[0064] Dosage of menthiafolin or an extract comprising menthiafolin in a flavour composition and subsequent dosage in the final beverage is adapted according to the desired degree of bittering and the concentration of menthiafolin in the extract in a manner well known to those of ordinary skill in the art. It has been found that adding menthiafolin to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm mimics the bitterness profile of hop-derived ingredients, such as alpha acids.

[0065] Products

[0066] At least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof, when used at the concentrations disclosed herein may be used directly as such without undergoing any further processing.

[0067] The at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin described herein may be used directly in flavour compositions and / or beverages. The final form of the at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin may be chosen according to methods well known in the art and will depend on the particular beverage application. The at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin may be directly added to beverages, or may be provided as part of a flavour composition for bittering beverages. The flavour composition may, for example, comprise from about 0.01% to 90%, or about 0.1% to about 70%, or about 1% to about 50%, or about 2% to about 30% of at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, or any range or amount between these ranges, based on the total weight of the flavor composition.

[0068] The term “beer” is used in this application in its broadest sense of encompassing all styles of beer, namely a beverage brewed, most usually, from cereal grains such as barley, wheat, maize or com, although other ingredients are used in other traditional beers around the world. The present invention is concerned with adding at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin in the concentrations disclosed herein to any beverage to which it is desired to impart hop-like bitterness. The at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin may be included in any type of beverage, such as beer, non-alcoholic beer, beer-type beverages, carbonated soft drinks, and the like.

[0069] The beverage may, for example, comprise from about 0.01 ppm to about 50 ppm, or from about 0.1 ppm to about 40 ppm, or from about 1 ppm to about 30 ppm, or any range or amount between these ranges, of the at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin, including derivatives thereof.

[0070] According to certain illustrative embodiments, disclosed is a process for the manufacture of beverages having a hop-like bitterness or for the hop-like bittering of beverages, which process comprises adding to a beverage base at least one of: andrographolide, foliamenthin, menthiafolin, dihydrofoliamenthin at a concentration of from about 0.1 ppm to about 50 ppm.

[0071] In some embodiments, the process further comprises adding hop-derived ingredients, such as a hop extract or one or more components thereof, to the beverage base. In other embodiments, the process excludes adding hop-derived ingredients to the beverage base. In some embodiments, the process excludes adding hop-derived bittering ingredients to the beverage base.

[0072] In some cases, a composition, such as flavour composition, or a beverage containing at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin is substantially free of hop-derived ingredients, such as hop-derived bittering substances, such as alpha-acids and iso-alpha acids. In this context, the phrase “substantially free” refers to a composition having less than 5% alpha acids, or less than 4%, or less than 3%, or less than 2%, or less than 1%, based on the total weight of the composition.

[0073] In some cases, a composition, such as flavour composition, or a beverage containing at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin is substantially free of caffeine, quinine (Chinchona bark), quassin (Quassia bark), amarogentin and / or gentiopicrin (gentian root). In this context, the phrase “substantially free” refers to a composition having less than 1%, or less than 0.1%, or less than 0.01% of such bittering agents, based on the total weight of the composition.

[0074] Uses

[0075] The at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin obtained by and / or obtainable by the methods described herein may, for example, be added to beverages (e.g. as part of a flavour composition) to impart a hop-like bitterness to the beverage.

[0076] Also disclosed is a method of imparting hop-like bitterness to a beverage, the method comprising adding at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm. In certain embodiments, the method comprises imparting hop-like bitterness to a beverage with no or a reduced amount of hop-derived ingredients, in particular, hop-derived bittering substances. According to certain illustrative embodiments, the amount of hop-derived ingredients is reduced by at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, or at least 90% without the concomitant reduction in hop-like bitterness.

[0077] Also disclosed is a method for replacing or reducing the amount of hop-derived ingredients, in particular, hop-derived bittering ingredients, in a beverage without the concomitant reduction in bitterness impact, the method comprising adding at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin to a beverage base at a concentration of from about 0.1 ppm to about 50 ppm. According to certain illustrative embodiments, the amount of hop-derived ingredients is reduced by at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, or at least 90% without the concomitant reduction in bitterness. EXAMPLES

[0078] The following examples are given solely for the purpose of illustration and are not to be construed as limitations of the present disclosure, as many variations of the invention are possible without departing from the spirit and scope of the present disclosure. Example 1 - Taste Evaluation of Bitter Botanicals

[0079] The bitterness profile of purified botanical extracts shown in Table 1 were evaluated by expert panelists. As demonstrated by the results in Table 1, not only did Samples 2-16 fail to exhibit hop-like bitterness, but they also imparted undesirable off-tastes or off-notes. It is also evident from the results in Table 1, that Samples 17-18 (Andrographis extract which contains andrographolide; and Bogbean extract which contains foliamenthin, menthiafolin, and / or dihydrofoliamenthin) exhibited bitterness with an organoleptic profile very similar to hop extract (Reference Sample 1) without any undesirable off-tastes.

[0080] Example 2 - Flavor Composition having Hop Aroma and Andrographis extract

[0081] A flavor composition was prepared by mixing about 49 wt.% ethanol (192 proof) with a low amount of a hop aroma component (about 0.05 wt.%) comprising at least one of geranium oil, methyl nonyl ketone, neryl / geranyl acetate, geranyl butyrate, linalool, octanol, and thereafter adding about 49 wt.% propylene glycol and 0.3 wt.% Andrographis paniculata extract containing andrographolide. The flavor composition was added to a beer base free of hop-derived ingredients in an amount of about 0.10 wt.% based on the total weight of the beer. The bitterness profile of the beer was evaluated by expert panelists. It was found that the beer exhibited bitterness with an organoleptic profile similar to hop extract with a full, balanced aromatic bitterness profile, and did not impart any undesirable off-tastes or off-notes. This example demonstrates that andrographolide can be used to deliver a hop-like bitterness and can be combined with hop-derived ingredients to deliver hop aroma to a beer.

[0082] Example 3 - Flavor Composition having Hop Aroma and Andrographis extract

[0083] A flavor composition was prepared by mixing about 49 wt.% ethanol (192 proof) with a low amount of a hop aroma component (about 0.05 wt.%) comprising at least one of geranium oil, methyl nonyl ketone, neryl / geranyl acetate, geranyl butyrate, linalool, octanol, and thereafter adding about 49 wt.% propylene glycol and 0.4 wt.% Andrographis paniculata extract containing andrographolide. The flavor composition was added to a beer base free of hop-derived ingredients in an amount of about 0.10 wt.% based on the total weight of the beer. The bitterness profile of the beer was evaluated by expert panelists. It was found that the beer exhibited a hop-like bitterness with an organoleptic profile that mimics the organoleptic profile of the hop extract with a full, balanced aromatic bitterness profile, and did not impart any undesirable off-tastes or off-notes. This example demonstrates that andrographolide can be used to deliver a hop-like bitterness, and can be combined with hop-derived ingredients to deliver hop aroma to a beer.

[0084] Example 4 - Flavor Composition having Bitters, Hops oik and Andrographis extract

[0085] A flavor composition was prepared by mixing about 45 wt.% propylene glycol, about 9 wt.% quassin, about 1 wt.% naringin, and a low amount of hops oil (about 0.01 wt.%), and thereafter adding about 45 wt.% ethanol (192 proof) and about 0.2 wt.% Andrographis paniculata extract containing andrographolide. The flavor composition was added to a beer base free of hop- derived ingredients in an amount of about 0.10 wt.% based on the total weight of the beer. The bitterness profile of the beer was evaluated by expert panelists. It was found that the andrographolide enhanced the bitterness profile of the conventional bitters (quassin and naringin) and hops oil to provide a more balanced hop-like bitterness.

[0086] Example 5 - Flavor Composition having Bitters, Hops oik and Andrographis extract

[0087] A flavor composition was prepared by mixing about 45 wt.% propylene glycol, about 9 wt.% quassin, about 1 wt.% naringin, and a low amount of hops oil (about 0.01 wt.%), and thereafter adding about 45 wt.% ethanol (192 proof) and about 0.15 wt.% Andrographis paniculata extract containing andrographolide. The flavor composition was added to a beer base free of hop- derived ingredients in an amount of about 0.10 wt.% based on the total weight of the beer. The bitterness profile of the beer was evaluated by expert panelists. It was found that the andrographolide enhanced the bitterness profile of the conventional bitters (quassin and naringin) to provide a more balanced hop-like bitterness.

[0088] Example 6 - Flavor Composition having Bitters, Hops oil, and Andrographis extract

[0089] A flavor composition was prepared by mixing about 45 wt.% propylene glycol, about 45 wt.% ethanol (192 proof), about 10 wt.% quassin, a low amount of hops oil (about 0.01 wt.%), and about 0.2 wt.% Andrographis paniculata extract containing andrographolide. The flavor composition was added to a beer base free of hop-derived ingredients in an amount of about 0.10 wt.% based on the total weight of the beer. The bitterness profile of the beer was evaluated by expert panelists. It was found that the andrographolide boosted the bitterness profile of the quassin and hops oil to provide a balanced hop-like bitterness.

[0090] Example 7 - Flavor Composition having Bitters, Hops oil, and Andrographis extract

[0091] A flavor composition was prepared by mixing about 45 wt.% propylene glycol, about 45 wt.% ethanol (192 proof), about 10 wt.% quassin, a low amount of hops oil (about 0.01 wt.%), and about 0.15 wt.% Andrographis paniculata extract containing andrographolide. The flavor composition was added to a beer base free of hop-derived ingredients in an amount of about 0.10 wt.% based on the total weight of the beer. The bitterness profile of the beer was evaluated by expert panelists. It was found that the andrographolide boosted the bitterness profile of the quassin and hops oil to provide a balanced hop-like bitterness.

[0092] The foregoing broadly describes certain embodiments of the present invention without limitation. Variations and modifications as will be readily apparent to those skilled in the art are intended to be within the scope of the present invention as defined in and by the appended claims.

[0093] As utilized in accordance with the methods, compounds, and compositions of the present disclosure, the following terms, unless otherwise indicated, shall be understood to have the following meanings:

[0094] The use of the word “a” or “an” when used in conjunction with the term “comprising” in the claims and / or the specification may mean “one” but it is also consistent with the meaning of “one or more”. The use of the term “or” in the claims is used to mean “and / or” unless explicitly indicated to refer to alternatives only or when the alternatives are mutually exclusive. The term “and / or” is understood to mean that all members of a group connected by the term “and / or” are represented both cumulatively with respect to each other in any combination, and alternatively with respect to each other.

[0095] As used in this specification and claims, the words “comprising” (and any form of comprising, such as “comprise” and “comprises”), “having” (and any form of having, such as “have” and “has”), “including” (and any form of including, such as “includes” and “include”), or “containing” (and any form of containing, such as “contains” and “contain”) are inclusive or open- ended and do not exclude additional, unrecited elements or method steps.

[0096] The terms “about” or “approximately,” where used herein when referring to a measurable value such as an amount is meant to encompass, for example, variations of ± 10%, or ± 5%, or ± 1%, or ± 0.1% (including all the values within this range) from the specified value.

[0097] As used herein any reference to "one embodiment" or "an embodiment" means that a particular element, feature, structure, or characteristic described in connection with the embodiment is included in at least one embodiment and may be included in other embodiments. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment and are not necessarily limited to a single or particular embodiment. Further, all references to one or more embodiments or examples are to be construed as non-limiting to the claims.

Claims

What is claimed is:

1. A process for the manufacture of beverages having a hop-like bitterness, wherein the process comprises adding to a beverage base at least one of: andrographolide, foliamenthin, menthiafolin, dihydrofoliamenthin at a concentration of from about 0.1 ppm to about 50 ppm.

2. The process of claim 1 further comprising fermenting the beverage.

3. The process of claim 1 further comprising adding hop-derived ingredients to the beverage base.

4. The process of claim 1, wherein the process excludes adding hop-derived ingredients to the beverage base.

5. The process of claim 1, wherein the process comprises adding andrographolide to the beverage base.

6. The process of claim 1, wherein the process comprises adding foliamenthin to the beverage base.

7. The process of claim 1, wherein the beverage comprises beer, non-alcoholic beer, beer-type beverages, or carbonated soft drinks.

8. A beverage having a hop-like bitterness when manufactured by the process of claim 1.

9. The beverage of claim 8, wherein the beverage is fermented.2210. The beverage of claim 8, wherein the beverage comprises beer, non-alcoholic beer, beertype beverages, or carbonated soft drinks.

11. The beverage of claim 8, wherein the beverage is substantially free of iso-alpha hop acids.

12. The beverage of claim 8, wherein the beverage is substantially free of quinine (Chinchona bark), quassin (Quassia bark), amarogentin and / or gentiopicrin (gentian root), naringin (Citrus species).

13. Use of at least one of andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin as a hop-like bittering agent in a beer, non-alcoholic beer, beer-type beverage, or carbonated soft drink.

14. A flavour composition comprising at least one of: andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin which is effective in mimicking the organoleptic properties of one or more hop-derived ingredients when the andrographolide, foliamenthin, menthiafolin, or dihydrofoliamenthin is present at a concentration of from about 0.1 ppm to about 50 ppm in a beverage.

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