EP3629764A1 - Compositions - Google Patents

Compositions

Info

Publication number
EP3629764A1
EP3629764A1 EP18728620.8A EP18728620A EP3629764A1 EP 3629764 A1 EP3629764 A1 EP 3629764A1 EP 18728620 A EP18728620 A EP 18728620A EP 3629764 A1 EP3629764 A1 EP 3629764A1
Authority
EP
European Patent Office
Prior art keywords
sweetness
composition
sweetener
mogroside
ppm
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP18728620.8A
Other languages
German (de)
English (en)
French (fr)
Inventor
Feng Shi
Jenifer AUGELLI
Uwe KOHRS
Wei Yuan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan SA
Original Assignee
Givaudan SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Givaudan SA filed Critical Givaudan SA
Publication of EP3629764A1 publication Critical patent/EP3629764A1/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/86—Addition of bitterness inhibitors
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J17/005—Glycosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates generally to the use of one or more low-potency sweetener(s) to improve one or more sweetness characteristics of one or more high- intensity sweetener(s).
  • the present invention thus also relates to compositions comprising a mixture of at least one high-intensity sweetener and at least one low- potency sweetener.
  • the present invention further relates to the use of a combination of at least one high-intensity sweetener and at least one low-potency sweetener as a sweetness modifier wh+en used in combination with at least one other sweetener and/or as a sweetener.
  • the present invention further relates to the use of one or more mogroside(s) as a sweetness enhancer in sweetened compositions and said sweetened compositions.
  • the present invention further relates to methods of making the sweeteners and compositions disclosed herein.
  • Sweetness in comestible products that is products intended to be taken by mouth either for permanent ingestion or temporarily for expectoration, is often a desirable characteristic.
  • sweetness has been provided by the addition of one or more sweeteners, particularly low-potency, nutritive sweeteners such as sucrose (table sugar), fructose, glucose, xylose, arabinose, rhamnose, sugar alcohols such as erythritol, xylitol, mannitol, sorbitol and inositol as well as sugar syrups such as high fructose corn syrup and starch syrup. These deliver considerable sweetness without any undesirable aftertaste.
  • nutritive sweeteners such as sucrose (table sugar), fructose, glucose, xylose, arabinose, rhamnose, sugar alcohols such as erythritol, xylitol, mannitol, sorbitol and inositol
  • sugar syrups such as high fructose corn syrup and starch
  • High-intensity sweeteners have been used for this purpose.
  • High-intensity sweeteners may be natural or artificial and have a sweetness that can be several hundred times that of sucrose and thus can theoretically replace a much larger quantity of sugar in a composition.
  • high-intensity sweeteners include sucralose, saccharin, aspartame, acesulfame potassium (AceK), neotame, advantame, sterviol glycosides, including stevioside, rebaudioside A, rebaudioside D or steviol glycoside mixture preparations with rebaudioside A and/or stevioside as predominant components.
  • these substances generally have the drawback that they may impart undesirable off-tastes to comestible products, typically bitter, metallic or liquorice tastes, or an undesirable lingering sweetness.
  • a sweetness modifying composition comprising:
  • one or more high-intensity sweetener(s) selected from the group consisting of steviol glycosides and/or mogrosides;
  • one or more low-intensity sweetener(s) selected from the group consisting of cellobiose, psicose, cyclamate and/or 1 1 -O-mogroside V;
  • the sweetness modifying composition increases the sweetness of a sweetened composition by more than the sweetness of the sweetness modifying composition alone;
  • ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) ranges from about 2:1 to about 12:1 .
  • a sweetened composition comprising:
  • At least one sweetener present in an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence;
  • a sweetness modifying composition according to any aspect or embodiment of the present invention.
  • a method of enhancing the sweetness of a sweetened composition comprising providing a base composition comprising at least one sweetener present in an amount at or above its sweetness recognition threshold and/or having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence, and adding one or more high- intensity sweetener(s) selected from the group consisting of steviol glycosides and/or mogrosides and one or more low-potency sweetener(s) selected from the group consisting of cellobiose, psicose, cyclamate and/or 1 1 -O-mogroside V, wherein the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) is from about 2:1 to about 12:1 ; and/or wherein the one or more high- intensity sweetener(s) are added in a total amount equal to or greater than about 15
  • a method of making a sweetness modifying composition comprising combining one or more high-intensity sweetener(s) and one or more low-potency sweetener(s).
  • a method of making a sweetened composition comprising combining the base composition, one or more high-intensity sweetener(s), one or more low-intensity sweetener(s) and at least one other sweetener.
  • a sweetened composition comprising at least one sweetener present in an amount having a sweetness equal to or greater than 1 .5 % (w/v) sucrose equivalence; and one or more sweetness enhancer(s) selected from mogroside IV, siamenoside and neomogroside.
  • a use of one or more of mogroside IV, siamenoside and neomogroside to enhance the sweetness of a sweetened composition comprising providing a base composition and adding at least one sweetener and one or more sweetness enhancer(s) selected from mogroside IV, siamenoside and neomogroside.
  • a method of making a sweetened composition comprising combining the base composition, one or more sweetness enhancer(s) selected from mogroside IV, siamenoside and neomogroside and at least one other sweetener.
  • a sweetened composition comprising one or more mogroside(s).
  • the one or more mogroside(s) may, for example, be present as a sweetness enhancer and thus be present in an amount having a sweetness of less than 1 .5 % (w/v) sucrose equivalence.
  • the sweetened composition will then further comprise at least one sweetener present in an amount having a sweetness equal to or greater than 1 .5 % (w/v) sucrose equivalence.
  • a use of one or more mogroside(s) to enhance the sweetness of a sweetened composition comprising providing a base composition and adding at least one sweetener and one or more mogroside(s).
  • a method of making a sweetened composition comprising combining the base composition, one or more mogroside(s) and at least one other sweetener.
  • the one or more high-intensity sweetener may include or be mogroside V and/or the one or more low-potency sweetener may include or be 1 1 -O-mogroside V.
  • the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) is from about 2:1 to about 12:1 .
  • the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) is from about 5:1 to about 12:1 . In certain embodiments of any aspect of the present invention the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) may be from about 6:1 to about 10:1 .
  • the one or more high-intensity sweetener(s) may be present in a total amount ranging from about 15 ppm to about 30 ppm and/or the one or more low-potency sweetener(s) may be present in a total amount ranging from about 2 ppm to about 10 ppm. In certain embodiments of any aspect of the present invention the one or more high-intensity sweetener(s) may be present in a total amount ranging from about 22 ppm to about 28 ppm and/or the one or more low-potency sweetener(s) may be present in a total amount ranging from about 2 ppm to about 5 ppm.
  • the one or more mogroside(s) or one or more sweetness enhancer(s) may be present in an amount ranging from about 15 ppm to about 50 ppm. In certain embodiments, the one or more mogroside(s) or one or more sweetness enhancer(s) may be present in an amount ranging from about 15 ppm to about 35 ppm.
  • the combination of the one or more high-intensity sweetener(s) and the one or more low-potency sweetener(s) alone may have a sweetness less than about 1 .5 % (w/v) sucrose equivalence.
  • the concentration of the one or more high-intensity sweetener(s) and the one or more low-intensity sweetener(s) in a sweetened composition may have a sweetness less than about 1 .5 % (w/v) sucrose equivalence.
  • the one or more mogroside(s) or one or more sweetness enhancer(s) may have a total sweetness less than about 1 .5 % (w/v) sucrose equivalence. In certain embodiments, the one or more sweetness enhancer(s) increase the sweetness of a sweetened composition by more than the total sweetness of the one or more sweetness enhancer(s) alone.
  • the combination of the one or more high-intensity sweetener(s) and the one or more low-potency sweetener(s) may increase the sweetness of a sweetened composition by more than the sweetness of the combination alone. In certain embodiments of any aspect of the present invention the combination of the one or more high-intensity sweetener(s) and the one or more low-potency sweetener(s) may increase the sweetness of a composition by equal to or greater than about 1 .25 % (w/v) sucrose equivalence.
  • the one or more low-potency sweetener(s) weaken the lingering sweet taste of a sweetened composition comprising the one or more high-intensity sweetener(s) compared to the lingering sweet taste of the sweetened composition in the complete absence of the one or more low-potency sweetener(s). In certain embodiments of any aspect of the present invention the one or more low-potency sweetener(s) weakens the bitter and/or astringent taste of a sweetened composition comprising the one or more high-intensity sweetener(s) compared to the bitter and/or astringent taste of the sweetened composition in the complete absence of the one or more low-potency sweetener(s).
  • One or more (e.g. all) of the sweeteners used may be natural or synthetic (artificial).
  • One or more of the sweeteners may, for example, be made by a biological process or by an enzymatic process or by a synthetic process.
  • Figure 1 shows a chromatogram of a Luo Han Guo extract (extract 2 of Table 1 below).
  • Figure 2 shows the chemical structures of mogrosides 1 -6;
  • Figure 3 shows the LC-MS analysis of commercial Luo Han Guo extracts;
  • FIG. 4 shows the Heteronuclear Single Quantum Coherence-Total Correlation Spectroscopy (HSQC-TOCSY) (hsqcgpmlph) of iso-mogroside VI with different mixing time (d9).
  • A 10 ms mixing time.
  • B 30 ms mixing time.
  • C 60 ms mixing time.
  • D 100 ms mixing time. Because of the overlap of H-1 of Glc II and H-6a of Glc III, HSQC-COSY correlation intensity of Glc II was not analyzed here;
  • Figure 5 shows HSQC-TOCSY (hsqcgpmlph) peak intensity quantification of iso- mogroside VI glucopyranosyls with different mixing time.
  • C-3 and C-5 signals on HSQC-TOCSY appeared overlap for 100 ms mixing time. The total integration of C-3 and C-5 was therefore used in the bar chart;
  • Figure 6 shows the strategy to elucidate mogroside sugar chain ( * Numbers of C-2 to C- 6 appeared under certain mixing time might slightly change if adjusting peak intensity of HSQC-TOCSY. By observing the increasing intensity of C-2 to C-6 in different mixing time experiments connection sequence can be still determined. ** There is no natural glycosylation on C-3 of mogroside glucopyranosyl so far.
  • Step 1 Heteronuclear multiple bond correlation spectroscopy (HMBC) was used to determine anormeric C-1 and H-1 of the sugar. Start from the sugar link to aglycone.
  • HMBC Heteronuclear multiple bond correlation spectroscopy
  • Step 3 if a C-2 downshift from -575 to -581 , C-4 downshift from -571 to -581 or C-6 downshift from -562 to -69 is observed, check HMBC for glycosylation at these positions. **
  • Figure 7 shows the chemical structure for iso-mogroside VI which has the chemical formula C 6 6H 1 12 0 3 4 and an Exact Mass of 1448.70. This chemical structure is designated Formula I; and Figure 8 shows the chemical structure for 1 1 -epi-mogrosideV which has the chemical formula C 60 H 1 0 2O29 and an Exact Mass of 1286.65. This chemical structure is designated Formula II. DETAILED DESCRIPTION
  • the present invention is based on the surprising finding that a combination of one or more high-intensity sweetener(s) (e.g. mogroside V) and one or more low-potency sweetener(s) (e.g. 1 1 -O-mogroside V) can act synergistically with at least one other sweetener (e.g. sucrose) to obtain a composition having a sweetness that is greater than the sum of the sweetness of the individual sweeteners.
  • the present invention is further based on the surprising finding that one or more low-potency sweetener(s) may offset one or more negative sweetness characteristics of one or more high-potency sweetener(s).
  • the combination of one or more high-intensity sweetener(s) e.g.
  • mogroside V and one or more low-potency sweetener(s) (e.g. 1 1 -O-mogroside V) may provide improved sweetness characteristics in a sweetened composition (i.e. a composition comprising at least one other sweetener such as sucrose in an amount above its sweetness recognition threshold and/or an amount equal to or greater than about 1 .5 % (w/v) sucrose equivalence) compared to using the one or more high-intensity sweetener(s) alone.
  • the sweetness characteristics may thus, for example, be closer to the sweetness characteristics of sucrose.
  • compositions comprising one or more high-intensity sweetener(s) and one or more low-potency sweetener(s) as disclosed herein, particularly sweetened compositions comprising at least one sweetener in an amount above its sweetness recognition threshold and/or an amount equal to or greater than about 1 .5 % (w/v) sucrose equivalence and one or more high-intensity sweetener and one or more low-potency sweetener(s).
  • the sweetened compositions may also be referred to as comestible compositions.
  • compositions in particular sweetened compositions, comprising one or more of mogroside IV, siamenoside and neomogroside.
  • compositions comprising at least one high-intensity sweetener and at least one low-potency sweetener.
  • compositions comprising one or more mogroside(s), for example one or more of mogroside IV, siamenoside and neomogroside.
  • the compositions are comestible compositions.
  • a sweetness modifying composition comprising, consisting essentially of or consisting of at least one high-intensity sweetener selected from the group consisting of steviol glycosides and/or mogrosides and at least one low-potency sweetener selected from the group consisting of cellobiose, psicose, cyclamate and/or 1 1 -O-mogroside V.
  • the sweetness modifying composition comprises, consists essentially of or consists of one high-intensity sweetener and one low-potency sweetener.
  • the sweetness modifying composition may, for example, be a concentrate which may, for example, be diluted in a sweetened (e.g.
  • sweetened composition refers to a composition comprising at least one sweetener present in an amount above its sweetness recognition threshold and/or in an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence.
  • a sweetened composition comprising one or more mogroside(s), for example one or more of mogroside IV, siamenoside and neomogroside.
  • a sweetened composition e.g. comestible composition
  • a sweetened composition comprising at least one high-intensity sweetener and at least one low-potency sweetener.
  • the combination of the high-intensity sweetener(s) and low-potency sweetener(s) may be referred to as a sweetness modifying composition.
  • the one or more mogroside(s), for example the one or more of mogroside IV, siamenoside and neomogroside may also be referred to herein as a sweetness modifying composition.
  • a sweetened composition comprising at least one sweetener present in an amount above its sweetness recognition threshold and/or in an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence and a sweetness modifying composition comprising, consisting essentially of or consisting of at least one high-intensity sweetener and at least one low-potency sweetener.
  • the sweetened composition may, for example, be a comestible composition.
  • the term "enhancing" when used in relation to a particular sweetness modifying composition refers to a synergistic sweetening effect when the sweetness modifying composition is used in combination with at least one other sweetener.
  • the sweetness modifying composition increases the sweetness of a sweetened composition by more than the sweetness of the sweetness modifying composition alone. In other words, the sweetness of a composition comprising at least one sweetener and at least one sweetness modifying composition is greater than the sum of the sweetness of all the sweeteners in the composition.
  • the sweetness modifying compositions described herein are used in sweetened (e.g. comestible) compositions in amounts that have no detectable sweetness or no taste recognised as sweet (below its sweetness recognition threshold).
  • a sweetness modifying composition with a sweetness below 1 .5 % (w/v) sucrose equivalence is accepted as being "not intrinsically sweet” by FEMA (Flavor & Extract Manufacturers Association).
  • Sweetness modifiers may also be referred to as sweetness enhancers.
  • the sweetened composition comprising the sweetness modifying composition as disclosed herein and at least one sweetener in an amount above its sweetness recognition threshold and/or in an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence may have a sweetness that is equal to or more than about 1 .0 % (w/v) sucrose equivalence greater than the sweetness of the sweetened composition in the absence of the sweetness modifying composition.
  • the sweetened composition may have a sweetness that is equal to or more than about 1 .1 % (w/v) or equal to or more than about 1 .15 % (w/v) or equal to or more than about 1 .2 % (w/v) or equal to or more than about 1 .25 % (w/v) sucrose equivalence greater than the sweetness of the sweetened composition in the absence of the sweetness modifying composition.
  • the sweetness modifying composition may increase the sweetness of a sweetened composition by equal to or more than about 1 % (w/v) or equal to or more than about 1 .1 % (w/v) or equal to or more than about 1 .15 % (w/v) or equal to or more than about 1 .2 % (w/v) or equal to or more than about 1 .25 % (w/v) sucrose equivalence.
  • the comparative composition is identical to the said composition except that it does not include the said sweetness modifying composition.
  • sucrose equivalence refers to the equivalence in sweetness of a composition containing at least one non-sucrose sweetener to a reference sucrose solution.
  • taste panellists are trained to detect sweetness of reference sucrose solutions containing between 1 % and 15 % sucrose (w/v).
  • Other non-sucrose sweeteners may then be tasted at a series of dilutions to determine the concentration of the non-sucrose sweetener that is as sweet (i.e. isosweet) to a given sucrose reference.
  • isosweet refers to compositions that have equivalent sweetness. Typically, the sweetness of a given composition is measured with reference to a solution of sucrose.
  • the combination of the one or more high-intensity sweetener(s) and the one or more low-potency sweetener(s) may, for example, have a sweetness less than about 1 .5 % (w/v) sucrose equivalence.
  • the combination of the high-intensity sweetener(s) and the low-potency sweetener(s) e.g.
  • sweetness modifying composition may have a sweetness equal to or less than about 1 .45 % (w/v) sucrose equivalence or equal to or less than about 1 .4 % (w/v) sucrose equivalence or equal to or less than about 1 .35 % (w/v) sucrose equivalence or equal to or less than about 1 .3 % (w/v) sucrose equivalence.
  • the combination of the high-intensity sweetener(s) and the low-potency sweetener(s) e.g.
  • sweetness modifying composition may have a sweetness equal to or greater than about 1 % (w/v) sucrose equivalence or equal to or greater than about 1 .1 % (w/v) sucrose equivalence or equal to or greater than about 1 .15 % (w/v) sucrose equivalence or equal to or greater than about 1 .2 % (w/v) sucrose equivalence or equal to or greater than about 1 .25 % (w/v) sucrose equivalence or equal to or greater than about 1 .3 % (w/v) sucrose equivalence.
  • the one or more mogroside(s), for example one or more sweetness enhancer(s) selected from mogroside IV, siamenoside and neomogroside may, for example, have a sweetness less than about 1 .5 % (w/v) sucrose equivalence.
  • the one or more mogroside(s), for example one or more sweetness enhancer(s) selected from mogroside IV, siamenoside and neomogroside may have a sweetness equal to or less than about 1 .45 % (w/v) sucrose equivalence or equal to or less than about 1 .4 % (w/v) sucrose equivalence or equal to or less than about 1 .35 % (w/v) sucrose equivalence or equal to or less than about 1 .3 % (w/v) sucrose equivalence.
  • the one or more mogroside(s), for example one or more sweetness enhancer(s) selected from mogroside IV, siamenoside and neomogroside may have a sweetness equal to or greater than about 1 % (w/v) sucrose equivalence or equal to or greater than about 1 .1 % (w/v) sucrose equivalence or equal to or greater than about 1 .15 % (w/v) sucrose equivalence or equal to or greater than about 1 .2 % (w/v) sucrose equivalence or equal to or greater than about 1 .25 % (w/v) sucrose equivalence or equal to or greater than about 1 .3 % (w/v) sucrose equivalence.
  • sweeteners and sweetness enhancers used in the compositions disclosed herein may be a natural or synthetic (artificial) sweetener.
  • non-naturally occurring (i.e. synthetic) mogrosides are disclosed in WO 2017/075257, the contents of which are incorporated herein by reference.
  • natural sweetener refers to sweeteners that are obtained from nature, including mixtures that may have been enzymatically treated (e.g. glycosylated) to form compounds not found in nature (this does not include purified compounds that have been enzymatically treated).
  • a modified extract having a mogrol glycoside distribution that is different (e.g. enhanced) from the naturally occurring mogrol glycoside distribution may be classed as natural.
  • a mixture of glucosylated steviol glycosides and/or glucosylated mogrosides may be classed as natural.
  • Each of the sweeteners used in the compositions disclosed herein may be food-derived.
  • a "food-derived" product refers to a product which is prepared under typical cooking conditions such as, for example, using temperatures similar to those used in cooking methods.
  • the high-intensity sweetener and the low-potency sweetener used in the compositions disclosed herein are both natural sweeteners.
  • all of the sweeteners used in the compositions disclosed herein are natural.
  • the sweeteners disclosed herein may be used in pure or purified form and may be chemically synthesised, produced by biotechnological processes (e.g. fermentation) or isolated from a natural source (e.g. a botanical source including, without limitation, fruits, sugar cane, sugar beet).
  • a natural source e.g. a botanical source including, without limitation, fruits, sugar cane, sugar beet.
  • the one or more mogroside(s), for example the one or more of mogroside IV, siamenoside and neomogroside may, for example, be at least 80 wt% pure.
  • the one or more mogroside(s), for example one or more of mogroside IV, siamenoside and neomogroside may be at least about 85 wt% or at least about 90 wt% or at least about 95 wt% or at least about 98 wt% or at least about 99 wt% pure.
  • the one or more mogroside(s), for example one or more of mogroside IV, siamenoside and neomogroside may be up to 100 wt% or up to 99 wt% pure.
  • the term "high-intensity sweetener" refers to compounds having a sweetness that is at least 100 times the sweetness of sucrose.
  • the high-intensity sweetener has a sweetness that is at least about 120 or at least about 140 or at least about 150 or at least about 160 or at least about 180 or at least about 200 or at least about 220 or at least about 240 or at least about 250 or at least about 260 or at least about 280 or at least about 300 or at least about 320 or at least about 340 or at least about 350 or at least about 360 or at least about 380 or at least about 400 or at least about 420 or at least about 440 or at least about 450 times the sweetness of sucrose.
  • the high-intensity sweetener may, for example, have a sweetness that is up to 1000 times the sweetness of sucrose.
  • the high-intensity sweetener has a sweetness that is at least 100 times the sweetness of sucrose, in the context of its use in a sweetness modifying composition as described herein, they will be used in a sweetened composition in an amount that does not have any detectable sweetness or be recognised as sweet (amounts providing a sweetness less than 1 .5 % (w/v) sucrose equivalence, which is accepted as being "not intrinsically sweet” by FEMA.
  • the one or more high-intensity sweetener(s) may, for example, be one or more steviol glycosides and/or one or more mogrosides.
  • the one or more high-intensity sweetener may be a mixture of steviol glycosides and mogrosides.
  • the one or more high-intensity sweeteners may be one or more steviol glycosides.
  • the one or more high-intensity sweetener(s) may be one or more mogrosides.
  • mogrosides may perform better than steviol glycosides in terms of sweetness enhancement and off-note reduction (e.g. weakening of lingering sweet after taste).
  • the high-intensity sweetener may, for example, be one or more steviol glycoside(s).
  • steviol glycosides include, for example, stevioside (CAS: 57817-89-7), rebaudioside A (CAS: 58543-16-1 ), rebaudioside B (CAS: 58543-17-2), rebaudioside C (CAS: 63550-99-2), rebaudioside D (CAS: 63279-13-0), rebaudioside E (CAS: 63279- 14-1 ), rebaudioside F (CAS: 438045-89-7), rebaudioside G (CAS: 127345-21 -5), rebaudioside H, rebaudioside I (CAS: 1220616-34-1 ), rebaudioside J, rebaudioside K, rebaudioside L, rebaudioside M (CAS: 1220616-44-3), rebaudioside N (CAS: 1220616- 46-5), rebaudioside O (CAS: 12206
  • the high-intensity sweetener may, for example, be one or more mogroside(s). In certain embodiments, the high-intensity sweetener may be one or more of the mogrosides listed herein. In certain embodiments, the high-intensity sweetener may be one or more of mogroside IV, siamenoside, neomogroside and mogroside V (including all isomers thereof). For example, the high-intensity sweetener may be a mixture of mogroside IV, siamenoside and mogroside V (including all isomers thereof). The one or more mogroside(s) may, for example, be obtained or obtainable from Luo Han Guo fruit extracts.
  • low-potency sweetener refers to compounds having a sweetness that is less than 100 times the sweetness of sucrose. In certain embodiments, the low-potency sweetener has a sweetness that is up to about 95 times or up to about 90 times or up to about 85 times the sweetness of sucrose.
  • the one or more low-potency sweetener(s) are selected from one or more of cellobiose, psicose, cyclamate and/or 1 1 -O-mogroside V (CAS: 126105-1 1 -1 ).
  • the one or more low-intensity sweetener(s) may be one or more of cellobiose, psicose and 1 1 -O-mogroside V.
  • the one or more high-intensity sweetener(s) includes or is a high-intensity mogroside. In certain embodiments, the one or more low-potency sweetener(s) includes or is a low-potency mogroside. In certain embodiments, the one or more high-intensity sweetener includes or is a high-intensity mogroside and the one or more low-potency sweetener(s) includes or is a low-potency mogroside. In certain embodiments, the one or more high-intensity sweetener includes or is mogroside V. In certain embodiments, the one or more low-potency sweetener includes or is 1 1 -O-mogroside V.
  • the one or more high-intensity sweetener includes or is mogroside V and the one or more low-potency sweetener includes or is 1 1 -O-mogroside V.
  • Mogrosides are a group of triterpene glycosides and may be obtained from the fruit Luo Han Guo (Siraitia grosvenorii), also known as arhat fruit or longevity fruit or swingle fruit. Mogrosides make up approximately 1 % of the flesh of the fresh fruit. Through extraction, an extract in the form of a powder containing up to 80% mogrosides can be obtained.
  • Mogroside extract contains grosvenorine II, grosvenorine I, 1 1 -O-mogroside II (I), 1 1 -O-mogroside II (II), 1 1 -O-mogroside II (III), mogroside II (I), mogroside II (II), mogroside II (III), 1 1 -dehydroxy-mogroside III, 1 1 -O-mogroside III, mogroside III (I), mogroside III (II), mogroside IV (I) (siamenoside), mogroside IV (II), mogroside IV (III), mogroside IV (IV), deoxymogroside V (I), deoxymogroside V (II), 1 1 -O-mogroside V (I), mogroside V isomer, mogroside V, iso-mogroside V, 7-O-mogroside V, 1 1 -O-mogroside VI, mogroside VI (I), mogroside VI (I), mogroside VI (III) (neomogros
  • Mogroside(s) include both mogroside(s) that occur in nature and mogrosides that do not occur in nature.
  • mogrosides include, for example, grosvenorine II, grosvenorine I, 1 1 -O-mogroside II (I), 1 1 -O-mogroside II (II), 1 1 -O-mogroside II (III), mogroside II (I), mogroside II (II), mogroside II (III), 1 1 -dehydroxy-mogroside III, 1 1 -O-mogroside III, mogroside III (I), mogroside III (II), mogroside llle, mogroside Mix, mogroside IV (I) (siamenoside), mogroside IV (II), mogroside IV (III), mogroside IV (IV), deoxymogroside V (I), deoxymogroside V (II), 1 1 -O-mogroside V (I), mogroside V isomer, mogroside V, iso-mogroside V
  • Mogroside V (CAS: 88901 -36-4) is a glycoside of a cucurbitane derivative and has the chemical formula C-60H102O29 and the chemical structure shown below. Mogroside V can be found in certain plant extracts such as extracts from the fruit Luo Han Guo (Siraitia grosvenorii). Pure mogroside V has been found to have a sweetness of at least 400 times the sweetness of sucrose.
  • Siamenoside (CAS: 126105-12-2) is a cucurbitane found in the fruit of Siraitia grosvenorii and has the following chemical structure.
  • Neomogroside (CAS: 189307-15-1 ) is a cucurbitane glycoside also found in the fruit of Siraitia grosvenorii and has the following chemical structure.
  • 1 1 -O-Mogroside V (CAS: 126105-1 1 -1 ) is derived from mogroside V and has the following chemical structure. It is also found in plant extracts such as extracts from the fruit Luo Han Guo (Siraitia grosvenorii). 1 1 -O-mogroside V has been found to have a sweetness that is about 84 times the sweetness of sucrose.
  • the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) is equal to or greater than about 2:1 .
  • the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) may be equal to or greater than about 2.5:1 or equal to or greater than about 3:1 or equal to or greater than about 3.5:1 or equal to or greater than about 4:1 or equal to or greater than about 4.5:1 or equal to or greater than about 5:1 or equal to or greater than about 5.5:1 or equal to or greater than about 6:1 or equal to or greater than about 6.5:1 or equal to or greater than about 7:1 or equal to or greater than about 7.5:1 or equal to or greater than about 8:1 .
  • the ratio of the high-intensity sweetener to the low-potency sweetener is equal to or less than about 12:1 .
  • the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) may be equal to or less than about 1 1 .5:1 or equal to or less than about 1 1 :1 or equal to or less than about 10.5:1 or equal to or less than about 10:1 or equal to or less than about 9.5:1 or equal to or less than about 9:1 or equal to or less than about 8.5:1 .
  • the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) may range from about 5:1 to about 1 1 :1 or from about 6:1 to about 10:1 or from about 6.5:1 to about 9.5:1 or from about 7:1 to about 9:1 or from about 7.5:1 to about 8.5:1 .
  • the ratio of the one or more high-intensity sweetener(s) to the one or more low-potency sweetener(s) is from about 2:1 to about 12:1 or from about 4:1 to about 12:1 or from about 5:1 to about 12:1 or from about 6:1 to about 10:1 or from about 7:1 to about 9:1 .
  • the ratio may be weight or volume ratio.
  • the ratio only applies to the high-intensity sweetener(s) and low-potency sweeteners in the sweetness modifying composition (high-intensity and low-potency sweeteners that are used in a sweetened composition in an amount below the sweetness recognition threshold or having less than 1 .5 % (w/v) sucrose equivalence).
  • the one or more high-intensity sweetener(s) may be present in a composition in a total amount equal to or greater than about 15 ppm.
  • the one or more high-intensity sweetener(s) may be present in a composition in a total amount equal to or greater than about 16 ppm or equal to or greater than about 17 ppm or equal to or greater than about 18 ppm or equal to or greater than about 19 ppm or equal to or greater than about 20 ppm or equal to or greater than about 21 ppm or equal to or greater than about 22 ppm or equal to or greater than about 23 ppm or equal to or greater than about 24 ppm or equal to or greater than about 25 ppm.
  • the one or more high-intensity sweetener(s) may be present in a composition in a total amount equal to or less than about 50 ppm or equal to or less than about 48 ppm or equal to or less than about 46 ppm or equal to or less than about 45 ppm or equal to or less than about 44 ppm or equal to or less than about 42 ppm or equal to or less than about 40 ppm or equal to or less than about 38 ppm or equal to or less than about 36 ppm or equal to or less than about 35 ppm or equal to or less than about 34 ppm or equal to or less than about 32 ppm or equal to or less than about 30 ppm.
  • the one or more high-intensity sweetener(s) may be present in a composition in a total amount ranging from about 15 ppm to about 50 ppm or from about 15 ppm to about 45 ppm or from about 15 ppm to about 40 ppm or from about 15 ppm to about 35 ppm or from about 15 ppm to about 30 ppm.
  • the one or more high-intensity sweetener(s) may be present in a composition in a total amount ranging from about 15 ppm to about 30 ppm or from about 20 ppm to about 30 ppm or from about 22 ppm to about 28 ppm or from about 23 ppm to about 27 ppm or from about 24 ppm to about 26 ppm.
  • the one or more high-intensity sweetener(s) may be present in a composition in a total amount of about 20 ppm or about 25 ppm.
  • the composition may, for example, be a sweetened composition comprising at least one sweetener in an amount having a sweetness above its sweetness recognition threshold and/or equal to or greater than about 1 .5 % (w/v) sucrose equivalence.
  • the one or more low-potency sweetener(s) may be present in a composition in a total amount equal to or greater than about 2 ppm.
  • the one or more low-potency sweetener(s) may be present in a composition in a total amount equal to or greater than about 3 ppm.
  • the one or more low-potency sweetener(s) may be present in a composition in a total amount equal to or less than about 12 ppm or equal to or less than about 1 1 ppm or equal to or less than about 10 ppm or equal to or less than about 9 ppm or equal to or less than about 8 ppm or equal to or less than about 7 ppm or equal to or less than about 6 ppm or equal to or less than about 5 ppm.
  • the one or more low-potency sweetener(s) may be present in a composition in a total amount ranging from about 2 ppm to about 12 ppm or from about 2 ppm to about 10 ppm or from about 2 ppm to about 5 ppm, for example in a total amount of about 3 ppm.
  • the composition may, for example, comprise at least one sweetener other than the combination of the high-intensity sweetener and the low-potency sweetener (e.g. sweetness modifying composition) as disclosed herein.
  • the concentration ranges may, for example, be particularly suitable for liquid compositions such as beverages or compositions that do not comprise any proteins or fats.
  • compositions having a base such as milk and yogurt or other compositions that do comprise proteins and fats higher concentrations of the one or more high-intensity sweetener(s) and one or more low-potency sweetener(s) may be used. For example, concentrations that are about 1 .5 times higher than the concentrations used for liquid compositions or compositions that do not comprise any proteins or fats may be used. For example, concentrations that are from about 1 .5 times to about 3 times higher than the concentrations used for liquid compositions or compositions that do not comprise any proteins or fats may be used. Therefore, for example, the one or more high-intensity sweetener(s) may be present in a composition (e.g.
  • compositions having a base such as milk and yoghurt or other compositions that comprise proteins and/or fats in a total amount ranging from about 20 ppm to about 75 ppm, for example from about 22 ppm to about 74 ppm or from about 24 ppm to about 72 ppm or from about 25 ppm to about 70 ppm or from about 26 ppm to about 68 ppm or from about 28 ppm to about 66 ppm or from about 30 ppm to about 65 ppm or from about 30 ppm to about 60 ppm or from about 30 ppm to about 55 ppm or from about 30 ppm to about 50 ppm or from about 30 ppm to about 45 ppm.
  • a base such as milk and yoghurt or other compositions that comprise proteins and/or fats
  • the one or more low-potency sweetener(s) may be present in a composition (e.g. a composition having a base such as milk and yoghurt or other compositions that comprise proteins and/or fats) in a total amount ranging from about 3 ppm to about 20 ppm or from about 4 ppm to about 18 ppm or from about 4 ppm to about 16 ppm or from about 5 ppm to about 15 ppm or from about 6 ppm to about 15 ppm.
  • a composition e.g. a composition having a base such as milk and yoghurt or other compositions that comprise proteins and/or fats
  • a sweetened composition comprises at least one sweetener in an amount having a sweetness above its sweetness recognition threshold and/or equal to or greater than about 1 .5 % (w/v) sucrose equivalence and a sweetness modifying composition consisting of 15 ppm to about 50 ppm of one or more high-intensity sweetener(s) as described herein and 2 ppm to 12 ppm of one or more low-potency sweetener(s) as described herein.
  • a comestible composition comprises at least one sweetener and a sweetness modifying composition consisting of 15 ppm to about 30 ppm of one or more high-intensity sweetener(s) as described herein and 2 ppm to 10 ppm of one or more low-potency sweetener(s) as described herein.
  • a comestible composition comprises at least one sweetener and a sweetness modifying composition consisting of 20 ppm to about 30 ppm of one or more high-intensity sweetener(s) as described herein and 2 ppm to 10 ppm of one or more low-potency sweetener(s) as described herein.
  • a comestible composition comprises at least one sweetener and a sweetness modifying composition consisting of 22 ppm to about 28 ppm of one or more high-intensity sweetener(s) as described herein and 2 ppm to 5 ppm of one or more low-potency sweetener(s) as described herein.
  • the high- intensity sweetener is mogroside V.
  • the low-potency sweetener is 1 1 -O-mogroside V.
  • the one or more mogroside(s), for example the one or more of mogroside IV, siamenoside and neomogroside may, for example, be present in a sweetened composition in a total amount equal to or greater than about 15 ppm.
  • the one or more mogroside(s), for example the one or more of mogroside IV, siameonside and neomogroside may, for example, be present in a sweetened composition in a total amount equal to or greater than about 16 ppm or equal to or greater than about 17 ppm or equal to or greater than about 18 ppm or equal to or greater than about 19 ppm or equal to or greater than about 20 ppm or equal to or greater than about 21 ppm or equal to or greater than about 22 ppm or equal to or greater than about 23 ppm or equal to or greater than about 24 ppm or equal to or greater than about 25 ppm.
  • the one or more mogroside(s), for example the one or more of mogroside IV, siamenoside and neomogroside may, for example, be present in a sweetened composition in a total amount equal to or less than about 50 ppm, for example equal to or less than about 45 ppm, for example equal to or less than about 40 ppm, for example equal to or less than about 35 ppm.
  • the one or more mogroside(s), for example the one or more of mogroside IV, siamenoside and neomogroside may be present in a sweetened composition in a total amount ranging from about 15 ppm to about 50 ppm or from about 15 ppm to about 45 ppm or from about 15 ppm to about 40 ppm or from about 15 ppm to about 35 ppm or from about 20 ppm to about 35 ppm or from about 20 ppm to about 30 ppm.
  • ppm refers to part(s) per million by weight, for example the weight of a compound, such as Mogroside V (in milligrams) per kilogram of the product containing such compound (i.e.
  • a compound e.g. orally consumable/comestible product of the present disclosure
  • a compound e.g. orally consumable/comestible product of the present disclosure
  • Mogroside V in milligrams
  • a compound such as Mogroside V (in milligrams) per litre of the product containing such compound (i.e. mg/L) or by volume, for example, the volume of a compound, such as Mogroside V (in millilitres) per litre of the product containing such compound (i.e. ml/L).
  • the sweetness modifying compositions described herein may, for example, comprise higher concentrations of the high-intensity and low-intensity sweeteners and are then diluted in a sweetened composition to obtain the concentrations recited herein.
  • a sweetened composition comprises at least one sweetener in an amount equal to or greater than its sweetness recognition threshold and/or an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence.
  • sweetness recognition threshold refers to the lowest known concentration of a compound that is perceivable as sweet by the human sense of taste.
  • a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence is accepted as being "intrinsically sweet” by FEMA.
  • the at least one sweetener may be nutritive or non-nutritive. Nutritive sweeteners add caloric value to the foods that contain them while non-nutritive sweeteners are very low in calories or contain no calories at all. Aspartame, the only approved nutritive high- intensity sweetener contains more than 2 % of the calories in an equivalent amount of sugar as opposed to non-nutritive sweeteners that contain less than 2 % of the calories in an equivalent amount of sugar.
  • the at least one sweetener may, for example, be selected from one or more of sucrose, fructose, glucose, xylose, arabinose, rhamnose, tagatose, allulose, trehalose, isomaltulose, acesulfame potassium (AceK), aspartame, steviol glycoside(s), sucralose, high-fructose corn syrup, starch syrup, saccharin, sucralose, neotame, advantame, Luo Han Guo extract, neohespiridin, dihydrochalcone, naringin dihydrochalcone, neohesperidin dihydrochalcone, rubusoside, rebaudioside A, stevioside, stevia, trilobtain and sugar alcohols such as erythritol, xylitol, mannitol, sorbitol and inositol.
  • sweeteners
  • the at least one sweetener may, for example, be selected from one or more of sucrose, high-fructose corn syrup, acesulfame potassium (AceK), aspartame, steviol glycoside(s) and/or sucralose.
  • the amount of sweetener can be reduced by addition of a sweetness modifying composition as disclosed herein. For example, a reduction of about 1 0 to about 4° Brix or more may be achieved.
  • the at least one other sweetener present in an amount equal to or greater than its sweetness recognition threshold and/or an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence may, for example, be used in a sweetened composition in an amount equal to or greater than about 0.01 % (w/v).
  • the at least one other sweetener may be used in a sweetened composition in an amount equal to or greater than about 0.1 % (w/v) or equal to or greater than about 0.5 % (w/v) or equal to or greater than about 1 % (w/v) or equal to or greater than about 2 % (w/v).
  • the at least one other sweetener may be used in a comestible composition in an amount equal to or less than about 20 % (w/v) or equal to or less than about 15 % (w/v) or equal to or less than about 10 % (w/v) or equal to or less than about 8 % (w/v) or equal to or less than about 6 % (w/v) or equal to or less than about 5 % (w/v).
  • the at least one other sweetener present in an amount equal to or greater than its sweetness recognition threshold and/or an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence may be used in the sweetened compositions disclosed herein (e.g. comestible composition) in amounts isosweet to about 2 % (w/v) to about 15 % (w/v) sucrose.
  • a sweetness modifying composition consisting of mogroside V and 1 1 -O-mogroside V in a ratio ranging from about 2:1 to about 12:1 , for example from about 6:1 to about 10:1.
  • This sweetness modifying composition may, for example, be used as sweetness enhancer or modifier in a comestible composition.
  • the comestible composition may, for example, comprise at least one other sweetener such as sucrose.
  • the mogroside V may, for example, be used in the comestible composition in an amount ranging from about 15 ppm to about 30 ppm or from about 20 ppm to about 30 ppm (e.g. about 20 ppm or about 25 ppm).
  • the 1 1 -O-mogroside V may be used in the comestible composition in an amount ranging from about 2 ppm to about 12 ppm or from about 2 ppm to about 10 ppm (e.g. about 8.5 ppm or about 3 ppm).
  • the at least one other sweetener may, for example, be present in the comestible composition in an amount isosweet to about 2 % (w/v) to about 15 % (w/v) sucrose.
  • compositions may be in any suitable form, for example solid (e.g. powder, granules, tablets) or in solution (e.g. aqueous solution) or in an emulsion or in a suspension.
  • the compositions may further comprise a diluent or bulking agent such as dietary fibre.
  • compositions as disclosed herein include, for example, the following. - Wet/liquid soups regardless of concentration or container, including frozen soups.
  • soup(s) means a food prepared from meat, poultry, fish, vegetables, grains, fruit and other ingredients, cooked in a liquid which may include visible pieces of some or all of these ingredients. It may be clear (as a broth) or thick (as a chowder), 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 between meal snack (sipped like a beverage). Soup may be used as an ingredient for preparing other meal components and may range from broths (consomme) to sauces (cream or cheese-based soups).
  • - Dehydrated and culinary foods including cooking aid products such as: powders, granules, pastes, concentrated liquid products, including concentrated bouillon, bouillon and bouillon like products in pressed cubes, tablets or powder or granulated form, which are sold separately as a finished product or as an ingredient within a product, sauces and recipe mixes (regardless of technology).
  • cooking aid products such as: powders, granules, pastes, concentrated liquid products, including concentrated bouillon, bouillon and bouillon like products in pressed cubes, tablets or powder or granulated form, which are sold separately as a finished product or as an ingredient within a product, sauces and recipe mixes (regardless of technology).
  • - Meal solutions products such as: dehydrated and freeze dried soups, including dehydrated soup mixes, dehydrated instant soups, dehydrated ready-to-cook soups, dehydrated or ambient preparations of ready-made dishes, meals and single serve entrees including pasta, potato and rice dishes.
  • - Meal embellishment products such as: condiments, marinades, salad dressings, salad toppings, dips, breading, batter mixes, shelf stable spreads, barbecue sauces, liquid recipe mixes, concentrates, sauces or sauce mixes, including recipe mixes for salad, sold as a finished product or as an ingredient within a product, whether dehydrated, liquid or frozen.
  • - Beverages including beverage mixes and concentrates, including but not limited to, alcoholic and non-alcoholic ready to drink and dry powdered beverages, carbonated and non-carbonated beverages, e.g., sodas, fruit or vegetable juices, alcoholic and non-alcoholic beverages.
  • Confectionery products e.g., cakes, cookies, pies, candies, chewing gums, gelatins, ice creams, sorbets, puddings, jams, jellies, salad dressings, and other condiments, cereal, and other breakfast foods, canned fruits and fruit sauces and the like.
  • compositions which may, for example, be in the form of a syrup, an emulsion, a suspension, a solution or other liquid form.
  • compositions including, for example, mouth freshening agents, gargling agents, mouth rinsing agents, toothpaste, tooth polish, dentifrices, mouth sprays and dental floss.
  • compositions disclosed herein may further comprise a base composition.
  • the comestible compositions disclosed herein may further comprise a comestible base composition. This refers to all the ingredients necessary for the composition except the combination of the high-intensity sweetener and low-potency sweetener (e.g. sweetness modifying composition).
  • the base composition may, for example, be a sweetened base composition comprising at least one other sweetener present in an amount equal to or greater than its sweetness recognition threshold and/or an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence.
  • the ingredients in a base composition may include, but are not limited to, anti-caking agents, anti-foaming agents, anti-oxidants, binders, colourants, diluents, disintegrants, emulsifiers, encapsulating agents or formulations, enzymes, fats, flavour-enhancers, flavouring agents, gums, lubricants, polysaccharides, preservatives, proteins, solubilisers, solvents, stabilisers, sugar-derivatives, surfactants, sweetening agents, vitamins, waxes, and the like.
  • Solvents which may be used are known to those skilled in the art and include e.g. ethanol, ethylene glycol, propylene glycol, glycerine and triacetin.
  • Encapsulants and gums include maltodextrin, gum arabic, alginates, gelatine, modified starch, and polysaccharides.
  • the proportion of the combination of the one or more high-intensity sweetener(s) and one or more low-potency sweetener(s) will depend on the nature of the composition and the degree and characteristics of the sweetness desired. The skilled person can readily ascertain the appropriate proportion in every case with only simple, non-inventive experimentation.
  • the amounts and proportions disclosed herein are exemplary only and the flavourist may seek particular effects by working outside this range, and it should be regarded as an indication only.
  • the pH of the composition disclosed herein may be any pH that does not adversely affect the taste of the sweetener blend.
  • the pH may range from about 1 .8 to about 8 or from about 2 to about 5.
  • a person skilled in the art would be able to identify a suitable concentration of each sweetener to use depending on the pH of the composition.
  • the use of the one or more low-potency sweetener(s) with the one or more high- intensity sweetener(s) may, for example, improve one or more sweetness characteristics in a sweetened composition in comparison to the use of the one or more high-intensity sweetener(s) alone.
  • the sweetened compositions disclosed herein may, for example, have one or more improved sweetness characteristics compared to the sweetened compositions in the absence of the one or more low-potency sweetener(s).
  • sweetness enhancer(s) selected from mogroside IV, siamenoside and neomogroside may, for example, improve one or more sweetness characteristics of a sweetened composition in comparison to the use of a different sweetness enhancer such as Luo Han Guo extract in place of the one or more of mogroside IV, siamenoside and neomogroside.
  • the sweetened compositions disclosed herein may, for example, have one or more sweetness characteristics that are more similar to sucrose compared to the sweetened compositions in the absence of the one or more low-potency sweetener(s) or compared to the sweetened compositions comprising a different sweetness enhancer.
  • the sweetened compositions disclosed herein may, for example, have a weakened lingering sweet taste in compared to the sweetened compositions in the absence of the one or more low-potency sweetener(s) or compared to the sweetened compositions comprising a different sweetness enhancer.
  • the sweetened compositions disclosed herein may, for example, have a weakened bitter taste and/or astringent taste and/or metallic taste and/or liquorice taste compared to the sweetened compositions in the absence of the one or more low-potency sweetener(s) or compared to the sweetened compositions comprising a different sweetness enhancer.
  • the sweetened compositions disclosed herein may, for example, have a strengthened sweetness impact compared to the sweetened compositions in the absence of the one or more low-potency sweetener(s) or compared to the sweetened compositions comprising a different sweetness enhancer.
  • the comparative sweetened composition is identical except that it does not include any of the one or more low-potency sweetener(s) or identical except that it comprises a different sweetness enhancer in place of the one or more mogroside(s), for example one or more of mogroside IV, siamenoside and neomogroside.
  • a combination of one or more high-intensity sweetener(s) and one or more low-potency sweetener(s) to enhance the sweetness of a composition comprising at least one other sweetener present an amount equal to or greater than its sweetness recognition threshold and/or an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence.
  • the combination of the one or more high-intensity sweetener(s) and one or more low-intensity sweetener(s) has a sweetness less than 1 .5 % (w/v) sucrose equivalence.
  • the one or more high-intensity sweetener(s), one or more low-potency sweetener(s) and at least one other sweetener may be in accordance with any embodiment disclosed herein.
  • mogroside(s) for example one or more of mogroside IV, siamenoside and neomogroside to enhance the sweetness of a composition comprising at least one other sweetener present an amount equal to or greater than its sweetness recognition threshold and/or an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence.
  • a method for enhancing the sweetness of a sweetened composition comprising providing a base composition comprising at least one sweetener in an amount having a sweetness above its sweetness recognition threshold and/or an amount having a sweetness equal to or greater than about 1 .5 % (w/v) sucrose equivalence, and adding at least one low-potency sweetener, at least one high-intensity sweetener; or adding one or more mogroside(s), for example one or more of mogroside IV, siamenoside and neomogroside.
  • Each component of the final composition may be added in any order to obtain the desired final composition.
  • the method may, for example, comprise mixing the components.
  • the one or more high-intensity sweetener and/or the combination of the one or more high-intensity sweetener and the one or more low-potency sweetener (e.g. the sweetness modifying composition) and/or the one or more mogroside(s), for example one or more of mogroside IV, siamenoside and neomogroside may, for example, increase the sweetness of a sweetened composition by equal to or more than about 1 .0 % (w/v) sucrose equivalence.
  • the high-intensity sweetener(s) and/or the combination of the high-intensity sweetener(s) and the low-potency sweetener(s) and/or the one or more mogroside(s), for example one or more of mogroside IV, siamenoside and neomogroside may increase the sweetness of a sweetened composition by equal to or greater than about 1 .1 % (w/v) sucrose equivalence or equal to or greater than about 1 .15 % (w/v) sucrose equivalence or equal to or greater than about 1 .2 % (w/v) sucrose equivalence or equal to or greater than about 1 .25 % (w/v) sucrose equivalence.
  • the composition may, for example, be a composition comprising at least one other sweetener.
  • one or more low-potency sweetener(s) to improve one or more sweetness characteristics of a sweetened composition comprising one or more high-intensity sweetener(s).
  • the one or more high-intensity sweetener(s) and one or more low-potency sweetener(s) are used in amounts having a sweetness of less than about 1 .5 % (w/v) sucrose equivalence.
  • a method for improving one or more sweetness characteristics of a sweetened composition comprising one or more high-intensity sweetener(s) in an amount having a sweetness less than 1 .5 % (w/v) sucrose equivalence, the method comprising providing a composition comprising one or more high-intensity sweetener(s) and adding one or more low-potency sweetener(s).
  • Each component of the final composition may be added in any order to obtain the desired final composition.
  • the method may, for example, comprise mixing the components.
  • the improvement of one or more sweetness characteristics of a sweetened composition comprising a high-intensity sweetener may, for example, provide sweetness characteristics that are more similar to the sweetness characteristics of sucrose.
  • the sweetness characteristics may refer to the flavour profile (taste profile), which refers to the intensity of the flavour and perceptual attributes of a given compound.
  • flavour profile refers to the intensity of the flavour and perceptual attributes of a given compound.
  • Exemplary flavour attributes of sweetness are sweetness intensity, bitterness, black liquorice etc.
  • the sweetness characteristics may refer to the temporal profile, which refers to the changes in perception of sweetness over time. Every sweetener exhibits a characteristic appearance time (AT) and extinction time (ET). Most high-potency sweeteners, in contrast to carbohydrate sweeteners, display prolonged ET (lingering). Generally, the detected sucrose equivalence spikes to a maximal response level, then tapers off over time. The longer the taper, the greater the detected sweetness linger of a compound.
  • the one or more low-potency sweetener(s) may be used to weaken the lingering sweet taste of the sweetened composition comprising one or more high-intensity sweetener(s).
  • the low-potency sweetener may be used to decrease the extinction time (ET) of the sweetened composition comprising one or more high-intensity sweetener(s).
  • ET extinction time
  • the lingering sweet taste may, for example, refer to the length of time that the sweetness taste remains after it is initially detected, how rapidly the intensity of the sweetness taste decreases or fades after it is initially detected and the intensity of the sweetness taste after it is initially detected.
  • the one or more low-potency sweetener(s) may, for example, decrease the length of time that the sweetness taste remains after it is initially detected and/or increase the speed at which the sweetness taste decreases after it is initially detected and/or decrease the intensity of the sweetness taste after it is initially detected.
  • the one or more low-potency sweetener(s) may be used to weaken the bitter taste and/or astringent taste and/or metallic taste and/or liquorice taste of the sweetened composition comprising the one or more high-intensity sweetener(s).
  • the term "liquorice” refers to a sweet taste of a compound.
  • the one or more low-potency sweetener(s) may be used to strengthen the sweetness impact of the sweetened composition comprising the one or more high-intensity sweetener(s).
  • the sweetness impact relates to the length of time it takes before the sweetness is initially detected and the intensity at which the sweetness is initially detected.
  • the one or more low-potency sweetener(s) may, for example, decrease the amount of time before the sweetness is initially detected and/or increase the intensity at which the sweetness is initially detected.
  • the degree of sweetness and other sweetness characteristics described herein may be evaluated by a tasting panel of trained experts, for example as described in the examples below. Manufacturing Methods
  • compositions disclosed herein may be in accordance with any embodiment disclosed herein.
  • the methods may comprise combining each component of a desired composition in the desired proportions and optionally mixing the components together.
  • the components may be combined and mixed in any suitable order.
  • the methods may, for example, comprise providing a desired base composition and adding the sweeteners thereto.
  • Each of the sweeteners disclosed herein may be made by a synthetic process or by a biological (e.g. enzymatic) process or a fermentation process or may be isolated from a natural source such as a plant or fruit.
  • the process may, for example, comprise contacting at least one mogrol precursor substrate with a mogroside pathway enzyme.
  • the enzyme may, for example, be present in a cell lysate or may be present in a host cell (e.g.
  • the enzyme may, for example, be a UGT enzyme (UDP-glucuronosyltransferase).
  • UGT enzyme UGT-glucuronosyltransferase
  • a mogroside compound may be made by the biosynthetic pathway disclosed in WO 2013/076577 or WO 2014/086842, the contents of which are incorporated herein by reference.
  • mogroside V may be made by the biosynthetic pathway disclosed in Itkin et at., "The biosynthetic pathway of the nonsugar, high-intensity sweetener mogroside V from Siraitia grosvenorii', PNAS, 7 November 2016, E7619 - E7628 and WO 2016/038617, the contents of which are incorporated herein by reference.
  • a mogroside compound may be made by modifying (e.g. redistributing glycoside content) another mogroside compound.
  • a mogroside compound may be made by redistributing glycoside content of another mogroside compound using acid or enzymes as disclosed in WO 2014/150127, the contents of which are incorporated herein by reference.
  • the process may, for example, comprise extracting one or more sweetener compounds from a natural source such as a plant or fruit. This may, for example, be followed by a purification step to yield a high-intensity sweetener, low-intensity sweetener or mixture of sweeteners (e.g. mixture of high-intensity sweeteners such as a mixture of mogrosides).
  • the extract may, for example, have a relatively high content of mogroside V and/or 1 1 -O-mogroside V (e.g. at least about 30 wt% or at least about 40 wt%). This may, for example, involve fractioning, for example by flash chromatography.
  • One or more mogroside compounds (e.g. mogroside V) may be obtained from Luo Han Guo (Siraitia grosvenorii) fruit.
  • the target product e.g. target mogroside product
  • the target can be extracted from the aqueous fermentation reaction medium using an appropriate solvent (e.g., heptane) followed by fractional distillation.
  • the chemical composition of each fraction can be measured quantitatively by GC/MS (gas chromatography mass spectrometry).
  • Fractions can be blended to generate the desired mogroside compounds (e.g. mogroside V and 1 1 -O-mogroside V) for use in flavour or other applications. Verification of acceptability of the final blended product can be carried out by direct comparison to a reference mogroside flavouring product (for example, an existing natural flavouring commercial product obtained from a commercial supplier).
  • a reference mogroside flavouring product for example, an existing natural flavouring commercial product obtained from a commercial supplier.
  • Luo Han Guo fruit extracts obtained from Blue California (Tomas, Collinso Santa Margarita, California) (extract 4), Azile LCC (Rolling Hills Est, California) (extracts 1 and 2) and Chr. Olesen Group (Gentofte, Denmark) (extract 3) were analysed to identify the compounds present in the extract.
  • Sample solutions of the extracts were prepared by dissolving 16.52 ⁇ g of the sample in 25.0 ml_ solvent (acetonitrile/water 20/80 v/v). From this solution 100 ⁇ _ were transferred into a HPLC vial and 900 ⁇ _ solvent was added (66.1 ppm solution). From the sample solution 10 ⁇ _ was transferred to a HPLC vial and 990 ⁇ - solvent was added (6.61 ppm solution). Both the 66.1 and 6.61 ppm solutions were injected twice on the LC-MS.
  • Eluted compounds were detected using liquid chromatography mass spectrometry (LC/MS).
  • the mass spectrometer was operating in ESI negative mode measuring 150 to 2000 Amu with a resolution of 70000.
  • Gas flow rates were sheath 60, aux 20 and sweep 3.
  • Capillary temperature and aux gas heater temperature were set on 380°C and 400°C respectively.
  • V sample solvent volume in litres
  • Figure 1 shows a chromatogram of a Luo Han Guo extract (extract 2 of Table 1 below).
  • Table 1 shows the composition of four different Luo Han Guo extracts.
  • Mogroside V is the mogroside having the highest concentration in all four extracts (about 45 wt% in extract 1 ).
  • Fraction 1 -10 and 19-22 have an off-taste, which is the character of Luo Han Guo fruit, no sweet enhancement impact.
  • the better sweetness enhancement effect was observed within fractions 12-17, which contains mainly mogrosides.
  • the lingering, dirty fermented note is more noticeable, such as fractions 14 and 15.
  • pure mogroside V has inherent lingering off-taste.
  • Fraction 12 was the cleanest sweet, but less upfront due to small percentage mogroside V.
  • Fraction 13 has better sweet quality, but slightly higher astringency.
  • 1 1 - O-mogroside V and mogroside V are the two major mogrosides in those two fractions, but with different ratio (F12 mogroside V:1 1 -O-mogroside V is 4:9 and F13 mogroside V:1 1 -O-mogroside V is 13:3).
  • Mogroside V was very sweet, judged to be 425 times sweeter than sucrose, while 1 1 - O-mogroside V is rated as 84 times sweeter than sucrose.
  • a Luo Han Guo fruit extract obtained from Azile LCC (Rolling Hills Est, California) (extract 1 of Example 1 above) containing about 68 wt% mogrosides was fractionated and the composition of each fraction determined by the chromatography method described above in relation to Example 1 .
  • Table 3 shows the chemical composition of fractions 1 1 to 20 of the extract.
  • Table 4 shows the tasting results for fractions 12 to 15. The results are similar to the results obtained in Example 2.
  • numbing/irritating effects are stronger than "wet dog” fermented effects, typical in Luo Han Guo extract
  • Luo Fractions 14 and 15 have a sharp, Han Guo extract numbing, burn, which negatively effects potency and quality of sweet
  • Mogroside V and 1 1 -O-mogroside V were isolated from extracts of Luo Han Guo using Agilent 1 100 preparative HPLC system with a Phenomenex Luna C18 (2) column (5 ⁇ , 210 X 21 .4 mm), and combined to form solutions of various concentrations.
  • a sweet sensitive taste panel ranked the sweetness of solutions of a mixture of sweeteners ("Mixture 1 ”) in relation to sucrose solutions at a range of concentrations to determine sucrose equivalence.
  • Mixture 1 was a combination of fractions 1 1 to 18 of Example 2 and contained 8.16 wt% 1 1 -O-mogroside V and 61 .6 wt% mogroside V. The results are shown in Table 6 below.
  • mixture 1 has a sweetness below 1 % sucrose equivalence (as determined by seven panellists), which is accepted as "not intrinsically sweet” by FEMA. Therefore, mixture 1 is suitable for use as sweetness modifiers or blends at the indicated concentrations because it does not have any detectable sweetness at these levels.
  • a concentration of mixture 1 having an iso-sweet threshold close to 1 % (35 ppm) was selected and added to 5 % (w/v) sucrose solutions. This solution was then ranked against 5, 6, 6.5 and 7 % (w/v) sucrose solutions. This was repeated for 45 ppm Luo Han Guo extract. The average score of each solution was determined. The results are shown in Table 7 below.
  • mixture 1 and Luo Han Guo extract act as sweetness enhancers since the increase in sweetness of the 5 % (w/v) sucrose solution to which they were added was greater than the sweetness of the sweetener alone.
  • the taste of various concentrations of mixture 1 was tested by an expert panel of three people (trained flavourists) in solutions containing 5 % sucrose and 0.03 % citric acid.
  • the taste was compared to the Luo Han Guo extract used in Example 2 (obtained from Azile LCC (Rolling Hills Est, California) (extract 1 of Example 1 above) and containing about 68 wt% mogrosides) (combined with the same 5 % sucrose and 0.03 % citric acid solution). The results are shown in Table 8.
  • mixture 1 provides a better sweet quality (less baggage, sweeter) than the Luo Han Guo extract.
  • Example 6
  • a sweet sensitive taste panel ranked the sweetness of solutions of various sweeteners (mogroside V, mogroside IV, siamenoside, neomogroside, 1 1 -O-mogroside V) in relation to sucrose solutions at a range of concentrations to determine sucrose equivalence.
  • the sweeteners were obtained using an Agilent 1 100 preparative HPLC system with a Phenomenex Luna C18 (2) column (5 ⁇ , 210 X 21 .4 mm). The results are shown in Tables 9 to 13. Table 9.
  • Concentrations of the tested sweeteners were selected with an iso-sweet threshold close to 1 % and added to 5 % (w/v) sucrose solutions. These solutions were then ranked against 5, 6, 6.5 and 7 % (w/v) sucrose solutions. The average score of each solution was determined. The results are shown in Table14 below.
  • mogroside V acts as sweetness enhancers since the increase in sweetness of the 5 % (w/v) sucrose solution to which they were added was greater than the sweetness of the sweetener alone.
  • Siamenoside was described as having "more sweet body, sweeter, rounder with a little more upfront and more round lasting sweet”.
  • Mogroside IV was described as having "good and similar sweetness as mogroside V.
  • Neomogroside was described as having "sweetness, but slightly bitter aftertaste”. The results for mogroside V are shown in Table 15.
  • the mogroside V, siamenoside, mogroside IV and neomogroside were each added to a solution containing 5 % sucrose and 0.03 % citric acid in a concentration of 25 ppm (mogroside V), 25 ppm (siamenoside), 30 ppm (mogroside IV) and 30 ppm (neomogroside) respectively.
  • test solutions were tasted by an expert panel of seven people. For various aspects of sweet taste (upfront sweet, overall sweet, lingering sweet, astringent, volatile off-taste), each panellist scored the test solutions in comparison to the base solution (solution of 5 % sucrose and 0.03 % citric acid).
  • the average score for each test solution for each taste aspect was calculated. The results are shown in Table 16 below.
  • the taste of mogroside V with and without 1 1 -O-mogroside V in various milk or yoghurt bases is evaluated as shown in Table 18.
  • the iso-sweet threshold for mogroside V in milk and yoghurt is also evaluated.
  • a milk base (2% fat) includes 2% fat milk and 5 % sucrose.
  • a non-fat yoghurt base includes plain non-fat yoghurt and 5 % sucrose.
  • a full fat yoghurt base includes plain full fat yoghurt and 5 % sucrose.
  • a higher dose level is used for milk and yoghurt compositions due to the fat, protein and other ingredients. Luo Han Guo extract is used at 75 ppm for these applications.
  • Siraitia grosvenorii Swingle C. Jeffrey ex Lu et Z. Y. Zhang is a herbaceous perennial vine of Cucurbitaceae family endemic to southern China and northern Thailand.
  • the fruit of S. grosvenorii commonly known as 'luo han guo' has been used for traditional medicine in China for centuries as a treatment of respiratory infection, bronchitis, gastritis, constipation etc.
  • Modern pharmacological research have confirmed that S. grosvenorii extracts or its components possess variety of bioactivities, such as antibacterial, anti-inflammation, anti-diabetic, anti-cancer, and immunostimulatory [1 ].
  • Luo Han Guo has been used as a sweetener in food and beverages in China.
  • Optical rotations were measure with a Rudolph Autopol IV polarimeter.
  • the NMR spectra were recorded on Bruker DRX Avance 300 or 500 spectrometers. Chemical shifts are given in ⁇ (ppm) referring to the residual solvent peak.
  • Low pressure chromatography was performed on Biotage Flash System SP1 .
  • Preparative HPLC was performed on an Agilent 1 100 preparative HPLC system with a Phenomenex Lunar C18(2) column (5 ⁇ , 210 x 21 .4 mm) or a TSKgel Amide-80 (5 ⁇ , 300 x 21 .5 mm) (Tosoh Bioscience LLC).
  • Analytical HPLC was performed on an Agilent 1 100 analytical HPLC system equipped with ESA Corona CAD detector.
  • LC-MS was performed using Waters Q-Tof micro mass spectrometer coupled with Waters 2795 separation module.
  • the Luo Han Guo extract (commercial name Swingle, -60% mogrosides) was purchased from Blue California Co., Ltd.
  • Sample was eluted from the LC column using the following linear gradient (curve number 6): 0-40min: 90% A-30% A; 40-45 min: 30-10% A; 45-50 min: 10% A; 50-51 min 10%-90% A, 51 -55 min 90% A for re-equilibration.
  • the U-HPLC system was coupled to a hybrid quadrupole orthogonal time-of-flight (TOF) mass spectrometer (SYNAPT G2 HDMS, Waters MS Technologies, Manchester, UK).
  • the mass spectrometer was operated in the positive electrospray ionization mode (EST).
  • the sample cone voltage 40, capillary voltage 0.7 kv, source temperature 40 5 C, desolvation temperature 450 5 C, desolvation gas flow 800 L/h, and cone gas flow 50 L/h were optimized.
  • Leucine enkephalin was used as the lock mass [M+H] " at m/ z 556.2771 .
  • Sodium formate solution was used for external instrument calibration.
  • Fractions 36-38 with iso-mogroside VI and 1 1 -epi-mogroside V were combined to evaporate solvents. Further preparative HPLC purification of fractions 36- 38 afforded iso-mogroside VI (1 , 22 mg) and 1 1 -epi-mogroside V (2, 17 mg) (24% acetonitrile in water, 10 mL/min, retention time 13.1 min and 14.3 min, respectively).
  • 1 1 -oxo-mogroside V (4) and neomogroside (3) were mainly in flash fractions 39-40 with 1 1 -oxo-mogroside V as the major component.
  • neomogroside appeared as a tail shoulder of 1 1 -oxo-mogroside (24% acetonitrile in water, 10 mL/min, retention time 17.0 min and 18.0 min, respectively). Collection of the peak front gave 105 mg of the compound 1 1 -oxo-mogroside V (4). Further purification of the shoulder neomogroside (3, 15 mg) was achieved by preparative HPLC on TSKgel Amide-80 (65% acetonitrile in water, 20 mL/min, rt 15.5 min).
  • the n-hexane extract was analyzed by GC-MS under the following conditions: capillary column HP-5MS (30 m ⁇ 0.25 mm ⁇ 0.25 ⁇ , Agilent); column temperature, 180 to 230 ⁇ at a ramp of 5 ⁇ C/min ; injection tern perature, 250 ⁇ ; carrier, He gas; split ratio, 20:1 .
  • the O-silylated derivatives of D-glucose and L-glucose showed retention time at 16.02 and 16.39 min, respectively. By comparing the retention time and co-chromatography, the sugar residues after acid hydrolysis of 1 and 2 were determined to be D-glucose.
  • the NMR spectral data of 1 suggested the structure of a hexasaccharide triterpenoid saponin: 30 of the 66 carbons were assigned to the triterpenoid aglycone, and 36 of 66 to six hexose moieties.
  • the 13 C and 1 H NMR spectra of 1 showed the signals of seven singlet tertiary methyls, a doublet secondary methyl, and an olefinic methine (Table 19), which suggested a typical (24R)-cucurbit-5-ene-33,1 1 a,24,25-tetraol mogrol aglycone.
  • the mogrol aglycone of 1 was further confirmed by extensive analysis of its 1 H, 13 C, and 2D (COSY, TOCSY, HSQC and NOESY) NMR data, as well as comparison with NMR data of mogroside V standard.
  • the 13 C signals of Glc-I (5 C 75.1 , 77.8, 71 .4, 77.2, 70.1 ) as determined by HSQC-TOCSY missed a typical C-6 carbon signal at around 5 C 62.
  • the downfield shift of Glc-I C-6 (5 C 70.1 ) indicated glycosylation at this position.
  • the 13 C pattern of Glc-lll (5c 81 .6, 78.3, 71 .4, 76.4, 70.0) suggested C-2 and C-6 glycosylation shifts.
  • Analysis of HSQC-TOCSY with 10, 30, 60, and 100 ms mixing time resulted in the sequential assignment and confirmation of C-2 and C-6 downfield shifts.
  • Glc-IV was a regular terminal glucopyranosyl without any substitution (5 C 74.5, 77.7, 71 .2, 78.2, 62.4).
  • Glc-VI was a terminal glucopyranosyl without further sugar branch.
  • iso-mogroside (1 ) was assigned as 3- ⁇ - ⁇ - D-glucopyranosyl(1 ⁇ 6)-3-D-glucopyranosyl-mogrol-24-0-3-D-glucopyranosyl-(1 ⁇ 6- [3-D-glucopyranosyl-(1 ⁇ 4)-B-D-glucopyranosyl-(1 ⁇ 2)]-B-D-glucopyranosyl.
  • Compound 2 was assigned a molecular formula of C6oH 102 029 from its HR-ESI-MS data ([M-H] " m/z, 1285.6429).
  • the NMR data of the oligosaccharide portion of 2 were superimposable with those of mogroside V.
  • Detailed 2-D NMR experiments including HSQC, HMBC, NOESY, COSY and HSQC-TOCSY confirmed that 2 had the same sugar moieties as mogroside V. Attentions were then turned onto the aglycone NMR data.
  • the HMBC correlation between C-1 1 and H 3 -19 revealed significant upfield shift of C-1 1 (5 C 72.5) as compared with mogroside V (5 C 77.8).
  • the 13 C NMR data of compound 2 aglycone had a good match with the data of the semi-synthetic 1 1 - ⁇ - ⁇ cucurbitane glycoside, which was recorded in pyridine-d 6 [14].
  • the 13 C NMR data of natural 1 1 - ⁇ - ⁇ cucurbitane by Matsuda et al was obtained in methanol-c/4 and were quite different in terms of chemical shifts at C-1 1 , C-8, C-10 and C-12 [15].
  • semi-synthesis of 2 was carried out by chemical reduction of 1 1 -oxo-mogroside V (4) to the 1 1 - ⁇ - ⁇ and 1 1 -a-OH isomers of mogroside V.
  • the semisynthetic 1 1 -epi-mogroside V was determined to be identical to the isolated 1 1 -epi- mogroside V. Therefore, the structure of 1 1 -epi-mogroside V (2) was elucidated as 3- ⁇ - ⁇ -D-glucopyranosy I ⁇ 6) ⁇ -D-glucopyranosyl-1 1 ⁇ - ⁇ - ⁇ -24-0- ⁇ - ⁇ - glucopyranosyl-(1 ⁇ 2)-[B-D-glucopyranosyl-(1 ⁇ 6)]-3-D-glucopyranosyl. To our best of knowledge, this is the first report of natural mogroside with a 1 1 - ⁇ hydroxyl group.
  • the chemical shifts of the carbon signals as determined by HSQC/HMQC are very important information to confirm the monosaccharide type since the pattern of C-1 to C-6 chemical shifts for different type of monosaccharides is characteristic and consistent.
  • the glycosylation position on the sugar chain can be identified and further confirmed by HMBC correlation.
  • traditional way to elucidate saponin sugar is: HMBC ⁇ C-1 , H-1 ⁇ COSY ⁇ H-2 to H-6 ⁇ HSQC/HMQC ⁇ C-2 to C-6, then assisted and confirmed by coupling constant analysis and NOESY experiment.
  • TOCSY experiment not only can be used to group proton signals into spin systems, but also provide the stereochemistry information of the saccharide. For example, we should be able to see the magnetization relay of glucose through H-1 to H-6 with the right mixing time. For galactose, there is no magnetization relay over H-4 even with 200 ms mixing time.
  • HSQC-TOCSY have been applied in the structure elucidation and assignment of saponins by grouping carbon signals in each spin system together [17, 18].
  • Figure 6 summarized the new HSQC-TOCSY based strategy to elucidate the glucopyranosyl oligosaccharide chain of mogrosides as follows:
  • HMBC Heteronuclear multiple bond correlation spectroscopy
  • Step 2 HSQC-TOCSY was used with 100ms mixing time to determine the whole group of C-2 to C-6.
  • Step 3 if a C-2 downshift from -575 to -581 , C-4 downshift from -571 to -581 or C-6 downshift from -562 to -69 is observed, check HMBC for glycosylation at these positions.
  • HMBC glycosylation at these positions.
  • 1 -D NMR data such as 1 H coupling constants and 13 C carbon signal pattern
  • 2-D NMR experiments such as NOESY, HMBC, TOCSY, COSY and HSQC could assist the process and confirm the results.
  • the new HSQC- TOCSY based strategy may provide a simple, fast and unambiguous way for elucidation and assignment of glucopyranosyl chains of any new or known mogrosides. The strategy can also be adapted for elucidation and assignment of other monosaccharides and oligosaccharides.
  • Compound 3 was determined to be neomogroside by extensive 1 -D and 2-D NMR analysis, as well as comparison with literature data [19].
  • signals were assigned by HSQC-TOCSY and TOCSY experiments with different mixing time at 10, 30, 60, 100 ms.
  • the linkage of the six saccharides were made by their NOESY and HMBC correlations.
  • the oligosaccharide chain on C-3 of aglycone can be clearly assigned as 3-D-glucopyranosyl-(1 ⁇ 2)-B-D-glucopyranosyl- (1 ⁇ 6)-3-D-glucopyranosyl.
  • the glucopyranosyl on C-24 of aglycone was branched with a 3-D-glucopyranosyl-(1 ⁇ 2) and a 3-D-glucopyranosyl-(1 ⁇ 6).
  • Neomogroside was firstly discovered from S. grosvenorii and described by Si et al.
  • neomogroside and mogroside VI had the same CAS number 189307-15-1 and same structure.
  • mogroside VI Takemoto et al firstly reported mogroside VI from S. grosvenorii [2]. But it only referred a pure mogroside with a molecular formula of C 6 6H 1 12 0 34 and no structure was determined [2].
  • Prakash et al. reported the structure and NMR data of mogroside VI as a known compound in their article published in 201 1 [6]. In their article, the structure of mogroside VI was assigned as the structure of 6 in Figure 2. Prakash mentioned that the structure elucidation of mogroside VI was made by NMR analysis and also by comparing with the literature values. However, no citation was given for the literature values.
  • Example 12 Four sweet sensitive panelists evaluated 100 ppm iso-mogroside VI and 374 ppm 1 1 - epi-mogroside V and the sucrose standards, and were asked to give sweet equivalence concentrations to sucrose. The mean sweet equivalence concentrations of each compound were used to calculate the iso-sweet potency. The iso-sweet potency values of iso-mogroside VI and 1 1 -epi-mogroside V were determined as 91 and 35 times of sweetness of sucrose, respectively (100 ppm iso-mogroside VI sweet equivalent to 0.91 % sucrose; 374 ppm 1 1 -epi-mogroside V sweet equivalent to 1 .31 % sucrose). Example 12
  • Iso-Mogroside VI and 1 1 -epi-mogroside V were obtained as described in Example 10.
  • the iso-Mogroside VI and 1 1 -epi-mogroside V were each added to a solution containing 5 % sucrose and 0.03 % citric acid in a concentration of 25 ppm.
  • These test solutions were tasted by an expert panel of seven people.
  • sweet taste overall sweet, upfront sweet, lingering sweet, astringent, volatile off-note
  • each panellist scored the test solutions in comparison to the base solution (solution of 5 % sucrose and 0.03 % citric acid). A score of 0 indicated that the taste aspect was the same, 1 indicates slightly higher, 2 indicates higher, 3 indicates much higher, -1 indicates slightly lower, -2 indicates lower and -3 indicates much lower.
  • the sweet potency of iso-mogroside VI and 1 1 -epi-mogroside V were evaluated as 91 and 35 times of sweetness of sucrose, respectively (100 ppm iso-mogroside VI sweet equivalent to 0.91 % sucrose; 374 ppm 1 1 -epi-mogroside V sweet equivalent to 1 .31 % sucrose).
  • the new strategy based on HSQC-TOCSY experiments with different mixing times featured a quick and unambiguous elucidation and assignment of glucopyranosyl oligosaccharide chains.
  • the previous confusion regarding the structures of neomogroside and mogroside VI was reviewed and clarified after the confirmation of neomogroside structure by our extensive NMR spectral analysis.

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