Diterpene glycosides containing an ent-atisene core, compositions and methods

Patent metadata

Field	Value
Publication number	US-11447516-B2
Application number	US-201716338626-A
Country	US
Kind code	B2
Filing date	Oct 4, 2017
Priority date	Oct 4, 2016
Publication date	Sep 20, 2022
Grant date	Sep 20, 2022

Abstract

Novel diterpene glycosides containing ent-atisene cores are provided herein. Compositions and consumables comprising the novel diterpene glycosides are also provided herein. Methods of enhancing the sweetness and/or flavor of consumables using the novel diterpene glycosides, methods of preparing compositions and consumables comprising the novel diterpene glycosides and methods of purifying the novel diterpene glycosides are also provided.

First claim

We claim:

1. A diterpene glycoside of Formula I:

wherein when y is a double bond, X is C, Y is CH 2 , z is absent and Z is absent;
when y is single bond, z is a single bond, X is C and Y and Z are each independently selected from methyl and hydroxyl; and
R 1 and R 2 are each independently selected from a monosaccharide and an oligosaccharide.

2. The diterpene glycoside of claim 1 , wherein each saccharide of the monosaccharide and oligosaccharide is selected from the group consisting of glucose, xylose, rhamnose, fructose, 6-deoxy-glucose and combinations thereof.

3. The diterpene glycoside of claim 1 , wherein R 1 and R 2 are both oligosaccharides.

4. The diterpene glycoside of claim 1 , wherein the diterpene glycoside comprises from 4 to 10 saccharides.

5. The diterpene glycoside of claim 1 , wherein the diterpene glycoside is selected from the group consisting of:

6. The diterpene glycoside of claim 1 , wherein the diterpene glycoside is isolated and purified.

7. A composition comprising at least one diterpene glycoside of claim 1 .

8. The composition of claim 7 , wherein the composition is selected from a sweetener composition, a sweetness enhancing composition and a flavor enhancing composition.

9. The composition of claim 7 , wherein the diterpene glycoside is provided as part of a mixture, and wherein the diterpene glycoside is present in the mixture in an amount greater than about 95% by weight on a dry basis.

10. The composition of claim 7 , further comprising at least one compound selected from a sweetener, additive and functional ingredient.

11. A consumable comprising at least one diterpene glycoside of claim 1 .

12. The consumable of claim 11 , wherein the consumable is a beverage or beverage product.

13. A method for enhancing the flavor of a consumable, comprising (i) providing a consumable comprising at least one flavor ingredient and (ii) adding a diterpene glycoside of Formula I to the consumable to provide a consumable with enhanced flavor, wherein the diterpene glycoside of Formula I in present in the consumable with enhanced flavor at a concentration below its flavor recognition threshold, and wherein Formula I is:

wherein:
when y is a double bond, X is C, Y is CH 2 , z is absent and Z is absent;
when y is single bond, z is a single bond, X is C and Y and Z are each independently selected from methyl and hydroxyl; and
R 1 and R 2 are each independently selected from a monosaccharide and oligosaccharide.

14. A method for enhancing the sweetness of a consumable, comprising (i) providing a consumable comprising at least one sweet ingredient and (ii) adding a diterpene glycoside of Formula I to the consumable to provide a consumable with enhanced sweetness, wherein the diterpene glycoside of Formula I in present in the consumable with enhanced sweetness at a concentration below its flavor recognition threshold, and wherein Formula 1 is:

wherein:
when y is a double bond, X is C, Y is CH 2 , z is absent and Z is absent;
when y is single bond, z is a single bond, X is C and Y and Z are each independently selected from methyl and hydroxyl; and
R 1 and R 2 are each independently selected from a monosaccharide and oligosaccharide.

15. The method of claim 13 , wherein the consumable is a beverage or beverage product.

16. A method for purifying a diterpene glycoside of Formula I:

wherein:
when y is a double bond, X is C, Y is CH 2 , z is absent and Z is absent;
when y is single bond, z is a single bond, X is C and Y and Z are each independently selected from methyl and hydroxyl; and
R 1 and R 2 are each independently selected from a monosaccharide and oligosaccharide; comprising:
(i) passing a solution comprising a source material comprising a diterpene glycoside of Formula I through a HPLC column, and
(ii) eluting fractions comprising the diterpene glycoside of Formula I to provide a purified diterpene glycoside of Formula 1 having a purity of about 50% or greater.

17. The method of claim 16 , wherein the purified diterpene glycoside of Formula I has a purity of about 95% or greater.

18. The method of claim 16 , wherein the diterpene glycoside of Formula I is selected from the group consisting of:

Assignees

• Coca Cola Co

Inventors

• Prakash Indra
• Ma Gil

Classifications

• A23L27/88

  Taste or flavour enhancing agents · CPC title

• A23L27/36

  Terpene glycosides · CPC title

• C07H15/256 Primary

  Polyterpene radicals · CPC title

• C07H1/06

  Separation; Purification · CPC title

• A23L27/30

  Artificial sweetening agents · CPC title