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Steviol Glycosides and Their Compositions Steviol-Glycoside Und Zusammensetzungen Daraus Glycosides De Stéviol Et Leurs Compositions

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Steviol Glycosides and Their Compositions Steviol-Glycoside Und Zusammensetzungen Daraus Glycosides De Stéviol Et Leurs Compositions (19) TZZ Z¥_T (11) EP 2 970 354 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07H 15/24 (2006.01) A23L 27/30 (2016.01) 30.05.2018 Bulletin 2018/22 A23L 2/60 (2006.01) (21) Application number: 14762406.8 (86) International application number: PCT/US2014/031129 (22) Date of filing: 18.03.2014 (87) International publication number: WO 2014/146135 (18.09.2014 Gazette 2014/38) (54) STEVIOL GLYCOSIDES AND THEIR COMPOSITIONS STEVIOL-GLYCOSIDE UND ZUSAMMENSETZUNGEN DARAUS GLYCOSIDES DE STÉVIOL ET LEURS COMPOSITIONS (84) Designated Contracting States: • MARKOSYAN, Avetik AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Kuala Lumpur 59200 (MY) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR (74) Representative: Towler, Philip Dean Dehns (30) Priority: 15.03.2013 US 201361788633 P St Bride’s House 20.08.2013 US 201361867832 P 10 Salisbury Square London EC4Y 8JD (GB) (43) Date of publication of application: 20.01.2016 Bulletin 2016/03 (56) References cited: WO-A1-2011/153378 US-A1- 2010 278 993 (60) Divisional application: US-A1- 2010 278 993 US-A1- 2011 092 684 18165158.9 US-A1- 2011 183 056 (73) Proprietors: • MASAYA OHTA: "Characterization of Novel • The Coca-Cola Company Steviol Glycosides from Leaves of Stevia Atlanta, GA 30313 (US) rebaudiana Morita", J. APPL. GLYCOSCI., vol. 57, • PureCircle SDN BHD 17 August 2010 (2010-08-17), pages 199-209, 71760 Bandar Enstek, Negeri Sembilan (MY) XP055121080, • CHATURVEDULA ET AL.: ’Enzymatic and acid (72) Inventors: hydrolysis of steviol and cucurbitane • PRAKASH, Indra glycosides.’ INT J PHARM BIOMED RES vol. 2, Alpharetta, GA 30022 (US) no. 2, 2011, pages 135 - 139, XP055288643 • CHATURVEDULA, Venkata Sai Prakash • PRAKASH ET AL.: ’Structural Characterization of Tempe, AZ 85283 (US) the Degradation Products of a Minor Natural • HIGIRO, Juvenal Sweet Diterpene Glycoside Rebaudioside M Atlanta, GA 30345 (US) under Acidic Conditions.’ INT. J. MOL. SCI. vol. 15, no. 1, January 2014, pages 1014 - 1025, XP055288644 Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 970 354 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 970 354 B1 Description FIELD OF THE INVENTION 5 [0001] The present invention relates generally to steviol glycosides, as well as compositions comprising such steviol glycosides. The present invention further extends to methods of preparing and purifying such steviol glycosides, methods for preparing compositions comprising such steviol glycosides (e.g., consumables) and methods for enhancing the flavor or sweetness of consumables using steviol glycosides and compositions comprising the same. 10 BACKGROUND OF THE INVENTION [0002] Natural caloric sugars, such as sucrose, fructose and glucose, are utilized to provide a pleasant taste to bev- erages, foods, pharmaceuticals, and oral hygienic/cosmetic products. Sucrose, in particular, imparts a taste preferred by consumers. Although sucrose provides superior sweetness characteristics, it is caloric. Non-caloric or low caloric 15 sweeteners have been introduced to satisfy consumer demand. However, sweeteners within this class differ from natural caloric sugars in ways that continue to frustrate consumers. On a taste basis, non-caloric or low caloric sweeteners exhibit a temporal profile, maximal response, flavor profile, mouth feel, and/or adaptation behavior that differ from sugar. Specifically, non-caloric or low caloric sweeteners exhibit delayed sweetness onset, lingering sweet aftertaste, bitter taste, metallic taste, astringent taste, cooling taste and/or licorice-like taste. On a source basis, many non-caloric or low 20 caloric sweeteners are synthetic chemicals. The desire for a natural non-caloric or low caloric sweetener that tastes like sucrose remains high. [0003] Stevia rebaudiana Bertoni is a perennial shrub of the Asteraceae (Compositae) family native to certain regions of South America. Its leaves have been traditionally used for hundreds of years in Paraguay and Brazil to sweeten local teas and medicines. The plant is commercially cultivated in Japan, Singapore, Taiwan, Malaysia, South Korea, China, 25 Israel, India, Brazil, Australia and Paraguay. [0004] The leaves of the plant contain a mixture containing diterpene glycosides in an amount ranging from about 10%to 20% of the total dryweight. These diterpeneglycosides areabout 150 to 450 times sweeterthan sugar.Structurally, the diterpene glycosides are characterized by a single base, steviol, and differ by the presence of carbohydrate residues at positions C13 and C19. Typically, on a dry weight basis, the four major steviol glycosides found in the leaves of Stevia 30 are dulcoside A (0.3%), rebaudioside C (0.6-1.0%), rebaudioside A (3.8%) and stevioside (9.1 %). Other glycosides identified in Stevia extract include rebaudioside B, D, E, and F, steviolbioside and rubusoside. Among these, only steviosideand rebaudioside Aare availableon a commercial scale. US2010/0278993 disclosesrebaudioside A derivative products and methods for making them. The use of steviol glycosides has been limited to date by certain undesirable taste properties, including licorice taste, bitterness, astringency, sweet aftertaste, bitter aftertaste, licorice aftertaste, and 35 become more prominent with increase of concentration. These undesirable taste attributes are particularly prominent in carbonated beverages, where full replacement of sugar requires concentrations of steviol glycosides that exceed 500 mg/L. Use at that level results in significant deterioration in the final product taste. [0005] Accordingly, there remains a need to develop natural reduced or non-caloric sweeteners that provide a temporal and flavor profile similar to that of sucrose. 40 [0006] There remains a further need for methods for purifying steviol glycosides from stevia. SUMMARY OF THE INVENTION [0007] The present invention relates generally to steviol glycosides and compositions comprising such steviol glyco- 45 sides, as well as methods of preparing and purifying such steviol glycosides, methods of preparing compositions com- prising such steviol glycosides (e.g., consumables) and methods for enhancing the flavor or sweetness of consumables using these steviol glycosides and compositions. [0008] In one aspect, the present invention is a steviol glycoside of formula (1): 50 55 2 EP 2 970 354 B1 5 10 15 20 wherein the steviol glycoside of formula (1) is selected from the group consisting of (1a) (1b), (1c), and (1d) : 25 30 35 40 45 50 55 3 EP 2 970 354 B1 5 10 15 20 25 30 35 40 45 50 55 4 EP 2 970 354 B1 5 10 15 20 25 [0009] Further described herein are steviol glycosides (1e), (1f), and (1g): 30 35 40 45 50 55 5 EP 2 970 354 B1 5 10 15 20 25 30 35 40 45 50 55 [0010] In another embodiment, the present invention is a steviol glycoside of formula (2): 6 EP 2 970 354 B1 5 10 15 20 wherein the steviol glycoside of formula (2) is selected from (2a), (2b), (2c), and (2d) : 25 30 35 40 45 50 55 7 EP 2 970 354 B1 5 10 15 20 25 30 35 40 45 50 55 8 EP 2 970 354 B1 5 10 15 20 25 [0011] Further described herein are steviol glycosides (2e), (2f) and (2g): 30 35 40 45 50 55 9 EP 2 970 354 B1 5 10 15 20 25 and 30 35 40 45 50 55 [0012] Steviol glycoside (2f) is also referred to as rebaudioside N and steviol glycoside (2g) is also referred to as rebaudioside O. [0013] In a further aspect, the present invention is a composition comprising a compound of formula (1). 10 EP 2 970 354 B1 [0014] In one embodiment, the present invention is a sweetener composition comprising a compound of formula (1). [0015] In another embodiment, the present invention is a flavor-enhancing composition comprising a compound of formula (1), wherein the compound of formula (1) is present in an amount effective to provide a concentration at or below the threshold flavor recognition level of the compound of formula (1) when the flavor-enhancing composition is added 5 to a consumable In a particular embodiment, the compound of formula (1) is present in an amount effective to provide a concentration below the threshold flavor recognition level of the compound of formula (1) when the flavor-enhancing composition is added to a consumable. In one embodiment, the compound of formula (1) is present in an amount effective to provide a concentration at least about 1%, at least about 5%, at least about 10%, at least about 15,% at least about 20% or at least about 25% or more below the threshold flavor recognition level of the compound of formula (1) when 10 the flavor-enhancing composition is added to a consumable. [0016] In yet another embodiment, the present invention is a sweetness-enhancing composition comprising a com- pound of formula (1), wherein the compound of forumula (1) is present in an amount effective to provide a concentration at or below the threshold sweetness recognition level of the compound of formula (1) when the sweetness-enhancing composition is added to a consumable In a particular embodiment, the compound of forumula (1) is present in an amount 15 effective to provide a concentration below the threshold sweetness recognition level of the compound of formula (1) when the sweetness-enhancing composition is added to a consumable. In one embodiment, the compound of forumula (1) is present in an amount effective to provide a concentration at least about 1%, at least about 5%, at least about 10%, at least about 15,% at least about 20% or at least about 25% or more below the threshold sweetness recognition level of the compound of formula (1) when the sweetness-enhancing composition is added to a consumable.
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