- Enzymatic Monoglucosylation of Rubusoside and the Structure-Sweetness/Taste Relationship of Monoglucosyl Derivatives
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Monoglucosylation of rubusoside not only could increase its structural diversity but may also improve its taste. To biosynthesize the monoglucosyl rubusosides, a series of glycosyltransferases and glycosynthases were screened to identify the enzymes capable of specifically glycosylating the hydroxyl groups of the 13-O-β-d-glucosyl and 19-COO-β-d-glucosyl moieties. After structural characterization, the effect of structure on sweetness and taste was established based on these rubusoside-derived analogues, including two first characterized compounds. β-Monoglucosylation of two 2-hydroxyl groups, as well as α-monoglucosylations of the 4- and 6-hydroxyl groups of the 13-glucosyl moiety, could significantly increase the relative sweetness of rubusoside to 140 while maintaining or improving the taste quality. In contrast, monoglucosylations of other hydroxyl groups in our study usually decreased the taste quality of the rubusoside. Additionally, the possibility of a negative influence of these monoglucosylated derivatives on the function of islets was preliminarily excluded, which should facilitate the development of rubusoside-derived sweeteners.
- Chen, Yijun,Li, Zhenlin,Wang, Xiaonan,Wang, Yao,Wu, Xuri,Zhao, Ling
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- RECOMBINANT PRODUCTION OF STEVIOL GLYCOSIDES
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Recombinant microorganisms, plants, and plant cells are disclosed that have been engineered to express recombinant genes encoding UDP-glycosyltransferases (UGTs). Such microorganisms, plants, or plant cells can produce steviol glycosides, e.g., Rebaudioside A and/or Rebaudioside D, which can be used as natural sweeteners in food products and dietary supplements.
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Paragraph 0054; 0333; 0334; 0360; 0361
(2016/08/17)
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- HIGH-PURITY STEVIOL GLYCOSIDES
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Methods of preparing highly purified steviol glycosides, particularly rebaudiosides A, D and M are described. The methods include utilizing recombinant microorganisms for converting various staring compositions to target steviol glycosides. In addition, novel steviol glycosides reb D2, reb M2, and reb I are disclosed, as are methods of preparing the same. The highly purified rebaudiosides are useful as non-caloric sweetener in edible and chewable compositions such as any beverages, confectioneries, bakery products, cookies, and chewing gums.
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- PRODUCTION OF STEVIOL GLYCOSIDES IN RECOMBINANT HOSTS
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The invention relates to recombinant microorganisms and methods for producing steviol glycosides, glycosylated ent-kaurenol, and glycosylated ent-kaurenoic acid.
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Paragraph 00196
(2016/08/23)
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- HIGH-PURITY STEVIOL GLYCOSIDES
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Methods of preparing highly purified steviol glycosides, particularly rebaudiosides A, D and M are described. The methods include utilizing recombinant microorganisms for converting various staring compositions to target steviol glycosides. In addition, novel steviol glycosides reb D2 and reb M2 are disclosed, as are methods of preparing the same. The highly purified rebaudiosides are useful as non-caloric sweetener in edible and chewable compositions such as any beverages, confectioneries, bakery products, cookies, and chewing gums.
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Page/Page column 56
(2014/12/12)
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- PROCESS FOR MANUFACTURING A SWEETENER AND USE THEREOF
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Highly purified Stevioside and Rebaudioside A were prepared from sweet glycoside extracts obtained from Stevia rebaudiana Bertoni leaves. The resulting sweeteners are suitable as non-calorie, non-cariogenic, non-bitter, non-lingering sweeteners, which may be advantageously applied in foods, beverages, and milk products.
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- Solubilization of steviolbioside and steviolmonoside with γ-cyclodextrin and its application to selective syntheses of better sweet glycosides from stevioside and rubusoside
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1,4-α-Glucosylation at the 13-O-glycosyl moiety of stevioside (S) and rubusoside (RU) results in a significant increase of sweetness. Saponification of the 19-COO-β-glucosyl linkage of S and RU yielded steviolbioside (SB) (= 13-O-β-sophorosyl-steviol) and steviolmonoside (SM) (= 13-O-β-glucosyl-steviol), respectively, both of which are poorly soluble in an acetate buffer. It was found that the solubilities of SM and SB in the buffer solution were remarkably increased in the presence of γ-cyclodextrin (γ-CD). SB was solubilized in the buffer solution with the aid of γ-CD, and the solution was subjected to 1,4-α-transglucosylation by using a cyclodextrin glucanotransferase-starch system to give a mixture of products which were glucosylated at the 13-O-glycosyl moiety. This mixture was acetylated, and the acetate was subjected to chemical β-glucosylation of 19-COOH followed by deacetylation to afford compounds which have superior sweetness to S. In the same way, derivatives with superior sweetness were selectively prepared from RU through SM.
- Ohtani,Aikawa,Fujisawa,Kasai,Tanaka,Yamasaki
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p. 3172 - 3174
(2007/10/02)
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- Method for recovery of stevioside
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An improved method for the recovery of stevioside from Stevia rebaudiana Bertoni plants is provided which does not require the use of dangerous chemicals or special separation equipment such as ion exchange or chromatography. In the process the raw material, preferably in comminuted form is first extracted with water, the resulting aqueous extract is treated with a di- or tricarboxylic acid chelating agent to remove metallic and other impurities as well as to lower the pH to less than about 4. Subsequently a calcium-containing agent is added to precipitate out other impurities. The aqueous extract is essentially neutralized with an acid and is then subject to extraction with a water-immiscible solvent. Purified stevioside crystals are recovered by cooling the water layer obtained from said solvent extraction step.
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- TOTAL SYNTHESIS OF STEVIOSIDE
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Steviol 2 was transformed into stevioside 1 by applying the stereoselective methods of glycosidation.
- Ogawa, Tomoya,Nozaki, Michio,Matsui, Masanao
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p. 2641 - 2648
(2007/10/02)
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- Separation of sweet component from natural sweet extracts
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Glycosides such as stevioside, glycyrrhizin and neohesperidin dihydrochalcone are separated from non-glycosides such as phyllodulcin and perillartine by column chromatography using a porous gel.
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