We report the isolation and complete structure of an isomer of rebaudioside D, known as rebaudioside D2. This novel steviol glycoside was isolated from a bioconversion reaction of rebaudioside A to rebaudioside D. Rebaudioside D2 possesses a relatively rare 1→6 sugar linkage, which was discovered by extensive analysis of NMR (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D TOCSY and NOESY) and mass spectral data.
(a) ChaturvedulaV.S.P., PrakashI. (2013) Structural characterization and hydrolysis studies of rebaudioside E, a minor sweet component of Stevia Rebaudiana. European Chemistry Bulletin, 2, 298–302; (b) Chaturvedula VSP, Rhea J, Milanowski D, Mocek U, Prakash I. (2012) Isolation and structure elucidation of two new minor diterpene glycosdies from Stevia rebaudiana. Organic Chemistry Current Research, 1, 102. doi:10.4172/2161-0401.1000102; (c) Prakash I, Campbell M, San Miguel RI, Chaturvedula VSP. (2013) Catalytic hydrogenation of the sweet principles of Stevia rebaudiana, rebaudiosde B, rebaudioside C and rebaudioside D and sensory evaluation of their reduced derivatives. International Journal of Molecular Science, 13, 15126–15136; (d) Prakash I, Chaturvedula VSP. (2013) Additional minor diterpene glycosides from Stevia rebaudiana Bertoni. Molecules, 18, 13510–13519; (e) Chaturvedula VSP, Rhea J, Milanowski D, Mocek U, Prakash I. (2011) Two minor diterpene glycosides from the leaves of Stevia rebaudiana. Natural Products Communications, 6, 175–178.
2.
LewisW.H. (1992) Early uses of Stevia rebaudiana (Asteraceae) leaves as a sweetener in Paraguay. Economic Botany, 46, 336–337.
3.
(a) CeunenS., GeunsJ.M.C. (2013) Steviol glycosides: Chemical diversity, metabolism, and function. Journal of Natural Products, 76, 1201–1228; (b) Ohta M, Sasa S, Inoue A, Tamai T, Fujita I, Morita K, Matsuura F. (2010) Characterization of novel steviol glycosides from leaves of Stevia rebaudiana Morita. Journal of Applied Glycoscience, 57, 199–209; (c) Wolwer-Rieck U. (2012) The leaves of Stevia rebaudiana (Bertoni), Their constituents and the analyses thereof: A review. Journal of Agricultural and Food Chemistry, 60, 886–895; (d), Starratt AN, Kirby CW, Pocs R, Brandle JE. (2002) Rebaudioside F, a diterpene glycoside from Stevia rebaudiana. Phytochemistry, 59, 367–370; (e) Sakamoto I, Yamasaki K, Tanaka O. (1977) Application of 13C-NMR spectroscopy to chemistry of natural glycosides: Rebaudioside-C, a new sweet diterpene glycosides of Stevia rebaudiana. Chemical and Pharmaceutical Bulletin, 25, 844–846; (f) Sakamoto I, Yamasaki K, Tanaka O. (1977) Application of 13C-NMR spectroscopy to chemistry of plant glycosides: Rebaudioside-D and -E, new sweet diterpene-glucosides of Stevia rebaudiana Bertoni. Chemical and Pharmaceutical Bulletin, 25, 3437–3439; (g) Mosettig E, Beglinger U, Dolder F, Lichti H, Quitt P, Waters JA. (1963) The absolute configuration of steviol and isosteviol. Journal of the American Chemical Society, 85, 2305–2309.
4.
JEFCA.2010. Steviol glycosides. In Combined Compendium of Food Additive Specifications [Online Edition]. Food and Agriculture Organization of the United Nations (FAO), Joint FAO/WHO Expert Committee on Food Additives (JECFA), Rome. Italy. Available from: http://www.fao.org/ag/agn/jecfa-additives/specs/monograph10/additive-442-m10.pdf.
5.
(a) BrandleJ.E., StarrattA.N., GijzenM. (1998) Stevia rebaudiana: Its agricultural, biological, and chemical properties. Canadian Journal of Plant Science, 78, 527–536; (b), DuBois GE, Prakash I. (2012) Non-caloric sweeteners, sweetness modulators, and sweetener enhancers. Annual Review of Food Science and Technology, 3, 353–380; (c) Kinghorn AD, Kim NC, Kim DHL. (1999) Terpenoid glycoside sweeteners. In Naturally Occurring Glycosides.IkanR. (Ed.). John Wiley & Sons, New York, USA, 399–429.
6.
PrakashI., DuBoisG.E., ClosJ.F., WilkensK.L., FosdickL.E. (2008) Development of rebiana, a natural, non-caloric sweetener. Food and Chemical Toxicity, 46, S75–S82.
7.
(a) CarakostasM.C., CurryL.L., BoileauA.C., BrusickD.L. (2008) Overview: the history, technical function and safety of rebaudioside A, a naturally occurring steviol glycoside, for use in food and beverage. Food and Chemical Toxicity, 46, S1–S10; (b), Chaturvedula VSP, Prakash I. (2012) Spectral analysis and chemical studies of the sweet constituent, rebaudioside A. European Journal of Medicinal Plants, 2, 57–65.
8.
PrakashI., ChaturvedulaV.S.P., MarkosyanA. (2013) Isolation, characterization and sensory evaluation of a hexa β-D-glucopyranosyl diterpene from Stevia rebaudiana. Natural Product Communications, 8, 1523–1526.
9.
PrakashI., MarkosyanA., BundersC. (2014) Development of next generation Stevia sweetener: Rebaudioside M. Foods, 3, 162–175.
10.
PrakashI., BundersC., DevkotaK.P., CharanR.D., RamirezC., PriedemannC., MarkosyanA. (2014) Isolation and characterization of a novel rebaudioside M isomer from the bioconversion reaction of rebaudioside A and NMR comparison studies of rebaudioside M isolated from Stevia rebaudiana Bertoni and Stevia rebaudiana Morita. Biomolecules, 4, 374–389.
11.
(a) ChaturvedulaV.S.P., ClosJ.F., RheaJ., MilanowskiD., MocekU., DuBoisG.E., PrakashI. (2011) Minor diterpene glycosides from the leaves of Stevia rebaudiana. Phytochemistry Letters, 4, 209–212; (b) Chaturvedula VSP, Mani U, Prakash I. (2011) Structures of the novel α-glucosyl linked diterpene glycosides from Stevia rebaudiana. Carbohydrate Research, 346, 2034–2038.
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