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Molecules 2014, 19(12), 20280-20294; doi:10.3390/molecules191220280

Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides

Organic Chemistry Department, The Coca-Cola Company, Global Research and Development, One Coca-Cola Plaza, Atlanta, GA 30313, USA
Current address: Natural Products Research Group, Wisdom Natural Brands, 1203 W San Pedro Street, Gilbert, AZ 85233, USA
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Author to whom correspondence should be addressed.
Received: 10 October 2014 / Revised: 26 November 2014 / Accepted: 28 November 2014 / Published: 4 December 2014
(This article belongs to the Section Natural Products)
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Abstract

Four new minor diterpene glycosides with a rare α-glucosyl linkage were isolated from a cyclodextrin glycosyltransferase glucosylated stevia extract containing more than 98% steviol glycosides. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-α-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl) ester] (1), 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl ester] (2), 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester (3), and 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-α-D-glucopyranosyl)-α-D-glucopyranosyl)-α-D-glucopyranosyl)-β-D-glucopyranosyl- β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-α-D-glucopyranosyl-β-D-glucopyranosyl) ester] (4) on the basis of extensive NMR and mass spectral (MS) data as well as hydrolysis studies. View Full-Text
Keywords: Stevia rebaudiana; compositae; asteraceae; glycosylation; diterpenoid glycosides; NMR; MS; hydrolysis studies Stevia rebaudiana; compositae; asteraceae; glycosylation; diterpenoid glycosides; NMR; MS; hydrolysis studies
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Prakash, I.; Chaturvedula, V.S.P. Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides. Molecules 2014, 19, 20280-20294.

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