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Structures of some novel ?-glucosyl diterpene glycosides from the glycosylation of steviol glycosides.

ABSTRACT: Four new minor diterpene glycosides with a rare ?-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-?-D-glucopyranosyl-3-O-(4-O-?-D-glucopyranosyl)-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-?-D-glucopyranosyl-?-D-glucopyranosyl) ester] (1), 13-[(2-O-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-(4-O-(4-O-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl ester] (2), 13-[(2-O-?-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl-?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid ?-D-glucopyranosyl ester (3), and 13-[(2-O-?-D-glucopyranosyl-3-O-(4-O-(4-O-(4-O-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl)-?-D-glucopyranosyl- ?-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(4-O-?-D-glucopyranosyl-?-D-glucopyranosyl) ester] (4) on the basis of extensive NMR and mass spectral (MS) data as well as hydrolysis studies.

SUBMITTER: Prakash I 

PROVIDER: S-EPMC6271715 | biostudies-literature | 2014 Dec

REPOSITORIES: biostudies-literature

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Structures of some novel α-glucosyl diterpene glycosides from the glycosylation of steviol glycosides.

Prakash Indra I   Chaturvedula Venkata Sai Prakash VS  

Molecules (Basel, Switzerland) 20141204 12

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-  ...[more]

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