Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides
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-glucopyr...
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doaj-c9cc7ff6180f41898fffdde80fbaaccb2020-11-24T22:39:28ZengMDPI AGMolecules1420-30492014-12-011912202802029410.3390/molecules191220280molecules191220280Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol GlycosidesIndra Prakash0Venkata Sai Prakash Chaturvedula1Organic Chemistry Department, The Coca-Cola Company, Global Research and Development, One Coca-Cola Plaza, Atlanta, GA 30313, USAOrganic Chemistry Department, The Coca-Cola Company, Global Research and Development, One Coca-Cola Plaza, Atlanta, GA 30313, USAFour 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.http://www.mdpi.com/1420-3049/19/12/20280Stevia rebaudianacompositaeasteraceaeglycosylationditerpenoid glycosidesNMRMShydrolysis studies |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Indra Prakash Venkata Sai Prakash Chaturvedula |
spellingShingle |
Indra Prakash Venkata Sai Prakash Chaturvedula Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides Molecules Stevia rebaudiana compositae asteraceae glycosylation diterpenoid glycosides NMR MS hydrolysis studies |
author_facet |
Indra Prakash Venkata Sai Prakash Chaturvedula |
author_sort |
Indra Prakash |
title |
Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides |
title_short |
Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides |
title_full |
Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides |
title_fullStr |
Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides |
title_full_unstemmed |
Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides |
title_sort |
structures of some novel α-glucosyl diterpene glycosides from the glycosylation of steviol glycosides |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2014-12-01 |
description |
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. |
topic |
Stevia rebaudiana compositae asteraceae glycosylation diterpenoid glycosides NMR MS hydrolysis studies |
url |
http://www.mdpi.com/1420-3049/19/12/20280 |
work_keys_str_mv |
AT indraprakash structuresofsomenovelaglucosylditerpeneglycosidesfromtheglycosylationofsteviolglycosides AT venkatasaiprakashchaturvedula structuresofsomenovelaglucosylditerpeneglycosidesfromtheglycosylationofsteviolglycosides |
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