Regioselective Acylation of Ginsenosides by Novozyme 435 to Generate Molecular Diversity
Abstract Ginsenosides are major bioactive constituents of ginseng ( Panax spp.; Araliaceae), a traditional Chinese medicinal herb. In order to increase the molecular diversity and broaden the potential usage of ginsenosides, ginsenosides Rd ( 1 ), Rg3 ( 2 ), (20 R )‐Rg3 ( 3 ), Rh2 ( 4 ), Re ( 5 ), R...
Published in: | Helvetica Chimica Acta |
---|---|
Main Authors: | , , , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley
2004
|
Subjects: | |
Online Access: | http://dx.doi.org/10.1002/hlca.200490165 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fhlca.200490165 https://onlinelibrary.wiley.com/doi/pdf/10.1002/hlca.200490165 |
id |
crwiley:10.1002/hlca.200490165 |
---|---|
record_format |
openpolar |
spelling |
crwiley:10.1002/hlca.200490165 2024-06-02T07:57:57+00:00 Regioselective Acylation of Ginsenosides by Novozyme 435 to Generate Molecular Diversity Teng, Rongwei Ang, Chingseng McManus, David Armstrong, David Mau, Shaiolim Bacic, Antony 2004 http://dx.doi.org/10.1002/hlca.200490165 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fhlca.200490165 https://onlinelibrary.wiley.com/doi/pdf/10.1002/hlca.200490165 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Helvetica Chimica Acta volume 87, issue 7, page 1860-1872 ISSN 0018-019X 1522-2675 journal-article 2004 crwiley https://doi.org/10.1002/hlca.200490165 2024-05-03T10:52:26Z Abstract Ginsenosides are major bioactive constituents of ginseng ( Panax spp.; Araliaceae), a traditional Chinese medicinal herb. In order to increase the molecular diversity and broaden the potential usage of ginsenosides, ginsenosides Rd ( 1 ), Rg3 ( 2 ), (20 R )‐Rg3 ( 3 ), Rh2 ( 4 ), Re ( 5 ), Rh1 ( 8 ), Rg2 ( 9 ), gypenoside XVII ( 6 ), and pseudoginsenoside F11 ( 7 ) were regioselectively acylated with vinyl acetate, catalyzed by Novozyme 435 (lipase B from Candida antarctica ), in organic solvents to afford different mono‐acetyl ginsenosides. Ginsenoside Rd ( 1 ) was also acylated with vinyl decanoate or vinyl cinnamate to generate 1b and 1c , respectively. Acylation of glucosylated ginsenosides ( 1 – 4, 6, 8 ) occurred at the primary 6‐OH function of the terminal glucose (Glc) moiety of the sugar at C(3) or C(20) of the dammarane‐type aglycone. In contrast, ginsenosides 5, 7 , and 9 , containing mixed sugar moieties, resulted in acylation of both the rhamnose (Rha) and the glucose (Glc) moieties. In the case of ginsenoside Re ( 5 ) and pseudoginsenoside F11 ( 7 ), acylation at the secondary 4‐OH function of the terminal Rha moiety, attached at C(3) of the aglycone, is preferred. The structures of all acylated products were determined by extensive MALDI‐TOF‐MS and NMR analyses. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Helvetica Chimica Acta 87 7 1860 1872 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
Abstract Ginsenosides are major bioactive constituents of ginseng ( Panax spp.; Araliaceae), a traditional Chinese medicinal herb. In order to increase the molecular diversity and broaden the potential usage of ginsenosides, ginsenosides Rd ( 1 ), Rg3 ( 2 ), (20 R )‐Rg3 ( 3 ), Rh2 ( 4 ), Re ( 5 ), Rh1 ( 8 ), Rg2 ( 9 ), gypenoside XVII ( 6 ), and pseudoginsenoside F11 ( 7 ) were regioselectively acylated with vinyl acetate, catalyzed by Novozyme 435 (lipase B from Candida antarctica ), in organic solvents to afford different mono‐acetyl ginsenosides. Ginsenoside Rd ( 1 ) was also acylated with vinyl decanoate or vinyl cinnamate to generate 1b and 1c , respectively. Acylation of glucosylated ginsenosides ( 1 – 4, 6, 8 ) occurred at the primary 6‐OH function of the terminal glucose (Glc) moiety of the sugar at C(3) or C(20) of the dammarane‐type aglycone. In contrast, ginsenosides 5, 7 , and 9 , containing mixed sugar moieties, resulted in acylation of both the rhamnose (Rha) and the glucose (Glc) moieties. In the case of ginsenoside Re ( 5 ) and pseudoginsenoside F11 ( 7 ), acylation at the secondary 4‐OH function of the terminal Rha moiety, attached at C(3) of the aglycone, is preferred. The structures of all acylated products were determined by extensive MALDI‐TOF‐MS and NMR analyses. |
format |
Article in Journal/Newspaper |
author |
Teng, Rongwei Ang, Chingseng McManus, David Armstrong, David Mau, Shaiolim Bacic, Antony |
spellingShingle |
Teng, Rongwei Ang, Chingseng McManus, David Armstrong, David Mau, Shaiolim Bacic, Antony Regioselective Acylation of Ginsenosides by Novozyme 435 to Generate Molecular Diversity |
author_facet |
Teng, Rongwei Ang, Chingseng McManus, David Armstrong, David Mau, Shaiolim Bacic, Antony |
author_sort |
Teng, Rongwei |
title |
Regioselective Acylation of Ginsenosides by Novozyme 435 to Generate Molecular Diversity |
title_short |
Regioselective Acylation of Ginsenosides by Novozyme 435 to Generate Molecular Diversity |
title_full |
Regioselective Acylation of Ginsenosides by Novozyme 435 to Generate Molecular Diversity |
title_fullStr |
Regioselective Acylation of Ginsenosides by Novozyme 435 to Generate Molecular Diversity |
title_full_unstemmed |
Regioselective Acylation of Ginsenosides by Novozyme 435 to Generate Molecular Diversity |
title_sort |
regioselective acylation of ginsenosides by novozyme 435 to generate molecular diversity |
publisher |
Wiley |
publishDate |
2004 |
url |
http://dx.doi.org/10.1002/hlca.200490165 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fhlca.200490165 https://onlinelibrary.wiley.com/doi/pdf/10.1002/hlca.200490165 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Helvetica Chimica Acta volume 87, issue 7, page 1860-1872 ISSN 0018-019X 1522-2675 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/hlca.200490165 |
container_title |
Helvetica Chimica Acta |
container_volume |
87 |
container_issue |
7 |
container_start_page |
1860 |
op_container_end_page |
1872 |
_version_ |
1800741190569558016 |