Synthesis of Anemoclemosides A and B, two Saponins Isolated from Anemoclema glaucifolium

Marc Bouillon; Katia Bertocco; Laura Bischoff; Michelle Buri; lucy Rebecca Davies; Elizabeth Jane Wilkinson; Martina Lahmann

doi:10.1002/ejoc.202001317

Synthesis of Anemoclemosides A and B, two Saponins Isolated from Anemoclema glaucifolium

Marc Bouillon, Katia Bertocco, Laura Bischoff, Michelle Buri, lucy Rebecca Davies, Elizabeth Jane Wilkinson, Martina Lahmann

School of Environmental & Natural Sciences

Bangor University

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Abstract

Steroidal and triterpenoid saponins are attractive for their wide‐ranging pharmacological properties. The triterpenoid saponins Anemoclemoside A and B are root constituents of the Chinese folk medicinal plant Anemoclema glaucifolium (Ranunculaceae). Both compounds feature an unusual cyclic acetal linkage to the carbohydrate L‐arabinose in its open chain form rather than the typical glycosidic bond present in normal saponins. The straightforward and scalable syntheses of both saponins starting from L‐arabinose as well as L‐lyxose and L‐rhamnose are described.

Original language	English
Pages (from-to)	7470-7473
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	48
Early online date	19 Oct 2020
DOIs	https://doi.org/10.1002/ejoc.202001317
Publication status	Published - 31 Dec 2020

Keywords

Anemoclemosides
Cyclic acetal glycosidic linkage
Glycosylation
Hederagenin glycosides
Saponins

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10.1002/ejoc.202001317

ejoc.202001317Accepted author manuscript, 1.14 MB

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title = "Synthesis of Anemoclemosides A and B, two Saponins Isolated from Anemoclema glaucifolium",

abstract = "Steroidal and triterpenoid saponins are attractive for their wide‐ranging pharmacological properties. The triterpenoid saponins Anemoclemoside A and B are root constituents of the Chinese folk medicinal plant Anemoclema glaucifolium (Ranunculaceae). Both compounds feature an unusual cyclic acetal linkage to the carbohydrate L‐arabinose in its open chain form rather than the typical glycosidic bond present in normal saponins. The straightforward and scalable syntheses of both saponins starting from L‐arabinose as well as L‐lyxose and L‐rhamnose are described.",

keywords = "Anemoclemosides, Cyclic acetal glycosidic linkage, Glycosylation, Hederagenin glycosides, Saponins",

author = "Marc Bouillon and Katia Bertocco and Laura Bischoff and Michelle Buri and Davies, \{lucy Rebecca\} and Wilkinson, \{Elizabeth Jane\} and Martina Lahmann",

note = "Innovate UK. Grant Number: 102101 BEACON Biorefining Centre of Excellence Innovate UK. Grant Number: 101091",

year = "2020",

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doi = "10.1002/ejoc.202001317",

language = "English",

volume = "2020",

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journal = "European Journal of Organic Chemistry",

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number = "48",

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TY - JOUR

T1 - Synthesis of Anemoclemosides A and B, two Saponins Isolated from Anemoclema glaucifolium

AU - Bouillon, Marc

AU - Bertocco, Katia

AU - Bischoff, Laura

AU - Buri, Michelle

AU - Davies, lucy Rebecca

AU - Wilkinson, Elizabeth Jane

AU - Lahmann, Martina

N1 - Innovate UK. Grant Number: 102101 BEACON Biorefining Centre of Excellence Innovate UK. Grant Number: 101091

PY - 2020/12/31

Y1 - 2020/12/31

N2 - Steroidal and triterpenoid saponins are attractive for their wide‐ranging pharmacological properties. The triterpenoid saponins Anemoclemoside A and B are root constituents of the Chinese folk medicinal plant Anemoclema glaucifolium (Ranunculaceae). Both compounds feature an unusual cyclic acetal linkage to the carbohydrate L‐arabinose in its open chain form rather than the typical glycosidic bond present in normal saponins. The straightforward and scalable syntheses of both saponins starting from L‐arabinose as well as L‐lyxose and L‐rhamnose are described.

AB - Steroidal and triterpenoid saponins are attractive for their wide‐ranging pharmacological properties. The triterpenoid saponins Anemoclemoside A and B are root constituents of the Chinese folk medicinal plant Anemoclema glaucifolium (Ranunculaceae). Both compounds feature an unusual cyclic acetal linkage to the carbohydrate L‐arabinose in its open chain form rather than the typical glycosidic bond present in normal saponins. The straightforward and scalable syntheses of both saponins starting from L‐arabinose as well as L‐lyxose and L‐rhamnose are described.

KW - Anemoclemosides

KW - Cyclic acetal glycosidic linkage

KW - Glycosylation

KW - Hederagenin glycosides

KW - Saponins

U2 - 10.1002/ejoc.202001317

DO - 10.1002/ejoc.202001317

M3 - Article

SN - 1434-193X

VL - 2020

SP - 7470

EP - 7473

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 48

ER -

Synthesis of Anemoclemosides A and B, two Saponins Isolated from Anemoclema glaucifolium

Abstract

Keywords

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