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Synthesis of Anemoclemosides A and B, Two Saponins Isolated from Anemoclema glaucifolium
Author(s) -
Bouillon Marc E.,
Bertocco Katia,
Bischoff Laura,
Buri Michelle,
Davies Lucy R.,
Wilkinson Elizabeth J.,
Lahmann Martina
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001317
Subject(s) - chemistry , stereochemistry , rhamnose , glycosidic bond , saponin , arabinose , triterpene , ranunculaceae , acetal , glycoside , polysaccharide , organic chemistry , botany , xylose , enzyme , medicine , alternative medicine , pathology , fermentation , biology
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.