Further investigation of the leaves of Acanthopanax divaricatus gave two analogues of chiisanoside, which is a lupane triterpenoid oligoglycosyl ester. The structures were established as 28-O-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl(1→6)β-d-glucopyranosyl esters of 1β,11α-dihydroxy-3-oxo-lup-20(29)-en-28-oic acid and 1(R),11α,22α-trihydroxy-3,4-seco-lupa-4(23),20(29)-diene-3,28-dioic acid 3,11α-lactone based on chemical and spectroscopic evidence. in biosynthetic terms, one is the precursor of chiisanoside and the other is an oxygenated derivative chiisanoside.
araliaceae, triterpenoid saponin, Acanthopanax divaricatus, lupane glycoside, chiisanoside, isochiisanoside, protochiisanoside, 22α-hydroxychiisanoside
Publication DOI: 10.1016/S0031-9422(97)00017-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: School of Pharmaceutical Sciences, Showa University, Hatamodai 1-5-8, Shinagawa-ku Tokyo 142, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, sugar analysis, TLC, enzymatic hydrolysis, acid hydrolysis, GC, chemical methods, extraction
Found