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Structure and Absolute Stereochemistry of Nortriterpenoids from Schisandra chinensis (Turcz.) Baill
Author(s) -
Wang JianRong,
Kurtán Tibor,
Mándi Attila,
Guo YueWei
Publication year - 2012
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.201200557
Subject(s) - chemistry , schisandra , stereochemistry , circular dichroism , schisandra chinensis , absolute configuration , side chain , ring (chemistry) , organic chemistry , medicine , alternative medicine , pathology , traditional chinese medicine , polymer
A varierty of previously unreported compounds, the cagelike hexacyclic schicagenin‐type nortriterpenoid 1 , three pre‐schisanartane‐type nortriterpenoids 2 – 4 , seven C 29 nortriterpenoids 5 – 11 possessing an uncommon pentacyclic carbon skeleton characterized by a 5/5/7/7/5 fused‐ring motif bearing a C 9 side chain, two highly oxygenated C 28 nortriterpenoids 12 and 13 containing an unprecedented 5/5/7 ring nucleus bearing a C 15 side chain, and the known C 29 nortriterpenoid 14 were isolated from the leaves and stems of the Chinese medicinal plant Schisandra chinensis . The structures of these new metabolites were elucidated by means of detailed spectroscopic analysis. The absolute configurations of 4 and 5 were determined by time‐dependent density functional theory electronic circular dichroism (TDDFT ECD) calculations, allowing the assignment of the absolute configurations of analogous compounds 1 – 3 and 6 – 13 .