Structure and absolute stereochemistry of nortriterpenoids from Schisandra chinensis (Turcz.) Baill

Jian Rong Wang, Tibor Kurtán, Attila Mándi, Yue Wei Guo

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)5471-5482
Number of pages12
JournalEuropean Journal of Organic Chemistry
Issue number28
DOIs
Publication statusPublished - Oct 1 2012

Keywords

  • Biogenetic pathway
  • Circular dichroism
  • Natural products
  • Structure elucidation
  • Terpenoids

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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