Verbesinosides A-F, 15,27-cyclooleanane saponins from the American native plant Verbesina virginica

  • J Nat Prod. 2009 Jun;72(6):1022-7. doi: 10.1021/np900180y.
Wen-Hui Xu  1 ,  Melissa R Jacob ,  Ameeta K Agarwal ,  Alice M Clark ,  Zong-Suo Liang ,  Xing-Cong Li
Affiliations
  • 1. National Center for Natural Products Research, Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
PMID: 19485332 DOI: 10.1021/np900180y
Abstract

Verbesinosides A-F (1-6), six new 15,27-cyclooleanane-type triterpenoid saponins carrying different aromatic acyl moieties on the aglycon, were isolated from the leaves and flowers of Verbesina virginica. Their structures were established by interpretation of spectroscopic data and chemical methods. The representative major saponin, verbesinoside A (1), has the structure 21-trimethoxybenzoyl 15alpha,27-cycloolean-12-en-3beta,21beta-diol-28-oic acid 3-O-beta-D-xylopyranosyl(1-->4)-beta-D-xylopyranosyl(1-->2)-beta-D-glucopyranoside. This is the first report of triterpenoid saponins possessing the unique 15,27-cyclooleanane skeleton. The anisotropic effects of the aromatic acyl moieties on the triterpenoid skeleton are discussed.

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