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Absolute configuration of (-)-gambogic acid, an antitumor agent.

Authors
  • Ren, Yulin
  • Yuan, Chunhua
  • Chai, Hee-byung
  • Ding, Yuanqing
  • Li, Xing-Cong
  • Ferreira, Daneel
  • Kinghorn, A Douglas
Type
Published Article
Journal
Journal of Natural Products
Publisher
American Chemical Society
Publication Date
Mar 25, 2011
Volume
74
Issue
3
Pages
460–463
Identifiers
DOI: 10.1021/np100422z
PMID: 21067206
Source
Medline
License
Unknown

Abstract

(-)-Gambogic acid (1), a biologically active "caged xanthone" from gamboge, the dried resin of Garcinia hanburyi, is of interest as a potential anticancer agent. The planar structure of (-)-gambogic acid has been determined previously by analysis of its detailed NMR data and confirmed by single-crystal X-ray diffraction, with the absolute configuration at C-13 deduced as R through a series of chemical degradations. Using (-)-morellic acid (2), an analogue of (-)-gambogic acid, as a model compound, the 5R, 7S, 10aS, 13R, 27S absolute configuration of (-)-gambogic acid was determined for the first time by comparison of physical and spectroscopic data, especially experimental and calculated electronic circular dichroism.

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