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

J Nat Prod. 2011 Mar 25;74(3):460-3. doi: 10.1021/np100422z. Epub 2010 Nov 10.

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Drug Screening Assays, Antitumor
  • Garcinia / chemistry*
  • HT29 Cells
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Resins, Plant / chemistry*
  • Stereoisomerism
  • Xanthones / chemistry*
  • Xanthones / isolation & purification
  • Xanthones / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Resins, Plant
  • Xanthones
  • morellic acid
  • gambogic acid