Lupeol

Acta Crystallogr C. 2009 Mar;65(Pt 3):o97-9. doi: 10.1107/S0108270109004910. Epub 2009 Feb 21.

Abstract

The title compound [systematic name: 3beta-lup-20(29)-en-3-ol], C(30)H(50)O, was isolated from the leaves of Garcinia brasiliensis (common name: bacupari; a member of the Guttiferae family) and has been shown to have many useful medicinal and biological properties. The lupeol molecule consists of four six-membered rings (adopting chair conformations) and one five-membered ring (with an envelope conformation), all fused in trans fashion. Lupeol is isomorphic with the pentacyclic triterpene 3beta,30-dihydroxylup-20(29)-ene, which differs from lupeol due to the presence of an additional hydroxy group. The crystal packing is stabilized by van der Waals interactions and intermolecular O-H...O hydrogen bonds, giving rise to an infinite helical chain along the c axis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Garcinia / chemistry
  • Molecular Structure
  • Pentacyclic Triterpenes
  • Triterpenes / chemistry*

Substances

  • Pentacyclic Triterpenes
  • Triterpenes
  • lupeol