The anti-inflammatory triterpenoid methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate

Acta Crystallogr C. 2002 Mar;58(Pt 3):o199-200. doi: 10.1107/s010827010102176x. Epub 2002 Feb 28.

Abstract

The title compound, C(32)H(43)NO(4) x CH(4)O x H(2)O, has a nearly planar cyano-enone A ring in an otherwise normal oleanane triterpenoid. Rings A, B and C are non-chairs, but rings D and E adopt essentially cyclohexane chair conformations. The structure clearly establishes the C-D-E ring stereochemistry as trans-syn-cis, as predicted from a nuclear Overhauser effect (NOE) NMR measurement.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry*
  • Triterpenes / chemistry*

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Triterpenes
  • methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate
  • Oleanolic Acid