Cucurbitane-type triterpenoids from the fruit of Momordica charantia

J Nat Prod. 2005 May;68(5):807-9. doi: 10.1021/np040218p.

Abstract

The structures of three new cucurbitane-type triterpenoids isolated from the methanol extract of the fruit of Japanese Momordica charantia were established as (19R,23E)-5beta,19-epoxy-19-methoxycucurbita-6,23,25-trien-3beta-ol (1), (23E)-3beta-hydroxy-7beta-methoxycucurbita-5,23,25-trien-19-al (2), and (23E)-3beta-hydroxy-7beta,25-dimethoxycucurbita-5,23-dien-19-al (3) on the basis of spectroscopic methods. These compounds were accompanied by the known (19R,23E)-5beta,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3beta-ol (4) and (19R,23E)-5beta,19-epoxy-19-methoxycucurbita-6,23-diene-3beta,25-diol (5). This is the first report of the isolation of tetracyclic triterpenoids possessing a delta23,25-conjugated diene system, viz., 1 and 2, from a natural source.

MeSH terms

  • Fruit / chemistry
  • Japan
  • Molecular Structure
  • Momordica charantia / chemistry*
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification*

Substances

  • (19R,23E)-5beta,19-epoxy-19-methoxycucurbita-6,23,25-trien-3beta-ol
  • (23E)-3beta-hydroxy-7beta,25-dimethoxycucurbita-5,23-dien-19-al
  • (23E)-3beta-hydroxy-7beta-methoxycucurbita-5,23,25-trien-19-al
  • Triterpenes