Anti-androgenic triterpenoids from the Brazilian medicinal plant, Cordia multispicata

Chem Pharm Bull (Tokyo). 2001 Aug;49(8):954-7. doi: 10.1248/cpb.49.954.

Abstract

Compounds 1-6 were isolated from the AcOEt soluble fraction of leaves of the Brazilian medicinal plant, Cordia multispicata, and their structures were elucidated to be 3beta,25-epoxy-21beta-acetoxy-3alpha,22beta-dihydroxyurs-12-en-28-al (1), 3beta,25-epoxy-28-acetoxy-3alpha,21beta,22beta-trihydroxyurs-12-ene (2), 21beta-acetoxy-22beta-hydroxy-3-oxours-12-en-28-al (3), 28-acetoxy-6beta, 21beta,22beta-trihydroxy-3-oxours-12-ene (4), 21beta,22beta-dihydroxy-3-oxours-1 2-en-28-al (5) and 3beta,21beta,22beta-trihydroxyurs-I2-en-28-al (6), respectively, by means of spectral data, especially two dimensional NMR techniques. Triterpenes having the hemiketal structure at the A-ring, an acyloxy group at C-22 and/or ketone at C-3 showed potent anti-androgenic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3-Oxo-5-alpha-Steroid 4-Dehydrogenase / metabolism
  • 5-alpha Reductase Inhibitors
  • Androgen Antagonists / chemistry*
  • Androgen Antagonists / isolation & purification
  • Androgen Antagonists / pharmacology*
  • Brazil
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification
  • Flavonoids / pharmacology
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Plants, Medicinal / chemistry*
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • 5-alpha Reductase Inhibitors
  • Androgen Antagonists
  • Flavonoids
  • Plant Extracts
  • Triterpenes
  • 3-Oxo-5-alpha-Steroid 4-Dehydrogenase