New ent-kaurane diterpenoids with anti-platelet aggregation activity from Annona squamosa

J Nat Prod. 2002 Oct;65(10):1462-7. doi: 10.1021/np020191e.

Abstract

A phytochemical investigation on the stems of Annona squamosa led to the isolation of six new ent-kaurane diterpenoids, annomosin A (16beta-hydroxy-19-al-ent-kauran-17-yl 16beta-hydro-19-al-ent-kauran-17-oate) (1), annosquamosin C (16alpha-hydro-17-hydroxy-19-nor-ent-kauran-4alpha-ol) (2), annosquamosin D (16beta-acetoxy-17-hydroxy-19-nor-ent-kauran-4alpha-ol) (3), annosquamosin E (16beta-hydroxy-17-acetoxy-19-nor-ent-kauran-4alpha-formate) (4), annosquamosin F (16beta-hydroxy-17-acetoxy-18-nor-ent-kauran-4beta-hydroperoxide) (5), and annosquamosin G (16beta,17-dihydroxy-18-nor-ent-kauran-4beta-hydroperoxide) (6), along with 14 known ent-kaurane diterpenoids. The structures of 1-6 were elucidated by spectroscopic data interpretation. Compound 1 is the first dimeric ent-kaurane derivative to have been reported from a plant in the family Annonaceae. Certain useful NMR data were generalized to determine the stereochemistry of C-16 among the ent-kaurane diterpenoids investigated. ent-Kaur-16-en-19-oic acid (9) and 16alpha-hydro-19-al-ent-kauran-17-oic acid (17) showed complete inhibitory effects on rabbit platelet aggregation at 200 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Annona / chemistry*
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Platelet Aggregation Inhibitors / chemistry
  • Platelet Aggregation Inhibitors / isolation & purification*
  • Platelet Aggregation Inhibitors / pharmacology
  • Rabbits
  • Spectrum Analysis

Substances

  • Diterpenes
  • Platelet Aggregation Inhibitors