beta-Methoxy-gamma-methylene-alpha,beta-unsaturated-gamma-butyrolactones from Artabotrys hexapetalus

Phytochemistry. 2002 Jan;59(1):99-104. doi: 10.1016/s0031-9422(01)00433-2.

Abstract

The dichloromethane extract of the aerial parts of Artabotrys hexapetalus afforded three beta-methoxy-gamma-methylene-alpha,beta-unsaturated-gamma-butyrolactones, which are proposed to be derived from a C(18) unsaturated fatty acid by a biosynthetic route similar to that proposed for the Annonaceous acetogenins. The structure of the unique beta-methoxy-gamma-methylene-substituted, alpha,beta-unsaturated-gamma-butyrolactone ring of artapetalins A-C (1-3) was determined by 2D-NMR spectroscopic analyses. Two unusual simple butyrolactones, (+)-tulipalin B and (2R,3R)- 3-hydroxy-2-methylbutyrolactone were also isolated from this species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification
  • Annonaceae / chemistry*
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Bridged-Ring Compounds / chemistry
  • Bridged-Ring Compounds / isolation & purification

Substances

  • Antimalarials
  • Bridged-Ring Compounds
  • artapetalin A
  • artapetalin B
  • artapetalin C
  • 4-Butyrolactone