New oxidized sterols from Aspergillus awamori and the endo-boat conformation adopted by the cyclohexene oxide system

Magn Reson Chem. 2010 Jan;48(1):38-43. doi: 10.1002/mrc.2536.

Abstract

Two new oxidized sterols 1 and 2 were obtained from the active fraction of a mangrove fungus Aspergillus awamori isolated from the soils around the mangrove plant Acrostichum speciosum. Their structures were elucidated using spectroscopic methods as 22E-7alpha-methoxy-5alpha,6alpha-epoxyergosta-8(14),22-dien-3beta-ol (1) and 22E-3beta-hydroxy-5alpha,6alpha,8alpha,14alpha-diepoxyergosta-22-en-7-one (2). The NMR data and complete assignments for both DMSO-d(6) and CDCl(3) were given. Their cytotoxic activity against A549 cell line was evaluated. Furthermore, the detailed conformation analysis for ring B (cyclohexene oxide system) of sterol 1 was given on the basis of NOEs. The endo-boat conformation was considered as the preferred conformation for ring B rather than half-chair conformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspergillus / chemistry*
  • Cyclohexenes / chemistry*
  • Ergosterol / chemistry
  • Ergosterol / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism
  • Sterols / chemistry
  • Sterols / isolation & purification

Substances

  • 22E-3beta-hydroxy-5alpha,6alpha,8alpha,14alpha-diepoxyergosta-22-en-7-one
  • Cyclohexenes
  • Sterols
  • cyclohexene oxide
  • Ergosterol