Ketene acetal and spiroacetal constituents of the marine fungus Aigialus parvus BCC 5311

J Nat Prod. 2004 Mar;67(3):457-60. doi: 10.1021/np030344d.

Abstract

Aigialone (1) and aigialospirol (2), two structurally unique compounds, were isolated from the mangrove fungus Aigialus parvus BCC 5311. The structure of the new ketene acetal 1 was elucidated by spectral analysis, and its relative stereochemistry was determined by X-ray crystallography. The stereochemistry of aigialospirol (2), elucidated by NMR spectral analysis, suggested that this compound is possibly derived from hypothemycin (3), a metabolite previously isolated from this same fungus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry
  • Acetals / isolation & purification*
  • Acetals / pharmacology
  • Ascomycota / chemistry*
  • Benzofurans / chemistry
  • Benzofurans / isolation & purification*
  • Benzofurans / pharmacology
  • Crystallography, X-Ray
  • Ethylenes
  • Ketones / chemistry
  • Ketones / isolation & purification*
  • Ketones / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Thailand
  • Zearalenone / analogs & derivatives
  • Zearalenone / chemistry
  • Zearalenone / pharmacology

Substances

  • Acetals
  • Benzofurans
  • Ethylenes
  • Ketones
  • aigialone
  • aigialospirol
  • hypothemycin
  • Zearalenone
  • ketene