Aspergillusol A, an alpha-glucosidase inhibitor from the marine-derived fungus Aspergillus aculeatus

J Nat Prod. 2009 Nov;72(11):2049-52. doi: 10.1021/np9003883.

Abstract

A new tyrosine-derived metabolite, aspergillusol A (4), was isolated on a gram scale, together with a methyl ester of 4-hydroxyphenylpyruvic acid oxime (5) and secalonic acid A, from the marine-derived fungus Aspergillus aculeatus CRI323-04. The tetraol in 4 was identified as erythritol by comparison of the 1H NMR spectrum of its benzoylated derivative with those of benzoylated erythritol (7) and D-threitol (8), as well as by cellulose-based chiral HPLC analysis. Aspergillusol A (4) selectively inhibited alpha-glucosidase from the yeast Saccharomyces cerevisiae, but it was inactive toward the alpha-glucosidase from the bacterium Bacillus stearothermophilus.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aspergillus / chemistry*
  • Geobacillus stearothermophilus / drug effects
  • Geobacillus stearothermophilus / enzymology*
  • Glycoside Hydrolase Inhibitors*
  • Marine Biology
  • Molecular Structure
  • Saccharomyces cerevisiae / drug effects
  • Saccharomyces cerevisiae / enzymology*
  • Stereoisomerism
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemistry
  • Tyrosine / isolation & purification
  • Tyrosine / pharmacology
  • Xanthones / isolation & purification

Substances

  • Glycoside Hydrolase Inhibitors
  • Xanthones
  • aspergillusol A
  • Tyrosine
  • secalonic acid