Microbial conversion of mevinolin

J Antibiot (Tokyo). 1997 Sep;50(9):750-4. doi: 10.7164/antibiotics.50.750.

Abstract

About 3000 microorganisms (bacteria, Actinomyces, Zygomyces, Deuteromyces) were screened for their capacity to convert mevinolin. Absidia coerulea IDR 705 was found to produce two hydroxylated derivatives of mevinolin, 2 and 3. Compound 2 is a new transformation product while compound 3 was described as a chemical modification product of mevinolin. By combination of spectroscopic techniques, the structures of 2 and 3 were identified with beta,delta-dihydroxy-7-(1,2-dihydro-2-hydroxymethyl-6-methyl-naphthal en-1-yl)-heptanoic acid delta-lactone and beta,delta-dihydroxy-7-[1,2,3,5,6,7,8,8a-octahydro-3,5-dihydroxy-2, 6-dimethyl-8-(2-methyl-butyryloxy)-naphthalen-1-yl]-hepta noi c acid delta-lactone, respectively. The inhibitory effects of the two derivatives on the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase were similar to that of mevinolin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biotransformation
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / chemistry*
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / isolation & purification
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / pharmacology
  • Lovastatin / analogs & derivatives*
  • Lovastatin / chemistry*
  • Lovastatin / isolation & purification
  • Lovastatin / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
  • dihydroxy-7-(1,2,3,5,6,7,8,8a-octahydro-3,5-dihydroxy-2,6-dimethyl-8-(2-methylbutyryloxy)naphthalen-1-yl)heptanoic acid lactone
  • dihydroxy-7-(1,2-dihydro-2-hydroxymethyl-6-methylnaphthalen-1-yl)heptanoic acid
  • Lovastatin