New cineromycins and musacins obtained by metabolite pattern analysis of Streptomyces griseoviridis (FH-S 1832). II. Structure elucidation

J Antibiot (Tokyo). 1996 May;49(5):438-46. doi: 10.7164/antibiotics.49.438.

Abstract

A detailed analysis of the secondary metabolite pattern produced by Streptomyces griseoviridis (strain FH-S 1832) using a chemical screening method resulted in the detection, isolation and structure elucidation of new 14-membered lactones of the cineromycin B-type [dehydrocineromycin B (5), oxycineromycin B (7), and 2,3-dihydrocineromycin B (8)], as well as new gamma-lactones related to nigrosporalactone and 4,5-dihydroxy-octa-2,6-dienoic acid esters named musacins A to F (10, 13 approximately 15, 17, 18 and 21). The constitution of these metabolites were deduced from spectroscopic data as well as chemical transformations. The configuration of musacin D (10) was determined by derivatization with chiral acids (Helmchen's method).

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fermentation
  • Lactones / chemistry*
  • Lactones / isolation & purification*
  • Molecular Structure
  • Streptomyces / metabolism*
  • Structure-Activity Relationship

Substances

  • Lactones