Abstract
Manumycin (1), produced by Streptomyces parvulus (strain Tü 64), was isolated from the mycelium by extraction with acetone and could easily be purified chromatographically. Chemical degradation of 1 (C81H38N2O7) gave 2-acetamino-3-hydroxycyclopent-2-enone (2) by acetolysis, 2, 4, 6-trimethyl-2, 4-decadienoic acid (3) by alkaline hydrolysis, and 2-(2, 4, 6-trimethyl-2, 4-decadienoylamino)-5, 6-epoxy-l, 4-benzoquinone (5) by mild chromic acid oxidation. In connection with a detailed spectroscopic analysis, the structure of 1 could be elucidated and the (E)-configuration of the double bonds in the triene and diene chain was established. Manumycin exhibits biological activity against Gram-positive bacteria and fungi and furthermore, an inhibition of the developmental processes of some insects.
