The structure of manumycin. I. Characterization, structure elucidation and biological activity

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 (C31H38N2O7) 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-1,4-benzoquinon e (5) by 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.