Isolation and Structure Elucidation of Vicenistatin M, and Importance of the Vicenisamine Aminosugar for Exerting Cytotoxicity of Vicenistatin

Abstract

A new analogue of Vicenistatin was isolated from the producing strain Streptomyces sp. HC-34. A characteristic of the elucidated structure involved the existence of a neutral sugar mycarose instead of an aminosugar vicenisamine of Vicenistatin. The absolute stereochemistry of the new analogue (named as Vicenistatin M) was determined by the synthesis of D-mycarose and of vicenistatin M itself. Biological testing of Vicenistatin M suggested the importance of vicenisamine for exerting the cytotoxicity of vicenistatin.