Isolation, Biosynthetic Investigation, and Biological Evaluation of Maniwamycin G, an Azoxyalkene Compound from Streptomyces sp. TOHO-M025

A new maniwamycin analogue, maniwamycin G, was isolated from Streptomyces sp. TOHO-M025 as a major product. Maniwamycin G has a molecular formula of C12H22N2O4, and its extensive NMR analysis revealed that maniwamycin G contains a methoxycarbonyl group instead of an amide as found in maniwamycin F. Its C-2 and C-3 configurations were determined to be (2R, 3R) by circular dichroism spectrum and a modified Mosher method, respectively. The biosynthetic origin of maniwamycin G was investigated using isotope-labeled compounds. The carbon source of maniwamycin G is four acetate units (C-1 ', C-2 '; C-3 ', C-4 '; C-5 ', C-6 '; and C-4, C-5) and Lserine (C-1 to C-3). The nitrogen atom attached at C-2 (N alpha) originates from serine, whereas the nitrogen atom of a hexen-1-yl amine unit (N beta) is derived from glutamic acid. The quorum-sensing inhibitory activity of maniwamycin G was 2-fold lower than that of maniwamycin F.

Automated summary

A new maniwamycin analogue, named maniwamycin G, was isolated from Streptomyces sp. TOHO-M025. It contains a methoxycarbonyl group instead of an amide as found in maniwamycin F. The carbon source of maniwamycin G is four acetate units and L-serine, while the nitrogen sources are serine and glutamic acid.