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

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2022-07, Vol.85 (7), p.1867-1871
• Main Authors: Tatsukawa, Ayaka, Tanaka, Yu, Nagano, Haruka, Fukumoto, Atsushi, Anzai, Yojiro, Arakawa, Kenji
• Format: Article
• Language: English
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.2c00131

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 l-serine (C-1 to C-3). The nitrogen atom attached at C-2 (Nα) originates from serine, whereas the nitrogen atom of a hexen-1-yl amine unit (Nβ) is derived from glutamic acid. The quorum-sensing inhibitory activity of maniwamycin G was 2-fold lower than that of maniwamycin F.