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Bombyxamycins A and B, Cytotoxic Macrocyclic Lactams from an Intestinal Bacterium of the Silkworm Bombyx mori

Author:
Shin, Yern-Hyerk, Beom, Ji Yoon, Chung, Beomkoo, Shin, Yoonho, Byun, Woong Sub, Moon, Kyuho, Bae, Munhyung, Lee, Sang Kook, Oh, Ki-Bong, Shin, Jongheon, Yoon, Yeo Joon, Oh, Dong-Chan
Source:
Organic letters 2019 v.21 no.6 pp. 1804-1808
ISSN:
1523-7052
Subject:
Bombyx mori, Streptomyces, bacteria, biosynthesis, chemical structure, cytochrome P-450, cytotoxicity, derivatization, digestive system, gene deletion, genetic analysis, lactams, multigene family, silkworms, spectral analysis, tetrahydrofuran
Abstract:
Bombyxamycins A and B (1 and 2) were discovered from a silkworm gut Streptomyces bacterium. Spectroscopic analysis and multiple-step chemical derivatization identified them as 26-membered cyclic lactams with polyene features. Bombyxamycin A showed significant antibacterial and antiproliferative effects. The bombyxamycin biosynthetic gene cluster was identified by genetic analysis. Gene deletion experiments confirmed that the cytochrome P450 BomK is responsible for the generation of 2, which unprecedentedly bears tetrahydrofuran in its macrocyclic ring.
Agid:
6326826