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

Organic Letters
Yern-Hyerk ShinDong-Chan Oh

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.

References

Jan 27, 2007·Journal of Natural Products·Philip G WilliamsWilliam Fenical
Oct 4, 2008·Science·Jarrod J ScottCameron R Currie
Jan 6, 2009·Insect Biochemistry and Molecular Biology·UNKNOWN International Silkworm Genome Consortium
Mar 31, 2009·Nature Chemical Biology·Dong-Chan OhJon Clardy
Jun 16, 2010·Proceedings of the National Academy of Sciences of the United States of America·Joshua A V BlodgettJon Clardy
Jun 26, 2013·Chemistry & Biology·Sanjay B HariDustin J Maly
Sep 9, 2015·ACS Chemical Biology·Silke Alt, Barrie Wilkinson
Dec 15, 2015·Applied Microbiology and Biotechnology·Aileen BerasateguiMartin Kaltenpoth
Sep 28, 2016·Current Biology : CB·Antonio C Ruzzini, Jon Clardy
Jan 21, 2017·Cell Chemical Biology·Yongqi ShaoWilhelm Boland

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