Angucyclines and Angucyclinones from Streptomyces sp. CB01913 Featuring C-Ring Cleavage and Expansion

Journal of Natural Products
Ming MaBen Shen

Abstract

Angucyclines and angucyclinones are aromatic polyketides with a tetracyclic benz[a]anthracene skeleton. The benz[a]anthracene scaffold is biosynthesized by type II polyketide synthases that catalyze the decarboxylative condensation of a short acyl-CoA starter and nine extender units. Angucyclines and angucyclinones, the largest group of polycyclic aromatic polyketides, achieve structural diversity via subsequent oxidation, ring cleavage, amino acid incorporation, and glycosylation. We here report the discovery of 14 angucyclinones and two angucyclines (1-16) from Streptomyces sp. CB01913, identifying 12 new compounds featuring various oxidations on rings A and C (1, 2, and 4), different sugar moieties attached to rings A and B (3 and 6), and C-ring cleavage (5 and 10-14) and expansion (8). These new structural features, highlighted by C-ring cleavage and expansion, enrich the structural diversity of angucyclines and angucyclinones. All compounds were tested for cytotoxicity and antibacterial activities, with 1, 5, 15, and 16 showing moderate activities against selected cancer cell lines or bacterial strains.

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Citations

Aug 11, 2016·The Journal of Antibiotics·Ming MaBen Shen
Oct 13, 2016·The Journal of Antibiotics·Zhikai GuoBen Shen
Jan 12, 2017·The Journal of Antibiotics· YixizhuomaMasami Ishibashi
Jan 19, 2019·Angewandte Chemie·Changsheng WuGilles P van Wezel
Nov 22, 2019·Journal of Zhejiang University. Science. B·Zi-Yue LiYong-Quan Li
Mar 5, 2016·Chemical & Pharmaceutical Bulletin·Mohamed S AbdelfattahMasami Ishibashi
Jun 14, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Natalia QuiñonesMauricio A Cuellar
Jan 20, 2021·Angewandte Chemie·Mingming CaoBen Shen
Jan 23, 2021·Natural Product Reports·Andrey A MikhaylovPavel N Solyev
Feb 23, 2018·Journal of Natural Products·Jian-Jun ChenBen Shen

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