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Antibacterial and Cytotoxic Bridged and Ring Cleavage Angucyclinones From a Marine Streptomyces sp.

ABSTRACT: Chemical investigation of a marine-derived Streptomyces sp. KCB-132, cultivated in liquid ISP2 medium, had led to the discovery of three C-ring cleavage angucyclinone N-heterocycles, pratensilins A-C, with a novel spiro indolinone-naphthofuran skeleton. Addition of 50 ?M LaCl3 to the same medium and subsequent chemical analysis of this strain returned a new member of this rare class, pratensilin D (1), along with two new angucyclinone derivatives, featuring ether-bridged (2) and A-ring cleavage (3) structural properties. Their structures and absolute configurations were assigned by spectroscopic analysis, single-crystal X-ray diffractions, and equivalent circulating density (ECD) calculations. (+)- and (-)-1, a pair of enantiomeric nitrogen-containing angucyclinones, exhibited different strengths of antibacterial and cytotoxic activities.

SUBMITTER: Guo L

PROVIDER: S-EPMC7417440 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Antibacterial and Cytotoxic Bridged and Ring Cleavage Angucyclinones From a Marine Streptomyces sp.

Guo Lin L Zhang Lu L Yang Qiaoli Q Xu Bo B Fu Xinzhen X Liu Ming M Li Zhi Z Zhang Shumin S Xie Zeping Z

Frontiers in chemistry 20200804

Chemical investigation of a marine-derived Streptomyces sp. KCB-132, cultivated in liquid ISP2 medium, had led to the discovery of three C-ring cleavage angucyclinone N-heterocycles, pratensilins A-C, with a novel spiro indolinone-naphthofuran skeleton. Addition of 50 μM LaCl3 to the same medium and subsequent chemical analysis of this strain returned a new member of this rare class, pratensilin D (1), along with two new angucyclinone derivatives, featuring ether- ...[more]

PMID: 32850626

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