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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 <i>Streptomyces</i> 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 <i>Streptomyces</i> sp. KCB-132, cultivated in liquid ISP2 medium, had led to the discovery of three C-ring cleavage angucyclinone <i>N</i>-heterocycles, pratensilins A-C, with a novel spiro indolinone-naphthofuran skeleton. Addition of 50 μM LaCl<sub>3</sub> to the same medium and subsequent chemical analysis of this strain returned a new member of this rare class, pratensilin D (<b>1</b>), along with two new angucyclinone derivatives, featuring ether-  ...[more]

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