Targeted Discovery of an Enediyne-Derived Cycloaromatized Compound, Jejucarboside A, from a Marine Actinomycete

Im, Ji Hyeon; Shin, Daniel; Ban, Yeon Hee; Byun, Woong Sub; Bae, Eun Seo; Lee, Donghoon; Du, Young Eun; Cui, Jinsheng; Kwon, Yun; Nam, Sang-Jip; Cha, Sangwon; Lee, Sang Kook; Yoon, Yeo Joon; Oh, Dong-Chan

doi:10.1021/acs.orglett.2c02934

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Targeted Discovery of an Enediyne-Derived Cycloaromatized Compound, Jejucarboside A, from a Marine Actinomycete

Im, Ji Hyeon;
Shin, Daniel;
Ban, Yeon Hee;
Byun, Woong Sub;
Bae, Eun Seo;
... Cha, Sangwon;
외 8명

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초록

A genomic and spectroscopic signature-based search revealed a cycloaromatized enediyne, jejucarboside A (1), from a marine actinomycete strain. The structure of 1 was determined as a new cyclopenta[a]indene glycoside bearing carbonate functionality by nuclear magnetic resonance, high-resolution mass spectrometry (MS), MS/MS, infrared spectroscopy, and a modified Mosher's method. An iterative enediyne synthase pathway has been proposed for the putative biosynthesis of 1 by genomic analysis. Jejucarboside A exhibited cytotoxicity against the HCT116 colon carcinoma cells. © 2022 American Chemical Society. All rights reserved.

키워드

Enediynes; Glycosides; Indenes; Enediyne; Glycoside; Indene Derivative; Actinobacteria; Chemical Structure; Chemistry; Tandem Mass Spectrometry; Enediynes; Glycosides; Indenes; Molecular Structure; Tandem Mass Spectrometry

제목: Targeted Discovery of an Enediyne-Derived Cycloaromatized Compound, Jejucarboside A, from a Marine Actinomycete

저자: Im, Ji Hyeon; Shin, Daniel; Ban, Yeon Hee; Byun, Woong Sub; Bae, Eun Seo; Lee, Donghoon; Du, Young Eun; Cui, Jinsheng; Kwon, Yun; Nam, Sang-Jip; Cha, Sangwon; Lee, Sang Kook; Yoon, Yeo Joon; Oh, Dong-Chan

DOI: 10.1021/acs.orglett.2c02934

발행일: 2022-10

유형: Article

저널명: Organic Letters

권: 24

호: 39

페이지: 7188 ~ 7193