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

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

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 ma...

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Veröffentlicht in:Organic letters 2022-10, Vol.24 (39), p.7188-7193
Hauptverfasser: 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
Format: Artikel
Sprache:eng
Schlagworte:
Actinobacteria - chemistry
Enediynes - chemistry
Glycosides - chemistry
Indenes - chemistry
Molecular Structure
Tandem Mass Spectrometry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02934