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

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

doi:10.1021/acs.orglett.2c02934

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

Org Lett. 2022 Oct 7;24(39):7188-7193. doi: 10.1021/acs.orglett.2c02934. Epub 2022 Sep 27.

Authors

Affiliations

¹ Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.
² Department of Molecular Bioscience, College of Biomedical Science, Kangwon National University, Chuncheon 24341, Republic of Korea.
³ Department of Chemistry, Dongguk University, Seoul 04620, Republic of Korea.
⁴ Research Institute of Pharmaceutical Science, College of Pharmacy, Kyungpook National University, Daegu 41566, Republic of Korea.
⁵ Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Republic of Korea.

PMID: 36165456
DOI: 10.1021/acs.orglett.2c02934

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Actinobacteria* / chemistry
Enediynes / chemistry
Glycosides / chemistry
Indenes* / chemistry
Molecular Structure
Tandem Mass Spectrometry

Substances

Enediynes
Glycosides
Indenes