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

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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.

Original languageEnglish
Pages (from-to)7188-7193
Number of pages6
JournalOrganic Letters
Volume24
Issue number39
DOIs
StatePublished - 7 Oct 2022

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea grants funded by the Republic of Korean Government (Ministry of Science and ICT) (2021R1A4A2001251, 2022R1A2C3004621, and 2020R1A2C2003518).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

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