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

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

Seoul National University
Kangwon National University
Dongguk University
Kyungpook National University
Ewha Womans University

Research output: Contribution to journal › Article › peer-review

18 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 language	English
Pages (from-to)	7188-7193
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	39
DOIs	https://doi.org/10.1021/acs.orglett.2c02934
State	Published - 7 Oct 2022

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10.1021/acs.orglett.2c02934

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

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.",

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doi = "10.1021/acs.orglett.2c02934",

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AU - Im, Ji Hyeon

AU - Shin, Daniel

AU - Ban, Yeon Hee

AU - Byun, Woong Sub

AU - Bae, Eun Seo

AU - Lee, Donghoon

AU - Du, Young Eun

AU - Cui, Jinsheng

AU - Kwon, Yun

AU - Nam, Sang Jip

AU - Cha, Sangwon

AU - Lee, Sang Kook

AU - Yoon, Yeo Joon

AU - Oh, Dong Chan

PY - 2022/10/7

Y1 - 2022/10/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85139178947

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SN - 1523-7060

VL - 24

SP - 7188

EP - 7193

JO - Organic Letters

JF - Organic Letters

IS - 39

ER -

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

Abstract

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