Dumulmycin, an antitubercular bicyclic macrolide from a riverine sediment-derived streptomyces sp.

Joon Soo An; Bora Shin; Tae Ho Kim; Sunghoon Hwang; Yern Hyerk Shin; Jinsheng Cui; Young Eun Du; Jungwoo Yi; Sang Jip Nam; Suckchang Hong; Jongheon Shin; Jichan Jang; Yeo Joon Yoon; Dong Chan Oh

doi:10.1021/acs.orglett.1c00847

Dumulmycin, an antitubercular bicyclic macrolide from a riverine sediment-derived streptomyces sp.

Joon Soo An, Bora Shin, Tae Ho Kim, Sunghoon Hwang, Yern Hyerk Shin, Jinsheng Cui, Young Eun Du, Jungwoo Yi, Sang Jip Nam, Suckchang Hong, Jongheon Shin, Jichan Jang, Yeo Joon Yoon, Dong Chan Oh

Department of Chemistry & Nanoscience

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

22 Scopus citations

Abstract

Dumulmycin (1) was isolated from Streptomyces sp. DM28, a bacterial strain from a riverine sediment sample. The structure of 1 was elucidated as a bicyclic macrolide possessing 19-membered and 5-membered rings by spectroscopic analysis. The stereochemistry of 1 was determined by J-based configuration analysis, ROESY NMR data, DP4 calculations, and the modified Mosher's method. Genetic analysis identified a trans-acyltransferase polyketide biosynthetic gene cluster for 1. Dumulmycin exhibited in vitro antitubercular activity (MIC50 = 27.1 μM).

Original language	English
Pages (from-to)	3359-3363
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.1c00847
State	Published - 7 May 2021

Bibliographical note

Funding Information:
We are thankful to William R. Jacobs, Jr. (Albert Einstein College of Medicine) for the gift of the Mycobacterium tuberculosis mc2 6320 strain. This work was supported by National Research Foundation of Korea Grants funded by the Korean Government (Ministry of Science and ICT) (Nos. 2020R1A2C2003518 and 2021R1A4A2001251).

Funding Information:
We are thankful to William R. Jacobs, Jr. (Albert Einstein College of Medicine) for the gift of the Mycobacterium tuberculosis mc 6320 strain. This work was supported by National Research Foundation of Korea Grants funded by the Korean Government (Ministry of Science and ICT) (Nos. 2020R1A2C2003518 and 2021R1A4A2001251). 2

Publisher Copyright:
© 2021 American Chemical Society.

Access to Document

10.1021/acs.orglett.1c00847

Cite this

@article{c10694060848400d997111da16e8c00f,

title = "Dumulmycin, an antitubercular bicyclic macrolide from a riverine sediment-derived streptomyces sp.",

abstract = "Dumulmycin (1) was isolated from Streptomyces sp. DM28, a bacterial strain from a riverine sediment sample. The structure of 1 was elucidated as a bicyclic macrolide possessing 19-membered and 5-membered rings by spectroscopic analysis. The stereochemistry of 1 was determined by J-based configuration analysis, ROESY NMR data, DP4 calculations, and the modified Mosher's method. Genetic analysis identified a trans-acyltransferase polyketide biosynthetic gene cluster for 1. Dumulmycin exhibited in vitro antitubercular activity (MIC50 = 27.1 μM).",

author = "An, {Joon Soo} and Bora Shin and Kim, {Tae Ho} and Sunghoon Hwang and Shin, {Yern Hyerk} and Jinsheng Cui and Du, {Young Eun} and Jungwoo Yi and Nam, {Sang Jip} and Suckchang Hong and Jongheon Shin and Jichan Jang and Yoon, {Yeo Joon} and Oh, {Dong Chan}",

note = "Funding Information: We are thankful to William R. Jacobs, Jr. (Albert Einstein College of Medicine) for the gift of the Mycobacterium tuberculosis mc2 6320 strain. This work was supported by National Research Foundation of Korea Grants funded by the Korean Government (Ministry of Science and ICT) (Nos. 2020R1A2C2003518 and 2021R1A4A2001251). Funding Information: We are thankful to William R. Jacobs, Jr. (Albert Einstein College of Medicine) for the gift of the Mycobacterium tuberculosis mc 6320 strain. This work was supported by National Research Foundation of Korea Grants funded by the Korean Government (Ministry of Science and ICT) (Nos. 2020R1A2C2003518 and 2021R1A4A2001251). 2 Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = may,

day = "7",

doi = "10.1021/acs.orglett.1c00847",

language = "English",

volume = "23",

pages = "3359--3363",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Dumulmycin, an antitubercular bicyclic macrolide from a riverine sediment-derived streptomyces sp.

AU - An, Joon Soo

AU - Shin, Bora

AU - Kim, Tae Ho

AU - Hwang, Sunghoon

AU - Shin, Yern Hyerk

AU - Cui, Jinsheng

AU - Du, Young Eun

AU - Yi, Jungwoo

AU - Nam, Sang Jip

AU - Hong, Suckchang

AU - Shin, Jongheon

AU - Jang, Jichan

AU - Yoon, Yeo Joon

AU - Oh, Dong Chan

N1 - Funding Information: We are thankful to William R. Jacobs, Jr. (Albert Einstein College of Medicine) for the gift of the Mycobacterium tuberculosis mc2 6320 strain. This work was supported by National Research Foundation of Korea Grants funded by the Korean Government (Ministry of Science and ICT) (Nos. 2020R1A2C2003518 and 2021R1A4A2001251). Funding Information: We are thankful to William R. Jacobs, Jr. (Albert Einstein College of Medicine) for the gift of the Mycobacterium tuberculosis mc 6320 strain. This work was supported by National Research Foundation of Korea Grants funded by the Korean Government (Ministry of Science and ICT) (Nos. 2020R1A2C2003518 and 2021R1A4A2001251). 2 Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/5/7

Y1 - 2021/5/7

N2 - Dumulmycin (1) was isolated from Streptomyces sp. DM28, a bacterial strain from a riverine sediment sample. The structure of 1 was elucidated as a bicyclic macrolide possessing 19-membered and 5-membered rings by spectroscopic analysis. The stereochemistry of 1 was determined by J-based configuration analysis, ROESY NMR data, DP4 calculations, and the modified Mosher's method. Genetic analysis identified a trans-acyltransferase polyketide biosynthetic gene cluster for 1. Dumulmycin exhibited in vitro antitubercular activity (MIC50 = 27.1 μM).

AB - Dumulmycin (1) was isolated from Streptomyces sp. DM28, a bacterial strain from a riverine sediment sample. The structure of 1 was elucidated as a bicyclic macrolide possessing 19-membered and 5-membered rings by spectroscopic analysis. The stereochemistry of 1 was determined by J-based configuration analysis, ROESY NMR data, DP4 calculations, and the modified Mosher's method. Genetic analysis identified a trans-acyltransferase polyketide biosynthetic gene cluster for 1. Dumulmycin exhibited in vitro antitubercular activity (MIC50 = 27.1 μM).

UR - http://www.scopus.com/inward/record.url?scp=85106162085&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c00847

DO - 10.1021/acs.orglett.1c00847

M3 - Article

C2 - 33885319

AN - SCOPUS:85106162085

SN - 1523-7060

VL - 23

SP - 3359

EP - 3363

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Dumulmycin, an antitubercular bicyclic macrolide from a riverine sediment-derived streptomyces sp.

Abstract

Bibliographical note

Access to Document

Fingerprint

Cite this