Identification and antibacterial activity of a new oleandomycin derivative from streptomyces antibioticus

Beom Seok Kim; Hyuncheol Oh; Sun Young Kim; Jeong Ah Park; Yeo Joon Yoon; Sang Kil Lee; Bo Yeon Kim; Jong Seog Ahn

doi:10.1038/ja.2005.23

Identification and antibacterial activity of a new oleandomycin derivative from streptomyces antibioticus

Beom Seok Kim, Hyuncheol Oh, Sun Young Kim, Jeong Ah Park, Yeo Joon Yoon, Sang Kil Lee, Bo Yeon Kim, Jong Seog Ahn

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

1 Citation (Scopus)

Abstract

During the study on the oleandomycin production, we purified a new oleandomycin derivative having a macrolactone of which biosynthesis does not follow the genetic architecture of the oleandomycin PKS. The molecular formula for the compound was suggested as C₃₅H₅₉NO₁₁ on the basis of the analysis of NMR and HRMS data (m/z 670.4185, Δ-1.9 mmu, calcd for C₃₅H₆₀NO₁₁). ¹³C NMR assignments and analysis of COSY, HMBC and HMQC data suggested that the compound differs from oleandomycin by formation of the olefinic functionality resulting from the dehydration of a hydroxy group in oleandomycin. The new oleandomycin derivative has antibacterial activities similar to those of oleandomycin agaisnt Enterococcus faecalis, Bacillus subtilis and Staphylococcus aureus.

Original language	English
Pages (from-to)	196-201
Number of pages	6
Journal	Journal of Antibiotics
Volume	58
Issue number	3
DOIs	https://doi.org/10.1038/ja.2005.23
Publication status	Published - 2005 Mar
Externally published	Yes

Keywords

Dehydration of hydroxyl group
New oleandomycin derivative
Olefinic formation
Streptomyces antibioticus

ASJC Scopus subject areas

Pharmacology
Drug Discovery

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10.1038/ja.2005.23

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title = "Identification and antibacterial activity of a new oleandomycin derivative from streptomyces antibioticus",

abstract = "During the study on the oleandomycin production, we purified a new oleandomycin derivative having a macrolactone of which biosynthesis does not follow the genetic architecture of the oleandomycin PKS. The molecular formula for the compound was suggested as C35H59NO11 on the basis of the analysis of NMR and HRMS data (m/z 670.4185, Δ-1.9 mmu, calcd for C35H60NO11). 13C NMR assignments and analysis of COSY, HMBC and HMQC data suggested that the compound differs from oleandomycin by formation of the olefinic functionality resulting from the dehydration of a hydroxy group in oleandomycin. The new oleandomycin derivative has antibacterial activities similar to those of oleandomycin agaisnt Enterococcus faecalis, Bacillus subtilis and Staphylococcus aureus.",

keywords = "Dehydration of hydroxyl group, New oleandomycin derivative, Olefinic formation, Streptomyces antibioticus",

author = "Kim, {Beom Seok} and Hyuncheol Oh and Kim, {Sun Young} and Park, {Jeong Ah} and Yoon, {Yeo Joon} and Lee, {Sang Kil} and Kim, {Bo Yeon} and Ahn, {Jong Seog}",

year = "2005",

month = mar,

doi = "10.1038/ja.2005.23",

language = "English",

volume = "58",

pages = "196--201",

journal = "Journal of Antibiotics",

issn = "0021-8820",

publisher = "Japan Antibiotics Research Association",

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T1 - Identification and antibacterial activity of a new oleandomycin derivative from streptomyces antibioticus

AU - Kim, Beom Seok

AU - Oh, Hyuncheol

AU - Kim, Sun Young

AU - Park, Jeong Ah

AU - Yoon, Yeo Joon

AU - Lee, Sang Kil

AU - Kim, Bo Yeon

AU - Ahn, Jong Seog

PY - 2005/3

Y1 - 2005/3

N2 - During the study on the oleandomycin production, we purified a new oleandomycin derivative having a macrolactone of which biosynthesis does not follow the genetic architecture of the oleandomycin PKS. The molecular formula for the compound was suggested as C35H59NO11 on the basis of the analysis of NMR and HRMS data (m/z 670.4185, Δ-1.9 mmu, calcd for C35H60NO11). 13C NMR assignments and analysis of COSY, HMBC and HMQC data suggested that the compound differs from oleandomycin by formation of the olefinic functionality resulting from the dehydration of a hydroxy group in oleandomycin. The new oleandomycin derivative has antibacterial activities similar to those of oleandomycin agaisnt Enterococcus faecalis, Bacillus subtilis and Staphylococcus aureus.

AB - During the study on the oleandomycin production, we purified a new oleandomycin derivative having a macrolactone of which biosynthesis does not follow the genetic architecture of the oleandomycin PKS. The molecular formula for the compound was suggested as C35H59NO11 on the basis of the analysis of NMR and HRMS data (m/z 670.4185, Δ-1.9 mmu, calcd for C35H60NO11). 13C NMR assignments and analysis of COSY, HMBC and HMQC data suggested that the compound differs from oleandomycin by formation of the olefinic functionality resulting from the dehydration of a hydroxy group in oleandomycin. The new oleandomycin derivative has antibacterial activities similar to those of oleandomycin agaisnt Enterococcus faecalis, Bacillus subtilis and Staphylococcus aureus.

KW - Dehydration of hydroxyl group

KW - New oleandomycin derivative

KW - Olefinic formation

KW - Streptomyces antibioticus

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JO - Journal of Antibiotics

JF - Journal of Antibiotics

IS - 3

ER -

Identification and antibacterial activity of a new oleandomycin derivative from streptomyces antibioticus

Abstract

Keywords

ASJC Scopus subject areas

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