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Title 

Antibacterial cyclic lipopeptide enamidonins with an enamide-linked acyl chain from a Streptomyces species

 

항균활성 환형 리포펩타이드 에나미돈

Authors 

Sangkeun SonSung-Kyun KoSeung Min KimEun KimGil Su KimByeongsan LeeIn Ja RyooWon Gon KimJung-Sook LeeYoung-Soo HongJae-Hyuk JangJong Seog Ahn

Publisher 

American Chemical Society

Issue Date 

2018

Citation 

Journal of Natural Products

Abstract 

Three cyclic lipopeptides, including one known (1) and two new (2 and 3) compounds, that possess the rare enamide linkage group were discovered from Streptomyces sp. KCB14A132, an actinobacterium isolated from a soil sample collected from Jeung Island, Korea. The NMR and MS-based characterization showed that they differed in the amino acid residues in the peptide backbone. Application of Marfey's analysis, GITC derivatization, and modified Mosher's method, as well as ECD measurements provided the absolute configurations of enamidonin (1) and those of new compounds enamidonins B and C (2 and 3). The two new enamidonin analogues were shown to exhibit antibacterial activity against Gram-positive bacteria including methicillin-resistant and quinolone-resistant Staphylococcus aureus. Furthermore, evaluation of the extraction conditions and a close inspection of the LC-MS chromatograms revealed that the N, N-acetonide unit of the enamidonin family was formed during the acetone extraction process. The chemically prepared deacetonide derivatives of enamidonins were found to lack antibacterial activity, demonstrating that the dimethylimidazolidinone residue is necessary for antibacterial activity.

ISSN 

0163-3864

Link 

http://dx.doi.org/10.1021/acs.jnatprod.8b00497

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2019-05-02


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