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자연과학대학
화학·나노과학전공
Journal papers
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Absolute Configuration and Antibiotic Activity of Piceamycin
Title
Absolute Configuration and Antibiotic Activity of Piceamycin
Authors
Shin Y.-H.
;
Kang S.
;
Byun W.S.
;
Jeon C.-W.
;
Chung B.
;
Beom J.Y.
;
Hong S.
;
Lee J.
;
Shin J.
;
Kwak Y.-S.
;
Lee S.K.
;
Oh K.-B.
;
Yoon Y.J.
;
Oh D.-C.
Ewha Authors
윤여준
SCOPUS Author ID
윤여준
Issue Date
2020
Journal Title
Journal of Natural Products
ISSN
0163-3864
Citation
Journal of Natural Products vol. 83, no. 2, pp. 277 - 285
Publisher
American Chemical Society
Indexed
SCIE; SCOPUS
Document Type
Article
Abstract
The cultivation of a Streptomyces sp. SD53 strain isolated from the gut of the silkworm Bombyx mori produced two macrolactam natural products, piceamycin (1) and bombyxamycin C (2). The planar structures of 1 and 2 were identified by a combination of NMR, MS, and UV spectroscopic analyses. The absolute configurations were assigned based on chemical and chromatographic methods as well as ECD calculations. A new chromatography-based experimental method for determining the configurations of stereogenic centers β to nitrogen atoms in macrolactams was established and successfully applied in this report. These compounds exhibited significant bioactivities against the silkworm entomopathogen Bacillus thuringiensis and various human pathogens as well as human cancer cell lines. In particular, piceamycin potently inhibited Salmonella enterica and Proteus hauseri with MIC values of 0.083 μg/mL and 0.025 μg/mL, respectively. The biosynthetic pathway involved in the formation of the cyclopentenone moiety in piceamycin is discussed. Copyright © 2020 American Chemical Society and American Society of Pharmacognosy.
DOI
10.1021/acs.jnatprod.9b00678
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