RRC ID 70235
Author Shin YH, Kang S, Byun WS, Jeon CW, Chung B, Beom JY, Hong S, Lee J, Shin J, Kwak YS, Lee SK, Oh KB, Yoon YJ, Oh DC.
Title Absolute Configuration and Antibiotic Activity of Piceamycin.
Journal J Nat Prod
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.
Volume 83(2)
Pages 277-285
Published 2020-2-28
DOI 10.1021/acs.jnatprod.9b00678
PMID 32073848
MeSH Anti-Bacterial Agents / chemistry Anti-Bacterial Agents / pharmacology* Biological Products / chemistry* Biological Products / metabolism Biosynthetic Pathways Humans Lactams, Macrocyclic / chemistry* Microbial Sensitivity Tests Molecular Structure Proteus / chemistry Stereoisomerism Streptomyces / chemistry*
IF 3.782
Pathogenic eukaryotic microorganisms Trichophyton mentagrophytes IFM 40996