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Absolute Configuration and Antibiotic Activity of Piceamycin

Cited 16 time in Web of Science Cited 22 time in Scopus

Shin, Yern-Hyerk; Kang, Saeyeon; Byun, Woong Sub; Jeon, Chang-Wook; Chung, Beomkoo; Beom, Ji Yoon; Hong, Suckchang; Lee, Jeeyeon; Shin, Jongheon; Kwak, Youn-Sig; Lee, Sang Kook; Oh, Ki-Bong; Yoon, Yeo Joon; Oh, Dong-Chan

Issue Date
American Chemical Society
Journal of Natural Products, Vol.83 No.2, pp.277-285
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 beta 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 mu g/mL and 0.025 mu g/mL, respectively. The biosynthetic pathway involved in the formation of the cyclopentenone moiety in piceamycin is discussed.
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Related Researcher

  • College of Pharmacy
  • Department of Manufacturing Pharmacy
Research Area Development of methodologies using metal catalyst, Total synthesis of natural products


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