Absolute Configuration and Antibiotic Activity of Piceamycin
- 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
- AMER CHEMICAL SOC
- JOURNAL OF NATURAL PRODUCTS, v.83, no.2, pp.277 - 285
- Journal Title
- JOURNAL OF NATURAL PRODUCTS
- Start Page
- End Page
- 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.
- Files in This Item
- There are no files associated with this item.
- Appears in
- ETC > Journal Articles
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.