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Absolute Configuration and Antibiotic Activity of Piceamycin.
- Source :
-
Journal of natural products [J Nat Prod] 2020 Feb 28; Vol. 83 (2), pp. 277-285. Date of Electronic Publication: 2020 Feb 19. - Publication Year :
- 2020
-
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.
- Subjects :
- Anti-Bacterial Agents chemistry
Biological Products metabolism
Biosynthetic Pathways
Humans
Microbial Sensitivity Tests
Molecular Structure
Proteus chemistry
Stereoisomerism
Anti-Bacterial Agents pharmacology
Biological Products chemistry
Lactams, Macrocyclic chemistry
Streptomyces chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 83
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 32073848
- Full Text :
- https://doi.org/10.1021/acs.jnatprod.9b00678