Abyssomicin I, a Modified Polycyclic Polyketide from Streptomyces sp. CHI39

Abyssomicin I (1), a new modified polycyclic polyketide, was isolated from the culture extract of a soil-derived Streptomyces sp. The structure of 1 was elucidated by interpretation of NMR and other spectroscopic data. The stereochemistry of the new compound was assigned by NOE analysis, chemical de...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2010-11, Vol.73 (11), p.1943-1946
Main Authors: Igarashi, Yasuhiro, Yu, Linkai, Miyanaga, Satoshi, Fukuda, Takao, Saitoh, Noriko, Sakurai, Hiroaki, Saiki, Ikuo, Alonso-Vega, Pablo, Trujillo, Martha E
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - isolation & purification
Anti-Bacterial Agents - pharmacology
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Applied microbiology
Bacillus subtilis - drug effects
Biological and medical sciences
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Bridged Bicyclo Compounds, Heterocyclic - isolation & purification
Bridged Bicyclo Compounds, Heterocyclic - pharmacology
Candida albicans - drug effects
Escherichia coli - drug effects
Fundamental and applied biological sciences. Psychology
General aspects
Gram-Positive Bacteria - drug effects
Inhibitory Concentration 50
Mexico
Microbial Sensitivity Tests
Microbiology
Micrococcus luteus - drug effects
Nuclear Magnetic Resonance, Biomolecular
Soil Microbiology
Staphylococcus aureus - drug effects
Streptomyces - chemistry
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Summary:Abyssomicin I (1), a new modified polycyclic polyketide, was isolated from the culture extract of a soil-derived Streptomyces sp. The structure of 1 was elucidated by interpretation of NMR and other spectroscopic data. The stereochemistry of the new compound was assigned by NOE analysis, chemical derivatization, and application of the modified Mosher method. While 1 was inactive against bacteria and yeasts, the oxidized derivative 7 showed weak activities against Gram-positive bacteria. Compounds 1 and 7 exhibited inhibitory effects on tumor cell invasion with IC50 values of 11 and 0.21 μM, respectively.
ISSN:0163-3864
1520-6025
DOI:10.1021/np100292h