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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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2010-11, Vol.73 (11), p.1943-1946
Hauptverfasser:	Igarashi, Yasuhiro, Yu, Linkai, Miyanaga, Satoshi, Fukuda, Takao, Saitoh, Noriko, Sakurai, Hiroaki, Saiki, Ikuo, Alonso-Vega, Pablo, Trujillo, Martha E
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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