Tripartilactam, a Cyclobutane-Bearing Tricyclic Lactam from a Streptomyces sp. in a Dung Beetle’s Brood Ball

Tripartilactam, a structurally unprecedented cyclobutane-bearing tricyclic lactam metabolite, was discovered from Streptomyces sp. isolated from a brood ball of the dung beetle, Copris tripartitus. The structure of this compound was elucidated by the combination of NMR, MS, UV, and IR spectroscopy a...

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Bibliographic Details
Published in:Organic letters 2012-03, Vol.14 (5), p.1258-1261
Main Authors: Park, Seon-Hui, Moon, Kyuho, Bang, Hea-Son, Kim, Seong-Hwan, Kim, Dong-Gyu, Oh, Ki-Bong, Shin, Jongheon, Oh, Dong-Chan
Format: Article
Language:English
Subjects:
Animals
Cell Line, Tumor
Cell Survival - drug effects
Coleoptera - microbiology
Cyclobutanes - chemistry
Cyclobutanes - isolation & purification
Cyclobutanes - pharmacology
Feces - microbiology
Humans
Lactams - chemistry
Lactams - isolation & purification
Lactams - pharmacology
Molecular Structure
Sodium Potassium Chloride Symporter Inhibitors - chemistry
Sodium Potassium Chloride Symporter Inhibitors - isolation & purification
Sodium Potassium Chloride Symporter Inhibitors - pharmacology
Streptomyces - chemistry
Streptomyces - isolation & purification
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Summary:Tripartilactam, a structurally unprecedented cyclobutane-bearing tricyclic lactam metabolite, was discovered from Streptomyces sp. isolated from a brood ball of the dung beetle, Copris tripartitus. The structure of this compound was elucidated by the combination of NMR, MS, UV, and IR spectroscopy and multistep chemical derivatization. Tripartilactam was evaluated as a Na+/K+ ATPase inhibitor (IC50 = 16.6 μg/mL).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300108z