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

• Published in: Organic letters Vol. 14; no. 5; pp. 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: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.03.2012; Amer Chemical Soc
• Subjects: Animals; Cell Line, Tumor; Cell Survival - drug effects; Chemistry; Chemistry, Organic; Coleoptera - microbiology; Cyclobutanes - chemistry; Cyclobutanes - isolation & purification; Cyclobutanes - pharmacology; Feces - microbiology; Humans; Lactams - chemistry; Lactams - isolation & purification; Lactams - pharmacology; Molecular Structure; Physical Sciences; Science & Technology; Sodium Potassium Chloride Symporter Inhibitors - chemistry; Sodium Potassium Chloride Symporter Inhibitors - isolation & purification; Sodium Potassium Chloride Symporter Inhibitors - pharmacology; Streptomyces - chemistry; Streptomyces - isolation & purification; FUNGUS; ABSOLUTE-CONFIGURATION; ANT; CARBOXYLIC-ACIDS
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol300108z

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).