Sarsolenane and Capnosane Diterpenes from the Hainan Soft Coral Sarcophyton trocheliophorum Marenzeller as PTP1B Inhibitors

• Published in: European journal of organic chemistry Vol. 2014; no. 9; pp. 1841 - 1847
• Main Authors: Liang, Lin-Fu, Kurtán, Tibor, Mándi, Attila, Gao, Li-Xin, Li, Jia, Zhang, Wen, Guo, Yue-Wei
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.03.2014; WILEY‐VCH Verlag; Wiley
• Subjects: Chemistry; Chemistry, Organic; Configuration determination; Drug discovery; Natural products; Physical Sciences; Science & Technology; Structure elucidation; Terpenoids; CEMBRANOIDS; Natural products; Terpenoids; Configuration determination; CHEMISTRY; Drug discovery; Structure elucidation; DISCOVERY; TOBACCO
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201301683

Two new sarsolenane diterpenes, dihydrosarsolenone (2), methyl dihydrosarsolenoneate (3), and two new capnosane diterpenes, sarsolilides B (5) and C (6), were isolated together with the known analogue, sarsolilide A (4), from the Hainan soft coral Sarcophyton trocheliophorum Marenzeller. Their structures were elucidated by detailed spectroscopic analysis and by comparison with reported data, leading to a structure revision of sarsolenone (1). The absolute configurations of 2 and 5 were determined by TDDFT ECD calculations, and they could be used as ECD reference compounds in the determination of the absolute configuration of their related derivatives. Compounds 4 and 5 exhibited inhibitory activity in vitro against protein tyrosine phosphatases 1B (PTP1B), representing the first report of PTP1B inhibitory activity for capnosane diterpenes. Sarsolenane diterpenes 2 and 3 and capnosane diterpenes 5 and 6 were isolated from the Hainan soft coral S. trocheliophorum. The absolute configurations of 2 and 5 were determined by TDDFD ECD calculations, affording the configurational assignment of other analogues by ECD comparison or by biogenetic correlations. Compound 4 showed PTP1B inhibitory activity with IC50 values of 6.8 μM.