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Structurally Diverse Metabolites from the Soft Coral Sinularia verruca Collected in the South China Sea

Yuan, Weiping, Cheng, Shimiao, Fu, Weitao, Zhao, Min, Li, Xiubao, Cai, Yuepiao, Dong, Jianyong, Huang, Kexin, Gustafson, Kirk R., Yan, Pengcheng
Journal of natural products 2016 v.79 no.4 pp. 1124-1131
HIV infections, Human immunodeficiency virus 1, Sinularia, alkaloids, corals, cytopathogenicity, inhibitory concentration 50, median effective concentration, metabolites, nitric oxide, sesquiterpenoids, spectral analysis, South China Sea
Nineteen metabolites with diverse structures, including the rare pyrroloindoline alkaloid verrupyrroloindoline (1), the unprecedented highly fused benzosesquiterpenoid verrubenzospirolactone (2), the new asteriscane-type sesquiterpenoid 10-deoxocapillosanane D (3), and the two new cyclopentenone derivatives (4S*,5S*)-4-hydroxy-5-(hydroxymethyl)-2,3-dimethyl-4-pentylcyclopent-2-en-1-one (4) and (S)-4-hydroxy-5-methylene-2,3-dimethyl-4-pentylcyclopent-2-en-1-one (5), were isolated from a South China Sea collection of the soft coral Sinularia verruca. Eleven previously described marine metabolites (7–15, 18, and 19) were also obtained as well as three new EtOH-adduct artifacts (6, 16, and 17). The structures of the new compounds were elucidated by extensive spectroscopic analysis and by comparison with previously reported data. Compounds 4, 5, and 16 showed protection against the cytopathic effects of HIV-1 infection with EC₅₀ values of 5.8–34 μM, and 4, 6, and 16 exhibited inhibition against LPS-induced NO production with IC₅₀ values of 24–28 μM.