Abstract
Twenty-seven diterpenes, cyanthiwigins A–AA ( 1– 27 ), were isolated from the Jamaican sponge Myrmekioderma styx. Cyanthiwigins E–AA ( 5– 27 ) are unreported natural products and their structures were elucidated by detailed analysis of 1H, 13C, DEPT, COSY, NOESY, HMQC and HMBC NMR spectra. Cyanthiwigins are 5,6,7-tricarbocyclic diterpenes, in which the chemical shift of the β-olefinic carbon of the cyclopentenone resonates at a low field of 195 ppm. Cyanthiwigins A ( 1 ), B ( 2 ), C ( 3 ) and D ( 4 ) were assayed against hepatitis B virus (HBV), human immunodeficiency virus (HIV-1), and Mycobacterium tuberculosis (Mtb). Cyanthiwigin C ( 3 ) exhibited activity against HBV and Mtb with an EC 50 of 43 μg/mL and 50% inhibition at 6.25 μg/mL, respectively. Cyanthiwigin B ( 2 ) exhibited activity against HIV-1 with an EC 50 of 42.1 μM. Cyanthiwigins A, C–F, I and Z ( 1 , 3– 6 , 10 , 26 ) are active against human primary tumor cells (IC 50<18 μM) with cyanthiwigin F exhibiting the strongest activity (IC 50 3.1 μM).
Published Version
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