The new bioactive diterpenes cyanthiwigins E-AA from the Jamaican sponge Myrmekioderma styx

The new bioactive diterpenes cyanthiwigins E-AA from the Jamaican sponge Myrmekioderma styx
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DOI:
10.1016/s0040-4020(02)00937-7
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发表时间:
2002-09-23
期刊:
影响因子:
2.1
通讯作者:
Hamann, MT
Hamann, MT
中科院分区:
化学3区
文献类型:
--
作者:
Peng, JN;Walsh, K;Hamann, MT

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从牙买加海绵Myrmekiandristyx中分离得到27个二萜化合物,命名为canthiwigins A-AA(1-27)。Cyanthiwigins E-AA(5-27)是一个未见报道的天然产物,其结构经H-1,C-13,DEPT,COSY,NOESY,HMQC和HMBC核磁共振谱分析确证。蓝蓟素是5,6,7-三碳环二萜,其中环戊烯酮的β-烯碳的化学位移在195 ppm的低场共振。测定了蓝蝶菌素A(1)、B(2)、C(3)和D(4)对乙型肝炎病毒(HBV)、人类免疫缺陷病毒(HIV-1)和结核分枝杆菌(Mtb)的抗作用。Cyanthiwigin C(3)显示出抗HBV和Mtb的活性,EC 50分别为43 μ g/mL和6.25 μ g/mL时的50%抑制。Cyanthiwigin B(2)显示出抗HIV-1的活性,EC 50为42.1 μ M。矢车菊素A、C-F、I和Z(1、3-6、10、26)对人原代肿瘤细胞有活性(IC 50
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 H-1, C-13, DEPT, COSY, NOESY, HMQC and HMBC NMR spectra. Cyanthiwigins are 5,6,7-tricarbocyclic diterpenes, in which the chemical shift of the beta-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 EC50 of 43 mug/mL and 50% inhibition at 6.25 mug/mL, respectively. Cyanthiwigin B (2) exhibited activity against HIV-1 with an EC50 of 42.1 muM. Cyanthiwigins A, C-F, I and Z (1, 3-6, 10, 26) are active against human primary tumor cells (IC50