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Phenylspirodrimanes with Anti-HIV Activity from the Sponge-Derived Fungus Stachybotrys chartarum MXH-X73

Ma, Xinhua, Li, Letao, Zhu, Tianjiao, Ba, Mingyu, Li, Guoqiang, Gu, Qianqun, Guo, Ying, Li, Dehai
Journal of natural products 2013 v.76 no.12 pp. 2298-2306
Human immunodeficiency virus 1, RNA-directed DNA polymerase, Stachybotrys chartarum, antiretroviral properties, fungi, hydrolysis, median effective concentration, spectral analysis, virus replication
Seven new phenylspirodrimanes, named stachybotrins D–F (1, 3, 4), stachybocins E and F (5, 6), and stachybosides A and B (7, 8), and four known compounds (2, 9–11), were isolated from the sponge-derived fungus Stachybotrys chartarum MXH-X73. Their structures were determined by detailed analysis of spectroscopic data. The absolute configurations of 1–8 were determined by chemical hydrolysis and modified Mosher’s and Marfey’s methods. All compounds were tested in an anti-HIV activity assay, and compound 1 showed an inhibitory effect on HIV-1 replication by targeting reverse transcriptase. Further study exhibited that 1 could block NNRTIs-resistant strains (HIV-1RT₋K₁₀₃N, HIV-1RT₋L₁₀₀I,K₁₀₃N, HIV-1RT₋K₁₀₃N,V₁₀₈I, HIV-1RT₋K₁₀₃N,G₁₉₀A, and HIV-1RT₋K₁₀₃N,P₂₂₅H) as well as wild-type HIV-1 (HIV-1wₜ) with EC₅₀ values of 7.0, 23.8, 13.3, 14.2, 6.2, and 8.4 μM, respectively.