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

Seven new phenylspirodrimanes, named stachy-botrins 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-1(RT-K103N), HIV-1(RT-L1001,K103N), HIV-1(RT-K103N,V1081), HIV-1(RT-K103N,G190A), HIV-1(RT-K103N,P225H)) as well as wild-type HIV-1 (HIV-1(wt)) with EC50 values of 7.0, 23.8, 13.3, 14.2, 6.2, and 8.4 mu M, respectively.