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

Abstract

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.

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…Park and colleagues reported that two polybromocatechol compounds ( 99 , 100 ), isolated from the red alga Neorhodomela aculeate , inhibited infection and cytopathic effects on a HeLa cell line by HRV2 and HRV3, causal agents of viral respiratory infections and common colds [99]. Ma and colleagues determined that the novel phenylspirodrimane stachybotrin D ( 101 ), isolated from the fungus Stachybotrys chartarum MXH-X73 derived from the Chinese marine sponge Xestospongia testudinaria , inhibited HIV-1 replication of wild-type and five non-nucleoside reverse transcriptase inhibitor (NNRTI)-resistant HIV-1 strains by inhibiting the reverse transcriptase, and thus “provides a new class of chemotype for the search of NNRT inhibitors” [100]. Jiao and colleagues reported that streptoseolactone ( 102 ), derived from the actinomycete Streptomyces seoulensis strain isolated from the shrimp Penasus orientalis , inhibited neuraminidase by a noncompetitive mechanism, a finding “of value in terms of drug discovery for the treatment of influenza” [101].…”

Isocoumarin Derivatives from the Sponge‐Associated Fungus Peyronellaea glomerata with Antioxidant Activities

“…Thus, the substitution of a Cl-atom at the methine C(11) was supposed. 2) assigned C(10) and C (12) to be in (R)-and (S)-configuration, respectively. Based on the modified Mosher's method for n-diols by NMR data [14], the Dd (d Rd S ) values of the methoxyphenylacetic acid (MPA) esters of 1 were calculated.…”

“…The linkage of the pentane unit to C(3) (d(C) 155.2) was assigned by the HMBC interaction from H-C(4) (d(H) 6.57) to C(9) (d(C) 39.0) and C (10). The coupling constants (J(10,9a) = 4.2 Hz, J(10,9b) = 8.9 Hz, J(10,11) = 4.0 Hz, J (11,12) = 8.2 Hz) reflected gauche relationship between H-C(10)/H a -C(9) and H-C(10)/H-C(11), and antiorientation between H-C(10)/H b -C(9) and H-C(11)/H-C (12). The positive Dd data of H-C(10) (+0.098) and CH 2 (9) (+0.6942, +0.4783) and the negative Dd data of H-C(12) (À0.4114) and Me(13) (À0.6248) (Fig.…”

“…2) assigned C(10) and C(12) to be in (R)-and (S)-configurations, respectively.Comparison of the NMR data disclosed the similar resonances of both peyroisocoumarin C (3) and 1 ( 2) assigned C(10) and C(12) to be in (R)-and (S)-configurations, respectively.Comparison of the NMR data disclosed the similar resonances of both peyroisocoumarin C (3) and 1 (…”

Metabolism of F18, a Derivative of Calanolide A, in Human Liver Microsomes and Cytosol

“…The metabolites M1, M2-9, M3-1, M3-2, M5-2, M5-3, M5-4, and M5-5 were screened for their activities against HIV-1 using pseudotyped viruses as described previously (Ma et al, 2013). Briefly, VSV-G/HIV-1 viruses were prepared by co-transfecting 293T cells with VSV-G plasmid and env-deficient HIV-1 vector (pNL4-3.luc.R-E-, Supplemental Figures S1, S2).…”