Anti HIV-1 flavonoid glycosides from Ochna integerrima

Bioassay-guided fractionation of the anti-HIV-1 active EtOAc extract from leaves and twigs of OCHNA INTEGERRIMA led to the isolation of five new flavonoid glycosides 1 - 5, five known flavonoids 6 - 10, and two known flavonoid glycosides 11 and 12. Structures were determined based on spectroscopic analyses. 6- γ, γ-Dimethylallyldihydrokaempferol 7- O- β- D-glucoside ( 1), 6- γ, γ-dimethylallylquercetin 7- O- β- D-glucoside ( 3), 6-(3-hydroxy-3-methylbutyl)taxifolin 7- O- β- D-glucoside ( 4), 6-(3-hydroxy-3-methylbutyl)quercetin 7- O- β- D-glucoside ( 5), and 6- γ, γ-dimethylallyltaxifolin 7- O- β- D-glucoside ( 11) showed anti-HIV-1 activities in the syncytium assay using the ΔTat/rev MC99 virus and the 1A2 cell line system with EC 50 values ranging from 14.0 - 102.4 μg/mL. Furthermore, ochnaflavone 7″- O-methyl ether ( 7) and 2″, 3″-dihydroochnaflavone 7″- O-methyl ether ( 8) were very active; they exerted activities in the syncytium assay with EC 50 values of 2.0 and 0.9 μg/mL, respectively, and likewise inhibited HIV-1 reverse transcriptase (RT) with IC 50 values of 2.0 and 2.4 μg/mL, respectively. AZT: azidothymidine CC: column chromatography prep. TLC: preparative thin layer chromatography