Anti HIV-1 Flavonoid Glycosides from Ochna integerrima

Abstract

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/revMC99 virus and the 1A2 cell line system with EC₅₀ 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 EC₅₀ values of 2.0 and 0.9 μg/mL, respectively, and likewise inhibited HIV-1 reverse transcriptase (RT) with IC₅₀ values of 2.0 and 2.4 μg/mL, respectively.

Abbreviations

AZT: azidothymidine

CC: column chromatography

prep. TLC: preparative thin layer chromatography

Key words

Ochna integerrima - flavonoid glycosides - Ochnaceae - anti-syncytium activity - anti-HIV-1 RT activity

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