Planta Med 2007; 73(7): 683-688
DOI: 10.1055/s-2007-981538
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Anti HIV-1 Flavonoid Glycosides from Ochna integerrima

Vichai Reutrakul1 , Niwat Ningnuek1 , Manat Pohmakotr1 , Chalobon Yoosook2 , Chanita Napaswad2 , Jitra Kasisit2 , Thawatchai Santisuk3 , Patoomratana Tuchinda1
  • 1Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, Thailand
  • 2Department of Microbiology, Faculty of Science, Mahidol University, Bangkok, Thailand
  • 3The Forest Herbarium, Royal Forest Department, Bangkok, Thailand
Further Information

Publication History

Received: November 8, 2006 Revised: May 1, 2007

Accepted: May 4, 2007

Publication Date:
11 June 2007 (online)

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

References

Prof. Dr. Vichai Reutrakul

Department of Chemistry

Faculty of Science

Mahidol University·

Rama 6 Road

Bangkok 10400

Thailand

Phone: +66-2-201-5152

Fax: +66-2-644-5126·

Email: scvrt@mahidol.ac.th

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