Inhibition of HIV-1 Integrase by Galloyl Glucoses from Terminalia chebula and Flavonol Glycoside Gallates from Euphorbia pekinensis

Abstract

The bioassay-directed isolation of Terminalia chebula fruits afforded four human immunodeficiency virus type 1 (HIV-1) integrase inhibitors, gallic acid (1) and three galloyl glucoses (2 - 4). In addition, four flavonol glycoside gallates (5 - 8) from Euphorbia pekinensis containing the galloyl moiety also showed the inhibitory activity at a level comparable to those of 2 - 4. By comparison with the activities of the compounds not bearing this moiety, it is proposed that the galloyl moiety plays a major role for inhibition against the 3′-processing of HIV-1 integrase of these compounds.

References

• 1 Pommier Y, Pilon A A, Bajaj K, Mazumder A, Neamati N. HIV-1 integrase as a target for antiviral drugs.  Antiviral Chemistry and Chemotherapy. 1997;  8 463-83
• 2 Nawwar M AM, Buddrus J, Bauer H. Dimeric phenolic constituents from the roots of Tamarix nilotica .  Phytochemistry. 1982;  21 1755
• 3 Haddock E A, Gupta R K, Al-Shafi S MK, Haslam E. The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 1. Introduction. Naturally occuring galloyl esters. Journal of the Chemical Society.  Perkin Transaction I. 1982;  11 2515-24
• 4 Foo L Y. Amarinic acid and related ellagitannins from Phyllanthus amarus .  Phytochemistry. 1995;  39 217-24
• 5 Ahn B T, Zhang B K, Lee S C, Kim J G, Ro J S, Lee K S. Phenolic compounds from aerial parts of Euphorbia pekinensis .  Yakhak Hoeji. 1996;  40 170-6
• 6 Kim H J, Woo E -R, Shin C -G, Park H. A new flavonol glycoside gallate ester from Acer okamotoannum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase.  Journal of Natural Products. 1998;  61 145-8