Anti-Aids Agents, 1. Isolation and Characterization of Four New Tetragalloylquinic Acids as a New Class of HIV Reverse Transcriptase Inhibitors from Tannic Acid

Abstract

Four new tetragalloylquinic acids, 3,5-di-0-galloyl-4-0-digalloylquinic acid [2], 3,4-di-0-galloyl-5-0-digalloylquinic acid [3], 3-0-digalloyl-4,5-di-0-galloylquinic acid [4], and 1,3,4,5-tetra-0-galloylquinic acid [5], were isolated and characterized from a commercial tannic acid as a new class of human immunodeficiency virus (HIV) reverse transcriptase (RT) inhibitor. Compounds 2,3, and 4 inhibit HIV RT activity 90, 89, and 84% at 100 .mu.M and 73,70 and 63% at 30 .mu.M, respectively. Compounds 2-5 also inhibit the HIV growth in cells in the range of 61-70% with low cytotoxicity at 25 .mu.M. The HIV cell growth inhibitory effects of these compounds at 25 .mu.M and 6.25 .mu.M (44-57%) are comparable to their effects against the HIV RT at 30 .mu.M and 10 .mu.M, respectively. The inhibitory effect of 3 against DNA polymerases indicates that the selective antiviral action of 3 is determined by more than its action with HIV RT.