The caffeoylquinic acids 3,4,5-tri-O-caffeoylquinic acid (1) and 4,5-di-O-caffeoylquinic acid (2), as well as caffeic acid (4) and synapoic acid (5) were isolated from the plant Securidaka longipedunculata (polygalaceae). 1 exhibited a greater selective inhibition of HIV replication than 2 which had an anti-HIV activity similar to that of 3,4,5-tri-O-galloylquinic acid (3), isolated from Guiera senegalensis (combretaceae); 4 and 5 were ineffective and the structurally related compound rosmarinic acid (6) had only slight anti-HIV activity. Studies of the actions of these compounds suggest that inhibition of the viral reverse transcriptase in vitro is non-specific and that they act by specific binding to gp120 which prevents its interaction with CD4 on T-lymphocytes and thus inactivates virus infectivity.
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