The caffeoylquinic acids 3,4,5-tri-O-caffeoylquinic acid (1) and 4,5-d
i-O-caffeoylquinic acid (2), as well as caffeic acid (4) and synapoic
acid (5) were isolated from the plant Securidaka longipedunculata (pol
ygalaceae). 1 exhibited a greater selective inhibition of HIV replicat
ion than 2 which had an anti-HIV activity similar to that of 3,4,5-tri
-O-galloylquinic acid (3), isolated from Guiera senegalensis (combreta
ceae); 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 revers
e transcriptase in vitro is non-specific and that they act by specific
binding to gp120 which prevents its interaction with CD4 on T-lymphoc
ytes and thus inactivates virus infectivity.