Two new compounds and anti-HIV active constituents from Illicium verum

Two new compounds named illiverin A (1) and tashironin A (8) were, isolated from the roots of Illicium verum, together with seven known compounds: 4-allyl-2-(3-methylbut-2-enyl)-1,6-methylenedioxybenzene-3-ol (2), illicinole (3), 3-hydroxy-4,5-methylenedioxyallyl-benzene (4),(-)-illicinone-A (5), 4-allyl-4-(3-methylbut-2-enyl)-1,2-methylenedioxycyclohexa-2,6-dien-5-one (6), 3,4-seco-(24Z)- cycloart-4(28),24-diene-3,26-dioic acid, 26-methyl ester (7)and tashironin (9). Based on 1D- and 2D-NMR data (COSY, HMQC, HMBC), the structures of the new compounds were deduced to be (E)-1-[(3-methylbut-2-enyl)oxy]-2-methoxy-4-(prop-1-enyl)benzene (1) and 11-O-2-debenzoyl-11 alpha-O-2-methylcyclopent-1- enecarboxyltashironin (8). Compounds 1 - 9 were screened for anti-HIV activity in vitro whereby compounds 5 and 7 possessed moderate anti-HIV activity with EC50 values of 16.0 and 5.1 mu M with SI values of 18.2 and 15.6, respectively.