Jasmonoid glucosides, sesquiterpenes and coumarins from the fruit of Clausena lansium

The fruit of Clausena lansium (wampee) is popular in southern China and warm areas of the world. Our chemical study on the fruit yielded three jasmonoid glucosides, 12-β-d-glucopyranosyloxy-6-epi-7-isocucurbic acid-1,6-lactone (1), 12-β-d-glucopyranosyloxyjasmonic acid (2) and 12-hydroxyjasmonic acid (3), two sesquiterpenes, (+)-curcumen-12-oic acid (4) and (+)-(E)-α-santalen-12-oic acid (5), two coumarins, xanthotoxol (6) and indicolactone (7), in addition to 3,4-dihydroxybenzoic acid (8), 5-hydroxymethylfuraldehyde (9), isopropyl β-d-glucopyranoside (10) and stigmasterol (11). Their structures were determined by spectroscopic methods. Compound 1 was a new metabolite and the others excluding 6 were reported from the species for the first time. Compounds 1-7 were evaluated for antioxidant and antibacterial activities. Among them, compound 6 showed antioxidant activity in ferric reducing antioxidant power (FRAP) and DPPH radical scavenging assays as well as antibacterial activity against Staphyloccocus aureus and Shigella dysenteriae, while compound 5 was active against Bacillus cereus.