Terpenoids from Stinking toe (Hymneae courbaril) fruits with cyclooxygenase and lipid peroxidation inhibitory activities

Stinking toe (Hymenaea courbaril), also called Jatoba and Kerosene tree, is a medicinal plant commonly found in the central and South American countries. In the Caribbean, Mexico and Brazil, the powdery sweet dust of its fruit is consumed for energy. The chemical examination of the yellowish sweet powder of the fruit yielded sucrose and linolenic acid as major compounds. The pods yielded the labdane diterpenoids crotomachlin (1), labd-13E-en-8-ol-15-oic acid (2), labdanolic acid (4), (13E)-labda 7, 13 dien-15-oic acid (5) and labd-8 (17), 13E-dien-15-oic acid (6), along with the sesquiterpene, spathulenol (7), as confirmed by 1 H and 13 C NMR spectral studies. The methyl ester of labd-13E-en-8-ol-15-oic acid (3) was also characterized during the purification of compound 5. The total amount of these terpenoids in the fruit was about 0.1% (w/w) of the dried fruit. Compounds 1-5 and 7 were assayed for anti-inflammatory activity using cyclooxygenase-1 (COX-1) and -2 (COX-2) enzymes. At 100 ppm, compounds 3 and 4 showed selective COX-2 enzyme inhibition. Also, compounds 1, 2 and 5 inhibited lipid peroxidation by 46%, 48% and 75%, respectively, at 100 ppm. These compounds were isolated from this fruit and their COX and lipid peroxidation inhibitory activities are reported for the first time in this paper. (c) 2007 Elsevier Ltd. All rights reserved.