Antiinflammatory constituents from Heterotheca inuloides

Three new compounds, cadalen-15-oic acid (1), 3,7-dihydroxy-3(4H)-isocadalen-4-one (2), and dicadalenol (3), were isolated from the aerial parts of Heterotheca inuloides (Mexican arnica), together with the known compounds 7-hydroxycadalene (4), 7-hydroxy-4 alphaH-3,4-dihydrocadalene (5), 1 alpha -hydroxy-1(4H)-isocadalen-4-one (6), 1 alpha -hydroxy-4 alphaH-1,2,3,4-tetrahydrocadalen-15-oic acid (7), 7-(3,3-dimethylallyloxy)coumarin, caryolan-1,9 beta -diol, and quercetin. The structures of the new compounds were elucidated by spectroscopic methods. The antiinflammatory activities of the extracts and the isolated compounds were evaluated by determining the inhibition of TPA-induced mouse ear edema. The natural products 3, caryolan-1,9,beta -diol, and quercetin were the most active substances tested and displayed dose-dependent activities.