New benzenoids and anti-inflammatory constituents from Zanthoxylum nitidum

Zanthoxylum nitidum is commercially used in healthcare products for the improvement of tooth condition. Its fruit is also used as a spice. Three new benzenoids, (E)-4-(4-hydroxy-3-methylbut-2-enyloxy)benzaldehyde (1), (E)-methyl 3-(44(E)-4-hydroxy-3-methylbut-2-enyloxy)phenyl)acrylate (2), and (Z)-methyl 3-(4-((E)-4-hydroxy-3-methylbut-2-enyloxy)phenyl)acrylate (3), have been isolated from the stem wood of Z. nitidum, together with 17 known compounds (4-20). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 8-10, 13, 14, 17, and 18 exhibited inhibition (IC50 <= 7.95 mu g/ml) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 7-9, 13, 14, and 17 inhibited (fMLP/CB-induced elastase release with IC50 values <= 7 45 mu g/ml. (C) 2010 Elsevier Ltd All rights reserved.