Amides and benzenoids from Zanthoxylum ailanthoides with inhibitory activity on superoxide generation and elastase release by neutrophils.
Five new compounds, ailanthamide (1), N-(4-methoxyphenethyl)-N-methylbenzamide (2), (2E,4E)-N-isobutyl-6-oxohepta-2,4-dienamide (3), 4-(4'-hydroxy-3'-methylbutoxy)benzaldehyde (4), and (E)-methyl 4-[4-(3-hydroxypropyl)phenoxy]-2-methylbut-2-enoate (5), and 17 known compounds have been isolated from the stem bark of Zanthoxylum ailanthoides. The structures were determined through spectroscopic and MS analyses. Compounds 1, 3, xanthyletin, decarine, (+)-episesamin, (-)-hinokinin, and evofolin-B exhibited inhibition (IC(50) < or = 5.34 microg/mL) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, xanthyletin, decarine, and (+)-episesamin also inhibited fMLP/CB-induced elastase release with IC(50) values < or = 5.53 microg/mL.
Chen
Jih-Jung
JJ
Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan, Republic of China. jjchen@mail.tajen.edu.tw
Chung
Ching-Yi
CY
Hwang
Tsong-Long
TL
Chen
Jinn-Fen
JF
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000494:pharmacology; D000577:Amides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001549:Benzamides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001555:Benzene Derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D052117:Benzodioxoles; D003374:Coumarins / Q000494:pharmacology; D004149:Dioxoles / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D017705:Lignans / Q000494:pharmacology; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects* / Q000378:metabolism; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D024301:Plant Bark / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013481:Superoxides / Q000037:antagonists & inhibitors*; D013624:Taiwan; D032106:Zanthoxylum / Q000737:chemistry*
D000577:Amides; D001549:Benzamides; D001555:Benzene Derivatives; D052117:Benzodioxoles; D003374:Coumarins; D004149:Dioxoles; D017705:Lignans; D013481:Superoxides; C475934:hinokinin; C020814:xanthyletine; D010196:Pancreatic Elastase; D015107:4-Butyrolactone; C054125:sesamin