New benzo[c]phenanthridine and benzenoid derivatives, and other constituents from Zanthoxylum ailanthoides: Effects on neutrophil pro-inflammatory responses.
A new benzo[c]phenanthridine, oxynorchelerythrine (1), and two new benzenoid derivatives, methyl 4-(2-hydroxy-4-methoxy-3-methyl-4-oxobutoxy)benzoate (2) and (E)-methyl 4-(4-((Z)-3-methoxy-3-oxoprop-1-enyl)phenoxy)-2-methylbut-2-enoate (3), have been isolated from the twigs of Zanthoxylum ailanthoides, together with 11 known compounds (4-14). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolated compounds, decarine (4), (-)-syringaresinol (6), (+)-episesamin (8), glaberide I (9), (-)-dihydrocubebin (10), and xanthyletin (11) exhibited potent inhibition (IC50 values ≤ 4.79 µg/mL) of superoxide anion generation by human nutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 4, 8, and 11 also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 5.48 µg/mL.
Faculty of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan. meinch@kmu.edu.tw.
Ching-Yi
CY
Chung
Tsong-Long
TL
Hwang
Liang-Mou
LM
Kuo
Wen-Lung
WL
Kuo
Ming-Jen
MJ
Cheng
Yi-Hsiu
YH
Wu
Ping-Jyun
PJ
Sung
Mei-Ing
MI
Chung
Jih-Jung
JJ
Chen
D001565:Benzoates / Q000737:chemistry*; D053119:Benzophenanthridines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002934:Cinnamates / Q000737:chemistry*; D006801:Humans; D006885:Hydroxybutyrates / Q000737:chemistry*; D009504:Neutrophils / Q000187:drug effects*; D013481:Superoxides / Q000037:antagonists & inhibitors; D032106:Zanthoxylum / Q000737:chemistry*
D001565:Benzoates; D053119:Benzophenanthridines; D002934:Cinnamates; D006885:Hydroxybutyrates; D013481:Superoxides