Abstract
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.
Highlights
Zanthoxylum ailanthoides Sieb. & Zucc. (Rutaceae) is a medium-to-large-sized tree, found at low altitude in forests of China, Japan, Korea, Philippines, and Taiwan [1]
The presence of carbonyl group was revealed by the band at 1644 cm−1 in the IR spectrum, which was confirmed by the resonance at δC 162.4 in the 13C-Nuclear magnetic resonance (NMR) spectrum
Phosphorylation of JNK caused by fMLP was most significantly inhibited by these compounds. These results suggest that the anti-inflammatory effects of compounds 4, 8, and 11 are through the inhibition of activation of Mitogen-activated protein kinases (MAPKs) and Akt in fMLP-activated neutrophils
Summary
Zanthoxylum ailanthoides Sieb. & Zucc. (Rutaceae) is a medium-to-large-sized tree, found at low altitude in forests of China, Japan, Korea, Philippines, and Taiwan [1]. Various benzo[c]phenanthridines, coumarins, lignans, flavonoids, quinolines, benzenoids, and triterpenoids are widely distributed in this plant [2,3,4,5,6,7,8,9,10,11,12]. Many of these compounds exhibit anti-platelet aggregation [10], anti-HIV [11], and anti-inflammatory [12] activities.
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