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Int. J. Mol. Sci. 2013, 14(11), 22395-22408; doi:10.3390/ijms141122395

New Benzo[c]phenanthridine and Benzenoid Derivatives, and Other Constituents from Zanthoxylum ailanthoides: Effects on Neutrophil Pro-Inflammatory Responses

1
Faculty of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
2
Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan
3
Graduate Institute of Clinical Medical Sciences, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan
4
Department of General Surgery, Chang Gung Memorial Hospital at Chia-Yi, Chia-Yi 613, Taiwan
5
Chung-Jen College of Nursing, Health Science and Management, Chiayi 600, Taiwan
6
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan
7
National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan
8
Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 6 August 2013 / Revised: 24 October 2013 / Accepted: 25 October 2013 / Published: 13 November 2013
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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 (414). 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.
Keywords: Zanthoxylum ailanthoides; Rutaceae; benzo[c]phenanthridine; benzenoid; anti-inflammatory activity Zanthoxylum ailanthoides; Rutaceae; benzo[c]phenanthridine; benzenoid; anti-inflammatory activity
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MDPI and ACS Style

Chung, C.-Y.; Hwang, T.-L.; Kuo, L.-M.; Kuo, W.-L.; Cheng, M.-J.; Wu, Y.-H.; Sung, P.-J.; Chung, M.-I.; Chen, J.-J. New Benzo[c]phenanthridine and Benzenoid Derivatives, and Other Constituents from Zanthoxylum ailanthoides: Effects on Neutrophil Pro-Inflammatory Responses. Int. J. Mol. Sci. 2013, 14, 22395-22408.

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