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Int. J. Mol. Sci. 2015, 16(5), 9719-9731; doi:10.3390/ijms16059719

New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses

1
Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan
2
Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan
3
Department of Biotechnology, Asia University, Taichung 413, Taiwan
4
Graduate Institute of Natural Products, School of Traditional Chinese Medicine, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan
5
Research Center for Industry of Human Ecology, Chang Gung University of Science and Technology, Immunology Consortium, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan
6
Chung-Jen Junior College of Nursing, Health Sciences and Management, Chiayi 600, Taiwan
7
School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan
8
National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan
9
Department of Medical Education and Research, Kaohsiung Veterans General Hospital, Kaohsiung 813, Taiwan
10
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Marcello Iriti
Received: 17 March 2015 / Revised: 10 April 2015 / Accepted: 14 April 2015 / Published: 29 April 2015
(This article belongs to the Special Issue Plant Molecular Biology)
View Full-Text   |   Download PDF [746 KB, uploaded 29 April 2015]   |  

Abstract

Three new coumarin derivatives, 8-formylalloxanthoxyletin (1), avicennone (2), and (Z)-avicennone (3), have been isolated from the stem bark of Zanthoxylum avicennae (Z. avicennae), together with 15 known compounds (418). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 4, 9, 12, and 15 exhibited inhibition (half maximal inhibitory concentration (IC50) values ≤7.65 µg/mL) of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 2, 4, 8 and 9 inhibited fMLP/CB-induced elastase release with IC50 values ≤8.17 µg/mL. This investigation reveals bioactive isolates (especially 1, 2, 4, 8, 9, 12 and 15) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases. View Full-Text
Keywords: Zanthoxylum avicennae; Rutaceae; coumarin; structure elucidation; anti-inflammatory activity Zanthoxylum avicennae; Rutaceae; coumarin; structure elucidation; anti-inflammatory activity
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Chen, J.-J.; Yang, C.-K.; Kuo, Y.-H.; Hwang, T.-L.; Kuo, W.-L.; Lim, Y.-P.; Sung, P.-J.; Chang, T.-H.; Cheng, M.-J. New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses. Int. J. Mol. Sci. 2015, 16, 9719-9731.

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