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

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

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 (4–18). The structures of these new compounds were determined through spectroscopic a...

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Main Authors: Jih-Jung Chen, Chieh-Kai Yang, Yueh-Hsiung Kuo, Tsong-Long Hwang, Wen-Lung Kuo, Yun-Ping Lim, Ping-Jyun Sung, Tsung-Hsien Chang, Ming-Jen Cheng
Format: Article
Language:English
Published: MDPI AG 2015-04-01
Series:International Journal of Molecular Sciences
Subjects:
Zanthoxylum avicennae
Rutaceae
coumarin
structure elucidation
anti-inflammatory activity
Online Access:http://www.mdpi.com/1422-0067/16/5/9719
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spelling doaj-55c71e2dc7a24d7b94cbf36bdb3b4aa02020-11-24T21:06:33ZengMDPI AGInternational Journal of Molecular Sciences1422-00672015-04-011659719973110.3390/ijms16059719ijms16059719New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory ResponsesJih-Jung Chen0Chieh-Kai Yang1Yueh-Hsiung Kuo2Tsong-Long Hwang3Wen-Lung Kuo4Yun-Ping Lim5Ping-Jyun Sung6Tsung-Hsien Chang7Ming-Jen Cheng8Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, TaiwanDepartment of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, TaiwanDepartment of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, TaiwanGraduate Institute of Natural Products, School of Traditional Chinese Medicine, College of Medicine, Chang Gung University, Taoyuan 333, TaiwanChung-Jen Junior College of Nursing, Health Sciences and Management, Chiayi 600, TaiwanSchool of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, TaiwanNational Museum of Marine Biology and Aquarium, Pingtung 944, TaiwanDepartment of Medical Education and Research, Kaohsiung Veterans General Hospital, Kaohsiung 813, TaiwanBioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, TaiwanThree 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 (4–18). 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.http://www.mdpi.com/1422-0067/16/5/9719Zanthoxylum avicennaeRutaceaecoumarinstructure elucidationanti-inflammatory activity
collection DOAJ
language English
format Article
sources DOAJ
author Jih-Jung Chen
Chieh-Kai Yang
Yueh-Hsiung Kuo
Tsong-Long Hwang
Wen-Lung Kuo
Yun-Ping Lim
Ping-Jyun Sung
Tsung-Hsien Chang
Ming-Jen Cheng
spellingShingle Jih-Jung Chen
Chieh-Kai Yang
Yueh-Hsiung Kuo
Tsong-Long Hwang
Wen-Lung Kuo
Yun-Ping Lim
Ping-Jyun Sung
Tsung-Hsien Chang
Ming-Jen Cheng
New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses
International Journal of Molecular Sciences
Zanthoxylum avicennae
Rutaceae
coumarin
structure elucidation
anti-inflammatory activity
author_facet Jih-Jung Chen
Chieh-Kai Yang
Yueh-Hsiung Kuo
Tsong-Long Hwang
Wen-Lung Kuo
Yun-Ping Lim
Ping-Jyun Sung
Tsung-Hsien Chang
Ming-Jen Cheng
author_sort Jih-Jung Chen
title New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses
title_short New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses
title_full New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses
title_fullStr New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses
title_full_unstemmed New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses
title_sort new coumarin derivatives and other constituents from the stem bark of zanthoxylum avicennae: effects on neutrophil pro-inflammatory responses
publisher MDPI AG
series International Journal of Molecular Sciences
issn 1422-0067
publishDate 2015-04-01
description 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 (4–18). 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.
topic Zanthoxylum avicennae
Rutaceae
coumarin
structure elucidation
anti-inflammatory activity
url http://www.mdpi.com/1422-0067/16/5/9719
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