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 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.
Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan. jjchen@tajen.edu.tw.
Jih-Jung
JJ
Chen
Department of Pharmacy & Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 907, Taiwan. jacky.505@yahoo.com.tw.
Chieh-Kai
CK
Yang
Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan. kuoyh@mail.cmu.edu.tw.|Department of Biotechnology, Asia University, Taichung 413, Taiwan. kuoyh@mail.cmu.edu.tw.
Yueh-Hsiung
YH
Kuo
Graduate Institute of Natural Products, School of Traditional Chinese Medicine, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan. htl@mail.cgu.edu.tw.|Research Center for Industry of Human Ecology, Chang Gung University of Science and Technology, Immunology Consortium, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan. htl@mail.cgu.edu.tw.
Tsong-Long
TL
Hwang
Chung-Jen Junior College of Nursing, Health Sciences and Management, Chiayi 600, Taiwan. m049@cjc.edu.tw.
Wen-Lung
WL
Kuo
School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan. limyp@mail2000.com.tw.
Yun-Ping
YP
Lim
National Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan. pjsung@nmmba.gov.tw.
Ping-Jyun
PJ
Sung
Department of Medical Education and Research, Kaohsiung Veterans General Hospital, Kaohsiung 813, Taiwan. hangth@vghks.gov.tw.
Tsung-Hsien
TH
Chang
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 300, Taiwan. jacky.505@yahoo.com.tw.
Ming-Jen
MJ
Cheng
D000328:Adult; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D003571:Cytochalasin B / Q000494:pharmacology; D006801:Humans; D007249:Inflammation / Q000473:pathology*; D009682:Magnetic Resonance Spectroscopy; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000276:immunology*; D024301:Plant Bark / Q000737:chemistry*; D018547:Plant Stems / Q000737:chemistry*; D013481:Superoxides / Q000378:metabolism; D055815:Young Adult; D032106:Zanthoxylum / Q000737:chemistry*
D003374:Coumarins; D013481:Superoxides; D003571:Cytochalasin B; D009240:N-Formylmethionine Leucyl-Phenylalanine; C042205:methionyl-leucyl-phenylalanine