New coumarins and anti-inflammatory constituents from Zanthoxylum avicennae

被引:54
作者
Cho, Jui-Ying [3 ]
Hwang, Tsong-Long [4 ]
Chang, Tsung-Hsien [5 ]
Lim, Yun-Ping [6 ,7 ]
Sung, Ping-Jyun [8 ]
Lee, Tzong-Huei [1 ,3 ]
Chen, Jih-Jung [1 ,2 ]
机构
[1] Tajen Univ, Grad Inst Pharmaceut Technol, Yanpu Shiang 907, Pingtung, Taiwan
[2] Tajen Univ, Dept Pharm, Pingtung 907, Taiwan
[3] Taipei Med Univ, Grad Inst Pharrnacognosy, Taipei 110, Taiwan
[4] Chang Gung Univ, Grad Inst Nat Prod, Tao Yuan 333, Taiwan
[5] Kaohsiung Vet Gen Hosp, Lab Infect Dis & Immunol, Kaohsiung 813, Taiwan
[6] China Med Univ, Sch Pharm, Coll Pharm, Taichung 404, Taiwan
[7] China Med Univ Hosp, Dept Emergency, Toxicol Ctr, Taichung 404, Taiwan
[8] Natl Museum Marine Biol & Aquarium, Pingtung 944, Taiwan
关键词
Zanthoxylum avicennae; Rutaceae; Structure elucidation; Coumarins; Anti-inflammatory activity; NEUTROPHILS; ALKALOIDS; SCHINIFOLIUM; LEAVES; METABOLITES; CULTURES; INJURY; ROOT; RAT;
D O I
10.1016/j.foodchem.2012.04.025
中图分类号
O69 [应用化学];
学科分类号
070301 [无机化学];
摘要
Zanthoxylum avicennae is commercially used as healthcare products for the improvement of chronic hepatitis and rheumatism. Its fruit is also used as a spice. Five new coumarins, 5'-methoxyauraptene (1), 6,5'-dimethoxyauraptene (2), 5'-methoxycollinin (3), 7-((2'E,5'E)-7'-methoxy-3',7'-dimethylocta-2',5'-dienyloxy)coumarin (4), and 6-methoxy-7-((2'E,5'E)-7'-methoxy-3',7'-dimethylocta-2',5'-dienyloxy)coumarin (5), have been isolated from the leaves of Z. avicennae, together with 15 known compounds (6-20). The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 6, 9-15, and 18 exhibited inhibition (IC50 <= 8.29 mu g/ml) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 6, 10, 12, 14, and 18 inhibited fMLP/CB-induced elastase release with IC50 values <= 6.30 mu/ml. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:17 / 23
页数:7
相关论文
共 35 条
[1]
New pseudan (2-alkyl-4(1H)-quinolinone) alkaloids from Boronia ternata var. elongata and Boronia alulata (Rutaceae) [J].
Agier, Catherine ;
Bury, Michele ;
Aquette, Jacqueline ;
Hocquemiller, Reynald ;
Waterman, Peter G. .
NATURAL PRODUCT RESEARCH, 2007, 21 (08) :698-703
[2]
BORREGAARD N, 1988, EUR J HAEMATOL, V41, P401
[3]
Boyum A, 1968, Scand J Clin Lab Invest Suppl, V97, P77
[4]
Coumarins and anti-HBV constituents from Zanthoxylum schinifolium [J].
Chang, CT ;
Doong, SL ;
Tsai, IL ;
Chen, IS .
PHYTOCHEMISTRY, 1997, 45 (07) :1419-1422
[5]
COUMARINS AND ANTIPLATETLET AGGREGATION CONSTITUENTS FROM ZANTHOXYLUM-SCHINIFOLIUM [J].
CHEN, IS ;
LIN, YC ;
TSAI, IL ;
TENG, CM ;
KO, FN ;
ISHIKAWA, T ;
ISHII, H .
PHYTOCHEMISTRY, 1995, 39 (05) :1091-1097
[6]
Neolignans, a coumarinolignan, lignan derivatives, and a chromene:: Anti-inflammatory constituents from Zanthoxylum avicennae [J].
Chen, Jih-Jung ;
Wang, Tzu-Ying ;
Hwang, Tsong-Long .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (02) :212-217
[7]
Cheng S., 1990, ZHIWU XUEBAO, V32, P49
[8]
BENZOPHENANTHRIDINE AND FUROQUINOLINE ACCUMULATION IN CELL-SUSPENSION CULTURES OF FAGARA ZANTHOXYLOIDES [J].
COUILLEROT, E ;
CARON, C ;
COMOE, L ;
AUDRAN, JC ;
MOLINATTI, P ;
ZECHES, M ;
LEMENOLIVIER, L ;
JARDILLIER, JC ;
CHENIEUX, JC .
PHYTOCHEMISTRY, 1994, 37 (02) :425-428
[9]
Neutrophils in asthma pathophysiology [J].
Ennis, M .
CURRENT ALLERGY AND ASTHMA REPORTS, 2003, 3 (02) :159-165
[10]
COUMARIN, ALKALOID AND FLAVONOID CONSTITUENTS FROM ROOT AND STEM BARKS OF ZANTHOXYLUM-AVICENNAE [J].
FISH, F ;
GRAY, AI ;
WATERMAN, PG .
PHYTOCHEMISTRY, 1975, 14 (03) :841-842