Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis

被引:11
作者
Chang, Hao-Chiun [1 ,2 ]
Wang, Shih-Wei [3 ,4 ]
Chen, Chin-Yen [5 ]
Hwang, Tsong-Long [6 ,7 ,8 ]
Cheng, Ming-Jen [9 ]
Sung, Ping-Jyun [4 ,10 ]
Liao, Kuang-Wen [2 ,11 ]
Chen, Jih-Jung [12 ,13 ]
机构
[1] MacKay Mem Hosp, Dept Orthopaed, Taipei 10449, Taiwan
[2] Natl Chiao Tung Univ, PhD Degree Program Biomed Sci & Engn, Hsinchu 30068, Taiwan
[3] MacKay Med Coll, Dept Med, New Taipei 25242, Taiwan
[4] Kaohsiung Med Univ, Grad Inst Nat Prod, Kaohsiung 80708, Taiwan
[5] Tajen Univ, Grad Inst Pharmaceut Technol, Pingtung 90741, Taiwan
[6] Chang Gung Univ, Coll Med, Sch Tradit Chinese Med, Grad Inst Nat Prod, Taoyuan 33303, Taiwan
[7] Chang Gung Univ Sci & Technol, Coll Human Ecol, Grad Inst Hlth Ind Technol, Res Ctr Food & Cosmet Safety, Taoyuan 33303, Taiwan
[8] Chang Gung Mem Hosp, Dept Anesthesiol, Taoyuan 333, Taiwan
[9] Food Ind Res & Dev Inst FIRDI, Bioresource Collect & Res Ctr BCRC, Hsinchu 30062, Taiwan
[10] Natl Museum Marine Biol & Aquarium, Pingtung 94450, Taiwan
[11] Natl Chiao Tung Univ, Inst Mol Med & Bioengn, Hsinchu 30068, Taiwan
[12] Natl Yang Ming Univ, Sch Pharmaceut Sci, Fac Pharm, Taipei 11221, Taiwan
[13] China Med Univ, China Med Univ Hosp, Dept Med Res, Taichung 40402, Taiwan
来源
MOLECULES | 2020年 / 25卷 / 24期
关键词
Fraxinus chinensis; Oleaceae; stem bark; secoiridoid; anti-inflammatory activity; CHEMICAL-CONSTITUENTS; SUPEROXIDE; FLOWERS; FRUITS; ROOTS; CELLS;
D O I
10.3390/molecules25245911
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Qin Pi (Fraxinus chinensis Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), and 3 '',4 ''-di-O-methyl-demethyloleuropein (3), have been isolated from the stem bark of Fraxinus chinensis, together with 23 known compounds (4-26). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8E)-4 ''-O-methylligstroside (1), (8E)-4 ''-O-methyldemethylligstroside (2), 3 '',4 ''-di-O-methyldemethyloleuropein (3), oleuropein (6), aesculetin (9), isoscopoletin (11), aesculetin dimethyl ester (12), fraxetin (14), tyrosol (21), 4-hydroxyphenethyl acetate (22), and (+)-pinoresinol (24) exhibited inhibition (IC50 <= 7.65 mu g/mL) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leuckyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1, 9, 11, 14, 21, and 22 inhibited fMLP/CB-induced elastase release with IC50 <= 3.23 mu g/mL. In addition, compounds 2, 9, 11, 14, and 21 showed potent inhibition with IC50 values <= 27.11 mu M, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. The well-known proinflammatory cytokines, tumor necrosis factor-alpha (TNF-alpha) and interleukin 6 (IL-6), were also inhibited by compounds 1, 9, and 14. Compounds 1, 9, and 14 displayed an anti-inflammatory effect against NO, TNF-alpha, and IL-6 through the inhibition of activation of MAPKs and I kappa B alpha in LPS-activated macrophages. In addition, compounds 1, 9, and 14 stimulated anti-inflammatory M2 phenotype by elevating the expression of arginase 1 and Kruppel-like factor 4 (KLF4). The above results suggested that compounds 1, 9, and 14 could be considered as potential compounds for further development of NO production-targeted anti-inflammatory agents.
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页数:19
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