Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis
1
Department of Orthopaedics, MacKay Memorial Hospital, Taipei 10449, Taiwan
2
Ph.D. Degree Program of Biomedical Science and Engineering, National Chiao Tung University, Hsinchu City 30068, Taiwan
3
Department of Medicine, MacKay Medical College, New Taipei City 25242, Taiwan
4
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 80708, Taiwan
5
Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 90741, Taiwan
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Graduate Institute of Natural Products, School of Traditional Chinese Medicine, College of Medicine, Chang Gung University, Taoyuan 33303, Taiwan
7
Research Center for Food and Cosmetic Safety, Graduate Institute of Health Industry Technology, College of Human Ecology, Chang Gung University of Science and Technology, Taoyuan 33303, Taiwan
8
Department of Anesthesiology, Chang Gung Memorial Hospital, Taoyuan 333, Taiwan
9
Bioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 30062, Taiwan
10
National Museum of Marine Biology and Aquarium, Pingtung 94450, Taiwan
11
Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, Hsinchu City 30068, Taiwan
12
Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 11221, Taiwan
13
Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 40402, Taiwan
*
Author to whom correspondence should be addressed.
†
These author contributed equally to this manuscript.
Academic Editor: Phurpa Wangchuk
Molecules 2020, 25(24), 5911; https://doi.org/10.3390/molecules25245911
Received: 14 November 2020
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Revised: 9 December 2020
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Accepted: 9 December 2020
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Published: 14 December 2020
(This article belongs to the Special Issue Bioactive Molecules and Drug Lead Compounds)
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 μg/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 μg/mL. In addition, compounds 2, 9, 11, 14, and 21 showed potent inhibition with IC50 values ≤ 27.11 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. The well-known proinflammatory cytokines, tumor necrosis factor-alpha (TNF-α) 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-α, and IL-6 through the inhibition of activation of MAPKs and IκBα in LPS-activated macrophages. In addition, compounds 1, 9, and 14 stimulated anti-inflammatory M2 phenotype by elevating the expression of arginase 1 and Krüppel-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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Keywords:
Fraxinus chinensis; Oleaceae; stem bark; secoiridoid; anti-inflammatory activity
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MDPI and ACS Style
Chang, H.-C.; Wang, S.-W.; Chen, C.-Y.; Hwang, T.-L.; Cheng, M.-J.; Sung, P.-J.; Liao, K.-W.; Chen, J.-J. Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis. Molecules 2020, 25, 5911. https://doi.org/10.3390/molecules25245911
AMA Style
Chang H-C, Wang S-W, Chen C-Y, Hwang T-L, Cheng M-J, Sung P-J, Liao K-W, Chen J-J. Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis. Molecules. 2020; 25(24):5911. https://doi.org/10.3390/molecules25245911
Chicago/Turabian StyleChang, Hao-Chiun, Shih-Wei Wang, Chin-Yen Chen, Tsong-Long Hwang, Ming-Jen Cheng, Ping-Jyun Sung, Kuang-Wen Liao, and Jih-Jung Chen. 2020. "Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of Fraxinus chinensis" Molecules 25, no. 24: 5911. https://doi.org/10.3390/molecules25245911
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