Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of <i>Fraxinus chinensis</i>
Qin Pi (<i>Fraxinus chinensis</i> Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8<i>E</i>)-4′′-<i>O</i>-methylligstroside (<b>1</b>...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/24/5911 |
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| author | Hao-Chiun Chang Shih-Wei Wang Chin-Yen Chen Tsong-Long Hwang Ming-Jen Cheng Ping-Jyun Sung Kuang-Wen Liao Jih-Jung Chen |
| author_facet | Hao-Chiun Chang Shih-Wei Wang Chin-Yen Chen Tsong-Long Hwang Ming-Jen Cheng Ping-Jyun Sung Kuang-Wen Liao Jih-Jung Chen |
| author_sort | Hao-Chiun Chang |
| collection | DOAJ |
| description | Qin Pi (<i>Fraxinus chinensis</i> Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8<i>E</i>)-4′′-<i>O</i>-methylligstroside (<b>1</b>), (8<i>E</i>)-4′′-<i>O</i>-methyldemethylligstroside (<b>2</b>), and 3′′,4′′-di-<i>O</i>-methyl-demethyloleuropein (<b>3</b>), have been isolated from the stem bark of <i>Fraxinus chinensis</i>, together with 23 known compounds (<b>4</b>–<b>26</b>). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8<i>E</i>)-4′′-<i>O</i>-methylligstroside (<b>1</b>), (8<i>E</i>)-4′′-<i>O</i>-methyldemethylligstroside (<b>2</b>), 3′′,4′′-di-<i>O</i>-methyldemethyloleuropein (<b>3</b>), oleuropein (<b>6</b>), aesculetin (<b>9</b>), isoscopoletin (<b>11</b>), aesculetin dimethyl ester (<b>12</b>), fraxetin (<b>14</b>), tyrosol (<b>21</b>), 4-hydroxyphenethyl acetate (<b>22</b>), and (+)-pinoresinol (<b>24</b>) exhibited inhibition (IC<sub>50</sub> ≤ 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 <b>1</b>, <b>9</b>, <b>11</b>, <b>14</b>, <b>21</b>, and <b>22</b> inhibited fMLP/CB-induced elastase release with IC<sub>50</sub> ≤ 3.23 μg/mL. In addition, compounds <b>2</b>, <b>9</b>, <b>11</b>, <b>14</b>, and <b>21</b> showed potent inhibition with IC<sub>50</sub> values ≤ 27.11 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. The well-known proinflammatory cytokines<i>,</i> tumor necrosis factor-alpha (TNF-α) and interleukin 6 (IL-6), were also inhibited by compounds <b>1</b>, <b>9</b>, and <b>14</b>. Compounds <b>1</b>, <b>9</b>, and <b>14</b> 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 <b>1</b>, <b>9</b>, and <b>14</b> stimulated anti-inflammatory M2 phenotype by elevating the expression of arginase 1 and Krüppel-like factor 4 (KLF4). The above results suggested that compounds <b>1</b>, <b>9</b>, and <b>14</b> could be considered as potential compounds for further development of NO production-targeted anti-inflammatory agents. |
| first_indexed | 2024-03-10T14:06:26Z |
| format | Article |
| id | doaj.art-f5c9eeb3de154d328eb9b0b88234ee08 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T14:06:26Z |
| publishDate | 2020-12-01 |
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| series | Molecules |
| spelling | doaj.art-f5c9eeb3de154d328eb9b0b88234ee082023-11-21T00:39:15ZengMDPI AGMolecules1420-30492020-12-012524591110.3390/molecules25245911Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of <i>Fraxinus chinensis</i>Hao-Chiun Chang0Shih-Wei Wang1Chin-Yen Chen2Tsong-Long Hwang3Ming-Jen Cheng4Ping-Jyun Sung5Kuang-Wen Liao6Jih-Jung Chen7Department of Orthopaedics, MacKay Memorial Hospital, Taipei 10449, TaiwanDepartment of Medicine, MacKay Medical College, New Taipei City 25242, TaiwanGraduate Institute of Pharmaceutical Technology, Tajen University, Pingtung 90741, TaiwanGraduate Institute of Natural Products, School of Traditional Chinese Medicine, College of Medicine, Chang Gung University, Taoyuan 33303, TaiwanBioresource Collection and Research Center (BCRC), Food Industry Research and Development Institute (FIRDI), Hsinchu 30062, TaiwanGraduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 80708, TaiwanPh.D. Degree Program of Biomedical Science and Engineering, National Chiao Tung University, Hsinchu City 30068, TaiwanFaculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 11221, TaiwanQin Pi (<i>Fraxinus chinensis</i> Roxb.) is commercially used in healthcare products for the improvement of intestinal function and gouty arthritis in many countries. Three new secoiridoid glucosides, (8<i>E</i>)-4′′-<i>O</i>-methylligstroside (<b>1</b>), (8<i>E</i>)-4′′-<i>O</i>-methyldemethylligstroside (<b>2</b>), and 3′′,4′′-di-<i>O</i>-methyl-demethyloleuropein (<b>3</b>), have been isolated from the stem bark of <i>Fraxinus chinensis</i>, together with 23 known compounds (<b>4</b>–<b>26</b>). The structures of the new compounds were established by spectroscopic analyses (1D, 2D NMR, IR, UV, and HRESIMS). Among the isolated compounds, (8<i>E</i>)-4′′-<i>O</i>-methylligstroside (<b>1</b>), (8<i>E</i>)-4′′-<i>O</i>-methyldemethylligstroside (<b>2</b>), 3′′,4′′-di-<i>O</i>-methyldemethyloleuropein (<b>3</b>), oleuropein (<b>6</b>), aesculetin (<b>9</b>), isoscopoletin (<b>11</b>), aesculetin dimethyl ester (<b>12</b>), fraxetin (<b>14</b>), tyrosol (<b>21</b>), 4-hydroxyphenethyl acetate (<b>22</b>), and (+)-pinoresinol (<b>24</b>) exhibited inhibition (IC<sub>50</sub> ≤ 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 <b>1</b>, <b>9</b>, <b>11</b>, <b>14</b>, <b>21</b>, and <b>22</b> inhibited fMLP/CB-induced elastase release with IC<sub>50</sub> ≤ 3.23 μg/mL. In addition, compounds <b>2</b>, <b>9</b>, <b>11</b>, <b>14</b>, and <b>21</b> showed potent inhibition with IC<sub>50</sub> values ≤ 27.11 μM, against lipopolysaccharide (LPS)-induced nitric oxide (NO) generation. The well-known proinflammatory cytokines<i>,</i> tumor necrosis factor-alpha (TNF-α) and interleukin 6 (IL-6), were also inhibited by compounds <b>1</b>, <b>9</b>, and <b>14</b>. Compounds <b>1</b>, <b>9</b>, and <b>14</b> 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 <b>1</b>, <b>9</b>, and <b>14</b> stimulated anti-inflammatory M2 phenotype by elevating the expression of arginase 1 and Krüppel-like factor 4 (KLF4). The above results suggested that compounds <b>1</b>, <b>9</b>, and <b>14</b> could be considered as potential compounds for further development of NO production-targeted anti-inflammatory agents.https://www.mdpi.com/1420-3049/25/24/5911<i>Fraxinus chinensis</i>Oleaceaestem barksecoiridoidanti-inflammatory activity |
| spellingShingle | Hao-Chiun Chang Shih-Wei Wang Chin-Yen Chen Tsong-Long Hwang Ming-Jen Cheng Ping-Jyun Sung Kuang-Wen Liao Jih-Jung Chen Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of <i>Fraxinus chinensis</i> Molecules <i>Fraxinus chinensis</i> Oleaceae stem bark secoiridoid anti-inflammatory activity |
| title | Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of <i>Fraxinus chinensis</i> |
| title_full | Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of <i>Fraxinus chinensis</i> |
| title_fullStr | Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of <i>Fraxinus chinensis</i> |
| title_full_unstemmed | Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of <i>Fraxinus chinensis</i> |
| title_short | Secoiridoid Glucosides and Anti-Inflammatory Constituents from the Stem Bark of <i>Fraxinus chinensis</i> |
| title_sort | secoiridoid glucosides and anti inflammatory constituents from the stem bark of i fraxinus chinensis i |
| topic | <i>Fraxinus chinensis</i> Oleaceae stem bark secoiridoid anti-inflammatory activity |
| url | https://www.mdpi.com/1420-3049/25/24/5911 |
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