Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from <i>Ginkgo biloba</i> Fruits and the Identification of Estrogenic Phenolic Glycosides
<i>Ginkgo biloba</i> L. stands as one of the oldest living tree species, exhibiting a diverse range of biological activities, including antioxidant, neuroprotective, anti-inflammatory, and cardiovascular activities. As part of our ongoing discovery of novel bioactive components from natu...
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| Format: | Article |
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MDPI AG
2023-11-01
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| Series: | Plants |
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| Online Access: | https://www.mdpi.com/2223-7747/12/23/3970 |
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| author | Chen Huo Quynh Nhu Nguyen Akida Alishir Moon-Jin Ra Sang-Mi Jung Jeong-Nam Yu Hui-Jeong Gwon Ki Sung Kang Ki Hyun Kim |
| author_facet | Chen Huo Quynh Nhu Nguyen Akida Alishir Moon-Jin Ra Sang-Mi Jung Jeong-Nam Yu Hui-Jeong Gwon Ki Sung Kang Ki Hyun Kim |
| author_sort | Chen Huo |
| collection | DOAJ |
| description | <i>Ginkgo biloba</i> L. stands as one of the oldest living tree species, exhibiting a diverse range of biological activities, including antioxidant, neuroprotective, anti-inflammatory, and cardiovascular activities. As part of our ongoing discovery of novel bioactive components from natural sources, we directed our focus toward the investigation of potential bioactive compounds from <i>G. biloba</i> fruit. The profiles of its chemical compounds were examined using a Global Natural Products Social (GNPS)-based molecular networking analysis. Guided by this, we successfully isolated and characterized 11 compounds from <i>G. biloba</i> fruit, including (<i>E</i>)-coniferin (<b>1</b>), syringin (<b>2</b>), 4-hydroxybenzoic acid 4-<i>O</i>-β-D-glucopyranoside (<b>3</b>), vanillic acid 4-<i>O</i>-β-D-glucopyranoside (<b>4</b>), syringic acid 4-<i>O</i>-β-D-glucopyranoside (<b>5</b>), (<i>E</i>)-ferulic acid 4-<i>O</i>-β-D-glucoside (<b>6</b>), (<i>E</i>)-sinapic acid 4-<i>O</i>-β-D-glucopyranoside (<b>7</b>), (1′<i>R</i>,2′<i>S</i>,5′<i>R</i>,8′<i>S</i>,2′<i>Z</i>,4′<i>E</i>)-dihydrophaseic acid 3′-<i>O</i>-β-D-glucopyranoside (<b>8</b>), eucomic acid (<b>9</b>), rutin (<b>10</b>), and laricitrin 3-rutinoside (<b>11</b>). The structural identification was validated through a comprehensive analysis involving nuclear magnetic resonance (NMR) spectroscopic data and LC/MS analyses. All isolated compounds were evaluated using an E-screen assay for their estrogen-like effects in MCF-7 cells. As a result, compounds <b>2</b>, <b>3</b>, <b>4</b>, <b>8</b>, and <b>9</b> promoted cell proliferation in MCF-7 cells, and these effects were mitigated by the ER antagonist, ICI 182,780. In particular, cell proliferation increased most significantly to 140.9 ± 6.5% after treatment with 100 µM of compound <b>2</b>. The mechanism underlying the estrogen-like effect of syringin (<b>2</b>) was evaluated using a Western blot analysis to determine the expression of estrogen receptor α (ERα). We found that syringin (<b>2</b>) induced an increase in the phosphorylation of ERα. Overall, these experimental results suggest that syringin (<b>2</b>) can potentially aid the control of estrogenic activity during menopause. |
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| spelling | doaj.art-ac83136656814436b06019a4222182402023-12-08T15:23:48ZengMDPI AGPlants2223-77472023-11-011223397010.3390/plants12233970Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from <i>Ginkgo biloba</i> Fruits and the Identification of Estrogenic Phenolic GlycosidesChen Huo0Quynh Nhu Nguyen1Akida Alishir2Moon-Jin Ra3Sang-Mi Jung4Jeong-Nam Yu5Hui-Jeong Gwon6Ki Sung Kang7Ki Hyun Kim8School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaCollege of Korean Medicine, Gachon University, Seongnam 13120, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of KoreaHongcheon Institute of Medicinal Herb, Hongcheon-gun 25142, Republic of KoreaHongcheon Institute of Medicinal Herb, Hongcheon-gun 25142, Republic of KoreaNakdonggang National Institute of Biological Resources, Sangju 37242, Republic of KoreaAdvanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup 56212, Republic of KoreaCollege of Korean Medicine, Gachon University, Seongnam 13120, Republic of KoreaSchool of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea<i>Ginkgo biloba</i> L. stands as one of the oldest living tree species, exhibiting a diverse range of biological activities, including antioxidant, neuroprotective, anti-inflammatory, and cardiovascular activities. As part of our ongoing discovery of novel bioactive components from natural sources, we directed our focus toward the investigation of potential bioactive compounds from <i>G. biloba</i> fruit. The profiles of its chemical compounds were examined using a Global Natural Products Social (GNPS)-based molecular networking analysis. Guided by this, we successfully isolated and characterized 11 compounds from <i>G. biloba</i> fruit, including (<i>E</i>)-coniferin (<b>1</b>), syringin (<b>2</b>), 4-hydroxybenzoic acid 4-<i>O</i>-β-D-glucopyranoside (<b>3</b>), vanillic acid 4-<i>O</i>-β-D-glucopyranoside (<b>4</b>), syringic acid 4-<i>O</i>-β-D-glucopyranoside (<b>5</b>), (<i>E</i>)-ferulic acid 4-<i>O</i>-β-D-glucoside (<b>6</b>), (<i>E</i>)-sinapic acid 4-<i>O</i>-β-D-glucopyranoside (<b>7</b>), (1′<i>R</i>,2′<i>S</i>,5′<i>R</i>,8′<i>S</i>,2′<i>Z</i>,4′<i>E</i>)-dihydrophaseic acid 3′-<i>O</i>-β-D-glucopyranoside (<b>8</b>), eucomic acid (<b>9</b>), rutin (<b>10</b>), and laricitrin 3-rutinoside (<b>11</b>). The structural identification was validated through a comprehensive analysis involving nuclear magnetic resonance (NMR) spectroscopic data and LC/MS analyses. All isolated compounds were evaluated using an E-screen assay for their estrogen-like effects in MCF-7 cells. As a result, compounds <b>2</b>, <b>3</b>, <b>4</b>, <b>8</b>, and <b>9</b> promoted cell proliferation in MCF-7 cells, and these effects were mitigated by the ER antagonist, ICI 182,780. In particular, cell proliferation increased most significantly to 140.9 ± 6.5% after treatment with 100 µM of compound <b>2</b>. The mechanism underlying the estrogen-like effect of syringin (<b>2</b>) was evaluated using a Western blot analysis to determine the expression of estrogen receptor α (ERα). We found that syringin (<b>2</b>) induced an increase in the phosphorylation of ERα. Overall, these experimental results suggest that syringin (<b>2</b>) can potentially aid the control of estrogenic activity during menopause.https://www.mdpi.com/2223-7747/12/23/3970<i>Ginkgo biloba</i> fruitsGNPS-guided isolationsyringinestrogen receptorestrogenic activity |
| spellingShingle | Chen Huo Quynh Nhu Nguyen Akida Alishir Moon-Jin Ra Sang-Mi Jung Jeong-Nam Yu Hui-Jeong Gwon Ki Sung Kang Ki Hyun Kim Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from <i>Ginkgo biloba</i> Fruits and the Identification of Estrogenic Phenolic Glycosides Plants <i>Ginkgo biloba</i> fruits GNPS-guided isolation syringin estrogen receptor estrogenic activity |
| title | Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from <i>Ginkgo biloba</i> Fruits and the Identification of Estrogenic Phenolic Glycosides |
| title_full | Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from <i>Ginkgo biloba</i> Fruits and the Identification of Estrogenic Phenolic Glycosides |
| title_fullStr | Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from <i>Ginkgo biloba</i> Fruits and the Identification of Estrogenic Phenolic Glycosides |
| title_full_unstemmed | Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from <i>Ginkgo biloba</i> Fruits and the Identification of Estrogenic Phenolic Glycosides |
| title_short | Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from <i>Ginkgo biloba</i> Fruits and the Identification of Estrogenic Phenolic Glycosides |
| title_sort | global natural products social gnps based molecular networking guided isolation of phenolic compounds from i ginkgo biloba i fruits and the identification of estrogenic phenolic glycosides |
| topic | <i>Ginkgo biloba</i> fruits GNPS-guided isolation syringin estrogen receptor estrogenic activity |
| url | https://www.mdpi.com/2223-7747/12/23/3970 |
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