Oddioside A, a New Phenolic Glycoside Isolated from the Fruits of <i>Morus alba</i> (Mulberry), Protects TNF-α-Induced Human Dermal Fibroblast Damage
In our preliminary study, a hot water extract from the fruits of <i>Morus alba</i> (mulberry) inhibited the secretion of metalloproteinase-1 (MMP-1) against tumor necrosis factor-α (TNF-α)-stimulated human dermal fibroblasts (HDFs), and therefore we researched its active compounds. In th...
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MDPI AG
2022-09-01
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| Series: | Antioxidants |
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| Online Access: | https://www.mdpi.com/2076-3921/11/10/1894 |
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| author | Kang Sub Kim Ranhee Kim So-Ri Son Ki Sung Kang Dae Sik Jang Sullim Lee |
| author_facet | Kang Sub Kim Ranhee Kim So-Ri Son Ki Sung Kang Dae Sik Jang Sullim Lee |
| author_sort | Kang Sub Kim |
| collection | DOAJ |
| description | In our preliminary study, a hot water extract from the fruits of <i>Morus alba</i> (mulberry) inhibited the secretion of metalloproteinase-1 (MMP-1) against tumor necrosis factor-α (TNF-α)-stimulated human dermal fibroblasts (HDFs), and therefore we researched its active compounds. In the present study, a new phenolic glycoside (oddioside A, <b>1</b>) and 21 known compounds (<b>2</b>−<b>22</b>) were isolated from the hot water extract from the fruits of <i>M. alba</i> by repeated chromatography. The chemical structure of the new compound <b>1</b> was elucidated by its spectroscopic data (1<span style="font-variant: small-caps;">D</span>− and 2<span style="font-variant: small-caps;">D</span>−NMR and HRMS) measurement and by acidic hydrolysis. The presence of sargentodoside E (<b>2</b>), eugenyl glucoside (<b>6</b>), 2-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-4,6-dihydroxybenzaldehyde <b>(7</b>), 7<i>S</i>,8<i>R</i>-erythro-7,9,9’-trihydroxy-3,3’-dimethoxy-8-<i>O</i>-4’-neolignan-4-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>11</b>), pinoresinol-4-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>12</b>), taxifolin-7-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>20</b>), and pinellic acid (<b>21</b>) were reported from <i>M. alba</i> for the first time in this study. The new compound oddioside A (<b>1</b>) suppressed the secretion of MMP-1 and increased collagen in TNF-α-stimulated HDFs. In addition, the phosphorylation of mitogen-activated protein kinases (MAPKs) was inhibited by oddioside A. In conclusion, the extract from fruits of <i>M. alba</i> and its constituent oddioside A may be a potential agent to prevent inflammation-related skin aging and other skin disorders. |
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| spelling | doaj.art-bd0cbcc0942c42129f249d1f353a84e62023-11-23T22:37:28ZengMDPI AGAntioxidants2076-39212022-09-011110189410.3390/antiox11101894Oddioside A, a New Phenolic Glycoside Isolated from the Fruits of <i>Morus alba</i> (Mulberry), Protects TNF-α-Induced Human Dermal Fibroblast DamageKang Sub Kim0Ranhee Kim1So-Ri Son2Ki Sung Kang3Dae Sik Jang4Sullim Lee5College of Korean Medicine, Gachon University, Seongnam 13120, KoreaDepartment of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaDepartment of Biomedical and Pharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaCollege of Korean Medicine, Gachon University, Seongnam 13120, KoreaDepartment of Biomedical and Pharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaDepartment of Life Science, College of Bio-Nano Technology, Gachon University, Seongnam 13120, KoreaIn our preliminary study, a hot water extract from the fruits of <i>Morus alba</i> (mulberry) inhibited the secretion of metalloproteinase-1 (MMP-1) against tumor necrosis factor-α (TNF-α)-stimulated human dermal fibroblasts (HDFs), and therefore we researched its active compounds. In the present study, a new phenolic glycoside (oddioside A, <b>1</b>) and 21 known compounds (<b>2</b>−<b>22</b>) were isolated from the hot water extract from the fruits of <i>M. alba</i> by repeated chromatography. The chemical structure of the new compound <b>1</b> was elucidated by its spectroscopic data (1<span style="font-variant: small-caps;">D</span>− and 2<span style="font-variant: small-caps;">D</span>−NMR and HRMS) measurement and by acidic hydrolysis. The presence of sargentodoside E (<b>2</b>), eugenyl glucoside (<b>6</b>), 2-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranosyl-4,6-dihydroxybenzaldehyde <b>(7</b>), 7<i>S</i>,8<i>R</i>-erythro-7,9,9’-trihydroxy-3,3’-dimethoxy-8-<i>O</i>-4’-neolignan-4-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>11</b>), pinoresinol-4-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>12</b>), taxifolin-7-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>20</b>), and pinellic acid (<b>21</b>) were reported from <i>M. alba</i> for the first time in this study. The new compound oddioside A (<b>1</b>) suppressed the secretion of MMP-1 and increased collagen in TNF-α-stimulated HDFs. In addition, the phosphorylation of mitogen-activated protein kinases (MAPKs) was inhibited by oddioside A. In conclusion, the extract from fruits of <i>M. alba</i> and its constituent oddioside A may be a potential agent to prevent inflammation-related skin aging and other skin disorders.https://www.mdpi.com/2076-3921/11/10/1894human dermal fibroblaststumor necrosis factor-αskin damage<i>Morus alba</i>phenolic glycoside |
| spellingShingle | Kang Sub Kim Ranhee Kim So-Ri Son Ki Sung Kang Dae Sik Jang Sullim Lee Oddioside A, a New Phenolic Glycoside Isolated from the Fruits of <i>Morus alba</i> (Mulberry), Protects TNF-α-Induced Human Dermal Fibroblast Damage Antioxidants human dermal fibroblasts tumor necrosis factor-α skin damage <i>Morus alba</i> phenolic glycoside |
| title | Oddioside A, a New Phenolic Glycoside Isolated from the Fruits of <i>Morus alba</i> (Mulberry), Protects TNF-α-Induced Human Dermal Fibroblast Damage |
| title_full | Oddioside A, a New Phenolic Glycoside Isolated from the Fruits of <i>Morus alba</i> (Mulberry), Protects TNF-α-Induced Human Dermal Fibroblast Damage |
| title_fullStr | Oddioside A, a New Phenolic Glycoside Isolated from the Fruits of <i>Morus alba</i> (Mulberry), Protects TNF-α-Induced Human Dermal Fibroblast Damage |
| title_full_unstemmed | Oddioside A, a New Phenolic Glycoside Isolated from the Fruits of <i>Morus alba</i> (Mulberry), Protects TNF-α-Induced Human Dermal Fibroblast Damage |
| title_short | Oddioside A, a New Phenolic Glycoside Isolated from the Fruits of <i>Morus alba</i> (Mulberry), Protects TNF-α-Induced Human Dermal Fibroblast Damage |
| title_sort | oddioside a a new phenolic glycoside isolated from the fruits of i morus alba i mulberry protects tnf α induced human dermal fibroblast damage |
| topic | human dermal fibroblasts tumor necrosis factor-α skin damage <i>Morus alba</i> phenolic glycoside |
| url | https://www.mdpi.com/2076-3921/11/10/1894 |
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