Cytotoxic Properties of C<sub>17</sub> Polyacetylenes from the Fresh Roots of <i>Panax ginseng</i> on Human Epithelial Ovarian Cancer Cells
Although C<sub>17</sub> polyacetylenes from <i>Panax ginseng</i> exhibit cytotoxic properties against various tumor cells, there have been few experiments on epithelial ovarian carcinoma cells. This study aimed to investigate the cytotoxic effects of C<sub>17</sub>...
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MDPI AG
2022-10-01
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| author | Ranhee Kim So-Ri Son Na-Kyung Lee Ji-Young Kim Gami An Jung-Hye Choi Dae Sik Jang |
| author_facet | Ranhee Kim So-Ri Son Na-Kyung Lee Ji-Young Kim Gami An Jung-Hye Choi Dae Sik Jang |
| author_sort | Ranhee Kim |
| collection | DOAJ |
| description | Although C<sub>17</sub> polyacetylenes from <i>Panax ginseng</i> exhibit cytotoxic properties against various tumor cells, there have been few experiments on epithelial ovarian carcinoma cells. This study aimed to investigate the cytotoxic effects of C<sub>17</sub> polyacetylenes from <i>P. ginseng</i> against ovarian cancer cell lines. Four unreported (<b>1</b>–<b>4</b>) and fifteen known (<b>5</b>–<b>19</b>) C<sub>17</sub> polyacetylenes were obtained from the roots of <i>P</i>. <i>ginseng</i> using repeated chromatography (open column, MPLC, and preparative HPLC). The chemical structures of all the compounds were determined by analyzing their spectroscopic data (NMR, IR, and optical rotation) and HR-MS. The structures of new polyacetylenes were elucidated as (3<i>S</i>,8<i>S</i>,9<i>R</i>,10<i>R</i>)-(-)-heptadeca-9,10-epoxy-4,6-diyne-3,8-diyl diacetate (<b>1</b>), (3<i>S</i>,8<i>S</i>,9<i>R</i>,10<i>R</i>)-(−)-heptadeca-1-en-9,10-epoxy-4,6-diyne-3,8-diyl diacetate (<b>2</b>), (−)-haptadeca-9,10-epoxy-8-methoxy-4,6-diyne-3,11-diol (<b>3</b>), and (3<i>R</i>,9<i>R</i>,10<i>R</i>)-(+)-3-acetoxy-9,10-dihydroxyheptadeca-1-en-4,6-diyne (<b>4</b>), named ginsenoynes O, P, and Q, and 3-acetyl panaxytriol, respectively. Subsequently, in vitro experiments on A2780 and SKOV3 human epithelial ovarian carcinoma cells were performed to assess the cytotoxic properties of the isolates. Among the isolates, panaquinquecol 4 (<b>15</b>) exhibited the most remarkable cytotoxic effects on both human ovarian cancer cells A2780 (IC<sub>50</sub> value of 7.60 μM) and SKOV3 (IC<sub>50</sub> value of 27.53 μM). Therefore, C<sub>17</sub> polyacetylenes derived from <i>P</i>. <i>ginseng</i> may warrant further investigation for their therapeutic potential in epithelial ovarian cancer. |
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| spelling | doaj.art-eed65877ea844552a696e8d1bf935b7c2023-11-24T01:35:52ZengMDPI AGMolecules1420-30492022-10-012720702710.3390/molecules27207027Cytotoxic Properties of C<sub>17</sub> Polyacetylenes from the Fresh Roots of <i>Panax ginseng</i> on Human Epithelial Ovarian Cancer CellsRanhee Kim0So-Ri Son1Na-Kyung Lee2Ji-Young Kim3Gami An4Jung-Hye Choi5Dae Sik Jang6Department 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, KoreaDepartment of Biomedical and Pharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaDepartment of Biomedical and Pharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaDepartment of Biomedical and Pharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaDepartment of Biomedical and Pharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaDepartment of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, KoreaAlthough C<sub>17</sub> polyacetylenes from <i>Panax ginseng</i> exhibit cytotoxic properties against various tumor cells, there have been few experiments on epithelial ovarian carcinoma cells. This study aimed to investigate the cytotoxic effects of C<sub>17</sub> polyacetylenes from <i>P. ginseng</i> against ovarian cancer cell lines. Four unreported (<b>1</b>–<b>4</b>) and fifteen known (<b>5</b>–<b>19</b>) C<sub>17</sub> polyacetylenes were obtained from the roots of <i>P</i>. <i>ginseng</i> using repeated chromatography (open column, MPLC, and preparative HPLC). The chemical structures of all the compounds were determined by analyzing their spectroscopic data (NMR, IR, and optical rotation) and HR-MS. The structures of new polyacetylenes were elucidated as (3<i>S</i>,8<i>S</i>,9<i>R</i>,10<i>R</i>)-(-)-heptadeca-9,10-epoxy-4,6-diyne-3,8-diyl diacetate (<b>1</b>), (3<i>S</i>,8<i>S</i>,9<i>R</i>,10<i>R</i>)-(−)-heptadeca-1-en-9,10-epoxy-4,6-diyne-3,8-diyl diacetate (<b>2</b>), (−)-haptadeca-9,10-epoxy-8-methoxy-4,6-diyne-3,11-diol (<b>3</b>), and (3<i>R</i>,9<i>R</i>,10<i>R</i>)-(+)-3-acetoxy-9,10-dihydroxyheptadeca-1-en-4,6-diyne (<b>4</b>), named ginsenoynes O, P, and Q, and 3-acetyl panaxytriol, respectively. Subsequently, in vitro experiments on A2780 and SKOV3 human epithelial ovarian carcinoma cells were performed to assess the cytotoxic properties of the isolates. Among the isolates, panaquinquecol 4 (<b>15</b>) exhibited the most remarkable cytotoxic effects on both human ovarian cancer cells A2780 (IC<sub>50</sub> value of 7.60 μM) and SKOV3 (IC<sub>50</sub> value of 27.53 μM). Therefore, C<sub>17</sub> polyacetylenes derived from <i>P</i>. <i>ginseng</i> may warrant further investigation for their therapeutic potential in epithelial ovarian cancer.https://www.mdpi.com/1420-3049/27/20/7027cytotoxicityhuman ovarian cancer<i>Panax ginseng</i>polyacetylenes |
| spellingShingle | Ranhee Kim So-Ri Son Na-Kyung Lee Ji-Young Kim Gami An Jung-Hye Choi Dae Sik Jang Cytotoxic Properties of C<sub>17</sub> Polyacetylenes from the Fresh Roots of <i>Panax ginseng</i> on Human Epithelial Ovarian Cancer Cells Molecules cytotoxicity human ovarian cancer <i>Panax ginseng</i> polyacetylenes |
| title | Cytotoxic Properties of C<sub>17</sub> Polyacetylenes from the Fresh Roots of <i>Panax ginseng</i> on Human Epithelial Ovarian Cancer Cells |
| title_full | Cytotoxic Properties of C<sub>17</sub> Polyacetylenes from the Fresh Roots of <i>Panax ginseng</i> on Human Epithelial Ovarian Cancer Cells |
| title_fullStr | Cytotoxic Properties of C<sub>17</sub> Polyacetylenes from the Fresh Roots of <i>Panax ginseng</i> on Human Epithelial Ovarian Cancer Cells |
| title_full_unstemmed | Cytotoxic Properties of C<sub>17</sub> Polyacetylenes from the Fresh Roots of <i>Panax ginseng</i> on Human Epithelial Ovarian Cancer Cells |
| title_short | Cytotoxic Properties of C<sub>17</sub> Polyacetylenes from the Fresh Roots of <i>Panax ginseng</i> on Human Epithelial Ovarian Cancer Cells |
| title_sort | cytotoxic properties of c sub 17 sub polyacetylenes from the fresh roots of i panax ginseng i on human epithelial ovarian cancer cells |
| topic | cytotoxicity human ovarian cancer <i>Panax ginseng</i> polyacetylenes |
| url | https://www.mdpi.com/1420-3049/27/20/7027 |
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