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Cytotoxic Properties of C(17) Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells

Although C(17) polyacetylenes from Panax ginseng 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(17) polyacetylenes from P. ginseng against ovarian cancer cell...

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Autores principales: Kim, Ranhee, Son, So-Ri, Lee, Na-Kyung, Kim, Ji-Young, An, Gami, Choi, Jung-Hye, Jang, Dae Sik
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9607587/
https://www.ncbi.nlm.nih.gov/pubmed/36296616
http://dx.doi.org/10.3390/molecules27207027
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author Kim, Ranhee
Son, So-Ri
Lee, Na-Kyung
Kim, Ji-Young
An, Gami
Choi, Jung-Hye
Jang, Dae Sik
author_facet Kim, Ranhee
Son, So-Ri
Lee, Na-Kyung
Kim, Ji-Young
An, Gami
Choi, Jung-Hye
Jang, Dae Sik
author_sort Kim, Ranhee
collection PubMed
description Although C(17) polyacetylenes from Panax ginseng 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(17) polyacetylenes from P. ginseng against ovarian cancer cell lines. Four unreported (1–4) and fifteen known (5–19) C(17) polyacetylenes were obtained from the roots of P. ginseng 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 (3S,8S,9R,10R)-(-)-heptadeca-9,10-epoxy-4,6-diyne-3,8-diyl diacetate (1), (3S,8S,9R,10R)-(−)-heptadeca-1-en-9,10-epoxy-4,6-diyne-3,8-diyl diacetate (2), (−)-haptadeca-9,10-epoxy-8-methoxy-4,6-diyne-3,11-diol (3), and (3R,9R,10R)-(+)-3-acetoxy-9,10-dihydroxyheptadeca-1-en-4,6-diyne (4), 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 (15) exhibited the most remarkable cytotoxic effects on both human ovarian cancer cells A2780 (IC(50) value of 7.60 μM) and SKOV3 (IC(50) value of 27.53 μM). Therefore, C(17) polyacetylenes derived from P. ginseng may warrant further investigation for their therapeutic potential in epithelial ovarian cancer.
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spelling pubmed-96075872022-10-28 Cytotoxic Properties of C(17) Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells Kim, Ranhee Son, So-Ri Lee, Na-Kyung Kim, Ji-Young An, Gami Choi, Jung-Hye Jang, Dae Sik Molecules Article Although C(17) polyacetylenes from Panax ginseng 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(17) polyacetylenes from P. ginseng against ovarian cancer cell lines. Four unreported (1–4) and fifteen known (5–19) C(17) polyacetylenes were obtained from the roots of P. ginseng 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 (3S,8S,9R,10R)-(-)-heptadeca-9,10-epoxy-4,6-diyne-3,8-diyl diacetate (1), (3S,8S,9R,10R)-(−)-heptadeca-1-en-9,10-epoxy-4,6-diyne-3,8-diyl diacetate (2), (−)-haptadeca-9,10-epoxy-8-methoxy-4,6-diyne-3,11-diol (3), and (3R,9R,10R)-(+)-3-acetoxy-9,10-dihydroxyheptadeca-1-en-4,6-diyne (4), 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 (15) exhibited the most remarkable cytotoxic effects on both human ovarian cancer cells A2780 (IC(50) value of 7.60 μM) and SKOV3 (IC(50) value of 27.53 μM). Therefore, C(17) polyacetylenes derived from P. ginseng may warrant further investigation for their therapeutic potential in epithelial ovarian cancer. MDPI 2022-10-18 /pmc/articles/PMC9607587/ /pubmed/36296616 http://dx.doi.org/10.3390/molecules27207027 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kim, Ranhee
Son, So-Ri
Lee, Na-Kyung
Kim, Ji-Young
An, Gami
Choi, Jung-Hye
Jang, Dae Sik
Cytotoxic Properties of C(17) Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells
title Cytotoxic Properties of C(17) Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells
title_full Cytotoxic Properties of C(17) Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells
title_fullStr Cytotoxic Properties of C(17) Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells
title_full_unstemmed Cytotoxic Properties of C(17) Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells
title_short Cytotoxic Properties of C(17) Polyacetylenes from the Fresh Roots of Panax ginseng on Human Epithelial Ovarian Cancer Cells
title_sort cytotoxic properties of c(17) polyacetylenes from the fresh roots of panax ginseng on human epithelial ovarian cancer cells
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9607587/
https://www.ncbi.nlm.nih.gov/pubmed/36296616
http://dx.doi.org/10.3390/molecules27207027
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