Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts
Abstract Since procyanidins (oligomeric catechin or epicatechin) were reported to exhibit health benefits, much attention has been paid to the synthesis of these compounds, especially those that are longer than trimers. In the present study, syntheses of cinnamtannin A3 (epicatechin pentamer), A4 (e...
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2017
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oai:doaj.org-article:2a09a7e1216a434a93e4c8b5322c482c2021-12-02T16:06:33ZEpicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts10.1038/s41598-017-08059-x2045-2322https://doaj.org/article/2a09a7e1216a434a93e4c8b5322c482c2017-08-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-08059-xhttps://doaj.org/toc/2045-2322Abstract Since procyanidins (oligomeric catechin or epicatechin) were reported to exhibit health benefits, much attention has been paid to the synthesis of these compounds, especially those that are longer than trimers. In the present study, syntheses of cinnamtannin A3 (epicatechin pentamer), A4 (epicatechin hexamer), catechin tetramer, pentamer, arecatannin A2 (epicatechin-epicatechin-epicatechin-catechin) and A3 (epicatechin-epicatechin-epicatechin-epicatechin-catechin) were achieved. The key reaction was a Lewis acid mediated equimolar condensation. The antitumor effects of these synthesized compounds against a human prostate cancer cell line (PC-3) were investigated. Among the tested compounds, cinnamtannin A3, A4 and arecatannin A3, which possess epicatechin oligomers longer than tetramers as the basic scaffold, showed significant activities for suppression of cell growth, invasion and FABP5 (fatty acid-binding protein 5) gene expression. Effects on cell cycle distribution showed that cell cycle arrest in the G2 phase was induced. Furthermore, these epicatechin oligomers suppressed significantly the expression of the cancer-promoting gene, FABP5, which is related to cell proliferation and metastasis in various cancer cells. Interestingly, the suppressive activities were associated with the degree of oligomerization of epicatechin. Thus, synthetic studies clearly demonstrate that epicatechin oligomers longer than trimers have significant anti-tumorigenic activities, but not the catechin counterparts.Kohki TakanashiManato SudaKiriko MatsumotoChisato IshiharaKazuya TodaKoichiro KawaguchiShogo SengaNarumi KobayashiMikihiro IchikawaMiyuki KatohYasunao HattoriSei-ichi KawaharaKoji UmezawaHiroshi FujiiHidefumi MakabeNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-13 (2017) |
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| collection |
DOAJ |
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| topic |
Medicine R Science Q |
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Medicine R Science Q Kohki Takanashi Manato Suda Kiriko Matsumoto Chisato Ishihara Kazuya Toda Koichiro Kawaguchi Shogo Senga Narumi Kobayashi Mikihiro Ichikawa Miyuki Katoh Yasunao Hattori Sei-ichi Kawahara Koji Umezawa Hiroshi Fujii Hidefumi Makabe Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts |
| description |
Abstract Since procyanidins (oligomeric catechin or epicatechin) were reported to exhibit health benefits, much attention has been paid to the synthesis of these compounds, especially those that are longer than trimers. In the present study, syntheses of cinnamtannin A3 (epicatechin pentamer), A4 (epicatechin hexamer), catechin tetramer, pentamer, arecatannin A2 (epicatechin-epicatechin-epicatechin-catechin) and A3 (epicatechin-epicatechin-epicatechin-epicatechin-catechin) were achieved. The key reaction was a Lewis acid mediated equimolar condensation. The antitumor effects of these synthesized compounds against a human prostate cancer cell line (PC-3) were investigated. Among the tested compounds, cinnamtannin A3, A4 and arecatannin A3, which possess epicatechin oligomers longer than tetramers as the basic scaffold, showed significant activities for suppression of cell growth, invasion and FABP5 (fatty acid-binding protein 5) gene expression. Effects on cell cycle distribution showed that cell cycle arrest in the G2 phase was induced. Furthermore, these epicatechin oligomers suppressed significantly the expression of the cancer-promoting gene, FABP5, which is related to cell proliferation and metastasis in various cancer cells. Interestingly, the suppressive activities were associated with the degree of oligomerization of epicatechin. Thus, synthetic studies clearly demonstrate that epicatechin oligomers longer than trimers have significant anti-tumorigenic activities, but not the catechin counterparts. |
| format |
article |
| author |
Kohki Takanashi Manato Suda Kiriko Matsumoto Chisato Ishihara Kazuya Toda Koichiro Kawaguchi Shogo Senga Narumi Kobayashi Mikihiro Ichikawa Miyuki Katoh Yasunao Hattori Sei-ichi Kawahara Koji Umezawa Hiroshi Fujii Hidefumi Makabe |
| author_facet |
Kohki Takanashi Manato Suda Kiriko Matsumoto Chisato Ishihara Kazuya Toda Koichiro Kawaguchi Shogo Senga Narumi Kobayashi Mikihiro Ichikawa Miyuki Katoh Yasunao Hattori Sei-ichi Kawahara Koji Umezawa Hiroshi Fujii Hidefumi Makabe |
| author_sort |
Kohki Takanashi |
| title |
Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts |
| title_short |
Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts |
| title_full |
Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts |
| title_fullStr |
Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts |
| title_full_unstemmed |
Epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts |
| title_sort |
epicatechin oligomers longer than trimers have anti-cancer activities, but not the catechin counterparts |
| publisher |
Nature Portfolio |
| publishDate |
2017 |
| url |
https://doaj.org/article/2a09a7e1216a434a93e4c8b5322c482c |
| work_keys_str_mv |
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1718384951909416960 |