6,7-seco-ent-kauranoids derived from oridonin as potential anticancer agents
Structurally unique 6,7-seco-ent-kaurenes, which are widely distributed in the genus Isodon, have attracted considerable attention because of their antitumor activities. Previously, a convenient conversion of commercially available oridonin (1) to 6,7-seco-ent-kaurenes was developed. Herein, several...
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| Format: | Article |
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American Chemical Society
2017
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| Online Access: | https://eprints.nottingham.ac.uk/46459/ |
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| author | Xu, Shengtao Yao, Hong Hu, Mei Li, Dahong Zhu, Zheying Xie, Weijia Yao, Hequan Wu, Liang Chen, Zhe-Sheng Xu, Jinyi |
| author_facet | Xu, Shengtao Yao, Hong Hu, Mei Li, Dahong Zhu, Zheying Xie, Weijia Yao, Hequan Wu, Liang Chen, Zhe-Sheng Xu, Jinyi |
| author_sort | Xu, Shengtao |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | Structurally unique 6,7-seco-ent-kaurenes, which are widely distributed in the genus Isodon, have attracted considerable attention because of their antitumor activities. Previously, a convenient conversion of commercially available oridonin (1) to 6,7-seco-ent-kaurenes was developed. Herein, several novel spiro-lactone-type ent-kaurene derivatives bearing various substituents at the C-1 and C-14 positions were further designed and synthesized from the natural product oridonin. Moreover, a number of seven-membered C-ring-expanded 6,7-seco-ent-kaurenes were also identified for the first time. It was observed that most of the spiro-lactone-type ent-kaurenes tested markedly inhibited the proliferation of cancer cells, with an IC50 value as low as 0.55 μM. An investigation on its mechanism of action showed that the representative compound 7b affected the cell cycle and induced apoptosis at a low micromolar level in MCF-7 human breast cancer cells. Furthermore, compound 7b inhibited liver tumor growth in an in vivo mouse model and exhibited no observable toxic effects. Collectively, the results warrant further preclinical investigations of these spiro-lactone-type ent-kaurenes as potential novel anticancer agents. |
| first_indexed | 2025-11-14T20:02:11Z |
| format | Article |
| id | nottingham-46459 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T20:02:11Z |
| publishDate | 2017 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-464592020-05-04T19:06:07Z https://eprints.nottingham.ac.uk/46459/ 6,7-seco-ent-kauranoids derived from oridonin as potential anticancer agents Xu, Shengtao Yao, Hong Hu, Mei Li, Dahong Zhu, Zheying Xie, Weijia Yao, Hequan Wu, Liang Chen, Zhe-Sheng Xu, Jinyi Structurally unique 6,7-seco-ent-kaurenes, which are widely distributed in the genus Isodon, have attracted considerable attention because of their antitumor activities. Previously, a convenient conversion of commercially available oridonin (1) to 6,7-seco-ent-kaurenes was developed. Herein, several novel spiro-lactone-type ent-kaurene derivatives bearing various substituents at the C-1 and C-14 positions were further designed and synthesized from the natural product oridonin. Moreover, a number of seven-membered C-ring-expanded 6,7-seco-ent-kaurenes were also identified for the first time. It was observed that most of the spiro-lactone-type ent-kaurenes tested markedly inhibited the proliferation of cancer cells, with an IC50 value as low as 0.55 μM. An investigation on its mechanism of action showed that the representative compound 7b affected the cell cycle and induced apoptosis at a low micromolar level in MCF-7 human breast cancer cells. Furthermore, compound 7b inhibited liver tumor growth in an in vivo mouse model and exhibited no observable toxic effects. Collectively, the results warrant further preclinical investigations of these spiro-lactone-type ent-kaurenes as potential novel anticancer agents. American Chemical Society 2017-09-13 Article PeerReviewed Xu, Shengtao, Yao, Hong, Hu, Mei, Li, Dahong, Zhu, Zheying, Xie, Weijia, Yao, Hequan, Wu, Liang, Chen, Zhe-Sheng and Xu, Jinyi (2017) 6,7-seco-ent-kauranoids derived from oridonin as potential anticancer agents. Journal of Natural Products . ISSN 1520-6025 http://pubs.acs.org/doi/abs/10.1021/acs.jnatprod.7b00057 doi:10.1021/acs.jnatprod.7b00057 doi:10.1021/acs.jnatprod.7b00057 |
| spellingShingle | Xu, Shengtao Yao, Hong Hu, Mei Li, Dahong Zhu, Zheying Xie, Weijia Yao, Hequan Wu, Liang Chen, Zhe-Sheng Xu, Jinyi 6,7-seco-ent-kauranoids derived from oridonin as potential anticancer agents |
| title | 6,7-seco-ent-kauranoids derived from oridonin as potential
anticancer agents |
| title_full | 6,7-seco-ent-kauranoids derived from oridonin as potential
anticancer agents |
| title_fullStr | 6,7-seco-ent-kauranoids derived from oridonin as potential
anticancer agents |
| title_full_unstemmed | 6,7-seco-ent-kauranoids derived from oridonin as potential
anticancer agents |
| title_short | 6,7-seco-ent-kauranoids derived from oridonin as potential
anticancer agents |
| title_sort | 6,7-seco-ent-kauranoids derived from oridonin as potential
anticancer agents |
| url | https://eprints.nottingham.ac.uk/46459/ https://eprints.nottingham.ac.uk/46459/ https://eprints.nottingham.ac.uk/46459/ |