| Synthesis of hupehenols A, B, and E from protopanaxadiol | |
Shao, Li-Dong1; Xu, Jun1,2 ; Li, Xiao-Nian1; Zhang, Zhi-Jun1,2; Shi, Xin1,2; Ren, Jian1,2; He, Juan1; Zhao, Yu1; Leng, Ying3; Xia, Chengfeng1; Zhao, Qin-Shi1
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| 2016 | |
| 发表期刊 | RSC ADVANCES
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| 卷号 | 6期号:42页码:35792-35803 |
| 摘要 | Hupehenols A-E (3-7) are bioactive octanordammarane triterpenoids, among which hupehenols B (4) and E (7) are the most potent and selective human 11 beta-hydroxysteroid dehydrogenase type 1 (11 beta-HSD1) inhibitors (IC50 = 15 and 34 nM, respectively). Herein, the hupehenols were synthesized from protopanaxadiol, the main component of Panax notoginseng. The different synthetic attempts resulted in the stereoselective synthesis of hupehenols A, B, and E for further biological exploration. Notable features of the synthesis included a regioselective epoxide-opening reaction, regioselective acetylation, and a late-stage stereoselective oxa-Michael addition. Semi-synthetic derivatization of these natural products led to the determination of their absolute configurations, a better understanding of their inherent reactivity patterns, and the required C-17 configuration for murine 11 beta-HSD1 inhibition. These studies provide the basis for the synthesis of 11 beta-HSD1 inhibitors as potential targets for the treatment of type 2 diabetes. |
| DOI | 10.1039/c6ra04236h |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000374349600077 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.kib.ac.cn/handle/151853/26217 |
| 专题 | 植物化学与西部植物资源持续利用国家重点实验室 |
| 作者单位 | 1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Shao, Li-Dong,Xu, Jun,Li, Xiao-Nian,et al. Synthesis of hupehenols A, B, and E from protopanaxadiol[J]. RSC ADVANCES,2016,6(42):35792-35803. |
| APA | Shao, Li-Dong.,Xu, Jun.,Li, Xiao-Nian.,Zhang, Zhi-Jun.,Shi, Xin.,...&Zhao, Qin-Shi.(2016).Synthesis of hupehenols A, B, and E from protopanaxadiol.RSC ADVANCES,6(42),35792-35803. |
| MLA | Shao, Li-Dong,et al."Synthesis of hupehenols A, B, and E from protopanaxadiol".RSC ADVANCES 6.42(2016):35792-35803. |
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