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
Source PublicationRSC ADVANCES
AbstractHupehenols 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.
Indexed BySCI
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000374349600077
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Cited Times:5[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Affiliation1.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
Recommended Citation
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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