Organic Letters
Organic Letters
5 years ago

Natural and Semisynthetic Tigliane Diterpenoids with New Carbon Skeletons from Euphorbia dracunculoides as a Wnt Signaling Pathway Inhibitor

Natural and Semisynthetic Tigliane Diterpenoids with New Carbon Skeletons from Euphorbia dracunculoides as a Wnt Signaling Pathway Inhibitor
Yijun Yan, Li Wang, Sheng-Xiong Huang, Yong Zhao, Yikao Hu, Zijun Xiong, Ling-Mei Kong, Jun Deng, Jing Yang, Xiao-Nian Li, Jianying Luo, Jianping Huang, Yan Li
Euphordraculoates A (1) and B (2), featuring tigliane diterpenoids with two new carbon skeletons, were characterized as metabolites of Euphorbia dracunculoides and semisynthetic products, respectively. Their structures were determined by spectroscopic analyses and X-ray crystallography. The respective biosynthetic and chemical formation mechanisms for 1 and 2 from a known tigliane 3 was proposed. The detailed decarbonization mechanism from 3 to 2 was further explored by 18O-labeling experiment. Compound 2 could inhibit Wnt pathway in a dose- and time-dependent manner.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01813

DOI: 10.1021/acs.orglett.7b01813

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