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

Org Lett

State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.

Published: July 2017

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 O-labeling experiment. Compound 2 could inhibit Wnt pathway in a dose- and time-dependent manner.

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http://dx.doi.org/10.1021/acs.orglett.7b01813DOI Listing

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