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

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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… Click to show full abstract

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.

Keywords: tigliane diterpenoids; new carbon; carbon skeletons; euphorbia dracunculoides

Journal Title: Organic letters
Year Published: 2017

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