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Org Lett. 2017 Jul 21;19(14):3911-3914. doi: 10.1021/acs.orglett.7b01813. Epub 2017 Jul 13.

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

Author information

1
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.
2
University of Chinese Academy of Sciences , Beijing 100049, China.
3
College of Chemistry and Chemical Engineering, Yunnan Normal University , Kunming 650500, China.

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.

PMID:
28703597
DOI:
10.1021/acs.orglett.7b01813
[Indexed for MEDLINE]

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