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Heliojatrones A and B, Two Jatrophane-Derived Diterpenoids with a 5/10 Fused-Ring Skeleton from Euphorbia helioscopia: Structural Elucidation and Biomimetic Conversion

Heliojatrones A and B (1 and 2), two jatrophane-derived diterpenoids with an unprecedented trans-bicyclo­[8.3.0]­tridecane core, were isolated from the whole plants of Euphorbia helioscopia. Their structures and absolute configurations were unequivocally determined by a combination of spectroscopic...

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Bibliographic Details
Published in:Organic letters 2018-05, Vol.20 (10), p.3124-3127
Main Authors: Mai, Zhen-Peng, Ni, Gang, Liu, Yan-Fei, Li, Li, Li, Jia-Yuan, Yu, De-Quan
Format: Article
Language:English
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Summary:Heliojatrones A and B (1 and 2), two jatrophane-derived diterpenoids with an unprecedented trans-bicyclo­[8.3.0]­tridecane core, were isolated from the whole plants of Euphorbia helioscopia. Their structures and absolute configurations were unequivocally determined by a combination of spectroscopic data, electronic circular dichroism calculations, biomimetic conversion, and X-ray diffraction analyses. Their plausible biosynthetic pathways were also proposed. Compounds 1 and 2 were biomimetically synthesized from 3 and 4 through a photochemical rearrangement reaction of β,γ-unsaturated ketone, respectively. Compound 2 showed significant P-glycoprotein inhibitory activity compared with the positive control (cyclosporine A).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01215