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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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Published in: | Organic letters 2018-05, Vol.20 (10), p.3124-3127 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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). |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.8b01215 |