Xylopiana A, a Dimeric Guaiane with a Case-Shaped Core from Xylopia vielana: Structural Elucidation and Biomimetic Conversion
| Autor: | Ming-Hua Yang, Xiao-Bing Wang, Ya-Long Zhang, Jun Luo, Ling-Yi Kong, Yong Yin, Lin Wu, Jian-Guang Luo, Xu-Wei Zhou |
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| Rok vydání: | 2017 |
| Předmět: |
Circular dichroism
Molecular Structure biology 010405 organic chemistry Chemistry Stereochemistry Circular Dichroism Organic Chemistry Crystallography X-Ray 010402 general chemistry biology.organism_classification Xylopia 01 natural sciences Biochemistry 0104 chemical sciences Sesquiterpenes Guaiane Crystallography Biomimetics Chemical conversion Molecule Physical and Theoretical Chemistry Xylopia vielana |
| Zdroj: | Organic Letters. 19:3013-3016 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b01276 |
| Popis: | Xylopiana A (1), a dimeric guaiane with an unprecedented pentacyclo[5.2.1.01,2.04,5′.05,4′]decane-3,2′-dione core, and three biosynthetically related intermediates, compounds 2–4, were isolated from the leaves of Xylopia vielana. Their structures and absolute configurations were determined by a combination of spectroscopic data, X-ray crystallography, electronic circular dichroism calculations, and chemical conversion. The structure of known vielanin A was revised to be compound 3. Compound 4 exerted a 3.7-fold potentiation effect on doxorubicin susceptibility at the tested concentration of 10 μM. |
| Databáze: | OpenAIRE |
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