Fischdiabietane A, an Antitumoral Diterpenoid Dimer Featuring an Unprecedented Carbon Skeleton from Euphorbia fischeriana
| Autor: | Jie-Kun Xu, Jun He, Wen-Wen Lian, Lin-Bo Guo, Hai-Yan Tian, Cong-Yuan Xia, Wei-Ku Zhang, Ying-Xue Shi, Jia Zhang |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Circular dichroism
Euphorbia biology 010405 organic chemistry Stereochemistry Chemistry Dimer Organic Chemistry 010402 general chemistry Ring (chemistry) biology.organism_classification 01 natural sciences Terpenoid 0104 chemical sciences chemistry.chemical_compound biology.protein Molecule Nonane Polymerase |
| Zdroj: | The Journal of Organic Chemistry. 86:5894-5900 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.1c00305 |
| Popis: | Fischdiabietane A (1), a novel asymmetric diterpenoid dimer with a unique nonacyclic 6/6/6/5/7/6/6/6/6 ring system possessing unprecedented 2-oxaspiro[4.5]decane-1-one and 2-oxabicyclo[3.2.2]nonane frameworks in D/E/F rings, was isolated from the roots of Euphorbia fischeriana. Its structure was determined by spectroscopic techniques, electronic circular dichroism calculations, and X-ray diffraction experiments. Notably, 1 is the first abietane-type [4 + 2] Diels-Alder dimer identified from nature. The IC50 of 1 against T47D cells was about sixfold higher than that of cisplatin (the positive control). Furthermore, 1 induced apoptosis in T47D cells through the activation of caspase-3 and the degradation of poly(ADP-ribose) polymerase. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|