Gardenifolins A–H, Scalemic Neolignans from Gardenia ternifolia: Chiral Resolution, Configurational Assignment, and Cytotoxic Activities against the HeLa Cancer Cell Line
| Autor: | Dieudonné Tshitenge Tshitenge, Doris Feineis, Gerhard Bringmann, Suresh Awale |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Circular dichroism
Magnetic Resonance Spectroscopy Stereochemistry Pharmaceutical Science Apoptosis Stereoisomerism Crystallography X-Ray 010402 general chemistry 01 natural sciences Lignans Analytical Chemistry Stereocenter Drug Discovery Humans Chromatography High Pressure Liquid Pharmacology Molecular Structure 010405 organic chemistry Chemistry Circular Dichroism Organic Chemistry Diastereomer Nuclear magnetic resonance spectroscopy Gardenia Chiral resolution 0104 chemical sciences Complementary and alternative medicine Molecular Medicine Enantiomer Two-dimensional nuclear magnetic resonance spectroscopy HeLa Cells |
| Zdroj: | Journal of Natural Products. 80:1604-1614 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.7b00180 |
| Popis: | From the tropical plant Gardenia ternifolia Schumach. and Thonn. (Rubiaceae), eight stereoisomeric 2,3-dihydrobenzo[b]furan neolignans, named gardenifolins A-H (1a-d and 2a-d), were isolated and fully structurally characterized. Reversed-phase chromatography of a stem bark extract afforded two peaks, viz. mixtures I and II, each one consisting of two diastereomers and their respective enantiomers. They were resolved and stereochemically analyzed by HPLC on a chiral phase coupled to electronic circular dichroism (ECD) spectroscopy, giving single ECD spectra of all eight stereoisomers. The double-bond geometries (E or Z) of the gardenifolins A-H and their relative configurations (cis or trans) at the stereogenic centers C-7 and C-8 in the dihydrofuran ring system were assigned by 1D and 2D NMR methods, in particular, using NOE difference experiments, whereas the absolute configurations of the isolated enantiomers were established by ECD spectroscopy by applying the reversed helicity rule. The individual pure gardenifolin isomers A-H showed the most different cytotoxic effects against the human cancer HeLa cell line, with 1d and 2a displaying the highest activities, with IC |
| Databáze: | OpenAIRE |
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