Purification, structural elucidation, antioxidant capacity and neuroprotective potential of the main polyphenolic compounds contained in Achyrocline satureioides (Lam) D.C. (Compositae)
| Autor: | David Gonzalez, Marcela Martínez-Busi, Diego Carvalho, Florencia Arredondo, Juan Andrés Abin-Carriquiry, Mauricio A. Vega-Teijido, Federico Dajas, Felicia Rivera, Carolina Echeverry, Alejandra Rodríguez-Haralambides |
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| Rok vydání: | 2019 |
| Předmět: |
Models
Molecular Antioxidant medicine.medical_treatment Clinical Biochemistry Flavonoid Molecular Conformation Pharmaceutical Science Protective Agents 01 natural sciences Biochemistry Neuroprotection Antioxidants Rats Sprague-Dawley chemistry.chemical_compound Tandem Mass Spectrometry Drug Discovery medicine Animals Achyrocline satureioides Molecular Biology Chromatography High Pressure Liquid Density Functional Theory Flavonoids Neurons chemistry.chemical_classification Achyrocline Plants Medicinal Traditional medicine Plant Extracts 010405 organic chemistry Organic Chemistry Polyphenols food and beverages Quinic acid Rats 0104 chemical sciences 010404 medicinal & biomolecular chemistry chemistry Polyphenol Molecular Medicine Quercetin Luteolin |
| Zdroj: | Bioorganic & Medicinal Chemistry. 27:2579-2591 |
| ISSN: | 0968-0896 |
| Popis: | Achyrocline satureioides (Lam) D.C (Compositae) is a native medicinal plant of South America traditionally utilized for its anti-inflammatory, sedative and anti-atherosclerotic properties among others. Neuroprotective effects have been reported in vivo and could be associated to its elevated content of flavonoid aglycones. In the present study we performed the isolation and structure elucidation of the major individual flavonoids of A. satureioides along with the in vitro characterization of their individual antioxidant and neuroprotective properties in order to see their putative relevance for treating neurodegeneration. Exact mass, HPLC-MS/MS and 1H NMR identified dicaffeoyl quinic acid isomers, quercetin, luteolin, isoquercitrin, and 3-O-methylquercetin as the mayor polyphenols. Flavonoids intrinsic redox properties were evaluated in the presence of the endogenous antioxidants GSH and Ascorbate. Density Functional Theory (DFT) molecular modeling and electron density studies showed a theoretical basis for their different redox properties. Finally, in vitro neuroprotective effect of each isolated flavonoid was evaluated against hydrogen peroxide-induced toxicity in a primary neuronal culture paradigm. Our results showed that quercetin was more efficacious than luteolin and isoquercitrin, while 3-O-methylquercetin was unable to afford neuroprotection significantly. This was in accordance with the susceptibility of each flavonoid to be oxidized and to react with GSH. Overall our results shed light on chemical and molecular mechanisms underlying bioactive actions of A. satureioides main flavonoids that could contribute to its neuroprotective effects and support the positive association between the consumption of A. satureioides as a natural dietary source of polyphenols, and beneficial health effect. |
| Databáze: | OpenAIRE |
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