Enzymatic Synthesis of Resveratrol α-Glycosides from β-Cyclodextrin-Resveratrol Complex in Water
| Autor: | Florent Allais, Eduardo Gazaneo Barboza, Jean-Hugues Renault, Thomas Marié, Audrey Gratia, Eric Courot, Jane Hubert, Andreia R. S. Teixeira, Gaëlle Willig, Alexis Kotland |
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| Přispěvatelé: | Agro-Biotechnologies Industrielles (ABI), AgroParisTech, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Résistance Induite et Bioprotection des Plantes - EA 4707 (RIBP), Université de Reims Champagne-Ardenne (URCA)-SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
Antioxidant Bioconversion General Chemical Engineering medicine.medical_treatment Resveratrol 01 natural sciences 7. Clean energy 03 medical and health sciences chemistry.chemical_compound [CHIM.ANAL]Chemical Sciences/Analytical chemistry medicine Environmental Chemistry Organic chemistry chemistry.chemical_classification Natural product Cyclodextrin [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Renewable Energy Sustainability and the Environment Glycoside [CHIM.CATA]Chemical Sciences/Catalysis General Chemistry Bioproduction 0104 chemical sciences Bioavailability 030104 developmental biology chemistry |
| Zdroj: | ACS Sustainable Chemistry & Engineering ACS Sustainable Chemistry & Engineering, American Chemical Society, 2018, 6 (4), pp.5370-5380. ⟨10.1021/acssuschemeng.8b00176⟩ |
| ISSN: | 2168-0485 |
| DOI: | 10.1021/acssuschemeng.8b00176 |
| Popis: | International audience; Although resveratrol (3,5,4′-trihydroxy-stilbene) is one of the most studied natural product because of its biological properties such as antioxidant or anticancer, its low water solubility and stability (influenced by pH, light and increased temperature), as well as its propensity to oligomerize, limit its bioavailability and applications in nutraceutic, cosmetics or pharmaceutical industries. Besides, resveratrol production at the multigram scale through vine cell culture is limited by the tedious extraction of pure resveratrol from the bioconversion medium due to its complexation by cyclodextrins, the latter being used as elicitors in the bioproduction process. In this work, we have been able to overcome all these drawbacks by performing a single organic solvent-free enzymatic α-glycosylation directly from the β-cyclodextrin-resveratrol complex in water using β-cyclodextrin as glycoside-donor. The combined effects of five parameters (CGTase amount, cyclodextrin amount, cyclodextrin/resveratrol ratio, pH, and temperature) were studied by design of experiments (DoE) to maximize the glycosylation yield. The optimal setting point of parameters was obtained by response surface methodology (RSM). After optimization, an efficient α-glycosylation was performed being obtained 35% of molar yield. The major glycosides—two monoglycosides: 3-O-α-d-glucosyl-resveratrol and 4′-O-α-d-glucosyl-resveratrol and two diglycosides: 3-O-α-d-maltosyl-resveratrol and 4′-O-α-d-maltosyl-resveratrol—were characterized using a hyphenated liquid chromatography-solid phase extraction-nuclear magnetic resonance system, then separated and purified using centrifugal partition chromatography (CPC). Their antiradical properties, as well as that of their crude mixture, were evaluated through DPPH analysis. Results confirmed that the position 4′–OH is the best position for the glycosylation to maintain the highest antiradical properties. |
| Databáze: | OpenAIRE |
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