Academic Journal
أعرض في EDS

Synthesis and Characterization of a Novel Resveratrol Xylobioside Obtained Using a Mutagenic Variant of a GH10 Endoxylanase

التفاصيل البيبلوغرافية
العنوان: Synthesis and Characterization of a Novel Resveratrol Xylobioside Obtained Using a Mutagenic Variant of a GH10 Endoxylanase
المؤلفون: Pozo-Rodríguez, Ana, Méndez-Líter, Juan A., García-Villalba, Rocío, Beltrán, David, Calviño, Eva, GONZALEZ SANTANA, ANDRES, Eugenio, Laura I. de, Cañada, F. Javier, Prieto, Alicia, Barriuso, Jorge, Tomás-Barberán, Francisco, Jesús Martínez, María
المساهمون: Ministerio de Ciencia e Innovación (España), Agencia Estatal de Investigación (España), Fondo Europeo de Desarrollo Regional (FEDER), Comunidad de Madrid, Fundación General CSIC, Instituto de Salud Carlos III, CSIC - Unidad de Recursos de Información Científica para la Investigación (URICI)
بيانات النشر: Multidisciplinary Digital Publishing Institute
سنة النشر: 2022
المجموعة: Digital.CSIC (Consejo Superior de Investigaciones Científicas / Spanish National Research Council)
مصطلحات موضوعية: Antioxidants, colonic fermentation, fungal enzyme, glycoconjugates, glycoside hydrolases, glycosynthase, polyphenols, solubility, xylobiose
الوصف: Resveratrol is a natural polyphenol with antioxidant activity and numerous health benefits. However, in vivo application of this compound is still a challenge due to its poor aqueous solubility and rapid metabolism, which leads to an extremely low bioavailability in the target tissues. In this work, rXynSOS-E236G glycosynthase, designed from a GH10 endoxylanase of the fungus Talaromyces amestolkiae, was used to glycosylate resveratrol by using xylobiosyl-fluoride as a sugar donor. The major product from this reaction was identified by NMR as 3-O-ꞵ-d-xylobiosyl resveratrol, together with other glycosides produced in a lower amount as 4′-O-ꞵ-d-xylobiosyl resveratrol and 3-O-ꞵ-d-xylotetraosyl resveratrol. The application of response surface methodology made it possible to optimize the reaction, producing 35% of 3-O-ꞵ-d-xylobiosyl resveratrol. Since other minor glycosides are obtained in addition to this compound, the transformation of the phenolic substrate amounted to 70%. Xylobiosylation decreased the antioxidant capacity of resveratrol by 2.21-fold, but, in return, produced a staggering 4,866-fold improvement in solubility, facilitating the delivery of large amounts of the molecule and its transit to the colon. A preliminary study has also shown that the colonic microbiota is capable of releasing resveratrol from 3-O-ꞵ-d-xylobiosyl resveratrol. These results support the potential of mutagenic variants of glycosyl hydrolases to synthesize highly soluble resveratrol glycosides, which could, in turn, improve the bioavailability and bioactive properties of this polyphenol. ; The authors acknowledge Francisco Plou (ICP-CSIC) for kindly providing the resveratrol and María Dolores Frutos for helping in the sample extraction and HPLC-DAD-MS analyses. Ana Pozo-Rodríguez thanks the Spanish Government for her FPU19/04192 fellowship. The authors acknowledge the IBISBA1.0 (H2020 730976) project and the SusPlast-CSIC Interdisciplinary Platform for their support. The authors thank the Mass Spectrometry UCM CAI and NMR and GC ...
نوع الوثيقة: article in journal/newspaper
اللغة: English
تدمد: 2076-3921
Relation: #PLACEHOLDER_PARENT_METADATA_VALUE#; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-093683-B-I00/ES/GLICOSIL HIDROLASAS Y OTRAS ENZIMAS AUXILIARIES PARA LA PRODUCCION DE COMPUESTOS DE VALOR AÑADIDO/; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RTI2018-094751-B-C22/ES/RMN Y RECONOCIMIENTO MOLECULAR DE CARBOHIDRATOS: LECTINAS, ENZIMAS Y ACIDOS NUCLEICOS/; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-114210RB-I00/ES/CONSORCIOS MICROBIANOS PARA LA DEGRADACION DE PLASTICOS CONVENCIONALES/; info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021-123781OB-C22/ES/DESCIFRANDO EL CODIGO DEL RECONOCIMIENTO MOLECULAR DE GLICANOS. ASPECTOS BASICOS Y APLICACIONES EN SALUD/; info:eu-repo/grantAgreement/CAM/Producción sostenible y simbiosis industrial en la Comunidad de Madrid/RETOPROSOST-2-CM P2018/EMT-4459; Publisher's version; https://doi.org/10.3390/antiox12010085; Sí; Antioxidants, 12(1), 85: 1-16 (2022); http://hdl.handle.net/10261/288672
DOI: 10.3390/antiox12010085
الاتاحة: http://hdl.handle.net/10261/288672
https://doi.org/10.3390/antiox12010085
Rights: open
رقم الانضمام: edsbas.CEB6F5A2
قاعدة البيانات: BASE
الوصف
تدمد:20763921
DOI:10.3390/antiox12010085