English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/183085
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:

Title

Transglycosylation products generated by Talaromyces amestolkiae GH3 β-glucosidases: effect of hydroxytyrosol, vanillin and its glucosides on breast cancer cells

AuthorsMéndez-Líter, Juan A.; Tundidor, Isabel; Nieto-Domínguez, Manuel José ; Fernández de Toro, Beatriz; González Santana, Andrés; Eugenio, Laura I. de; Prieto, Alicia ; Asensio, Juan Luis ; Cañada, F. Javier ; Sánchez, Cristina; Martínez, María Jesús
KeywordsTransglycosylation
β-Glucosidases
Glycosyl hydrolases
Hydroxytyrosol
Vanillin
Glucosides
Breast cancer cells
Issue Date31-May-2019
PublisherBioMed Central
CitationMicrobial Cell Factories 18(1): 97 (2019)
Abstract[Background] Transglycosylation represents one of the most promising approaches for obtaining novel glycosides, and plant phenols and polyphenols are emerging as one of the best targets for creating new molecules with enhanced capacities. These compounds can be found in diet and exhibit a wide range of bioactivities, such as antioxidant, antihypertensive, antitumor, neuroprotective and anti-inflammatory, and the eco-friendly synthesis of glycosides from these molecules can be a suitable alternative for increasing their health benefits.
[Results] Transglycosylation experiments were carried out using different GH3 β-glucosidases from the fungus Talaromyces amestolkiae. After a first screening with a wide variety of potential transglycosylation acceptors, mono-glucosylated derivatives of hydroxytyrosol, vanillin alcohol, 4-hydroxybenzyl alcohol, and hydroquinone were detected. The reaction products were analyzed by thin-layer chromatography, high-pressure liquid chromatography, and mass spectrometry. Hydroxytyrosol and vanillyl alcohol were selected as the best options for transglycosylation optimization, with a final conversion yield of 13.8 and 19% of hydroxytyrosol and vanillin glucosides, respectively. NMR analysis confirmed the structures of these compounds. The evaluation of the biological effect of these glucosides using models of breast cancer cells, showed an enhancement in the anti-proliferative capacity of the vanillin derivative, and an improved safety profile of both glucosides.
[Conclusions] GH3 β-glucosidases from T. amestolkiae expressed in P. pastoris were able to transglycosylate a wide variety of acceptors. Between them, phenolic molecules like hydroxytyrosol, vanillin alcohol, 4-hydroxybenzyl alcohol, and hydroquinone were the most suitable for its interesting biological properties. The glycosides of hydroxytyrosol and vanillin were tested, and they improved the biological activities of the original aglycons on breast cancer cells.
Publisher version (URL)https://doi.org/10.1186/s12934-019-1147-4
URIhttp://hdl.handle.net/10261/183085
DOI10.1186/s12934-019-1147-4
ISSN1475-2859
Appears in Collections:(CIB) Artículos
(IQOG) Artículos
Files in This Item:
File Description SizeFormat 
Transglycosylation_products_talaromyces_amestolkiae_GH3_glucosidases.pdf1,83 MBAdobe PDFThumbnail
View/Open
Show full item record
Review this work
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.