RT Journal Article
T1 Transglycosylation products generated by Talaromyces amestolkiae GH3 β-glucosidases: effect of hydroxytyrosol, vanillin and its glucosides on breast cancer cells
A1 Méndez Líter, Juan Antonio
A1 Tundidor, Isabel
A1 Nieto Domínguez, Manuel
A1 Fernández de Toro, Beatriz
A1 González Santana, Andrés
A1 Eugenio, Laura Isabel de
A1 Prieto, Alicia
A1 Asensio, Juan Luis
A1 Cañada, Francisco Javier
A1 Sánchez García, María Cristina
A1 Martínez, María Jesús
AB BackgroundTransglycosylation 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.ResultsTransglycosylation 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.ConclusionsGH3 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.
PB BioMed Central
SN 1475-2859
YR 2019
FD 2019-05-31
LK https://hdl.handle.net/20.500.14352/102728
UL https://hdl.handle.net/20.500.14352/102728
LA eng
NO Méndez-Líter JA, Tundidor I, Nieto-Domínguez M, de Toro BF, González Santana A, de Eugenio LI, Prieto A, Asensio JL, Cañada FJ, Sánchez C, Martínez MJ. Transglycosylation products generated by Talaromyces amestolkiae GH3 β-glucosidases: effect of hydroxytyrosol, vanillin and its glucosides on breast cancer cells. Microb Cell Fact. 2019 May 31;18(1):97. doi: 10.1186/s12934-019-1147-4. PMID: 31151435; PMCID: PMC6544938.
NO Ministerio de Economía y Competitividad (MINECO)
NO Comunidad de Madrid
DS Docta Complutense
RD 10 abr 2025