Méndez Líter, Juan AntonioTundidor, IsabelNieto Domínguez, ManuelFernández de Toro, BeatrizGonzález Santana, AndrésEugenio, Laura Isabel dePrieto, AliciaAsensio, Juan LuisCañada, Francisco JavierSánchez García, María CristinaMartínez, María Jesús2024-04-042024-04-042019-05-31Méndez-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: PMC6544938.1475-285910.1186/s12934-019-1147-4https://hdl.handle.net/20.500.14352/102728Background 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.engAttribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/journal articlehttps://microbialcellfactories.biomedcentral.com/articles/10.1186/s12934-019-1147-4open access577.1618.19-006Transglycosylationβ-GlucosidasesGlycosyl hydrolasesHydroxytyrosolVanillinGlucosidesBreast cancer cellsBioquímica (Biología)Oncología2403 Bioquímica3201.01 Oncología