2026-06-27T10:10:55Zhttps://docta.ucm.es/rest/oai/request
oai:docta.ucm.es:20.500.14352/1027282025-03-18T12:09:44Zcom_20.500.14352_14col_20.500.14352_15
Docta Complutense author Méndez Líter, Juan Antonio author Tundidor, Isabel author Nieto Domínguez, Manuel author Fernández de Toro, Beatriz author González Santana, Andrés author Eugenio, Laura Isabel de author Prieto, Alicia author Asensio, Juan Luis author Cañada, Francisco Javier author Sánchez García, María Cristina author Martínez, María Jesús 2024-04-04T18:06:30Z 2024-04-04T18:06:30Z 2019-05-31 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. 1475-2859 10.1186/s12934-019-1147-4 https://hdl.handle.net/20.500.14352/102728 https://microbialcellfactories.biomedcentral.com/articles/10.1186/s12934-019-1147-4 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. eng Attribution 4.0 International Transglycosylation products generated by Talaromyces amestolkiae GH3 β-glucosidases: effect of hydroxytyrosol, vanillin and its glucosides on breast cancer cells journal article 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URL https://docta.ucm.es/bitstreams/0a9121c6-3147-454d-a833-baab93bf6469/download File MD5 3efbb57a12251bc5b05582cca68a6a29 1877408 application/pdf 2019_Méndez-Liter_Microbial Cell Factories.pdf URL https://docta.ucm.es/bitstreams/8f4d2928-d4fc-43be-92c7-fdeb3da43b24/download File MD5 3a42446c0892536f2e80fa8a4bc1dcb0 58023 text/plain 2019_Méndez-Liter_Microbial Cell Factories.pdf.txt