Influence of the concentration of Quercus sideroxyla leaf infusions on the extraction of phenolic compounds, antioxidant and anti-inflammatory activity
DOI:
https://doi.org/10.59741/eb5fkj20Keywords:
Oak infusions, polyphenols, antioxidant, anti-inflammatoryAbstract
Quercus sideroxyla infusion has been shown to have important biotherapeutic effects, especially antioxidant and anti-inflammatory effects due to its content of polyphenolic compounds. Among the main variables for the extraction of bioactive compounds by infusing in water stands out the solute-solvent ratio. The purpose of this study was to analyze the influence of the percentage of leaves on the phenolic content extracted and its antioxidant and anti-inflammatory potential effects. To this end, infusions of Quercus 1 at 10% (w/v) of leaves were obtained, which were analyzed for the content of phenols and total flavonoids, phenolic profiling for phenolic acids, flavonoids and hydrolyzable tannins was monitored by means of UPLC-ESI--MS/MS. Antioxidant activity was determined using FRAP, ABTS, ORAC, and DPPH, as well as anti-inflammatory activity using an erythrocyte membrane stabilization assay. The variation in the percentage of leaves to produce the infusions promoted a progressive increase in the extraction of phenols to a percentage of 7% (w/v), subsequently no significant differences were observed, but a nominal decrease in the content was. The phenolic profiling was also affected, favoring a higher concentration of oak leaves and the extraction of hydrolyzable tannins, especially vascalagin and penducalagin 1 and 2, which contributed to increasing the antioxidant activity for the trapping of peroxide radicals and reduction of the ferric ion. Anti-inflammatory activity was also increased, although it appears to be more associated with a synergistic effect between epicatechin gallate and other polyphenols.
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Al‐Sayed, E., & Abdel‐Daim, M. M. (2018). Analgesic and anti‐inflammatory activities of epicatechin gallate from Bauhinia hookeri. Drug Development Research, 79(4), 157-164. https://doi.org/10.1002/ddr.21430 DOI: https://doi.org/10.1002/ddr.21430
Álvarez, S. A., Rocha‐Guzmán, N. E., Sánchez-Burgos, J. A., Gallegos‐Infante, J. A., Moreno‐Jiménez, M. R., González‐Laredo, R. F., & Solís-González, S. (2023). Analysis of antioxidant constituents of filtering infusions from oak (Quercus sideroxyla bonpl. and Quercus eduardii trel.) and yerbaniz (Tagetes lucida (Sweet) voss) as monoamine oxidase inhibitors. Molecules, 28(13), 5167. https://doi.org/10.3390/molecules28135167 DOI: https://doi.org/10.3390/molecules28135167
Astill, C., Birch, M. R., Dacombe, C., Humphrey, P. G., & Martin, P. T. (2001). Factors affecting the caffeine and polyphenol contents of black and green tea infusions. Journal of Agricultural and Food Chemistry, 49(11), 5340–5347. https://doi.org/10.1021/jf010759+ DOI: https://doi.org/10.1021/jf010759+
Benzie, I. F., & Choi, S. W. (2014). Antioxidant in food: Content, measurement, significance, action, cautions, caveats, and research needs. En Advances in food and nutrition research.,71, 1-53. https://doi.org/10.1016/b978-0-12-800270-4.00001-8 DOI: https://doi.org/10.1016/B978-0-12-800270-4.00001-8
Bobo, G., Davidov‐Pardo, G., Arroqui, C., Vı́rseda, P., Marín-Arroyo, M. R., & Boronat-Navarro, M. (2014). Intra-laboratory validation of microplate methods for total phenolic content and antioxidant activity on polyphenolic extracts, and comparison with conventional spectrophotometric methods. Journal of the Science of Food and Agriculture, 95(1), 204-209. https://doi.org/10.1002/jsfa.6706 DOI: https://doi.org/10.1002/jsfa.6706
Çavuldak, Ö. A., Vural, N., Akay, M. A., & Anlı, R. E. (2019). Optimization of ultrasound‐assisted water extraction conditions for the extraction of phenolic compounds from black mulberry leaves (Morus nigra l.). Journal of Food Process Engineering, 42(5). https://doi.org/10.1111/jfpe.13132 DOI: https://doi.org/10.1111/jfpe.13132
Díaz-Rivas, J.O.; González-Laredo, R.F.; Chávez-Simental, J.A.; Montoya-Ayón, J.B.; Moreno-Jiménez, M.R.; Gallegos-Infante, J.A.; Rocha-Guzmán, N.E. (2018) Comprehensive PDA-ESI-QqQ of Buddleja scordioides plants elicited with salicylic acid. J. Chem. 218, 4536970 DOI: https://doi.org/10.1155/2018/4536970
Dudonné, S., Vitrac, X., Coutière, P., Woillez, M., & Mérillon, J. (2009). Comparative study of antioxidant properties and total phenolic content of 30 plant extracts of industrial interest using DPPH, ABTS, FRAP, SOD, and ORAC assays. Journal of Agricultural and Food Chemistry, 57(5), 1768-1774. https://doi.org/10.1021/jf803011r DOI: https://doi.org/10.1021/jf803011r
Evtyugin, D. D., Magina, S., & Evtuguin, D. V. (2020). Recent Advances in the Production and Applications of Ellagic Acid and Its Derivatives. A Review. Molecules, 25(12), 2745. https://doi.org/10.3390/molecules25122745 DOI: https://doi.org/10.3390/molecules25122745
Gamboa‐Gómez, C. I., Simental‐Mendía, L. E., González‐Laredo, R. F., Alcantar-Orozco, E. J., Monserrat-Juarez, V. H., Ramírez-España, J. C., Gallegos‐Infante, J. A., Moreno‐Jiménez, M. R., & Rocha‐Guzmán, N. E. (2017). In vitro and in vivo assessment of anti-hyperglycemic and antioxidant effects of oak leaves (Quercus convallata and Quercus arizonica) infusions and fermented beverages. Food Research International, 102, 690-699. https://doi.org/10.1016/j.foodres.2017.09.040 DOI: https://doi.org/10.1016/j.foodres.2017.09.040
Kowalska, J., Marzec, A., Domian, E., Galus, S., Ciurzyńska, A., Brzezińska, R., & Kowalska, H. (2021). Influence of Tea Brewing Parameters on the Antioxidant Potential of Infusions and Extracts Depending on the Degree of Processing of the Leaves of Camellia sinensis. Molecules, 26(16), 4773. https://doi.org/10.3390/molecules26164773 DOI: https://doi.org/10.3390/molecules26164773
Koleckar, V., Kubikova, K., Rehakova, Z., Kuca, K., Jun, D., Jahodar, L., & Opletal, L. (2008). Condensed and Hydrolysable Tannins as Antioxidants Influencing the Health. Mini-Reviews In Medicinal Chemistry, 8(5), 436-447. https://doi.org/10.2174/138955708784223486 DOI: https://doi.org/10.2174/138955708784223486
Mendez-Encinas, M. A., Valencia, D., Ortega-García, J., Carvajal-Millan, E., Díaz-Ríos, J. C., Mendez-Pfeiffer, P., Soto-Bracamontes, C. M., Garibay-Escobar, A., Alday, E., & Velazquez, C. (2023b). Anti-Inflammatory Potential of Seasonal Sonoran Propolis Extracts and Some of Their Main Constituents. Molecules, 28(11), 4496. https://doi.org/10.3390/molecules28114496 DOI: https://doi.org/10.3390/molecules28114496
Molino, S., Lerma-Aguilera, A., Jiménez-Hernández, N., Gosalbes, M. J., Rufián-Henares, J. Á., & Francino, M. P. (2021). Enrichment of Food With Tannin Extracts Promotes Healthy Changes in the Human Gut Microbiota. Frontiers In Microbiology, 12. https://doi.org/10.3389/fmicb.2021.625782 DOI: https://doi.org/10.3389/fmicb.2021.625782
Moreno‐Jiménez, M. R., Trujillo-Esquivel, F., Gallegos‐Corona, M. A., Reynoso‐Camacho, R., González‐Laredo, R. F., Gallegos‐Infante, J. A., Rocha‐Guzmán, N. E., & Ramos-Gómez, M. (2015). Antioxidant, anti-inflammatory and anticarcinogenic activities of edible red oak (Quercus spp.) infusions in rat colon carcinogenesis induced by 1,2-dimethylhydrazine. Food and Chemical Toxicology, 80, 144-153. https://doi.org/10.1016/j.fct.2015.03.011 DOI: https://doi.org/10.1016/j.fct.2015.03.011
Nájera-Luna, J. A., Vargas-Antonio, Z., Méndez-González, J., & De Jesús Graciano-Luna, J. (2005). Propiedades físicas y mecánicas de la madera en Quercus laeta Liemb. de El Salto, Durango. Redalyc.org. https://www.redalyc.org/articulo.oa?id=46110307 DOI: https://doi.org/10.35197/rx.01.03.2005.07.JN
Oliveira, P. A., Medeiros‐Fonseca, B., Nóbrega, C., Alvarado, A., Pires, M. J., Vala, H., Barros, A., & Faustino-Rocha, A. I. (2023b). Quercus spp. extract as a Promising preventive or therapeutic strategy for cancer: A Systematic review. Molecular Medicine Reports, 28(3). https://doi.org/10.3892/mmr.2023.13062 DOI: https://doi.org/10.3892/mmr.2023.13062
Osman, N. I., Sidik, N. J., Awal, A., Adam, N. A. M., & Rezali, N. I. (2016). In vitro xanthine oxidase and albumin denaturation inhibition assay of barringtonia racemosa L. And total phenolic content analysis for potential anti-infl ammatory use in gouty arthritis. Journal of Intercultural Ethnopharmacology, 5(4), 343–349. https://doi.org/10.5455/jice.20160731025522 DOI: https://doi.org/10.5455/jice.20160731025522
Ou, B., Hampsch-Woodill, M., & Prior, R. L. (2001). Development and Validation of an Improved Oxygen Radical Absorbance Capacity Assay Using Fluorescein as the Fluorescent Probe. Journal Of Agricultural And Food Chemistry, 49(10), 4619-4626. https://doi.org/10.1021/jf010586o DOI: https://doi.org/10.1021/jf010586o
Piazza, S., Martinelli, G., Fumagalli, M., Pozzoli, C., Maranta, N., Giavarini, F., Colombo, L., Nicotra, G., Vicentini, S. F., Genova, F., De Fabiani, E., Sangiovanni, E., & Dell’Agli, M. (2023). Ellagitannins from Castanea sativa Mill. leaf extracts impair H. pylori viability and Infection-Induced inflammation in human gastric epithelial cells. Nutrients, 15(6), 1504. https://doi.org/10.3390/nu15061504 DOI: https://doi.org/10.3390/nu15061504
Qi, W., Qi, W., Xiong, D., & Long, M. (2022). Quercetin: Its Antioxidant Mechanism, Antibacterial Properties and Potential Application in Prevention and Control of Toxipathy. Molecules, 27(19), 6545. https://doi.org/10.3390/molecules27196545 DOI: https://doi.org/10.3390/molecules27196545
Re, R., Pellegrini, N., Proteggente, A. R., Pannala, A. S., Yang, M., & Rice‐Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology And Medicine, 26(9-10), 1231-1237. https://doi.org/10.1016/s0891-5849(98)00315-3 DOI: https://doi.org/10.1016/S0891-5849(98)00315-3
Rocha‐Guzmán, N. E., Gallegos‐Infante, J. A., González‐Laredo, R. F., Reynoso‐Camacho, R., Ramos-Gómez, M., García-Gasca, T., Rodríguez-Muñoz, M. E., Guzmán-Maldonado, S. H., Medina‐Torres, L., & Lujan-García, B. A. (2009). Antioxidant activity and genotoxic effect on HELA cells of phenolic compounds from infusions of Quercus resinosa leaves. Food Chemistry, 115(4), 1320-1325. https://doi.org/10.1016/j.foodchem.2009.01.050 DOI: https://doi.org/10.1016/j.foodchem.2009.01.050
Rocha‐Guzmán, N. E., Medina-Medrano, J. R., Gallegos‐Infante, J. A., González‐Laredo, R. F., Ramos-Gómez, M., Reynoso‐Camacho, R., Guzmán‐Maldonado, H., & González‐Herrera, S. M. (2012). Chemical evaluation, antioxidant capacity, and consumer acceptance of several oak infusions. Journal of Food Science, 77(2). https://doi.org/10.1111/j.1750-3841.2011.02524.x DOI: https://doi.org/10.1111/j.1750-3841.2011.02524.x
Ross, H. A., McDougall, G. J., & Stewart, D. (2007). Antiproliferative activity is predominantly associated with ellagitannins in raspberry extracts. Phytochemistry, 68(2), 218-228. https://doi.org/10.1016/j.phytochem.2006.10.014 DOI: https://doi.org/10.1016/j.phytochem.2006.10.014
Samuel, B. B., Esho, B. A., Akinwunmi, K. F., & Oluyemi, W. M. (2021). Membrane stabilization and inhibition of protein denaturation as mechanisms of the Anti-Inflammatory activity of some plant species. DOAJ (DOAJ: Directory of Open Access Journals). https://doi.org/10.30476/tips.2021.93160.1118
Sembiring, E. N., Elya, B., & Sauriasari, R. (2017). Phytochemical screening, total flavonoid and total phenolic content and antioxidant activity of different parts of Caesalpinia Bonduc (L.) Roxb. Pharmacognosy Journal, 10(1), 123-127. https://doi.org/10.5530/pj.2018.1.22 DOI: https://doi.org/10.5530/pj.2018.1.22
Statista. (2024). México: valor de la producción forestal de encino 2005-2018. https://es.statista.com/estadisticas/593140/valor-de-la-produccion-de-encino-mexico/
Thakur, M. D., Sheth, N. R., & Raval, M. K. (2020). Assessment of In vitro Anti-inflammatory Activity of Ginger and Diclofenac sodium combination. International Journal Of Pharmaceutical Sciences And Drug Research, 442-447. https://doi.org/10.25004/ijpsdr.2020.120503 DOI: https://doi.org/10.25004/IJPSDR.2020.120503
Vuong, Q. V., Golding, J. M., Stathopoulos, C. E., Nguyen, M. H., & Roach, P. D. (2011). Optimizing conditions for the extraction of catechins from green tea using hot water. Journal of Separation Science, 34(21), 3099-3106. https://doi.org/10.1002/jssc.201000863 DOI: https://doi.org/10.1002/jssc.201000863
Wang, H., & Cao, Z. (2014). Anti-inflammatory Effects of (-)-Epicatechin in Lipopolysaccharide-Stimulated Raw 264.7 Macrophages. Tropical Journal Of Pharmaceutical Research, 13(9), 1415. https://doi.org/10.4314/tjpr.v13i9.6 DOI: https://doi.org/10.4314/tjpr.v13i9.6
Wang, S., Li, Y., Meng, X., Chen, S., Huang, D., Xia, Y., & Zhu, S. (2021). Antioxidant activities of chlorogenic acid derivatives with different acyl donor chain lengths and their stabilities during in vitro simulated gastrointestinal digestion. Food Chemistry, 357, 129904. https://doi.org/10.1016/j.foodchem.2021.129904 DOI: https://doi.org/10.1016/j.foodchem.2021.129904
World Health Organization. (2009). Benefits and risks of the use of chlorine-containing disinfectants in food production and food processing : report of a joint FAO/WHO expert meeting, Ann Arbor, MI, USA, 27-30 May 2008. https://iris.who.int/handle/10665/44250
Yesmin, S., Paul, A., Naz, T., Rahman, A. B. M. A., Akhter, S. F., Wahed, M. I. I., Emran, T. B., & Siddiqui, S. A. (2020). Membrane stabilization as a mechanism of the anti-inflammatory activity of ethanolic root extract of Choi (Piper chaba). Clinical Phytoscience, 6(1). https://doi.org/10.1186/s40816-020-00207-7 DOI: https://doi.org/10.1186/s40816-020-00207-7
Yoshida, T., Amakura, Y., & Yoshimura, M. (2010). Structural Features and Biological Properties of Ellagitannins in Some Plant Families of the Order Myrtales. International Journal Of Molecular Sciences, 11(1), 79-106. https://doi.org/10.3390/ijms11010079 DOI: https://doi.org/10.3390/ijms11010079
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Copyright (c) 2025 Carlos Alonso Salas Ramírez, Martha Rocío Moreno-Jiménez, Nuria Elizabeth Rocha-Guzmán, Rubén Francisco González-Laredo, José Alberto Gallegos-Infante, Manuel Efraín González-Mercado, Karen Marlenne Herrera-Rocha

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