Perfil químico y bioprospección de granos de cacao analizados por espectrometría de masas con ionización por paper spray
DOI:
https://doi.org/10.33448/rsd-v9i8.6882Palabras clave:
PS-MS; Theobroma cacao; Compuestos bioactivos; 20-Hidroxiecdisona; Clovamida.Resumen
Productos derivados del cacao han recibido cada vez más reconocimiento y relevancia tanto por parte de los consumidores como de los productores. Los granos de cacao son los principales componentes responsables de gran parte de la cadena agroindustrial del cacao que actualmente se valora por las propiedades bioactivas que se encuentran en sus subproductos, lo que crea un gran interés en explorar los potenciales del cacao. Trabajos que objetivan evaluar los compuestos en semillas de la fruta emplean HPLC, UHPLC y LC-MS. Este trabajo empleó la espectrometría de masas por paper spray (PS-MS) como método para caracterizar y bioprospectar el perfil químico de granos de cacao (Theobroma cacao) de la variedad forrasteiro cultivada en el estado brasileño de Pará. Extractos metanólicos se prepararon con muestras de granos de cacao y se evaluaron en modos de ionización negativa y positiva. En el modo de ionización positiva, fue posible identificar 11 compuestos, que comprenden las clases metilxantinas (18.2%), fenilpropanoides (9.1%), esteroides (27.3%) y flavonoides (45.5%), mientras que en el modo de ionización negativa, fue posible identificar 55 compuestos entre ácidos hidroxibenzoicos (16.4%), fenilpropanoides (20.0%), flavonoides (52.7%), azúcares y glucósidos (10.9%). PS-MS demostró ser eficaz para la evaluación de muestras de granos de cacao, identificando un total de 66 compuestos. Las propiedades bioactivas atribuidas al cacao se confirmaron en muestras analizadas por los compuestos identificados a través de PS-MS al tiempo que indicaban la calidad de materia prima y describían su perfil químico, contribuyendo a una mayor comprensión de sus atributos.
Citas
Ágoston, C., Urbán, R., Rigó, A., Griffiths, M. D., & Demetrovics, Z. (2019). Morningness-eveningness and caffeine consumption: A largescale path-analysis study. Chronobiology International, 36(9), 1301–1309. https://doi.org/10.1080/07420528.2019.1624372
Ajaha, A., Bouayad, N., Aarab, A., & Rharrabe, K. (2019). Effect of 20-hydroxyecdysone, a phytoecdysteroid, on development, digestive, and detoxification enzyme activities of tribolium castaneum (Coleoptera: Tenebrionidae). Journal of Insect Science, 19(5). https://doi.org/10.1093/jisesa/iez097
Algharrawi, K. H. R., Summers, R. M., & Subramanian, M. (2017). Production of theobromine by N-demethylation of caffeine using metabolically engineered E. coli. Biocatalysis and Agricultural Biotechnology, 11, 153–160. https://doi.org/10.1016/j.bcab.2017.06.014
Bacanli, M., Başaran, A. A., & Başaran, N. (2015). The antioxidant and antigenotoxic properties of citrus phenolics limonene and naringin. Food and Chemical Toxicology, 81, 160–170. https://doi.org/10.1016/j.fct.2015.04.015
Ballard, C. R., & Maróstica, M. R. (2018). Health Benefits of Flavonoids. In Bioactive Compounds: Health Benefits and Potential Applications. https://doi.org/10.1016/B978-0-12-814774-0.00010-4
Barnaba, C., Nardin, T., Pierotti, A., Malacarne, M., & Larcher, R. (2017). Targeted and untargeted characterisation of free and glycosylated simple phenols in cocoa beans using high resolution-tandem mass spectrometry (Q-Orbitrap). Journal of Chromatography A, 1480, 41–49. https://doi.org/10.1016/j.chroma.2016.12.022
Barros, H. R. de M., García-Villalba, R., Tomás-Barberán, F. A., & Genovese, M. I. (2016). Evaluation of the distribution and metabolism of polyphenols derived from cupuassu (Theobroma grandiflorum) in mice gastrointestinal tract by UPLC-ESI-QTOF. Journal of Functional Foods, 22, 477–489. https://doi.org/10.1016/j.jff.2016.02.009
Cádiz-Gurrea, M. L., Lozano-Sanchez, J., Contreras-Gámez, M., Legeai-Mallet, L., Fernández-Arroyo, S., & Segura-Carretero, A. (2014). Isolation, comprehensive characterization and antioxidant activities of Theobroma cacao extract. Journal of Functional Foods, 10, 485–498. https://doi.org/10.1016/j.jff.2014.07.016
Calderón, A. I., Wright, B. J., Hurst, W. J., & Van Breemen, R. B. (2009). Screening antioxidants using LC-MS: Case study with cocoa. Journal of Agricultural and Food Chemistry, 57(13), 5693–5699. https://doi.org/10.1021/jf9014203
Chen, X. Y., Zhou, J., Luo, L. P., Han, B., Li, F., Chen, J. Y., … Yu, X. P. (2015). Black Rice Anthocyanins Suppress Metastasis of Breast Cancer Cells by Targeting RAS/RAF/MAPK Pathway. BioMed Research International, 2015. https://doi.org/10.1155/2015/414250
Clifford, M. N., & Scalbert, A. (2000). Ellagitannins - Nature, occurrence and dietary burden. Journal of the Science of Food and Agriculture, 80(7), 1118–1125. https://doi.org/10.1002/(SICI)1097-0010(20000515)80:7<1118::AID-JSFA570>3.0.CO;2-9
Cova, I., Leta, V., Mariani, C., Pantoni, L., & Pomati, S. (2019). Exploring cocoa properties: is theobromine a cognitive modulator? Psychopharmacology, 236(2), 561–572. https://doi.org/10.1007/s00213-019-5172-0
D’Souza, R. N., Grimbs, S., Behrends, B., Bernaert, H., Ullrich, M. S., & Kuhnert, N. (2017). Origin-based polyphenolic fingerprinting of Theobroma cacao in unfermented and fermented beans. Food Research International, 99(May), 550–559. https://doi.org/10.1016/j.foodres.2017.06.007
Da Rosa, H. S., De Camargo, V. B., Camargo, G., Garcia, C. V., Fuentefria, A. M., & Mendez, A. S. L. (2015). Ecdysteroids in Sida tuberculata R.E. Fries (Malvaceae): Chemical composition by LC-ESI-MS and selective anti-Candida krusei activity. Food Chemistry, 182, 193–199. https://doi.org/10.1016/j.foodchem.2015.02.144
da Silva, J. P., do S. Costa, M., Campina, F. F., Bezerra, C. F., de Freitas, T. S., Sousa, A. K., … Rocha, J. E. (2020). Evaluation of chelating and cytoprotective activity of vanillin against the toxic action of mercuric chloride as an alternative for phytoremediation. Environmental Geochemistry and Health, 0123456789(Tino 2010). https://doi.org/10.1007/s10653-020-00538-x
Dinan, L., Mamadalieva, N. Z., & Lafont, R. (2020). Dietary Phytoecdysteroids. In Handbook of Dietary Phytochemicals. https://doi.org/10.1007/978-981-13-1745-3_35-1
Ding, Y., Dai, X., Jiang, Y., Zhang, Z., Bao, L., Li, Y., … Li, Y. (2013). Grape seed proanthocyanidin extracts alleviate oxidative stress and ER stress in skeletal muscle of low-dose streptozotocin- and high-carbohydrate/high-fat diet-induced diabetic rats. Molecular Nutrition and Food Research, 57(2), 365–369. https://doi.org/10.1002/mnfr.201200463
Evard, H., Kruve, A., Lõhmus, R., & Leito, I. (2015). Paper spray ionization mass spectrometry: Study of a method for fast-screening analysis of pesticides in fruits and vegetables. Journal of Food Composition and Analysis, 41, 221–225. https://doi.org/10.1016/j.jfca.2015.01.010
Gallego, A. M., Rojas, L. F., Rodriguez, H. A., Mora, C., Atehortúa, L., Urrea, A. I., … Pabón-Mora, N. (2019). Metabolomic profile of cacao cell suspensions growing in blue light/dark conditions with potential in food biotechnology. Plant Cell, Tissue and Organ Culture, 139(2), 275–294. https://doi.org/10.1007/s11240-019-01679-3
Gálvez, M., Martín-Cordero, C., & Ayuso, M. J. (2005). Pharmacological activities of iridoids biosynthesized by route II. Studies in Natural Products Chemistry, 32(PART L), 365–394. https://doi.org/10.1016/S1572-5995(05)80060-2
Ghosh, S., Basak, P., Dutta, S., Chowdhury, S., & Sil, P. C. (2017). New insights into the ameliorative effects of ferulic acid in pathophysiological conditions. Food and Chemical Toxicology, 103, 41–55. https://doi.org/10.1016/j.fct.2017.02.028
Gibbons, C. H., Schmidt, P., Biaggioni, I., Frazier-Mills, C., Freeman, R., Isaacson, S., … Kaufmann, H. (2017). The recommendations of a consensus panel for the screening, diagnosis, and treatment of neurogenic orthostatic hypotension and associated supine hypertension. Journal of Neurology, 264(8), 1567–1582. https://doi.org/10.1007/s00415-016-8375-x
Guo, T., Zhang, Z., Yannell, K. E., Dong, Y., & Cooks, R. G. (2017). Paper spray ionization mass spectrometry for rapid quantification of illegal beverage dyes. Analytical Methods, 9(44), 6273–6279. https://doi.org/10.1039/c7ay02241g
Huang, J. L., Fu, S. T., Jiang, Y. Y., Cao, Y. B., Guo, M. L., Wang, Y., & Xu, Z. (2007). Protective effects of Nicotiflorin on reducing memory dysfunction, energy metabolism failure and oxidative stress in multi-infarct dementia model rats. Pharmacology Biochemistry and Behavior, 86(4), 741–748. https://doi.org/10.1016/j.pbb.2007.03.003
Juurlink, B. H. J., Azouz, H. J., Aldalati, A. M. Z., Altinawi, B. M. H., & Ganguly, P. (2014). Hydroxybenzoic acid isomers and the cardiovascular system. Nutrition Journal, 13(1), 1–10. https://doi.org/10.1186/1475-2891-13-63
Khoo, H. E., Azlan, A., Tang, S. T., & Lim, S. M. (2017). Anthocyanidins and anthocyanins: Colored pigments as food, pharmaceutical ingredients, and the potential health benefits. Food and Nutrition Research, 61(1), 0–21. https://doi.org/10.1080/16546628.2017.1361779
Kim, W., Seong, K. M., & Youn, B. (2011). Phenylpropanoids in radioregulation: Double edged sword. Experimental and Molecular Medicine, 43(6), 323–333. https://doi.org/10.3858/emm.2011.43.6.034
Kugelman, A., & Durand, M. (2011). A comprehensive approach to the prevention of bronchopulmonary dysplasia. Pediatric Pulmonology, 46(12), 1153–1165. https://doi.org/10.1002/ppul.21508
Lam, K. Y., Sasmita, A. O., Pick, A., Ling, K., Koh, R. Y., & Leong, K. G. (2018). Neuroprotective Mechanisms of Orientin against Hydrogen Peroxide- induced Oxidative Damage in SH-SY5Y Cells. Journal of Biochemistry, Microbiology and Biotechnology, 6(1), 10–18.
Lamhamdi, M., Lafont, R., Rharrabe, K., Sayah, F., Aarab, A., & Bakrim, A. (2016). 20-Hydroxyecdysone protects wheat seedlings (Triticum aestivum L.) against lead stress. Plant Physiology and Biochemistry, 98, 64–71. https://doi.org/10.1016/j.plaphy.2015.11.006
Li, A., Wei, P., Hsu, H. C., & Cooks, R. G. (2013). Direct analysis of 4-methylimidazole in foods using paper spray mass spectrometry. Analyst, 138(16), 4624–4630. https://doi.org/10.1039/c3an00888f
Li, R., Guo, M., Zhang, G., Xu, X., & Li, Q. (2006). Nicotiflorin reduces cerebral ischemic damage and upregulates endothelial nitric oxide synthase in primarily cultured rat cerebral blood vessel endothelial cells. Journal of Ethnopharmacology, 107(1), 143–150. https://doi.org/10.1016/j.jep.2006.04.024
Martinez-Zapata, M. J., Vernooij, R. W., Uriona Tuma, S. M., Stein, A. T., Moreno, R. M., Vargas, E., … Bonfill Cosp, X. (2016). Phlebotonics for venous insufficiency. Cochrane Database of Systematic Reviews, 2016(4). https://doi.org/10.1002/14651858.CD003229.pub3
Meng, S., Cao, J., Feng, Q., Peng, J., & Hu, Y. (2013). Roles of chlorogenic acid on regulating glucose and lipids metabolism: A review. Evidence-Based Complementary and Alternative Medicine, 2013. https://doi.org/10.1155/2013/801457
Morling, J. R., Yeoh, S. E., & Kolbach, D. N. (2015). Rutosides for treatment of post-thrombotic syndrome. Cochrane Database of Systematic Reviews, 2015(9). https://doi.org/10.1002/14651858.CD005625.pub3
Murakami, A., Ashida, H., & Terao, J. (2008). Multitargeted cancer prevention by quercetin. Cancer Letters, 269(2), 315–325. https://doi.org/10.1016/j.canlet.2008.03.046
Naveed, M., Hejazi, V., Abbas, M., Kamboh, A. A., Khan, G. J., Shumzaid, M., … XiaoHui, Z. (2018). Chlorogenic acid (CGA): A pharmacological review and call for further research. Biomedicine and Pharmacotherapy, 97(August 2017), 67–74. https://doi.org/10.1016/j.biopha.2017.10.064
Odai, T., Terauchi, M., Kato, K., Hirose, A., & Miyasaka, N. (2019). Effects of grape seed proanthocyanidin extract on vascular endothelial function in participants with prehypertension: A randomized, double-blind, placebo-controlled study. Nutrients, 11(12). https://doi.org/10.3390/nu11122844
Oliveira, C. T., Ramos, A. L. C. C., Mendonça, H. D. O. P., Consenza, G. P., Silva, M. R., Fernandes, C., ... & de Araújo, R. L. B. (2020). Quantification of 6-gingerol, metabolomic analysis by paper spray mass spectrometry and determination of antioxidant activity of ginger rhizomes (Zingiber officinale). Research, Society and Development, 9(8), 366984822. http://dx.doi.org/10.33448/rsd-v9i8.4822
Onakpoya, I. J., Spencer, E. A., Thompson, M. J., & Heneghan, C. J. (2015). The effect of chlorogenic acid on blood pressure: A systematic review and meta-analysis of randomized clinical trials. Journal of Human Hypertension, 29(2), 77–81. https://doi.org/10.1038/jhh.2014.46
Oracz, J., Nebesny, E., & Żyżelewicz, D. (2015). Changes in the flavan-3-ols, anthocyanins, and flavanols composition of cocoa beans of different Theobroma cacao L. groups affected by roasting conditions. European Food Research and Technology, 241(5), 663–681. https://doi.org/10.1007/s00217-015-2494-y
Oracz, J., Zyzelewicz, D., & Nebesny, E. (2015). The Content of Polyphenolic Compounds in Cocoa Beans (Theobroma cacao L.), Depending on Variety, Growing Region, and Processing Operations: A Review. Critical Reviews in Food Science and Nutrition, 55(9), 1176–1192. https://doi.org/10.1080/10408398.2012.686934
Ortega, N., Romero, M. P., MacIà, A., Reguant, J., Anglès, N., Morelló, J. R., & Motilva, M. J. (2008). Obtention and characterization of phenolic extracts from different cocoa sources. Journal of Agricultural and Food Chemistry, 56(20), 9621–9627. https://doi.org/10.1021/jf8014415
Patras, M. A., Milev, B. P., Vrancken, G., & Kuhnert, N. (2014). Identification of novel cocoa flavonoids from raw fermented cocoa beans by HPLC-MSn. Food Research International, 63, 353–359. https://doi.org/10.1016/j.foodres.2014.05.031
Peláez, P. P., Guerra, S., & Contreras, D. (2016). Changes in physical and chemical characteristics of fermented cocoa (Theobroma cacao) beans with manual and semi-mechanized transfer, between fermentation boxes. Scientia Agropecuaria, 07(02), 111–119. https://doi.org/10.17268/sci.agropecu.2016.02.04
Pereira-Caro, G., Borges, G., Nagai, C., Jackson, M. C., Yokota, T., Crozier, A., & Ashihara, H. (2013). Profiles of phenolic compounds and purine alkaloids during the development of seeds of Theobroma cacao cv. Trinitario. Journal of Agricultural and Food Chemistry, 61(2), 427–434. https://doi.org/10.1021/jf304397m
Perez-Vizcaino, F., & Fraga, C. G. (2018). Research trends in flavonoids and health. Archives of Biochemistry and Biophysics, 646(March), 107–112. https://doi.org/10.1016/j.abb.2018.03.022
Quelal-Vásconez, M. A., Lerma-García, M. J., Pérez-Esteve, É., Arnau-Bonachera, A., Barat, J. M., & Talens, P. (2020). Changes in methylxanthines and flavanols during cocoa powder processing and their quantification by near-infrared spectroscopy. Lwt, 117(September 2019), 108598. https://doi.org/10.1016/j.lwt.2019.108598
Ramos, A. L. C. C., Mendes, D. D., Silva, M. R., Augusti, R., Melo, J. O. F., de Araújo, R. L. B., & Lacerda, I. C. A. (2020). Chemical profile of Eugenia brasiliensis (Grumixama) pulp by PS/MS paper spray and SPME-GC/MS solid-phase microextraction. Research, Society and Development, 9(7), 318974008. http://dx.doi.org/10.33448/rsd-v9i7.4008
Riboni, N., Quaranta, A., Motwani, H. V., Österlund, N., Gräslund, A., Bianchi, F., & Ilag, L. L. (2019). Solvent-Assisted Paper Spray Ionization Mass Spectrometry (SAPSI-MS) for the Analysis of Biomolecules and Biofluids. Scientific Reports, 9(1), 1–12. https://doi.org/10.1038/s41598-019-45358-x
Roth, S., Spalinger, M. R., Müller, I., Lang, S., Rogler, G., & Scharl, M. (2014). Bilberry-derived anthocyanins prevent IFN-γ-induced pro-inflammatory signalling and cytokine secretion in human THP-1 monocytic cells. Digestion, 90(3), 179–189. https://doi.org/10.1159/000366055
Rufino, M. do S. M., Alves, R. E., de Brito, E. S., Pérez-Jiménez, J., Saura-Calixto, F., & Mancini-Filho, J. (2010). Bioactive compounds and antioxidant capacities of 18 non-traditional tropical fruits from Brazil. Food Chemistry, 121(4), 996–1002. https://doi.org/10.1016/j.foodchem.2010.01.037
Saint-Cricq De Gaulejac, N., Glories, Y., & Vivas, N. (1999). Free radical scavenging effect of anthocyanins in red wines. Food Research International, 32(5), 327–333. https://doi.org/10.1016/S0963-9969(99)00093-9
Sánchez-Rabaneda, F., Jáuregui, O., Casals, I., Andrés-Lacueva, C., Izquierdo-Pulido, M., & Lamuela-Raventós, R. M. (2003). Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao). Journal of Mass Spectrometry, 38(1), 35–42. https://doi.org/10.1002/jms.395
Seeram, N. P., Momin, R. A., Nair, M. G., & Bourquin, L. D. (2001). Cyclooxygenase inhibitory and antioxidant cyanidin glycosides in cherries and berries. Phytomedicine, 8(5), 362–369. https://doi.org/10.1078/0944-7113-00053
Silva, M. R., Freitas, L. G., Souza, A. G., Araújo, R. L. B., Lacerda, I. C. A., Pereira, H. V., … Melo, J. O. F. (2019). Antioxidant Activity and Metabolomic Analysis of Cagaitas (Eugenia dysenterica) Using using Paper Paper Spray Spray Mass Mass Spectrometry Spectrometry. Journal of the Brazilian Chemical Society, 30(5), 1034–1044. https://doi.org/10.21577/0103-5053.20190002
Snel, J., & Lorist, M. M. (2011). Effects of caffeine on sleep and cognition. In Progress in Brain Research (1st ed., Vol. 190). https://doi.org/10.1016/B978-0-444-53817-8.00006-2
Song, Y., Cui, T., Xie, N., Zhang, X., Qian, Z., & Liu, J. (2014). Protocatechuic acid improves cognitive deficits and attenuates amyloid deposits, inflammatory response in aged AβPP/PS1 double transgenic mice. International Immunopharmacology, 20(1), 276–281. https://doi.org/10.1016/j.intimp.2014.03.006
Stavric, B. (1988). Methylxanthines: Toxicity to humans. 3. Theobromine, paraxanthine and the combined effects of methylxanthines. Food and Chemical Toxicology, 26(8), 725–733. https://doi.org/10.1016/0278-6915(88)90073-7
Steinberg, F. M., Bearden, M. M., & Keen, C. L. (2003). Cocoa and chocolate flavonoids: Implications for cardiovascular health. Journal of the American Dietetic Association, 103(2), 215–223. https://doi.org/10.1053/jada.2003.50028
Sunil, C., & Xu, B. (2019). An insight into the health-promoting effects of taxifolin (dihydroquercetin). Phytochemistry, 166(July), 112066. https://doi.org/10.1016/j.phytochem.2019.112066
Szczepaniak, O., Ligaj, M., Kobus-Cisowska, J., Tichoniuk, M., Dziedziński, M., Przeor, M., & Szulc, P. (2020). The genoprotective role of naringin. Biomolecules, 10(5), 1–20. https://doi.org/10.3390/biom10050700
Taverna, D., Di Donna, L., Bartella, L., Napoli, A., Sindona, G., & Mazzotti, F. (2016). Fast analysis of caffeine in beverages and drugs by paper spray tandem mass spectrometry. Analytical and Bioanalytical Chemistry, 408(14), 3783–3787. https://doi.org/10.1007/s00216-016-9468-1
Tebayashi, S. I., Ishihara, A., Tsuda, M., & Iwamura, H. (2000). Induction of clovamide by jasmonic acid in red clover. Phytochemistry, 54(4), 387–392. https://doi.org/10.1016/S0031-9422(00)00098-4
Tsai, S. jei, & Yin, M. chin. (2012). Anti-glycative and anti-inflammatory effects of protocatechuic acid in brain of mice treated by d-galactose. Food and Chemical Toxicology, 50(9), 3198–3205. https://doi.org/10.1016/j.fct.2012.05.056
Türker, M., & Dalar, A. (2013). In vitro antioxidant and enzyme inhibitory properties and phenolic composition of M. neglecta Wallr. (Malvaceae) fruit: A traditional medicinal fruit from Eastern Anatolia. Industrial Crops and Products, 51, 376–380. https://doi.org/10.1016/j.indcrop.2013.09.015
Venditti, A., Bianco, A., Frezza, C., Conti, F., Bini, L. M., Giuliani, C., … Maggi, F. (2015). Essential oil composition, polar compounds, glandular trichomes and biological activity of Hyssopus officinalis subsp. aristatus (Godr.) Nyman from central Italy. Industrial Crops and Products, 77, 353–363. https://doi.org/10.1016/j.indcrop.2015.09.002
Wan, C. W., Wong, C. N. Y., Pin, W. K., Wong, M. H. Y., Kwok, C. Y., Chan, R. Y. K., … Chan, S. W. (2013). Chlorogenic acid exhibits cholesterol lowering and fatty liver attenuating properties by up-regulating the gene expression of PPAR-α in hypercholesterolemic rats induced with a high-cholesterol diet. Phytotherapy Research, 27(4), 545–551. https://doi.org/10.1002/ptr.4751
Wang, H., Liu, J., Cooks, R. G., & Ouyang, Z. (2010). Paper Spray for Direct Analysis of Complex Mixtures Using Mass Spectrometry. Angewandte Chemie, 122(5), 889–892. https://doi.org/10.1002/ange.200906314
Wang, X., An, F., Wang, S., An, Z., & Wang, S. (2017). Orientin Attenuates Cerebral Ischemia/Reperfusion Injury in Rat Model through the AQP-4 and TLR4/NF-κB/TNF-α Signaling Pathway. Journal of Stroke and Cerebrovascular Diseases, 26(10), 2199–2214. https://doi.org/10.1016/j.jstrokecerebrovasdis.2017.05.002
Winter, A. N., Brenner, M. C., Punessen, N., Snodgrass, M., Byars, C., Arora, Y., & Linseman, D. A. (2017). Comparison of the Neuroprotective and Anti-Inflammatory Effects of the Anthocyanin Metabolites, Protocatechuic Acid and 4-Hydroxybenzoic Acid. Oxidative Medicine and Cellular Longevity, 2017. https://doi.org/10.1155/2017/6297080
Xiao, Z.-P., Peng, Z.-Y., Peng, M.-J., Yan, W.-B., Ouyang, Y.-Z., & Zhu, H.-L. (2011). Flavonoids Health Benefits and Their Molecular Mechanism. Mini-Reviews in Medicinal Chemistry, 11(2), 169–177. https://doi.org/10.2174/138955711794519546
Yazaki, K., Sasaki, K., & Tsurumaru, Y. (2009). Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry, 70(15–16), 1739–1745. https://doi.org/10.1016/j.phytochem.2009.08.023
Yousuf, B., Gul, K., Wani, A. A., & Singh, P. (2016). Health Benefits of Anthocyanins and Their Encapsulation for Potential Use in Food Systems: A Review. Critical Reviews in Food Science and Nutrition, 56(13), 2223–2230. https://doi.org/10.1080/10408398.2013.805316
Yuan, Y., Gong, X., Zhang, L., Jiang, R., Yang, J., Wang, B., & Wan, J. (2017). Chlorogenic acid ameliorated concanavalin A-induced hepatitis by suppression of Toll-like receptor 4 signaling in mice. International Immunopharmacology, 44, 97–104. https://doi.org/10.1016/j.intimp.2017.01.017
Descargas
Publicado
Cómo citar
Número
Sección
Licencia
Derechos de autor 2020 Afonso Henrique de Oliveira Júnior, Ana Luiza Coeli Cruz Ramos, Mayara Neves Santos Guedes, Miriã Cristina Pereira Fagundes, Rodinei Augusti, Júlio Onésio Ferreira Melo

Esta obra está bajo una licencia internacional Creative Commons Atribución 4.0.
Los autores que publican en esta revista concuerdan con los siguientes términos:
1) Los autores mantienen los derechos de autor y conceden a la revista el derecho de primera publicación, con el trabajo simultáneamente licenciado bajo la Licencia Creative Commons Attribution que permite el compartir el trabajo con reconocimiento de la autoría y publicación inicial en esta revista.
2) Los autores tienen autorización para asumir contratos adicionales por separado, para distribución no exclusiva de la versión del trabajo publicada en esta revista (por ejemplo, publicar en repositorio institucional o como capítulo de libro), con reconocimiento de autoría y publicación inicial en esta revista.
3) Los autores tienen permiso y son estimulados a publicar y distribuir su trabajo en línea (por ejemplo, en repositorios institucionales o en su página personal) a cualquier punto antes o durante el proceso editorial, ya que esto puede generar cambios productivos, así como aumentar el impacto y la cita del trabajo publicado.