The flavonoid content in orange peels of different Brazilian citrus varieties such as bahia, lima, lima-of-persian, morcote, pera, ponkan, seleta, cravo, kinkan and pomelo was assessed. Industry processing juice wastes such as bagasse, bagasse residues, animal feeding bagasse, pulp WEUE and CORE-wash were also analyzed. The HPLC analysis indicates that the most abundant flavonoids found in these Brazilian citrus peels are hesperidin and naringin. The solvents used are selective for flavonoid extraction, and depending on their polarity, glycoside or aglycone flavonoids are extracted. The use of multivariate analysis shows that DMSO is the best solvent to extract glycosides flavanones while hexane displays high selectivity in the extraction of polymethoxylated flavones. The flavonoids present in the orange wastes, obtained at different stages of the industrial processing, are qualitative and quantitatively different. The identification and quantification of the flavonoid composition in each Brazilian citrus variety were evaluated and allowed the selection of the best solvent for the extraction of each specific class of flavonoids. These compounds were found to be more abundant in the fruit peels than in their juices, revealing their great industrial potential. The residual portion of the processing juices is also rich in flavonoids, depending on the processing step.
KeywordsCitrusOrange PeelFlavonoidBrazilian OrangeOrange Juice Processing Wastes
Hertog, M.G.L., Feskens, E.J.M., Kromhout, D., Hollman, P.C.H. and Katan, M.B. (1993) Dietary Antioxidant Flavonoids and Risk of Coronary Heart Disease: The Zutphen Elderly Study. The Lancet, 342, 1007-1011. https://doi.org/10.1016/0140-6736(93)92876-U
Benavente-García, O., Castillo, J., Marin, F.R., Ortuno, A. and Del Río, J.A. (1997) Uses and Properties of Citrus Flavonoids. Journal of Agricultural and Food Chemistry, 45, 4505-4515. https://doi.org/10.1021/jf970373s
Yao, L.H., Jiang, Y.M., Shi, J., Tomás-Barberán, F.A., Datta, N., Singanusong, R. and Chen, S.S. (2004) Flavonoids in Food and Their Health Benefits. Plant Foods for Human Nutrition, 59, 113-122. https://doi.org/10.1007/s11130-004-0049-7
Benavente-García, O. and Castillo, J. (2008) Update on Uses and Properties of Citrus Flavonoids: New Findings in Anticancer, Cardiovascular, and Anti-Inflammatory Activity. Journal of Agricultural and Food Chemistry, 56, 6185-6205. https://doi.org/10.1021/jf8006568
Manthey, J.A., Guthrie, N. and Grohmann, K. (2001) Biological Properties of Citrus Flavonoids Pertaining to Cancer and Inflammation. Current Medicinal Chemistry, 8, 135-153. https://doi.org/10.2174/0929867013373723
Tripoli, E., Guardia, M.L., Giammanco, S., Majo, D.D. and Giammanco, M. (2007) Citrus Flavonoids: Molecular Structure, Biological Activity and Nutritional Properties: A Review. Food Chemistry, 104, 466-479.
Cavia-Saiz, M., Busto, M.D., Pilar-Izquierdo, M.C., Ortega, N., Perez-Mateos, M. and Muniz, P. (2010) Antioxidant Properties, Radical Scavenging Activity and Biomolecule Protection Capacity of Flavonoid Naringenin and Its Glycoside Naringin: A Comparative Study. Journal of Science of Food and Agriculture, 90, 1238-1244. https://doi.org/10.1002/jsfa.3959
Madeira Jr., J.V. and Macedo, G.A. (2015) Simultaneous Extraction and Biotransformation Process to Obtain High Bioactivity Phenolic Compounds from Brazilian Citrus Residues. Biotechnology Progress, 31, 1273-1279. https://doi.org/10.1002/btpr.2126
Sergent, T., Vanderstraeten, J., Winand, J., Beguin, P. and Schneider, Y.J. (2012) Phenolic Compounds and Plant Extracts as Potential Natural Anti-Obesity Substances. Food Chemistry, 135, 68-73.
Arabbi, P.R., Genovese, M.I. and Lajolo, F.M. (2004) Flavonoids in Vegetable Foods Commonly Consumed in Brazil and Estimated Ingestion by the Brazilian Population. Journal of Agricultural and Food Chemistry, 52, 1124-1131. https://doi.org/10.1021/jf0499525
Hernández-Carranza, P., ávila-Sosa, R., Guerrero-Beltrán, J.A., Navarro-Cruz, A.R., Corona-Jiménez, E. and Ochoa-Velasco, C.E. (2016) Optimization of Antioxidant Compounds Extraction from Fruit By-Products: Apple Pomace, Orange and Banana Peel. Journal of Food Processing and Preservation, 40, 103-115. https://doi.org/10.1111/jfpp.12588
Ghasemi, K., Ghasemi, Y. and Ebrahimzadeh, M.A. (2009) Antioxidant Activity, Phenol and Flavonoid Contents of 13 Citrus Species Peels and Tissues. Pakistan Journal of Pharmaceutical Sciences, 22, 277-281.
Bocco, A., Cuvelier, M.E., Richard, H. and Berset, C. (1998) Antioxidant Activity and Phenolic Composition of Citrus Peel and Seed Extracts. Journal of Agricultural and Food Chemistry, 46, 2123-2129. https://doi.org/10.1021/jf9709562
Anagnostopoulou, M.A., Kefalas, P., Papageorgiou, V.P., Assimopoulou, A.N. and Boskou, D. (2006) Radical Scavenging Activity of Various Extracts and Fractions of Sweet Orange Peel (Citrus sinensis). Food Chemistry, 94, 19-25.
Hirano, T., Abe, K., Gotoh, M. and Oka, K. (1995) Citrus Flavone Tangeretin Inhibits Leukaemic HL-60 Cell Growth Partially through Induction of Apoptosis with Less Cytotoxicity on Normal Lymphocytes. British Journal of Cancer, 72, 1380-1388. https://doi.org/10.1038/bjc.1995.518
Itoigawa, M., Takeya, K. and Furukawa, H. (1994) Cardiotonic Flavonoids from Citrus Plants (Rutaceae). Biological and Pharmaceutical Bulletin, 17, 1519-1521. https://doi.org/10.1248/bpb.17.1519
Ehler, S.A. (2011) Citrus and Its Benefits. Journal of Botany, 5, 201-207.
So, F.V., Guthrie, N., Chambers, A.F., Moussa, M. and Carroll, K.K. (1996) Inhibition of Human Breast Cancer Cell Proliferation and Delay of Mammary Tumorigenesis by Flavonoids and Citrus Juices. Nutrition and Cancer, 26, 167-181. https://doi.org/10.1080/01635589609514473
Ramos, S. (2007) Effects of Dietary Flavonoids on Apoptotic Pathways Related to Cancer Chemoprevention. Journal of Nutritional Biochemistry, 18, 427-442. https://doi.org/10.1016/j.jnutbio.2006.11.004
Meiyanto, E., Hermawan, A. and Anindyajati, A. (2012) Natural Products for Cancer-Targeted Therapy: Citrus Flavonoids as Potent Chemopreventive Agents. Asian Pacific Journal of Cancer Prevention, 13, 427-436. https://doi.org/10.7314/APJCP.2012.13.2.427
Molina-Calle, M., Priego-Capote, F. and Luque de Castro, M.D. (2015) Development and Application of a Quantitative Method for Determination of Flavonoids in Orange Peel: Influence of Sample Pretreatment on Composition. Talanta, 144, 349-355.
Nijveldt, R.J., van Nood, E., van Hoorn, D.E., Boelens, P.G., van Norren, K. and van Leeuwen, P.A. (2001) Flavonoids: A Review of Probable Mechanisms of Action and Potential Applications. American Journal of Clinical Nutrition, 74, 418-425.
Liu, E.H., Zhao, P., Duan, L., Zheng, G.D., Guo, L., Yang, H. and Li, P. (2013) Simultaneous Determination of Six Bioactive Flavonoids in Citri reticulatae Pericarpium by Rapid Resolution Liquid Chromatography Coupled with Triple Quadrupole Electrospray Tandem Mass Spectrometry. Food Chemistry, 141, 3977-3983.
Abad-García, B., Garmón-Lobato, S., Berrueta, L.A., Gallo, B. and Vicente, F. (2012) On Line Characterization of 58 Phenolic Compounds in Citrus Fruit Juices from Spanish Cultivars by High-Performance Liquid Chromatography with Photodiode-Array Detection Coupled to Electrospray Ionization Triple Quadrupole Mass Spectrometry. Talanta, 99, 213-224.
Ciric, A., Prosen, H., Jelikic-Stankov, M. and Durdevic, P. (2012) Evaluation of Matrix Effect in Determination of Some Bioflavonoids in Food Samples by LC-MS/MS method. Talanta, 99, 780-790.
Da Rocha, A.S. (2006) Características bioquímicas em cascas, folhas e talos de vege-tais pós-colheita em sistema de producao convencional e organico. Dissertation, Unesp, Botucatu, SP, Brasil.
Omoba, O.S., Obafaye, R.O., Salawu, S.O., Boligon, A.A. and Athayde, M.L. (2015) HPLC-DAD Phenolic Characterization and Antioxidant Activities of Ripe and Unripe Sweet Orange Peels. Antioxidants, 4, 498-512. https://doi.org/10.3390/antiox4030498
Pupin, A.M., Dennis, M.J. and Toledo, M.C.F. (1998) Flavone Glycosides in Brazilian Orange Juice. Food Chemistry, 61, 275-280.
Cerqueira, L.C.R., David, J.M., Borges, R.S.Q., Ferreira, S.L.C., David, J.P., Reis, P.S., and Bruns, R.E. (2014) Determination of Flavanones in Orange Juices Obtained from Different Sources by HPLC/DAD. Journal of Analytical Methods in Chemistry, 14, 13-18.
Mouly, P., Gaydou, E.M. and Auffray, A. (1998) Simultaneous Separation of Flavanone Glycosides and Polymethoxylated Flavones in Citrus Juices Using Liquid Chromatography. Journal of Chromatography A, 800, 171-179.
M’hiri, N., Ioannou, I., Mihoubi Boudhrioua, N. and Ghoul, M. (2015) Effect of Different Operating Conditions on the Extraction of Phenolic Compounds in Orange Peel. Food and Bioproducts Processing, 96, 161-170. https://doi.org/10.1016/j.fbp.2015.07.010
Sawalha, S.M.S., Arráez-Román, D., Segura-Carretero, A. and Fernández-Gutiérrez, A. (2009) Quantification of Main Phenolic Compounds in Sweet and Bitter Orange Peel Using CE-MS/MS. Food Chemistry, 116, 567-574.
Massenti, R., Lo Bianco, R., Sandhu, A.K., Gu, L. and Sims, C. (2016) Huanglongbing Modifies Quality Components and Flavonoid Content of “Valencia” Oranges. Journal of Science and Food Agriculture, 96, 73-78. https://doi.org/10.1002/jsfa.7061
Chen, X.M., Tait, A.R. and Kitts, D.D. (2017) Flavonoid Composition of Orange Peel and Its Association with Antioxidante and Anti-Inflammatory Activities. Food Chemistry, 218, 15-21.
Guccione, C., Bergonzi, M.C., Piazzini, V. and Bilia, A.R. (2016) A Simple and Rapid HPLC-PDA MS Method for the Profiling of Citrus Peels and Traditional Italian Liquors. Planta Medica, 82, 1039-1045. https://doi.org/10.1055/s-0042-108735
Diniz, A.B. and Oliveira, D.R. (2015) Composicao química da laranja kinkan e de frutas cítricas. Demetra, 10, 835-844.
Shahwar, D., Raza, M.A. and Atta, U.R. (2013) Identification of Flavonoids with Trypsin Inhibitory Activity Extracted from Orange Peel and Green Tea Leaves. Journal of Science of Foods and Agriculture, 93, 1420-1426. https://doi.org/10.1002/jsfa.5910
Munhoz, J.R. and Morabito, R. (2010) Otimizacao no planejamento agregado de producao em indústrias de processamento de suco concentrado congelado de laranja. Gestao & Producao, 17, 465-481. https://doi.org/10.1590/S0104-530X2010000300003