journal article·2021-12-21Open access

An Overview of Bioactive Flavonoids from Citrus Fruits

Mohamed Addi, Amine Elbouzidi, Malika Abid, Duangjai Tungmunnithum, Ahmed Elamrani, Christophe Hano

Applied Sciences· Volume 12· Issue 1

Abstract

Citrus species are one of the world’s popular fruit crops, cultivated all over the world for their economic and nutritional values. Citrus, like other fruits and vegetables, are an important source of several antioxidant molecules (polyphenols, ascorbic acid, and carotenoids) that can inhibit the harmful effects of free radicals on the human body; due to their functional values and health-promoting properties, Citrus species are considered valuable fruits not only in agri-food industry, but also in pharmaceutical industry. Flavonoids are among the major constituents of polyphenols found in different parts of Citrus fruits (skin, peels, seed, pulp membrane, and juice). Flavonoids have different biological properties (antiviral, antifungal, and antibacterial activities). Several studies have also shown the health-related properties of Citrus flavonoids, especially antioxidant, anticancer, anti-inflammation, anti-aging, and cardiovascular protection activities. In the present review, attempts are made to discuss the current trends of research on flavonoids in different Citrus species.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Phytochemicals and Antioxidant Activities · Bioactive Compounds in Plants · Plant biochemistry and biosynthesis

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Laboratoire d’Amélioration des Productions Agricoles, Biotechnologie et Environnement (LAPABE), Faculté des Sciences, Université Mohammed Premier, Oujda 60000, Morocco

Laboratoire de Biologie des Ligneux et des Grandes Cultures, INRAE USC1328, Campus Eure et Loir, Orleans University, 28000 Chartres, France

Le StudiumInstitue for Advanced Studies, 1 Rue Dupanloup, 45000 Orléans, France

Department of Pharmaceutical Botany, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand

References (96)

Show source-provided references
1. Zhou, Z.Q. (2012). Citrus Fruits Nutrition, Science Press.
2. Natural bioactive compounds of Citrus limon for food and health10.1016/j.jpba.2009.07.027 ↗
3. Flavonoid and chlorogenic acid changes in skin of ‘Elstar’ and ‘Jonagold’apples during development and ripening10.1016/S0304-4238(00)00255-7 ↗
4. Flavanones in oranges, tangerines (mandarins), tangors, and tangelos: A compilation and review of the data from the analytical literature10.1016/j.jfca.2005.12.006 ↗
5. Extraction of phenolics from citrus peels: I. Solvent extraction method10.1016/j.seppur.2005.07.005 ↗
6. Update on uses and properties of citrus flavonoids: New findings in anticancer, cardiovascular, and anti-inflammatory activity10.1021/jf8006568 ↗
7. Antioxidant activity of Citrus fruits10.1016/j.foodchem.2015.09.072 ↗
8. Reuther, W., Batchelor, L.D., and Webber, H.J. (1967). History, World Distribution, Botany, and Varieties, University of California, Division of Agricultural Sciences.
9. The Botany of Citrus and Its Wild Relatives
10. Fundamental discussion of Citrus classification
11. Krueger, R.R., and Navarro, L. (2007). Citrus Germplasm Resources. Citrus Genetics, Breeding and Biotechnology, CAB International.10.1079/9780851990194.0045 ↗
12. Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health10.1002/biot.200700084 ↗
13. Phenylpropanoid Biosynthesis10.1093/mp/ssp106 ↗
14. The chalcone synthase superfamily of type III polyketide synthases10.1039/b100917f ↗
15. Tai, D., Tian, J., Zhang, J., Song, T., and Yao, Y. (2014). A Malus crabapple chalcone synthase gene, McCHS, regulates red petal color and flavonoid biosynthesis. PLoS ONE., 9.10.1371/journal.pone.0110570 ↗
16. Flavanone glycoside biosynthesis in citrus: Chalcone synthase, UDP-glucose: Flavanone-7-O-glucosyl-transferase and-rhamnosyl-transferase activities in cell-free extracts10.1104/pp.91.4.1323 ↗
17. Dihydroflavonol 4-Reductase Genes from Freesia hybrida Play Important and Partially Overlapping Roles in the Biosynthesis of Flavonoids
18. A role for leucoanthocyanidin reductase in the extension of proanthocyanidins10.1038/nplants.2016.182 ↗
19. Anticancer activities of citrus peel polymethoxyflavones related to angiogenesis and others10.1155/2014/453972 ↗
20. Phenolic composition of Chinese wild mandarin (Citrus reticulata Balnco.) pulps and their antioxidant properties10.1016/j.indcrop.2013.11.016 ↗
21. Harborne, J.B. (2013). The Flavonoids: Advances in Research Since 1980, Springer.
22. Composition and distribution of phenolic acids in Ponkan (Citrus poonensis Hort. ex Tanaka) and Huyou (Citrus paradisi Macf. Changshanhuyou) during maturity10.1016/j.jfca.2008.03.003 ↗
23. Impact of high pressure and pulsed electric fields on bioactive compounds and antioxidant activity of orange juice in comparison with traditional thermal processing10.1021/jf048839b ↗
24. Effect of high hydrostatic pressure treatment on post processing antioxidant activity of fresh Navel orange juice10.1016/j.foodchem.2004.04.040 ↗
25. Changes of flavonoids, vitamin C and antioxidant capacity in minimally processed citrus segments and juices during storage10.1016/S0308-8146(03)00180-8 ↗
26. Flavanone glycosides in Brazilian orange juice10.1016/S0308-8146(97)00093-9 ↗
27. Dietary hydroxybenzoic acid derivatives–nature, occurrence and dietary burden10.1002/(SICI)1097-0010(20000515)80:7<1024::AID-JSFA567>3.0.CO;2-S ↗
28. Yao, Q., Lin, M.-T., Zhu, Y.-D., Xu, H.-L., and Zhao, Y.-Z. (2018). Recent trends in potential therapeutic applications of the dietary flavonoid didymin. Molecules, 23.10.3390/molecules23102547 ↗
29. The flavonoid, carotenoid and pectin content in peels of citrus cultivated in Taiwan10.1016/j.foodchem.2007.05.086 ↗
30. Underestimated sources of flavonoids, limonoids and dietary fibre: Availability in lemon’s by-products10.1016/j.jff.2014.04.004 ↗
31. Citrus limon: A source of flavonoids of pharmaceutical interest10.1016/S0308-8146(03)00272-3 ↗
32. Optimized microwave-assisted extraction of phenolic acids from citrus mandarin peels and evaluation of antioxidant activity in vitro10.1016/j.seppur.2009.08.012 ↗
33. Tumbas, V.T., Ćetković, G.S., Đilas, S.M., Čanadanović-Brunet, J.M., Vulić, J.J., Knez, Ž., and Škerget, M. (2010). Antioxidant activity of mandarin (Citrus reticulata) peel. Acta Period. Technol., 195–203.10.2298/APT1041195T ↗
34. Enhanced extraction of flavanones hesperidin and narirutin from Citrus unshiu peel using subcritical water10.1016/j.jfoodeng.2011.12.019 ↗
35. Supercritical fluid extraction of naringin from the peel of Citrus paradisi10.1002/pca.706 ↗
36. Extraction of nobiletin and tangeretin from Citrus depressa Hayata by supercritical carbon dioxide with ethanol as modifier10.1016/j.indcrop.2009.09.003 ↗
37. Pressurised liquid extraction combining LC–DAD–ESI/MS analysis as an alternative method to extract three major flavones in Citrus reticulata ‘Chachi’ (Guangchenpi)10.1016/j.foodchem.2011.07.129 ↗
38. Extraction of Bioactive Flavonoid Compounds from Orange (Cit-rus sinensis) Peel Using Supercritical CO2
39. Flavonoids in Grapefruit and commercial grapefruit juices: Concentration, distribution, and potential health benefi ts
40. Al-Anbari, A.K.H., and Hasan, M.A. (2015, January 22–23). Antioxidant activity in some citrus leaves and seeds ethanolic extracts. Proceedings of the International Conference on Advances in Agricultural, Biological and Environmental Sciences (AABES), London, UK.
41. Supercritical fluid extraction of limonoids and naringin from grapefruit (Citrus paradisi Macf.) seeds10.1016/j.foodchem.2007.04.062 ↗
42. Citrus flavonoids: Molecular structure, biological activity and nutritional properties: A review10.1016/j.foodchem.2006.11.054 ↗
43. Flavanones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature10.1016/j.jfca.2005.12.009 ↗
44. Rao, M.J., Wu, S., Duan, M., and Wang, L. (2021). Antioxidant Metabolites in Primitive, Wild, and Cultivated Citrus and Their Role in Stress Tolerance. Molecules, 26.10.3390/molecules26195801 ↗
45. Characterization and Metabolic Diversity of Flavonoids in Citrus Species10.1038/s41598-017-10970-2 ↗
46. Towards a comprehensive exploitation of citrus10.1016/j.tifs.2014.07.002 ↗
47. Before the injection—modern methods of sample preparation for separation techniques10.1016/S0021-9673(03)00511-9 ↗
48. Techniques for extraction of bioactive compounds from plant materials: A review10.1016/j.jfoodeng.2013.01.014 ↗
49. Impact of conventional and non-conventional processing on prickly pear (Opuntia spp.) and their derived products: From preservation of beverages to valorization of by-products10.1016/j.tifs.2017.07.012 ↗
50. Effect of thermal treatment, microwave, and pulsed electric field processing on the antimicrobial potential of açaí (Euterpe oleracea), stevia (Stevia rebaudiana Bertoni), and ginseng (Panax quinquefolius L.) extracts10.1016/j.foodcont.2018.02.022 ↗
51. Evaluation of new extraction approaches to obtain phenolic compound-rich extracts from Stevia rebaudiana Bertoni leaves10.1016/j.indcrop.2017.06.024 ↗
52. Uwineza, P.A., Gramza-Michałowska, A., Bryła, M., and Waśkiewicz, A. (2021). Antioxidant Activity and Bioactive Compounds of Lamium album Flower Extracts Obtained by Supercritical Fluid Extraction. Appl. Sci., 11.10.3390/app11167419 ↗
53. Near-infrared spectroscopic characterization of steviol glycosides extracted from Stevia rebaudiana Bertoni using high-power ultrasound and gas-phase plasma
54. New opportunities and perspectives of high pressure treatment to improve health and safety attributes of foods. A review10.1016/j.foodres.2015.05.015 ↗
55. Tamborrino, A., Urbani, S., Servili, M., Romaniello, R., Perone, C., and Leone, A. (2020). Pulsed electric fields for the treatment of olive pastes in the oil extraction process. Appl. Sci., 10.10.3390/app10010114 ↗
56. Zuorro, A., Lavecchia, R., González-Delgado, Á.D., García-Martinez, J.B., and L’Abbate, P. (2019). Optimization of enzyme-assisted extraction of flavonoids from corn husks. Processes, 7.10.3390/pr7110804 ↗
57. Maximizing total phenolics, total flavonoids contents and antioxidant activity of Moringa oleifera leaf extract by the appropriate extraction method10.1016/j.indcrop.2012.09.021 ↗
58. Ledesma-Escobar, C.A., Priego-Capote, F., and Luque de Castro, M.D. (2019). Chapter 9—Relevance and Analysis of Citrus Flavonoids. Polyphenols in Plants, Academic Press. [2nd ed.].10.1016/B978-0-12-813768-0.00009-8 ↗
59. Clean recovery of antioxidant flavonoids from citrus peel: Optimizing an aqueous ultrasound-assisted extraction method10.1016/j.foodchem.2009.05.075 ↗
60. McHugh, M., and Krukonis, V. (2013). Supercritical Fluid Extraction: Principles and Practice, Elsevier.
61. Supercritical fluid extraction using CO2: Main applications and future perspectives10.1080/01496395.2013.811422 ↗
62. Supercritical CO2 Extraction and Purification of Compounds with Antioxidant Activity10.1021/jf052858j ↗
63. Bioactive compounds in foods: Their role in the prevention of cardiovascular disease and cancer10.1016/S0002-9343(01)00995-0 ↗
64. In-vitro free radicals scavenging activity of Madhuca indica Gmel
65. Structural aspects of antioxidant activity of flavonoids10.1016/0891-5849(95)02047-0 ↗
66. Enhancement of antioxidant and anti-inflammatory activities of bioflavonoid rutin by complexation with transition metals10.1016/S0006-2952(01)00526-3 ↗
67. Natural antioxidants from residual sources10.1016/S0308-8146(00)00223-5 ↗
68. Antioxidant activity and phenolic composition of citrus peel and seed extracts10.1021/jf9709562 ↗
69. Naringin, a citrus flavonone, protects against radiation-induced chromosome damage in mouse bone marrow10.1093/mutage/geg001 ↗
70. Effective suppression of azoxymethane-induced aberrant crypt foci formation in mice with citrus peel flavonoids10.1002/mnfr.201200606 ↗
71. Formulated extract from multiple citrus peels impairs dendritic cell functions and attenuates allergic contact hypersensitivity10.1016/j.intimp.2014.02.005 ↗
72. The citrus flavonoid hesperidin induces p53 and inhibits NF-κB activation in order to trigger apoptosis in NALM-6 cells: Involvement of PPARγ-dependent mechanism10.1007/s00394-011-0187-2 ↗
73. The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells10.1016/j.jnutbio.2005.05.009 ↗
74. Didymin reverses phthalate ester-associated breast cancer aggravation in the breast cancer tumor microenvironment10.3892/ol.2015.4008 ↗
75. The apoptotic effect of hesperetin on human cervical cancer cells is mediated through cell cycle arrest, death receptor, and mitochondrial pathways10.1111/j.1472-8206.2012.01061.x ↗
76. Hesperidin increase cytotoxic effect of doxorubicin in MCF-7 cells
77. Cardioprotective and hepatoprotective effects of Citrus hystrix peels extract on rats model10.1016/S2221-1691(13)60079-9 ↗
78. Didymin prevents hyperglycemia-induced human umbilical endothelial cells dysfunction and death10.1016/j.bcp.2018.03.012 ↗
79. Dietary Polyphenols and the Prevention of Diseases10.1080/1040869059096 ↗
80. Comparative study of the vasorelaxant activity, superoxide-scavenging ability and cyclic nucleotide phosphodiesterase-inhibitory effects of hesperetin and hesperidin10.1007/s00210-004-0994-6 ↗
81. Implication of cyclic nucleotide phosphodiesterase inhibition in the vasorelaxant activity of the citrus-fruits flavonoid (+/-)-naringenin10.1055/s-2005-837774 ↗
82. Naringenin 7-O-cetyl ether as inhibitor of HMG-CoA reductase and modulator of plasma and hepatic lipids in high cholesterol-fed rats10.1016/S0968-0896(02)00441-8 ↗
83. Antiviral effect of flavonoids on human viruses10.1002/jmv.1890150110 ↗
84. Citrus flavonoid represses Salmonella pathogenicity island 1 and motility in S. Typhimurium LT210.1016/j.ijfoodmicro.2010.11.013 ↗
85. Suppression of bacterial cell-cell signalling, biofilm formation and type III secretion system by citrus flavonoids10.1111/j.1365-2672.2010.04677.x ↗
86. Antimicrobial effects of Citrus sinensis peel extracts against dental caries bacteria: An in vitro study
87. Evaluation of Skin Anti-aging Potential of Citrus reticulata Blanco Peel10.4103/0974-8490.182913 ↗
88. Bencheikh, N., Elbouzidi, A., Kharchoufa, L., Ouassou, H., Alami Merrouni, I., Mechchate, H., Es-Safi, I., Hano, C., Addi, M., and Bouhrim, M. (2021). Inventory of Medicinal Plants Used Traditionally to Manage Kidney Diseases in North-Eastern Morocco: Ethnobotanical Fieldwork and Pharmacological Evidence. Plants, 10.10.3390/plants10091966 ↗
89. Anti-degranulating activity in rat basophil leukemia RBL-2H3 cells of flavanone glycosides and their aglycones in citrus fruits10.1007/s11418-012-0699-y ↗
90. Potent activity of nobiletin-rich Citrus reticulata peel extract to facilitate cAMP/PKA/ERK/CREB signaling associated with learning and memory in cultured hippocampal neurons: Identification of the substances responsible for the pharmacological action10.1007/s00702-013-1025-x ↗
91. Flavonoid intake and risk of chronic diseases10.1093/ajcn/76.3.560 ↗
92. Benayad, O., Bouhrim, M., Tiji, S., Kharchoufa, L., Addi, M., Drouet, S., Hano, C., Lorenzo, J.M., Bendaha, H., and Bnouham, M. (2021). Phytochemical Profile, α-Glucosidase, and α-Amylase Inhibition Potential and Toxicity Evaluation of Extracts from Citrus aurantium (L) Peel, a Valuable By-Product from Northeastern Morocco. Biomolecules, 11.10.3390/biom11111555 ↗
93. Metabolic Engineering of plant cells for biotransformation of hesperedin into neohesperidin, a substrate for production of the low-calorie sweetener and flavor enhancer NHDC10.1021/jf051509m ↗
94. Sarni-Manchado, P., and Cheynier, V. (2006). Composés Phénoliques dans la Plante-Structure, Biosynthèse, Répartition et Rôles. Les Polyphénols en Agroalimentaire, Lavoisier.
95. Phytochemical characteristics of citrus peel and effect of conventional and nonconventional processing on phenolic compounds: A review10.1080/87559129.2016.1196489 ↗
96. Inhibition of Copper Corrosion by Flavonoids in Nitric Acid10.1155/2011/543498 ↗