Evaluating the bioactive effects of flavonoid hesperidin – A new literature data survey

Pękal A,, Dróżdż P, Biesaga M, Pyrzynska K. Screening of the antioxidant properties and polyphenol composition of aromatised green tea infusions. J Sci Food Agric 2012; 92(11): 2244−9.

Catalgol B, Batirel S, Taga Y, Ozer NK. Resveratrol: French Paradox Revisited. Front Pharmacol 2012; 3: 141.

Mink PJ, Scrafford CG, Barraj LM, Harnack L, Hong CP, Nettleton JA, et al. Flovonoid intake and cardiovascular disease wortality: a prospective study in postmenopausal women. Am J Clin Nutr 2007; 85(3): 895–909.

Buijsse B, Weikert C, Drogan D, Bergmann M, Boeing H. Chocolate consumption in relation to blood pressure and risk of cardi-ovascular disease in German adults. Eur Heart J 2010; 31(13): 1616–123.

Auclair S, Milenkovic D, Besson C, Chauvet S, Gueux E, Morand C, et al. Catechin reduces atherosclerotic lesion development in apo E-deficient mice: a transcriptomic study. Atherosclero-sis 2009; 204(2): e21–7.

Norata GD, Marchesi P, Passamonti S, Pirillo A, Violi F, Catapano AL. Anti-inflammatory and anti-atherogenic effects of cathe-chin, caffeic acid and trans-resveratrol in apolipoprotein E de-ficient mice. Atherosclerosis 2007; 191(2): 265–71.

Lippi G, Franchini M, Favaloro EJ, Targher G. Moderate red wine consumption and cardiovascular disease risk: beyond the "French paradox". Semin Thromb Hemost 2010; 36(1): 59−70.

Tapas AR, Sakarkar DM, Kakde RB. Flavonoids as Nutraceuti-cals: A Review. Trop J Pharm Res 2008; 7(3): 1089−99.

Melešev D, Kuntić V. Investigation of metal–flavonoid chelates and the determination of flavonoids via metal–flavonoid complexing reactions. J Serb Chem Soc 2007; 72(10): 921–39.

Andersen OM, Markham KR. Flavonoids: Chemistry, Biochemi-stry and Applications. Boca Raton, FL: CRC/Taylor & Fran-cis; 2006.

Bentsath A, Rusznyak S, Szent-Györgyi A. Vitamin nature of fla-vones. Nature 1936; 138: 798.

Middleton EJ, Kandaswami C. The impact of plant flavonoids on mammalian biology: Implications for immunity, inflammation and cancer. In: Harborne JB, editor. The flavonoids: Advances in research since 1986. London: Chapman and Hall; 2005. pp. 619–52.

Cushnie TP, Lamb AJ. Antimicrobial activity of flavonoids. Int J Antimicrob Agent 2005; 26(5): 343−56.

Dalgård C, Nielsen F, Morrow JD, Enghusen-Poulsen H, Jonung T, Hørder M, et al. Supplementation with orange and blackcurrant juice, but not vitamin E, improves inflammatory markers in patients with peripheral arterial disease. Br J Nutr 2009; 101(2): 263–9.

Middleton E, Kandaswami C. Effects of flavonoids on immune and inflammatory cell functions. Biochem Pharmacol 1992; 43(6): 1167–1179.

Tanaka T, Makita H, Kawabata K, Mori H. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the natu-rally occurring flavonoids, diosmin and hesperidin. Carcinoge-nesis 1997; 18(5): 957−65.

Lee JH, Kim YS, Lee CK, Lee HK, Han SS. Antiviral activity of some flavonoids on Herpes-simplex virus. Korean Pharmacog 1999; 30: 34−9.

Neuhouser ML. Dietary flavonoids and cancer risk: evidence from human population studies. Nutr Cancer 2004; 50(1): 1−7.

Ren W, Qiao Z, Wang H, Zhu L, Zhang L. Flavonoids: promis-ing anticancer agents. Med Res Rev 2003; 23(4): 519−34.

Bouskela E, Donyo KA. Effects of oral administration of puri-fied micronized flavonoid fraction on increased microvascular permeability induced by various agents and on ische-mia/reperfusion in diabetic hamsters. Int J Microcirc Clin Exp 1995; 15(6): 293−300.

McGregor L, Bellangeon M, Chignier E, Lerond L, Rousselle C, McGregor JL. Effect of a micronized purified flavonoid frac-tion on in vivo platelet functions in the rat. Thromb Res 1999; 94(4): 235−40.

Huxley RR, Neil HA. The relation between dietary flavonol intake and coronary heart disease mortality: a meta-analysis of prospective cohort studies. Eur J Clin Nutr 2003; 57(8): 904−8.

Hertog MG, Feskens EJ, Kromhout D. Antioxidant flavonols and coronary heart disease risk. Lancet 1997; 349(9053): 699.

Grassi D, Desideri G, Croce G, Tiberti S, Aggio A, Ferri C. Flavo-noids, vascular function and cardiovascular protection. Curr Pharm Des 2009; 15(10): 1072–84.

Manach C, Regerat F, Texier O, Agullo G, Demigne C, Remesy C, et al. Bioavailability, metabolism and physiologic impact of 4-oxo-flavonoids. Nutr Res 1996; 16(3): 517−44.

Ames BN, Shigenaga MK, Hagen TM. Oxidants, antioxidants, and the degenerative diseases of aging. Proc Natl Acad Sci 1993; 90(17): 7915−22.

Procházková D, Boušová I, Wilhelmová N. Antioxidant and proox-idant properties of flavonoids. Fitoterapia 2011; 82(4): 513–23.

Fenton HJH. Oxidation of tartaric acid in presence of iron. J Chem Soc Trans 1894; 65: 889−910.

Van Acker VS, van Balen GP, van der Berg DJ, van der Vijgh WJ. Influence of iron chelation on the antioxidant activity of flavonoids. Biochem Pharmacol 1998; 56(8): 935−43.

Afanas’ev IB, Dorozhko AI, Brodskii AV, Kostyuk VA, Potapovitch AI. Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxida-tion. Biochem Pharmacol 1989; 38(11): 1763−9.

Brown JE, Khodr H, Hider RC, Rice–Evans CA. Structural de-pendence of flavonoid interactions with Cu2+ ions: implications for their antioxidant properties. Biochem J 1998; 330(Pt 3): 1173−8.

Fiorani M, De Sanctis R, De Bellis R, Dacha M. Intracellular fla-vonoids as electron donors for extracellular ferricyanide reduc-tion in human erythrocytes. Free Radic Biol Med 2002; 32(1): 64−72.

Tajmir-Riahi HA, Diamantoglou S, Kanakis CD, Tarantilis PA, Po-lissiou MG. 2007. Flavonoids interactions with DNA and RNA: binding modes and antioxidative effects Acta Hort. (ISHS); 744: 195−204.

Mira L, Fernandez MT, Santos M, Rocha R, Florêncio MH, Jennings KR. Interactions of flavonoids with iron and copper ions: a mechanism for their antioxidant activity. Free Radic Res 2002; 36(11): 1199−208.

Kostyuk VA, Potapovich AI, Vladykovskaya EN, Korkina LG, Afanase’ev IB. Influence of metal ions on flavonoid protec-tion against asbestos-induced cell injury. Arch Biochem Bi-ophys 2001; 385(1): 129−37.

Moridani MY, Pourahmad J, Bui H, Siraki A, O'Brien PJ. Dietary flavonoid iron complexes as cytoprotective superoxide radical scavengers. Free Radic Biol Med 2003; 34(2): 243−53.

De Souza RF, De Giovani WF. Antioxidant properties of complexes of flavonoids with metal ions. Redox Rep 2004; 9(2): 97−104.

Afanas’ IB, Ostrakhovitch EA, Mikhal’chik EV, Ibragimova GA, Korkina LG. Enhancement of antioxidant and anti-inflammatory activities of bioflavonoid rutin by complexation with transition metals. Biochem Pharmacol 2001; 61(6): 677−84.

Barthe GA, Jourdan PS, Mclntosh CA, Mansell RL. Radioim-munossay for the quantitative determination of hesperidin and analysis of its distribution in Citrus sinensis. Phytochemistry 1988; 27(1): 249−54.

Leuzzi U, Caristi C, Panzera V, Licandro G. Flavonoids in pig-mented orange juice and second-pressure extracts. J Agric Food Chem 2000; 48(11): 5501–6.

AIJN – European Fruit Juice Association. What is the AIJN Code of Practice? Available from: http://www.aijn.org/pages/cop/cop.html

Manach C, Morand C, Gil-Izquierdo A, Bouteloup-Demange C, Rémésy C. Bioavailability in humans of the flavanones hesperi-din and narirutin after the ingestion of two doses of orange juice. Eur J Clin Nutr 2003; 57(2): 235−42.

Malešev D, Radović Z, Kuntić V, Kosanić M. Spectrophotometric determination of hesperidin by Al(III)-hesperidin complex in water-methanol solution. Anal Letters 1997; 30(5): 917−26.

Kuntić V, Kosanić M, Malešev D, Radović Z, Mioč U. Spectropho-tometric investigation of uranil(II)-hesperidin complex in 70% methanol. J Serb Chem Soc 1998; 63(7): 565−72.

Kuntić V, Blagojević S, Malešev D, Radović Z. Spectrophotometric investigation of Cu(II)-hesperidin complex in 50% ethanol. Pharmazie 1999; 54(7): 548−9.

Kuntić V, Filipović I, Vujić Z. Effects of rutin and hesperidin and their Al(III) and Cu(II) Complexes on in Vitro Plasma Coagu-lation Assays. Molecules 2011; 16(2): 1378−88.

Deng W, Fang X, Wu J. Flavonoids function as anti-oxidants: by scavenging reactive oxygen species or by chelating iron? Radiat Phys Chem 1997; 50(3): 271−6.

Suarez J, Herrera MD, Marhuenda E. In vitro scavenger and an-tioxidant properties of hesperidin and neohesperidin dihydro-chalcone. Phytomedicine 1998; 5(6): 469-473.

Jovanovic SV, Steenken S, Tosic M, Marjanovic B, Simic MG. Flavonoids as anti-oxidants. J Am Chem Soc 1994; 116(11): 4846−51.

Bonina F, Lanza M, Montenegro L, Puglisi C, Tomaino A, Trombetta D, et al. Flavonoids as potential protective agents against photo-oxidative skin damage. Int J Pharm 1996; 145(1−2): 87−94.

Nandakumar N, Balasubramanian MP. Hesperidin a citrus biof-lavonoid modulates hepatic biotransformation enzymes and enhances intrinsic antioxidants in experimental breast cancer rats challenged with 7, 12-dimethylbenz (a) anthracene. J Exp Ther Oncol 2012; 9(4): 321−35.

Hou M, Man M, Man W, Zhu W, Hupe M, Park K, et al. Topical hesperidin improves epidermal permeability barrier func-tion and epidermal differentiation in normal murine skin. Exp Dermatol 2012; 21(5): 337−40.

Garg A, Garg S, Zaneveld LJD, Singla AK. Chemistry and phar-macology of the citrus bioflavonoid hesperidin. Phytother Res 2001; 15(8): 655–69.

Johnsen SP, Overvad K, Stripp C, Tjonneland A, Husted SE, Sorensen HT. Intake of fruit and vegetables and the risk of ischemic stroke in a cohort of Danish men and women. Am J Clin Nutr 2003; 78(1): 57–64.

Dauchet L, Ferrieres J, Arveiler D, Yarnell JW, Gey F, Ducimetiere P, et al. Frequency of fruit and vegetable consumption and coro-nary heart disease in France and Northern Ireland: the PRIME study. Br J Nutr 2004; 92(6): 963–72.

Guarnieri S, Riso P, Porrini M. Orange juice vs vitamin C: effect on hydrogen peroxide-induced DNA damage in mononuclear blood cells. Br J Nutr 2007; 97(4): 639–43.

Johnston CS, Dancho CL, Strong GM. Orange juice ingestion and supplemental vitamin C are equally effective at reducing plasma lipid peroxidation in healthy adult women. J Am Coll Nutr 2003; 22(6): 519–23.

Ghanim H, Sia CL, Upadhyay M, Korzeniewski K, Viswanathan P, Abuaysheh S, et al. Orange juice neutralizes the proinflammatory effect of a high-fat, high-carbohydrate meal and prevents endotoxin increase and Toll-like receptor expression. Am J Clin Nutr 2010; 91(4): 940–9.

Sanchez-Moreno C, Cano MP, de Ancos B, Plaza L, Olmedilla B, Granado F, et al. Effect of orange juice intake on vitamin C concentrations and biomarkers of antioxidant status in hu-mans. Am J Clin Nutr 2003; 78(3): 454–60.

Kurowska EM, Spence JD, Jordan J, Wetmore S, Freeman DJ, Piché LA, et al. HDL-cholesterol-raising effect of orange juice in subjects with hypercholesterolemia. Am J Clin Nutr 2000; 72(5): 1095–100.

Reshef N, Hayari Y, Goren C, Boaz M, Madar Z, Knobler H. Anti-hypertensive effect of sweetie fruit in patients with stage I hypertension. Am J Hypertens 2005; 18(10): 1360–3.

Morand C, Dubray C, Milenkovic D, Lioger D, Martin JF, Scalbert A, et al. Hesperidin contributes to the vascular protective ef-fects of orange juice: a randomized crossover study in healthy volunteers. Am J Clin Nutr 2011; 93(1): 73–80.

Hooper L, Kroon PA, Rimm EB, Cohn JS, Harvey I, Le Cornu KA, et al. Flavonoids, flavonoid-rich foods, and cardiovascular risk: a meta-analysis of randomized controlled trials. Am J Clin Nutr 2008; 88(1): 38–50.

Demonty I, Lin Y, Zebregs YE, Vermeer MA, van der Knaap HC, Jakel M, et al. The citrus flavonoids hesperidin and naringin do not affect serum cholesterol in moderately hypercholestero-lemic men and women. J Nutr 2010; 140(9): 1615–20.

Weiss JF, Landauer MR. Protection against ionizing radiation by antioxidant nutrients and phytochemicals. Toxicology 2003; 189(1−2): 1–20.

Mates JM, Sanchez-Jimenez FM. Role of reactive oxygen species in apoptosis: implications for cancer therapy. Int J Biochem Cell Biol 2000; 32(2): 157–70.

Nambiar D, Rajamani P, Singh RP. Effects of phytochemicals on ionization radiation-mediated carcinogenesis and cancer thera-py. Mutat Res 2011; 728(3): 139–57.

Hosseinimehr SJ. Trends in the development of radioprotective agents. Drug Discov Today 2007; 12(19−20): 794–805.

Van Acker FA, Schouten O, Haenen RM, van der Vijh WJ, Bast A. Flavanoid can replace tocopherol as an antioxidant. FEBS Lett 2000; 473(2): 145–8.

Hosseinimehr SJ, Nemati A. Radioprotective effects of hesperidin against gamma irradiation in mouse bone marrow cells. Br J Radiol 2006; 79(941): 415–8.

Pradeep K, Park SH, Ko KC. Hesperidin a flavanoglycone pro-tects against γ-irradiation induced hepatocellular damage and oxidative stress in Sprague–Dawley rats. Eur J Pharmacol 2008; 587(1−3): 273–80.

Kalpana KB, Devipriya N, Srinivasan M, Vishwanathan P, Thayalan K, Menon VP. Evaluating the radioprotective effect of hesperi-din in the liver of Swiss albino mice. Eur J Pharmacol 2011; 658(2−3): 206–12.

Hosseinimehr SJ, Ahmadi A, Mahmoudzadeh A, Mohamadifar S. Radioprotective effects of Daflon against genotoxicity induced by gamma irradiation in human cultured lymphocytes. Environ Mol Mutagen 2009; 50(9): 749–52.

Hosseinimehr SJ, Mahmoudzadeh A, Ahmadi A, Mohamadifar S, Akhlaghpoor S. Radioprotective effects of hesperidin against genotoxicity induced by -irradiation in human lymphocytes. Mutagenesis 2009; 24(3): 233–5.

Kalpana KB, Devipriya N, Srinivasan M, Menon VP. Investigation of the radioprotective efficacy of hesperidin against gamma-radiation induced cellular damage in cultured human peripheral blood lymphocytes. Mutat Res 2009; 676(1−2): 54–61.

Kuntić V, Pejić N, Mićić S. Direct spectrophotometric determi-nation of hesperidin in pharmaceutical preparations. Acta Chim Slov 2012; 59(2): 436–41.