Isoquercitrin: Pharmacology, toxicology, and metabolism
Tài liệu tham khảo
Ader, 2000, Bioavailability and metabolism of the flavonol quercetin in the pig, Free Radic. Biol. Med., 28, 1056, 10.1016/S0891-5849(00)00195-7
Akiyama, 2000, Constituents of enzymatically modified isoquercitrin and enzymatically modified rutin (extract), J. Food Hyg. Soc. Jpn., 41, 54, 10.3358/shokueishi.41.54
Araujo, 2013, Bioconversion of quercetin and rutin and the cytotoxicity activities of the transformed products, Food Chem. Toxicol., 51, 93, 10.1016/j.fct.2012.09.015
Arts, 2002, Quercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine, J. Nutr., 132, 2823, 10.1093/jn/132.9.2823
Arts, 2004, The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides, Br. J. Nutr., 91, 841, 10.1079/BJN20041123
Beekmann, 2012, A state-of-the-art overview of the effect of metabolic conjugation on the biological activity of flavonoids, Food Funct., 3, 1008, 10.1039/c2fo30065f
Belkhir, 2013, Comparative analysis of tunisian wild Crataegus azarolus (yellow azarole) and Crataegus monogyna (red azarole) leaf, fruit, and traditionally derived syrup: phenolic profiles and antioxidant and antimicrobial activities of the aqueous-acetone extracts, J. Agric. Food Chem., 61, 9594, 10.1021/jf405285m
Berson, 1954, Blood volume in health and disease, Bull. N. Y. Acad. Med., 30, 750
Bock, 2000, Coordinate induction by antioxidants of UDP-glucuronosyltransferase UGT1A6 and the apical conjugate export pump MRP2 (multidrug resistance protein 2) in Caco-2 cells, Biochem. Pharmacol., 59, 467, 10.1016/S0006-2952(99)00366-4
Boligon, 2012, Protective effects of extracts and flavonoids isolated from Scutia buxifolia Reissek against chromosome damage in human lymphocytes exposed to hydrogen peroxide, Molecules, 17, 5757, 10.3390/molecules17055757
Boots, 2008, Health effects of quercetin: from antioxidant to nutraceutical, Eur. J. Pharmacol., 585, 325, 10.1016/j.ejphar.2008.03.008
Boušová, 2012, Inhibition and induction of glutathione S-transferases by flavonoids: possible pharmacological and toxicological consequences, Drug. Metab. Rev., 44, 267, 10.3109/03602532.2012.713969
Boyer, 2004, Uptake of quercetin and quercetin 3-glucoside from whole onion and apple peel extracts by Caco-2 cell monolayers, J. Agric. Food Chem., 52, 7172, 10.1021/jf030733d
Browning, 2005, Flavonoid glycosides inhibit oral cancer cell proliferation–role of cellular uptake and hydrolysis to the aglycones, J. Pharm. Pharmacol., 57, 1037, 10.1211/0022357056514
Butterweck, 2000, Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test, Planta Med., 66, 3, 10.1055/s-2000-11119
Calzada, 2007, Additional antiprotozoal flavonol glycosides of the aerial parts of Helianthemum glomeratum, Phytother. Res., 21, 78, 10.1002/ptr.2031
Cermak, 2008, Effect of dietary flavonoids on pathways involved in drug metabolism, Expert Opin. Drug Metab. Toxicol., 4, 17, 10.1517/17425255.4.1.17
Cermak, 2006, In vitro degradation of the flavonol quercetin and of quercetin glycosides in the porcine hindgut, Arch. Anim. Nutr., 60, 180, 10.1080/17450390500467695
Cermak, 2006, The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms, Curr. Drug Metab., 7, 729, 10.2174/138920006778520570
Cermak, 2003, The bioavailability of quercetin in pigs depends on the glycoside moiety and on dietary factors, J. Nutr., 133, 2802, 10.1093/jn/133.9.2802
Chang, 2005, Difference in absorption of the two structurally similar flavonoid glycosides, hyperoside and isoquercitrin, in rats, Eur. J. Pharm. Biopharm., 59, 549, 10.1016/j.ejpb.2004.10.004
Chaudhary, 2006, Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John’s wort, Toxicology, 217, 194, 10.1016/j.tox.2005.09.010
Chebil, 2007, Solubility of flavonoids in organic solvents, J. Chem. Eng. Data, 52, 1552, 10.1021/je7001094
Chebil, 2013, Elucidation of the kinetic behavior of quercetin, isoquercitrin, and rutin solubility by physicochemical and thermodynamic investigations, Ind. Eng. Chem. Res., 52, 1464, 10.1021/ie3029202
Choi, 2005, Enhanced diltiazem bioavailability after oral administration of diltiazem with quercetin to rabbits, Int. J. Pharm., 297, 1, 10.1016/j.ijpharm.2004.12.004
Chua, 2013, A review on plant-based rutin extraction methods and its pharmacological activities, J. Ethnopharmacol., 10.1016/j.jep.2013.10.036
Ciolino, 1999, Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially, Biochem. J., 340, 715, 10.1042/bj3400715
Crespy, 2002, Quercetin, but not its glycosides, is absorbed from the rat stomach, J. Agric. Food Chem., 50, 618, 10.1021/jf010919h
Crozier, 2010, Bioavailability of dietary flavonoids and phenolic compounds, Mol. Aspects Med., 31, 446, 10.1016/j.mam.2010.09.007
Cvetkovic, 2011, Effects of continuous UV-irradiation on the antioxidant activities of quercetin and rutin in solution in the presence of lecithin as the protective target, J. Serb. Chem. Soc., 76, 973, 10.2298/JSC101123089C
Dai, 2013, Preparative isolation and purification of seven main antioxidants from Eucommia ulmoides Oliv. (Du-zhong) leaves using HSCCC guided by DPPH-HPLC experiment, Food Chem., 139, 563, 10.1016/j.foodchem.2013.02.006
Dajas, 2012, Life or death: neuroprotective and anticancer effects of quercetin, J. Ethnopharmacol., 143, 383, 10.1016/j.jep.2012.07.005
Dangles, 2001, Binding of flavonoids to plasma proteins, Methods Enzymol., 335, 319, 10.1016/S0076-6879(01)35254-0
Day, 2000, Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase, FEBS Lett., 468, 166, 10.1016/S0014-5793(00)01211-4
Day, 2003, Absorption of quercetin-3-glucoside and quercetin-4’-glucoside in the rat small intestine: the role of lactase phlorizin hydrolase and the sodium-dependent glucose transporter, Biochem. Pharmacol., 65, 1199, 10.1016/S0006-2952(03)00039-X
De Santi, 2002, Inhibition of phenol sulfotransferase (SULT1A1) by quercetin in human adult and foetal livers, Xenobiotica, 32, 363, 10.1080/00498250110119108
Douglass, 1949, The isolation of isoquercitrin from the seed pods of Cercis canadensis, J. Am. Chem. Soc., 71, 2658, 10.1021/ja01176a016
Dragoni, 2006, Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro, Br. J. Pharmacol., 147, 765, 10.1038/sj.bjp.0706662
Dudka, 2005, Activity of NADPH-cytochrome P-450 reductase of the human heart, liver and lungs in the presence of (-)-epigallocatechin gallate, quercetin and resveratrol: an in vitro study, Basic Clin. Pharmacol. Toxicol., 97, 74, 10.1111/j.1742-7843.2005.pto_98.x
Ebert, 2007, Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate, Toxicol. Sci., 96, 227, 10.1093/toxsci/kfl147
Edenharder, 2003, Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102, Mutat. Res. Genet. Toxicol. Environ. Mutagen., 540, 1, 10.1016/S1383-5718(03)00114-1
Emura, 2007, Effect of enzymatically modified isoquercitrin in spontaneously hypertensive rats, J. Nutr. Sci. Vitaminol. (Tokyo), 53, 68, 10.3177/jnsv.53.68
Emura, K., Oka, H., Tanaka, H., 2010. Readily Water-Soluble Isoquercitrin Composition. US Patent 20120083460 A1.
Erlund, 2000, Pharmacokinetics of quercetin from quercetin aglycone and rutin in healthy volunteers, Eur. J. Clin. Pharmacol., 56, 545, 10.1007/s002280000197
Fabani, 2013, Pistachio (Pistacia vera var Kerman) from Argentinean cultivars. A natural product with potential to improve human health, J. Funct. Foods, 5, 1347, 10.1016/j.jff.2013.05.002
FDA, 2007. GRAS Notification – α-glycosyl isoquercitrin. <http://www.accessdata.fda.gov/scripts/fcn/gras_notices/grn000220.pdf> (Downloaded 25.09.13).
FDA, 2010. GRAS Notifice for high purity quercetin. <http://www.accessdata.fda.gov/scripts/fcn/gras_notices/grn341-1.pdf> (Downloaded 25.02.14).
Fernandez, 2005, Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4-induced contraction in guinea-pig airways, Eur. J. Pharmacol., 522, 108, 10.1016/j.ejphar.2005.08.046
Fox, 1984
Fujii, 2013, Effect of enzymatically modified isoquercitrin on preneoplastic liver cell lesions induced by thioacetamide promotion in a two-stage hepatocarcinogenesis model using rats, Toxicology, 305, 30, 10.1016/j.tox.2013.01.002
Galindo, 2012, Glucuronidated quercetin lowers blood pressure in spontaneously hypertensive rats via deconjugation, PLoS One, 7, e32673, 10.1371/journal.pone.0032673
Gasparotto Junior, 2012, Mechanisms underlying the diuretic effects of Tropaeolum majus L. extracts and its main component isoquercitrin, J. Ethnopharmacol., 141, 501, 10.1016/j.jep.2012.03.018
Gee, 2000, Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway, J. Nutr., 130, 2765, 10.1093/jn/130.11.2765
Gerstorferová, 2012, Recombinant α-l-rhamnosidase from Aspergillus terreus in selective trimming of rutin, Process. Biochem., 47, 828, 10.1016/j.procbio.2012.02.014
Gibellini, 2011, Quercetin and cancer chemoprevention, Evid. Based Complement. Alternat. Med., 2011, 591356, 10.1093/ecam/neq053
Ginsburg, 2011, Quantifying oxidant scavenging ability of blood, New Engl. J. Med., 364, 883, 10.1056/NEJMc1012584
Graefe, 2001, Pharmacokinetics and bioavailability of quercetin glycosides in humans, J. Clin. Pharmacol., 41, 492, 10.1177/00912700122010366
Guo, 2011, Anticonvulsant, antidepressant-like activity of Abelmoschus manihot ethanol extract and its potential active components in vivo, Phytomedicine, 18, 1250, 10.1016/j.phymed.2011.06.012
Hammer, 2007, Inhibition of prostaglandin E2 production by anti-inflammatory Hypericum perforatum extracts and constituents in RAW264.7 mouse macrophage cells, J. Agric. Food Chem., 55, 7323, 10.1021/jf0710074
Hansard, 1953, Blood volume of farm animals, J. Anim. Sci., 12, 402, 10.2527/jas1953.122402x
Harwood, 2007, A critical review of the data related to the safety of quercetin and lack of evidence of in vivo toxicity, including lack of genotoxic/carcinogenic properties, Food Chem. Toxicol., 45, 2179, 10.1016/j.fct.2007.05.015
Hasumura, 2004, Evaluation of the toxicity of enzymatically decomposed rutin with 13-weeks dietary administration to Wistar rats, Food Chem. Toxicol., 42, 439, 10.1016/j.fct.2003.10.006
He, 2013, A sensitive LC-MS/MS method for simultaneous determination of six flavonoids in rat plasma: application to a pharmacokinetic study of total flavonoids from mulberry leaves, J. Pharmaceut. Biomed. Anal., 84, 189, 10.1016/j.jpba.2013.06.019
Heim, 2002, Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships, J. Nutr. Biochem., 13, 572, 10.1016/S0955-2863(02)00208-5
Heinrich, 2013, Metabolic profiling of phenolic acids and oxidative stress markers after consumption of Lonicera caerulea L. fruit, J. Agric. Food Chem., 61, 4526, 10.1021/jf304150b
Hirano, 2009, Preventative effect of a flavonoid, enzymatically modified isoquercitrin on ocular symptoms of Japanese cedar pollinosis, Allergol. Int., 58, 373, 10.2332/allergolint.08-OA-0070
Hollman, 1995, Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers, Am. J. Clin. Nutr., 62, 1276, 10.1093/ajcn/62.6.1276
Hollman, 1996, Absorption and disposition kinetics of the dietary antioxidant quercetin in man, Free Radic. Biol. Med., 21, 703, 10.1016/0891-5849(96)00129-3
Hollman, 1997, Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man, FEBS Lett., 418, 152, 10.1016/S0014-5793(97)01367-7
Hsiu, 2002, Quercetin significantly decreased cyclosporin oral bioavailability in pigs and rats, Life Sci., 72, 227, 10.1016/S0024-3205(02)02235-X
Hunyadi, 2012, Chlorogenic acid and rutin play a major role in the in vivo anti-diabetic activity of Morus alba leaf extract on type II diabetic rats, PLoS One, 7, e50619, 10.1371/journal.pone.0050619
Jang, 2008, Effects of compounds isolated from the fruits of Rumex japonicus on the protein glycation, Chem. Biodivers., 5, 2718, 10.1002/cbdv.200890226
Jung, 2010, Isoquercitrin is the most effective antioxidant in the plant Thuja orientalis and able to counteract oxidative-induced damage to a transformed cell line (RGC-5 cells), Neurochem Int, 57, 713, 10.1016/j.neuint.2010.08.005
Juříková, 2012, Polyphenolic profile and biological activity of Chinese hawthorn (Crataegus pinnatifida BUNGE) fruits, Molecules, 17, 14490, 10.3390/molecules171214490
Kawai, 2009, Effect of enzymatically modified isoquercitrin, a flavonoid, on symptoms of Japanese cedar pollinosis: a randomized double-blind placebo-controlled trial, Int. Arch. Allergy Immunol., 149, 359, 10.1159/000205582
Kang, 2004, Mutat. Res.-Fund. Mol. M., 545, 37, 10.1016/j.mrfmmm.2003.08.002
Kim, 2013, Phenolic compounds with IL-6 inhibitory activity from Aster yomena, Arch. Pharm. Res.
Kim, 2013, Relative antioxidant activities of quercetin and its structurally related substances and their effects on NF-kappaB/CRE/AP-1 signaling in murine macrophages, Mol. Cells, 35, 410, 10.1007/s10059-013-0031-z
Kong, 2008, Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells, Toxicol. In Vitro, 22, 1742, 10.1016/j.tiv.2008.07.013
Koren, 2010, Polyphenols enhance total oxidant-scavenging capacities of human blood by binding to red blood cells, Exp. Biol. Med., 235, 689, 10.1258/ebm.2010.009370
Košinová, 2012, Positioning of antioxidant quercetin and its metabolites in lipid bilayer membranes: implication for their lipid-peroxidation inhibition, J. Phys. Chem. B, 116, 1309, 10.1021/jp208731g
Kottra, 2007, Flavonoid glycosides are not transported by the human Na+/glucose transporter when expressed in Xenopus laevis oocytes, but effectively inhibit electrogenic glucose uptake, J. Pharm. Exp. Ther., 322, 829, 10.1124/jpet.107.124040
Kraujalis, 2013, Antioxidant properties and preliminary evaluation of phytochemical composition of different anatomical parts of amaranth, Plant Foods Hum. Nutr., 68, 322, 10.1007/s11130-013-0375-8
Křen, V., Weignerová, L., Marhol, P., 2010. Method for Production of Quercetin-3-β-d-Glucopyranoside and of Rhamnose. Cz. pat. CZ 302216, November 18.
Křížková, 2009, The effects of selected flavonoids on cytochromes P450 in rat liver and small intestine, Interdiscip. Toxicol., 2, 201, 10.2478/v10102-009-0018-y
Kuhnau, 1976, The flavonoids. A class of semi-essential food components: their role in human nutrition, World Rev. Nutr. Diet, 24, 117, 10.1159/000399407
Kuwata, 2011, Concomitant apoptosis and regeneration of liver cells as a mechanism of liver-tumor promotion by beta-naphthoflavone involving TNF alpha-signaling due to oxidative cellular stress in rats, Toxicology, 283, 8, 10.1016/j.tox.2011.01.020
Kwon, 2007, Inhibition of the intestinal glucose transporter GLUT2 by flavonoids, FASEB J., 21, 366, 10.1096/fj.06-6620com
Kwon, 2010, Flavonoids from the buds of Rosa damascena inhibit the activity of 3-hydroxy-3-methylglutaryl-coenzyme A reductase and angiotensin I-converting enzyme, J. Agric. Food Chem., 58, 882, 10.1021/jf903515f
Lee, 1985, Blood volume in the rat, J. Nucl. Med., 26, 72
Lee, 2008, Effects of hyperin, isoquercitrin and quercetin on lipopolysaccharide-induced nitrite production in rat peritoneal macrophages, Phytother. Res., 22, 1552, 10.1002/ptr.2529
Lee, 2011, Persicaria hydropiper (L.) spach and its flavonoid components, isoquercitrin and isorhamnetin, activate the Wnt/beta-catenin pathway and inhibit adipocyte differentiation of 3T3-L1 cells, Phytother. Res., 25, 1629, 10.1002/ptr.3469
Lesser, 2004, Bioavailability of quercetin in pigs is influenced by the dietary fat content, J. Nutr., 134, 1508, 10.1093/jn/134.6.1508
Li, 2008, HPLC analysis and pharmacokinetic study of quercitrin and isoquercitrin in rat plasma after administration of Hypericum japonicum Thunb. extract, Biomed. Chromatogr., 22, 374, 10.1002/bmc.942
Li, 2009, Study on the interaction between 3 flavonoid compounds and α-amylase by fluorescence spectroscopy and enzymatic kinetics, J. Food Sci., 74, C199, 10.1111/j.1750-3841.2009.01080.x
Li, 2009, Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of α-glucosidase, J. Agric. Food Chem., 57, 11463, 10.1021/jf903083h
Li, 2011, In vivo antioxidative effect of isoquercitrin on cadmium-induced oxidative damage to mouse liver and kidney, Naunyn Schmied. Arch. Pharmacol., 383, 437, 10.1007/s00210-011-0613-2
Liu, 2010, Who is the king? The α-hydroxy-β-oxo-α, β-enone moiety or the catechol B ring: relationship between the structure of quercetin derivatives and their pro-oxidative abilities, Chem. Biodivers., 7, 236, 10.1002/cbdv.200900032
Lodi, 2008, Protective effect of quercetin and its metabolites in preventing impairment of human vascular cell functions, Polyphenols Comm., 1, 47
Loscalzo, 2009, Neuroactive flavonoid glycosides from Tilia petiolaris DC. extracts, Phytother. Res., 23, 1453, 10.1002/ptr.2800
Lu, 2013, Abelmoschi Corolla non-flavonoid components altered the pharmacokinetic profile of its flavonoids in rat, J. Ethnopharmacol., 148, 804, 10.1016/j.jep.2013.05.009
Lu, 2013, Identification of isoquercitrin metabolites produced by human intestinal bacteria using UPLC-Q-TOF/MS, Biomed. Chromatogr., 27, 509, 10.1002/bmc.2820
Lu, 2013, Degradation of rutin into isoquercitrin by Bacillus litoralis strain C44, IOSR J. Engin., 2, 1154, 10.9790/3021-020511541161
Makino, 2009, Enzymatically modified isoquercitrin, α-oligoglucosyl quercetin 3-O-glucoside, is absorbed more easily than other quercetin glycosides or aglycone after oral administration in rats, Biol. Pharm. Bull., 32, 2034, 10.1248/bpb.32.2034
Makris, 2002, An investigation on structural aspects influencing product formation in enzymic and chemical oxidation of quercetin and related flavonols, Food Chem., 77, 177, 10.1016/S0308-8146(01)00333-8
Males, Z., Saric, D., Bojic, M., 2013. Quantitative determination of flavonoids and chlorogenic acid in the leaves of Arbutus unedo L. using thin layer chromatography. J. Anal. Methods Chem., UNSP 385473, http://dx.doi.org/385410.381155/382013/385473.
Matsubara, 2004, Anti-angiogenic activity of quercetin and its derivatives, Lett. Drug Des. Discov., 1, 329, 10.2174/1570180043398533
Matsukawa, 2009, Nondigestible saccharides suppress the bacterial degradation of quercetin aglycone in the large intestine and enhance the bioavailability of quercetin glucoside in rats, J. Agric. Food Chem., 57, 9462, 10.1021/jf9024079
McCann, 2007, Food additives and hyperactive behaviour in 3-year-old and 8/9-year-old children in the community: a randomised, double-blinded, placebo-controlled trial, Lancet, 370, 1560, 10.1016/S0140-6736(07)61306-3
Menendez, 2011, Vascular deconjugation of quercetin glucuronide: The flavonoid paradox revealed?, Mol. Nutr. Food Res., 55, 1780, 10.1002/mnfr.201100378
Mohammadi-Bardbori, 2012, Quercetin, resveratrol, and curcumin are indirect activators of the aryl hydrocarbon receptor (AHR), Chem. Res. Toxicol., 25, 1878, 10.1021/tx300169e
Moon, 2006, Dietary flavonoids: effects on xenobiotic and carcinogen metabolism, Toxicol. In Vitro, 20, 187, 10.1016/j.tiv.2005.06.048
Morand, 2000, Quercetin 3-O-β-glucoside is better absorbed than other quercetin forms and is not present in rat plasma, Free Radic. Res., 33, 667, 10.1080/10715760000301181
Morikawa, 2003, Inhibitory effect of quercetin on carrageenan-induced inflammation in rats, Life Sci., 74, 709, 10.1016/j.lfs.2003.06.036
Morita, 2011, Suppressive effect of enzymatically modified isoquercitrin on phenobarbital-induced liver tumor promotion in rats, Arch. Toxicol., 85, 1475, 10.1007/s00204-011-0696-z
Motoyama, 2009, Atheroprotective and plaque-stabilizing effects of enzymatically modified isoquercitrin in atherogenic apoE-deficient mice, Nutrition, 25, 421, 10.1016/j.nut.2008.08.013
Murota, 2010, α-Oligoglucosylation of a sugar moiety enhances the bioavailability of quercetin glucosides in humans, Arch. Biochem. Biophys., 501, 91, 10.1016/j.abb.2010.06.036
Neveu, V., Perez-Jiménez, J., Vos, F., Crespy, V., du Chaffaut, L., Mennen, L., Knox, C., Eisner, R., Cruz, J., Wishart, D., Scalbert, A., 2010. Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database 2010.
Nishimura, 2010, Antioxidant enzymatically modified isoquercitrin or melatonin supplementation reduces oxidative stress-mediated hepatocellular tumor promotion of oxfendazole in rats, Arch. Toxicol., 84, 143, 10.1007/s00204-009-0497-9
Nugroho, 2014, Simultaneous quantification and peroxynitrite-scavenging activities of flavonoids in Polygonum aviculare L. herb, J. Pharm. Biomed. Anal., 89C, 93, 10.1016/j.jpba.2013.10.037
Obach, 2000, Inhibition of human cytochrome P450 enzymes by constituents of St. John’s Wort, an herbal preparation used in the treatment of depression, J. Pharmacol. Exp. Ther., 294, 88
Ofer, 2005, Modulation of drug transport by selected flavonoids: Involvement of P-gp and OCT?, Eur. J. Pharm. Sci., 25, 263, 10.1016/j.ejps.2005.03.001
Ohguchi, 2010, Inhibitory effects of flavonoid glycosides isolated from the peel of Japanese persimmon (Diospyros kaki ‘Fuyu’) on melanin biosynthesis, Biol. Pharm. Bull., 33, 122, 10.1248/bpb.33.122
Okamoto, 2005, Safety of quercetin for clinical application (Review), Int. J. Mol. Med., 16, 275
Okamura, 2011, Background Data for General Toxicology Parameters in RccHan™:WIST Rats at 8, 10, 19 and 32 Weeks of Age, J. Toxicol. Pathol., 24, 195, 10.1293/tox.24.195
Olennikov, 2013, Chemical investigation of Caragana arborescens shoots, Nat. Prod. Commun., 8, 585
Olthof, 2000, Bioavailabilities of quercetin-3-glucoside and quercetin-4′-glucoside do not differ in humans, J. Nutr., 130, 1200, 10.1093/jn/130.5.1200
Otake, 2000, Quercetin and resveratrol potently reduce estrogen sulfotransferase activity in normal human mammary epithelial cells, J. Steroid Biochem. Mol. Biol., 73, 265, 10.1016/S0960-0760(00)00073-X
Palazzolo, 2012, The flavonoid isoquercitrin promotes neurite elongation by reducing RhoA activity, PLoS One, 7, e49979, 10.1371/journal.pone.0049979
Panda, 2007, Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-O-glucoside, Biofactors, 31, 201, 10.1002/biof.5520310307
Paulke, 2006, Determination of St. John’s wort flavonoid-metabolites in rat brain through high performance liquid chromatography coupled with fluorescence detection, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 832, 109, 10.1016/j.jchromb.2005.12.043
Paulke, 2012, Isoquercitrin provides better bioavailability than quercetin: comparison of quercetin metabolites in body tissue and brain sections after six days administration of isoquercitrin and quercetin, Pharmazie, 67, 991
Paulo, 2008, The opposing effects of the flavonoids isoquercitrin and sissotrin, isolated from Pterospartum tridentatum, on oral glucose tolerance in rats, Phytother. Res., 22, 539, 10.1002/ptr.2403
Phang, 1993, Flavonol-stimulated efflux of 7,12-dimethylbenz(a)anthracene in multidrug-resistant breast cancer cells, Cancer Res., 53, 5977
Procházková, 2011, Antioxidant and prooxidant properties of flavonoids, Fitoterapia, 82, 513, 10.1016/j.fitote.2011.01.018
Pudzianowska, M., Gajewski, M., Przybył, Jarosław, L., Buraczyńska, A., Gaczkowska, O., Matuszczak, M., Dziechciarska, M., 2012. Influence of storage conditions on flavonoids content and antioxidant activity of selected shallot (Allium cepa var. Ascalonicum Backer) hybrid cultivars, Vegetable Crops Research Bulletin, p. 101.
Quideau, 2011, Plant polyphenols: chemical properties, biological activities, and synthesis, Angew. Chem. Int. Edit., 50, 586, 10.1002/anie.201000044
Rahden-Staron, 2001, Induction of rat liver cytochrome P450 isoenzymes CYP 1A and CYP2B by different fungicides, nitrofurans, and quercetin, Mutat. Res.-Gen. Tox. En., 498, 57, 10.1016/S1383-5718(01)00267-4
Rahman, 1994, Selective biotransformation of taxol to 6 α-hydroxytaxol by human cytochrome P450 2C8, Cancer Res., 54, 5543
Ramešová, 2012, On the stability of the bioactive flavonoids quercetin and luteolin under oxygen-free conditions, Anal. Bioanal. Chem., 402, 975, 10.1007/s00216-011-5504-3
Regasini, 2008, Flavonols from Pterogyne nitens and their evaluation as myeloperoxidase inhibitors, Phytochemistry, 69, 1739, 10.1016/j.phytochem.2008.01.006
Reinboth, 2010, Oral bioavailability of quercetin from different quercetin glycosides in dogs, Br. J. Nutr., 104, 198, 10.1017/S000711451000053X
Reuter, 2010, Oxidative stress, inflammation, and cancer: How are they linked?, Free Radic. Biol. Med., 49, 1603, 10.1016/j.freeradbiomed.2010.09.006
Rodeiro, 2008, Interactions of polyphenols with the P450 system: possible implications on human therapeutics, Mini-Rev. Med. Chem., 8, 97, 10.2174/138955708783498131
Rogerio, 2007, Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma, Inflamm. Res., 56, 402, 10.1007/s00011-007-7005-6
Rothwell, 2005, Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids, J. Agric. Food Chem., 53, 4355, 10.1021/jf0483669
Russo, 2012, The flavonoid quercetin in disease prevention and therapy: facts and fancies, Biochem. Pharmacol., 83, 6, 10.1016/j.bcp.2011.08.010
Salem, 2010, Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters, Process Biochem., 45, 382, 10.1016/j.procbio.2009.10.012
Salim, 2004, Lack of carcinogenicity of enzymatically modified isoquercitrin in F344/DuCrj rats, Food Chem. Toxicol., 42, 1949, 10.1016/j.fct.2004.07.010
Salucci, 2002, Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2), Br. J. Cancer, 86, 1645, 10.1038/sj.bjc.6600295
Schneider, 1999, Anaerobic transformation of quercetin-3-glucoside by bacteria from the human intestinal tract, Arch. Microbiol., 171, 81, 10.1007/s002030050682
Schneider, 2000, Degradation of quercetin-3-glucoside in gnotobiotic rats associated with human intestinal bacteria, J. Appl. Microbiol., 89, 1027, 10.1046/j.1365-2672.2000.01209.x
Schoefer, 2003, Anaerobic degradation of flavonoids by Clostridium orbiscindens, Appl. Environ. Microbiol., 69, 5849, 10.1128/AEM.69.10.5849-5854.2003
Sergent, 2009, CYP1A1 and CYP3A4 modulation by dietary flavonoids in human intestinal Caco-2 cells, Toxicol. Lett., 191, 216, 10.1016/j.toxlet.2009.09.002
Serra, 2012, Metabolic pathways of the colonic metabolism of flavonoids (flavonols, flavones and flavanones) and phenolic acids, Food Chem., 130, 383, 10.1016/j.foodchem.2011.07.055
Sesink, 2001, Quercetin glucuronides but not glucosides are present in human plasma after consumption of quercetin-3-glucoside or quercetin-4’-glucoside, J. Nutr., 131, 1938, 10.1093/jn/131.7.1938
Shapiro, 1997, Effect of quercetin on Hoechst 33342 transport by purified and reconstituted P-glycoprotein, Biochem. Pharmacol., 53, 587, 10.1016/S0006-2952(96)00826-X
Sharma, 2013, Rutin: therapeutic potential and recent advances in drug delivery, Expert. Opin. Investig. Drugs, 22, 1063, 10.1517/13543784.2013.805744
Shibano, 2008, Antioxidant constituents in the dayflower (Commelina communis L.) and their α-glucosidase-inhibitory activity, J. Nat. Med., 62, 349, 10.1007/s11418-008-0244-1
Shimada, 2010, Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by β-naphthoflavone, Toxicology, 268, 213, 10.1016/j.tox.2009.12.019
Slimestad, 2003, Flavonoids in buds and young needles of Picea, Pinus and Abies, Biochem. Sys. Ecol., 31, 1247, 10.1016/S0305-1978(03)00018-8
Snijman, 2007, The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions, Mutat. Res., 631, 111, 10.1016/j.mrgentox.2007.03.009
Soberon, 2010, Free radical scavenging activities and inhibition of inflammatory enzymes of phenolics isolated from Tripodanthus acutifolius, J. Ethnopharmacol., 130, 329, 10.1016/j.jep.2010.05.015
Sokolová, 2011, The oxidation mechanism of the antioxidant quercetin in nonaqueous media, Electrochim. Acta, 56, 7421, 10.1016/j.electacta.2011.04.121
Sokolová, 2012, The oxidation of natural flavonoid quercetin, Chem. Commun., 48, 3433, 10.1039/c2cc18018a
Soundararajan, 2008, Quercetin-3-glucoside protects neuroblastoma (SH-SY5Y) cells in vitro against oxidative damage by inducing sterol regulatory element-binding protein-2-mediated cholesterol biosynthesis, J. Biol. Chem., 283, 2231, 10.1074/jbc.M703583200
Spencer, 1999, The small intestine can both absorb and glucuronidate luminal flavonoids, FEBS Lett., 458, 224, 10.1016/S0014-5793(99)01160-6
Sumi, 2013, Quercetin glucosides promote ischemia-induced angiogenesis, but do not promote tumor growth, Life Sci., 93, 814, 10.1016/j.lfs.2013.09.005
Tamura, 2010, Fifty-two week chronic toxicity of enzymatically decomposed rutin in Wistar rats, Food Chem. Toxicol., 48, 2312, 10.1016/j.fct.2010.05.065
Taniai, 2013, Ochratoxin A induces karyomegaly and cell cycle aberrations in renal tubular cells without relation to induction of oxidative stress responses in rats, Toxicol. Lett., 224, 64, 10.1016/j.toxlet.2013.10.001
Tanigawa, 2007, Action of Nrf2 and Keap1 in ARE-mediated NQO1 expression by quercetin, Free Radic. Biol. Med., 42, 1690, 10.1016/j.freeradbiomed.2007.02.017
Tribolo, 2008, Comparative effects of quercetin and its predominant human metabolites on adhesion molecule expression in activated human vascular endothelial cells, Atherosclerosis, 197, 50, 10.1016/j.atherosclerosis.2007.07.040
Trouillas, 2006, A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: the specificity of the 3-OH site, Food Chem., 97, 679, 10.1016/j.foodchem.2005.05.042
Vacek, 2012, Biotransformation of flavonols and taxifolin in hepatocyte in vitro systems as determined by liquid chromatography with various stationary phases and electrospray ionization-quadrupole time-of-flight mass spectrometry, J. Chromatogr. B, 899, 109, 10.1016/j.jchromb.2012.05.009
van der Woude, 2003, Biphasic modulation of cell proliferation by quercetin at concentrations physiologically relevant in humans, Cancer Lett., 200, 41, 10.1016/S0304-3835(03)00412-9
van Zanden, 2003, Inhibition of human glutathione S-transferase P1–1 by the flavonoid quercetin, Chem. Biol. Interact., 145, 139, 10.1016/S0009-2797(02)00250-8
Velazquez, 2009, Antisecretory activity from the flowers of Chiranthodendron pentadactylon and its flavonoids on intestinal fluid accumulation induced by Vibrio cholerae toxin in rats, J. Ethnopharmacol., 126, 455, 10.1016/j.jep.2009.09.016
Vlase, 2013, Phytochemical analysis of Allium fistulosum L. and A. ursinum L, Dig. J. Nanomater. Bios., 8, 457
Vlase, 2013, Chemical constituents of three Allium species from Romania, Molecules, 18, 114, 10.3390/molecules18010114
Vrba, 2012, Quercetin, quercetin glycosides and taxifolin differ in their ability to induce AhR activation and CYP1A1 expression in HepG2 cells, Phytother. Res., 26, 1746, 10.1002/ptr.4637
Vrba, 2013, A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway, J. Med. Chem., 56, 856, 10.1021/jm3013344
Walle, 2004, Absorption and metabolism of flavonoids, Free Radic. Biol. Med., 36, 829, 10.1016/j.freeradbiomed.2004.01.002
Walle, 2001, Carbon dioxide is the major metabolite of quercetin in humans, J. Nutr., 131, 2648, 10.1093/jn/131.10.2648
Wang, 2004, Lethal quercetin-digoxin interaction in pigs, Life Sci., 74, 1191, 10.1016/j.lfs.2003.06.044
Wang, 2011, A comparison of acidic and enzymatic hydrolysis of rutin, Afr. J. Biotechnol., 10, 1460
Weignerová, 2012, Preparatory production of quercetin-3-β-d-glucopyranoside using alkali-tolerant thermostable α-L-rhamnosidase from Aspergillus terreus, Bioresource Technol., 115, 222, 10.1016/j.biortech.2011.08.029
Williamson, 2005, In vitro biological properties of flavonoid conjugates found in vivo, Free Radic. Res., 39, 457, 10.1080/10715760500053610
Wolffram, 2002, Quercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine, J. Nutr., 132, 630, 10.1093/jn/132.4.630
Xu, 2005, Induction of phase I, II and III drug metabolism/transport by xenobiotics, Arch. Pharm. Res., 28, 249, 10.1007/BF02977789
Xue, 2011, Identification of the potential active components of Abelmoschus manihot in rat blood and kidney tissue by microdialysis combined with ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 879, 317, 10.1016/j.jchromb.2010.12.016
Yan, 2013, Stabilization of grape skin anthocyanins by copigmentation with enzymatically modified isoquercitrin (EMIQ) as a copigment, Food Res. Int., 50, 603, 10.1016/j.foodres.2011.04.007
Yang, 2012, Prooxidant activities of quercetin, p-courmaric acid and their derivatives analysed by quantitative structure-activity relationship, Food Chem., 131, 508, 10.1016/j.foodchem.2011.09.014
Yang, 2013, Phenolic antioxidants from Rosa soulieana flowers, Nat. Prod. Res., 27, 2055, 10.1080/14786419.2013.811660
Yokohira, 2008, Antioxidant effects of flavonoids used as food additives (purple corn color, enzymatically modified isoquercitrin, and isoquercitrin) on liver carcinogenesis in a rat medium-term bioassay, J. Food Sci., 73, C561, 10.1111/j.1750-3841.2008.00862.x
Zhou, 2011, A sensitive LC-MS-MS method for simultaneous quantification of two structural isomers, hyperoside and isoquercitrin: application to pharmacokinetic studies, Chromatographia, 73, 353, 10.1007/s10337-010-1879-0
Zuo, 2006, Intestinal absorption of hawthorn flavonoids – in vitro, in situ and in vivo correlations, Life Sci., 79, 2455, 10.1016/j.lfs.2006.08.014