Isoquercitrin: Pharmacology, toxicology, and metabolism

Food and Chemical Toxicology

Volumn 68, Issue , 2014, Pages 267-282

  Valentová, Kateřina ^a,b   Vrba, Jiří ^a   Bancířová, Martina ^a   Ulrichová, Jitka ^a   Křen, Vladimír ^b  

^a PALACKÝ UNIVERSITY   (Czech Republic)

^b INSTITUTE OF MICROBIOLOGY   (Czech Republic)

Author keywords

Bioavailability; Biological activity; Enzymatically modified isoquercitrin; Quercetin 3 glucoside; Quercetin 3 O d glucopyranoside; Safety

Indexed keywords

CARBON DIOXIDE; ISOQUERCITRIN; QUERCETIN; RUTOSIDE;

ALLERGIC REACTION; AREA UNDER THE CURVE; BIOLOGICAL ACTIVITY; CARDIOVASCULAR DISEASE; DEGLYCOSYLATION; DIABETES MELLITUS; DRUG BIOAVAILABILITY; DRUG HALF LIFE; DRUG METABOLISM; DRUG TRANSFORMATION; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; INTESTINE; LIVER; MAXIMUM PLASMA CONCENTRATION; NEOPLASM; OXIDATIVE STRESS; PHARMACOLOGY; REVIEW; TOXICOLOGY; ANALOGS AND DERIVATIVES; ANIMAL; BIOAVAILABILITY; BIOTRANSFORMATION; CHEMISTRY; CHEMOPROPHYLAXIS; DISEASE MODEL; HUMAN; PHYSICAL CHEMISTRY; PROCEDURES; TOXICITY;

ANIMALS; BIOLOGICAL AVAILABILITY; BIOTRANSFORMATION; CHEMOPREVENTION; DISEASE MODELS, ANIMAL; HUMANS; PHYSICOCHEMICAL PHENOMENA; QUERCETIN;

EID: 84898835161     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2014.03.018     Document Type: Review

References (196)

1. Ader P., Wessmann A., Wolffram S. Bioavailability and metabolism of the flavonol quercetin in the pig. Free Radic. Biol. Med. 2000, 28:1056-1067.
2. Akiyama T., Washino T., Yamada T., Koda T., Maitani T. Constituents of enzymatically modified isoquercitrin and enzymatically modified rutin (extract). J. Food Hyg. Soc. Jpn. 2000, 41:54-60.
3. Araujo K.C., de M.B.C.E.M., Pazini F., Valadares M.C., de Oliveira V. Bioconversion of quercetin and rutin and the cytotoxicity activities of the transformed products. Food Chem. Toxicol. 2013, 51:93-96.
4. Arts I.C., Sesink A.L., Hollman P.C. Quercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine. J. Nutr. 2002, 132:2823. author reply 2824.
5. Arts I.C., Sesink A.L., Faassen-Peters M., Hollman P.C. 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. 2004, 91:841-847.
6. Beekmann K., Actis-Goretta L., van Bladeren P.J., Dionisi F., Destaillats F., Rietjens I.M. A state-of-the-art overview of the effect of metabolic conjugation on the biological activity of flavonoids. Food Funct. 2012, 3:1008-1018.
7. Belkhir M., Rebai O., Dhaouadi K., Congiu F., Tuberoso C.I., Amri M., Fattouch S. 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. 2013, 61:9594-9601.
8. Berson S.A. Blood volume in health and disease. Bull. N. Y. Acad. Med. 1954, 30:750-776.
9. Bock K.W., Eckle T., Ouzzine M., Fournel-Gigleux S. 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. 2000, 59:467-470.
10. Boligon A.A., Sagrillo M.R., Machado L.F., de Souza Filho O., Machado M.M., da Cruz I.B., Athayde M.L. Protective effects of extracts and flavonoids isolated from Scutia buxifolia Reissek against chromosome damage in human lymphocytes exposed to hydrogen peroxide. Molecules 2012, 17:5757-5769.
11. Boots A.W., Haenen G.R., Bast A. Health effects of quercetin: from antioxidant to nutraceutical. Eur. J. Pharmacol. 2008, 585:325-337.
12. Boušová I., Skálová L. Inhibition and induction of glutathione S-transferases by flavonoids: possible pharmacological and toxicological consequences. Drug. Metab. Rev. 2012, 44:267-286.
13. Boyer J., Brown D., Liu R.H. Uptake of quercetin and quercetin 3-glucoside from whole onion and apple peel extracts by Caco-2 cell monolayers. J. Agric. Food Chem. 2004, 52:7172-7179.
14. Browning A.M., Walle U.K., Walle T. Flavonoid glycosides inhibit oral cancer cell proliferation-role of cellular uptake and hydrolysis to the aglycones. J. Pharm. Pharmacol. 2005, 57:1037-1042.
15. Butterweck V., Jurgenliemk G., Nahrstedt A., Winterhoff H. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Med. 2000, 66:3-6.
16. Calzada F., Alanis A.D. Additional antiprotozoal flavonol glycosides of the aerial parts of Helianthemum glomeratum. Phytother. Res. 2007, 21:78-80.
17. Cermak R. Effect of dietary flavonoids on pathways involved in drug metabolism. Expert Opin. Drug Metab. Toxicol. 2008, 4:17-35.
18. Cermak R., Breves G.M. In vitro degradation of the flavonol quercetin and of quercetin glycosides in the porcine hindgut. Arch. Anim. Nutr. 2006, 60:180-189.
19. Cermak R., Wolffram S. The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms. Curr. Drug Metab. 2006, 7:729-744.
20. Cermak R., Landgraf S., Wolffram S. The bioavailability of quercetin in pigs depends on the glycoside moiety and on dietary factors. J. Nutr. 2003, 133:2802-2807.
21. Chang Q., Zuo Z., Chow M.S.S., Ho W.K.K. Difference in absorption of the two structurally similar flavonoid glycosides, hyperoside and isoquercitrin, in rats. Eur. J. Pharm. Biopharm. 2005, 59:549-555.
22. Chaudhary A., Willett K.L. Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort. Toxicology 2006, 217:194-205.
23. Chebil L., Humeau C., Anthoni J., Dehez F., Engasser J.M., Ghoul M. Solubility of flavonoids in organic solvents. J. Chem. Eng. Data 2007, 52:1552-1556.
24. Chebil L., Bouroukba M., Gaiani C., Charbonel C., Khaldi M., Engasser J.M., Ghoul M. Elucidation of the kinetic behavior of quercetin, isoquercitrin, and rutin solubility by physicochemical and thermodynamic investigations. Ind. Eng. Chem. Res. 2013, 52:1464-1470.
25. Choi J.S., Li X.G. Enhanced diltiazem bioavailability after oral administration of diltiazem with quercetin to rabbits. Int. J. Pharm. 2005, 297:1-8.
26. Chua L.S. A review on plant-based rutin extraction methods and its pharmacological activities. J. Ethnopharmacol. 2013, 10.1016/j.jep.2013.10.036.
27. Ciolino H.P., Daschner P.J., Yeh G.C. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochem. J. 1999, 340:715-722.
28. Crespy V., Morand C., Besson C., Manach C., Demigne C., Remesy C. Quercetin, but not its glycosides, is absorbed from the rat stomach. J. Agric. Food Chem. 2002, 50:618-621.
29. Crozier A., Del Rio D., Clifford M.N. Bioavailability of dietary flavonoids and phenolic compounds. Mol. Aspects Med. 2010, 31:446-467.
30. Cvetkovic D., Markovic D., Cvetkovic D., Radovanovic B. 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. 2011, 76:973-985.
31. Dai X., Huang Q., Zhou B., Gong Z., Liu Z., Shi S. Preparative isolation and purification of seven main antioxidants from Eucommia ulmoides Oliv. (Du-zhong) leaves using HSCCC guided by DPPH-HPLC experiment. Food Chem. 2013, 139:563-570.
32. Dajas F. Life or death: neuroprotective and anticancer effects of quercetin. J. Ethnopharmacol. 2012, 143:383-396.
33. Dangles O., Dufour C., Manach C., Morand C., Remesy C. Binding of flavonoids to plasma proteins. Methods Enzymol. 2001, 335:319-333.
34. Day A.J., Canada F.J., Diaz J.C., Kroon P.A., McLauchlan R., Faulds C.B., Plumb G.W., Morgan M.R., Williamson G. Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase. FEBS Lett. 2000, 468:166-170.
35. Day A.J., Gee J.M., DuPont M.S., Johnson I.T., Williamson G. 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. 2003, 65:1199-1206.
36. De Santi C., Pietrabissa A., Mosca F., Rane A., Pacifici G.M. Inhibition of phenol sulfotransferase (SULT1A1) by quercetin in human adult and foetal livers. Xenobiotica 2002, 32:363-368.
37. Douglass C.D., Howard W.L., Wender S.H. The isolation of isoquercitrin from the seed pods of Cercis canadensis. J. Am. Chem. Soc. 1949, 71:2658-2659.
38. Dragoni S., Gee J., Bennett R., Valoti M., Sgaragli G. Red wine alcohol promotes quercetin absorption and directs its metabolism towards isorhamnetin and tamarixetin in rat intestine in vitro. Br. J. Pharmacol. 2006, 147:765-771.
39. Dudka J., Jodynis-Liebert J., Korobowicz E., Burdan F., Korobowicz A., Szumilo J., Tokarska E., Klepacz R., Murias M. 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. 2005, 97:74-79.
40. Ebert B., Seidel A., Lampen A. Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate. Toxicol. Sci. 2007, 96:227-236.
41. Edenharder R., Grunhage D. 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. 2003, 540:1-18.
42. Emura K., Yokomizo A., Toyoshi T., Moriwaki M. Effect of enzymatically modified isoquercitrin in spontaneously hypertensive rats. J. Nutr. Sci. Vitaminol. (Tokyo) 2007, 53:68-74.
43. Emura, K., Oka, H., Tanaka, H., 2010. Readily Water-Soluble Isoquercitrin Composition. US Patent 20120083460 A1.
44. Erlund I., Kosonen T., Alfthan G., Maenpaa J., Perttunen K., Kenraali J., Parantainen J., Aro A. Pharmacokinetics of quercetin from quercetin aglycone and rutin in healthy volunteers. Eur. J. Clin. Pharmacol. 2000, 56:545-553.
45. Fabani M.P., Luna L., Baroni M.V., Monferran M.V., Ighani M., Tapia A., Wunderlin D.A., Feresin G.E. Pistachio (Pistacia vera var Kerman) from Argentinean cultivars. A natural product with potential to improve human health. J. Funct. Foods 2013, 5:1347-1356.
46. FDA, 2007. GRAS Notification - α-glycosyl isoquercitrin.(Downloaded 25.09.13). http://www.accessdata.fda.gov/scripts/fcn/gras_notices/grn000220.pdf.
47. FDA, 2010. GRAS Notifice for high purity quercetin.(Downloaded 25.02.14). http://www.accessdata.fda.gov/scripts/fcn/gras_notices/grn341-1.pdf.
48. Fernandez J., Reyes R., Ponce H., Oropeza M., Vancalsteren M.R., Jankowski C., Campos M.G. Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4-induced contraction in guinea-pig airways. Eur. J. Pharmacol. 2005, 522:108-115.
49. Fox J.G., Cohen B.J., Loew F.M. Laboratory Animal Medicine 1984, Academic Press, Orlando, Fla.
50. Fujii Y., Kimura M., Ishii Y., Yamamoto R., Morita R., Hayashi S.M., Suzuki K., Shibutani M. Effect of enzymatically modified isoquercitrin on preneoplastic liver cell lesions induced by thioacetamide promotion in a two-stage hepatocarcinogenesis model using rats. Toxicology 2013, 305:30-40.
51. Galindo P., Rodriguez-Gomez I., Gonzalez-Manzano S., Duenas M., Jimenez R., Menendez C., Vargas F., Tamargo J., Santos-Buelga C., Perez-Vizcaino F., Duarte J. Glucuronidated quercetin lowers blood pressure in spontaneously hypertensive rats via deconjugation. PLoS One 2012, 7:e32673.
52. Gasparotto Junior A., Prando T.B., Leme Tdos S., Gasparotto F.M., Lourenco E.L., Rattmann Y.D., Da Silva-Santos J.E., Kassuya C.A., Marques M.C. Mechanisms underlying the diuretic effects of Tropaeolum majus L. extracts and its main component isoquercitrin. J. Ethnopharmacol. 2012, 141:501-509.
53. Gee J.M., DuPont M.S., Day A.J., Plumb G.W., Williamson G., Johnson I.T. Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. J. Nutr. 2000, 130:2765-2771.
54. Gerstorferová D., Fliedrová B., Halada P., Marhol P., Křen V., Weignerová L. Recombinant α-l-rhamnosidase from Aspergillus terreus in selective trimming of rutin. Process. Biochem. 2012, 47:828-835.
55. Gibellini L., Pinti M., Nasi M., Montagna J.P., De Biasi S., Roat E., Bertoncelli L., Cooper E.L., Cossarizza A. Quercetin and cancer chemoprevention. Evid. Based Complement. Alternat. Med. 2011, 2011:591356.
56. Ginsburg I., Kohen R., Koren E. Quantifying oxidant scavenging ability of blood. New Engl. J. Med. 2011, 364:883-885.
57. Graefe E.U., Wittig J., Mueller S., Riethling A.K., Uehleke B., Drewelow B., Pforte H., Jacobasch G., Derendorf H., Veit M. Pharmacokinetics and bioavailability of quercetin glycosides in humans. J. Clin. Pharmacol. 2001, 41:492-499.
58. Guo J., Xue C., Duan J.A., Qian D., Tang Y., You Y. Anticonvulsant, antidepressant-like activity of Abelmoschus manihot ethanol extract and its potential active components in vivo. Phytomedicine 2011, 18:1250-1254.
59. Hammer K.D., Hillwig M.L., Solco A.K., Dixon P.M., Delate K., Murphy P.A., Wurtele E.S., Birt D.F. Inhibition of prostaglandin E2 production by anti-inflammatory Hypericum perforatum extracts and constituents in RAW264.7 mouse macrophage cells. J. Agric. Food Chem. 2007, 55:7323-7331.
60. Hansard S.L., Butler W.O., Comar C.L., Hobbs C.S. Blood volume of farm animals. J. Anim. Sci. 1953, 12:402-413.
61. Harwood M., Danielewska-Nikiel B., Borzelleca J.F., Flamm G.W., Williams G.M., Lines T.C. 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. 2007, 45:2179-2205.
62. Hasumura M., Yasuhara K., Tamura T., Imai T., Mitsumori K., Hirose M. Evaluation of the toxicity of enzymatically decomposed rutin with 13-weeks dietary administration to Wistar rats. Food Chem. Toxicol. 2004, 42:439-444.
63. He J., Feng Y., Ouyang H.-Z., Yu B., Chang Y.-X., Pan G.-X., Dong G.-Y., Wang T., Gao X.-M. 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. 2013, 84:189-195.
64. Heim K.E., Tagliaferro A.R., Bobilya D.J. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J. Nutr. Biochem. 2002, 13:572-584.
65. Heinrich J., Valentova K., Vacek J., Palikova I., Zatloukalova M., Kosina P., Ulrichova J., Vrbkova J., Simanek V. Metabolic profiling of phenolic acids and oxidative stress markers after consumption of Lonicera caerulea L. fruit. J. Agric. Food Chem. 2013, 61:4526-4532.
66. Hirano T., Kawai M., Arimitsu J., Ogawa M., Kuwahara Y., Hagihara K., Shima Y., Narazaki M., Ogata A., Koyanagi M., Kai T., Shimizu R., Moriwaki M., Suzuki Y., Ogino S., Kawase I., Tanaka T. Preventative effect of a flavonoid, enzymatically modified isoquercitrin on ocular symptoms of Japanese cedar pollinosis. Allergol. Int. 2009, 58:373-382.
67. Hollman P.C., de Vries J.H., van Leeuwen S.D., Mengelers M.J., Katan M.B. Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am. J. Clin. Nutr. 1995, 62:1276-1282.
68. Hollman P.C., vd Gaag M., Mengelers M.J., van Trijp J.M., de Vries J.H., Katan M.B. Absorption and disposition kinetics of the dietary antioxidant quercetin in man. Free Radic. Biol. Med. 1996, 21:703-707.
69. Hollman P.C., van Trijp J.M., Buysman M.N., van der Gaag M.S., Mengelers M.J., de Vries J.H., Katan M.B. Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man. FEBS Lett. 1997, 418:152-156.
70. Hsiu S.L., Hou Y.C., Wang Y.H., Tsao C.W., Su S.F., Chao P.D. Quercetin significantly decreased cyclosporin oral bioavailability in pigs and rats. Life Sci. 2002, 72:227-235.
71. Hunyadi A., Martins A., Hsieh T.J., Seres A., Zupko I. 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 2012, 7:e50619.
72. Jang D.S., Kim J.M., Kim J., Yoo J.L., Kim Y.S., Kim J.S. Effects of compounds isolated from the fruits of Rumex japonicus on the protein glycation. Chem. Biodivers. 2008, 5:2718-2723.
73. Jung S.H., Kim B.J., Lee E.H., Osborne N.N. 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 2010, 57:713-721.
74. Juříková T., Sochor J., Rop O., Mlcek J., Balla S., Szekeres L., Adam V., Kizek R. Polyphenolic profile and biological activity of Chinese hawthorn (Crataegus pinnatifida BUNGE) fruits. Molecules 2012, 17:14490-14509.
75. Kawai M., Hirano T., Arimitsu J., Higa S., Kuwahara Y., Hagihara K., Shima Y., Narazaki M., Ogata A., Koyanagi M., Kai T., Shimizu R., Moriwaki M., Suzuki Y., Ogino S., Kawase I., Tanaka T. Effect of enzymatically modified isoquercitrin, a flavonoid, on symptoms of Japanese cedar pollinosis: a randomized double-blind placebo-controlled trial. Int. Arch. Allergy Immunol. 2009, 149:359-368.
76. Kang I.H., Kim H.J., Oh H., Park Y.I., Dong M.S. Biphasic effects of the flavonoids quercetin and naringenin on the metabolic activation of 2-amino-3,5-dimethylimidazo[4,5-f]quinoline by Salmonella typhimurium TA1538 co-expressing human cytochrome P450 1A2, NADPH-cytochrome P450 reductase, and cytochrome b(5). Mutat. Res.-Fund. Mol. M. 2004, 545:37-47.
77. Kim A.R., Jin Q., Jin H.G., Ko H.J., Woo E.R. Phenolic compounds with IL-6 inhibitory activity from Aster yomena. Arch. Pharm. Res. 2013.
78. Kim B.H., Choi J.S., Yi E.H., Lee J.K., Won C., Ye S.K., Kim M.H. 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 2013, 35:410-420.
79. Kong C.S., Kim Y.A., Kim M.M., Park J.S., Kim J.A., Kim S.K., Lee B.J., Nam T.J., Seo Y. Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells. Toxicol. In Vitro 2008, 22:1742-1748.
80. Koren E., Kohen R., Ginsburg I. Polyphenols enhance total oxidant-scavenging capacities of human blood by binding to red blood cells. Exp. Biol. Med. 2010, 235:689-699.
81. Košinová P., Berka K., Wykes M., Otyepka M., Trouillas P. Positioning of antioxidant quercetin and its metabolites in lipid bilayer membranes: implication for their lipid-peroxidation inhibition. J. Phys. Chem. B 2012, 116:1309-1318.
82. Kottra G., Daniel H. 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. 2007, 322:829-883.
83. Kraujalis P., Venskutonis P.R., Kraujaliene V., Pukalskas A. Antioxidant properties and preliminary evaluation of phytochemical composition of different anatomical parts of amaranth. Plant Foods Hum. Nutr. 2013, 68:322-328.
84. 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.
85. Křížková J., Burdová K., Stiborová M., Křen V., Hodek P. The effects of selected flavonoids on cytochromes P450 in rat liver and small intestine. Interdiscip. Toxicol. 2009, 2:201-204.
86. Kuhnau J. The flavonoids. A class of semi-essential food components: their role in human nutrition. World Rev. Nutr. Diet 1976, 24:117-191.
87. Kuwata K., Shibutani M., Hayashi H., Shimamoto K., Hayashi S.M., Suzuki K., Mitsumori K. 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 2011, 283:8-17.
88. Kwon O., Eck P., Chen S., Corpe C.P., Lee J.H., Kruhlak M., Levine M. Inhibition of the intestinal glucose transporter GLUT2 by flavonoids. FASEB J. 2007, 21:366-377.
89. Kwon E.K., Lee D.Y., Lee H., Kim D.O., Baek N.I., Kim Y.E., Kim H.Y. 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. 2010, 58:882-886.
90. Lee H.B., Blaufox M.D. Blood volume in the rat. J. Nucl. Med. 1985, 26:72-76.
91. Lee S., Park H.S., Notsu Y., Ban H.S., Kim Y.P., Ishihara K., Hirasawa N., Jung S.H., Lee Y.S., Lim S.S., Park E.H., Shin K.H., Seyama T., Hong J., Ohuchi K. Effects of hyperin, isoquercitrin and quercetin on lipopolysaccharide-induced nitrite production in rat peritoneal macrophages. Phytother. Res. 2008, 22:1552-1556.
92. Lee S.H., Kim B., Oh M.J., Yoon J., Kim H.Y., Lee K.J., Lee J.D., Choi K.Y. 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. 2011, 25:1629-1635.
93. Lesser S., Cermak R., Wolffram S. Bioavailability of quercetin in pigs is influenced by the dietary fat content. J. Nutr. 2004, 134:1508-1511.
94. Li J., Wang Z.W., Zhang L., Liu X., Chen X.H., Bi K.S. HPLC analysis and pharmacokinetic study of quercitrin and isoquercitrin in rat plasma after administration of Hypericum japonicum Thunb. extract. Biomed. Chromatogr. 2008, 22:374-378.
95. Li Y., Gao F., Shan F., Bian J., Zhao C. Study on the interaction between 3 flavonoid compounds and α-amylase by fluorescence spectroscopy and enzymatic kinetics. J. Food Sci. 2009, 74:C199-C203.
96. Li Y.Q., Zhou F.C., Gao F., Bian J.S., Shan F. Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of α-glucosidase. J. Agric. Food Chem. 2009, 57:11463-11468.
97. Li R., Yuan C., Dong C., Shuang S., Choi M.M. In vivo antioxidative effect of isoquercitrin on cadmium-induced oxidative damage to mouse liver and kidney. Naunyn Schmied. Arch. Pharmacol. 2011, 383:437-445.
98. Liu P.Y., Li K., Zhang J., Zhang D.W., Lin H.H., Yu X.Q. 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. 2010, 7:236-244.
99. Lodi F., Tribolo S., Needs P.W., Kroon P.A., Hughes D.A. Protective effect of quercetin and its metabolites in preventing impairment of human vascular cell functions. Polyphenols Comm. 2008, 1:47-48.
100. Loscalzo L.M., Wasowski C., Marder M. Neuroactive flavonoid glycosides from Tilia petiolaris DC. extracts. Phytother. Res. 2009, 23:1453-1457.
101. Lu L.L., Qian D.W., Guo J.M., Qian Y.F., Xu B.Y., Sha M., Duan J.A. Abelmoschi Corolla non-flavonoid components altered the pharmacokinetic profile of its flavonoids in rat. J. Ethnopharmacol. 2013, 148:804-811.
102. Lu L.L., Qian D.W., Yang J., Jiang S., Guo J.M., Shang E.X., Duan J.A. Identification of isoquercitrin metabolites produced by human intestinal bacteria using UPLC-Q-TOF/MS. Biomed. Chromatogr. 2013, 27:509-514.
103. Lu Z., Wang J., Lin S., Zhan Y. Degradation of rutin into isoquercitrin by Bacillus litoralis strain C44. IOSR J. Engin. 2013, 2:1154-1161.
104. Makino T., Shimizu R., Kanemaru M., Suzuki Y., Moriwaki M., Mizukami H. 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. 2009, 32:2034-2040.
105. Makris D.P., Rossiter J.T. An investigation on structural aspects influencing product formation in enzymic and chemical oxidation of quercetin and related flavonols. Food Chem. 2002, 77:177-185.
106. 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.
107. Matsubara K., Ishihara K., Mizushina Y., Mori M., Nakajima N. Anti-angiogenic activity of quercetin and its derivatives. Lett. Drug Des. Discov. 2004, 1:329-333.
108. Matsukawa N., Matsumoto M., Shinoki A., Hagio M., Inoue R., Hara H. 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. 2009, 57:9462-9468.
109. McCann D., Barrett A., Cooper A., Crumpler D., Dalen L., Grimshaw K., Kitchin E., Lok K., Porteous L., Prince E., Sonuga-Barke E., Warner J.O., Stevenson J. 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 2007, 370:1560-1567.
110. Menendez C., Duenas M., Galindo P., Gonzalez-Manzano S., Jimenez R., Moreno L., Zarzuelo M.J., Rodriguez-Gomez I., Duarte J., Santos-Buelga C., Perez-Vizcaino F. Vascular deconjugation of quercetin glucuronide: The flavonoid paradox revealed?. Mol. Nutr. Food Res. 2011, 55:1780-1790.
111. Mohammadi-Bardbori A., Bengtsson J., Rannug U., Rannug A., Wincent E. Quercetin, resveratrol, and curcumin are indirect activators of the aryl hydrocarbon receptor (AHR). Chem. Res. Toxicol. 2012, 25:1878-1884.
112. Moon Y.J., Wang X., Morris M.E. Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. Toxicol. In Vitro 2006, 20:187-210.
113. Morand C., Manach C., Crespy V., Remesy C. Quercetin 3-O-β-glucoside is better absorbed than other quercetin forms and is not present in rat plasma. Free Radic. Res. 2000, 33:667-676.
114. Morikawa K., Nonaka M., Narahara M., Torii I., Kawaguchi K., Yoshikawa T., Kumazawa Y., Morikawa S. Inhibitory effect of quercetin on carrageenan-induced inflammation in rats. Life Sci. 2003, 74:709-721.
115. Morita R., Shimamoto K., Ishii Y., Kuwata K., Ogawa B., Imaoka M., Hayashi S., Suzuki K., Shibutani M., Mitsumori K. Suppressive effect of enzymatically modified isoquercitrin on phenobarbital-induced liver tumor promotion in rats. Arch. Toxicol. 2011, 85:1475-1484.
116. Motoyama K., Koyama H., Moriwaki M., Emura K., Okuyama S., Sato E., Inoue M., Shioi A., Nishizawa Y. Atheroprotective and plaque-stabilizing effects of enzymatically modified isoquercitrin in atherogenic apoE-deficient mice. Nutrition 2009, 25:421-427.
117. Murota K., Matsuda N., Kashino Y., Fujikura Y., Nakamura T., Kato Y., Shimizu R., Okuyama S., Tanaka H., Koda T., Sekido K., Terao J. α-Oligoglucosylation of a sugar moiety enhances the bioavailability of quercetin glucosides in humans. Arch. Biochem. Biophys. 2010, 501:91-97.
118. 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.
119. Nishimura J., Saegusa Y., Dewa Y., Jin M., Kawai M., Kemmochi S., Harada T., Hayashi S., Shibutani M., Mitsumori K. Antioxidant enzymatically modified isoquercitrin or melatonin supplementation reduces oxidative stress-mediated hepatocellular tumor promotion of oxfendazole in rats. Arch. Toxicol. 2010, 84:143-153.
120. Nugroho A., Kim E.J., Choi J.S., Park H.J. Simultaneous quantification and peroxynitrite-scavenging activities of flavonoids in Polygonum aviculare L. herb. J. Pharm. Biomed. Anal. 2014, 89C:93-98.
121. Obach R.S. 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. 2000, 294:88-95.
122. Ofer M., Wolffram S., Koggel A., Spahn-Langguth H., Langguth P. Modulation of drug transport by selected flavonoids: Involvement of P-gp and OCT?. Eur. J. Pharm. Sci. 2005, 25:263-271.
123. Ohguchi K., Nakajima C., Oyama M., Iinuma M., Itoh T., Akao Y., Nozawa Y., Ito M. Inhibitory effects of flavonoid glycosides isolated from the peel of Japanese persimmon (Diospyros kaki 'Fuyu') on melanin biosynthesis. Biol. Pharm. Bull. 2010, 33:122-124.
124. Okamoto T. Safety of quercetin for clinical application (Review). Int. J. Mol. Med. 2005, 16:275-278.
125. Okamura T., Suzuki S., Ogawa T., Kobayashi J., Kusuoka O., Hatayama K., Mochizuki M., Hoshiya T., Okazaki S., Tamura K. Background Data for General Toxicology Parameters in RccHan™:WIST Rats at 8, 10, 19 and 32 Weeks of Age. J. Toxicol. Pathol. 2011, 24:195-205.
126. Olennikov D.N., Tankhaeva L.M., Partilkhaev V.V. Chemical investigation of Caragana arborescens shoots. Nat. Prod. Commun. 2013, 8:585-586.
127. Olthof M.R., Hollman P.C.H., Vree T.B., Katan M.B. Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans. J. Nutr. 2000, 130:1200-1203.
128. Otake Y., Nolan A.L., Walle U.K., Walle T. Quercetin and resveratrol potently reduce estrogen sulfotransferase activity in normal human mammary epithelial cells. J. Steroid Biochem. Mol. Biol. 2000, 73:265-270.
129. Palazzolo G., Horvath P., Zenobi-Wong M. The flavonoid isoquercitrin promotes neurite elongation by reducing RhoA activity. PLoS One 2012, 7:e49979.
130. Panda S., Kar A. Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-O-glucoside. Biofactors 2007, 31:201-210.
131. Paulke A., Schubert-Zsilavecz M., Wurglics M. 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. 2006, 832:109-113.
132. Paulke A., Eckert G.P., Schubert-Zsilavecz M., Wurglics M. 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 2012, 67:991-996.
133. Paulo A., Martins S., Branco P., Dias T., Borges C., Rodrigues A.I., Costa Mdo C., Teixeira A., Mota-Filipe H. The opposing effects of the flavonoids isoquercitrin and sissotrin, isolated from Pterospartum tridentatum, on oral glucose tolerance in rats. Phytother. Res. 2008, 22:539-543.
134. Phang J.M., Poore C.M., Lopaczynska J., Yeh G.C. Flavonol-stimulated efflux of 7,12-dimethylbenz(a)anthracene in multidrug-resistant breast cancer cells. Cancer Res. 1993, 53:5977-5981.
135. Procházková D., Boušová I., Wilhelmová N. Antioxidant and prooxidant properties of flavonoids. Fitoterapia 2011, 82:513-523.
136. 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.
137. Quideau S., Deffieux D., Douat-Casassus C., Pouységu L. Plant polyphenols: chemical properties, biological activities, and synthesis. Angew. Chem. Int. Edit. 2011, 50:586-621.
138. Rahden-Staron I., Czeczot H., Szumilo M. Induction of rat liver cytochrome P450 isoenzymes CYP 1A and CYP2B by different fungicides, nitrofurans, and quercetin. Mutat. Res.-Gen. Tox. En. 2001, 498:57-66.
139. Rahman A., Korzekwa K.R., Grogan J., Gonzalez F.J., Harris J.W. Selective biotransformation of taxol to 6 α-hydroxytaxol by human cytochrome P450 2C8. Cancer Res. 1994, 54:5543-5546.
140. Ramešová S., Sokolová R., Degano I., Bulíčkova J., Žabka J., Gál M. On the stability of the bioactive flavonoids quercetin and luteolin under oxygen-free conditions. Anal. Bioanal. Chem. 2012, 402:975-982.
141. Regasini L.O., Vellosa J.C., Silva D.H., Furlan M., de Oliveira O.M., Khalil N.M., Brunetti I.L., Young M.C., Barreiro E.J., Bolzani V.S. Flavonols from Pterogyne nitens and their evaluation as myeloperoxidase inhibitors. Phytochemistry 2008, 69:1739-1744.
142. Reinboth M., Wolffram S., Abraham G., Ungemach F.R., Cermak R. Oral bioavailability of quercetin from different quercetin glycosides in dogs. Br. J. Nutr. 2010, 104:198-203.
143. Reuter S., Gupta S.C., Chaturvedi M.M., Aggarwal B.B. Oxidative stress, inflammation, and cancer: How are they linked?. Free Radic. Biol. Med. 2010, 49:1603-1616.
144. Rodeiro I., Donato M.T., Lahoz A., Garrido G., Delgado R., Gomez-Lechon M.J. Interactions of polyphenols with the P450 system: possible implications on human therapeutics. Mini-Rev. Med. Chem. 2008, 8:97-106.
145. Rogerio A.P., Kanashiro A., Fontanari C., da Silva E.V., Lucisano-Valim Y.M., Soares E.G., Faccioli L.H. Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma. Inflamm. Res. 2007, 56:402-408.
146. Rothwell J.A., Day A.J., Morgan M.R. Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids. J. Agric. Food Chem. 2005, 53:4355-4360.
147. Russo M., Spagnuolo C., Tedesco I., Bilotto S., Russo G.L. The flavonoid quercetin in disease prevention and therapy: facts and fancies. Biochem. Pharmacol. 2012, 83:6-15.
148. Salem J.H., Humeau C., Chevalot I., Harscoat-Schiavo C., Vanderesse R., Blanchard F., Fick M. Effect of acyl donor chain length on isoquercitrin acylation and biological activities of corresponding esters. Process Biochem. 2010, 45:382-389.
149. Salim E.I., Kaneko M., Wanibuchi H., Morimura K., Fukushima S. Lack of carcinogenicity of enzymatically modified isoquercitrin in F344/DuCrj rats. Food Chem. Toxicol. 2004, 42:1949-1969.
150. Salucci M., Stivala L.A., Maiani G., Bugianesi R., Vannini V. Flavonoids uptake and their effect on cell cycle of human colon adenocarcinoma cells (Caco2). Br. J. Cancer 2002, 86:1645-1651.
151. Schneider H., Schwiertz A., Collins M.D., Blaut M. Anaerobic transformation of quercetin-3-glucoside by bacteria from the human intestinal tract. Arch. Microbiol. 1999, 171:81-91.
152. Schneider H., Simmering R., Hartmann L., Pforte H., Blaut M. Degradation of quercetin-3-glucoside in gnotobiotic rats associated with human intestinal bacteria. J. Appl. Microbiol. 2000, 89:1027-1037.
153. Schoefer L., Mohan R., Schwiertz A., Braune A., Blaut M. Anaerobic degradation of flavonoids by Clostridium orbiscindens. Appl. Environ. Microbiol. 2003, 69:5849-5854.
154. Sergent T., Dupont I., Van der Heiden E., Scippo M.L., Pussemier L., Larondelle Y., Schneider Y.J. CYP1A1 and CYP3A4 modulation by dietary flavonoids in human intestinal Caco-2 cells. Toxicol. Lett. 2009, 191:216-222.
155. Serra A., Macia A., Romero M.P., Reguant J., Ortega N., Motilva M.J. Metabolic pathways of the colonic metabolism of flavonoids (flavonols, flavones and flavanones) and phenolic acids. Food Chem. 2012, 130:383-393.
156. Sesink A.L., O'Leary K.A., Hollman P.C. Quercetin glucuronides but not glucosides are present in human plasma after consumption of quercetin-3-glucoside or quercetin-4'-glucoside. J. Nutr. 2001, 131:1938-1941.
157. Shapiro A.B., Ling V. Effect of quercetin on Hoechst 33342 transport by purified and reconstituted P-glycoprotein. Biochem. Pharmacol. 1997, 53:587-596.
158. Sharma S., Ali A., Ali J., Sahni J.K., Baboota S. Rutin: therapeutic potential and recent advances in drug delivery. Expert. Opin. Investig. Drugs 2013, 22:1063-1079.
159. Shibano M., Kakutani K., Taniguchi M., Yasuda M., Baba K. Antioxidant constituents in the dayflower (Commelina communis L.) and their α-glucosidase-inhibitory activity. J. Nat. Med. 2008, 62:349-353.
160. Shimada Y., Dewa Y., Ichimura R., Suzuki T., Mizukami S., Hayashi S., Shibutani M., Mitsumori K. Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by β-naphthoflavone. Toxicology 2010, 268:213-218.
161. Slimestad R. Flavonoids in buds and young needles of Picea, Pinus and Abies. Biochem. Sys. Ecol. 2003, 31:1247-1255.
162. Snijman P.W., Swanevelder S., Joubert E., Green I.R., Gelderblom W.C. The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions. Mutat. Res. 2007, 631:111-123.
163. Soberon J.R., Sgariglia M.A., Sampietro D.A., Quiroga E.N., Vattuone M.A. Free radical scavenging activities and inhibition of inflammatory enzymes of phenolics isolated from Tripodanthus acutifolius. J. Ethnopharmacol. 2010, 130:329-333.
164. Sokolová R., Degano I., Ramešová S., Bulíčková J., Hromadová M., Gál M., Fiedler J., Valášek M. The oxidation mechanism of the antioxidant quercetin in nonaqueous media. Electrochim. Acta 2011, 56:7421-7427.
165. Sokolová R., Ramešová S., Degano I., Hromadová M., Gál M., Žabka J. The oxidation of natural flavonoid quercetin. Chem. Commun. 2012, 48:3433-3435.
166. Soundararajan R., Wishart A.D., Rupasinghe H.P., Arcellana-Panlilio M., Nelson C.M., Mayne M., Robertson G.S. 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. 2008, 283:2231-2245.
167. Spencer J.P.E., Chowrimootoo G., Choudhury R., Debnam E.S., Srai S.K., Rice-Evans C. The small intestine can both absorb and glucuronidate luminal flavonoids. FEBS Lett. 1999, 458:224-230.
168. Sumi M., Tateishi N., Shibata H., Ohki T., Sata M. Quercetin glucosides promote ischemia-induced angiogenesis, but do not promote tumor growth. Life Sci. 2013, 93:814-819.
169. Tamura T., Mitsumori K., Muto S., Kasahara H., Kobayashi S., Okuhara Y., Hayashi M., Nagasawa T., Onozato T., Kuroda J. Fifty-two week chronic toxicity of enzymatically decomposed rutin in Wistar rats. Food Chem. Toxicol. 2010, 48:2312-2318.
170. Taniai E., Yafune A., Nakajima M., Hayashi S.-M., Nakane F., Itahashi M., Shibutani M. Ochratoxin A induces karyomegaly and cell cycle aberrations in renal tubular cells without relation to induction of oxidative stress responses in rats. Toxicol. Lett. 2013, 224:64-72.
171. Tanigawa S., Fujii M., Hou D.X. Action of Nrf2 and Keap1 in ARE-mediated NQO1 expression by quercetin. Free Radic. Biol. Med. 2007, 42:1690-1703.
172. Tribolo S., Lodi F., Connor C., Suri S., Wilson V.G., Taylor M.A., Needs P.W., Kroon P.A., Hughes D.A. Comparative effects of quercetin and its predominant human metabolites on adhesion molecule expression in activated human vascular endothelial cells. Atherosclerosis 2008, 197:50-56.
173. Trouillas P., Marsal P., Siri D., Lazzaroni R., Duroux J.L. A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: the specificity of the 3-OH site. Food Chem. 2006, 97:679-688.
174. Vacek J., Papoušková B., Kosina P., Vrba J., Křen V., Ulrichová J. 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 2012, 899:109-115.
175. van der Woude H., Gliszczynska-Swiglo A., Struijs K., Smeets A., Alink G.M., Rietjens I.M. Biphasic modulation of cell proliferation by quercetin at concentrations physiologically relevant in humans. Cancer Lett. 2003, 200:41-47.
176. van Zanden J.J., Ben Hamman O., van Iersel M.L., Boeren S., Cnubben N.H., Lo Bello M., Vervoort J., van Bladeren P.J., Rietjens I.M. Inhibition of human glutathione S-transferase P1-1 by the flavonoid quercetin. Chem. Biol. Interact. 2003, 145:139-148.
177. Velazquez C., Calzada F., Esquivel B., Barbosa E., Calzada S. Antisecretory activity from the flowers of Chiranthodendron pentadactylon and its flavonoids on intestinal fluid accumulation induced by Vibrio cholerae toxin in rats. J. Ethnopharmacol. 2009, 126:455-458.
178. Vlase L., Parvu M., Parvu E.A., Toiu A. Phytochemical analysis of Allium fistulosum L. and A. ursinum L. Dig. J. Nanomater. Bios. 2013, 8:457-467.
179. Vlase L., Parvu M., Parvu E.A., Toiu A. Chemical constituents of three Allium species from Romania. Molecules 2013, 18:114-127.
180. Vrba J., Křen V., Vacek J., Papoušková B., Ulrichová J. Quercetin, quercetin glycosides and taxifolin differ in their ability to induce AhR activation and CYP1A1 expression in HepG2 cells. Phytother. Res. 2012, 26:1746-1752.
181. Vrba J., Gažák R., Kuzma M., Papoušková B., Vacek J., Weiszenstein M., Křen V., Ulrichová J. A novel semisynthetic flavonoid 7-O-galloyltaxifolin upregulates heme oxygenase-1 in RAW264.7 cells via MAPK/Nrf2 pathway. J. Med. Chem. 2013, 56:856-866.
182. Walle T. Absorption and metabolism of flavonoids. Free Radic. Biol. Med. 2004, 36:829-837.
183. Walle T., Walle U.K., Halushka P.V. Carbon dioxide is the major metabolite of quercetin in humans. J. Nutr. 2001, 131:2648-2652.
184. Wang Y.H., Chao P.D., Hsiu S.L., Wen K.C., Hou Y.C. Lethal quercetin-digoxin interaction in pigs. Life Sci. 2004, 74:1191-1197.
185. Wang J., Zhao L.L., Sun G.X., Liang Y., Wu F.A., Chen Z.L., Cui S.M. A comparison of acidic and enzymatic hydrolysis of rutin. Afr. J. Biotechnol. 2011, 10:1460-1466.
186. Weignerová L., Marhol P., Gerstorferová D., Křen V. Preparatory production of quercetin-3-β-d-glucopyranoside using alkali-tolerant thermostable α-L-rhamnosidase from Aspergillus terreus. Bioresource Technol. 2012, 115:222-227.
187. Williamson G., Barron D., Shimoi K., Terao J. In vitro biological properties of flavonoid conjugates found in vivo. Free Radic. Res. 2005, 39:457-469.
188. Wolffram S., Blöck M., Ader P. Quercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine. J. Nutr. 2002, 132:630-635.
189. Xu C., Li C.Y., Kong A.N. Induction of phase I, II and III drug metabolism/transport by xenobiotics. Arch. Pharm. Res. 2005, 28:249-268.
190. Xue C., Guo J., Qian D., Duan J.A., Shang E., Shu Y., Lu Y. 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. 2011, 879:317-325.
191. Yan Q., Zhang L., Zhang X., Liu X., Yuan F., Hou Z., Gao Y. Stabilization of grape skin anthocyanins by copigmentation with enzymatically modified isoquercitrin (EMIQ) as a copigment. Food Res. Int. 2013, 50:603-609.
192. Yang B., Chen F., Hua Y.L., Huang S.S., Lin S., Wen L.R., Jiang Y.M. Prooxidant activities of quercetin, p-courmaric acid and their derivatives analysed by quantitative structure-activity relationship. Food Chem. 2012, 131:508-512.
193. Yang C., Li F., Zhang X., Wang L., Zhou Z., Wang M. Phenolic antioxidants from Rosa soulieana flowers. Nat. Prod. Res. 2013, 27:2055-2058.
194. Yokohira M., Yamakawa K., Saoo K., Matsuda Y., Hosokawa K., Hashimoto N., Kuno T., Imaida K. 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. 2008, 73:C561-C568.
195. Zhou C., Liu Y., Su D., Gao G., Zhou X., Sun L., Ba X., Chen X., Bi K. A sensitive LC-MS-MS method for simultaneous quantification of two structural isomers, hyperoside and isoquercitrin: application to pharmacokinetic studies. Chromatographia 2011, 73:353-359.
196. Zuo Z., Zhang L., Zhou L.M., Chang Q., Chow M. Intestinal absorption of hawthorn flavonoids - in vitro, in situ and in vivo correlations. Life Sci. 2006, 79:2455-2462.