Review of anticancer mechanisms of isoquercitin

World Journal of Clinical Oncology

Volumn 7, Issue 2, 2016, Pages 189-199

  Di Camillo Orfali, Guilherme ^a   Duarte, Ana Carolina ^a   Bonadio, Vivien ^a   Martinez, Natalia Peres ^a   De Araújo, Maria Elisa Melo Branco ^a   Priviero, Fernanda Bruschi Marinho ^a   Carvalho, Patricia Oliveira ^a   Priolli, Denise Gonçalves ^a  

^a Universidade Sao Francisco Centro de Ciencias Biologicas e da Saude   (Brazil)

Author keywords

Antioxidants; Antitumor; Cancer; Drug screening assays; Flavonoids; Flavonols; Neoplasms

Indexed keywords

EID: 84963804592     PISSN: None     EISSN: 22184333     Source Type: Journal    
DOI: 10.5306/wjco.v7.i2.189     Document Type: Review

References (94)

1. Dhiman A, Nanda A, Ahmad S. A quest for staunch effects of flavonoids: Utopian protection against hepatic ailments. Arab J Chem 2012; In press [DOI:10.1016/j.arabjc.2012.05.001].
2. Appleton J. Evaluating the Bioavailability of Isoquercetin. Nat Med J 2010; 2: 1-6.
3. Masuda T, Iritani K, Yonemori S, Oyama Y, Takeda Y. Isolation and antioxidant activity of galloyl flavonol glycosides from the seashore plant, Pemphis acidula. Biosci Biotechnol Biochem 2001; 65: 1302-1309 [PMID: 11471728 DOI:10.1007/s11746-999-0060-0].
4. Murota K, Shimizu S, Chujo H, Moon JH, Terao J. Efficiency of absorption and metabolic conversion of quercetin and its glucosides in human intestinal cell line Caco-2. Arch Biochem Biophys 2000; 384: 391-397 [PMID: 11368329 DOI: 10.1006/abbi.2000.2123].
5. Nishimura J, Saegusa Y, Dewa Y, Jin M, Kawai M, Kemmochi S, Harada T, Hayashi SM, 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 [PMID: 20033131 DOI:10.1007/s00204-009-0497-9].
6. 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 [PMID: 17484383 DOI:10.3177/jnsv.53.68].
7. de Araújo ME, Moreira Franco YE, Alberto TG, Sobreiro MA, Conrado MA, Priolli DG, Frankland Sawaya AC, Ruiz AL, de Carvalho JE, de Oliveira Carvalho P. Enzymatic de-glycosylation of rutin improves its antioxidant and antiproliferative activities. Food Chem 2013; 141: 266-273 [PMID: 23768357 DOI:10.1016/j.foodchem.2013.02.127].
8. Day AJ, Gee JM, DuPont MS, Johnson IT, 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 [PMID: 12663055 DOI:10.1016/S0006-2952(03)00039-X].
9. Boyer J, Brown D, Liu RH. In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer. Nutr J 2005; 4: 1 [PMID: 15644141 DOI: 10.1186/1475-2891-4-1].
10. Sesink AL, Arts IC, Faassen-Peters M, Hollman PC. Intestinal uptake of quercetin-3-glucoside in rats involves hydrolysis by lactase phlorizin hydrolase. J Nutr 2003; 133: 773-776 [PMID: 12612151].
11. Gee JM, DuPont MS, Day AJ, Plumb GW, Williamson G, Johnson IT. Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. J Nutr 2000; 130: 2765-2771 [PMID: 11053519].
12. Lesser S, Cermak R, Wolffram S. Bioavailability of quercetin in pigs is influenced by the dietary fat content. J Nutr 2004; 134: 1508-1511 [PMID: 15173420].
13. Cermak R, Landgraf S, Wolffram S. Quercetin glucosides inhibit glucose uptake into brush-border-membrane vesicles of porcine jejunum. Br J Nutr 2004; 91: 849-855 [PMID: 15182388 DOI:10.1079/BJN20041128].
14. Sesink AL, O'Leary KA, Hollman PC. 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 [PMID: 11435510].
15. Olthof MR, Hollman PC, Vree TB, Katan MB. Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans. J Nutr 2000; 130: 1200-1203 [PMID: 10801919].
16. Reinboth M, Wolffram S, Abraham G, Ungemach FR, Cermak R. Oral bioavailability of quercetin from different quercetin glycosides in dogs. Br J Nutr 2010; 104: 198-203 [PMID: 20230651 DOI:10.1017/S000711451000053X].
17. Chang Q, Zuo Z, Chow MS, Ho WK. Difference in absorption of the two structurally similar flavonoid glycosides, hyperoside and isoquercitrin, in rats. Eur J Pharm Biopharm 2005; 59: 549-555 [PMID: 15760736 DOI:10.1016/j.ejpb.2004.10.004].
18. Lesser S, Cermak R, Wolffram S. The fatty acid pattern of dietary fat influences the oral bioavailability of the flavonol quercetin in pigs. Br J Nutr 2006; 96: 1047-1052 [PMID: 17181879 DOI:10.1017/BJN20061953].
19. Lan K, Jiang X, He J. Quantitative determination of isorhamnetin, quercetin and kaempferol in rat plasma by liquid chromatography with electrospray ionization tandem mass spectrometry and its application to the pharmacokinetic study of isorhamnetin. Rapid Commun Mass Spectrom 2007; 21: 112-120 [PMID: 17154349 DOI:10.1002/rcm.2814].
20. Krogholm KS, Bredsdorff L, Knuthsen P, Haraldsdóttir J, Rasmussen SE. Relative bioavailability of the flavonoids quercetin, hesperetin and naringenin given simultaneously through diet. Eur J Clin Nutr 2010; 64: 432-435 [PMID: 20125185 DOI:10.1038/ejcn.2010.6].
21. Berger LM, Wein S, Blank R, Metges CC, Wolffram S. Bioavailability of the flavonol quercetin in cows after intraruminal application of quercetin aglycone and rutin. J Dairy Sci 2012; 95: 5047-5055 [PMID: 22916908 DOI:10.3168/jds.2012-5439].
22. Gohlke A, Ingelmann CJ, Nürnberg G, Starke A, Wolffram S, Metges CC. Bioavailability of quercetin from its aglycone and its glucorhamnoside rutin in lactating dairy cows after intraduodenal administration. J Dairy Sci 2013; 96: 2303-2313 [PMID: 23403185 DOI:10.3168/jds.2012-6234].
23. 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 [PMID: 12949368].
24. Wiczkowski W, Romaszko J, Bucinski A, Szawara-Nowak D, Honke J, Zielinski H, Piskula MK. Quercetin from shallots (Allium cepa L. var. aggregatum) is more bioavailable than its glucosides. J Nutr 2008; 138: 885-888 [PMID: 18424596].
25. Lee J, Mitchell AE. Pharmacokinetics of quercetin absorption from apples and onions in healthy humans. J Agric Food Chem 2012; 60: 3874-3881 [PMID: 22439822 DOI:10.1021/jf3001857].
26. Liang T, Yue W, Li Q. Comparison of the phenolic content and antioxidant activities of Apocynum venetum L. (Luo-Bu-Ma) and two of its alternative species. Int J Mol Sci 2010; 11: 4452-4464 [PMID: 21151449 DOI:10.3390/ijms11114452].
27. Heim KE, Tagliaferro AR, Bobilya DJ. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 2002; 13: 572-584 [PMID: 12550068 DOI:10.1016/S0955-2863(02)00208-5].
28. Vellosa JCR, Regasini LO, Khalil NM, Bolzani VS, Khalil OAK, Manente FA, Netto HP, Oliveira OMMF. Antioxidant and cytotoxic studies for kaempferol, quercetin and isoquercitrin. Eclet Quim 2001; 36: 7-20 [DOI:10.1590/S0100-46702011000200001].
29. Boligon AA, Sagrillo MR, Machado LF, de Souza Filho O, Machado MM, da Cruz IB, Athayde ML. 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 [PMID: 22628047 DOI:10.3390/molecules17055757].
30. Razavi SM, Zahri S, Zarrini G, Nazemiyeh H, Mohammadi S. Biological activity of quercetin-3-O-glucoside, a known plant flavonoid. Bioorg Khim 2009; 35: 414-416 [PMID: 19621057 DOI:10.1134/S1068162009030133].
31. Ioku K, Tsushida T, Takei Y, Nakatani N, Terao J. Antioxidative activity of quercetin and quercetin monoglucosides in solution and phospholipid bilayers. Biochim Biophys Acta 1995; 1234: 99-104 [PMID: 7880864 DOI:10.1016/0005-2736(94)00262-N].
32. Noroozi M, Angerson WJ, Lean ME. Effects of flavonoids and vitamin C on oxidative DNA damage to human lymphocytes. Am J Clin Nutr 1998; 67: 1210-1218 [PMID: 9625095].
33. Williamson G, Plumb GW, Uda Y, Price KR, Rhodes MJ. Dietary quercetin glycosides: Antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in Hepalclc7 cells. Carcinogenesis 1996; 17: 2385-2387 [PMID: 8968052 DOI:10.1093/carcin/17.11.2385].
34. Yokozawa T, Dong E, Kawai Y, Gemba M, Shimizu M. Protective effects of some flavonoids on the renal cellular membrane. Exp Toxicol Pathol 1999; 51: 9-14 [PMID: 10048707 DOI:10.1016/S0940-2993(99)80050-5].
35. Begum AN, Terao J. Protective effect of quercetin against cigarette tar extract-induced impairment of erythrocyte deformability. J Nutr Biochem 2002; 13: 265-272 [PMID: 12015156 DOI:10.1016/S0955-2863(01)00219-4].
36. Kamada C, da Silva EL, Ohnishi-Kameyama M, Moon JH, Terao J. Attenuation of lipid peroxidation and hyperlipidemia by quercetin glucoside in the aorta of high cholesterol-fed rabbit. Free Radic Res 2005; 39: 185-194 [PMID: 15763966 DOI:10.1080/10715760400019638].
37. Dufour C, Loonis M. Flavonoids and their oxidation products protect efficiently albumin-bound linoleic acid in a model of plasma oxidation. Biochim Biophys Acta 2007; 1770: 958-965 [PMID: 17428609 DOI:10.1016/j.bbagen.2007.02.005].
38. Soundararajan R, Wishart AD, Rupasinghe HP, Arcellana-Panlilio M, Nelson CM, Mayne M, Robertson GS. 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 [PMID: 18032389 DOI:10.1074/jbc.M703583200].
39. Jung SH, Kim BJ, Lee EH, Osborne NN. 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 [PMID: 20708054 DOI:10.1016/j.neuint.2010.08.005].
40. Li R, Yuan C, Dong C, Shuang S, Choi MM. In vivo antioxidative effect of isoquercitrin on cadmium-induced oxidative damage to mouse liver and kidney. Naunyn Schmiedebergs Arch Pharmacol 2011; 383: 437-445 [PMID: 21336539 DOI:10.1007/s00210-011-0613-2].
41. Kim BH, Choi JS, Yi EH, Lee JK, Won C, Ye SK, Kim MH. Relative antioxidant activities of quercetin and its structurally related substances and their effects on NF-κB/CRE/AP-1 signaling in murine macrophages. Mol Cells 2013; 35: 410-420 [PMID: 23649461 DOI:10.1007/s10059-013-0031-z].
42. Hassan W, Rongyin G, Daoud A, Ding L, Wang L, Liu J, Shang J. Reduced oxidative stress contributes to the lipid lowering effects of isoquercitrin in free fatty acids induced hepatocytes. Oxid Med Cell Longev 2014; 2014: 313602 [PMID: 25404990 DOI:10.1155/2014/313602].
43. Haas MJ, Onstead-Haas LM, Szafran-Swietlik A, Kojanian H, Davis T, Armstrong P, Wong NC, Mooradian AD. Induction of hepatic apolipoprotein A-I gene expression by the isoflavones quercetin and isoquercetrin. Life Sci 2014; 110: 8-14 [PMID: 24963805 DOI:10.1016/j.lfs.2014.06.014].
44. Chen P, Wu D, Pan Y. Separation and purification of antioxidants from Ampelopsis heterophylla by counter-current chromatography. J Sep Sci 2013; 36: 3660-3666 [PMID: 24123927 DOI:10.1002/jssc.201300917].
45. Maleš Z, Sarić D, Bojić M. Quantitative Determination of Flavonoids and Chlorogenic Acid in the Leaves of Arbutus unedo L. Using Thin Layer Chromatography. J Anal Methods Chem 2013; 2013: 385473 [PMID: 23984189 DOI:10.1155/2013/385473].
46. Kraujalis P, Venskutonis PR, 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 [PMID: 23912804 DOI:10.1007/s11130-013-0375-8].
47. 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 [PMID: 23805936 DOI: 10.1080/14786419.2013.811660].
48. Sukito A, Tachibana S. Isolation of hyperoside and isoquercitrin from Camellia sasanqua as antioxidant agents. Pak J Biol Sci 2014; 17: 999-1006 [PMID: 26031018 DOI:10.3923/pjbs.2014.999.1006].
49. Kim DS, Kang YM, Jin WY, Sung YY, Choi G, Kim HK. Antioxidant activities and polyphenol content of Morus alba leaf extracts collected from varying regions. Biomed Rep 2014; 2: 675-680 [PMID: 25054010 DOI:10.3892/br.2014.294].
50. Zhang TT, Lu CL, Jiang JG. Bioactivity evaluation of ingredients identified from the fruits of Amomum tsaoko Crevost et Lemaire, a Chinese spice. Food Funct 2014; 5: 1747-1754 [PMID: 24915829 DOI:10.1039/C4FO00169A].
51. Vlase L, Benedec D, Hanganu D, Damian G, Csillag I, Sevastre B, Mot AC, Silaghi-Dumitrescu R, Tilea I. Evaluation of antioxidant and antimicrobial activities and phenolic profile for Hyssopus officinalis, Ocimum basilicum and Teucrium chamaedrys. Molecules 2014; 19: 5490-5507 [PMID: 24786688 DOI:10.3390/molecules19055490].
52. Wang J, Cao X, Jiang H, Qi Y, Chin KL, Yue Y. Antioxidant activity of leaf extracts from different Hibiscus sabdariffa accessions and simultaneous determination five major antioxidant compounds by LC-Q-TOF-MS. Molecules 2014; 19: 21226-21238 [PMID: 25525823 DOI: 10.3390/molecules191221226].
53. Liaudanskas M, Viškelis P, Raudonis R, Kviklys D, Uselis N, Janulis V. Phenolic composition and antioxidant activity of Malus domestica leaves. Scientifi World Journal 2014; 2014: 306217 [PMID: 25302319 DOI:10.1155/2014/306217].
54. Orzel J, Daszykowski M, Kazura M, de Beer D, Joubert E, Schulze AE, Beelders T, de Villiers A, Malherbe CJ, Walczak B. Modeling of the total antioxidant capacity of rooibos (Aspalathus linearis) tea infusions from chromatographic fingerprints and identification of potential antioxidant markers. J Chromatogr A 2014; 1366: 101-109 [PMID: 25283576 DOI:10.1016/j.chroma.2014.09.030].
55. Mocan A, Crian G, Vlase L, Crian O, Vodnar DC, Raita O, Gheldiu AM, Toiu A, Oprean R, Tilea I. Comparative studies on polyphenolic composition, antioxidant and antimicrobial activities of Schisandra chinensis leaves and fruits. Molecules 2014; 19: 15162-15179 [PMID: 25247685 DOI: 10.3390/molecules190915162].
56. Cárdenas-Rodríguez N, González-Trujano ME, Aguirre-Hernández E, Ruíz-García M, Sampieri A, Coballase-Urrutia E, Carmona-Aparicio L. Anticonvulsant and antioxidant effects of Tilia americana var. mexicana and flavonoids constituents in the pentylenetetrazole-induced seizures. Oxid Med Cell Longev 2014; 2014: 329172 [PMID: 25197430 DOI:10.1155/2014/329172].
57. Taiwo BJ, Igbeneghu OA. Antioxidant and antibacterial activities of flavonoid glycosides from Ficus exasperata Vahl-Holl (moraceae) leaves. Afr J Tradit Complement Altern Med 2014; 11: 97-101 [PMID: 25371569 DOI:10.4314/ajtcam.v11i3.14].
58. Brito A, Areche C, Sepúlveda B, Kennelly EJ, Simirgiotis MJ. Anthocyanin characterization, total phenolic quantification and antioxidant features of some Chilean edible berry extracts. Molecules 2014; 19: 10936-10955 [PMID: 25072199 DOI:10.3390/molecules190810936].
59. Liu Y, Ma SS, Ibrahim SA, Li EH, Yang H, Huang W. Identification and antioxidant properties of polyphenols in lotus seed epicarp at different ripening stages. Food Chem 2015; 185: 159-164 [PMID: 25952854 DOI:10.1016/j.foodchem.2015.03.117].
60. Marksa M, Radušiene J, Jakštas V, Ivanauskas L, Marksiene R. Development of an HPLC post-column antioxidant assay for Solidago canadensis radical scavengers. Nat Prod Res 2016; 30: 536-543 [PMID: 25835071 DOI:10.1080/14786419.2015.1027703].
61. Andriamadio JH, Rasoanaivo LH, Benedec D, Vlase L, Gheldiu AM, Duma M, Toiu A, Raharisololalao A, Oniga I. HPLC/MS analysis of polyphenols, antioxidant and antimicrobial activities of Artabotrys hildebrandtii O. Hffm. extracts. Nat Prod Res 2015; 29: 2188-2196 [PMID: 25679267 DOI:10.1080/14786419.2015.1007458].
62. Ramirez JE, Zambrano R, Sepúlveda B, Kennelly EJ, Simirgiotis MJ. Anthocyanins and antioxidant capacities of six Chilean berries by HPLC-HR-ESI-ToF-MS. Food Chem 2015; 176: 106-114 [PMID: 25624212 DOI:10.1016/j.foodchem.2014.12.039].
63. Zorzetto C, Sánchez-Mateo CC, Rabanal RM, Lupidi G, Petrelli D, Vitali LA, Bramucci M, Quassinti L, Caprioli G, Papa F, Ricciutelli M, Sagratini G, Vittori S, Maggi F. Phytochemical analysis and in vitro biological activity of three Hypericum species from the Canary Islands (Hypericum reflexum, Hypericum canariense and Hypericum grandifolium). Fitoterapia 2015; 100: 95-109 [PMID: 25464055 DOI:10.1016/j.fitote.2014.11.013].
64. Bhullar KS, Rupasinghe HP. Antioxidant and cytoprotective properties of partridgeberry polyphenols. Food Chem 2015; 168: 595-605 [PMID: 25172753 DOI:10.1016/j.foodchem.2014.07.103].
65. Park SH, Kim HJ, Yim SH, Kim AR, Tyagi N, Shen H, Kim KK, Shin BA, Jung DW, Williams DR. Delineation of the role of glycosylation in the cytotoxic properties of quercetin using novel assays in living vertebrates. J Nat Prod 2014; 77: 2389-2396 [PMID: 25397870 DOI:10.1021/np500231g].
66. Amado NG, Fonseca BF, Cerqueira DM, Neto VM, Abreu JG. Flavonoids: potential Wnt/beta-catenin signaling modulators in cancer. Life Sci 2011; 89: 545-554 [PMID: 21635906 DOI:10.1016/j.lfs.2011.05.003].
67. Martinez NP, Kanno DT, Pereira JA, Cardinalli IA, Priolli DG. Beta-catenin and E-cadherin tissue "content" as prognostic markers in left-side colorectal cancer. Cancer Biomark 2011; 8: 129-135 [PMID: 22012768 DOI:10.3233/DMA-2011-0843].
68. Topcu Z, Ozturk B, Kucukoglu O, Kilinc E. Flavonoids in Helichrysum pamphylicum inhibit mammalian type I DNA topoisomerase. Z Naturforsch C 2008; 63: 69-74 [PMID: 18386491].
69. Salim EI, 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 [PMID: 15500932 DOI:10.1016/j.fct.2004.07.010].
70. Boyle SP, Dobson VL, Duthie SJ, Kyle JA, Collins AR. Absorption and DNA protective effects of flavonoid glycosides from an onion meal. Eur J Nutr 2000; 39: 213-223 [PMID: 11131368 DOI: 10.1007/s003940070014].
71. You HJ, Ahn HJ, Ji GE. Transformation of rutin to antiproliferative quercetin-3-glucoside by Aspergillus niger. J Agric Food Chem 2010; 58: 10886-10892 [PMID: 20886886 DOI:10.1021/jf102871g].
72. Kong CS, Kim YA, Kim MM, Park JS, Kim JA, Kim SK, Lee BJ, Nam TJ, Seo Y. Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells. Toxicol In Vitro 2008; 22: 1742-1748 [PMID: 18715546 DOI:10.1016/j.tiv.2008.07.013].
73. Queires LC, Fauvel-Lafètve F, Terry S, De la Taille A, Kouyoumdjian JC, Chopin DK, Vacherot F, Rodrigues LE, Crépin M. Polyphenols purified from the Brazilian aroeira plant (Schinus terebinthifolius, Raddi) induce apoptotic and autophagic cell death of DU145 cells. Anticancer Res 2006; 26: 379-387 [PMID: 16475722].
74. Chen Q, Li P, Li P, Xu Y, Li Y, Tang B. Isoquercitrin inhibits the progression of pancreatic cancer in vivo and in vitro by regulating opioid receptors and the mitogen-activated protein kinase signalling pathway. Oncol Rep 2015; 33: 840-848 [PMID: 25434366 DOI:10.3892/or.2014.3626].
75. Matysik G, Wójciak-Kosior M, Paduch R. The influence of Calendulae officinalis flos extracts on cell cultures, and the chromatographic analysis of extracts. J Pharm Biomed Anal 2005; 38: 285-292 [PMID: 15925220 DOI:10.1016/j.jpba.2004.12.034].
76. Yang J, Liu RH. Synergistic effect of apple extracts and quercetin 3-beta-d-glucoside combination on antiproliferative activity in MCF-7 human breast cancer cells in vitro. J Agric Food Chem 2009; 57: 8581-8586 [PMID: 19694432 DOI:10.1021/jf8039796].
77. Amado NG, Cerqueira DM, Menezes FS, da Silva JF, Neto VM, Abreu JG. Isoquercitrin isolated from Hyptis fasciculata reduces glioblastoma cell proliferation and changes beta-catenin cellular localization. Anticancer Drugs 2009; 20: 543-552 [PMID: 19491660 DOI:10.1097/CAD.0b013e32832d1149].
78. Kizaibek M, Popescu R, Prinz S, Upur H, Singhuber J, Zehl M, Kopp B. Towards modernization of the formulation of the traditional uighur medicine herbal preparation abnormal savda munziq. Evid Based Complement Alternat Med 2012; 2012: 863101 [PMID: 21837249 DOI:10.1155/2012/863101].
79. Salucci M, Stivala LA, 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 [PMID: 12085217 DOI:10.1038/sj.bjc.6600295].
80. Kern M, Tjaden Z, Ngiewih Y, Puppel N, Will F, Dietrich H, Pahlke G, Marko D. Inhibitors of the epidermal growth factor receptor in apple juice extract. Mol Nutr Food Res 2005; 49: 317-328 [PMID: 15759309 DOI:10.1002/mnfr.200400086].
81. 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 [PMID: 16444288 DOI:10.1038/sj.bjp.0706662].
82. Amado NG, Predes D, Fonseca BF, Cerqueira DM, Reis AH, Dudenhoeffer AC, Borges HL, Mendes FA, Abreu JG. Isoquercitrin suppresses colon cancer cell growth in vitro by targeting the Wnt/β-catenin signaling pathway. J Biol Chem 2014; 289: 35456-35467 [PMID: 25359775 DOI:10.1074/jbc.M114.621599].
83. 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 [PMID: 18803703 DOI:10.1111/j.1750-3841.2008.00862.x].
84. Silva CG, Raulino RJ, Cerqueira DM, Mannarino SC, Pereira MD, Panek AD, Silva JF, Menezes FS, Eleutherio EC. In vitro and in vivo determination of antioxidant activity and mode of action of isoquercitrin and Hyptis fasciculata. Phytomedicine 2009; 16: 761-767 [PMID: 19200698 DOI:10.1016/j.phymed.2008.12.019].
85. Krížková 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 [PMID: 21217855 DOI:10.2478/v10102-009-0018-y].
86. Shimada Y, Dewa Y, Ichimura R, Suzuki T, Mizukami S, Hayashi SM, Shibutani M, Mitsumori K. Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone. Toxicology 2010; 268: 213-218 [PMID: 20045035 DOI:10.1016/j.tox.2009.12.019].
87. Kuwata K, Shibutani M, Hayashi H, Shimamoto K, Hayashi SM, Suzuki K, Mitsumori K. Concomitant apoptosis and regeneration of liver cells as a mechanism of liver-tumor promotion by β-naphthoflavone involving TNFα-signaling due to oxidative cellular stress in rats. Toxicology 2011; 283: 8-17 [PMID: 21295105 DOI:10.1016/j.tox.2011.01.020].
88. Morita R, Shimamoto K, Ishii Y, Kuwata K, Ogawa B, Imaoka M, Hayashi SM, Suzuki K, Shibutani M, Mitsumori K. Suppressive effect of enzymatically modified isoquercitrin on phenobarbitalinduced liver tumor promotion in rats. Arch Toxicol 2011; 85: 1475-1484 [PMID: 21445586 DOI:10.1007/s00204-011-0696-z].
89. Rowlands TM, Symonds JM, Farookhi R, Blaschuk OW. Cadherins: crucial regulators of structure and function in reproductive tissues. Rev Reprod 2000; 5: 53-61 [PMID: 10711736 DOI:10.1530/ror.0.0050053].
90. Fujii Y, Kimura M, Ishii Y, Yamamoto R, Morita R, Hayashi SM, 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 [PMID: 23318833 DOI:10.1016/j.tox.2013.01.002].
91. Kimura M, Fujii Y, Yamamoto R, Yafune A, Hayashi SM, Suzuki K, Shibutani M. Involvement of multiple cell cycle aberrations in early preneoplastic liver cell lesions by tumor promotion with thioacetamide in a two-stage rat hepatocarcinogenesis model. Exp Toxicol Pathol 2013; 65: 979-988 [PMID: 23474136 DOI:10.1016/j.etp.2013.01.012].
92. Huang G, Tang B, Tang K, Dong X, Deng J, Liao L, Liao Z, Yang H, He S. Isoquercitrin inhibits the progression of liver cancer in vivo and in vitro via the MAPK signalling pathway. Oncol Rep 2014; 31: 2377-2384 [PMID: 24676882 DOI:10.3892/or.2014.3099].
93. Hara S, Morita R, Ogawa T, Segawa R, Takimoto N, Suzuki K, Hamadate N, Hayashi SM, Odachi A, Ogiwara I, Shibusawa S, Yoshida T, Shibutani M. Tumor suppression effects of bilberry extracts and enzymatically modified isoquercitrin in early preneoplastic liver cell lesions induced by piperonyl butoxide promotion in a two-stage rat hepatocarcinogenesis model. Exp Toxicol Pathol 2014; 66: 225-234 [PMID: 24680176 DOI:10.1016/j.etp.2014.02.002].
94. Velho S, Pinto A, Licastro D, Oliveira MJ, Sousa F, Stupka E, Seruca R. Dissecting the signaling pathways associated with the oncogenic activity of MLK3 P252H mutation. BMC Cancer 2014; 14: 182 [PMID: 24628919 DOI:10.1186/1471-2407-14-182].