Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells

Experimental Biology and Medicine

Volumn 240, Issue 11, 2015, Pages 1452-1464

  Sudan, Sudhanshu ^a   Rupasinghe, H P Vasantha ^a,b  

^a DALHOUSIE UNIVERSITY   (Canada)

^b DALHOUSIE UNIVERSITY   (Canada)

Author keywords

acylation; apoptosis; cancer; caspase 3; cell cycle; chemotherapy; hepatocellular carcinoma; HepG2 cells; Quercetin 3 O glucoside; topoisomerase II

Indexed keywords

CASPASE 3; CISPLATIN; DNA TOPOISOMERASE (ATP HYDROLYSING); DOCOSAHEXAENOIC ACID; ICOSAPENTAENOIC ACID; ISOQUERCITRIN; LINOLEIC ACID; LINOLENIC ACID; OLEIC ACID; OLEIC ACID ETHYL ESTER; QUERCETIN; SORAFENIB; STERIC ACID; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CARBANILAMIDE DERIVATIVE; ESTER; FATTY ACID; FLAVONOID; NICOTINAMIDE; QUERCETIN 3'-O-GLUCOSIDE;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER THERAPY; CELL CYCLE ARREST; CELL CYCLE S PHASE; CELL DEATH; CELL PROLIFERATION; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DNA FRAGMENTATION; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; LIVER CELL CARCINOMA; SIGNAL TRANSDUCTION; ANALOGS AND DERIVATIVES; CELL CYCLE; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; HEPG2 CELL LINE; LIVER TUMOR; METABOLISM; PATHOLOGY;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CARCINOMA, HEPATOCELLULAR; CASPASE 3; CELL CYCLE; CELL PROLIFERATION; CISPLATIN; DNA FRAGMENTATION; DNA TOPOISOMERASES, TYPE II; DRUG SCREENING ASSAYS, ANTITUMOR; ESTERS; FATTY ACIDS; FLAVONOIDS; HEP G2 CELLS; HUMANS; LIVER NEOPLASMS; MICROSCOPY, FLUORESCENCE; NIACINAMIDE; PHENYLUREA COMPOUNDS; QUERCETIN;

EID: 84931098268     PISSN: 15353702     EISSN: 15353699     Source Type: Journal    
DOI: 10.1177/1535370215570828     Document Type: Article

References (37)

1. H.P.V.RupasingheS.NairR.RobinsonChemopreventive properties of fruit phenolics and their possible mode of actions. In: Atta-Ur-Rahman (ed.). Studies in natural products chemistry2014; Vol 42.Amsterdam: Elsevier Science Publishers, pp. 229–66.
2. I.C.ArtsP.C.HollmanH.B.De MesquitaE.J.FeskensD.Kromhout. Dietary catechins and epithelial cancer incidence: the Zutphen elderly study. Int J Cancer2001; 92: 298–302.
3. P.KnektJ.KumpulainenR.JärvinenH.RissanenM.HeliövaaraA.ReunanenT.HakulinenA.Aromaa. Flavonoid intake and risk of chronic diseases. Am J Clin Nutr2002; 76: 560–8.
4. L.Le MarchandS.P.MurphyJ.H.HankinL.R.WilkensL.N.Kolonel. Intake of flavonoids and lung cancer. J Natl Cancer Inst2000; 92: 154–60.
5. S.C.ShenY.C.ChenF.L.HsuW.R.Lee. Differential apoptosis-inducing effect of quercetin and its glycosides in human promyeloleukemic HL-60 cells by alternative activation of the caspase 3 cascade. J Cell Biochem2003; 89: 1044–55.
6. R.SinghalY.A.YehN.PrajaE.OlahG.W.SlegeG.Weber. Quercetin down-regulates signal transduction in human breast carcinoma cells. Biochem Biophys Res Commun1995; 208: 425–31.
7. T.NguyenE.TranT.NguyenP.T.DoT.H.HuynhH.Huynh. The role of activated MEK-ERK pathway in quercetin-induced growth inhibition and apoptosis in A549 lung cancer cells. Carcinogenesis2004; 25: 647–59.
8. G.AgulloL.Gamet-PayrastreS.ManentiC.VialaC.RemesyH.ChapB.Payrastre. Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: a comparison with tyrosine kinase and protein kinase C inhibition. Biochem Pharmacol1997; 53: 1649–57.
9. A.B.Granado-SerranoM.A.MartínL.BravoL.GoyaS.Ramos. Quercetin induces apoptosis via caspase activation, regulation of Bcl-2, and inhibition of PI-3-kinase/Akt and ERK pathways in a human hepatoma cell line (HepG2). J Nutr2006; 136: 2715–21.
10. L.LanoueK.GreenC.Kwik-UribeC.L.Keen. Dietary factors and the risk for acute infant leukemia: evaluating the effects of cocoa-derived flavanols on DNA topoisomerase activity. Exp Biol Med2010; 235: 77–89.
11. S.M.RazaviS.ZahriG.ZarriniH.NazemiyehS.Mohammadi. Biological activity of quercetin-3-O-glucoside, a known plant flavonoid. Bioorg Khim2009; 35: 414–6.
12. S.SudanH.P.V.Rupasinghe. Quercetin-3-O-glucoside induces human DNA topoisomerase II inhibition, cell cycle arrest and apoptosis in hepatocellular carcinoma cells. Anti-cancer Res2014; 34: 1691–9.
13. S.PassamontiM.TerdoslavichR.FrancaA.VanzoF.TramerE.BraidotE.PetrussaA.Vianello. Bioavailability of flavonoids: a review of their membrane transport and the function of bilitranslocase in animal and plant organisms. Curr Drug Metabol2009; 10: 369–94.
14. Y.T.LinS.L.HsiuY.C.HouH.Y.ChenC.P.Lee. Degradation of flavonoid aglycones by rabbit, rat and human fecal flora. Biol Pharm Bull2003; 26: 747–51.
15. J.SalemI.ChevalotC.H.SchiavoC.ParisM.FickC.Humeau. Biological activities of flavonoids from Nitraria retusa (Forssk.) Asch. and their acylated derivatives. Food Chem2011; 124: 486–94.
16. T.Mainou-FowlerS.J.ProctorA.M.Dickinson. Gamma-linolenic acid induces apoptosis in B-chronic lymphocytic leukaemia cells in vitro. Leuk Lymph2001; 40: 393–403.
17. W.E.Hardman. Omega-3 fatty acids to augment cancer therapy. J Nutr2002; 132: 3508–12.
18. ZiaullahK.S.BhullarS.N.WarnakulasuriyaH.P.V.Rupasinghe. Biocatalytic synthesis structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin. Bioorg Med Chem2013; 21: 684–92.
19. W.TalibA.Mahasneh. Antiproliferative activity of plant extracts used against cancer in traditional medicine. Sci Pharm2010; 78: 33–45.
20. B.ShanM.WangR.Li. Quercetin inhibit human SW480 colon cancer growth in association with inhibition of cyclin D1 and survivin expression through Wnt/β-catenin signaling pathway. Cancer Invest2009; 27: 604–12.
21. N.PatraU.DeJ.A.KangJ.M.KimM.Y.AhnJ.Lee. A novel epoxypropoxy flavonoid derivative and topoisomerase II inhibitor, MHY336, induces apoptosis in prostate cancer cells. Eur J Pharmacol2011; 658: 98–107.
22. A.A.Van de LoosdrechtR.H.J.BeelenG.J.OssenkoppeleM.G.BroekhovenM.M.Langenhuijsen. A tetrazolium-based colorimetric MTT assay to quantitate human monocyte mediated cytotoxicity against leukemic cells from cell lines and patients with acute myeloid leukemia. J Immunol Methods1994; 174: 311–20.
23. Lisa KM. Handbook of assay development in drug discovery. 2004: Series 5. 385–406
24. T.L.RissR.A.Moravec. Use of multiple assay endpoints to investigate the effects of incubation time, dose of toxin, and plating density in cell-based cytotoxicity assays. Assay Drug Dev Technol2004; 2: 51–62.
25. S.J.RiedlY.Shi. Molecular mechanisms of caspase regulation during apoptosis. Nat Rev Mol Cell Biol2004; 5: 897–907.
26. L.GibelliniM.PintiM.Nasi. Quercetin and cancer chemoprevention. Evid Based Complement Alternat Med2011, pp. 1–15.
27. S.KitagawaY.TanakaM.TanakaK.EndoA.Yoshii. Enhanced skin delivery of quercetin by microemulsion. J Pharm2009; 61: 855–60.
28. L.E.BrökerF.A.E.KruytG.Giaccone. Cell death independent of caspases: a review. Clin Cancer Res2005; 11: 3155–62.
29. I.K.H.PoonM.D.HulettC.R.Parish. Molecular mechanisms of late apoptotic/necrotic cell clearance. Cell Death Differ2010; 17: 381–97.
30. A.SarasteK.Pulkki. Morphologic and biochemical hallmarks of apoptosis. Cardiovasc Res2000; 45: 528–37.
31. E.CheongK.IvoryJ.DolemanM.L.ParkerA.Rhodes. Synthetic and naturally occurring COX-2 inhibitors suppress proliferation in a human oesophageal adenocarcinoma cell line (OE33) by inducing apoptosis and cell cycle arrest. Carcinogenesis2004; 25: 1945–52.
32. N.HosokawaY.HosokawaT.SakaiM.YoshidaN.Marui. Inhibitory effect of quercetin on the synthesis of a possibly cell-cycle-related 17-kDa protein, in human colon cancer cells. Int J Cancer1990; 45: 1119–24.
33. J.-A.ChoiJ.Y.KimJ.Y.LeeC.M.KangH.J.Kwon. Induction of cell cycle arrest and apoptosis in human breast cancer cells by quercetin. Int J Oncol2001; 19: 837–44.
34. A.CossM.TosettoE.J.FoxB.Sapetto-RebowS.GormanB.N.KennedyA.T.LloydJ.M.HylandD.P.O'DonoghueK.SheahanD.T.LeahyH.E.MulcahyJ.N.O'Sullivan. Increased topoisomerase IIα expression in colorectal cancer is associated with advanced disease and chemotherapeutic resistance via inhibition of apoptosis. Cancer Lett2009; 276: 228–38.
35. A.El-AwadyM.M.AliE.M.SalehF.M.Ghaleb. Apoptosis is the most efficient death-pathway in tumor cells after topoisomerase II inhibition. Saudi Med J2008; 29: 558–64.
36. H.NiidaM.Nakanishi. DNA damage checkpoints in mammals. Mutagenesis2006; 21: 3–9.
37. S.V.G.NairZiaullahH.P.V.Rupasinghe. Fatty acid esters of phloridzin induce apoptosis of human liver cancer cells through altered gene expression. PLoS ONE2014; 9: e107149.