Synthesis and cardiovascular protective effects of quercetin 7-O-sialic acid

Journal of Cellular and Molecular Medicine

Volumn 21, Issue 1, 2017, Pages 107-120

  Tian, Hua ^a   Liu, Qingchao ^b   Qin, Shucun ^a   Zong, Chuanlong ^a   Zhang, Ying ^a   Yao, Shutong ^a   Yang, Nana ^a   Guan, Tao ^a   Guo, Shoudong ^a  

^a TAISHAN MEDICAL UNIVERSITY   (China)

^b NORTHWEST UNIVERSITY   (China)

Author keywords

anti inflammation; anti oxidation; cardiovascular disease; cholesterol efflux; quercetin; sialic acid

Indexed keywords

3,3',4',5 TETRA O ACETYL QUERCETIN 7 O (5 ACETAMIDO 4,7,8, 9 TETRA O ACETYL 3,5 DIDEOXY B D GLYCERO A D GALACTO 2 NONULOPYRANOSONATE); 4 (3,5 DIACETOXY 7 HYDROXY 4 OXO 4H CHROMEN 2 YL) 1,2 PHENYLENE DIACETATE; ABC TRANSPORTER A1; ABC TRANSPORTER G1; APOLIPOPROTEIN A1; HIGH DENSITY LIPOPROTEIN; INTERCELLULAR ADHESION MOLECULE 1; LIPOPROTEIN; LOW DENSITY LIPOPROTEIN; METHYL (5 ACETAMIDO 4,7,8,9 TETRA O ACETYL 2 CHLORO 3,5 DIDEOXY D GLYCERO D GALACTO 2 NONULOPYRANOSID) ONATE; MONOCYTE CHEMOTACTIC PROTEIN 1; N ACETYLNEURAMINIC ACID; PLANT MEDICINAL PRODUCT; QUERCETIN; QUERCETIN 7 O (5 ACETAMIDO 3,5 DIDEOXYB D GLYCERO A D GALACTO 2 NONULOPYRANOSONATE); QUERCETIN 7 O SIALIC ACID; REACTIVE OXYGEN METABOLITE; TUMOR NECROSIS FACTOR; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1; ABC TRANSPORTER; CARDIOTONIC AGENT; OXIDIZED LOW DENSITY LIPOPROTEIN;

ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BLOOD SAMPLING; CARBON NUCLEAR MAGNETIC RESONANCE; CELL VIABILITY; CHOLESTEROL TRANSPORT; CONTROLLED STUDY; CYTOTOXICITY; DESILYLATION; ENZYME LINKED IMMUNOSORBENT ASSAY; FLOW RATE; FLUORESCENCE MICROSCOPY; HEART PROTECTION; HUMAN; HUMAN CELL; IN SITU HYBRIDIZATION; IN VITRO STUDY; LIPID PEROXIDATION; LIQUID CHROMATOGRAPHY; MACROPHAGE; MASS SPECTROMETRY; MTT ASSAY; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTON NUCLEAR MAGNETIC RESONANCE; SECRETION (PROCESS); SYNTHESIS; UMBILICAL VEIN ENDOTHELIAL CELL; UPREGULATION; WESTERN BLOTTING; ANIMAL; ATHEROSCLEROSIS; CELL LINE; CHEMISTRY; DRUG EFFECTS; INFLAMMATION; METABOLISM; MOUSE;

ANIMALS; APOLIPOPROTEIN A-I; ATHEROSCLEROSIS; ATP-BINDING CASSETTE TRANSPORTERS; CARDIOTONIC AGENTS; CELL LINE; CHEMOKINE CCL2; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; INFLAMMATION; INTERCELLULAR ADHESION MOLECULE-1; LIPOPROTEINS, LDL; MACROPHAGES; MICE; N-ACETYLNEURAMINIC ACID; OXIDATIVE STRESS; QUERCETIN; REACTIVE OXYGEN SPECIES; TUMOR NECROSIS FACTOR-ALPHA; VASCULAR CELL ADHESION MOLECULE-1;

EID: 84997787310     PISSN: 15821838     EISSN: None     Source Type: Journal    
DOI: 10.1111/jcmm.12943     Document Type: Article

References (49)

1. Taggart M. Vascular function in health and disease review series. J Cell Mol Med. 2010; 14: 1017.
2. Seidelmann SB, Lighthouse JK, Greif DM. Development and pathologies of the arterial wall. Cell Mol Life Sci. 2014; 71: 1977–99.
3. Strilić B, Eglinger J, Krieg M, et al. Electrostatic cell-surface repulsion initiates lumen formation in developing blood vessels. Curr Biol. 2010; 20: 2003–9.
4. Keppler OT, Hinderlich S, Langner J, et al. UDP-GlcNAC 2-epimerase: a regulator of cell surface sialylation. Science. 1999; 284: 1372–6.
5. Gokmen SS, Kilicli G, Ozcelik F, et al. Association between serum total and lipid-bound sialic acid concentration and the severity of coronary atherosclerosis. J Lab Clin Med. 2002; 140: 110–8.
6. Gopaul KP, Crook MA. Sialic acid: a novel marker of cardiovascular disease? Clin Biochem. 2006; 39: 667–81.
7. Heistad DD. Oxidative stress and vascular disease: 2005 Duff lecture. Arterioscler Thromb Vasc Biol. 2006; 26: 689–95.
8. Goswami K, Koner BC. Level of sialic acid residues in platelet proteins in diabetes, aging, and Hodgkin's lymphoma: a potential role of free radicals in desialylation. Biochem Biophys Res Commun. 2002; 297: 502–5.
9. Tanaka K, Tokumaru S, Kojo S. Possible involvement of radical reactions in desialylation of LDL. FEBS Lett. 1997; 413: 202–4.
10. Tertov VV, Kaplun VV, Sobenin IA, et al. Low-density lipoprotein modification occurring in human plasma possible mechanism of in vivo lipoprotein desialylation as a primary step of atherogenic modification. Atherosclerosis. 1998; 138: 183–95.
11. Eguchi H, Ikeda Y, Ookawara T, et al. Modification of oligosaccharides by reactive oxygen species decreases sialyl Lewis x-mediated cell adhesion. Glycobiology. 2005; 15: 1094–101.
12. Weiss P, Ashwell G. The asialoglycoprotein receptor: properties and modulation by ligand. Prog Clin Biol Res. 1989; 300: 169–84.
13. Iijima R, Takahashi H, Namme R, et al. Novel biological function of sialic acid (N-Acetylneuraminic acid) as a hydrogen peroxide scavenger. FEBS Lett. 2004; 561: 163–6.
14. Ogasawara Y, Namai T, Yoshino F, et al. Sialic acid is an essential moiety of mucin as a hydroxyl radical scavenger. FEBS Lett. 2007; 581: 2473–7.
15. Serdar Z, Yesilbursa D, Dirican M, et al. Sialic acid and oxidizability of lipid and proteins and antioxidant status in patients with coronary artery disease. Cell Biochem Funct. 2007; 25: 655–64.
16. Malicdan MCV, Noguchi S, Hayashi YK, et al. Prophylactic treatment with sialic acid metabolites precludes the development of the myopathic phenotype in the DMRV-Hibm mouse model. Nat Med. 2009; 15: 390–696.
17. Nishino I, Noguchi S. Sialic acid supplementation therapy for distal myopathy with rimmed vacuoles. Brain Nerve. 2012; 64: 255–61.
18. Malicdan MCV, Noguchi S, Nishino I. Perspectives on distal myopathy with rimmed vacuoles or hereditary inclusion body myopathy: contributions from an animal model. Lack of sialic acid, a central determinant in sugar chains, causes myopathy? Acta Myol. 2007; 26: 171–5.
19. Yi L, Chen CY, Jin X, et al. Differential suppression of intracellular reactive oxygen species-mediated signaling pathway in vascular endothelial cells by several subclasses of flavonoids. Biochimie. 2012; 94: 2035–44.
20. Kleemann R, Verschuren L, Morrison M, et al. Anti-inflammatory, anti-proliferative and anti-atherosclerotic effects of quercetin in human in vitro and in vivo models. Atherosclerosis. 2011; 218: 44–52.
21. Lee SM, Moon J, Cho Y, et al. Quercetin up-regulates expressions of peroxisome proliferator-activated receptor γ, liver X receptor α, and ATP binding cassette transporter A1 genes and increases cholesterol efflux in human macrophage cell line. Nutr Res. 2013; 33: 136–43.
22. Varki A. Biological roles of oligosaccharides: all of the theories are correct. Glycobiology. 1993; 3: 97–130.
23. Aksenov DV, Medvedeva LA, Skalbe TA, et al. Deglycosylation of apo B-containing lipoproteins increase their ability to aggregate and to promote intracellular cholesterol accumulation in vitro. Arch Physiol Biochem. 2008; 114: 349–56.
24. Havel RJ, Eder HA, Bragdon JH. Distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum. J Clin Invest. 1955; 34: 1345–53.
25. Yao ST, Sang H, Song GH, et al. Quercetin protects macrophages from oxidized low-density lipoprotein-induced apoptosis by inhibiting the endoplasmic reticulum stress-C/EBP homologous protein pathway. Exp Bio Med. 2012; 237: 822–31.
26. Guo SD, Yu Y, Zhang N, et al. Higher level of plasma bioactive molecule sphingosine-1-phosphate in women in associated with estrogen. Biochim Biophys Acta. 2014; 1841: 836–46.
27. Panicker SR, Sreenivas P, Babu MS, et al. Quercetin attenuates monocyte chemoattractant protein-1 gene expression in glucose primed aortic endothelial cells through NF-κB and AP-1. Pharmacol Res. 2010; 62: 328–36.
28. Zhang Y, Yuan JB, Song JJ, et al. An efficient method for selectively imaging and quantifying in situ the expression of sialylated glycoproteins on living cells. Glycobiology. 2013; 23: 643–53.
29. Guo SD, Hui S, Yang NN, et al. Measurement of sialic acid from lipoproteins and human plasma by liquid chromatography-tandem mass spectrometry. Chin J Chromatogr. 2014; 32: 1197–200.
30. Low H, Hoang A, Sviridov D. Cholesterol efflux assay. J Vis Exp. 2012; 61: 1–5.
31. Muto E, Dell'Agli M, Sangiovanni E, et al. Olive oil phenolic extract regulates interleukin-8 expression by transcriptional and posttranscriptional mechanisms in Caco-2 cells. Mol Nutr Food Res. 2015; 59: 1217–21.
32. Chang YF, Chi CW, Wang JJ. Reactive oxygen species production is involved in quercetin-induced apoptosis in human hepatoma cells. Nutr Cancer. 2006; 55: 201–9.
33. Boesch-Saadatmandi C, Pospissil RT, Graeser AC, et al. Effect of quercetin on paraoxonase 2 levels in Raw 264.7 macrophages and in human monocytes-role of quercetin metabolism. Int J Mol Sci. 2009; 10: 4168–77.
34. Harrison D, Griendling KK, Landmesser U, et al. Role of oxidative stress in atherosclerosis. Am J Cardiol. 2003; 91: 7A–11A.
35. Pearson TA, Mensah GA, Wayne Alexander R, et al. Markers of inflammation and cardiovascular disease: application to clinical and public health practice: a statement for healthcare professionals from the centers for disease control and prevention and the American heart association. Circulation. 2003; 107: 499–511.
36. Finkel T. Signal transduction by reactive oxygen species. J Cell Biol. 2011; 194: 7–15.
37. Kim GH, Ryan JJ, Archer SL. Antioxidant & redox signaling. April. 2013; 18: 1920–36.
38. Madamanchi NR, Runge MS. Redox signaling in cardiovascular health and disease. Free Radic. Res. 2014; 48: 3–11.
39. Yang D, Liu X, Liu M, et al. Protective effects of quercetin and taraxasterol against H2O2-induced human umbilical vein endothelial cell injury in vitrol. Exp. Ther. Med. 2015; 10: 1253–60.
40. Noguchi S, Keira Y, Murayama K, et al. Reduction of UDP-N-acetylglucosamine 2-Epimerase/N-acetylmannosamine kinase activity and sialylation in distal myopathy with rimmed vacuoles. J Bio Chem. 2004; 279: 11402–7.
41. Bardor M, Nguyen DH, Diaz S, et al. Mechanism of uptake and incorporation of the non-human sialic acid N-glycolylneuraminic acid into human cells. J Bio Chem. 2005; 280: 4228–37.
42. Marmillot P, Rao MN, Liu QH, et al. Desialylation of human apolipoprotein E decreases its binding to human high-density lipoprotein and its ability to deliver esterified cholesterol to the liver. Metabolism. 1999; 48: 1184–92.
43. Khoo JC, Miller E, Mcloughlin P, et al. Enhanced macrophage uptake of low density lipoprotein after self-aggregation. Arteriosclerosis. 1988; 8: 348–58.
44. Iiyama K, Hajra L, Liyama M, et al. Patterns of vascular cell adhesion molecule 1 and intercellular adhesion molecule-1 expression in rabbit and mouse atherosclerotic lesions and at sites predisposed to lesion formation. Circ Res. 1999; 85: 199–207.
45. Van Leeuwen M, Gijbels MJ, Duijvestijn A, et al. Accumulation of myeloperoxidase-positive neutrophils in atheroscierotic lesions in LDLR-/- mice. Arterioscler Thromb Vasc Biol. 2008; 28: 84–9.
46. Goedeke L, Fernández-Hernando C. Regulation of cholesterol homeostasis. Cell Mol Life Sci. 2012; 69: 915–30.
47. Maxfield FR, Tabas I. Role of cholesterol and lipid organization in disease. Nature. 2005; 438: 612–21.
48. Chang YC, Lee TS, Chiang AN. Quercetin enhances ABCA1 expression and cholesterol efflux through a p38-dependent pathway in macrophages. J Lipid Res. 2012; 53: 1840–50.
49. Guo SD, Tian H, Dong RR, et al. Exogenous supplement of N-acetylneuraminic acid ameliorates atherosclerosis in apolipoprotein E-deficient mice. Atherosclerosis. 2016; 251: 183–91.