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Volumn 30, Issue 1, 2015, Pages 107-113

2-Chloro-1,4-naphthoquinone derivative of quercetin as an inhibitor of aldose reductase and anti-inflammatory agent

Author keywords

Diabetic complications; Flavonoids; Polyol pathway

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 3,7 DI HYDROXY 2 [4 (2 CHLORO 1,4 NAPHTHOQUINONE 3 YLOXY) 3 HYDROXYPHENYL] 5 HYDROXY CHROMEN 4 ONE; ALDEHYDE REDUCTASE; ANTIINFLAMMATORY AGENT; GLUCOSE; OXIDOREDUCTASE INHIBITOR; QUERCETIN; SORBITOL; UNCLASSIFIED DRUG; NAPHTHOQUINONE;

EID: 84921292434     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2014.892935     Document Type: Article
Times cited : (36)

References (41)
  • 1
    • 80054054044 scopus 로고    scopus 로고
    • Aldose reductase: New insights for an old enzyme
    • Ramana K-V. Aldose reductase: new insights for an old enzyme. Biomol Concepts 2011;2:103-14.
    • (2011) Biomol Concepts , vol.2 , pp. 103-114
    • Ramana, K.-V.1
  • 3
    • 0029148587 scopus 로고
    • New approaches for treatment in diabetes: Aldose reductase inhibitors
    • Hotta N. New approaches for treatment in diabetes: aldose reductase inhibitors. Biomed Pharmacother 1995;5:244-50.
    • (1995) Biomed Pharmacother , vol.5 , pp. 244-250
    • Hotta, N.1
  • 5
    • 0036113742 scopus 로고    scopus 로고
    • Recent advances in aldose reductase inhibitors: Potential agents for the treatment of diabetic complications
    • Miyamoto S. Recent advances in aldose reductase inhibitors: potential agents for the treatment of diabetic complications. Expert Opin Ther Patents 2002;12:621-31.
    • (2002) Expert Opin Ther Patents , vol.12 , pp. 621-631
    • Miyamoto, S.1
  • 6
    • 18844369302 scopus 로고    scopus 로고
    • Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options
    • Srivastava S-K, Ramana K-V, Bhatnagar A. Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options. Endocr Rev 2005;26:380-92.
    • (2005) Endocr Rev , vol.26 , pp. 380-392
    • Srivastava, S.-K.1    Ramana, K.-V.2    Bhatnagar, A.3
  • 7
    • 65649103414 scopus 로고    scopus 로고
    • Aldose reductase enzyme and its implication to major health problems of the 21(st) century
    • Alexiou P, Pegklidou K, Chatzopoulou M, et al. Aldose reductase enzyme and its implication to major health problems of the 21(st) century. Curr Med Chem 2009;16:734-52.
    • (2009) Curr Med Chem , vol.16 , pp. 734-752
    • Alexiou, P.1    Pegklidou, K.2    Chatzopoulou, M.3
  • 9
    • 43049176634 scopus 로고    scopus 로고
    • Health effects of quercetin: From antioxidant to nutraceutical
    • Boots A-W, Haenen GRMM, Bast A. Health effects of quercetin: from antioxidant to nutraceutical. Eur J Pharm 2008;585:325-37.
    • (2008) Eur J Pharm , vol.585 , pp. 325-337
    • Boots, A.-W.1    Grmm, H.2    Bast, A.3
  • 10
    • 80055003490 scopus 로고    scopus 로고
    • Eye lens in aging and diabetes: Effect of quercetin
    • Stefek M, Karasu C. Eye lens in aging and diabetes: effect of quercetin. Rejuvenation Res 2011;14:525-34.
    • (2011) Rejuvenation Res , vol.14 , pp. 525-534
    • Stefek, M.1    Karasu, C.2
  • 11
    • 3142621340 scopus 로고    scopus 로고
    • The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides
    • Arts IC, 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;91:841-7.
    • (2004) Br J Nutr , vol.91 , pp. 841-847
    • Arts, I.C.1    Sesink, A.-L.2    Faassen-Peters, M.3    Hollman, P.-C.4
  • 12
    • 78649631235 scopus 로고    scopus 로고
    • Bioavailability of dietary flavonoids and phenolic compounds
    • Crozier A, Del Rio D, Clifford M-N. Bioavailability of dietary flavonoids and phenolic compounds. Mol Aspects Med 2010;31:446-67.
    • (2010) Mol Aspects Med , vol.31 , pp. 446-467
    • Crozier, A.1    Del Rio, D.2    Clifford, M.-N.3
  • 13
    • 84866757704 scopus 로고    scopus 로고
    • Novel quercetin derivatives: Synthesis and screening for antioxidant activity and aldose reductase inhibition
    • Veverka M, Gallovic J, Svajdlenka E, et al. Novel quercetin derivatives: synthesis and screening for antioxidant activity and aldose reductase inhibition. Chem Papers 2013;67:76-83.
    • (2013) Chem Papers , vol.67 , pp. 76-83
    • Veverka, M.1    Gallovic, J.2    Svajdlenka, E.3
  • 14
    • 84892531685 scopus 로고    scopus 로고
    • Screening for antiradical efficiency of 21 semi-synthetic derivatives of quercetin in a DPPH assay
    • Milackova I, Kovacikova L, Veverka M, et al. Screening for antiradical efficiency of 21 semi-synthetic derivatives of quercetin in a DPPH assay. Interdiscip Toxicol 2013;6:13-17.
    • (2013) Interdiscip Toxicol , vol.6 , pp. 13-17
    • Milackova, I.1    Kovacikova, L.2    Veverka, M.3
  • 15
    • 0028303794 scopus 로고
    • Comparative toxicity of alkyl-1,4-naphthoquinones in rats: Relationship to free radical production in vitro
    • Munday R, Fowke E-A, Smith B-L, Munday C-M. Comparative toxicity of alkyl-1,4-naphthoquinones in rats: relationship to free radical production in vitro. Free Radic Biol Med 1994;16:725-31.
    • (1994) Free Radic Biol Med , vol.16 , pp. 725-731
    • Munday, R.1    Fowke, E.-A.2    Smith, B.-L.3    Munday, C.-M.4
  • 16
    • 34247503841 scopus 로고    scopus 로고
    • Structure-activity relationships in the haemolytic activity and nephrotoxicity of derivatives of 1,2- and 1,4-naphthoquinone
    • Munday R, Smith B-L, Munday C-M. Structure-activity relationships in the haemolytic activity and nephrotoxicity of derivatives of 1,2- and 1,4-naphthoquinone. J Appl Toxicol 2007;27:262-9.
    • (2007) J Appl Toxicol , vol.27 , pp. 262-269
    • Munday, R.1    Smith, B.-L.2    Munday, C.-M.3
  • 17
    • 0000930578 scopus 로고
    • Isolation and properties of lens aldose reductase
    • Hayman S, Kinoshita J. Isolation and properties of lens aldose reductase. J Biol Chem 1965;240:877-82.
    • (1965) J Biol Chem , vol.240 , pp. 877-882
    • Hayman, S.1    Kinoshita, J.2
  • 18
    • 43049159358 scopus 로고    scopus 로고
    • Carboxymethylated pyridoindole antioxidants as aldose reductase inhibitors: Synthesis, activity, partitioning, and molecular modelling
    • Stefek M, Snirc V, Djoubissie P-O, et al. Carboxymethylated pyridoindole antioxidants as aldose reductase inhibitors: synthesis, activity, partitioning, and molecular modelling. Bioorg Med Chem 2008;16:4908-20.
    • (2008) Bioorg Med Chem , vol.16 , pp. 4908-4920
    • Stefek, M.1    Snirc, V.2    Djoubissie, P.-O.3
  • 19
    • 0033519649 scopus 로고    scopus 로고
    • 1-Benzopyran-4-one antioxidants as aldose reductase inhibitors
    • Costantino L, Rastelli G, Gamberini M-C, et al. 1-Benzopyran-4-one antioxidants as aldose reductase inhibitors. J Med Chem 1999;42:1881-93.
    • (1999) J Med Chem , vol.42 , pp. 1881-1893
    • Costantino, L.1    Rastelli, G.2    Gamberini, M.-C.3
  • 20
    • 77349120507 scopus 로고    scopus 로고
    • Carboxymethylated tetrahydropyridoindoles as aldose reductase inhibitors: In vitro selectivity study in intact rat erythrocytes in relation to glycolytic pathway
    • Juskova M, Snirc V, Gajdosikova A, et al. Carboxymethylated tetrahydropyridoindoles as aldose reductase inhibitors: in vitro selectivity study in intact rat erythrocytes in relation to glycolytic pathway. Gen Physiol Biophys 2009;28:325-30.
    • (2009) Gen Physiol Biophys , vol.28 , pp. 325-330
    • Juskova, M.1    Snirc, V.2    Gajdosikova, A.3
  • 21
    • 12444318652 scopus 로고    scopus 로고
    • A highly selective, non-hydantoin, non-carboxylic acid inhibitor of aldose reductase with potent oral activity in diabetic rat models: 6-(5-chloro-3-methyl-benzofuran-2-sulfonyl)-2-H-pyridazin-3-one
    • Mylari B-L, Armento S-J, Beebe D-A, et al. A highly selective, non-hydantoin, non-carboxylic acid inhibitor of aldose reductase with potent oral activity in diabetic rat models: 6-(5-chloro-3-methyl-benzofuran-2-sulfonyl)-2-H-pyridazin-3-one. J Med Chem 2003;46:2283-6.
    • (2003) J Med Chem , vol.46 , pp. 2283-2286
    • Mylari, B.-L.1    Armento, S.-J.2    Beebe, D.-A.3
  • 22
    • 0026650922 scopus 로고
    • Acetic acid-induced colitis in the rat: A reproducible experimental model for acute ulcerative colitis
    • Fabia R, Willen R, Ar'Rajab A, et al. Acetic acid-induced colitis in the rat: a reproducible experimental model for acute ulcerative colitis. Eur Surg Res 1992;24:211-25.
    • (1992) Eur Surg Res , vol.24 , pp. 211-225
    • Fabia, R.1    Willen, R.2    Ar'Rajab, A.3
  • 23
    • 34147219227 scopus 로고    scopus 로고
    • Protective effect of melatonin in acetic acid induced colitis in rats
    • Nosalova V, Zeman M, Cerna S, et al. Protective effect of melatonin in acetic acid induced colitis in rats. J Pineal Res 2007;42:364-70.
    • (2007) J Pineal Res , vol.42 , pp. 364-370
    • Nosalova, V.1    Zeman, M.2    Cerna, S.3
  • 24
    • 0025145949 scopus 로고
    • Oxidative reactions of hemoglobin
    • Winterbourn C-C. Oxidative reactions of hemoglobin. Meth Enzymol 1990;186:265-72.
    • (1990) Meth Enzymol , vol.186 , pp. 265-272
    • Winterbourn, C.-C.1
  • 25
    • 33746563448 scopus 로고    scopus 로고
    • Advances in methods and algorithms in a modern quantum chemistry program package
    • Shao Y, Molnar L-F, Jung Y, et al. Advances in methods and algorithms in a modern quantum chemistry program package. Phys Chem Chem Phys 2006;8:3172-91.
    • (2006) Phys Chem Chem Phys , vol.8 , pp. 3172-3191
    • Shao, Y.1    Molnar, L.-F.2    Jung, Y.3
  • 26
    • 0037093644 scopus 로고    scopus 로고
    • Increasing the precision of comparative models with YASARA NOVA - A self-parameterizing force field
    • Krieger E, Koraimann G, Vriend G. Increasing the precision of comparative models with YASARA NOVA - a self-parameterizing force field. Proteins [Online] 2002;47:393-402.
    • (2002) Proteins [Online] , vol.47 , pp. 393-402
    • Krieger, E.1    Koraimann, G.2    Vriend, G.3
  • 27
    • 77952414610 scopus 로고    scopus 로고
    • Aldose reductase inhibitory compounds from Glycyrrhiza uralensis
    • Lee Y-S, Kim S-H, Jung S-H, et al. Aldose reductase inhibitory compounds from Glycyrrhiza uralensis. Biol Pharm Bull 2010;33:917-21.
    • (2010) Biol Pharm Bull , vol.33 , pp. 917-921
    • Lee, Y.-S.1    Kim, S.-H.2    Jung, S.-H.3
  • 28
    • 56149111156 scopus 로고    scopus 로고
    • Inhibitory effects of Nelumbo nucifera leaves on rat lens aldose reductase, advanced glycation endproducts formation, and oxidative stress
    • Jung H-A, Jung Y-J, Yoon N-Y, et al. Inhibitory effects of Nelumbo nucifera leaves on rat lens aldose reductase, advanced glycation endproducts formation, and oxidative stress. Food Chem Toxicol 2008;46:3818-26.
    • (2008) Food Chem Toxicol , vol.46 , pp. 3818-3826
    • Jung, H.-A.1    Jung, Y.-J.2    Yoon, N.-Y.3
  • 29
    • 49749122118 scopus 로고    scopus 로고
    • Inhibitory activities of prenylated flavonoids from Sophora flavescens against aldose reductase and generation of advanced glycation endproducts
    • Jung H-A, Yoon N-Y, Kang S-S, et al. Inhibitory activities of prenylated flavonoids from Sophora flavescens against aldose reductase and generation of advanced glycation endproducts. J Pharm Pharmacol 2008;60:1227-36.
    • (2008) J Pharm Pharmacol , vol.60 , pp. 1227-1236
    • Jung, H.-A.1    Yoon, N.-Y.2    Kang, S.-S.3
  • 30
    • 34447512444 scopus 로고    scopus 로고
    • Inhibitors of aldose reductase and advanced glycation end-products formation from the leaves of Stelechocarpus cauliflorus R.E. Fr
    • Wirasathien L, Pengsuparp T, Suttisri R, et al. Inhibitors of aldose reductase and advanced glycation end-products formation from the leaves of Stelechocarpus cauliflorus R.E. Fr. Phytomedicine 2007;14:546-50.
    • (2007) Phytomedicine , vol.14 , pp. 546-550
    • Wirasathien, L.1    Pengsuparp, T.2    Suttisri, R.3
  • 31
    • 0036594601 scopus 로고    scopus 로고
    • Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity
    • Matsuda H, Morikawa T, Toguchida I, Yoshikawa M. Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull (Tokyo) 2002;50:788-95.
    • (2002) Chem Pharm Bull (Tokyo) , vol.50 , pp. 788-795
    • Matsuda, H.1    Morikawa, T.2    Toguchida, I.3    Yoshikawa, M.4
  • 32
    • 0024558571 scopus 로고
    • N- and 2-substituted N-(phenylsulfonyl)glycines as inhibitors of rat lens aldose reductase
    • DeRuiter J, Borne R-F, Mayfield C-A. N- and 2-substituted N-(phenylsulfonyl)glycines as inhibitors of rat lens aldose reductase. J Med Chem 1989;32:145-51.
    • (1989) J Med Chem , vol.32 , pp. 145-151
    • DeRuiter, J.1    Borne, R.-F.2    Mayfield, C.-A.3
  • 33
    • 0025172227 scopus 로고
    • Inhibitory activity and mechanism of inhibition of the N-[[(4-benzoylamino)phenyl]sulfonyl]amino acid aldose reductase inhibitors
    • DeRuiter J, Mayfield C-A. Inhibitory activity and mechanism of inhibition of the N-[[(4-benzoylamino)phenyl]sulfonyl]amino acid aldose reductase inhibitors. Biochem Pharmacol 1990;40:2219-26.
    • (1990) Biochem Pharmacol , vol.40 , pp. 2219-2226
    • DeRuiter, J.1    Mayfield, C.-A.2
  • 34
    • 0242288800 scopus 로고    scopus 로고
    • A flavone from Manilkara indica as a specific inhibitor against aldose reductase in vitro
    • Haraguchi H, Hayashi R, Ishizu T, Yagi A. A flavone from Manilkara indica as a specific inhibitor against aldose reductase in vitro. Planta Med 2003;69:853-5.
    • (2003) Planta Med , vol.69 , pp. 853-855
    • Haraguchi, H.1    Hayashi, R.2    Ishizu, T.3    Yagi, A.4
  • 35
    • 0021276233 scopus 로고
    • Effects of a new aldose reductase inhibitor on various tissues in vitro
    • Terashima H, Hama K, Yamamoto R, et al. Effects of a new aldose reductase inhibitor on various tissues in vitro. J Pharmacol Exp Ther 1984;229:226-30.
    • (1984) J Pharmacol Exp Ther , vol.229 , pp. 226-230
    • Terashima, H.1    Hama, K.2    Yamamoto, R.3
  • 36
    • 10844222740 scopus 로고    scopus 로고
    • The intestinal anti-inflammatory effect of quercitrin is associated with an inhibition in iNOS expression
    • Camuesco D, Comalada M, Rodríguez-Cabezas M-E, et al. The intestinal anti-inflammatory effect of quercitrin is associated with an inhibition in iNOS expression. Br J Pharmacol 2004;143:908-18.
    • (2004) Br J Pharmacol , vol.143 , pp. 908-918
    • Camuesco, D.1    Comalada, M.2    Rodríguez-Cabezas, M.-E.3
  • 37
    • 11844279094 scopus 로고    scopus 로고
    • Dietary rutin, but not its aglycone quercetin, ameliorates dextran sulfate sodium-induced experimental colitis in mice: Attenuation of pro-inflammatory gene expression
    • Kwon H-K, Murakami A, Tanaka T, Ohigashi H. Dietary rutin, but not its aglycone quercetin, ameliorates dextran sulfate sodium-induced experimental colitis in mice: attenuation of pro-inflammatory gene expression. Biochem Pharmacol 2005;69:395-406.
    • (2005) Biochem Pharmacol , vol.69 , pp. 395-406
    • Kwon, H.-K.1    Murakami, A.2    Tanaka, T.3    Ohigashi, H.4
  • 38
    • 14744294057 scopus 로고    scopus 로고
    • In vivo quercitrin anti-inflammatory effect involves release of quercetin, which inhibits inflammation through down-regulation of the NF-kappaB pathway
    • Comalada M, Camuesco D, Sierra S, et al. In vivo quercitrin anti-inflammatory effect involves release of quercetin, which inhibits inflammation through down-regulation of the NF-kappaB pathway. Eur J Immunol 2005;35:584-92.
    • (2005) Eur J Immunol , vol.35 , pp. 584-592
    • Comalada, M.1    Camuesco, D.2    Sierra, S.3
  • 39
    • 84876729886 scopus 로고    scopus 로고
    • Quercetin-loaded microcapsules ameliorate experimental colitis in mice by anti-inflammatory and antioxidant mechanisms
    • Guazelli C-F, Fattori V, Colombo B-B, et al. Quercetin-loaded microcapsules ameliorate experimental colitis in mice by anti-inflammatory and antioxidant mechanisms. J Nat Prod 2013;76:200-8.
    • (2013) J Nat Prod , vol.76 , pp. 200-208
    • Guazelli, C.-F.1    Fattori, V.2    Colombo, B.-B.3
  • 40
    • 0037196147 scopus 로고    scopus 로고
    • Quercetin, but not its glycosides, is absorbed from the rat stomach
    • Crespy V, Morand C, Besson C, et al. Quercetin, but not its glycosides, is absorbed from the rat stomach. J Agric Food Chem 2002;50:618-21.
    • (2002) J Agric Food Chem , vol.50 , pp. 618-621
    • Crespy, V.1    Morand, C.2    Besson, C.3
  • 41
    • 2442430353 scopus 로고    scopus 로고
    • Polyphenols: Food sources and bioavailability
    • Manach C, Scalbert A, Morand C, et al. Polyphenols: food sources and bioavailability. Am J Clin Nutr 2004;79:727-47.
    • (2004) Am J Clin Nutr , vol.79 , pp. 727-747
    • Manach, C.1    Scalbert, A.2    Morand, C.3


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