3-hydroxy-3-methylglutaryl coenzyme a reductase regulation by antioxidant compounds: New therapeutic tools for hypercholesterolemia?

Current Molecular Medicine

Volumn 11, Issue 9, 2011, Pages 790-797

  Trapani, L ^a   Segatto, M ^a   Incerpi, S ^a   Pallottini, V ^a  

^a ROMA TRE UNIVERSITY   (Italy)

Author keywords

Antioxidant; Cardiovascular disease; Cholesterol; HMGR; Hypercholesterolemia; Reactive oxygen species; Statins

Indexed keywords

ANTIOXIDANT; CARBOCROMEN; DAIDZEIN; DIOSGENIN; ESCULETIN; GENISTEIN; GINSENG SAPONIN; GINSENOSIDE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; NARINGENIN; OMEGA 3 FATTY ACID; QUERCETIN; REACTIVE OXYGEN METABOLITE; RESVERATROL;

ARTICLE; CORONARY ARTERY DISEASE; ENZYME REGULATION; FATIGUE; HUMAN; HYPERCHOLESTEROLEMIA; NONHUMAN; OXIDATIVE STRESS; RHABDOMYOLYSIS; WEAKNESS;

ANIMALS; ANTIOXIDANTS; HUMANS; HYDROXYMETHYLGLUTARYL-COA REDUCTASE INHIBITORS; HYDROXYMETHYLGLUTARYL-COA-REDUCTASES, NADP-DEPENDENT; HYPERCHOLESTEROLEMIA; LIPID METABOLISM; REACTIVE OXYGEN SPECIES; SIGNAL TRANSDUCTION;

EID: 81055137461     PISSN: 15665240     EISSN: 18755666     Source Type: Journal    
DOI: 10.2174/156652411798062403     Document Type: Article

References (80)

1. Chimenti F, Secci D, Bolasco A, Chimenti P, et al. Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-infstituted coumarins. J Med Chem 2009; 52: 1935-1942.
2. Madhavan GR, Balraju V, Mallesham B, Chakrabarti R, Lohray VB. Novel coumarin derivatives of heterocyclic compounds as lipid-lowering agents. Bioorg Med Chem Lett 2003; 13: 2547-2551.
3. Pallottini V, Montanari L, Cavallini G, Bergamini E, Gori Z, Trentalance A. Mechanisms underlying the impaired regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase in aged rat liver. Mech Ageing Dev 2004; 125: 633-639.
4. Pallottini V, Martini C, Bassi AM, Romano P, Nanni G, Trentalance A. Rat HMGCoA reductase activation in thioacetamide-induced liver injury is related to an increased reactive oxygen species content. J Hepatol 2006; 44: 368-374.
5. Pallottini V, Martini C, Cavallini G, et al. Age-related HMGCoA reductase deregulation depends on ROS-induced p38 activation. Mech Ageing Dev 2007; 128: 688-695.
6. Espenshade PJ, Hughes AL. Regulation of sterol synthesis in eukaryotes. Annu Rev Genet 2007; 41: 401-427.
7. Ravid T, Doolman R, Avner R, Harats D, Roitelman J. The ubiquitin-proteasome pathway mediates the regulated degradation of mammalian 3-hydroxy-3- methylglutarylcoenzyme A reductase. J Biol Chem 2000; 275: 35840-35847.
8. Cutler RG. The dysdifferentiative hypothesis of mammalian ageing and longevity, in The Ageing Brain, E. Jacobini et al, Ed., Raven Press, New York, NY, USA, 1982.
9. Istvan ES, Deisenhofer J. The structure of the catalytic portion of human HMG-CoA reductase. Biochim Biophys Acta 2000; 1529: 9-18.
10. Beg ZH, Stonik JA, Brewer HB Jr. Phosphorylation of hepatic 3-hydroxy-3-methylglutaryl coenzyme A reductase and modulation of its enzymic activity by calcium-activated and phospholipid-dependent protein kinase. J Biol Chem 1985; 260: 1682-1687.
11. Omkumar RV, Darnay BG, Rodwell VW. Modulation of Syrian hamster 3-hydroxy-3-methylglutaryl-CoA reductase activity by phosphorylation. Role of serine 871. J Biol Chem 1994; 269: 6810-6814.
12. Hardie DG, Hawley SA, Scott JW. AMP-activated protein kinase--development of the energy sensor concept. J Physiol 2006; 574: 7-15.
13. Hawley SA, Davison M, Woods A, et al. Characterization of the AMP-activated protein kinase kinase from rat liver and identification of threonine 172 as the major site at which it phosphorylates AMP-activated protein kinase. J Biol Chem 1996; 271: 27879-2787.
14. Janssens V, Goris J. Protein phosphatase 2A: a highly regulated family of serine/threonine phosphatases implicated in cell growth and signalling. Biochem J 2001; 353: 417-439.
15. Goldstein JL, DeBose-Boyd RA, Brown MS. Protein sensors for membrane sterols. Cell 2006; 124: 35-46.
16. Bengoechea-Alonso MT, Ericsson J. SREBP in signal transduction: cholesterol metabolism and beyond. Curr Opin Cell Biol 2007; 19: 215-222.
17. Brown MS, Goldstein JL. A proteolytic pathway that controls the cholesterol content of membranes, cells, and blood. Proc Natl Acad Sci USA 1999; 96: 11041-11048.
18. Yang T, Espenshade PJ, Wright ME, et al. Crucial step in cholesterol homeostasis: sterols promote binding of SCAP to INSIG-1, a membrane protein that facilitates retention of SREBPs in ER. Cell 2002; 110: 489-500.
19. Sever N, Yang T, Brown MS, Goldstein JL, De Bose-Boyd RA. Accelerated degradation of HMG CoA reductase mediated by binding of Insig-1 to its sterol-sensing domain. Mol Cell 2003; 1: 25-33
20. Goldstein JL, Brown MS. Regulation of the mevalonate pathway. Nature 1990; 343: 508-509.
21. Corsini A, Maggi FM, Catapano AL. Pharmacology of competitive inhibitors of HMG-CoA reductase. Pharmacol Res 1995; 31: 9-27.
22. Endo A, Kuroda M, Tanzawa K. Competitive inhibition of 3- hydroxy-3-methylglutaryl coenzyme A reductase by ML-236A and ML-236B fungal metabolites, having hypocholesterolemic activity. FEBS Lett 1976; 72: 323-326.
23. Istvan ES, Deisenhofer J. Structural mechanism for statin inhibition of HMG-CoA reductase. Science 2001; 292: 1160-1164.
24. Lahera V, Goicoechea M, de Vinuesa SG, et al. Endothelial dysfunction, oxidative stress and inflammation in atherosclerosis: beneficial effects of statins. Curr Med Chem 2007; 14: 243-248.
25. Tomlinson SS, Mangione KK. Potential adverse effects of statins on muscle. Phys Ther 2005; 85: 459-465.
26. Omkumar RV, Ramasarma T. Irreversible inactivation of 3- hydroxy-3-methylglutaryl-CoA reductase by H2O2. Biochim Biophys Acta 1993; 1156: 267-274.
27. Marino M, Pallottini V, D'Eramo C, Cavallini G, Bergamini E, Trentalance A. Age-related changes of cholesterol and dolichol biosynthesis in rat liver. Mech Ageing Dev 2002; 123: 1183-1189.
28. Stadtman ER. Protein oxidation and aging. Free Radic Res 2006; 40: 1250-1258.
29. Harman D. Origin and evolution of the free radical theory of aging: a brief personal history, 1954-2009. Biogerontology 2009; 10: 773-781.
30. Endres S, Ghorbani R, Kelly VE, et al. The effect of dietary supplementation with n-3 fatty acids on the synthesis of interleukin-1 and tumor necrosis factor by mononuclear cells. N Engl J Med 1989; 320: 265-270.
31. Holub BJ. Clinical nutrition: 4. omega-3 fatty acids in cardiovascular care. CMAJ 2002; 166: 608-615.
32. Leaf A, Kang JX, Xiao YF, Billman GE. Clinical prevention of sudden cardiac death by n-3 polyunsaturated fatty acids and mechanism of prevention of arrhythmias by n-3 fish oils. Circulation 2003; 107: 2646-2652.
33. Dallongeville J, Yamell J, Ducimetiere P. et al. Fish consumption is associated with lower heart rates. Circulation 2003; 108: 820-825.
34. Martini C, Pallottini V, De Marinis E, et al. Omega-3 as well as caloric restriction prevent the age-related modifications of cholesterol metabolism. Mech Ageing Dev 2008; 129: 722-727.
35. Sevov M, Elfineh L, Cavelier LB. Resveratrol regulates the expression of LXR-a in human macrophages. Biochem Biophys Res Commun 2006; 348: 1047-1054.
36. Auger C, Teissedre PL, Gerain P, et al. Dietary wine phenolics catechin, quercetin, and resveratrol efficiently protect hypercholesterolemic hamsters against aortic fatty streak accumulation. J Agric Food Chem 2005; 53: 2015-2021.
37. Fremont L, Belguendouz L, Delpal S. Antioxidant activity of resveratrol and alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated fatty acids. Life Sci 1999; 64: 2511-2521.
38. Wang Z, Huang Y, Zou J, Cao K, Xu Y, Wu JM. Effects of red wine and wine polyphenol resveratrol on platelet aggregation in vivo and in vitro. Int J Mol Med 2002; 9: 77-79.
39. Araim O, Ballantyne J, Waterhouse AL, Sumpio BE. Inhibition of vascular smooth muscle cell proliferation with red wine and red wine polyphenols. J Vasc Surg 2002; 35: 1226-1232.
40. Tsa SH, Lin-Shiau SY, Lin JK. Suppression of nitric oxide synthase and the down-regulation of the activation ofNFkappaB in macrophages by resveratrol. Br J Pharmacol 1999; 126: 673-680.
41. Avellone G, Di Garbo V, Campisi D, et al. Effects of moderate Sicilian red wine consumption on inflammatory biomarkers of atherosclerosis. Eur J Clin Nutr 2006; 60: 41-47.
42. Cho IJ, Ahn JY, Kim S, Choi MS, Ha TY. Resveratrol attenuates the expression of HMG-CoA reductase mRNA in hamsters. Biochem Biophys Res Commun 2008; 367: 190-194.
43. Sesso HD, Gaziano JM, Liu S, Buring JE. Flavonoid intake and the risk of cardiovascular disease in women. Am J Clin Nutr 2003; 77: 1400-1408.
44. Daniel RS, Devi KS, Augusti KT, Sudhakaran Nair CR. Mechanism of action of antiatherogenic and related effects of Ficus bengalensis Linn. flavonoids in experimental animals. Indian J Exp Biol 2003; 41: 296-303.
45. Gebhardt R. Variable influence of kaempferol and myricetin on in vitro hepatocellular cholesterol biosynthesis. Planta Med 2003; 69: 1071-1074.
46. Gebhardt R. Inhibition of cholesterol biosynthesis in HepG2 cells by artichoke extracts is reinforced by glucosidase pretreatment. Phytother Res 2002; 16: 368-372.
47. Hertog MG, Bueno-de-Mesquita HB, Fehily AM, Sweetnam PM, Elwood PC, Kromhout D. Fruit and vegetable consumption and cancer mortality in the Caerphilly study. Cancer Epidemiol Biomarkers Prev 1996; 5: 673-677.
48. Sestili P, Guidarelli A, Dacha M, Cantoni O. Quercetin prevents DNA single strand breakage and cytotoxicity caused by tert-butylhydroperoxide: free radical scavenging versus iron chelating mechanism. Free Radic Biol Med 1998; 25: 196-200.
49. Punithavathi VR, Prince PS. Combined effects of quercetin and alpha-tocopherol on lipids and glycoprotein components in isoproterenol induced myocardial infarcted Wistar rats. Chem Biol Interact 2009; 30: 322-327.
50. Ammer B, Weintraub RA, Johnson JV, Yost RA, Rouseff RL. Flavonone absorption after naringin, hesperidin, and citrus administration. Clin Pharmacol Ther 1996; 60: 34-40.
51. Griffiths LA, Smith GE. Metabolism of apigenin and related compounds in rat. Biochem J 1972; 128: 910-911.
52. Booth AN, Jones FT, Deeds F. Metabolic and glucosuria studies on naringin and phloridzin. J Biol Chem 1958; 233: 280-282.
53. Lee SH, Park YB, Bae KH, et al. Cholesterol-lowering activity of naringenin via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A:cholesterol acyltransferase in rats. Ann Nutr Metab 1999; 43: 173-180.
54. Sung JH, Lee SJ, Park KH, Moon TW. Isoflavones inhibit 3- hydroxy-3-methylglutaryl coenzyme A reductase in vitro. Biosci Biotechnol Biochem 2004; 68: 428-432.
55. Kim SY, Kim HJ, Lee MK, et al. Naringin time-dependently lowers hepatic cholesterol biosynthesis and plasma cholesterol in rats fed high-fat and high-cholesterol diet. J Med Food 2006; 9: 582-586.
56. Mène-Saffrané L, Della Penna D. Biosynthesis, regulation and functions of tocochromanols in plants. Plant Physiol Biochem 2010; 48: 301-309.
57. Khor HT, Chieng DY, Ong KK. Tocotrienols inhibit liver HMG Coa reductase activity in the guinea pig. Nutr Res 1995; 15: 537-544.
58. Qureshi AA, Burger WC, Peterson DM, Elson CE. The structure of an inhibitor of cholesterol biosynthesis isolated from barley. J Biol Chcm, 1986; 1: 10544-10550.
59. Watkins T, Len P, Gapor A, Struck M, Tomco A, Bicrenhaum M. Gamma-Tocotrienol as a hypocholestcrolemic and antioxidant agent in rats fed atherogenic diets. Lipids 1993; 28: 1113-1118.
60. Song BL, DeBose-Boyd RE. Insig-dependent Ubiquitination and Degradation of 3-Hydroxy-3 methylglutaryl Coenzyme A Reductase Stimulated by γ- and δ-Tocotrienols. J Biol Chem 2006; 281: 25054-25061.
61. Khor HT, Ng TT. Effects of administration of alpha-tocopherol and tocotrienols on serum lipids and liver HMG CoA reductase activity. Int J Food Sci Nutr 2000; 51 Suppl: S3-S11.
62. LÜ JM, Yao Q, Chen C. Ginseng compounds: An update on their molecular mechanisms and medical applications. Curr Vasc Pharmacol 2009; 7: 293-302.
63. Liu WK, Xu SX, Che CT. Anti-proliferative effect of ginseng saponins on human prostate cancer cell line. Life Sci 2000; 67: 1297-1306.
64. Baek NI, Kim DS. Lee YH, Park JD, Lee CB, Kim SI. Cytotoxicities of ginseng saponins and their degradation products against some cancer cell lines. Arch Pharm Res 1995; 18: 164-168.
65. Fu Y, Ji LL. Chronic ginseng consumption attenuates ageassociated oxidative stress in rats. J Nutr 2003; 133: 3603-3609.
66. Qureshi AA, Abuirmeileh N, Din ZZ, Ahmad Y, Burger WC, Elson CE. Suppression of cholesterogenesis and reduction of LDL cholesterol by dietary ginseng and its fractions in chicken liver. Atherosclerosis 1983; 48: 81-94.
67. Jayachandran KS, Vasanthi HR, Rajamanickam GV. Antilipoperoxidative and membrane stabilizing effect of diosgenin, in experimentally induced myocardial infarction. Mol Cell Biochem 2009; 327: 203-210.
68. McAnuff MA, Omoruyi FO, Morrison EY, Asemota HN. Hepatic functions enzymes and lipid peroxidation in streptozotocin-induced diabetic rats fed bitter yam (dioscorea polygonoides) steroidal sapogenin extract. Diabetologia Croatica 2003; 32: 17-23.
69. Levy RI, Bonnell M, Ernst ND. Dietary management of hyperlipoproteinemia. J Am Diet Assoc 1971; 58: 406-416.
70. Cayen MN, Dvornik D. Effect of diosgenin on lipid metabolism in rats. J Lipid Res 1979; 20: 162-174.
71. Raju J, Bird RP. Diosgenin, a naturally occurring steroid [correcetd] saponin suppresses 3-hydroxy- 3-methyilglutaryl CoA reductase expression and induces apoptosis in HCT-116 human colon carcinoma cells. Cancer Lett 2007; 255: 194-204.
72. Sashidhara KV, Kumar A, Kumar M, Sonkar R, Bhatia G, Khanna AK. Novel coumarin derivatives as potential antidyslipidemic agents. Bioorg Med Chem Lett 2010; 20: 4248-4251.
73. Sashidhara KV, Rosaiah JN, Kumar A, Bhatia G, Khanna AK. Synthesis of novel benzocoumarin derivatives as lipid lowering agents. Bioorg Med Chem 2010; 20: 3065-3069.
74. Borges F, Roleira F, Milhazes N, Sandtana L, Uriarte E. Simple coumarins and analogous in medicinal chemistry: occurrence, synthesis and biological activity. Curr Med Chem 2005; 12: 887-916.
75. Kostova I. Synthetic and natural coumarins as antioxidants. Mini Rev Med Chem 2006; 6: 365-374.
76. Natella F, Lorrain B, Prasad AK, Parmar VS, Saso L, Scaccini C. 4-Methylcoumarins as antioxidants: Scavenging of peroxyl radicals and inhibition of human low-density lipoprotein oxidation. Biochimie 2010; 92: 1147-1152.
77. Pedersen JZ, Oliveira C, Incerpi S, et al. Antioxidant activity of 4-methylcoumarins. J Pharm Pharmacol 2007; 59: 1721-1728.
78. Lin HC, Tsai SH, Chen CS, et al. Structure-activity relationship of coumarin derivatives on xanthine oxidaseinhibiting and free radical-scavenging activities. Biochem Pharmacol 2008; 75: 1416-1425.
79. Heynekamp JJ, Hunsaker LA, Vander Jagt TA, Royer RE, Deck LM, Vander Jagt DL. Isocoumarin-based inhibitors of pancreatic cholesterol esterase. Bioorg Med Chem 2008; 16: 5285-5294.
80. Trapani L, Segatto M, Simeoni V, et al. Short- and long-term regulation of 3-hydroxy 3-methylglutaryl coenzyme A reductase by a 4-methylcoumarin. Biochimie 2011; 93: 1165- 1171.