The inhibitory effects of bioactive compounds of Tomato juice binding to hepatic HMGCR: In vivostudy and molecular modelling

PLoS ONE

Volumn 9, Issue 1, 2014, Pages

  Navarro González, Inmaculada ^a   Pérez Sánchez, Horacio ^b   Martín Pozuelo, Gala ^a   García Alonso, Javier ^a   Periago, Maria Jesús ^a  

^a UNIVERSITY OF MURCIA   (Spain)

^b CATHOLIC UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 3 METHYLGLUTARYL COENZYME A; CHLOROGENIC ACID; CHOLESTEROL; HIGH DENSITY LIPOPROTEIN CHOLESTEROL; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; LOW DENSITY LIPOPROTEIN CHOLESTEROL; LYCOPENE; NARINGENIN; TRIACYLGLYCEROL; WATER;

ANIMAL EXPERIMENT; ARTICLE; BINDING COMPETITION; BIOACCUMULATION; CHOLESTEROL BLOOD LEVEL; CHOLESTEROL SYNTHESIS; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INHIBITION; FOOD INTAKE; GENE EXPRESSION; IN VIVO STUDY; LIVER LEVEL; MALE; MOLECULAR MODEL; NONHUMAN; PROTEIN EXPRESSION; RAT; SPRAGUE DAWLEY RAT; TOMATO JUICE; TRIACYLGLYCEROL BLOOD LEVEL;

ANIMALS; ANTIOXIDANTS; BEVERAGES; CAROTENOIDS; ENZYME ACTIVATION; FOLIC ACID; HYDROXYMETHYLGLUTARYL COA REDUCTASES; LIGANDS; LIPIDS; LIVER; LYCOPERSICON ESCULENTUM; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR DOCKING SIMULATION; PHENOLS; PLANT EXTRACTS; PROTEIN BINDING; RATS;

EID: 84895419584     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0083968     Document Type: Article

References (46)

1. Di Mascio P, Kaiser S, Sies H (1989) Lycopene as the most efficient biological carotenoid singlet oxygen quencher. Arch. Biochem. Biophy 274:5352538.
2. Willcox JK, Catignani GL, Lazarus S (2003) Tomatoes and cardiovascular health. CRC Crit. Rev. Food Sci. Nutr 43:1-18. (Pubitemid 38552309)
3. Periago MJ, Garcia-Alonso J, Jacob K, Belen Olivares A, Berna MJ, et al. (2009) Bioactive compounds, folates and antioxidant properties of tomatoes (Lycopersicum esculentum) during vine ripening. Int. J. Food Sci. Nutr 60:694-708.
4. Garćia-Valverde V, Navarro-González I, García-Alonso J, Periago MJ (2013) Antioxidant bioactive compounds in selected industrial processing and fresh consumption tomato cultivars. Food Bioprocess. Technol 6:391-402.
5. Rao AV, Waseem Z, Agarwal S (1998) Lycopene content of tomatoes and tomato products and their contribution to dietary lycopene. Food Res. Int 31:737-741. (Pubitemid 29298273)
6. Arab L, Steck S (2000) Lycopene and cardiovascular diseases. Am. J. Clin. Nutr 71:1691S-1695S.
7. Sesso HD, Wang L, Ridker PM, Buring JE (2012) Tomato-based food products are related to clinically modest improvements in selected coronary biomarkers in women. J. Nutr 142:326-333
8. Mordente A, Guantario B, Meucci E, Silvestrini A, Lombardi E, et al. (2011) Lycopene and cardiovascular diseases: an update. Curr. Med. Chem. 18:1146-1163.
9. Palozza P, Parrone N, Catalano A, Simone R (2010) Tomato lycopene and inflammatory cascade: basic interactions and clinical implications. Curr. Med. Chem 17:2547-2563.
10. Jacob K, Periago MJ, Böhm V, Berruezo G (2008) Influence of lycopene and vitamin C from tomato juice on biomarkers of oxidative stress and inflammation. Brit. J. Nutr 99:137-146. (Pubitemid 350286147)
11. Fuhrman B, Elis A, Aviram M (1997) Hypocholesterolemic effect of lycopene and β-carotene is related to suppression of cholesterol synthesis and augmentation of LDL receptor activity in macrophages. Biochem. Biophys. Res. Commun 233:658-662. (Pubitemid 27217707)
12. Silaste ML, Alfthan G, Aro A, Kesäniemil YA, Hörkkö S (2007) Tomato juice decreased LDL cholesterol levels and increased LDL resistence to oxidation. Brit. J. Nutr 98:1251-1258. (Pubitemid 350193793)
13. Hsu YM, Lai CH, Chang CY, Fan CT, Chen CT, et al. (2008) Characterizing the lipid lowering effects and antioxidant mechanisms of tomato paste. Biosci. Biotechnol. Biochem 72:677-685.
14. García-Alonso FJ, Jorge-Vidal V, Ros G, Periago MJ (2012) Effect of consumption of tomato juice enriched with ω-3 polyunsaturated fatty acids on the lipid profile, antioxidant biomarker status, and cardiovascular disease risk in healthy women. Eur. J. Nutr 5:415-424.
15. 2 and monocyte chemotactic protein-1 in healthy humans. J. Nutr. Biochem 17:183-189. (Pubitemid 43247412)
16. Rao AV, Rao LG (2007) Carotenoids and human health. Pharmacol. Res 55:207-216. (Pubitemid 46518154)
17. Palozza P, Simone R, Catalano A, Parrone N, Monego G, et al. (2011) Lycopene regulation of cholesterol synthesis and efflux in human macrophages. J. Nutr. Bioch 22:971-978.
18. Ried K, Fakler P (2011) Protective effect of lycopene on serum cholesterol and blood pressure: meta-analyses of intervention trials. Maturitas 68:299-310.
19. Chen ZY, Jiao R, Ma KY (2008) Cholesterol-lowering nutraceuticals and functional foods. J. Agric. Food Chem 56:8761-8773.
20. Lee SH, Park YB, Bae KH, Bok SH, Kwon YK, et al, (1999) Cholesterollowering activity of naringenin via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A: cholesterol acyltransferase in rats. Ann. Nutr. Metab 43:173-180. (Pubitemid 29494862)
21. Karthikesan K, Pari L, Menon VP (2010) Antihyperlipidemic effect of chlorogenic acid and tetrahydrocurcumin in rats subjected to diabetogenic agents. Chem. Biol. Interact 188:643-650.
22. 30 high performance liquid chromatography. J. Sep. Sci. 24:9552959.
23. Fröhlich K, Conrad J, Schmid A, Breithaupt DE, Böhm V, et al. (2007) Isolation and structural elucidation of different geometrical isomers of lycopene. Internat. J. Vit. Nutr. Res 77:3692375.
24. 14C]Caffeic acid in rats. J. Agric. Food Chem 60:520525214.
25. Venugopala RA, Ramakishnan S (1975) Indirect assessment of Hydroxymethylglutaryl-CoA reductase (NADPH) activity in liver Tissue. Clin. Chem 21:1523-1525.
26. Livak KJ, Schmittegen TD (2001) Analysis of relative gene expression data using real-time quantitative PCR and the 2-[Delta][Delta]CT method. Methods 25:402-408. (Pubitemid 34164012)
27. Navarro-Fernández J, Pérez-Sánchez H, Mart́inez-Mart́inez I, Meliciani I, Guerrero JA, et al. (2012) In silico discovery of a compound with nanomolar affinity to antithrombin causing partial activation and increased heparin affinity. J. Med. Chem 55:6403-6412.
28. Stroganov OV, Novikov FN, Stroylov VS, Kulkov V, Chilov GG, et al. (2008) Lead finder: an approach to improve accuracy of protein-ligand docking, binding energy estimation, and virtual screening. J. Chem. Inf. Model 48:2371-2385.
29. Wang J, Cieplak P, Kollman PA (2000) How well does a restrained electrostatic potential (RESP) model perform in calculating conforma-tional energies of organic and biological molecules? J. Comput. Chem 21:1049-1074.
30. Hazai E, Bikadi Z, Zsila F, Lockwood SF (2006) Molecular modelling of the non-covalent binding of the dietary tomato carotenoids lycopene and lycophyll, and selected oxidative metabolites with 5-lipoxygenase. Bioorgan. Med. Chem. 14:6859-6867. (Pubitemid 44307652)
31. Istvan E, Palnitkar M, Buchanan S, Deisenhofer J (2000) Crystal structure of the catalytic portion of human HMG-CoA reductase: insights into regulation of activity and catalysis. Embo. J. 19:819-830. (Pubitemid 30119808)
32. Leopoldini M, Malaj N, Toscano M, Sindona G, Russo N (2010) On the inhibitor effects of bergamot juice flavonoids binding to the 3-hydroxy-3-methylglutaryl-CoA Reductase (HMGR) enzyme. J. Agric. Food Chem 58:10768-10773.
33. Richelle M, Sánchez B, Tavazzi I, Lambelet P, Bortlik K, et al. (2010) Lycopene isomerization takes place within enterocytes during absorption in human subjects. Brit. J. Nutr. 103:1800-1807.
34. Gonthier MP, Verny MA, Besson C, Rémésy C (2003) Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J. Nutr 133:1853-1859. (Pubitemid 36666525)
35. Lafay S, Morand C, Manach C, Besson C, Scalbert A (2006a) Absorption and metabolism of caffeic acid and chlorogenic cid in the small intestine of rats. Br. J. Nutr 96:39-46. (Pubitemid 44160894)
36. Lafay S, Gil-Izquierdo A, Manach C, Morand C, Besson C, et al. (2006b) Chlorogenic acid is absorbed in its intact form in the stomach of rats. J. Nutr 136:1192-1197.
37. Felgines C, Texier O, Morand C, Manach C, Scalbert A, et al. (2000) Bioavailability of the flavanone naringenin and its glycosides in rats. Am. J. Physiol. Gastrointest. Liver Physiol 279:G1148-1154.
38. Istvan ES, Deisenhofer L (2001) Structural mechanism for statin inhibition of HMGCoA reductase. Science 232:1160-1164. (Pubitemid 32440937)
39. Brown MS, Goldstein JL (1980) Multivalent feedback regulation of HMGCoA reductase, a control mechanism coordinating isoprenoid synthesis and cell growth. J. Lipid. Res 21:505-517. (Pubitemid 11194847)
40. Bilheimer DW, Grundy SM, Brown MS, Goldstein JL (1989) Mevinolin and colestipol stimulate receptor-mediated clearance of low density lipoprotein from plasma in familiar hypercholesterolemia heterozygote. Pro. Natl. Acad. Sci. USA 80:4142-228.
41. Gark VK, Douglas TJ (1983) Hydroxymethylglutaryl-CoA reductase in plants. In: Sabine JR, editor. Hydroxymethylglutaryl-CoA reductase. Boca Raton (Fla): CRC Press: 29-37.
42. Hu MY, Li MS, Jiang CH, Liu ZQ, Qu SL, et al. (2008) Comparison of lycopene and fluvastatin effects on atherosclerosis induced by a high-fat diet in rabbits. Nutrition 24:1030-1038.
43. Rai SK, Sharma M, Tiwari M (2009) Inhibitory effect of novel diallyldisulfide analogs on HMG-CoA reductase expression in hypercholesterolemic rats: CREB as a potential upstream target. Life Sci 85:211-219.
44. Beg ZH, Allman DW, Gibson DM (1973) Modulation of 3-hydroxy- emethylglutaryl coenzyme A reductase activity with cAMP and with protein fractions of rat liver cytosol. Biochem. Biophys. Res. Commun 54:1362-1369.
45. Forman BM, Ruan B, Chen J, Schroepfer GJJ, Evans RM (1997) The orphan nuclear receptor LXRs is positively and negatively regulated by distintct products of mevalonate metabolism. Proc. Natl. Acad. Sci. USA 94:10588-10593.
46. Li AC, Glass CK (2004) PPAR- and LXR-dependent pathways controlling lipid metabolism and the development of atherosclerosis. J. Lipid Res 45:2161-2173. (Pubitemid 39602963)