Interactive effects of polyphenols, tocopherol and ascorbic acid on the Cu2+-mediated oxidative modification of human low density lipoproteins

European Journal of Nutrition

Volumn 44, Issue 7, 2005, Pages 422-428

  Yeomans, Vera C ^a,b   Linseisen, Jakob ^a   Wolfram, Günther ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b NONE   (Germany)

Author keywords

Antioxidants; Ascorbic acid; Lipids; Low density lipoproteins; Oxidation; Polyphenols; Protein; Tocopherol

Indexed keywords

ALKADIENE; ALPHA TOCOPHEROL; ASCORBIC ACID; CAFFEIC ACID; CARBONYL DERIVATIVE; COPPER ION; EPICATECHIN; HESPERETIN; LOW DENSITY LIPOPROTEIN; PHLORETIN; POLYPHENOL DERIVATIVE; QUERCETIN; TRYPTOPHAN;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CONJUGATION; CONTROLLED STUDY; DRUG EFFECT; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; DRUG POTENTIATION; FLUORESCENCE; HUMAN; LIPID OXIDATION; LIPID PEROXIDATION; NORMAL HUMAN; STRUCTURE ACTIVITY RELATION;

ANTIOXIDANTS; ASCORBIC ACID; COPPER; DRUG INTERACTIONS; DRUG SYNERGISM; FLAVONOIDS; HUMANS; KINETICS; LIPID PEROXIDATION; LIPOPROTEINS, LDL; OXIDATION-REDUCTION; PHENOLS; TOCOPHEROLS;

EID: 26244443700     PISSN: 14366207     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00394-005-0546-y     Document Type: Article

References (44)

1. Morton LW, Abu-Amsha CR, Puddey IB, Croft KD (2000) Chemistry and biological effects of dietary phenolic compounds: relevance to cardiovascular disease. Clin Exp Pharmacol Physiol 27:152-159
2. Noguchi N, Niki E (2000) Phenolic antioxidants: a rationale for design and evaluation of novel antioxidant drug for atherosclerosis. Free Radic Biol Med 28:1538-1546
3. Halliwell B (1994) Free radicals, antioxidants, and human disease: curiosity, cause, or consequence? Lancet 344:721-724
4. Pinchuk I, Gal S, Lichtenberg D (2001) The dose-dependent effect of copper-chelating agents on the kinetics of peroxidation of low-density lipoprotein (LDL). Free Radic Res 34:349-362
5. Esterbauer H, Ramos P (1996) Chemistry and pathophysiology of oxidation of LDL. Rev Physiol Biochem Pharmacol 127:31-64
6. Halliwell B, Gutteridge JM (1990) The antioxidants of human extracellular fluids. Arch Biochem Biophys 280:1-8
7. Croft KD (1998) The chemistry and biological effects of flavonoids and phenolic acids. Ann N Y Acad Sci 20(854):435-442
8. Evans PJ, Smith C, Mitchinson MJ, Halliwell B (1995) Metal ion release from mechanically-disrupted human arterial wall. Implications for the development of atherosclerosis. Free Radic Res 23:465-469
9. Smith C, Mitchinson MJ, Aruoma OI, Halliwell B (1992) Stimulation of lipid peroxidation and hydroxyl-radical generation by the contents of human atherosclerotic lesions. Biochem J 286:901-905
10. Halliwell B, Aeschbach R, Loliger J, Aruoma OI (1995) The characterization of antioxidants. Food Chem Toxicol 33:601-617
11. Havel RJ, Eder HA, Bragdon JH (1955) The distribution and chemical composition of ultracentrifugally seperated lipoproteins in human serum. J Clin Invest 34:1345-1353
12. Lowry OH, Rosebrough NJ, Farr L, Randall RJ (1951) Protein measurement with the folin phenol reagent. J Biol Chem 193:265-275
13. Hess D, Keller HE, Oberlin B, Bonfanti R, Schuep W (1991) Simultaneous determination of retinol, tocopherols, carotenes and lycopene in plasma by means of high-performance liquid chromatography on reversed phase. Int J Vitam Nutr Res 61:232-238
14. Esterbauer H, Striegl G, Puhl H, Rotheneder M (1989) Continuous monitoring of in vitro oxidation of human low density lipoprotein. Free Radic Res Commun 6:67-75
15. Yan LJ, Traber MG, Packer L (1995) Spectrophotometric method for determination of carbonyls in oxidatively modified apolipoprotein B of human low-density lipoproteins. Anal Biochem 228:349-351
16. Reznick AZ, Packer L (1994) Oxidative damage to proteins: spectrophotometric method for carbonyl assay. Methods Enzymol 233:357-363
17. Yan LJ, Lodge JK, Traber MG, Packer L (1997) Apolipoprotein B carbonyl formation is enhanced by lipid peroxidation during copper-mediated oxidation of human low-density lipoproteins. Arch Biochem Biophys 339:165-171
18. Horakova L, Giessauf A, Raber G, Esterbauer H (1996) Effect of stobadine on Cu(++)-mediated oxidation of low-density lipoprotein. Biochem Pharmacol 51:1277-1282
19. Giessauf A, Steiner E, Esterbauer H (1995) Early destruction of tryptophan residues of apolipoprotein B is a vitamin E-independent process during copper-mediated oxidation of LDL. Biochim Biophys Acta 1256:221-232
20. Cao G, Sofic E, Prior RL (1996) Antioxidant capacity of tea and common vegetables. J Agric Food Chem 44:3426-3431
21. Wang H, Cao G, Prior RL (1996) Total antioxidant capacity of fruits. J Agric Food Chem 44:701-705
22. Manach C, Morand C, Crespy V, Demigne C, Texier O, Regerat F, Rémésy C (1998) Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett 426:331-336
23. Radtke J, Linseisen J, Wolfram G (2002) Fasting plasma concentrations of selected flavonoids as markers of their ordinary dietary intake. Eur J Nutr 41(5):203-209
24. Erlund I, Meririnne E, Alfthan G, Aro A (2001) Plasma kinetics and urinary excretion of the flavanones naringenin and Hesperetin in humans after ingestion of orange juice and grapefruit juice. J Nutr 131:235-241
25. Rein D, Lotito S, Holt R, Keen CL, Schmitz HH, Fraga CG (2000) Epicatechin in human plasma: in vivo determination and effect of chocolate consumption on plasma oxidation status. J Nutr 130:2109S-2114S
26. Lee MJ, Maliakal P, Chen L, Meng X, Bondoc FY, Prabhu S, Lambert G, Mohr S, Yang CS (2002) Pharmacokinetics of tea catechins after ingestion of green tea and (-)-epigallocatechin-3-gallate by humans: formation of different metabolites and individual variability. Cancer Epidemiol Biomarkers Prev 11(10 Pt 1):1025-1032
27. Paganga G, Rice-Evans CA (1997) The identification of flavonoids as glycosides in human plasma. FEBS Lett 13; 401(1):78-82
28. Böhm H, Boeing H, Hempel J, Raab B, Kroke A (1998) Flavonols, flavone and anthocyanins as natural antioxidants of food and their possible role in the prevention of chronic diseases. Z Ernährungswiss 37:147-163
29. Laranjinha J, Cadenas E (1999) Redox cycles of caffeic acid, alpha-tocopherol, and ascorbate: implications for protection of low-density lipoproteins against oxidation. IUBMB Life 48:57-65
30. Sekher PA, Chan TS, O'Brien PJ, Rice-Evans CA (2001) Flavonoid b-ring chemistry and antioxidant activity: fast reaction kinetics. Biochem Biophys Res Commun 282:1161-1168
31. van Acker SA, Bast A, van der Vijgh WJF (1998) Structural aspects of antioxidant activity of flavonoids. In: Rice-Evans CA, Packer L (eds) Flavonoids in health and disease. Marcel Dekker Inc., New York, pp 221-252
32. Rice-Evans CA, Miller NJ, Paganga G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20:933-956
33. Pietta PG (2000) Flavonoids as antioxidants. J Nat Prod 63:1035-1042
34. Rice-Evans C, Miller NJ (1998) Structure-Antioxidant Activity Relationships of Flavonoids and Isoflavonoids. In: Rice-Evans C, Packer L (eds) Flavonoids in Health and Disease. Marcel Dekker, Inc., New York, pp 199-219
35. Bors W, Michel C, Schikora S (1995) Interaction of flavonoids with ascorbate and determination of their univalent redox potentials: a pulse radiolysis study. Free Radic Biol Med 19:45-52
36. Cossins E, Lee R, Packer L (1998) ESR studies of vitamin C regeneration, order of reactivity of natural source phytochemical preparations. Biochem Mol Biol Int 45:583-597
37. Jovanovic SV, Steenken S, Simic MG, Hara Y (1998) Antioxidant properties of flavonoids: reduction potentials and electron transfer reactions of flavonoid radicals. In: Rice-Evans C, Packer JE (eds) Flavonoids in health and disease. Marcel Dekker, Inc, New York, pp 137-161
38. Kandaswami C, Perkins E, Soloniuk DS, Drzewiecki G, Middleton EJ (1993) Ascorbic acid-enhanced antiproliferative effect of flavonoids on squamous cell carcinoma in vitro. Anticancer Drugs 4:91-96
39. Jovanovic SV, Steenken S, Tosic M, Marjanovic B, Simic MG (1994) Flavonoids as antioxidants. J Am Chemical Society 116:4846-4851
40. Steenken S, Neta P (1982) One-electron redox potentials of phenols. Hydroxy-and aminophenols and related compounds of biological interest. J Physical Chemistry 86:3661-3667
41. Buettner GR, Jurkiewicz BA (1993) Ascorbate free radical as a marker of oxidative stress: an EPR study. Free Radic Biol Med 14:49-55
42. Frei B, Keaney JF, Retsky KL, Chen K (1996) Vitamins C and E and LDL oxidation. Vitam Horm 52:1-34
43. Esterbauer H, Dieber-Rotheneder M, Striegl G, Waeg G (1991) Role of vitamin E in preventing the oxidation of low-density lipoprotein. Am J Clin Nutr 53:314S-321S
44. Terao J, Piskula M (1997) Flavonoids as inhibitors of lipid peroxidation in membranes. In: Rice-Evans C, Packer JE (eds) Flavonoids in health and disease. Marcel Dekker Inc, New York, pp 277-294