Effects of chlorogenic acid and bovine serum albumin on the oxidative stability of low density lipoproteins in vitro

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Gordon, M. H. and Wishart, K. (2010) Effects of chlorogenic acid and bovine serum albumin on the oxidative stability of low density lipoproteins in vitro. Journal of Agricultural and Food Chemistry , 58 (9). pp. 5828-5833. ISSN 0021-8561 doi: 10.1021/jf100106e

Abstract/Summary

The ability of chlorogenic acid to inhibit oxidation of human low-density lipoprotein (LDL) was studied by in vitro copper-induced LDL oxidation. The effect of chlorogenic acid on the lag time before LDL oxidation increased in a dose dependent manner by up to 176% of the control value when added at concentrations of 0.25 -1.0 μM. Dose dependent increases in lag time of LDL oxidation were also observed, but at much higher concentrations, when chlorogenic acid was incubated with LDL (up to 29.7% increase in lag phase for 10 μM chlorogenic acid) or plasma (up to 16.6% increase in lag phase for 200 μM chlorogenic acid) prior to isolation of LDL, and this indicated that chlorogenic acid was able to bind, at least weakly, to LDL. Bovine serum albumin (BSA) increased the oxidative stability of LDL in the presence of chlorogenic acid. Fluorescence spectroscopy showed that chlorogenic acid binds to BSA with a binding constant of 3.88 x 104 M-1. BSA increased the antioxidant effect of chlorogenic acid, and this was attributed to copper ions binding to BSA, thereby reducing the amount of copper available for inducing lipid peroxidation.

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Item Type	Article
URI	https://reading-clone.eprints-hosting.org/id/eprint/5734
Item Type	Article
Refereed	Yes
Divisions	Life Sciences > School of Chemistry, Food and Pharmacy > Department of Food and Nutritional Sciences > Human Nutrition Research Group Interdisciplinary centres and themes > Chemical Analysis Facility (CAF)
Uncontrolled Keywords	antioxidant, bovine serum albumin, chlorogenic acid, low density lipoprotein, oxidation
Publisher	American Chemical Society
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Date Deposited:	05 May 2010 11:19	Date item deposited into CentAUR
Last Modified:	23 Jun 2024 03:01	Date item last modified

References

1. Steinberg, D. Low density lipoprotein oxidation and its pathobiological significance. J. Biol. Chem. 1997, 272, 20963-20966. 2. Hansson, G. K. Mechanism of disease: Inflammation, atherosclerosis, and coronary artery disease. N. Engl. J. Med. 2005, 352, 1685 – 95. 3. Siekmeier, R.; Steffen, C.; Marz W. Role of oxidants and antioxidants in atherosclerosis: Results of in vitro and in vivo investigations. J. Cardiovasc. Pharmacol. Ther. 2007, 12, 265-291. 4. Esterbauer, H.; Striegl, G.; Puhl, H.; Rothender M. Continuous montoring of in vitro oxidation of human low density lipoprotein. Free Rad. Res. Comm. 1989, 6, 67-75. 5. Schnitzer, E.; Pinchuk, I.; Bor, A.; Fainaru, M.; Lichtenberg, D. The effect of albumin on copper-induced LDL oxidation. Biochim. Biophys. Acta. 1997, 1344, 300-311. 6. Carr, A.C. ; Zhu, B.Z. ; Frei, B. Potential antiatherogenic mechanisms of ascorbate (vitamin C) and α-tocopherol (vitamin E). Circulation. 2000, 87, 349-354. 7. Wu, C.H.; Lin, J.A.; Hsieh, W.C.; Yen, G.C. Low-Density-Lipoprotein (LDL)-Bound Flavonoids Increase the Resistance of LDL to Oxidation and Glycation under Pathophysiological Concentrations of Glucose in Vitro. J.Agric.Food Chem. 2009, 57, 5058-5064. 8. Yukawa, G.S.; Mune, M.; Otani, H.; Tone, Y.; Liang, X.M.; Iwahashi, H.; Sakamoto, W. Effects of coffee consumption on oxidative susceptibility of low-density lipoproteins and serum lipid levels in humans. Biochem. (Mosc). 2004, 69, 70-74. 9. Farah, A.; Monteiro, M.; Donangelo, C.M.; Lafay, S. Chlorogenic Acids from Green Coffee Extract are Highly Bioavailable in Humans. J. Nutr. 2008, 138, 2309-2315. 10. Huang, B.X.; Kim, H.Y.; Dass, C. Probing three-dimensional structure of bovine serum albumin by chemical cross-linking and mass spectrometry. J.Amer.Soc.Mass Spec. 2004, 15, 1237-1247. 11. Rawel, H.M.; Frey, S.K.; Meidtner, K.; Kroll, J.; Schweigert, F.J. Determining the binding affinities of phenolic compounds to proteins by quenching of the intrinsic tryptophan fluorescence. Mol.Nutr.Food Res. 2006, 50, 705-713. 12. Rohn, S; Rawel, HM; Kroll, J. Antioxidant activity of protein-bound quercetin. J.Agric.Food Chem. 2004, 52, 4725-4729. 13. Leigh-Firbank, E.C.;, Minihane, A.M.; Leake, D.S.; Wright, J.W.; Murphy, M.C.; Griffin, B.A.; Williams, C.M.. Eicosapentanoic acid and docosahexanoic differential associations with lipid responses. Brit. J. Nutr. 2002, 87, 435-445. 14. Lowry, O.H.; Rosebrough, N.J.; Farr, A.L.; Randall, R.R. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951, 193, 265-275. 15. Soares, S.; Mateus, N.; Freitas, V. Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary α-amylase (HSA) by fluorescence quenching. J. Agric. Food Chem. 2007, 55, 6726-6735. 16. Johansson, J. S., Binding of the volatile anaesthetic chloroform to albumin demonstrated using tryptophan fluorescence quenching. J. Biol. Chem. 1997, 272, 17961 – 17965. 17. Kang , J.; Liu, Y.; Xie, M-X.; Li, S.; Jiang, M.; Wang, Y-D. Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim.Biophys.Acta 2004, 1674, 205-214. 18. Ivanov, V.; Carr, A.C.; Frei, B. 2001. Red wine antioxidants bind to human lipoproteins and protect them from metal ion-dependent and -independent oxidation. J.Agric.Food Chem. 2001, 49, 4442-4449. 19. Meyer, A.S., Donovan JL, Pearson DA, Waterhouse AL, Frankel EN. Fruit hydroxycinnamic acids inhibit human low-density lipoprotein oxidation in vitro. J. Agric. Food Chem. 1998, 46, 1783-1787. 20. Cheng, J.C.; Dai, F.; Zhou, B.; Yang, L.; Liu, Z.L. Antioxidant activity of hydroxycinnamic acid derivatives in human low density lipoprotein: mechanism and structure-activity relationship. Food Chem. 2007, 104, 132-139. 21. Rice-Evans, C.A.; Miller, N.J.; Paganga, G. Antioxidant properties of phenolic compounds. Trends Plant Sci. 1997, 2, 152-159. 22. Nardini, M.; Daquino, M.; Tomassi, G.; Gentili, V.; Difelice, M.; Scaccini, C. Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Radical Biol. Med. 1995, 19, 541-552. 23. Kiss, T.; Nagy, G.; Pecsi, M.; Kozlowski, H.; Micera, G.; Erre, L.S. Complexes of 3,4-dihydroxyphenyl derivatives- x copper(II)complexes of chlorogenic acid and related compounds. Polyhedron. 1989, 8, 2345-2349. 24. Roland, A.; Patterson, R.A.; Leake, D.S. Measurement of copper-binding sites on low density lipoprotein. Arterioscler., Thromb., Vasc. Biol. 2001, 21, 594-602. 25. Born, M.; Carrupt, P.A.; Zini, R.; Bree, F.; Tillement, J.P.; Hostetmann, K.; Testa, B. Electrochemical behaviour and antioxidant activity of some natural polyphenols. Helv.Chim.Acta. 1996, 79, 1147-1158. 26. Yang, C.Y., Chen, S.H., Gianturco, S.H., Bradley, W.A., Sparrow, J.T., Tanimura, M., Li, W.H., Sparrow, D.A., Deloof, H., Rosseneu, M., Lee, F.S., Gu, Z.W., Gotto, A.M., Chan, L. Sequence, structure, receptor-binding domains and internal repeats of human apolipoprotein-B-100. Nature, 1986, 323, 738-742. 27. Masuoka,J.; Hegenauer, J.; Vandyke, B.R.; Saltman P.. Intrinsic stoichiometric equilibrium constants for the binding of zinc(II) and copper(II) to the high affinity site of serum albumin. J. Biol. Chem. 1993, 268, 21533-21537. 28. Zgirski, A.; Frieden, E. A kinetic study on the distribution of Cu(II)-ions between albumin and transferrin. J. Inorg. Biochem. 1990, 39, 137-148. 29. Zhang Y, Akilesh S, Wilcox DE. Isothermal titration calorimetry measurements of Ni(II) and Cu(II) binding to His, GlyGlyHis, HisGlyHis, and bovine serum albumin: A critical evaluation. Inorg.Chem., 2000, 39, 3057-3064. 30. Ehrenwald, E.; Chisolm, G.M.; Fox, P.L. Intact human ceruloplasmin oxidatively modifies low density lipoproteins. J. Clin Invest. 1994, 93, 1493-1501. 31. Lamb, D.J.; Leake, D.S. Acidic pH enables ceruloplasmin to catalyse the modification of low density lipoprotein. FEBS Lett. 1994, 338, 122-126. 32. Wang, W.Q.; Goodman, M.T. Antioxidant property of dietary phenolic agents in a human LDL-oxidation ex vivo model: interaction of protein binding activity. Nutr. Res. 1999, 19, 191-202. 33. Giessauf, A.; Steiner, E.; Esterbauer, H. Early destruction of tryptophan residues of apolipoprotein B is a vitamin E-independent process during copper-mediated oxidation of LDL. Biochim. Biophys. Acta-Lipids and Lipid Metabolism, 1995, 1256, 221-232.

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