Effects of 2,3-diketo-L-gulonic acid on the oxidation of yolk lipoprotein

Bioscience, Biotechnology and Biochemistry

Volumn 65, Issue 3, 2001, Pages 599-604

  Li, Meihua ^a   Suzuki, Emiko ^a   Kurata, Tadao ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

2,3 diketo L gulonic acid; 3,4 enediol or 2,3 enediol form of DKG lactones; Copper; Oxidized YLP

Indexed keywords

2,3 DIOXOGULONIC ACID; ANTIOXIDANT; COPPER; EGG PROTEIN; LIPOPROTEIN;

ARTICLE; METABOLISM; OXIDATION REDUCTION REACTION; SOLUTION AND SOLUBILITY;

2,3-DIKETOGULONIC ACID; ANTIOXIDANTS; COPPER; EGG PROTEINS; LIPOPROTEINS; OXIDATION-REDUCTION; SOLUTIONS;

EID: 0035291502     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.65.599     Document Type: Article

References (30)

1. Ames, B. N. and Shigenaga, M. K., Oxidants are a major contributor to aging. Ann. N.Y. Acad. Sci., 663, 85-96 (1992).
2. Steinber, D., Parthasarathy, S., Carew, T. E., Khoo, J. C., and Witztum, J. L., Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med., 320, 915-924 (1989).
3. Esterbauer, H., Gebicki, J., Puhl, H., and Jurgens, G., The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radical Biol. Med., 13, 341-390 (1992).
4. Keaney, J. F. Jr. and Frei, B., Antioxidant protection of low-density lipoprotein and its role in the prevention of atherosclerotic vascular disease. In: Frei, B., ed. Natural antioxidants in human health and disease, San Diego: Academic Press, pp. 303-351 (1994).
5. Halliwell, B., Oxidation of low-density lipoproteins: questions of initiation, propagation, and the effect of antioxidants. Am. J. Clin. Nutr., 61, 670S-677S (1995).
6. Frei, B., Ascorbic acid protects lipids in human plasma and low-density lipoprotein against oxidative damage. Am. J. Clin. Nutr., 54, 1113S-1118S (1991).
7. Frei, B., England, L., and Ames, B. N., Ascorbate is an outstanding antioxidant in human blood plasma. Proc. Natl. Acad. Sci. USA, 86, 6377-6381 (1989).
8. Kagawa, Y., Enzymatic studies on ascorbic acid catabolism in animals, I. Catabolism of 2,3-diketo-L-gulonic acid. J. Biochem., 51, 134-144 (1962).
9. Omaye, S. T., Tillotson, J. A., and Sauberlich, H. E., Metabolism of L-ascorbic acid in the monkey. In "Ascorbic acid: chemistry, metabolism, and uses", ACS Advances in chemistry series No. 200, eds. by Seib, P. A. and Tolbert, B. M., American chemical society, Washington, D.C., pp. 317-334 (1982).
10. Levine, M. and Morita, K., Ascorbic acid endocrine systems. Vitamins and Hormones, 42, 1-64 (1985).
11. Retsky, K. L., Freeman, M. W., and Frei, B., Ascorbic acid oxidation product(s) protect human low density lipoprotein against atherogenic modification. J. Biol. Chem., 268, 1304-1309 (1993).
12. Retsky, K. L. and Frei, B., Vitamin C prevents metal ion-dependent initiation and propagation of lipid peroxidation in human low-density lipoprotein. Biochim. Biophys. Acta, 1257, 279-287 (1995).
13. Ostuka, M., Kurata, T., and Arakawa, N., Isolation and characterization of an intermediate product in the degradation of 2,3-diketo-L-gulonic acid. Agric. Biol. Chem., 50, 531-533 (1986).
14. Takagi, M., Kawajiri, A., Nakata, K., and Morita, N., Behavior of 3,4-endiol form of 2,3-dikerogulono-δ-lactone formed from dehydro-L-ascorbic acid in deoxygenated and neutral solution. J. Nutr. Sci. Vitaminol., 35, 61-70 (1989).
15. Tanaka, H. and Kimoto, E., Preparation and characterization of a 345 nm absorbing reductant derived from dehydro-L-ascorbic acid. Bull. Chem. Soc. Jpn., 63, 2569-2572 (1990).
16. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J., Protein measurement with the Folin phenol reagent. J. Biol. Chem., 193, 265-275 (1951).
17. Esterbauer, H., Striegl, G., Puhl, H., and Rotheneder, M., Continuous monitoring of in vitro oxidation of human Low density Lipoprotein. Free Rad. Res. Comms., 6, 67-75 (1988).
18. Niki, E., Saito, M., Yoshikawa, Y., Yamamoto, Y., and Kamiya, Y., Oxidation of lipid. XII. Inhibition of oxidation of soybean phosphatidlcholine and methyl linoleate in aqueous dispersions by uric acid. Bull. Chem. Soc. Jpn., 59, 471-477 (1986).
19. Frei, B., Stocker, R., and Ames, B, N., Antioxidant defenses and lipid peroxidation in human blood plasma. Proc. Natl. Acad. Sci. USA, 85, 9748-9752 (1988).
20. Roe, J. H., Mills, M. B., Oesterling, and Damron, C. M., The determination of diketo-L-gulonic acid, dehydro-L-ascorbic acid, and L-ascorbic acid in the same tissue extract by the 2,4-dinitrophenyl-hydrazine method. J. Biol. Chem., 174, 201-208 (1948).
21. Steinbrecher, U. P., Oxidation of human low density lipoprotein results in derivatization of lysine residues of apolipoprotein B by lipid peroxide decomposition products. J. Biol. Chem., 262, 3603-3608 (1987).
22. Uchida, K. and Kawakishi, S., 2-oxo-histidine as a novel biological marke for oxidatively modified proteins. FEBS Lett., 332, 208-210 (1993).
23. Lynch, S. M. and Frei, B., Reduction of copper, but not iron, by human low density lipoprotein (LDL). J. Biol. Chem., 270, 5158-5163 (1995).
24. Lynch, S. M. and Frei, B., Mechanisms of copper-and iron-dependent oxidative modification of human low density lipoprotein. J. Lipid Res., 34, 1745-1753 (1993).
25. Kuzuya, M., Yamada, K., Hayashi, T., Funaki, C., Naito, M., Asai, K., and Kuzuya, F., Role of lioprotein-copper complex in copper catalyzed-peroxidation of low-density lioprotein. Biochim. Biophys. Acta, 1123, 334-341 (1992).
26. Scarpa, M., Stevanato, R., Viglino, P., and Rigo, A., Superoxide ion as active intermediate in the autoxidation of ascorbate by molecular oxygen. J. Biol. Chem., 258, 6695-6697 (1983).
27. Miyake, N., Kim, M., and Kurata, T., Formation mechanism of monodehydro-L-ascorbic acid and superoxide anion in the autoxidation of L-ascorbic acid. Biosci. Biotechnol. Biochem., 61, 1693-1695 (1997).
28. Miller, D. C., Buettner, G. R., and Aust, S. D., Transition metals as catalysts of "autoxidation" reaction. Free Radical Biol. Med., 8, 95-108 (1990).
29. Buettner, G. R., Ascorbate autoxidation in the presence of iron and copper chelates. Free Rad. Res. Comms., 1, 349-353 (1986).
30. Miyake, N. and Kurata, T., Possible formation of dehydro-L-ascorbic acid from 2,3-diketo-L-gulonic acid in an aqueous solution. Biosci. Biotechnol. Biochem., 62, 1419-1421 (1998).