Antioxidative properties of a newly synthesized 2-glucosamine-thiazolidine-4(R)-carboxylic acid (GlcNH2Cys) in mice

Nutrition Research

Volumn 26, Issue 7, 2006, Pages 369-377

  Yan, Yang ^a   Wan Shun, Liu ^a   Bao Qin, Han ^a   Hai Zhou, Sun ^a  

^a OCEAN UNIVERSITY OF CHINA   (China)

Author keywords

2 glucosamine thiazolidine 4(R) carboxylic acid; Acetaminophen; Antioxidant; Free radical; Lipid peroxidation; Mice; Oxidative stress

Indexed keywords

2 GALACTOTHIAZOLIDINE CARBOXYLIC ACID; 2 GLUCOSAMINE THIAZOLIDINE 4 CARBOXYLIC ACID; 2 GLUCOTHIAZOLIDINE CARBOXYLIC ACID; ANTIOXIDANT; CARBOXYLIC ACID DERIVATIVE; DEOXYRIBOSE; HYDROXYL RADICAL; LIPID; PARACETAMOL; PROTEIN; SCAVENGER; SUPEROXIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; LIPID PEROXIDATION; LIVER INJURY; LIVER PROTECTION; MALE; MOUSE; NONHUMAN; OXIDATIVE STRESS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL;

EID: 33747766518     PISSN: 02715317     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nutres.2006.06.014     Document Type: Article

References (42)

1. Singla A.K., and Chawla M. Chitosan: some pharmaceutical and biological aspects-an update. J Pharm Pharmacol 53 8 (2001) 1047-1067
2. Jiang Y., Xue P.H., Chen S.M., and Li W.J. The inhibitory effect of chitosan to superoxide anion and LOO. Sci Bull 47 3 (2002) 182-184
3. Chiang M.T., Yao H.T., and Chen H.C. Effect of dietary chitosans with different viscosity on plasma lipids and lipid peroxidation in rats fed on a diet enriched with cholesterol. Biosci Biotechnol Biochem 64 5 (2000) 965-971
4. Jeon T.I., Hwang S.G., Park N.G., Jung Y.R., Shin S.I., Choi S.D., et al. Antioxidative effect of chitosan on chronic carbon tetrachloride induced hepatic injury in rats. Toxicology 187 1 (2003) 67-73
5. Xie W., Xu P.X., and Liu Q. Antioxidant activity of water-soluble chitosan derivatives. Bioorg Med Chem Lett 11 13 (2001) 1699-1701
6. Sal'nikova S.I., Drogovoz S.M., and Zupanets I.A. The liver-protective properties of d-glucosamine. Farmakol Toksikol 53 4 (1990) 33-35
7. Roberts J.C., Koch K.E., Detrick S.R., Waters R.L., and Lubec G. Thiazolidine prodrugs of cysteamine and cysteine as radio-protective agents. Radiat Res 143 2 (1995) 203-213
8. Zhang Y.L., Sun C.J., Chen Z.C., Li X.G., and Wang R.C. Synthesis and antitumor activities of some glycosyl derivatives of thiazolidine-4-carboxylic acid. Yiyao Gongye 19 4 (1988) 152-154
9. Rathbun W.B., Killen C.E., Holleschau A.M., and Nagasawa H.T. Maintenance of hepatic glutathione homeostasis and prevention of acetaminophen-induced cataract in mice by l-cysteine prodrugs. Biochem Pharmacol 51 9 (1996) 1111-1116
10. Rathbun W.B., Nagasawa H.T., and Killen C.E. Prevention of naphthalene-induced cataract and hepatic glutathione loss by the l-cysteine prodrugs, MTCA and PTCA. Exp Eye Res 62 4 (1996) 433-441
11. Wlodek L., and Czubak J. The antioxidative properties of thiazolidine derivatives. Pol J Pharmacol Pharm 41 4 (1989) 369-375
12. Roberts J.C., Charyulu R.L., Zera R.T., and Nagasawa H.T. Protection against acetaminophen hepatotoxicity by ribose-cysteine (RibCys). Pharmacol Toxicol 70 4 (1992) 281-285
13. Roberts J.C., Nagasawa H.T., Zera R.T., Fricke R.F., and Goon D.J. Prodrugs of l-cysteine as protective agents against acetaminophen-induced hepatotoxicity. 2-(polyhydroxy-alkyl)- and 2-(polyacetoxyalkyl)-thiazolidine-4(R)-carboxylic acids. J Med Chem 30 10 (1987) 1891-1896
14. Hsieh C.L., and Yan G.C. Antioxidant actions of du-zhong (Eucommia ulmoides Oliv.) toward oxidative damage in biomolecules. Life Sci 66 15 (2000) 1387-1400
15. Carter P. Spectrophotometric determination of serum iron at the submicrogram level with a new reagent (ferrozine). Anal Biochem 40 2 (1971) 450-458
16. 2+. Prog Biochem Biophys 23 6 (1996) 553-555 [in Chinese]
17. Xie W.H., Yao J.F., and Yuan Q.S. The improvement of assay method for SOD activity by 1,2,3-phentriol self-oxidation. Pharm Ind 19 5 (1988) 217-219 [in Chinese]
18. Halliwell B., Gutteridge J.M., and Aruoma O.I. The deoxyribose method: a simple "test-tube" assay for determination of rate constants for reactions of hydroxyl radicals. Anal Biochem 165 1 (1987) 215-219
19. Duh P.D., Du P.C., and Yen G.C. Action of methanolic extract of mung bean hulls as inhibitors of lipid peroxidation and non-lipid oxidative damage. Food Chem Toxicol 37 11 (1999) 1055-1061
20. Lenz A.G., Costabel U., Shaltiel S., and Levine R.L. Determination of carbonyl groups in oxidatively modified proteins by reduction with tritiated sodium borohydride. Anal Biochem 177 2 (1989) 419-425
21. Sedlak J., and Lindsay R.H. Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman's reagent. Anal Biochem 25 1 (1968) 192-205
22. Lowry O.H., Rosebrough N.J., Farr A.L., and Randall R.J. Protein measurement with the Folin phenol reagent. J Biol Chem 193 1 (1951) 265-275
23. Okuda T., Kimura Y., Yoshida T., Hatano T., Okuda H., and Arichi S. Studies on the activities of tannins and related compounds from medical plants and drugs. I. Inhibitory effect on lipid peroxidation in mitochondria and microsomes of liver. Chem Pharm Bull 31 (1987) 1925-1931
24. Yen G.C., and Duh P.D. Scavenging effect of methanolic extracts of peanut hulls on free-radical and active-oxygen species. J Agric Food Chem 42 (1994) 629-632
25. Mau J.L., Lin H.C., and Chen C.C. Antioxidant properties of several medicinal mushrooms. J Agric Food Chem 50 21 (2002) 6072-6077
26. Gordon M.H., and An J. Antioxidant activity of flavonoids isolated from licrorice. J Agric Food Chem 43 (1995) 1784-1788
27. Tanaka M., Kuei C.W., Nagashima Y., and Taguchi T. Application of antioxidative maillard reaction products from histidine and glucose to sardine products. Nippon Suisan Gakkaishi 54 (1988) 1409-1414
28. Halliwell B., Aeschbach R., Loliger J., and Aruoma O.I. The characterization of antioxidants. Food Chem Toxicol 33 7 (1995) 601-617
29. Emerit J., Beaumont C., and Trivin F. Iron metabolism, free radicals, and oxidative injury. Biomed Pharmacother 55 6 (2001) 333-339
30. Stadtman E.R. Protein oxidation and aging. Science 257 5074 (1992) 1220-1224
31. Mitchell J.R. Acetaminophen toxicity. N Engl J Med 319 24 (1988) 1601-1602
32. Mitchell J.R., Jollow D.J., Potter W.Z., Gillette J.R., and Brodic B.B. Acetaminophen-induced hepatic necrosis. IV Protective role of glutathione. J Pharmacol Exp Ther 187 1 (1973) 211-217
33. Lores Arnaiz S., Llesuy S., Cutrin J.C., and Boveris A. Oxidative stress by acute acetaminophen administration in mouse liver. Free Radic Biol Med 19 3 (1995) 303-310
34. Miesel R., and Zuber M. Copper-dependent antioxidase defenses in inflammatory and autoimmune rheumatic diseases. Inflammation 17 3 (1993) 283-294
35. Halliwell B., and Gutteridge J.M. The antioxidants of human extracellular fluids. Arch Biochem Biophys 280 1 (1990) 1-8
36. Laughton M.J., Halliwell B., Evans P.J., and Hoult J.R.S. Antioxidant and pro-oxidant actions of plant phenolics quercetin, gossypol and myricetin. Effects on lipid peroxidation, hydroxyl radical generation and bleomycin-dependent damage to DNA. Biochem Pharmacol 38 17 (1989) 2859-2865
37. Aruoma O.I., Evans P.J., Kaur H., Sutcliffe L., and Halliwell B. An evaluation of the antioxidant and potential pro-oxidant properties of food additives and trolox C, vitamin E and probucol. Free Radic Res Commun 10 3 (1990) 143-157
38. Aruoma O.I., Halliwell B., Aeschbach R., and Loligers J. Antioxidant and pro-oxidant properties of active rosemary constituents: carnosol and carnosic acid. Xenobiotica 22 2 (1992) 257-268
39. Aruoma O.I., Mureia A., Butler J., and Halliwell B. Evaluation of the antioxidant and pro-oxidant actions of gallic acid and its derivatives. J Agric Food Chem 41 (1993) 1880-1885
40. Zhao M.J., and Jung L. Kinetics of the competitive degradation of deoxyribose and other molecules by hydroxyl radicals produced by the Fenton reaction in the presence of ascorbic acid. Free Radic Res 23 3 (1995) 229-243
41. Smith C., Halliwell B., and Aruoma O.I. Protection by albumin against the pro-oxidant actions of phenolic dietary components. Food Chem Toxicol 30 6 (1992) 483-489
42. Antosiewicz J., Popinigis J., Wozniak M., Damiani E., Carloni P., and Greci L. Effects of indolici and quinolinic aminoxylson protein and lipid peroxidationof rat liver microsomes. Free Radic Biol Med 18 5 (1995) 913-917