S-allylcysteine scavenges singlet oxygen and hypochlorous acid and protects LLC-PK1 cells of potassium dichromate-induced toxicity

Food and Chemical Toxicology

Volumn 45, Issue 10, 2007, Pages 2030-2039

  Medina Campos, Omar Noel ^a   Barrera, Diana ^b   Segoviano Murillo, Sabina ^a   Rocha, Diana ^a   Maldonado, Perla D ^c   Mendoza Patiño, Nicandro ^b   Pedraza Chaverri, José ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^c NATIONAL INSTITUTE OF NEUROLOGY AND NEUROSURGERY   (Mexico)

Author keywords

Hypochlorous acid; K2Cr2O7; Oxidative stress; Peroxynitrite; S allylcysteine; Scavenging activity; Singlet oxygen

Indexed keywords

ACETYLCYSTEINE; DICHROMATE POTASSIUM; DIMETHYLUREA; GLUTATHIONE; HYDROGEN PEROXIDE; HYDROXIDE; HYPOCHLOROUS ACID; OXYGEN RADICAL; PENICILLAMINE; PYRUVATE SODIUM; S ALLYLCYSTEINE; SCAVENGER; SINGLET OXYGEN; THIOCTIC ACID;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL PROTECTION; COMPARATIVE STUDY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFECT; DRUG MECHANISM; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; KIDNEY CELL; NEPHROTOXICITY; OXIDATIVE STRESS;

ANIMALS; CELL SURVIVAL; CYSTEINE; FREE RADICAL SCAVENGERS; HYDROGEN PEROXIDE; HYDROXYL RADICAL; HYPOCHLOROUS ACID; LLC-PK1 CELLS; POTASSIUM DICHROMATE; PYRUVIC ACID; REACTIVE OXYGEN SPECIES; SUPEROXIDES; SWINE; THIOCTIC ACID; THIOUREA;

ALLIUM SATIVUM;

EID: 34547842123     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2007.05.002     Document Type: Article

References (82)

1. Aiyar J., Berkovits H.J., Floyd R.A., and Wetterhahn K.E. Reaction of chromium (VI) with glutathione or with hydrogen peroxide: identification of reactive intermediates and their role in chromium (VI)-induced DNA damage. Environ. Health Perspect. 92 (1991) 53-62
2. Appenroth D., and Winnefeld K. Vitamin E and C in the prevention of metal nephrotoxicity in developing rats. Exp. Toxicol. Pathol. 50 (1998) 391-396
3. Bagchi D., Stohs S., Downs B., Bagchi M., and Preuss H.G. Cytotoxicity and oxidative mechanisms of different forms of chromium. Toxicology 180 (2002) 5-22
4. 7. Free Radic. Biol. Med. 34 (2003) 1390-1398
5. 7-induced nephrotoxicity in rats: the indispensability of HO-1 preinduction and lack of association with some antioxidant enzymes. Life Sci. 73 (2003) 3027-3041
6. Barthomeuf C.M., Debiton E., Barbakadze V.V., and Kemertelidze E.P. Evaluation of the dietetic and therapeutic potential of a high molecular weight hydroxycinnamate-derived polymer from Symphytum asperum Lepech. Regarding its antioxidant, antilipoperoxidant, antiinflammatory, and cytotoxic properties. J. Agric. Food Chem. 49 (2001) 3942-3946
7. Beckman J.S., Chen H., Ischiropulos H., and Crow J.P. Oxidative chemistry of peroxynitrite. Meth. Enzymol. 233 (1994) 229-240
8. Belloir C., Singh V., Daurat C., Siess M.H., and Le Bon A.M. Protective effects of garlic sulfur compounds against DNA damage induced by direct- and indirect-acting genotoxic agents in HepG2 cells. Food Chem. Toxicol. 44 (2006) 827-834
9. Chakraborty N., and Tripathy B.C. Involvement of singlet oxygen in 5-aminolevulinic acid-induced photodynamic damage of cucumber (Cucumbis sativus L.) chloroplasts. Plant Physiol. 98 (1992) 7-11
10. Cheng F.C., Jen J.F., and Tsai T.H. Hydroxyl radical in living systems and its separation methods. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 781 (2002) 481-496
11. Ching T.L., Jong J., and Bast A. A method for screening hypochlorous-acid scavengers by inhibition of the oxidation of 5-thio-2-nitrobenzoic acid: application to anti-asthmatic drugs. Anal. Biochem. 218 (1994) 377-381
12. Chung L.Y. The antioxidant properties of garlic compounds: allyl cysteine, alliin, allicin, and allyl disulfide. J. Med. Food 9 (2006) 205-213
13. Conforti F., Statti G., Uzunov D., and Menichini F. Comparative chemical composition and antioxidant activities of wild and cultivated Laurus nobilis L. leaves and Foeniculum vulgare subsp. piperitum (Ucria) coutinho seeds. Biol. Pharm. Bull 29 (2006) 2056-2064
14. Denicola A., and Radi R. Peroxynitrite and drug-dependent toxicity. Toxicology 208 (2005) 273-288
15. Fernandes E., Toste S.A., Lima J.L.F.C., and Reis S. The metabolism of sulindac enhances its scavenging activity against reactive and nitrogen species. Free Radic. Biol. Med. 35 (2003) 1008-1017
16. Flick D.A., and Gifford G.E. Comparison of in vitro cell cytotoxic assays for tumor necrosis factor. J. Immunol. Methods 68 (1984) 167-175
17. Floriano-Sánchez E., Villanueva C., Medina-Campos O.N., Rocha D., Sánchez-González D.J., Cárdenas-Rodri{dotless}́guez N., and Pedraza-Chaverri{dotless}́ J. Nordihydroguaiaretic acid is a potent in vitro scavenger of peroxynitrite, singlet oxygen, hydroxyl radical, superoxide anion, and hypochlorous acid and prevents in vivo tyrosine nitration in lung. Free Radic. Res. 40 (2006) 523-533
18. Geng Z., Rong Y., and Lau B.H. S-allyl cysteine inhibits activation of nuclear factor kappa B in human T cells. Free Radic. Biol. Med. 23 (1997) 345-350
19. Herrera-Mundo M.N., Silva-Adaya D., Maldonado P.D., Galvan-Arzate S., Andres-Martinez L., Perez-de la Cruz V., Pedraza-Chaverri J., and Santamaria A. S-Allylcysteine prevents the rat from 3-nitropropionic acid-induced hyperactivity, early markers of oxidative stress and mitochondrial dysfunction. Neurosci. Res. 56 (2006) 39-44
20. Higuchi O., Tateshita K., and Nishimura H. Antioxidative activity of sulfur-containing compounds in Allium species for human low-density lipoprotein (LDL) oxidation in vitro. J. Agric. Food Chem. 51 (2003) 7208-7214
21. Ho S.E., Ide N., and Lau B.H. S-allyl cysteine reduces oxidant load in cells involved in the atherogenic process. Phytomedicine 8 (2001) 39-46
22. Hojo Y., and Satomi Y. In vitro nephrotoxicity induced in mice by chromium (VI): involvement of glutathione and chromium (V). Biol. Trace Elem. Res. 31 (1991) 21-31
23. Hsu C.C., Huang C.N., Hung Y.C., and Yin M.C. Five cysteine-containing compounds have antioxidative activity in Balb/cA mice. J. Nutr. 134 (2004) 149-152
24. Hsu C.C., Lin C.C., Liao T.S., and Yin M.C. Protective effect of S-allyl cysteine and s-propyl cysteine on acetaminophen-induced hepatotoxicity in mice. Food Chem. Toxicol. 44 (2006) 393-397
25. Huang C.N., Horng J.S., and Yin M.C. Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma. J. Agric. Food Chem. 52 (2004) 3674-3678
26. Ide N., and Lau B.H. Garlic compounds protect vascular endothelial cells from oxidized low density lipoprotein-induced injury. J. Pharm. Pharmacol. 49 (1997) 908-911
27. Ide N., and Lau B.H. S-allylcysteine attenuates oxidative stress in endothelial cells. Drug Dev. Ind. Pharm. 25 (1999) 619-624
28. Ide N., and Lau B.H. Garlic compounds minimize intracellular oxidative stress and inhibit nuclear factor-kappa b activation. J. Nutr. 131 (2001) 1020S-1026S
29. (2+)-induced oxidative modification of low density lipoprotein. Planta Med. 63 (1997) 263-264
30. Imai J., Ide N., Nagae S., Moriguchi T., Matsuura H., and Itakura Y. Antioxidant and radical scavenging effects of aged garlic extract and its constituents. Planta Med. 60 (1994) 417-420
31. Ippoushi K., Itou H., Azuma K., and Higashio H. Effect of naturally occurring organosulfur compounds on nitric oxide production in lipopolysaccharide-activated macrophages. Life Sci. 71 (2002) 411-419
32. Ito Y., Ito M., Takagi N., Saito H., and Ishige K. Neurotoxicity induced by amyloid beta-peptide and ibotenic acid in organotypic hippocampal cultures: protection by S-allyl-l-cysteine, a garlic compound. Brain Res. 985 (2003) 98-107
33. Ito Y., Kosuge Y., Sakikubo T., Horie K., Ishikawa N., Obokata N., Yokoyama E., Yamashina K., Yamamoto M., Saito H., Arakawa M., and Ishige K. Protective effect of S-allyl-l-cysteine, a garlic compound, on amyloid beta-protein-induced cell death in nerve growth factor-differentiated PC12 cells. Neurosci. Res. 46 (2003) 119-125
34. Kim K.M., Chun S.B., Koo M.S., Choi W.J., Kim T.W., Kwon Y.G., Chung H.T., Billiar T.R., and Kim Y.M. Differential regulation of NO availability from macrophages and endothelial cells by the garlic component S-allyl cysteine. Free Radic. Biol. Med. 30 (2001) 747-756
35. Kim J.M., Chang H.J., Kim W.K., Chang N., and Chun H.S. Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds. J. Agric. Food Chem. 54 (2006) 6547-6553
36. Kim J.M., Lee J.C., Chang N., Chun H.S., and Kim W.K. S-Allyl-l-cysteine attenuates cerebral ischemic injury by scavenging peroxynitrite and inhibiting the activity of extracellular signal-regulated kinase. Free Radic. Res. 40 (2006) 827-835
37. Kocha T., Yamaguchi M., Ohtaki H., Fukuda T., and Aoyagi T. Hydrogen peroxide-mediated degradation of protein: different oxidation modes of copper- and iron-dependent hydroxyl radicals on the degradation of albumin. Biochim. Biophys. Acta 1337 (1997) 319-326
38. Kodera Y., Suzuki A., Imada O., Kasuga S., Sumioka I., Kanezawa A., Taru N., Fujikawa M., Nagae S., Masamoto K., Maeshige K., and Ono K. Physical, chemical, and biological properties of S-allylcysteine, an amino acid derived from garlic. J. Agric. Food Chem. 50 (2002) 622-632
39. Kooy N.W., Royall J.A., Ischiropoulos H., and Beckman J.S. Peroxynitrite-mediated oxidation of dihydrorhodamine 123. Free Radic. Biol. Med. 16 (1994) 149-156
40. Kosuge Y., Koen Y., Ishige K., Minami K., Urasawa H., Saito H., and Ito Y. S-allyl-l-cysteine selectively protects cultured rat hippocampal neurons from amyloid beta-protein- and tunicamycin-induced neuronal death. Neuroscience 122 (2003) 885-895
41. Lawson L.D. The composition and chemistry of garlic cloves and processed garlic. In: Koch H.P., and Lawson L.D. (Eds). Garlic: The Science and Therapeutic Application of Allium sativum L. and Related Species (1996), Williams & Wilkins, Baltimore 37-107
42. Lawson L.D., Wang Z.J., and Hughes B.G. γ-Glutamyl-S-alkylcysteines in garlic and other Allium spp.: precursors of AGE dependent trans-1-propenyl. J. Nat. Prod 54 (1991) 436-444
43. Lass A., Suessenbacher A., Wolkart G., Mayer B., and Brunner F. Functional and analytical evidence for scavenging of oxygen radicals by l-Arginine. Mol. Pharmacol. 61 (2002) 1081-1088
44. Liu K., and Shi X. In vivo reduction of chromium (VI) and its related free radical generation. Mol. Cell. Biochem. 222 (2001) 41-47
45. Liu K.J., Shi X., and Dalal N.S. Synthesis of Cr(VI)-GSH, its identification and its free hydroxyl radical generation: a model compound for Cr(VI) carcinogenicity. Biochem. Biophys. Res. Commun. 235 (1997) 54-58
46. Long L.H., Evans P.J., and Halliwell B. Hydrogen peroxide in human urine: implications for antioxidant defense and redox regulation. Biochem. Biophys. Res. Commun. 262 (1999) 605-609
47. Maldonado P.D., Barrera D., Rivero I., Mata R., Medina-Campos O.N., Hernandez-Pando R., and Pedraza-Chaverri J. Antioxidant S-allylcysteine prevents gentamicin-induced oxidative stress and renal damage. Free Radic. Biol. Med. 35 (2003) 317-324
48. 4-induced oxidative stress and pulmonary fibrosis in rats. Biofactors 26 (2006) 81-92
49. Morgan P.E., Dean R.T., and Davies M.J. Protective mechanisms against peptide and protein peroxides generated by singlet oxygen. Free Radic. Biol. Med. 36 (2004) 484-496
50. Morihara N., Ide N., Sumioka I., and Kyo E. Aged garlic extract inhibits peroxynitrite-induced hemolysis. Redox Rep. 10 (2005) 159-165
51. Mostafa M.G., Mima T., Ohnishi S.T., and Mori K. S-allylcysteine ameliorates doxorubicin toxicity in the heart and liver in mice. Planta Med. 66 (2000) 148-151
52. Na K.J., Jeong S.Y., and Lim C.H. The role of glutathione in the acute nephrotoxicity of sodium dichromate. Arch. Toxicol. 66 (1992) 646-651
53. Nagae S., Ushijima M., Hatono S., Imai J., Kasuga S., Matsuura H., Itakura Y., and Higashi Y. Pharmacokinetics of the garlic compound S-allylcysteine. Planta Med. 60 (1994) 214-217
54. Nishimura H., Higuchi O., and Tateshita K. Antioxidative activity of sulfur-containing compounds in Allium species for human LDL oxidation in vitro. Biofactors 21 (2004) 277-280
55. Nishimura H., Higuchi O., Tateshita K., Tomote K., Okuma Y., and Nomura Y. Antioxidative activity and ameliorative effects of memory impairment of sulfur-containing compounds in Allium species. Biofactors 26 (2006) 135-146
56. Nishiyama N., Moriguchi T., Morihara N., and Saito H. Ameliorative effect of S-allylcysteine, a major thioallyl constituent in aged garlic extract, on learning deficits in senescence-accelerated mice. J. Nutr. 131 (2001) 1093S-1095S
57. Noguchi N., Nakada A., Itoh Y., Watanabe A., and Niki E. Formation of active oxygen species and lipid peroxidation induced by hypochlorite. Arch. Biochem. Biophys. 397 (2002) 440-447
58. Numagami Y., and Ohnishi S.T. S-allylcysteine inhibits free radical production, lipid peroxidation and neuronal damage in rat brain ischemia. J. Nutr. 131 (2001) 1100S-11055S
59. Numagami Y., Sato S., and Ohnishi S.T. Attenuation of rat ischemic brain damage by aged garlic extracts: a possible protecting mechanism as antioxidants. Neurochem. Int. 29 (1996) 135-143
60. O'Brien P., and Kortenkamp A. Chemical models important in understanding the ways in which chromate can damage DNA. Environ. Health Perspect. 102 (1994) 3-10
61. Pedraza-Chaverri{dotless}́ J., Barrera D., Maldonado P.D., Chirino Y.I., Maci{dotless}́as-Ruvalcaba N.A., Medina-Campos O.N., Castro L., Salcedo M.I., and Hernández-Pando R. S-allylmercaptocysteine scavenges hydroxyl radical and singlet oxygen in vitro and attenuates gentamicin-induced oxidative and nitrosative stress and renal damage in vivo. BMC Clin. Pharmacol. 4 (2004) 5
62. 7-induced nephrotoxicity. BMC Nephrol. 6 (2005) 4
63. Pedraza-Chaverri{dotless}́ J., Medina-Campos O.N., Ávila-Lombardo R., Zúñiga-Bustos A.B., and Orozco-Ibarra M. Reactive oxygen species scavenging capacity of different cooked garlic preparations. Life Sci. 78 (2006) 761-770
64. Pedraza-Chaverri{dotless}́ J., Medina-Campos O.N., and Segoviano-Murillo S. Effect of heating on peroxynitrite scavenging capacity of garlic. Food Chem. Toxicol. 45 (2007) 622-627
65. Pedraza-Chaverri J., Moreno-Muniz S.I., Cruz C., Hernandez-Pando R., Larriva-Sahd J., and Tapia E. Urinary angiotensin I-converting enzyme activity is increased in experimental acute renal failure. Clin. Invest. Med. 18 (1995) 424-434
66. Peng Q., Buz'Zard A.R., and Lau B.H. Neuroprotective effect of garlic compounds in amyloid-beta peptide-induced apoptosis in vitro. Med. Sci. Monit. 8 (2002) BR328-BR337
67. Perez-de la Cruz V., Gonzalez-Cortes C., Pedraza-Chaverri J., Maldonado P.D., Andres-Martinez L., and Santamaria A. Protective effect of S-allylcysteine on 3-nitropropionic acid-induced lipid peroxidation and mitochondrial dysfunction in rat brain synaptosomes. Brain Res. Bull. 68 (2006) 379-383
68. Perez-Severiano F., Rodriguez-Perez M., Pedraza-Chaverri J., Maldonado P.D., Medina-Campos O.N., Ortiz-Plata A., Sanchez-Garcia A., Villeda-Hernandez J., Galvan-Arzate S., Aguilera P., and Santamaria A. S-Allylcysteine, a garlic-derived antioxidant, ameliorates quinolinic acid-induced neurotoxicity and oxidative damage in rats. Neurochem. Int. 45 (2004) 1175-1183
69. Perez-Severiano F., Salvatierra-Sanchez R., Rodriguez-Perez M., Cuevas-Martinez E.Y., Guevara J., Limon D., Maldonado P.D., Medina-Campos O.N., Pedraza-Chaverri J., and Santamaria A. S-Allylcysteine prevents amyloid-beta peptide-induced oxidative stress in rat hippocampus and ameliorates learning deficits. Eur. J. Pharmacol. 489 (2004) 197-202
70. Puttaraju N.G., Venkateshaiah S.U., Dharmesh S.M., Urs S.M., and Somasundaram R. Antioxidant activity of indigenous edible mushrooms. J. Agric. Food Chem. 54 (2006) 9764-9772
71. Sengupta T., Chattopadhyay D., Ghosh N., Maulik G., and Chatterjee G.C. Impact of chromium on lipoperoxidative processes and subsequent operation of the glutathione cycle in rat renal system. Indian J. Biochem. Biophys. 29 (1992) 287-290
72. Shi X., and Dalal N.S. Generation of hydroxyl radical by chromate in biologically relevant systems: role of Cr(VI) complex versus tetraperochromate(V). Environ. Health Perspect. 102 (1994) 231-236
73. {radical dot}OH radicals in the reduction of Cr(VI) in cellular media. Arch. Biochem. Biophys. 281 (1990) 90-95
74. Standeven A.M., and Wetterhahn K.E. Possible role of glutathione in chromium(VI) metabolism and toxicity in rats. Pharmacol. Toxicol. 68 (1991) 469-476
75. Stohs S.J., and Bagchi D. Oxidative mechanisms in the toxicity of metal ions. Free Radic. Biol. Med. 18 (1995) 321-336
76. Stohs S.J., Bagchi D., Hassoun E., and Bagchi M. Oxidative mechanisms in the toxicity of chromium and cadmium ions. J. Environ. Pathol. Toxicol. Oncol. 19 (2000) 201-213
77. Sugiyama M. Role of physiological antioxidants in chromium(VI)-induced cellular injury. Free Radic. Biol. Med. 12 (1992) 397-407
78. Szabo C. Multiple pathways of peroxynitrite cytotoxicity. Toxicol. Lett. 140/141 (2003) 105-112
79. Tsou T.C., Chen C.L., Liu T.Y., and Yang J.L. Induction of 8-hydroxycleoxyguanosine in DNA by chromium (III) plus hydrogen peroxide and its prevention by scavengers. Carcinogenesis 17 (1996) 103-108
80. Winterbourn C.C., and Kettle A.J. Radical-radical reactions of superoxide: a potential route to toxicity. Biochem. Biophys. Res. Commun. 305 (2003) 729-736
81. Yamasaki T., Li L., and Lau B.H. Garlic compounds protect vascular endothelial cells from hydrogen peroxide-induced oxidant injury. Phyother. Res. 8 (1994) 408-412
82. Yu H., Liu X., Xing R., Liu S., Li C., and Li P. Radical scavenging activity of protein from tentacles of jellyfish Rhopilema esculentum. Bioorg. Med. Chem. Lett 15 (2005) 2659-2664