189
Views
57
CrossRef citations to date
0
Altmetric
Review Article

The mechanisms for nitration and nitrotyrosine formation in vitro and in vivo: Impact of diet

&
Pages 215-231 | Received 02 Jan 2001, Published online: 07 Jul 2009

References

  • Kikugawa K., Hiramoto K., Tomiyama S., Nakauchi K. Effect of β-carotene on the transformation of tyrosine by nitrogen dioxide and peroxynitrous acid. Free Radical Research 1999; 30: 37–43
  • Pannala A., Razaq R., Halliwell B., Singh S., Rice-Evans C.A. Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: Nitration or electron donation?. Free Radical Biology and Medicine 1998; 24: 594–606
  • Pannala A., Rice-Evans C.A., Halliwell B., Singh S. Inhibition of peroxynitrite-mediated tyrosine nitration by catechin polyphenols. Biochemical and Biophysical Research Communications 1997; 232: 164–168
  • Pfeiffer S., Mayer B. Lack of tyrosine nitration by peroxynitrite generated at physiological pH. The Journal of Biological Chemistry 1998; 273: 27280–27285
  • Whiteman M., Halliwell B. Protection against peroxynitrite-dependent tyrosine nitration and α1-antiproteinase inactivation by ascorbic acid: A comparison with other biological antioxidants. Free Radical Research 1996; 25: 275–283
  • Gow A., Duran D., Thom S.R., Ischiropoulos H. Carbon dioxide enhancement of peroxynitrite-mediated protein tyrosine nitration. Archives of Biochemistry and Biophysics 1996; 333: 42–48
  • Khan J., Brennan D.M., Bradley N., Gao B.R., Bruckdorfer R., Jacobs M. 3-nitrotyrosine in the proteins of human plasma determined by an ELISA method. Biochemical Journal 1998; 330: 795–801
  • Ohshima H., Celan I., Chazotte L., Pignatelli B., Mower H.F. Analysis of 3-nitrotyrosine in biological fluids and protein hydrolyzates by high-performance liquid chromatography using a postseparation, on-line reduction column and electrochemical detection: Results with various nitrating agents. Nitric Oxide-Biology and Chemistry 1999; 3: 132–141
  • Leeuwenburgh C., Hardy M.M., Hazen S.L., Wagner P., Oh-ishi S., Steinbrecher U.P., Heinecke J.W. Reactive nitrogen intermediates promote low density lipoprotein oxidation in human atherosclerotic intima. Journal of Biological Chemistry 1997; 272: 1433–1436
  • Panasenko O.M., Briviba K., Klotz L.-O., Sies H. Oxidative modification and nitration of human low-density lipoproteins by the reaction of hypochlorous acid with nitrite. Archives of Biochemistry and Biophysics 1997; 343: 254–259
  • Ducrocq C., Dendane M., Laprévote O., Serani L., Das B.C., Bouchemeal-Chibani N., Doan B.-T., Gillet B., Karim A., Carayon A., Payen D. Chemical modifications of the vasoconstrictor peptide angiotensin II by nitrogen oxides (NO, HNO2, HOONO) Evaluation by mass spectrometry. European Journal of Biochemistry 1998; 253: 146–153
  • MacMillan-Crow L.A., Thompson J.A. Tyrosine modifications and inactivation of active site manganese superoxide dismutase mutant (Y34F) by peroxynitrite. Archives of Biochemistry and Biophysics 1999; 366: 82–88
  • Yamakura F., Taka H., Fujimura T., Murayama K. Inactivation of human manganese-superoxide dismutase by peroxynitrite is caused by exclusive nitration of tyrosine 34 to 3-nitrotyrosine. The Journal of Biological Chemistry 1998; 273: 14085–14089
  • Sato E., Simpson K.L., Grisham M.B., Koyama S., Robbins R.A. Effects of reactive oxygen and nitrogen metabolites on MCP-1-induced monocyte chemotactic activity in vitro. American Journal of Physiology 1999; 277: L543–L549
  • Rohn T.T., Nelson L.K., Davis A.R., Quinn M.T. Inhibition of GTP binding to Rac2 by peroxynitrite: Potential role for tyrosine modification. Free Radical Biology and Medicine 1999; 26: 1321–1331
  • Guittet O., Ducastel B., Salem J.S., Henry Y., Rubin H., Lemaire G., Lepoivre M. Differential sensitivity of the tyrosyl radical of mouse ribonucleotide reductase to nitric oxide and peroxynitrite. The Journal of Biological Chemistry 1998; 273: 22136–22144
  • Greis K.D., Zhu S., Matalon S. Identification of nitration sites on surfactant protein A by tandem electrospray mass spectrometry. Archives of Biochemistry and Biophysics 1996; 335: 396–402
  • Adam J.M., Ettelaie C., Naseem K.M., James N.J., Bradley N.J., Bruckdorfer K.R. Modification of tissue factor by peroxynitrite influences its procoagulant activity. FEBS Letters 1998; 429: 347–350
  • Knowles M.E., McWeeny D.J., Couchman L., Thorogood M. Interaction of nitrite with proteins at gastric pH. Nature 1974; 247: 288–289
  • Oldreive C., Zhao K., Paganga G., Halliwell B., Rice-Evans C. Inhibition of nitrous acid-dependent tyrosine nitration and DNA base deamination by flavonoids and other phenolic compounds. Chemical Research in Toxicology 1998; 11: 1574–1579
  • Zhu S., Haddad I.Y., Matalon S. Nitration of surfactant protein A (SP-A) tyrosine residues results in decreased mannose binding ability. Archives of Biochemistry and Biophysics 1996; 333: 282–290
  • Van der Vliet A., Eiserich J.P., Halliwell B., Cross C.E. Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. The Journal of Biological Chemistry 1997; 272: 7617–7625
  • Kikugawa K., Kato T., Okamoto Y. Damage of amino acids and proteins induced by nitrogen dioxide, a free radical toxin, in air. Free Radical Biology and Medicine 1994; 16: 373–382
  • Nobbs T.J., Ishii Y., Fujimura T., Saito Y., Niwa M. Chemical modification and site-directed mutagenesis of tyrosine residues in cephalosporin-C acylase from pseudomonas strain-N176. Journal of Fermentation and Bioengineering 1994; 77: 604–609
  • Skawinski W.J., Adebodun F., Cheng J.T., Jordan F., Mendelsohn R. Labeling of tyrosines in proteins with [15N]tetranitromethane, a new NMR reporter for nitrotyrosines. Biochimica et Biophysica Acta 1993; 1162: 297–308
  • Mannick E.E., Bravo L.E., Zarama G., Realpe J.L., Zhang X.-J., Ruiz B., Fontham E.T.H., Mera R., Miller M.J.S., Correa P. Inducible nitric oxide synthase, nitrotyrosine, and apoptosis in Helicobacter pylori gastritis: Effect of antibiotics and antioxidants. Cancer Research 1996; 56: 3238–3243
  • Sadowska-Krowicka H., Mannick E.E., Oliver P.D., Sandoval M., Zhang X.-J., Eloby-Childess S., Clark D.A., Miller M.J.S. Genistein and gut inflammation: Role of nitric oxide. Proceedings of the Society for Experimental Biology and Medicine 1998; 217: 351–357
  • Beckmann J.S., Ye Y.Z., Anderson P.G., Chen J., Accavitti M.A., Tarpey M.M., White C.R., Beckman J.S. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biological Chemistry Hoppe-Seyler 1994; 375: 81–88
  • Buttery L.D.K., Springall D.R., Chester A.H., Evans T.J., Standfield N., Parums D.V., Yacoub M.H., Polak J.M. Inducible nitric oxide synthase is present within human atherosclerotic lesions and promotes the formation and activity of peroxynitrite. Laboratory Investigation 1996; 75: 77–85
  • Cromheeke K.M., Kockx M.M., De Meyer G.R.Y., Bosmans J.M., Bult H., Beelaerts W.J.F., Vrints C.J., Herman A.G. Inducible nitric oxide synthase colocalizes with signs of lipid oxidation/peroxidation in human atherosclerotic plaques. Cardiovascular Research 1999; 43: 744–754
  • Sakaguchi A.A., Miura S., Takeuchi T., Hokari R., Mizumori M., Yoshida H., Higuchi H., Mori M., Kimura H., Suzuki H., Ishii H. Increased expression of inducible nitric oxide synthase and peroxynitrite in Helicobacter pylori gastric ulcer. Free Radical Biology and Medicine 1999; 27: 781–789
  • Ruddell W.S.J., Bone E.S., Hill M.J., Blendis L.M., Walters C.L. Gastric-juice nitrite. A risk factor for cancer in the hypochlorhydric stomach?. Lancet 1976; 2: 1037–1039
  • Kimura H., Hokari R., Miura S., Shigematsu T., Hirokawa M., Akiba Y., Kurose I., Higuchi H., Fujimori H., Tsuzuki Y., Serizawa H., Ishii H. Increased expression of an inducible isoform of nitric oxide synthase and the formation of peroxynitrite in colonic mucosa of patients with active ulcerative colitis. Gut 1998; 42: 180–187
  • Singer I.I., Kawka D.W., Scott S., Weidner J.R., Mumford R.A., Riehl T.E., Stenson W.F. Expression of inducible nitric oxide synthase and nitrotyrosine in colonic epithelium in inflammatory bowel disease. Gastroenterology 1996; 111: 871–885
  • Reimund J.M., Duclos B., Koehl C., Lehr L., Ezenfis J., Baumann R. Nitric oxide end products in patients hospitalized for diarrhoea. European Journal of Gastroenterology and Hepatology 1999; 11: 1013–1018
  • Ter Steege J.C.A., KosterKamphuis L., van Straaten E.A., Forget P.P., Buurman W.A. Nitrotyrosine in plasma of celiac disease patients as detected by a new sandwich ELISA. Free Radical Biology and Medicine 1998; 25: 953–963
  • Ter Steege J., Buurman W., Arends J.W., Forget P. Presence of inducible nitric oxide synthase, nitrotyrosine, CD68, and CD14 in the small intestine in celiac disease. Laboratory Investigation 1997; 77: 29–36
  • Sundqvist T., Laurin P., Falth-Magnusson K., Magnusson K.E., Stenhammar L. Significantly increased levels of nitric oxide products in urine of children with celiac disease. Journal of Pediatric Gastroenterology and Nutrition 1998; 27: 196–198
  • Fukuyama N., Takebayashi Y., Hida M., Ishida H., Ichimori K., Nakazawa H. Clinical evidence of peroxynitrite formation in chronic renal failure patients with septic shock. Free Radical Biology and Medicine 1997; 22: 771–774
  • Good P.F., Werner P., Hsu A., Olanow C.W., Perl D.P. Evidence for neuronal oxidative damage in Alzheimer's disease. American Journal of Pathology 1996; 149: 21–28
  • Hensley K., Maidt M.L., Zhenqiang Y., Sang H., Markesbery W.R., Floyd R.A. Electrochemical analysis of protein nitrotyrosine and dityrosine in the Alzheimer brain indicates region-specific accumulation. The Journal of Neuroscience 1998; 18: 8126–8132
  • Smith M.A., Harris P.L.R., Sayre L.M., Beckman J.S., Perry G. Widespread peroxynitrite-mediated damage in Alzheimer's disease. Journal of Neuroscience 1997; 17: 2653–2657
  • Tohgi H., Abe T., Yamazaki K., Murata T., Isobe C., Ishizaki E. The cerebrospinal fluid oxidized NO metabolites, nitrite and nitrate, in Alzheimer's disease and vascular dementia of Binswanger type and multiple small infarct type. Journal of Neural Transmission 1998; 105: 1283–1291
  • Tohgi H., Abe T., Yamazaki K., Murata T., Ishizaki E., Isobe C. Alterations of 3-nitrotyrosine concentration in the cerebrospinal fluid during aging and in patients with Alzheimer's disease. Neuroscience Letters 1999; 269: 52–54
  • Tohgi H., Abe T., Yamazaki K., Murata T., Ishizaki E., Isobe C. Remarkable increase in cerebrospinal fluid 3-nitrotyrosine in patients with sporadic amyotrophic lateral sclerosis. Annals of Neurology 1999; 46: 129–131
  • Taskiran D., Sagduyu A., Yuceyar N., Kutay F.Z., Pogun S. Increased cerebrospinal fluid and serum nitrite and nitrate levels in amyotrophic lateral sclerosis. International Journal of Neuroscience 2000; 101: 65–72
  • Tohgi H., Abe T., Yamazaki K., Murata T., Ishizaki E., Isobe C. Increase in oxidized NO products and reduction in oxidized glutathione in cerebrospinal fluid from patients with sporadic form of amyotrophic lateral sclerosis. Neuroscience Letters 1999; 260: 204–206
  • Abe K., Pan L.-H., Watanabe M., Kato T., Itoyama Y. Induction of nitrotyrosine-like immunoreactivity in the lower motor neuron of amyotrophic lateral sclerosis. Neuroscience Letters 1995; 199: 152–154
  • Beal M.F., Ferrante R.J., Browne S.E., Matthews R.T., Kowall N.W., Brown R.H. Increased 3-nitrotyrosine in both sporadic and familial amyotrophic lateral sclerosis. Annals of Neurology 1997; 42: 644–654
  • Cross A.H., Manning P.T., Keeling R.M., Schmidt R.E., Misko T.P. Peroxynitrite formation within the central nervous system in active multiple sclerosis. Journal of Neuroimmunology 1998; 88: 45–56
  • Bagasra O., Michaels F.H., Zheng Y.M., Bobroski L.E., Spitsin S.V., Fu Z.F., Tawadros R., Koprowski H. Activation of the inducible form of nitric oxide synthase in the brains of patients with multiple sclerosis. Proceedings of the National Academy of Sciences of the United States of America 1995; 92: 12041–12045
  • Qureshi G.A., Baig S., Bednar I., Sodersten P., Forsberg G., Siden A. Increased cerebrospinal fluid concentration of nitrite in Parkinson's disease. Neuroreport 1995; 21: 1642–1644
  • Barthwal M.K., Srivastava N., Shukla R., Nag D., Seth P.K., Srimal R.C., Dikshit M. Polymorphonuclear leukocyte nitrite content and antioxidant enzymes in Parkinson's disease patients. Acta Neurologica Scandinavica 1999; 100: 300–304
  • Ambs S., Merriam W.G., Bennett W.P., Felley-Bosco E., Ogunfusika M.O., Oser S.M., Klein S., Shields P.G., Billiar T.R., Harris C.C. Frequent nitric oxide synthase-2 expression in human colon adenomas: Implication for tumor angiogenesis and colon cancer progression. Cancer Research 1998; 58: 334–341
  • Kojima M., Morisaki T., Tsukahara Y., Uchiyama A., Matsunari Y., Mibu R., Tanaka M. Nitric oxide synthase expression and nitric oxide production in human colon carcinoma tissue. Journal of Surgical Oncology 1999; 70: 222–229
  • Szaleczky E., Pronai L., Nakazawa H., Tulassay Z. Evidence of in vivo peroxynitrite formation in patients with colorectal carcinoma, higher plasma nitrate/nitrite levels, and lower protection against oxygen free radicals. Journal of Clinical Gastroenterology 2000; 30: 47–51
  • Goto T., Haruma K., Kitadai Y., Ito M., Yoshihara M., Sumii K., Hayakawa N., Kajiyama G. Enhanced expression of inducible nitric oxide synthase and nitrotyrosine in gastric mucosa of gastric cancer patients. Clinical Cancer Research 1999; 5: 1411–1415
  • Eroglu A., Demirci S., Ayyildiz A., Kocaoglu H., Akbulut H., Akgul H., Elhan H.A. Serum concentrations of vascular endothelial growth factor and nitrite as an estimate of in vivo nitric oxide in patients with gastric cancer. British Journal of Cancer 1999; 80: 1630–1634
  • Guadagni S., Walters C.L., Smith P.L.R., Verzaro R., Valenti M., Reed P.I. N-nitroso compounds in the gastric juice of normal controls, patients with partial gastrectomies, and gastric cancer patients. Journal of Surgical Oncology 1996; 63: 226–233
  • Robertson F.M., Long B.W., Tober K.L., Ross M.S., Oberyszyn T.M. Gene expression and cellular sources of inducible nitric oxide synthase during tumor promotion. Carcinogenesis 1996; 17: 2053–2059
  • Evans P., Kaur H., Mitchinson M.J., Halliwell B. Do human atherosclerotic lesions contain nitrotyrosine?. Biochemical and Biophysical Research Communications 1996; 226: 346–351
  • Strong M.J., Sopper M.M., Crow J.P., Strong W.L., Beckman J.S. Nitration of the low molecular weight neurofilament is equivalent in sporadic amyotrophic lateral sclerosis and control cervical spinal cord. Biochemical and Biophysical Research Communications 1998; 248: 157–164
  • Haddad I.Y., Pataki G., Hu P., Galliani C., Beckman J.S., Matalon S. Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. Journal of Clinical Investigation 1994; 94: 2407–2413
  • MacMillan-Crow L.A., Crow J.P., Thompson J.A. Peroxynitrite-mediated inactivation of manganese superoxide dismutase involves nitration and oxidation of critical tyrosine residues. Biochemistry 1998; 37: 1613–1622
  • Viner R.I., Ferrington D.A., Hühmer A.F.R., Bigelow D.J., Schöneich C. Accumulation of nitrotyrosine on the SERCA2a isoform of SR Ca-ATPase of rat skeletal muscle during aging: A peroxynitrite-mediated process?. FEBS Letters 1996; 379: 286–290
  • Zou M.H., Klein T., Pasquet J.P., Ullrich V. Interleukin 1 beta decreases prostacycline synthase activity in rat mesangial cells via endogenous peroxynitrite formation. Biochemical Journal 1998; 336: 507–512
  • Saeki M., Maeda S. p130cas is a cellular target protein for tyrosine nitration induced by peroxynitrite. Neuroscience Research 1999; 33: 325–328
  • Sampson J.B., Ye Y., Rosen H., Beckman J.S. Myeloperoxidase and horseradish peroxidase catalyse tyrosine nitration in proteins from nitrite and hydrogen peroxide. Archives of Biochemistry and Biophysics 1998; 356: 207–213
  • MacMillan-Crow L.A., Crow J.P., Kerby J.D., Beckman J.S., Thompson J.A. Nitration and inactivation of manganese superoxide dismutase in chronic rejection of human renal allografts. Proceedings of the National Academy of Sciences of The United States of America 1996; 93: 11853–11858
  • Moriel P., Abdalla D.S.P. Nitrotyrosine bound to β-VLDL-apoproteins: A biomarker of peroxynitrite formation in experimental atherosclerosis. Biochemical and Biophysical Research Communications 1997; 232: 332–335
  • Boczkowski J., Lisdero C.L., Lanone S., Samb A., Carreras M.C., Boveris A., Aubier M., Poderoso J.J. Endogenous peroxynitrite mediates mitochondrial dysfunction in rat diaphragm during endotoxemia. FASEB Journal 1999; 13: 1637–1646
  • Eiserich J.P., Estévez A.G., Bamberg T.V., Ye Y.Z., Chumley P.H., Beckman J.S., Freeman B.A. Microtubule dysfunction by posttranslational nitrotyrosination of α-tubulin: A nitric oxide-dependent mechanism of cellular injury. Proceedings of the National Academy of Sciences of the United States of American 1999; 96: 6365–6370
  • Gow A.J., Duran D., Malcolm S., Ischiropoulos H. Effects of peroxynitrite-induced protein modifications on tyrosine phosphorylation and degradation. FEBS Letters 1996; 385: 63–66
  • Crow J.P., Ye Y.Z., Strong M., Kirk M., Barnes S., Beckman J.S. Superoxide dismutase catalyzes nitration of tyrosines by peroxynitrite in the rod and head domains of neurofilament-L. Journal of Neurochemistry 1997; 69: 1945–1953
  • Evans T.J., Buttery L.D.K., Carpenter A., Springall D.R., Polak J.M., Cohen J. Cytokine-treated human neutrophils contain inducible nitric oxide synthase that produces nitration of ingested bacteria. Proceedings of the National Academy of Sciences of the United States of America 1996; 93: 9553–9558
  • Virág L., Scott G.S., Cuzzocrea S., Marmer D., Salzman A.L., Szabo C. Peroxynitrite-induced thymocyte apoptosis: the role of caspases and poly (ADP-ribose) synthetase (PARS) activation. Immunology 1998; 94: 345–355
  • Salman-Tabcheh S., Guerin M.-C., Torreilles J. Nitration of tyrosyl-residues from extra- and intracellular proteins in human whole blood. Free Radical Biology and Medicine 1995; 19: 695–698
  • Kuo W.N., Kanadia R.N., Shanbhag V.P. Denitration of peroxynitrite-treated proteins by “protein nitratases” from dog prostate. Biochemistry and Molecular Biology International 1999; 47: 1061–1067
  • Kamisaki Y., Wada K., Bian K., Balabanli B., Davis K., Martin E., Behbod F., Lee Y.-C., Murad F. An activity in rat tissues that modifies nitrotyrosine-containing proteins. Proceedings of the National Academy of Sciences of the United States of America 1998; 95: 11584–11589
  • Greenacre S.A.B., Evans P., Halliwell B., Brain S.D. Formation and loss of nitrated proteins in peroxynitrite-treated rat skin in vivo. Biochemical and Biophysical Research Communications 1999; 262: 781–786
  • Ohshima H., Friesen M., Brouet I., Bartsch H. Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food and Chemical Toxicology 1990; 28: 647–652
  • Kooy N.W., Lewis S.J. The peroxynitrite product 3-nitro-L-tyrosine attenuates the hemodynamic responses to angiotensin II in vivo. European Journal of Pharmacology 1996; 315: 165–170
  • Kooy N.W., Lewis S.J. Nitrotyrosine attenuates the hemodynamic effects of adrenoceptor agonists in vivo: relevance to the pathophysiology of peroxynitrite. European Journal of Pharmacology 1996; 310: 155–161
  • Kamisaki Y., Wada K., Ataka M., Yamada Y., Nakamoto K., Ashida K., Kishimoto Y. Lipopolysaccharide-induced increase in plasma nitrotyrosine concentrations in rats. Biochimica et Biophysica Acta 1997; 1392: 24–28
  • Oldreive C.O. Reactive nitrogen species: the relevance of dietary nitrate and nitrite. University of London. 2000, PhD Thesis
  • World Health Organisation. Nitrates, nitrites and N-nitroso compounds. Environmental Health Criteria, Geneva 1977; 5–5
  • Bartholomew B., Hill M.J. The pharmacology of dietary nitrate and the origin of urinary nitrate. Food and Chemical Toxicology 1984; 22: 789–795
  • Cortas N.K., Wakid N.W. Pharmacokinetic aspects of inorganic nitrate ingestion in man. Pharmacology and Toxicology 1991; 68: 192–195
  • McKnight G.M., Smith L.M., Drummond R.S., Duncan C.W., Golden M., Benjamin N. Chemical synthesis of nitric oxide in the stomach from dietary nitrate in humans. Gut 1997; 40: 211–214
  • Spiegelhalder B., Eisenbrand G., Preussmann R. Influence of dietary nitrate on nitrite content of human saliva: possible relevance to in vivo formation of N-nitroso compounds. Food and Cosmetics Toxicology 1976; 14: 545–548
  • Tannenbaum S.R., Weisman M., Fett D. The effect of nitrate intake on nitrite formation in human saliva. Food and Cosmetics Toxicology 1976; 14: 549–552
  • Wagner D.A., Schultz D.S., Deen W.M., Young V.R., Tannenbaum S.R. Metabolic fate of an oral dose of 15N-labeled nitrate in humans: Effect of diet supplementation with ascorbic acid. Cancer Research 1983; 43: 1921–1925
  • Lee K., Greger J.L., Consaul J.R., Graham K.L., Chinn B.L. Nitrate, nitrite balance, and de novo synthesis of nitrate in humans consuming cured meats. The American Journal of Clinical Nutrition 1986; 44: 188–194
  • Doyle M.P., Herman J.G., Dykstra R.L. Autocatalytic oxidation of haemoglobin induced by nitrite: activation and chemical inhibition. Journal of Free Radicals in Biology and Medicine 1985; 1: 145–153
  • Eiserich J.P., Cross C.E., Jones A.D., Halliwell B., Van der Vliet A. Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorus acid. The Journal of Biological Chemistry 1996; 271: 19199–19208
  • Shibata H., Kono Y., Yamashita S., Sawa Y., Ochiai H., Tanaka K. Degredation of chlorophyll by nitrogen-dioxide generated from nitrite by the peroxidase reaction. Biochimica et Biophysica Acta 1995; 1230: 45–50
  • Hotchkiss J.H. Nitrate, nitrite balance, and de novo synthesis of nitrate. American Journal of Clinical Nutrition 1988; 47: 161–164
  • Chow C.-W., Kapus A., Romanek R., Grinstein S. NO-3-induced pH changes in mammalian cells. Evidence for an NO-3 - H+ cotransporter. Journal of General Physiology 1997; 110: 185–200
  • Furchgott R.F., Zawadzki J.V. The obligatory role of endothelial cells in the relaxation of arterial smooth muscle by acetylcholine. Nature 1980; 288: 373–376
  • Ignarro L.J., Buga G.M., Wood K.S., Byrns R.E., Chaudhuri G. Endothelium-derived relaxing factor produced and released from artery and vein is nitric oxide. Proceedings of the National Academy of Sciences of the United States of America 1987; 84: 9265–9269
  • Palmer R.M.J., Ferrige A.G., Moncada S. Nitric oxide release accounts for the biological activity of endothelium-derived relaxing factor. Nature 1987; 327: 524–526
  • Knowles R.G., Palacios M., Palmer R.M.J., Moncada S. Formation of nitric oxide from L-arginine in the central nervous system: a transduction mechanism for stimulation of the soluble guanylate cyclase. Proceedings of the National Academy of Sciences of The United States of America 1989; 86: 5159–5162
  • Palmer R.M.J., Moncada S. A novel citrulline-forming enzyme implicated in the formation of nitric oxide by vascular endothelial cells. Biochemical and Biophysical Research Communications 1989; 158: 348–352
  • Stuehr D.J., Kwon N.S., Gross S.S., Thiel B.A., Levi R., Nathan C.F. Synthesis of nitrogen oxides from L-arginine by macrophage cytosol: requirement for inducible and constitutive components. Biochemical and Biophysical Research Communications 1989; 161: 420–426
  • Tayeh M.A., Marletta M.A. Macrophage oxidation of L-arginine to nitric oxide, nitrite, and nitrate. Tetrahydrobiopterin is required as a cofactor. The Journal of Biological Chemistry 1989; 264: 19654–19658
  • Springall D.R., Riveros-Moreno V., Buttery L., Suburo A., Bishop A.E., Merrett M., Moncada S., Polak J.M. Immunological detection of nitric oxide synthase(s) in human tissues using heterologous antibodies suggesting different isoforms. Histochemistry 1992; 98: 259–266
  • Nakane M., Schmidt H.H.H.W., Pollock J.S., Forstermann U., Murad F. Cloned human brain nitricoxide synthase is highly expresses in skeletal muscle. FEBS Letters 1993; 316: 175–180
  • Sheng H., Schmidt H.H.H.W., Nakane M., Mitchell J.A., Pollock J.S., Forstermann U., Murad F. Characterization and localization of nitric oxide synthase in non-adrenergic non-cholinergic nerves from bovine retractor penis muscles. British Journal of Pharmacology 1992; 106: 768–773
  • Liu C.Y., Wang C.H., Chen T.C., Lin H.C., Yu C.T., Kuo H.P. Increased level of exhaled nitric oxide and up-regulation of inducible nitric oxide synthase in patients with primary lung cancer. British Journal of Cancer 1998; 78: 534–541
  • Moilanen E., Moilanen T., Knowles R., Charles I., Kadoya Y., al-Saffar N., Revell P.A., Moncada S. Nitric oxide synthase is expressed in human macrophages during foreign body inflammation. American Journal of Pathology 1997; 150: 881–887
  • Reiling N., Ulmer A.J., Muchrow M., Ernst M., Flad H.D., Hauschildt S. Nitric oxide synthase: mRNA expression of different isoforms in human monocytes/macrophages. European Journal of Immunology 1994; 24: 1941–1944
  • Charles I.G., Palmer R.M.J., Hickery M.S., Bayliss M.T., Chubb A.P., Hall V.S., Moss D.W., Moncada S. Cloning, characterization, and expression of a cDNA encoding an inducible nitric oxide synthase from the human chondrocyte. Proceedings of the National Academy of Sciences of the United States of America 1993; 90: 11419–11423
  • Rajnakova A., Goh P.M.Y., Chan S.T.F., Ngoi S.S., Alponat A., Moochhala S. Expression of differential nitric oxide synthase isoforms in human normal gastric mucosa and gastric cancer tissue. Carcinogenesis 1997; 18: 1841–1845
  • Stachura J., Konturek J.W., Karczewska A., Domschke W., Popiela T., Konturek S.J. Helicobacter pylori from duodenal ulcer patients expresses inducible nitric oxide synthase immunoreactivity in vivo and in vitro. Journal of Physiology and Pharmacology 1996; 47: 131–135
  • Zweier J.L., Wang P., Samouilov A., Kuppusamy P. Enzyme-independent formation of nitric oxide in biological tissues. Nature Medicine 1995; 1: 804–809
  • Zweier J.L., Wang P., Samouilov A., Kuppusamy P. Enzymatic/non-enzymatic formation of nitric oxide. Nature Medicine 1995; 1: 1103–1104
  • Furchgott R.F. Studies on endothelium-dependent vasodilation and the endothelium derived relaxing factor. Acta Physiologica Scandinavica 1990; 139: 257–270
  • Moncada S., Palmer R.M.J., Higgs E.A. Biosynthesis of nitric oxide from L-arginine: a pathway for the regulation of cell function and communication. Biochemical Pharmacology 1989; 38: 1709–1715
  • Radomski M., Palmer R.M.J., Moncada S. Comparative pharmacology of endothelium-derived relaxing factor, nitric oxide and prostacyclin in platelets. British Journal of Pharmacology 1987; 92: 181–187
  • Yao S.K., Ober J.C., Krishnaswami A., Ferguson J.J., Anderson H.V., Golino P., Buja L.M., Willerson J.T. Endogenous nitric oxide protects against platelet aggregation and cyclic flow variations in stenosed and endothelium-injured arteries. Circulation 1992; 86: 1302–1309
  • Moro M.A., Russel R.J., Cellek S., Lizasoain I., Su Y., Darley-Usmar V.M., Radomski M.W., Moncada S. cGMP mediates the vascular and platelet actions of nitric oxide: confirmation using an inhibitor of the soluble guanylyl cyclase. Proceedings of the National Academy of Sciences of the United States of America 1996; 93: 1480–1485
  • Bult H., Boeckxstaens G.E., Pelkmans P.A., Jordaens F.H., Van Maercke Y.M., Herman A.G. Nitric oxide as an inhibitory non-adrenergic non-cholinergic neurotransmitter. Nature 1990; 345: 346–347
  • Ignarro L.J., Bush P.A., Buga G.M., Woods K.S., Fukuto J.M., Rajfer J. Nitric oxide and cyclic GMP formation upon electrical field stimulation cause relaxation of corpus cavernosum smooth muscle. Biochemical and Biophysical Research Communications 1990; 170: 843–850
  • Tomita R., Kurosu Y., Munakata K. Relationship between nitric oxide and non-adrenergic non-cholinergic inhibitory nerves in human lower esophageal sphincter. Journal of Gastroenterology 1997; 32: 1–5
  • Moellering D., Mc Andrew J., Patel R.P., Forman H.J., Mulcahy R.T., Jo H., Darley-Usmar V.M. The induction of GSH synthesis by nanomolar concentrations of NO in endothelial cells: a role for gammaglutamylcysteine synthetase and gamma-glutamyl transpeptidase. FEBS Letters 1999; 448: 292–296
  • Hibbs J.B., Taintor R.R., Vavrin Z., Rachlin E.M. Nitric oxide: A cytotoxic activated effector molecule. Biochemical and Biophysical Research Communications 1998; 157: 87–94
  • Stuehr D.J., Nathan C.F. Nitric oxide: A macrophage product responsible for cytostasis and respiratory inhibition in tumour target cells. Journal of Experimental Medicine 1989; 169: 1543–1545
  • Ignarro L.J., Fukuto J.M., Griscavage J.M., Rogers N.E., Byrns R.E. Oxidation of nitric oxide in aqueous solution to nitrite but not nitrate: comparison with enzymatically formed nitric oxide from L-arginine. Proceedings of the National Academy of Sciences of the United States of America 1993; 90: 8103–8107
  • Wink D.A., Darbyshire J.F., Nims R.W., Saavedra J.E., Ford P.C. Reactions of the bioregulatory agent nitric oxide in oxygenated aqueous media: determination of the kinetics for oxidation and nitrosation by intermediates in the NO/O2 reaction. Chemical Research in Toxicology 1993; 6: 23–27
  • Wennmalm Å., Benthin G., Petersson A.-S. Dependence of the metabolism of nitric oxide (NO) in healthy human whole blood on the oxygenation of its red cell haemoglobin. British Journal of Pharmacology 1992; 106: 507–508
  • Radi R. Reactions of nitric oxide with metalloproteins. Chemical Research in Toxicology 1996; 9: 828–835
  • Wagner D.A., Young V.R., Tannenbaum S.R. Mammalian nitrate biosynthesis: incorporation of 15NH3 into nitrate is enhanced by endotoxin treatment. Proceedings of the National Academy of Sciences of the United States of America 1983b; 80: 4518–4521
  • Rhodes P.M., Leone A.M., Francis P.L., Struthers A.D., Moncada S. The L-arginine:nitric oxide pathway is the major source of plasma nitrite in fasted humans. Biochemical and Biophysical Research Communications 1995; 209: 590–596
  • Darley-Usmar V.M., Hogg N., O'Leary V.J., Wilson M.T., Moncada S. The simultaneous generation of superoxide and nitric oxide can initiate lipid peroxidation in human low density lipoprotein. Free Radical Research Communications 1992; 17: 9–20
  • Moore K.P., Darley-Usmar V.M., Morrow J., Roberts L.J., II. Formation of F2-isoprostanes during oxidation of human low-density lipoprotein and plasma by peroxynitrite. Circulation Research 1995; 77: 335–341
  • Huie R.E., Padmaja S. The reaction rate of nitric oxide with superoxide. Free Radical Research Commincations 1993; 18: 195–199
  • Miles A.M., Bohle D.S., Glassbrenner P.A., Hansert B., Wink D.A., Grisham M.B. Modulation of superoxide-dependent oxidation and hydroxylation reactions by nitric oxide. The Journal of Biological Chemistry 1996; 271: 40–47
  • Gross A., Dugas N., Spiesser S., Vouldoukis I., Damais C., Kolb J.P., Dugas B., Dornand J. Nitric oxide production in human macrophagic cells phagocytizing opsonized zymosan: direct characterization by measurement of the luminol dependent chemiluminescence. Free Radical Research 1998; 28: 179–191
  • Ischiropoulos H., Zhu L., Beckman J.S. Peroxynitrite formation from macrophage-derived nitric oxide. Archives of Biochemistry and Biophysics 1992; 298: 446–451
  • Carreras M.C., Pargament G.A., Catz S.D., Poderoso J.J., Boveris A. Kinetics of nitric oxide and hydrogen peroxide production and formation of peroxynitrite during the respiratory burst of human neutrophils. FEBS Letters 1994; 341: 65–68
  • Gagnon C., Leblond F.A., Filep J.G. Peroxynitrite production by human neutrophils, monocytes and lymphocytes challenged with lipopolysaccharide. FEBS Letters 1998; 431: 107–110
  • Deliconstantinos G., Villiotou V., Stavrides J.C. Nitric oxide and peroxynitrite released by ultraviolet B-irradiated human endothelial cells are possibly involved in skin erythema and inflammation. Experimental Physiology 1996; 81: 1021–1033
  • Phelps D.T., Ferro T.J., Higgins P.J., Shankar R., Parker D.M., Johnson A. TNF-alpha induces peroxynitrite-mediated depletion of lung endothelial glutathione via protein kinase C. American Journal of Physiology 1995; 269: L551–L559
  • Lipton S.A., Choi Y.-B., Pan Z.H., Lei S.Z., Chen H.S., Sucher N.J., Loscalzo J., Singel D.J., Stamler J.S. A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds. Nature 1993; 364: 626–632
  • Wink D.A., Hanbauer I., Krishna M.C., DeGraff W., Gamson J., Mitchell J.B. Nitric oxide protects against cellular damage and cytotoxicity from reactive oxygen species. Proceedings of the National Academy of Sciences of the United States of America 1993; 90: 9813–9817
  • Brunelli L., Crow J.P., Beckman J.S. The comparative toxicity of nitric oxide and peroxynitrite to Escherichia coli. Archives of Biochemistry and Biophysics 1995; 316: 327–334
  • Brown A.S., Moro M.A., Masse J.M., Cramer E.M., Radomski M., Darley-Usmar V.M. Nitric oxide-dependent and independent effects on human platelets treated with peroxynitrite. Cardiovascular Research 1998; 40: 380–388
  • Zhu L., Gunn C., Beckman J.S. Bactericidal activity of peroxynitrite. Archives of Biochemistry and Biophysics 1992; 298: 452–457
  • Pryor W.A., Squadrito G.L. The chemistry of peroxynitrite: a product from the reaction of nitric oxide with superoxide. American Journal of Physiology 1995; 268: L699–L722
  • Crow J.P., Spruell C., Chen J., Gunn C., Ischiropoulos H., Tsai M., Smith C.D., Radi R., Koppenol W.H., Beckman J.S. On the pH-dependent yield of hydroxyl radical products from peroxynitrite. Free Radical Biology and Medicine 1994; 16: 331–338
  • Koppenol W.H., Moreno J.J., Pryor W.A., Ischiropoulos H., Beckman J.S. Peroxynitrite: a cloaked oxidant from superoxide and nitric oxide. Chemical Research in Toxicology 1992; 5: 834–842
  • Smil V. Global population and the nitrogen cycle. Scientific American 1997; 277: 58–63
  • Hill M.J., Elliott P., Joossens J.V., Packer P.J., Kesteloot H., Nichols R., Leach S., Dyer A., Stamler R., Stamler J. Twenty-four hour urinary nitrate excretion in 48 populations from 30 countries: An ECPINTERSALT collaborative study. International Journal of Epidemiology 1996; 25: 505–512
  • Joossens J.V., Hill M.J., Elliott P., Stamler R., Stamler J., Lesaffre E., Dyer A., Nichols R., Kesteloot H. Dietary salt, nitrate and stomach cancer mortality in 24 countries. International Journal of Epidemiology 1996; 25: 494–504
  • Ministry of Agriculture, Fisheries and Food (MAFF). 1997 Total diet study — nitrate and nitrite. Food Surveillance Information Sheet 1998; 163
  • Ministry of Agriculture, Fisheries and Food (MAFF). Duplicate diet study of vegetarians — nitrate analyses. Food Surveillance Information Sheet 1998; 165
  • Ministry of Agriculture, Fisheries and Food (MAFF). Nitrate, nitrite and N-nitroso compounds in food: the twentieth report of the Steering group on Food Surveillance, the Working Party on nitrate and Related Compounds in Food. Food Surveillance Paper. HMSO, London 1987; 20–20
  • Hill M.J., Hawksworth G., Tattersall G. Bacteria, nitrosamines and cancer of the stomach. British Journal of Cancer 1973; 28: 562–567
  • Dutt M.C., Lim H.Y., Chew R.K.H. Nitrate consumption and the incidence of gastric cancer in Singapore. Food and Chemical Toxicology 1987; 25: 515–520
  • Van Maanen J.M.S., Welle I.J., Hageman G., Dallinga J.W., Mertens P.L.J.M., Kleinjans J.C.S. Nitrate contamination of drinking water: Relationship with HPRT variant frequency in lymphocyte DNA and urinary excretion of N-nitrosamines. Environmental Health Perspectives 1996; 104: 522–528
  • Greenwood D.J., Hunt J. Effect of nitrogen fertiliser on the nitrate contents of field vegetables grown in Britain. Journal of the Science of Food and Agriculture 1986; 37: 373–383
  • Lin J.-K., Yen J.-Y. Changes in the nitrate and nitrite contents of fresh vegetables during cultivation and post-harvest storage. Food and Cosmetics Toxicology 1980; 18: 597–603
  • Ministry of Agriculture, Fisheries and Food (MAFF). 1996/97 UK monitoring programme for nitrate in lettuce and spinach. Food Surveillance Information Sheet 1997; 121
  • Walters A.H., Fletcher J.R., Law S.J. Nitrate in vegetables: Estimation by HPLC. Nutrition and Health 1986; 4: 141–149
  • Lyons D.J., McCallum L.E., Osborne W.J., Nobbs P.E. Assessment of procedures for the determination of nitrate and nitrite in vegetable extracts. Analyst 1991; 116: 153–157
  • Huarte-Mendicoa J.C., Astiasaran I., Bello J. Nitrate and nitrite levels in fresh and frozen broccoli. Effect of freezing and cooking. Food Chemistry 1997; 58: 39–42
  • London Food Commission. Fertilisers: Flooding the market. Food Adulteration and how to Beat it. Unwin Hyman Limited, London 1988; 110–156
  • Comly H.H. Cyanosis in infants caused by nitrates in well water. Journal of the American Medical Association 1945; 129: 112–116
  • Donahoe W.E. Cyanosis in infants with nitrates in drinking water as cause. Paediatrics 1949; 3: 308–311
  • Dorsch M.M., Scragg R.K.R., McMichael A.J., Baghurst P.A., Dyer K.F. Congenital malformations and maternal drinking water supply in rural South Auatralia: A case-control study. American Journal of Epidemiology 1984; 119: 473–486
  • Baskin S.I., Horowitz A.M., Nealley E.W. The antidotal action of sodium nitrite and sodium thiosulfate against cyanide poisoning. Journal of Clinical Pharmacology 1992; 32: 368–375
  • Forman D., Al-Dabbagh S., Doll R. Nitrate, nitrites and gastric cancer in Great Britain. Nature 1985; 313: 620–625
  • Correa P., Haenszel W., Cuello C., Tannenbaum S., Archer M. A model for gastric cancer epidemiology. Lancet 1975; 2: 58–60
  • Correa P. A human model for gastric carcinogenesis. Cancer Research 1988; 48: 3554–3560
  • Ward M.H., Mark S.D., Cantor K.P., Weisenburger D.D., Correa-Villasenor A., Zahm S.H. Drinking water nitrate and the risk of non-Hodgkin's lymphoma. Epidemiology 1996; 7: 465–471
  • Virtanen S.M., Jaakkola L., Rasanen L., Ylonen K., Aro A., Lounamaa R., Akerblom H.K., Tuomilehto J. Nitrate and nitrite intake and the risk for type 1 diabetes in Finnish children. Childhood Diabetes in Finland Study Group. Diabetic Medicine 1994; 11: 656–662
  • Lee M., Wrensch M., Miike R. Dietary and tobacco risk factors for adult onset glioma in the San Francisco Bay Area. Cancer Causes and Control 1997; 8: 13–24
  • Lohsoonthorn P., Danvivat D. Colorectal cancer risk factors: a case-control study in Bangkok. Asia-Pacific Journal of Public Health 1995; 8: 118–122
  • Kaudewitz F. Production of bacterial mutants with nitrous acid. Nature 1959; 183: 1829–1830
  • Verly W.G., Barbason H., Dusart J., Petitpas-Dewandre A. A comparative study of the action of ethyl methane sulphonate and HNO2 on the mutation to streptomycin resistance of Escherchia coli K 12. Biochimica et Biophysica Acta 1967; 145: 752–762
  • De Serres F.J., Brockman H.E., Barnett W.E., Kølmark H.G. Allelic complementation among nitrous acid-induced ad-3B mutants of Neurospora crassa. Mutation Research 1967; 4: 415–424
  • Zimmerman T.F.K., Schwaier R. Induction of a mitotic gene conversion with nitrous acid, 1-methyl-3-nitro-1-nitrosoguanidine and other alkylating agents in Saccharomyces cerevisiae. Molecular and General Genetics 1967; 100: 63–76
  • Shuval H.I., Gruener N. Epidemiological and toxicological aspects of nitrates and nitrites in the environment. American Journal of Public Health 1972; 62: 1045–1052
  • Clapp N.K., Toya R.E. Effect of cumulative dose and dose rate on dimethylnitrosamine oncogenesis in RF mice. Journal of the National Cancer Institute 1970; 45: 495–498
  • Mohr U., Hilfrich J. Brief communication: Effect of a single dose of N-diethylnitrosamine on the rat kidney. Journal of the National Cancer Institute 1972; 49: 1729–1731
  • Montesanto R., Saffiotti U. Carcinogenic response of the respiratory tract of Syrian golden hamsters to different doses of diethylnitrosamine. Cancer Research 1968; 28: 2197–2210
  • Terracini B., Magee P.N., Barnes J.M. Hepatic pathology in rats on low dietary levels of dimethylnitrosamine. British Journal of Cancer 1967; 21: 559–565
  • Vesselinovitch S.D. The sex-dependent difference in the development of liver tumours in mice administered dimethylnitrosamine. Cancer Research 1969; 29: 1024–1027
  • Benjamin N., O'Driscoll F., Dougall H., Duncan C., Smith L., Golden M., McKenzie H. Stomach NO synthesis. Nature 1994; 368: 502–502
  • Dykhuizen R.S., Frazer R., Duncan C., Smith C.C., Golden M., Benjamin N., Leifert C. Antimicrobial effect of acidified nitrite on gut pathogens: importance of dietary nitrate in host defence. Antimicrobial Agents and Chemotherapy 1996; 40: 1422–1425
  • Challis B.C., Kyrtopoulos S.A. The chemistry of nitroscompounds. Part II. Nitrosation of amines by the two phase interaction of amines in solution with gaseous oxides of nitrogen. Journal of the Chemical Society Perkin I 1979; 2: 299–304
  • Kono Y., Shibata H., Kodama Y., Sawa Y. The suppression of the N-nitrosating reaction by chlorogenic acid. Biochemical Journal 1995; 312: 947–953
  • Mirvish S.S. Chemical Research in Toxicology 1975; 1: 249–257
  • Mirvish S.S. Formation of N-nitroso compounds: chemistry, kinetics, and in vivo occurrence. Toxicology and Applied Pharmacology 1975; 31: 325–351
  • Fan T.-Y., Tannenbaum S.R. Factors influencing the rate of formation of nitrosomorpholine from morpholine and nitrite: acceleration by thiocyanate and other anions. Journal of Agricultural and Food Chemistry 1973; 21: 237–240
  • Myshkin A.E., Konyaeva V.S., Gumargalieva K.Z., Moiseev Y.V. Oxidation of ascorbic acid in the presence of nitrites. Journal of Agricultural Food Chemistry 1996; 44: 2948–2950
  • Weisburger J.H., Marquardt H., Hirota N., Mori H., Williams G.M. Induction of cancer of the glandular stomach in rats by an extract of nitrite-treated fish. Journal of the National Cancer Institute 1980; 64: 163–166
  • Bonnett R., Holleyhead R. Reaction of tryptophan derivatives with nitrite. Journal of the Chemical Society, Perkin Transactions 1974; 1: 962–964
  • Bonnett R., Nicolaidou P. Nitrite and the environment. The nitrosation of alpha-amino acid derivatives. Heterocycles 1977; 7: 637–659
  • Stillwell W.G., Glogowski J., Xu H.X., Wishnok J.S., Zavala D., Montes G., Correa P., Tannenbaum S.R. Urinary-excretion of nitrate, n-nitrosoproline, 3-methyladenine, and 7-methylguanine in a colombian population at high-risk for stomach-cancer. Cancer Research 1991; 51: 190–194
  • Tricker A.R., Preussmann R. Influence of cysteine and nitrate on the endogenous formation of N-nitroamino acids. Cancer Letters 1987; 34: 39–47
  • Boyland E., Walker S.A. Effect of thiocyanate on nitrosation of amines. Nature 1974; 248: 601–602
  • Sen N.P., Smith D.C., Schwinghamer L., Marleau J.J. Diethylnitrosamine and other N-nitrosamines in foods. Journal of the Association of Official Analytical Chemists 1969; 52: 47–52
  • Sen N.P., Smith D.C., Schwinghamer L. Formation of N-nitrosamines from secondary amines and nitrite in human and animal gastric juice. Food and Cosmetics Toxicology 1969; 7: 301–307
  • Hawksworth G.M., Hill M.J. Bacteria and the N-nitrosation of secondary amines. British Journal of Cancer 1971; 25: 520–526
  • Miwa M., Stuehr D.J., Marletta M.A., Wishnok J.S., Tannenbaum S.R. Nitrosation of amines by stimulated macrophages. Carcinogenesis 1987; 8: 955–958
  • Kuenzig W., Chau J., Norkius E., Holowaschenko H., Newmark H., Mergens W., Conney A.H. Caffeic and ferulic acid as blockers of nitrosamine formation. Carcinogenesis 1984; 5: 309–313
  • Vermeer I.T.M., Moonen E.J.C., Dallinga J.W., Kleinjans J.C.S., van Maanen J.M.S. Effect of ascorbic acid and green tea on endogenous formation of N-nitrosodimethylamine and N-nitrosopiperidine in humans. Mutation Research 1999; 428: 353–361
  • McWeeny D.J. Reactions of some food additives during storage. Food Chemistry 1982; 9: 89–101
  • Challis B.C., Bartlett C.D. Possible cocarcinogenic effects of coffee constituents. Nature 1975; 254: 532–533
  • Walker E.A., Pignatelli B., Castegnaro M. Effects of gallic acid on nitrosamine formation. Nature 1975; 258: 176–176
  • Rueff J., Gaspar J., Laires A. Structural requirements for mutagenicity of flavonoids upon nitrosation. A structure-activity study. Mutagenesis 1995; 10: 325–328

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.