Comparative effects of mono-, di-, tri-, and tetrasulfides derived from plants of the Allium family: redox cycling in vitro and hemolytic activity and Phase 2 enzyme induction in vivo

Fenwick, 1985, The genus Allium, CRC Crit. Rev. Food Sci. Nutr, 22, 199, 10.1080/10408398509527415

Block, 1992, The organosulfur chemistry of the genus Allium, Angew. Chem. Int. Ed. Eng, 31, 1135, 10.1002/anie.199211351

Lawson, 1998, Garlic, ACS Symp. Ser, 691, 176, 10.1021/bk-1998-0691.ch014

Block, 1998, Garlic as a functional food, ACS Symp. Ser, 702, 125, 10.1021/bk-1998-0702.ch013

Earl, 1982, Dimethyl disulphide in the blood of cattle fed on brassicas, J. Sci. Food Agric, 34, 23, 10.1002/jsfa.2740340105

Taucher, 1996, Analysis of compounds in human breath after ingestion of garlic using proton-transfer-reaction mass spectrometry, J. Agric. Food Chem, 44, 3778, 10.1021/jf960640e

Egen-Schwind, 1992, Metabolism of garlic constituents in the isolated perfused rat liver, Planta Med, 58, 301, 10.1055/s-2006-961471

Suarez, 1999, Differentiation of mouth versus gut as site of origin of odoriferous breath gases after garlic ingestion, Am. J. Physiol, 276, G425

Lancaster, 1990, Flavor biochemistry, vol. 3, 33

Fenwick, 1985, The genus Allium, CRC Crit. Rev. Food Sci. Nutr, 22, 273, 10.1080/10408398509527417

Lawson, 1993, Bioactive organosulfur compounds of garlic and garlic products. Role in reducing blood lipids, ACS Symp. Ser, 534, 306, 10.1021/bk-1993-0534.ch021

You, 1989, Allium vegetables and reduced risk of stomach cancer, J. Natl. Cancer Inst, 81, 162, 10.1093/jnci/81.2.162

Ernst, 1997, Can Allium vegetables prevent cancer?, Phytomedicine, 4, 79, 10.1016/S0944-7113(97)80032-3

Dorant, 1996, Consumption of onions and a reduced risk of stomach carcinoma, Gastroenterology, 110, 12, 10.1053/gast.1996.v110.pm8536847

Sparnins, 1988, Effects of organosulfur compounds from garlic and onions on benzo(a)pyrene-induced neoplasia and glutathione S-transferase activity in the mouse, Carcinogenesis, 9, 131, 10.1093/carcin/9.1.131

Sumiyoshi, 1990, Chemoprevention of 1,2-dimethylhydrazine-induced colon cancer in mice by naturally occurring organosulfur compounds, Cancer Res, 50, 5084

Hu, 1997, Induction of glutathione S-transferase π as a bioassay for the evaluation of potency of inhibitors of benzo(a)pyrene-induced cancer in a murine model, Int. J. Cancer, 73, 897, 10.1002/(SICI)1097-0215(19971210)73:6<897::AID-IJC23>3.0.CO;2-0

Guyonnet, 2001, Antimutagenic activity of organosulfur compounds from Allium is associated with Phase 2 enzyme induction, Mutat. Res, 495, 135, 10.1016/S1383-5718(01)00205-4

Singh, 1998, Differential induction of NAD(P)H, Biochem. Biophys. Res. Commun, 244, 917, 10.1006/bbrc.1998.8352

Talalay, 2000, Chemoprotection against cancer by induction of Phase 2 enzymes, BioFactors, 12, 5, 10.1002/biof.5520120102

Ross, 2000, NAD(P)H, Chem. Biol. Interact, 129, 77, 10.1016/S0009-2797(00)00199-X

Munday, 1999, MundayC. M. Low doses of diallyl disulfide, a compound derived from garlic, increase tissue activities of quinone reductase and glutathione transferase in the gastrointestinal tract of the rat, Nutr. Cancer, 34, 42, 10.1207/S15327914NC340106

Munday, 2001, Munday, C. M. Relative activities of organosulfur compounds derived from onions and garlic in increasing tissue activities of quinone reductase and glutathione transferase in rat tissues, Nutr. Cancer, 40, 205, 10.1207/S15327914NC402_18

Kirk, 1979, Effects of feeding cull domestic onions (Allium cepa) to sheep, Am. J. Vet. Res, 40, 397

Rae, 1999, Onion toxicosis in a herd of beef cows, Can. Vet. J, 40, 55

van der Kolk, 2000, Onion poisoning in a herd of dairy cattle, Vet. Rec, 147, 517, 10.1136/vr.147.18.517

Verhoeff, 1985, Onion poisoning of young cattle, Vet. Rec, 117, 497, 10.1136/vr.117.19.497

Hutchison, 1977, Onions as a cause of Heinz body anemia and death in cattle, Can. Vet. J, 18, 358

Pierce, 1972, Acute hemolytic anemia caused by wild onion poisoning in horses, J. Am. Vet. Med. Assoc, 160, 323

Stevens, 1984, Suspected wild garlic poisoning in sheep, Vet. Rec, 115, 363, 10.1136/vr.115.14.363-a

Van Kampen, 1970, Hemolytic anemia in sheep fed wild onion (Allium validum), J. Am. Vet. Med. Assoc, 156, 328

Kobayashi, 1981, Onion poisoning in the cat, Feline Pract, 11, 22

Robertson, 1998, Heinz body formation in cats fed baby food containing onion powder, J. Am. Vet. Med. Assoc, 212, 1260, 10.2460/javma.1998.212.08.1260

Spice, 1976, Hemolytic anemia associated with ingestion of onions in a dog, Can. Vet. J, 17, 181

Gebauer, 1954, Zwiebelanämie, Vitamin B12, und Folsäure, Pharmazie, 9, 475

Majori, L.; Squeri, L. Modificazioni ematologiche nella cavia e nel ratto albino per ingestione di Allium cepa. Boll. Soc. Ital. Biol. Sper. 30:791–792; 1954

Gruhzit, 1931, Anemia of dogs produced by feeding of the whole onions and of onion fractions, Am. J. Med. Sci, 181, 812, 10.1097/00000441-193106000-00007

Munday, 1994, Comparative toxicity of prop(en)yl disulfides derived from Alliaceae, J. Agric. Food Chem, 42, 959, 10.1021/jf00040a023

Hase, 1982, A convenient synthesis of symmetrical disulfides, Synth. Comm, 12, 947, 10.1080/00397918208061931

Milligan, B.; Saville, B.; Swan, J. M. New syntheses of trisulphides. J. Chem. Soc. 4850–4853; 1962

Moore, 1962, The reaction of triphenylphosphine with organic disulphides and polysulphides, Tetrahedron, 18, 205, 10.1016/S0040-4020(01)92653-5

Munday, 1995, In vivo toxicity of thiols, Methods Enzymol, 251, 117, 10.1016/0076-6879(95)51115-6

Fairbanks, 1976, Hemoglobin, hemoglobin derivatives, and myoglobin, 401

Cohen, 1964, Generation of hydrogen peroxide in erythrocytes by hemolytic agents, Biochemistry, 3, 895, 10.1021/bi00895a006

Beutler, 1963, Improved method for the determination of blood glutathione, J. Lab. Clin. Med, 61, 882

Dacie, 1995

Evelyn, 1938, Microdetermination of oxyhemoglobin, methemoglobin, and sulfhemoglobin in a single sample of blood, J. Biol. Chem, 126, 655, 10.1016/S0021-9258(18)73873-8

Winterbourn, 1979, Protection by ascorbate against acetylphenylhydrazine-induced Heinz body formation in glucose-6-phosphate dehydrogenase deficient erythrocytes, Br. J. Haematol, 41, 245, 10.1111/j.1365-2141.1979.tb05853.x

Ernster, 1967, DT diaphorase, Methods Enzymol, 10, 309, 10.1016/0076-6879(67)10059-1

Habig, 1974, Glutathione S-transferases, J. Biol. Chem, 249, 7130, 10.1016/S0021-9258(19)42083-8

Munday, 1985, Toxicity of aromatic disulphides. III. In vivo hemolytic activity of aromatic disulphides, J. Appl. Toxicol, 5, 414, 10.1002/jat.2550050615

Jarolim, 1990, Effect of hemoglobin oxidation products on the stability of red cell membrane skeletons and the associations of skeletal proteins, Blood, 76, 2125, 10.1182/blood.V76.10.2125.2125

Munday, 1994, Bioactivation of thiols by one-electron oxidation, Adv. Pharmacol, 27, 237, 10.1016/S1054-3589(08)61035-2

Munday, 1989, Toxicity of thiols and disulphides, Free Radic. Biol. Med, 7, 659, 10.1016/0891-5849(89)90147-0

Prütz, 1993, Sulfane-activated reduction of cytochrome c by glutathione, Free Radic. Res. Commun, 18, 159, 10.3109/10715769309147489

Pickering, 1967, Disproportionation of organic polysulfides, J. Am. Chem. Soc, 89, 2364, 10.1021/ja00986a021

Kreevoy, 1960, Inductive effects on the acid dissociation constants of mercaptans, J. Am. Chem. Soc, 82, 4899, 10.1021/ja01503a037

Yabroff, 1940, Extraction of mercaptans with alkaline solutions, Ind. Eng. Chem, 32, 257, 10.1021/ie50362a022

Everett, 1995, Perthiols as antioxidants, Methods Enzymol, 251, 55, 10.1016/0076-6879(95)51110-5

Park, 1986, Sulfhemoglobin. Properties of partially sulfated tetramers, J. Biol. Chem, 261, 8805, 10.1016/S0021-9258(19)84452-6

Carrico, 1978, The preparation and some physical properties of sulfhemoglobin, J. Biol. Chem, 253, 2386, 10.1016/S0021-9258(17)38086-9

Toohey, 1989, Sulphane sulphur in biological systems, Biochem. J, 264, 625, 10.1042/bj2640625

Zijlstra, 1996, Definition, significance, and measurement of quantities pertaining to the oxygen-carrying properties of the blood, Scand. J. Clin. Lab. Invest, 56, 27, 10.3109/00365519609088623

Fukushima, 1990, On the mechanism of loss of deformability in human erythrocytes due to Heinz body formation, Toxicol. Appl. Pharmacol, 102, 205, 10.1016/0041-008X(90)90021-L

Lord, 1967, Erythropoietic cell proliferation during recovery from acute haemorrhage, Brit. J. Haematol, 13, 160, 10.1111/j.1365-2141.1967.tb08726.x

Jenkins, 1972, The no-effect dose of aniline in human subjects and a comparison of aniline toxicity in man and the rat, Food Cosmet. Toxicol, 10, 671, 10.1016/S0015-6264(72)80147-0

Dinkova-Kostova, 2001, Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups, Proc. Natl. Acad. Sci. USA, 98, 3404, 10.1073/pnas.051632198

Primiano, 1997, Redox regulation of genes that protect against carcinogens, Comp. Biochem. Physiol. B Biochem. Mol. Biol, 118, 487, 10.1016/S0305-0491(97)00221-6

Shen, 1996, Enhanced diallyl trisulphide has in vitro synergy with amphotericin B against Cryptococcus neoformans, Planta Med, 62, 415, 10.1055/s-2006-957929

Oser, 1972, Progress in the consideration of flavoring ingredients under the Food Additives Amendment. 5. GRAS substances, Food Technol. (Chicago), 38, 35

Keller, 1971