Could nitrile derivatives of turnip (Brassica rapa) glucosinolates be hepato- or cholangiotoxic in cattle?

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 30, 2014, Pages 7370-7375

  Collett, Mark G ^a   Stegelmeier, Bryan L ^b   Tapper, Brian A ^c  

^a MASSEY UNIVERSITY   (New Zealand)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

^c AGRESEARCH GRASSLANDS   (New Zealand)

Author keywords

bile duct; bovine; Brassica rapa; epithionitrile; glucosinolate; hepatotoxin; nitrile; turnip

Indexed keywords

BODY FLUIDS; CHEMICAL CONTAMINATION; CYANIDES; DUCTS; MAMMALS;

BILE DUCTS; BOVINE; BRASSICA RAPA; EPITHIONITRILE; GLUCOSINOLATES; HEPATOTOXINS; NITRILE; TURNIP;

DERIVATIVES;

BOS; BOVINAE; BRASSICA; BRASSICA NAPUS; BRASSICA RAPA; BRASSICA RAPA SUBSP. RAPA; LEPTOSPHAERULINA CHARTARUM; RATTUS;

1-CYANO-3,4-EPITHIOBUTANE; 3-BUTENYL GLUCOSINOLATE; 3-OXO-3-PHENYLPROPANENITRILE; 4-PENTENENITRILE; GLUCOBRASSICIN; GLUCONASTURTIIN; GLUCOSINOLATE; INDOLE DERIVATIVE; INDOLE-3-ACETONITRILE; NITRILE; PROGOITRIN;

ANIMAL; BOVINAE; BRASSICA RAPA; CHEMISTRY; DISEASE MODEL; DRUG EFFECTS; LIVER; METABOLISM; MOUSE; NEW ZEALAND; RAPESEED; RAT; TOXIC HEPATITIS; VETERINARY;

ANIMALS; BRASSICA NAPUS; BRASSICA RAPA; CATTLE; DISEASE MODELS, ANIMAL; DRUG-INDUCED LIVER INJURY; GLUCOSINOLATES; INDOLES; LIVER; MICE; NEW ZEALAND; NITRILES; RATS;

EID: 84905270264     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf500526u     Document Type: Conference Paper

References (59)

1. Morton, J. M.; Campbell, P. H. Disease signs reported in south-eastern Australian dairy cattle while grazing Brassica species Aust. Vet. J. 1997, 75, 109-113
2. Collett, M. G.; Matthews, Z. M. Photosensitivity in cattle grazing Brassica crops Int. J. Poisonous Plant Res. 2013, 3, xx-yy (in press)
3. Collett, M. G. Bile duct lesions associated with turnip (Brassica rapa) photosensitization compared to those due to sporidesmin toxicosis in dairy cows Vet. Pathol. 2014, 10.1177/0300985813513042
4. Grubb, C. D.; Abel, S. Glucosinolate metabolism and its control Trends Plant Sci. 2006, 11, 89-100
5. Wittstock, U.; Halkier, B. A. Glucosinolate research in the Arabidopsis era Trends Plant Sci. 2002, 7, 263-270
6. Carlson, D. G.; Daxenbichler, M. E.; VanEtten, C. H.; Tookey, H. L.; Williams, P. H. Glucosinolates in crucifer vegetables: turnips and rutabagas J. Agric. Food Chem. 1981, 29, 1235-1239
7. Carlson, D. G.; Daxenbichler, M. E.; Tookey, H. L.; Kwolek, W. F.; Hill, C. B.; Williams, P. H. Glucosinolates in turnip tops and roots: cultivars grown for greens and/or roots J. Am. Soc. Hortic. Sci. 1987, 112, 179-183
8. Matthäus, B.; Luftmann, H. Glucosinolates in members of the family Brassicaceae: separation and identification by LC/ESI-MS-MS J. Agric. Food Chem. 2000, 48, 2234-2239
9. Kim, S.-J.; Ishida, M.; Matsuo, T.; Watanabe, M.; Watanabe, Y. Separation and identification of glucosinolates of vegetable turnip rape by LC/APCI-MS and comparison of their contents in ten cultivars of vegetable turnip rape (Brassica rapa L.) Soil Sci. Plant Nutr. 2001, 47, 167-177
10. Zukalová, H.; Vašák, J.; Nerad, D.; Štranc, P. The role of glucosinolates of Brassica genus in the crop system Rostlinna Vyroba 2002, 48, 181-189
11. Padilla, G.; Cartea, M. E.; Velasco, P.; De Haro, A.; Ordás, A. Variation of glucosinolates in vegetable crops of Brassica rapa Phytochemistry 2007, 68, 536-545
12. Barry, T. N. The feeding value of forage brassica plants for grazing ruminant livestock Anim. Feed Sci. Technol. 2013, 181, 15-25
13. Tookey, H. L. Crambe thioglucoside glucohydrolase (EC 3.2.3.1): separation of a protein required for epithiobutane formation Can. J. Biochem. 1973, 51, 1654-1660
14. MacLeod, A. J.; Rossiter, J. T. The occurrence and activity of epithiospecifier protein in some Cruciferae seeds Phytochemistry 1985, 24, 1895-1898
15. Bernardi, R.; Negri, A.; Ronchi, S.; Palmieri, S. Isolation of the epithiospecifier protein from oil-rape (Brassica napus ssp. oleifera) seed and its characterization FEBS Lett. 2000, 467, 296-298
16. Kissen, R.; Bones, A. M. Nitrile-specifier proteins involved in glucosinolate hydrolysis in Arabidopsis thaliana J. Biol. Chem. 2009, 284, 12057-12070
17. Gil, V.; MacLeod, A. J. The effects of pH on glucosinolate degradation by a thioglucoside glucohydrolase preparation Phytochemistry 1980, 19, 2547-2551
18. Agerbirk, N.; Olsen, C. E.; Sørensen, H. Initial and final products, nitriles, and ascorbigens produced in myrosinase-catalyzed hydrolysis of indole glucosinolates J. Agric. Food Chem. 1998, 45, 1563-1571
19. Mullaney, J. A.; Kelly, W. J.; McGhie, T. K.; Ansell, J.; Heyes, J. A. Lactic acid bacteria convert glucosinolates to nitriles efficiently yet differently from Enterobacteriaceae J. Agric. Food Chem. 2013, 61, 3039-3046
20. Daxenbichler, M. E.; VanEtten, C. H.; Brown, F. S.; Jones, Q. Oxazolidinethiones and volatile isothiocyanates in enzyme-treated seed meals from 65 species of Cruciferae J. Agric. Food Chem. 1964, 12, 127-130
21. Paik, I. K.; Robblee, A. R.; Clandinin, D. R. Products of the hydrolysis of rapeseed glucosinolates Can. J. Anim. Sci. 1980, 60, 481-493
22. Cartea, M. E.; Velasco, P. Glucosiniolates in Brassica foods: bioavailability in food and significance for human health Phytochem. Rev. 2008, 7, 213-229
23. 2+ catalyzed formation of nitriles and thionamides from intact glucosinolates J. Nat. Prod. 2008, 71, 76-80
24. Forss, D. A.; Barry, T. N. Observations on nitrile production during autolysis of kale and swedes, and their stability during incubation with rumen fluid J. Sci. Food Agric. 1983, 34, 1077-1084
25. Bones, A. M.; Rossiter, J. T. The myrosinase-glucosinolate system, its organization and biochemistry Physiol. Plant. 1996, 97, 194-208
26. U.S. National Library of Medicine, ChemID plus, http://www.chem.sis.nlm.nih.gov/chemidplus (accessed Jan 30, 2014).
27. Daxenbichler, M. E.; VanEtten, C. H.; Tallent, W. H.; Wolff, I. A. Rapeseed meal autolysis. Formation of diastereomeric (2 R)-1-cyano-2-hydroxy-3,4-epithiobutanes from progoitrin Can. J. Chem. 1967, 45, 1971-1974
28. Daxenbichler, M. E.; VanEtten, C. H.; Wolff, I. A. Diastereomeric episulfides from epi -progoitrin upon autolysis of crambe seed meal Phytochemistry 1968, 7, 989-996
29. VanEtten, C. H.; Daxenbichler, M. E. Formation of organic nitriles from progoitrins in leaves of Crambe abyssinica and Brassica napus J. Agric. Food Chem. 1971, 19, 194-195
30. Kirk, J. T. O.; MacDonald, C. G. 1-Cyano-3,4-epithiobutane: a major product of glucosinolate hydrolysis in seeds from certain varieties of Brassica campestris Phytochemistry 1974, 13, 2611-2615
31. Cole, R. A. Isothiocyanates, nitriles and thiocyanates as products of autolysis of glucosinolates in Cruciferae Phytochemistry 1976, 15, 759-762
32. Daxenbichler, M. E.; VanEtten, C. H.; Spencer, G. F. Glucosinolates and derived products in cruciferous vegetables. Identification of organic nitriles from cabbage J. Agric. Food Chem. 1977, 25, 121-124
33. McDanell, R.; McLean, A. E. M.; Hanley, A. B.; Heaney, R. K.; Fenwick, G. R. Chemical and biological properties of indole glucosinolates (glucobrassicins): a review Food Chem. Toxicol. 1988, 26, 59-70
34. VanEtten, C. H.; Daxenbichler, M. E.; Wolff, I. A. Natural glucosinolates (thioglucosides) in foods and feeds J. Agric. Food Chem. 1969, 17, 483-491
35. VanEtten, C. H.; Gagne, W. E.; Robbins, D. J.; Booth, A. N.; Daxenbichler, M. E.; Wolff, I. A. Biological evaluation of crambe seed meals and derived products by rat feeding Cereal Chem. 1969, 46, 145-155
36. Gould, D. H.; Gumbmann, M. R.; Daxenbichler, M. E. Pathological changes in rats fed the crambe meal-glucosinolate hydrolytic products, 2 S -1-cyano-2-hydroxy-3,4-epithiobutanes (erythro and threo) for 90 days Food Cosmet. Toxicol. 1980, 18, 619-625
37. Nishie, K.; Daxenbichler, M. E. Toxicology of glucosinolates, related compounds (nitriles, R -goitrin, isothiocyanates) and vitamin U found in Cruciferae Food Cosmet. Toxicol. 1980, 18, 159-172
38. Gould, D. H.; Fettman, M. J.; Daxenbichler, M. E.; Bartuska, B. M. Functional and structural alterations of the rat kidney induced by the naturally occurring organonitrile 2 S -1-cyano-2-hydroxy-3,4-epithiobutane Toxicol. Appl. Pharmacol. 1985, 78, 190-201
39. Wallig, M. A.; Gould, D. H.; Fettman, M. J.; Willhite, C. C. Comparative toxicities of the naturally occurring nitrile 1-cyano-3,4-epithiobutane and the synthetic nitrile n -valeronitrile in rats: differences in target organs, metabolism and toxic mechanisms Food Chem. Toxicol. 1988, 26, 149-157
40. Dietz, H. M.; Panigrahi, S.; Harris, R. V. Toxicity of hydrolysis products from 3-butenyl glucosinolate in rats J. Agric. Food Chem. 1991, 39, 311-315
41. Wallig, M. A.; Gould, D. H.; Fettman, M. J. Selective pancreatotoxicity in the rat induced by the naturally occurring plant nitrile 1-cyano-2-hydroxy-3-butene Food Chem. Toxicol. 1988, 26, 137-147
42. Ghanayem, B. I.; Burka, L. T. Excretion and identification of methacrylonitrile in the bile of male F344 rats Drug Metab. Dispos. 1996, 24, 390-394
43. Brocker, E. R.; Benn, M. H. The intramolecular formation of epithioalkanenitriles from alkenylglucosinolates by Crambe abyssinica seed flour Phytochemistry 1983, 22, 770-772
44. Benn, M. Glucosinolates Pure Appl. Chem. 1977, 49, 197-210
45. Lüthy, J.; Benn, M. Cyanoepithioalkanes: some chemical and toxicological studies. In Natural Sulfur Compounds; Cavallini, D.; Gaull, G. E.; Zappia, V., Eds.; Plenum Press: New York, 1980; pp 381-389.
46. Brocker, E. R.; Benn, M. H.; Lüthy, J.; Von Däniken, A. Metabolism and distribution of 3,4-epithiobutanenitrile in the rat Food Chem. Toxicol. 1984, 22, 227-232
47. Fokin, A. V.; Kolomiets, A. F. The reactivity of epithio-compounds Russ. Chem. Rev. 1976, 45, 25-42
48. VanSteenhouse, J. L.; Fettman, M. J.; Gould, D. H. Sequential changes in hepatic and renal glutathione and development of renal karyomegaly in 1-cyano-3,4-epithiobutane toxicity in rats Food Chem. Toxicol. 1989, 27, 731-739
49. VanSteenhouse, J. L.; Prescott, J. S.; Barker, S. A. Identification of the 1-cyano-3,4-epithiobutane-derived urinary mercapturic acid n -acetyl- s -(4-cyano-2-thio-1-butyl)-cysteine in male Fischer 344 rats J. Appl. Toxicol. 2000, 20, 1-10
50. VanSteenhouse, J. L.; Prescott, J. S.; Swenson, D. H. Protection from 1-cyano-3,4-epithiobutane nephrotoxicity by aminooxyacetic acid and effect on xenobiotic-metabolizing enzymes in male Fischer 344 rats J. Appl. Toxicol. 1999, 19, 237-249
51. Willhite, C. C.; Smith, R. P. The role of cyanide liberation in the acute toxicity of aliphatic nitriles Toxicol. Appl. Pharmacol. 1981, 59, 589-602
52. Tanii, H.; Hashimoto, K. Studies on the mechanism of acute toxicity of nitriles in mice Arch. Toxicol. 1984, 55, 47-54
53. Ahmed, A. E.; Farooqui, M. Y. H. Comparative toxicities of aliphatic nitriles Toxicol. Lett. 1982, 12, 157-163
54. Silver, E. H.; Kuttab, S. H.; Hasan, T.; Hassan, M. Structural considerations in the metabolism of nitriles to cyanide in vivo Drug Metab. Dispos. 1982, 10, 495-498
55. Duncan, A. J.; Milne, J. A. Effect of long-term intra-ruminal infusion of the glucosinolate metabolite allyl cyanide on the voluntary food intake and metabolism of lambs J. Sci. Food Agric. 1992, 58, 9-14
56. Duncan, A. J.; Milne, J. A. Effects of oral administration of brassica secondary metabolites, allyl cyanide, allyl isothiocyanate and dimethyl disulphide, on the voluntary food intake and metabolism of sheep Br. J. Nutr. 1993, 70, 631-645
57. Niedoborski, T. E.; Klein, B. P.; Wallig, M. A. Rapid isolation and purification of 1-cyano-2-hydroxy-3-butene (crambene) from Crambe abyssinica seed meal using immiscible solvent extraction and high-performance liquid chromatography J. Agric. Food Chem. 2001, 49, 3594-3599
58. VanEtten, C. H.; Daxenbichler, M. E.; Schroeder, W.; Princen, L. H.; Perry, T. W. Tests for epi -progoitrin, derived nitriles, and goitrin in body tissues from cattle fed crambe meal Can. J. Anim. Sci. 1977, 57, 75-80
59. Westwood, C. T.; Mulcock, H. Nutritional evaluation of five species of forage brassica Proc. N.Z. Grassland Assoc. 2012, 74, 31-38