Thermally induced degradation of aliphatic glucosinolates: Identification of intermediary breakdown products and proposed degradation pathways

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 39, 2012, Pages 9890-9899

  Hanschen, Franziska S ^a   Bauer, Anna ^a   Mewis, Inga ^b   Keil, Claudia ^a   Schreiner, Monika ^b   Rohn, Sascha ^c   Kroh, Lothar W ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b LEIBNIZ INSTITUTE OF VEGETABLE AND ORNAMENTAL CROPS   (Germany)

^c UNIVERSITY OF HAMBURG   (Germany)

Author keywords

broccoli; D thioglucose; isothiocyanate; nitrile; processing; Sinigrin

Indexed keywords

BROCCOLI; D-THIOGLUCOSE; ISOTHIOCYANATES; NITRILE; SINIGRIN;

CYANIDES; GLUCOSE; IRON COMPOUNDS; METAL IONS; PROCESSING;

THERMAL PROCESSING (FOODS);

GLUCOSINOLATE; ISOTHIOCYANIC ACID DERIVATIVE; NITRILE;

ARTICLE; BRASSICA; CHEMISTRY; COOKING; HEAT;

BRASSICA; COOKING; GLUCOSINOLATES; HOT TEMPERATURE; ISOTHIOCYANATES; NITRILES;

BRASSICA; BRASSICA OLERACEA VAR. ITALICA;

EID: 84867079686     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf302744y     Document Type: Article

References (42)

1. Voorrips, L. E.; Goldbohm, R. A.; van Poppel, G.; Sturmans, F.; Hermus, R. J. J.; van den Brandt, P. A. Vegetable and fruit consumption and risks of colon and rectal cancer in a prospective cohort study. The Netherlands cohort study on diet and cancer Am. J. Epidemiol. 2000, 152, 1081-1092
2. Jeffery, E.; Araya, M. Physiological effects of broccoli consumption Phytochem. Rev. 2009, 8, 283-298
3. Halkier, B. A.; Gershenzon, J. Biology and biochemistry of glucosinolates Annu. Rev. Plant Biol. 2006, 57, 303-333
4. Lambrix, V.; Reichelt, M.; Mitchell-Olds, T.; Kliebenstein, D. J.; Gershenzon, J. The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory Plant Cell 2001, 13, 2793-2807
5. Fahey, J. W.; Haristoy, X.; Dolan, P. M.; Kensler, T. W.; Scholtus, I.; Stephenson, K. K.; Talalay, P.; Lozniewski, A. Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[ a ]pyrene-induced stomach tumors Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 7610-7615
6. Conaway, C. C.; Jiao, D.; Chung, F.-L. Inhibition of rat liver cytochrome P450 isozymes by isothiocyanates and their conjugates: A structure-activity relationship study Carcinogenesis 1996, 17, 2423-2427
7. Mi, L.; Wang, X.; Govind, S.; Hood, B. L.; Veenstra, T. D.; Conrads, T. P.; Saha, D. T.; Goldman, R.; Chung, F.-L. The role of protein binding in induction of apoptosis by phenethyl isothiocyanate and sulforaphane in human non-small lung cancer cells Cancer Res. 2007, 67, 6409-6416
8. Zhang, Y.; Talalay, P.; Cho, C. G.; Posner, G. H. A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2399-2403
9. Fahey, J. W.; Zhang, Y.; Talalay, P. Broccoli sprouts: An exceptionally rich source of inducers of enzymes that protect against chemical carcinogens Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10367-10372
10. Mahéo, K.; Morel, F.; Langouët, S.; Kramer, H.; Le Ferrec, E.; Ketterer, B.; Guillouzo, A. Inhibition of cytochromes P-450 and induction of glutathione S -transferases by sulforaphane in primary human and rat hepatocytes Cancer Res. 1997, 57, 3649-3652
11. Fimognari, C.; Nüsse, M.; Cesari, R.; Iori, R.; Cantelli-Forti, G.; Hrelia, P. Growth inhibition, cell-cycle arrest and apoptosis in human T-cell leukemia by the isothiocyanate sulforaphane Carcinogenesis 2002, 23, 581-586
12. Verkerk, R.; Schreiner, M.; Krumbein, A.; Ciska, E.; Holst, B.; Rowland, I.; De Schrijver, R.; Hansen, M.; Gerhäuser, C.; Mithen, R.; Dekker, M. Glucosinolates in Brassica vegetables: The influence of the food supply chain on intake, bioavailability and human health Mol. Nutr. Food Res. 2009, 53, 219-265
13. Volden, J.; Borge, G. I. A.; Hansen, M.; Wicklund, T.; Bengtsson, G. B. Processing (blanching, boiling, steaming) effects on the content of glucosinolates and antioxidant-related parameters in cauliflower (Brassica oleracea L. ssp. botrytis) LWT-Food Sci. Technol. 2009, 42, 63-73
14. Cieślik, E.; Leszczyńska, T.; Filipiak-Florkiewicz, A.; Sikora, E.; Pisulewski, P. M. Effects of some technological processes on glucosinolate contents in cruciferous vegetables Food Chem. 2007, 105, 976-981
15. Oerlemans, K.; Barrett, D. M.; Suades, C. B.; Verkerk, R.; Dekker, M. Thermal degradation of glucosinolates in red cabbage Food Chem. 2006, 95, 19-29
16. Hanschen, F. S.; Rohn, S.; Mewis, I.; Schreiner, M.; Kroh, L. W. Influence of the chemical structure on the thermal degradation of the glucosinolates in broccoli sprouts Food Chem. 2012, 130, 1-8
17. Dekker, M.; Hennig, K.; Verkerk, R. Differences in thermal stability of glucosinolates in five Brassica vegetables Czech. J. Food Sci. 2009, 27, S85-S88
18. Hanschen, F. S.; Platz, S.; Mewis, I.; Schreiner, M.; Rohn, S.; Kroh, L. W. Thermally induced degradation of sulfur-containing aliphatic glucosinolates in broccoli sprouts (Brassica oleracea var. italica) and model systems J. Agric. Food Chem. 2012, 60, 2231-2241
19. Williams, D. J.; Critchley, C.; Pun, S.; Chaliha, M.; O'Hare, T. J. Differing mechanisms of simple nitrile formation on glucosinolate degradation in Lepidium sativum and Nasturtium officinale seeds Phytochemistry 2009, 70, 1401-1409
20. Gronowitz, S.; Svensson, L.; Ohlson, R. Studies of some nonenzymic reactions of progoitrin J. Agric. Food Chem. 1978, 26, 887-890
21. MacLeod, A. J.; Rossiter, J. T. Non-enzymic degradation of 2-hydroxybut-3-enylglucosinolate (progoitrin) Phytochemistry 1986, 25, 855-858
22. MacLeod, A. J.; Panesar, S. S.; Gil, V. Thermal degradation of glucosinolates Phytochemistry 1981, 20, 977-980
23. Volden, J.; Wicklund, T.; Verkerk, R.; Dekker, M. Kinetics of changes in glucosinolate concentrations during long-term cooking of white cabbage (Brassica oleracea L. ssp. capitata f. alba) J. Agric. Food Chem. 2008, 56, 2068-2073
24. Oliviero, T.; Verkerk, R.; Dekker, M. Effect of water content and temperature on glucosinolate degradation kinetics in broccoli (Brassica oleracea var. italica) Food Chem. 2012, 132, 2037-2045
25. Hennig, K.; Verkerk, R.; Bonnema, G.; Dekker, M. Rapid estimation of glucosinolate thermal degradation rate constants in leaves of Chinese kale and broccoli (Brassica oleracea) in two seasons J. Agric. Food Chem. 2012, 60, 7859-7865
26. Youngs, C. G.; Perlin, A. S. Fe(II)-catalyzed decomposition of sinigrin and related thioglycosides Can. J. Chem. 1967, 45, 1801-1804
27. 2+-catalyzed formation of nitriles and thionamides from intact glucosinolates J. Nat. Prod. 2008, 71, 76-80
28. Austin, F. L.; Gent, C. A.; Wolff, I. A. Degradation of natural thioglucosides with ferrous salts J. Agric. Food Chem. 1968, 16, 752-755
29. Thies, W. Isolation of sinigrin and glucotropaeolin from cruciferous seeds Fett/Lipid 1988, 90, 311-314
30. Pérez-Balibrea, S.; Moreno, D. A.; Garcìa-Viguera, C. Improving the phytochemical composition of broccoli sprouts by elicitation Food Chem. 2011, 129, 35-44
31. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 1976, 72, 248-254
32. Mewis, I.; Appel, H. M.; Hom, A.; Raina, R.; Schultz, J. C. Major signaling pathways modulate Arabidopsis glucosinolate accumulation and response to both phloem-feeding and chewing insects Plant Physiol. 2005, 138, 1149-1162
33. König, W. A.; Bauer, H.; Voelter, W.; Bayer, E. Gaschromatographie und massenspektrometrie trifluoracetylierter kohlenhydrate Chem. Ber. 1973, 106, 1905-1919
34. Caraballo, R.; Deng, L.; Amorim, L.; Brinck, T.; Ramström, O. pH-Dependent mutarotation of 1-thioaldoses in water. Unexpected behavior of (2 S)- d -aldopyranoses J. Org. Chem. 2010, 75, 6115-6121
35. Chen, C.-W.; Ho, C.-T. Thermal degradation of allyl isothiocyanate in aqueous solution J. Agric. Food Chem. 1998, 46, 220-223
36. Kawakishi, S.; Namiki, M. Decomposition of allyl isothiocyanate in aqueous solution Agric. Biol. Chem. 1969, 33, 452-459
37. Bones, A. M.; Rossiter, J. T. The myrosinase-glucosinolate system, its organisation and biochemistry Physiol. Plant. 1996, 97, 194-208
38. Hanschen, F. S.; Brüggemann, N.; Brodehl, A.; Mewis, I.; Schreiner, M.; Rohn, S.; Kroh, L. W. Characterization of products from the reaction of glucosinolate-derived isothiocyanates with cysteine and lysine derivatives formed in either model systems or broccoli sprouts J. Agric. Food Chem. 2012, 60, 7735-7745
39. Uda, Y.; Kurata, T.; Arakawa, N. Effects of pH and ferrous ion on the degradation of glucosinolates by myrosinase Agric. Biol. Chem. 1986, 50, 2735-2740
40. Shahidi, F.; Gabon, J.-E. Fate of singrin in methanol/ammonia/water- hexane extraction of B. juncea mustard seed J. Food Sci. 1990, 55, 793-795
41. Hsieh, Y.-H. P.; Hsieh, Y. P. Kinetics of Fe(III) reduction by ascorbic acid in aqueous solutions J. Agric. Food Chem. 2000, 48, 1569-1573
42. Jin, Y.; Wang, M.; Rosen, R. T.; Ho, C.-T. Thermal degradation of sulforaphane in aqueous solution J. Agric. Food Chem. 1999, 47, 3121-3123