1-Cyano-3,4-epithiobutane: A major product of glucosinolate hydrolysis in seeds from certain varieties of Brassica campestris

Kirk, John T. O.; Macdonald, Colin G.

doi:10.1016/s0031-9422(00)86946-0

Cited by 40 publications

(20 citation statements)

References 20 publications

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“…Since its identification, ESP has been identified in a number of nitrile-forming cruciferous plants (Cole, 1978;Kaoulla et al, 1980;Petroski and Tookey, 1982;MacLeod and Rossiter, 1985). The formation of epithionitriles has been shown to be heat sensitive in the seed of turnip rape (Brassica campestris), where a mild heat treatment was shown to decrease the formation of epithionitriles and increase the formation of isothiocyanates from benzylglucosinolate without retarding myrosinase activity (Kirk and Macdonald, 1974).…”

Section: Effect Of Heat Treatment On Sulforaphane Formation Esp Actimentioning

confidence: 99%

“…This protein does not catalyze glucosinolate hydrolysis by itself, but instead directs the products of glucosinolate hydrolysis toward epithionitriles, rather than isothiocyanates. Epithiospecifier protein requires iron for its activity, and heat treatment has been shown to decrease the formation of epithionitriles in seeds of turnip rape (Brassica campestris; Kirk and Macdonald, 1974). A recent study in the experimental plant Arabidopsis thaliana suggests that ESP may regulate nitrile formation in addition to epithionitrile formation (Lambrix et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

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Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli

Matusheski¹,

Juvik²,

Jeffery³

2004

Phytochemistry

268

265

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Section: Effect Of Heat Treatment On Sulforaphane Formation Esp Actimentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli

Matusheski¹,

Juvik²,

Jeffery³

2004

Phytochemistry

268

265

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“…It is well documented that different species and varieties of cruciferous vegetables express differing glucosinolate contents (7,37,38). Additionally, the ratio of isothiocyanate to nitrile produced from a parent glucosinolate has been found to vary among species and even among different varieties of the same species (6,27,39). The conditions under which hydrolysis takes place can also affect the ratio of isothiocyanates to nitriles formed.…”

Section: Animal Experiments Experiments 1 Sf Treatmentmentioning

confidence: 99%

Comparison of the Bioactivity of Two Glucoraphanin Hydrolysis Products Found in Broccoli, Sulforaphane and Sulforaphane Nitrile

Matusheski

Jeffery

2001

J. Agric. Food Chem.

209

161

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Epidemiological and laboratory studies suggest that dietary broccoli may prevent or delay a variety of cancers. Broccoli and other crucifers contain a relatively unique family of secondary metabolites called glucosinolates. Glucoraphanin, the major glucosinolate in broccoli, is hydrolyzed by an endogenous plant myrosinase to form either the potent anticarcinogen sulforaphane (SF) or sulforaphane nitrile (SF nitrile). The bioactivities of SF and SF nitrile were compared in rats and in mouse hepatoma cells. Male, 4-week-old, Fischer 344 rats were administered SF or SF nitrile (200, 500, or 1000 micromol/kg) by gavage daily for 5 days. Hepatic, colonic mucosal, and pancreatic quinone reductase and glutathione S-transferase activities were induced by high doses of SF, but not by SF nitrile. When Hepa 1c1c7 cells were exposed to increasing levels of each compound for 24 h, quinone reductase showed a 3-fold maximal induction over control at 2.5 microM SF and a 3.5-fold maximal induction over control at 2000 microM SF nitrile, the highest concentration tested. These results demonstrate that SF nitrile is substantially less potent than SF as an inducing agent of phase II detoxification enzymes. Therefore, glucoraphanin hydrolysis directed toward the production of SF rather than SF nitrile could increase the potential chemoprotective effects of broccoli.

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“…This transformation was first observed in autolysing seed meal preparations (18,19,20), but apparently it can also occur in fresh-plant extracts (8,21). Scheme VIII summarises these reports.…”

Section: Chmentioning

confidence: 88%

“…As the original investigators (18,19,20) noted this suggests some non-enzymatic process, and leads us to consider possibilities.…”

Section: Chmentioning

confidence: 99%

Glucosinolates

Benn¹

1977

Pure and Applied Chemistry

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The catabolism of glucosinolates is reviewed, with particular attention to the formation of "abnormal" products (thiocyanates, and cyano-epithioalkanes). The biological properties of the glucosinolates and catabolites are briefly surveyed. INTRODUC TI ON Some twenty years have elapsed since Ettlinger and Lundeen proposed .!. as the correct structure for glucosinolate anions. HO~~ OS~N OH bso- HO OHSince passing that milestone there have been major achievements in identifying glucosinolates (the list of which now exceeds 70), andin mapping the biosynthetic pathways at the substrate level. There are recent and authoritative reviews of these advances (1) and I propose to say no more about them here. There has also been a fresh discussion of the value of glucosinolates in plant systematics (2), and that too I shall leave aside. Instead I have chosen to concentrate upon the catabolism of glucosinolates, and their biological properties. GLUCOSINOLATE CATABOLISM"Normal Catabolism'~ When plant tissues containing glucosinolates are crushed there is usually formation of isothiocyanates ("mustard oils") (~) corresponding to the aglucone (~). (Itwas the early recognition of this "normal" catabolism which resulted in the old name "mustard oil glucosides" for the glucosinolates).The isothiocyanate-forming enzymes are known as myrosinases and, after soine controversy, it has been established that their role is to function as thioglucoside glucohydrolases (E. C. 3. 2. 3. 1) remarkably catholic in their acceptance of.!. with a wide va:riety of ltsub-197

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1-Cyano-3,4-epithiobutane: A major product of glucosinolate hydrolysis in seeds from certain varieties of Brassica campestris

Cited by 40 publications

References 20 publications

Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli

Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli

Comparison of the Bioactivity of Two Glucoraphanin Hydrolysis Products Found in Broccoli, Sulforaphane and Sulforaphane Nitrile

Glucosinolates

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