1-cyano-2,3-epithiopropane as the primary sinigrin hydrolysis product of fresh cabbage

  title={1-cyano-2,3-epithiopropane as the primary sinigrin hydrolysis product of fresh cabbage},
  author={K. Kyung and H. P. Fleming and C. T. Young and C. Haney},
  journal={Journal of Food Science},
Dichloromethane extracts of juices from fresh cabbages, including four known (Brutus, Galaxy, Bentley, Structon) and two unknown cultivars, were analyzed by GC-MS for the presence of sinigrin degradation products. Allyl isothiocyanate (AITC), which has been reported to be the important aroma compound of freshly disrupted cabbage was not detected in any of the dichloromethane extracts of cabbage juice. Instead, 1-cyano-2,3-epithiopropane, which is one of the isomers of AITC, was the primary… Expand
Occurrence and Flavor Properties of Sinigrin Hydrolysis Products in Fresh Cabbage
Contrary to a published report, allyl isothiocyanate was confirmed as a major volatile sulfur compound along with 1-cyano-2,3-epithiopropane in dichloromethane extracts of freshly disrupted cabbageExpand
Brassica vegetables as sources of epithionitriles: Novel secondary products formed during cooking.
The reactivity of 1-cyano-2,3-epithiopropane under aqueous heat treatment conditions is characterized and three novel compounds were identified as derivatives of the related epithionitriles. Expand
The Brassica epithionitrile 1-cyano-2,3-epithiopropane triggers cell death in human liver cancer cells in vitro.
In vitro data provide no indication that epithionitriles will severely affect human health by Brassica consumption and in contrast to isothiocyanates, no evidence of selective toxicity against HCC cells was found. Expand
Identification of N-Acetyl-S-(3-Cyano-2-(Methylsulfanyl)Propyl-Cysteine as a Major Human Urine Metabolite from the Epithionitrile 1-Cyano-2,3-Epithiopropane, the Main Glucosinolate Hydrolysis Product from Cabbage
Brassica vegetables such as cabbage or pak choi contain alkenyl glucosinolates which can release epithionitriles and to a lesser degree isothiocyanates upon enzymatic hydrolysis. Here, for the firstExpand
1-Cyano-2,3-epithiopropane is a novel plant-derived chemopreventive agent which induces cytoprotective genes that afford resistance against the genotoxic alpha,beta-unsaturated aldehyde acrolein.
Transfection experiments demonstrated that epithionitriles induced gene expression through an antioxidant response element (ARE) and that transactivation of an Nqo1-luciferase reporter plasmid was dependent on NF-E2 p45-related factor 2 (Nrf2), a cap'n'collar basic region leucine zipper transcription factor. Expand
Metabolic profiling of glucosinolates and their hydrolysis products in a germplasm collection of Brassica rapa turnips.
This analysis achieved the comprehensive profiling of all GLS metabolites in a collection of B. rapa turnips, underlining the natural variation not only of intact GLS, but also of their breakdown products. Expand
Isothiocyanates, Nitriles, and Epithionitriles from Glucosinolates Are Affected by Genotype and Developmental Stage in Brassica oleracea Varieties
From a cancer-preventive point of view, consumption of mini heads of the B. oleracea varieties is recommended, because during head development, both glucosinolate concentrations as well as hydrolysis products changed and mini heads contained the highest isothiocyanate concentrations. Expand
Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli.
Examination of the effects of heating broccoli florets and sprouts to determine if broccoli contains ESP activity and to correlate heat-dependent changes in ESP activity, sulforaphane content and bioactivity, as measured by induction of the phase II detoxification enzyme quinone reductase (QR) in cell culture. Expand
Correlation of quinone reductase activity and allyl isothiocyanate formation among different genotypes and grades of horseradish roots.
This study measured GS, GS-hydrolysis products, potential anticancer activity (as quinone reductase inducing activity), total phenolic content, and antioxidant activities from different grades of horseradish accessions. Expand
The selective cytotoxicity of the alkenyl glucosinolate hydrolysis products and their presence in Brassica vegetables.
The activity of glucosinolate hydrolysis products includes cytotoxicity that is compound-class specific and may contribute to their putative chemoprotection properties. Expand


Identification of 1‐cyano‐2,3‐epithiopropane in volatiles of a model system from brussels sprouts (Brassica Oleraceae L var Bullata subvar Gemmifera DC)
Volatiles produced in model systems consisting of a crude enzyme preparation from Brussels sprouts (Brassica oleraceae L var bullata subvar gemmifera DC), sinigrin, ascorbic acid andExpand
1-Cyanoepithioalkanes: major products of alkenylglucosinolate hydrolysis in certain Cruciferae.
Abstract Autolysis of glucosinolates in several crucifers produced 1-cyano-2,3-epithio-propane and 1-cyano-3,4-epithiopentane, in addition to the previously described 1-cyano-3,4-epithiobutane.
Crambe thioglucoside glucohydrolase (EC separation of a protein required for epithiobutane formation.
  • H. L. Tookey
  • Chemistry, Medicine
  • Canadian journal of biochemistry
  • 1973
Sonicated extract of crambe seed meal prepared in the presence of ferrous ion and dithiothreitol enzymatically converts epi-progoitrin to glucose, HSO4−, and a mixture ofExpand
S-Methyl-l-cysteine sulfoxide as the precursor of methyl methanethiolsulfinate, the principal antibacterial compound in cabbage
S-Methyl-L-cysteine sulfoxide (SMCSO) was present in several cultivars of cabbage (Brussicn oleracea) at 690–1,120 ppm. SMCSO was not inhibitory to Leuconostoc mesenreroides, but its hydrolysisExpand
Isothiocyanates, nitriles and thiocyanates as products of autolysis of glucosinolates in Cruciferae
Abstract Glucosinolates from seventy-nine 8-week-old plant species were hydrolysed and the volatile products identified by GC-MS and related to previous published findings. Known compounds,Expand
Gas chromatography‐mass spectrometry of nitriles, isothiocyanates and oxazolidinethiones derived from cruciferous glucosinolates
Hydrolysis/autolysis of the glucosinolates found in wild and cultivated cruciferous plants can yield a variety of nitrogenous compounds for the alkyl or aryl moiety. These products include nitriles,Expand
The volatile sulfur components of cabbage.
SUMMARY Naturally occurring volatile sulfur compounds in cabbage have been identified by mass spectrometry and gas chromatography. Twenty sulfur compounds are reported of which five areExpand
The conversion of potassium allylglucosinolate to 3,4-epithiobutanenitrile by Crambe abyssinica seed flour
Abstract An aqueous suspension of Crambe abyssinica seed flour efficiently converted potassium allylglucosinolate (sinigrin) into 3,4-epithiobutanenitrile.
Investigation of Brassica oleracea and Nasturtium officinale seeds for the presence of epithiospecifier protein
Cabbage exhibited behaviour commensurate with possession of an epithiospecifier protein (ESP) whilst watercress did not show any such activity. Expand
Interactions of thioglucoside glucohydrolase and epithiospecifier protein of cruciferous plants to form 1-cyanoepithioalkanes
The interactions occur across genetic lines, indicating non-specific requirements for epithiospecifier protein and thioglucoside glucohydrolase in Brassica, Crambe, Armoracia and Sinapis. Expand