Brassica vegetables as sources of epithionitriles: Novel secondary products formed during cooking.

Abstract:

:The epithionitriles, 1-cyano-2,3-epithiopropane, in particular, and 1-cyano-3,4-epithiobutane, are important, but yet underestimated glucosinolate hydrolysis products that are released instead of the cancer preventative isothiocyanates in Brassica vegetables, such as cabbage, broccoli, or pak choi. Here, we characterized the reactivity of 1-cyano-2,3-epithiopropane under aqueous heat treatment conditions and compared our findings to those of the related epithionitriles 1-cyano-3,4-epithiobutane and 1-cyano-4,5-epithiopentane. In contrast to the other epithionitriles, 1-cyano-2,3-epithiopropane is highly reactive. As a result, 2-aminothiophene and dimeric 1,4-dithiane-2,5-diacetonitrile were identified as main products and a reaction mechanism is proposed. Formation of 2-aminothiophene was also observed in cooked white cabbage samples. Moreover, three novel compounds were identified as derivatives of the related epithionitriles. The results imply that apart from isothiocyanates, process-derived compounds should be considered in regards to cancer preventative Brassica vegetable related bioactivity.

journal_name

Food Chem

journal_title

Food chemistry

authors

Hanschen FS,Kaufmann M,Kupke F,Hackl T,Kroh LW,Rohn S,Schreiner M

doi

10.1016/j.foodchem.2017.10.124

subject

Has Abstract

pub_date

2018-04-15 00:00:00

pages

564-569

eissn

0308-8146

issn

1873-7072

pii

S0308-8146(17)31771-5

journal_volume

245

pub_type

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