Goitringoitrin foods, goitrin structure
Goitrin is a sulfur-containing oxazolidine, a cyclic thiocarbamate, that reduces the production of thyroid hormones such as thyroxine It is found in cruciferous vegetables such as cabbage, brussels sprouts and rapeseed oil, and is formed by the hydrolysis of a glucosinolate: progoitrin or 2-hydroxy-3-butenyl glucosinolate The unstable isothiocyanate 2-hydroxy-3-butenyl isothiocyanate derived from the latter glucosinolate spontaneously cyclizes to goitrin, because the hydroxy group is situated in proximity to the isothiocyanate group allowing a five-membered ring to be formed Hence, the oxygen in the molecule stems from the hydroxy group of the original unstable isothiocyanate Plants containing this specific glucosinolate or glucosinolates such as glucobrassicin and sinalbin which liberate thiocyanate ion have goitrogenic potential due to the goitrin and thiocyanate they contain However, they do not seem to alter thyroid function in humans at realistic amounts in the diet
- ^ McMillan M, Spinks EA, Fenwick GR January 1986 "Preliminary observations on the effect of dietary brussels sprouts on thyroid function" Hum Toxicol 5 1: 15–9 doi:101177/096032718600500104 PMID 2419242
- ^ Lüthy J, Carden B, Friederich U, Bachmann M May 1984 "Goitrin--a nitrosatable constituent of plant foodstuffs" Experientia 40 5: 452–3 doi:101007/BF01952381 PMID 6723906
- ^ Verhoeven DT, Verhagen H, Goldbohm RA, van den Brandt PA, van Poppel G February 1997 "A review of mechanisms underlying anticarcinogenicity by brassica vegetables" Chem Biol Interact 103 2: 79–129 doi:101016/S0009-27979603745-3 PMID 9055870
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|Isothiocyanates ITC, mustard oils||
goitrin, goitrin foods, goitrin structure, goitrina, goitrins
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