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Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model

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Author: Krul, C.A.M. · Humblot, C. · Philippe, C. · Vermeulen, M. · Nuenen, M. van · Havenaar, R. · Rabot, S.
Type:article
Date:2002
Institution: Centraal Instituut voor Voedingsonderzoek TNO
Source:Carcinogenesis, 6, 23, 1009-1016
Identifier: 87901
Keywords: Biology · Adult · Anticarcinogenic Agents · Biotransformation · Brassica · Colon · Cookery · Digestion · Feces · Female · Glucosinolates · Humans · Intestinal Mucosa · Kinetics · Male · Models, Biological · Time Factors

Abstract

Cruciferous vegetables, such as Brassica, which contain substantial quantities of glucosinolates, have been suggested to possess anticarcinogenic activity. Cutting and chewing of cruciferous vegetables releases the thioglucosidase enzyme myrosinase, which degrades glucosinolates to isothiocyanates and other minor metabolites. Cooking of cruciferous vegetables inactivates the myrosinase enzyme, allowing intact glucosinolates to reach the large intestine, where they can be degraded by the indigenous microflora into isothiocyanates. This local release of isothiocyanates may explain the protective effect of cruciferous vegetables on the colon epithelium. However, little is known about the amounts and identities of glucosinolate metabolites produced by the human microflora. The production of allyl isothiocyanate from sinigrin was investigated in a dynamic in vitro large-intestinal model, after inoculation with a complex microflora of human origin. Sinigrin and allyl isothiocyanate concentrations were analysed in the lumen and dialysis fluid of the model. Peak levels of allyl isothiocyanate were observed between 9 and 12 h after the addition of sinigrin. The model was first set up with a pooled and cultured human microflora, in which 1 and 4% of, respectively, 1 and 15 mM sinigrin, was converted into AITC. However, the conversion rate was remarkably higher if different individual human microflora were used. Between 10% and 30% (mean 19%) of the sinigrin was converted into allyl isothiocyanate. The results of this study suggest that allyl isothiocyanate is converted further into other, yet unknown, metabolites. Chemicals/CAS: Anticarcinogenic Agents; Glucosinolates; sinigrin, 534-69-0