Identification of new derivatives of sinigrin and glucotropaeolin produced by the human digestive microflora using 1H NMR spectroscopy analysis of in vitro incubations.
One- and two-dimensional (1)H NMR spectroscopy were used to study the biotransformation of two dietary glucosinolates, sinigrin (SIN), and glucotropaeolin (GTL) by the human digestive microflora in vitro. The molecular structures of the new metabolites issued from the aglycone moiety of the glucosinolate were identified, and the modulation of carbon metabolism was studied by quantifying bacterial metabolites issued from the xenobiotic incubation in the presence or absence of a source of free glucose. Unambiguously and for the first time, it was shown that SIN and GTL were transformed quantitatively into allylamine and benzylamine, respectively. The comparison of the kinetics of transformation of SIN and GTL with and without glucose clearly showed that the presence of glucose did not modify either the nature of the metabolites or the rate of transformation of the glucosinolates (complete degradation within 30 h). The main end products of the glucose moiety of glucosinolates were characteristic of anaerobic carbon metabolism in the digestive tract (acetate, lactate, ethanol, propionate, formate, and butyrate) and similar to those released from free glucose. This work represents the first application of (1)H NMR spectroscopy to the study of xenobiotic metabolism by the human digestive microflora, demonstrating allyl- and benzylamine production from glucosinolates. Whether these amines are produced in vivo from dietary glucosinolates remains to be established. This would reduce the availability of other glucosinolate metabolites, notably cancer-protective isothiocyanates.
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Laboratoire Synthèse Electrosynthèse et Etude de Systèmes à Intérêt Biologique, Unité Mixte Recherche 6504 du Centre National de la Recherche Scientifique, Université Blaise Pascal, 63177 Aubière Cedex, France.
Elfoul
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Delort
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Rabot
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D000328:Adult; D001937:Brassica; D004064:Digestive System / Q000378:metabolism / Q000382:microbiology; D005243:Feces / Q000737:chemistry* / Q000382:microbiology*; D005961:Glucosinolates / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D006877:Hydroxamic Acids / Q000737:chemistry / Q000378:metabolism*; D017879:Isothiocyanates; D007700:Kinetics; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D011522:Protons; D013863:Thioglucosides / Q000737:chemistry / Q000378:metabolism*
D005961:Glucosinolates; D006877:Hydroxamic Acids; D017879:Isothiocyanates; D011522:Protons; D013863:Thioglucosides; C060321:glucotropeolin; C010330:sinigrin