Diverse Excretion Pathways of Benzyl Glucosinolate in Humans after Consumption of Nasturtium (<i>Tropaeolum majus</i> L.)—A Pilot Study

Kühn, Carla; Kupke, Franziska; Baldermann, Susanne; Klopsch, Rebecca; Lamy, Evelyn; Hornemann, Silke; Pfeiffer, Andreas F. H.; Schreiner, Monika; Rohn, Sascha

doi:10.1002/mnfr.201800588

Cited by 14 publications

(11 citation statements)

References 59 publications

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“…Although likely by a different mechanism, protein binding to lysine and cysteine residues in vivo is also known for ITCs. [19] Nevertheless, for ETNs also alternative routes of metabolism might occur that were not detectable by the present study. For example similar to simple nitriles, which are metabolized by cytochrome CYP2E1 which yields finally cyanide ions, [20] ETNs might be metabolized by CYPs as well.…”

Section: Discussioncontrasting

confidence: 57%

Metabolism and Recovery of Epithionitriles from Glucosinolates—A Human Intervention Study

Hoffmann

Baldermann

Wiesner-Reinhold

et al. 2022

Molecular Nutrition Food Res

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Scope: Epithionitriles can be main glucosinolate hydrolysis products inBrassica vegetables such as cabbage or pak choi. Here, for the first time, the bioavailability and metabolism of longer-chain epithionitriles (C4-C5) is studied in a human intervention study. Methods and results: After consumption of a white cabbage or pak choi sprouts beverage, rich in either 1-cyano-2,3-epithiopropane (CETP) or 1-cyano-3,4-epithiobutane (CETB) and 1-cyano-4,5-epithiopentane (CETPent), blood and urine samples of nine participants are taken and the metabolites are analyzed. The corresponding N-acetyl-S-(cyano-(methylthio)alkyl)-l-cysteine metabolites are identified and quantified by isotope dilution method using UHPLC-TOF-MS. The standards for N-acetyl-S-(cyano-(methylthio)alkyl)-l-cysteine metabolites from CETB andCETPent are synthesized for the first time and their structure confirmed by NMR spectroscopy. In contrast to the metabolites of CETP and CETPent, the expected metabolite of CETB is not detectable. The recoveries of the CETP and CETPent metabolites are 28 ± 9% for CETP and 12 ± 3% for CETPent in urine within 24 h. Conclusion: CETP and CETPent are quickly uptaken, metabolized via the mercapturic acid pathway, and excreted via urine, while for CETB the corresponding metabolite is not detectable. Therefore, an additional metabolization pathway seems to exist.

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Section: Discussioncontrasting

confidence: 57%

Metabolism and Recovery of Epithionitriles from Glucosinolates—A Human Intervention Study

Hoffmann

Baldermann

Wiesner-Reinhold

et al. 2022

Molecular Nutrition Food Res

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“…Subsequently, TFA was added and the samples frozen at -80°C. The preparation of serum samples (300 µL serum and 100 µL TFA) was conducted as described by Kühn et al (37). The frozen samples were thawed, vortexed (1 min) and centrifuged (4°C, 10 min, 20.854 x g).…”

Section: Human Food Intervention and Preparation Of Blood Serum Samples For Determination Of Aitc Mercapturic Acid Metabolitesmentioning

confidence: 99%

Allyl Isothiocyanate: A TAS2R38 Receptor-Dependent Immune Modulator at the Interface Between Personalized Medicine and Nutrition

et al. 2021

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Understanding individual responses to nutrition and medicine is of growing interest and importance. There is evidence that differences in bitter taste receptor (TAS2R) genes which give rise to two frequent haplotypes, TAS2R38-PAV (functional) and TAS2R38-AVI (non-functional), may impact inter-individual differences in health status. We here analyzed the relevance of the TAS2R38 receptor in the regulation of the human immune response using the TAS2R38 agonist allyl isothiocyanate (AITC) from Brassica plants. A differential response in calcium mobilization upon AITC treatment in leucocytes from healthy humans confirmed a relevance of TAS2R38 functionality, independent from cation channel TRPV1 or TRPA1 activation. We further identified a TAS2R38-dependence of MAPK and AKT signaling activity, bactericidal (toxicity against E. coli) and anti-inflammatory activity (TNF-alpha inhibition upon cell stimulation). These in vitro results were derived at relevant human plasma levels in the low micro molar range as shown here in a human intervention trial with AITC-containing food.

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“…The cultivation was done according to standard procedures for Brassica vegetables, including fertilization, irrigation, and plant protection. After 10 weeks, leaves were harvested and immediately frozen at −50 • C, freeze-dried, and milled to a fine powder [26]. A part of the homogenized material was analysed for the GLS content and the other part applied into the bread dough.…”

Section: Plant Materialsmentioning

confidence: 99%

Determination of Isothiocyanate-Protein Conjugates in a Vegetable-Enriched Bread

Krell

Cvancar

Poloczek

et al. 2021

Foods

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Vegetables of the plant order Brassicales are believed to have health-promoting properties, as they provide high contents of glucosinolates (GLS) and deriving from these, enzymatically and heat-induced breakdown products, such as isothiocyanates (ITC). Besides their positive physiological effects, ITC are electrophilic and can undergo reactions with food components such as proteins. Following the trend of improving traditional food products with GLS-rich ingredients, interactions of ITC with proteins can diminish the properties of both components—protein’s value and functionality as well as ITC’s bioactivity. In vegetable-enriched bread, where cresses (Lepidium sativum L. or Tropaeolum majus L.) are added to the initial dough, together with benzyl cyanide, benzyl isothiocyanate (BITC) is formed during the baking process. The aim of the present study was to investigate the possible migration behavior of the GLS breakdown products and the formation of ITC-wheat protein conjugates. After the baking process, the breads’ proteins were enzymatically hydrolyzed, and the ITC-amino acid conjugates analyzed using a LC-ESI-MS/MS methodology. In all samples, BITC-protein conjugates were detected as thiourea derivatives, while formation of dithiocarbamates could not be detected. The study showed that GLS and their breakdown products such as ITC migrate into the surrounding food matrix and undergo reactions with proteins, which could in turn lead to modified protein properties and reduce the bioavailability of ITC and lysine.

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Diverse Excretion Pathways of Benzyl Glucosinolate in Humans after Consumption of Nasturtium (Tropaeolum majus L.)—A Pilot Study

Cited by 14 publications

References 59 publications

Metabolism and Recovery of Epithionitriles from Glucosinolates—A Human Intervention Study

Metabolism and Recovery of Epithionitriles from Glucosinolates—A Human Intervention Study

Allyl Isothiocyanate: A TAS2R38 Receptor-Dependent Immune Modulator at the Interface Between Personalized Medicine and Nutrition

Determination of Isothiocyanate-Protein Conjugates in a Vegetable-Enriched Bread

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