The metabolism of benzyl isothiocyanate and its cysteine conjugate in guinea-pigs and rabbits

Görler, K.; Krumbiegel, Günter; Mennicke, W. H.; Siehl, Hans Ullrich

doi:10.3109/00498258209038932

Cited by 29 publications

(16 citation statements)

References 6 publications

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“…The cyclic mercaptopyruvic acid (4-hydroxy-4-carboxy-3-benzylthiazolidin-2-thione) occurred in the urine from guinea-pigs and rabbits after the oral or intravenous administration of benzyl isothiocyanate or its cysteine metabolite. 39 In human individuals, the isothiocyanates are mainly metabolized via the mercapturic acid pathway. 40 However, to the best of our knowledge, mercaptopyruvic acid has not been observed in human intervention studies up to now, and we also did not detect it in our study.…”

Section: ■ Discussionmentioning

confidence: 99%

Glucosinolates Are Mainly Absorbed Intact in Germfree and Human Microbiota-Associated Mice

Budnowski

Hanske

Schumacher

et al. 2015

J. Agric. Food Chem.

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Chemoprotective or genotoxic effects of glucosinolates occurring in Brassica vegetables are attributed to their hydrolysis products formed upon tissue damage by plant myrosinase. Since Brassica vegetables, in which myrosinase has been heat-inactivated, still display bioactivity, glucosinolate activation has been attributed to intestinal bacteria. The aim of this study was to investigate whether this is true. Glucoraphanin (172 mg/kg body weight) and neoglucobrassicin (297 mg/kg body weight) were administered intragastrically to germ free and human microbiota associated (HMA) mice. Approximately 30% of the applied doses of glucoraphanin and neoglucobrassicin were excreted unchanged in the urine of both germ free and HMA mice. Isothiocyanates, sulforaphane, and erucin, formed from glucoraphanin, were mainly excreted as urinary N-acetyl-l-cysteine conjugates. N-Methoxyindole-3-carbinol formed from neoglucobrassicin was observed in small amounts in both germ free and HMA mice. Formation of DNA adducts from neoglucobrassicin was also independent from bacterial colonization of the mice. Hence, intestinal bacteria are involved in the bioactivation of glucosinolates in the gut, but their contribution to glucosinolate transformation in HMA mice is apparently very small.

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Section: ■ Discussionmentioning

confidence: 99%

Glucosinolates Are Mainly Absorbed Intact in Germfree and Human Microbiota-Associated Mice

Budnowski

Hanske

Schumacher

et al. 2015

J. Agric. Food Chem.

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“…These studies show that guinea pigs and rabbits do not excrete mercapturic acids during the metabolism of ITCs. The authors pointed out that these species also do not readily form mercapturic acids after administration of other types of xenobiotics [128].…”

Section: Bitc and Conjugatesmentioning

confidence: 99%

Isothiocyanates as Cancer Chemopreventive Agents: Their Biological Activities and Metabolism in Rodents and Humans

Conaway¹,

Yang²,

Chung³

2002

CDM

374

308

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Isothiocyanates (ITCs) are a group of naturally occurring compounds that occur as thioglucoside conjugates, termed glucosinolates, in plants and cruciferous vegetables such as watercress, Brussels sprouts, broccoli, cabbage, kai choi, kale, horseradish, radish and turnip. ITCs inhibit the development of tumors in many of the experimental models investigated, and are being investigated as possible chemopreventive agents for specific human cancers. The goal of this review is to provide a mechanistic understanding for the biological activities of ITCs and to relate the metabolism of ITCs to their action as chemopreventive agents. In vivo animal studies have been conducted to address issues of tissue disposition, pharmacokinetics, and metabolism of ITCs. Methods for analysis of ITCs and their metabolites in urine and plasma have been developed. The metabolism of several naturally occurring ITCs as constituents of foodstuffs or as drugs has also been investigated in human studies. Finally, based on recent epidemiological studies, the role of dietary consumption of vegetables containing ITCs in prevention of human cancers and human cancer susceptibility is discussed.

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“…While cysteine conjugates of ITCs can be absorbed intact [177,191], GSH conjugates were shown to require release of free ITC prior to absorption [187]. Diindolylmethane (DIM) and 2,3-BII, the main hydrolysis products of indole-GLS derived products were detected by De Kruif et al [160] in the liver of rats, suggesting that they are absorbed by the small intestine.…”

Section: Colonic Fermentationmentioning

confidence: 99%

Glucosinolates inBrassicavegetables: The influence of the food supply chain on intake, bioavailability and human health

Verkerk¹,

Schreiner

Krumbein

et al. 2009

Molecular Nutrition Food Res

517

424

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Glucosinolates (GLSs) are found in Brassica vegetables. Examples of these sources include cabbage, Brussels sprouts, broccoli, cauliflower and various root vegetables (e.g. radish and turnip). A number of epidemiological studies have identified an inverse association between consumption of these vegetables and the risk of colon and rectal cancer. Animal studies have shown changes in enzyme activities and DNA damage resulting from consumption of Brassica vegetables or isothiocyanates, the breakdown products (BDP) of GLSs in the body. Mechanistic studies have begun to identify the ways in which the compounds may exert their protective action but the relevance of these studies to protective effects in the human alimentary tract is as yet unproven. In vitro studies with a number of specific isothiocyanates have suggested mechanisms that might be the basis of their chemoprotective effects. The concentration and composition of the GLSs in different plants, but also within a plant (e.g. in the seeds, roots or leaves), can vary greatly and also changes during plant development. Furthermore, the effects of various factors in the supply chain of Brassica vegetables including breeding, cultivation, storage and processing on intake and bioavailability of GLSs are extensively discussed in this paper.

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The metabolism of benzyl isothiocyanate and its cysteine conjugate in guinea-pigs and rabbits

Cited by 29 publications

References 6 publications

Glucosinolates Are Mainly Absorbed Intact in Germfree and Human Microbiota-Associated Mice

Glucosinolates Are Mainly Absorbed Intact in Germfree and Human Microbiota-Associated Mice

Isothiocyanates as Cancer Chemopreventive Agents: Their Biological Activities and Metabolism in Rodents and Humans

Glucosinolates inBrassicavegetables: The influence of the food supply chain on intake, bioavailability and human health

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