Identification of 1-methoxyindolyl-3-methyl isothiocyanate as an indole glucosinolate breakdown product

Hanley, A. Bryan; Parsley, K. R.

doi:10.1016/0031-9422(90)80015-9

Cited by 32 publications

(3 citation statements)

References 3 publications

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“…As Brassica ‐vegetable‐derived isothiocyanates are usually formed under aqueous conditions, the reaction with water is one of the most important ones, especially under thermal processing conditions. Indole isothiocyanates are very labile and decompose immediately in water to produce an alcohol and a thiocyanate ion 46e. It is postulated that indole isothiocyanate decomposition proceeds via a resonance‐stabilized carbocation that is very reactive 99.…”

Section: Reactivity Of Glucosinolate Breakdown Productsmentioning

confidence: 99%

Reactivity and Stability of Glucosinolates and Their Breakdown Products in Foods

et al. 2014

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The chemistry of glucosinolates and their behavior during food processing is very complex. Their instability leads to the formation of a bunch of breakdown and reaction products that are very often reactive themselves. Although excessive consumption of cabbage varieties has been thought for long time to have adverse, especially goitrogenic effects, nowadays, epidemiologic studies provide data that there might be beneficial health effects as well. Especially Brassica vegetables, such as broccoli, radish, or cabbage, are rich in these interesting plant metabolites. However, information on the bioactivity of glucosinolates is only valuable when one knows which compounds are formed during processing and subsequent consumption. This review provides a comprehensive, in-depth overview on the chemical reactivity of different glucosinolates and breakdown products thereof during food preparation.

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Section: Reactivity Of Glucosinolate Breakdown Productsmentioning

confidence: 99%

Reactivity and Stability of Glucosinolates and Their Breakdown Products in Foods

et al. 2014

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“…Da Isothiocyanate aus Brassica ‐Arten normalerweise unter wässrigen Bedingungen entstehen, ist ihre Reaktion mit Wasser besonders wichtig, vor allem bei der thermischen Verarbeitung. Indolisothiocyanate sind sehr labil und zerfallen in Wasser sofort unter Bildung eines Alkohols und des Thiocyanat‐Ions 46e. Man nimmt an, dass der Zerfall von Indolisothiocyanaten über ein resonanzstabilisiertes Carbokation verläuft, das sehr reaktiv ist 99.…”

Section: Reaktivität Der Abbauprodukte Von Glucosinolatenunclassified

Reaktivität und Stabilität von Glucosinolaten und ihren Abbauprodukten in Lebensmitteln

et al. 2014

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Die Chemie von Glucosinolaten und ihre Reaktionen während der Lebensmittelverarbeitung sind sehr komplex. Aufgrund ihrer Instabilität entsteht eine ganze Reihe von Abbau‐ und Reaktionsprodukten, die häufig ebenfalls reaktiv sind. Obwohl der übermäßige Genuss von Kohlsorten lange Zeit mit nachteiligen, vor allem goitrogenen (kropfbildenden) Wirkungen in Verbindung gebracht wurde, weisen aktuelle Ergebnisse aus epidemiologischen Studien auch auf potenziell positive Gesundheitseffekte hin. Insbesondere Gemüse aus der Familie der Kreuzblütler (Brassicaceae) wie Broccoli, Rettich oder Kohl sind reich an diesen interessanten pflanzlichen Metaboliten. Informationen zur Bioaktivität von Glucosinolaten sind aber nur dann von Nutzen, wenn man weiß, welche Verbindungen bei der Verarbeitung gebildet und anschließend verzehrt werden. Dieser Aufsatz bietet eine umfassende und detaillierte Übersicht über die chemische Reaktivität verschiedener Glucosinolate und ihrer Abbauprodukte während der Lebensmittelzubereitung.

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“…In conclusion, 1-MIM GL is a potent genotoxicant in in vitro systems and animal models. Two activation mechanisms, including specific enzymes that mediate the activation, have been identified in in vitro systems (Scheme 1): (i) 1-MIM GL is activated by plant myrosinase to become an ultimate mutagen, presumably 1-MIM isothiocyanate, identified as a short-lived intermediate in the myrosinase-mediated conversion of 1-MIM GL to 1-MIM-OH [55,56]. (ii) The second activation pathway starts from 1-MIM-OH and is mediated by human SULT1A1 in the presence of its co-substrate, 3 ′ -phosphoadenosine-5 ′ -phosphosulphate.…”

Section: Introductionmentioning

confidence: 99%

Formation of DNA Adducts by 1-Methoxy-3-indolylmethylalcohol, a Breakdown Product of a Glucosinolate, in the Mouse: Impact of the SULT1A1 Status—Wild-Type, Knockout or Humanised

Glatt,

Weißenberg,

Ehlers

et al. 2024

IJMS

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We previously found that feeding rats with broccoli or cauliflower leads to the formation of characteristic DNA adducts in the liver, intestine and various other tissues. We identified the critical substances in the plants as 1-methoxy-3-indolylmethyl (1-MIM) glucosinolate and its degradation product 1-MIM-OH. DNA adduct formation and the mutagenicity of 1-MIM-OH in cell models were drastically enhanced when human sulfotransferase (SULT) 1A1 was expressed. The aim of this study was to clarify the role of SULT1A1 in DNA adduct formation by 1-MIM-OH in mouse tissues in vivo. Furthermore, we compared the endogenous mouse Sult1a1 and transgenic human SULT1A1 in the activation of 1-MIM-OH using genetically modified mouse strains. We orally treated male wild-type (wt) and Sult1a1-knockout (ko) mice, as well as corresponding lines carrying the human SULT1A1-SULT1A2 gene cluster (tg and ko-tg), with 1-MIM-OH. N2-(1-MIM)-dG and N6-(1-MIM)-dA adducts in DNA were analysed using isotope-dilution UPLC-MS/MS. In the liver, caecum and colon adducts were abundant in mice expressing mouse and/or human SULT1A1, but were drastically reduced in ko mice (1.2–10.6% of wt). In the kidney and small intestine, adduct levels were high in mice carrying human SULT1A1-SULT1A2 genes, but low in wt and ko mice (1.8–6.3% of tg-ko). In bone marrow, adduct levels were very low, independently of the SULT1A1 status. In the stomach, they were high in all four lines. Thus, adduct formation was primarily controlled by SULT1A1 in five out of seven tissues studied, with a strong impact of differences in the tissue distribution of mouse and human SULT1A1. The behaviour of 1-MIM-OH in these models (levels and tissue distribution of DNA adducts; impact of SULTs) was similar to that of methyleugenol, classified as “probably carcinogenic to humans”. Thus, there is a need to test 1-MIM-OH for carcinogenicity in animal models and to study its adduct formation in humans consuming brassicaceous foodstuff.

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Identification of 1-methoxyindolyl-3-methyl isothiocyanate as an indole glucosinolate breakdown product

Cited by 32 publications

References 3 publications

Reactivity and Stability of Glucosinolates and Their Breakdown Products in Foods

Reactivity and Stability of Glucosinolates and Their Breakdown Products in Foods

Reaktivität und Stabilität von Glucosinolaten und ihren Abbauprodukten in Lebensmitteln

Formation of DNA Adducts by 1-Methoxy-3-indolylmethylalcohol, a Breakdown Product of a Glucosinolate, in the Mouse: Impact of the SULT1A1 Status—Wild-Type, Knockout or Humanised

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