Determination of N-acetyl-S-(N-alkylthiocarbamoyl)-l-cysteine, a principal metabolite of alkyl isothiocyanates, in rat urine

Mennicke, W. H.; Král, Tomáš; Krumbiegel, Günter; Rittmann, N.

doi:10.1016/0378-4347(87)80020-8

Cited by 37 publications

(23 citation statements)

References 9 publications

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“…This mechanism is the mercapturic acid pathway of isothiocyanate metabolism (Figure 3). Mercapturic acid derivatives of dietary isothiocyanates have been detected as major urinary metabolites in rats and human subjects after consumption of glucosinolates [11,12] .…”

Section: Biosynthesis and Metabolismmentioning

confidence: 99%

Are isothiocyanates potential anti-cancer drugs?

2009

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Isothiocyanates are naturally occurring small molecules that are formed from glucosinolate precursors of cruciferous vegetables. Many isothiocyanates, both natural and synthetic, display anticarcinogenic activity because they reduce activation of carcinogens and increase their detoxification. Recent studies show that they exhibit anti-tumor activity by affecting multiple pathways including apoptosis, MAPK signaling, oxidative stress, and cell cycle progression. This review summarizes the current knowledge on isothiocyanates and focuses on their role as potential anti-cancer agents.

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Section: Biosynthesis and Metabolismmentioning

confidence: 99%

Are isothiocyanates potential anti-cancer drugs?

2009

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“…Each isothiocyanate yields a separate N-acetyl-cysteine conjugate, also known as a mercapturic acid, in urine. N-Acetyl cysteine conjugates were analyzed by modification of methods developed for analysis of rat urine (18). Four ml urine/duplicate were analyzed.…”

Section: Chemical Analysismentioning

confidence: 99%

Hydrolysis of Glucosinolates to Isothiocyanates after Ingestion of Raw or Microwaved Cabbage by Human Volunteers

Rouzaud¹,

Young²,

Duncan³

2004

Cancer Epidemiology, Biomarkers &Amp; Prevention

127

109

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Cabbage contains the glucosinolate sinigrin, which is hydrolyzed by myrosinase to allyl isothiocyanate. Isothiocyanates are thought to inhibit the development of cancer cells by a number of mechanisms. The effect of cooking cabbage on isothiocyanate production from glucosinolates during and after their ingestion was examined in human subjects. Each of 12 healthy human volunteers consumed three meals, at 48-h intervals, containing either raw cabbage, cooked cabbage, or mustard according to a cross-over design. At each meal, watercress juice, which is rich in phenethyl isothiocyanate, was also consumed to allow individual and temporal variation in postabsorptive isothiocyanate recovery to be measured. Volunteers recorded the time and volume of each urination for 24 h after each meal. Samples of each urination were analyzed for N-acetyl cysteine conjugates of isothiocyanates as a measure of entry of isothiocyanates into the peripheral circulation. Excretion of isothiocyanates was rapid and substantial after ingestion of mustard, a source of preformed allyl isothiocyanate. After raw cabbage consumption, allyl isothiocyanate was again rapidly excreted, although to a lesser extent than when mustard was consumed. On the cooked cabbage treatment, excretion of allyl isothiocyanate was considerably less than for raw cabbage, and the excretion was delayed. The results indicate that isothiocyanate production is more extensive after consumption of raw vegetables but that isothiocyanates still arise, albeit to a lesser degree, when cooked vegetables are consumed. The lag in excretion on the cooked cabbage treatment suggests that the colon microflora catalyze glucosinolate hydrolysis in this case.

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“…The limited available data on aqueous stability suggests that some of the mercapto-conjugates of phenylethylisothiocyanate and sulforaphane degrade at pH 7.4 at 37 • C [12,17] indicating a potential problem with stability. Another restricting factor in developing quantitative analysis of the mercapto-conjugates has been the lack of commercial availability of authentic standards, although methods for their synthesis are available in the literature [11,18].…”

Section: Introductionmentioning

confidence: 98%

“…Mennicke et al [11,12] first measured isothiocyanate conjugates (N-acetylcysteine conjugates) in rat urine by thin layer chromatography and subsequently developed the first quantitative method to indirect analyse the metabolites of isothiocyanates using the reaction of released alkyl isothiocyanates with n-butylamine to form corresponding di-substituted thioureas which were then quantified by HPLC. A similar approach was used by Zhang et al [13] to develop a cyclocondensation reaction of de-conjugated isothiocyanates with 1,2-benzenedithiol to yield 1,3-benzodithiole-2-thione, which can be detected by U.V.…”

Section: Introductionmentioning

confidence: 99%

“…While these methods are specific and sensitive they are limited to only one type of isothiocyanate conjugate (N-acetylcysteine conjugates). There are no methods reported for the quantitative determination of the mercapturic acid metabolites of sulforaphane and iberin in plasma, with previous analytical methods either being unsuitable or unable to detect the metabolites of sulforaphane and iberin in human plasma [12,[14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

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