(+)-(<i>S</i>-Methyl-<scp>l</scp>-cysteine <i>S</i>-oxide) in cabbage

Synge, R. L. M.; Wood, Jo

doi:10.1042/bj0640252

Cited by 125 publications

(43 citation statements)

References 20 publications

(12 reference statements)

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“…S-Methylcysteine and its sulphoxide occur in the non-protein nitrogen fraction of various plants (Morris & Thompson, 1955;Synge & Wood, 1956; Thompson, Morris & Zacharius, 1956), and there is evidence for its presence in the mycelium of Neurospora crassa (Ragland & Liverman, 1956). Furthermore, Wolff, Black & Downey (1956) demonstrated its enzymic synthesis in baker's yeast from methanethiol and serine.…”

Section: Discussionmentioning

confidence: 99%

Ability of S-Methyl-L-cysteine to Annul the Inhibition of Yeast Growth by L-Ethionine and by S-Ethyl-L-cysteine

Maw¹

1961

Journal of General Microbiology

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SUMMARYThe inhibition of growth of a brewer's yeast and four other yeasts by L-ethionine, and the annulment of the inhibition by L-methionine were examined. S-Methyl-L-cysteine, DL-methionine sulphoxide and DL-a-amino-n-butyric acid were also able to decrease the growth inhibition. At a fivefold molar concentration, S-methylcysteine annulled completely the effect of ethionine on the brewer's yeast. S-Ethyl-L-cysteine was ineffective and in certain conditions it acted as a growth inhibitor; this inhibition was annulled by methionine and by S-methylcysteine.

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Section: Discussionmentioning

confidence: 99%

Ability of S-Methyl-L-cysteine to Annul the Inhibition of Yeast Growth by L-Ethionine and by S-Ethyl-L-cysteine

Maw¹

1961

Journal of General Microbiology

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“…with authentic S-methylcysteine and S-ethoxycarbonylcysteine respectively. Oxidation of the compound represented by spot 4 with hydrogen peroxide, according to Synge & Wood (1956), gave a product (spot 2) that was unequivocally identified as S-methylcysteine S-oxide by analysis and mixed m.p. with an authentic specimen, obtained by similar oxidation of commercial S-methylcysteine.…”

Section: Resultsmentioning

confidence: 99%

“…Oxidation with hydrogen peroxide according to Synge & Wood (1956) yielded S-methylcysteine S-oxide, which crystallized from aq. ethanol in white prisms, m.p.…”

Section: Isolation Of S-methylcysteinementioning

confidence: 99%

Interaction of N-alkyl-N-nitrosourethanes with thiols

Schoental

Rive

1965

Biochemical Journal

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1. The interaction at room temperature of thiols (cysteine and certain of its derivatives, and glutathione) with N-alkyl-N-nitrosourethanes and with diazomethane gave complicated mixtures of products. 2. S-Methylcysteine and S-ethoxycarbonylcysteine, the main products of the reaction between cysteine and N-methyl-N-nitrosourethane, were isolated and unequivocally identified. Paper-chromatographic and other evidence was used for the identification of several other components of the mixtures of products obtained. 3. S-Methyl derivatives and their methyl esters were the common products formed from the thiol compounds with both N-methyl-N-nitrosourethane and with diazomethane. 4. The esters were unstable and hydrolysed readily. 5. S-Ethoxycarbonyl derivatives, the primary products of the reaction of the thiols with N-alkyl-N-nitrosourethanes, isomerized to the respective N-ethoxycarbonyl derivatives when the pH increased above 7.0; the migration of the ethoxycarbonyl group from S to N was particularly easy with cysteine, probably owing to the spatial proximity of the amino group. 6. It is suggested that the non-enzymic reactions in vitro of thiols with both N-methyl-N-nitrosourethane and diazomethane may represent models for events in vivo and might help in the studies of the carcinogenic process.

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“…The homogenized supernatant was centrifuged at 100 000g for 30 min. The amount of radioactive CO 2 produced from [1][2][3][4][5][6][7][8][9][10][11][12][13][14] C]ornithine was assayed to estimate the ODC activity. Statistical analysis Statistical analysis of data was performed by employing Student's t test.…”

Section: Immunohistochemical Staining Of Gst-p and Pcnamentioning

confidence: 99%

“…[12][13][14] S-Allylcysteine (SAC), an analog of SMC, has been found to inhibit experimental colon carcinogenesis in mice. 15) Cysteine esters have protective potential against toxicity induced by sulfur mustard in cultured rodent lung slices.…”

mentioning

confidence: 99%

Inhibitory Effects of S‐Methylcysteine and Cysteine on the Promoting Potential of Sodium Phenobarbital on Rat Liver Carcinogenesis

Vijayaraghavan

Wanibuchi

Takada

et al. 2000

Japanese Journal of Cancer Research

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The effects of S-methylcysteine (SMC) and cysteine on the promotion stages of rodent hepatocarcinogenesis in a medium-term bioassay previously developed by Ito were examined. Initiation was induced by a single dose of diethylnitrosamine (DEN), followed by dietary administration of the promoter sodium phenobarbital (NaPB) 2 weeks later, for 6 weeks. Partial hepatectomy was conducted on all the animals at week 3. Inhibitory potential was evaluated by analyzing two markers of carcinogenesis, namely numbers of glutathione S-transferase placental form (GST-P)-positive foci, and proliferating cell nuclear antigen (PCNA). In addition, the level of ornithine decarboxylase (ODC), one of the rate-limiting enzymes of polyamine metabolism induced by promoters, was analyzed. SMC and cysteine induced significant reduction in the areas of GST-P-positive foci. A significant reduction in the PCNA index was observed in the entire liver as well as in GST-Ppositive areas. SMC also induced down-regulation of the ODC enzyme activity. Thus, SMC and cysteine were found to inhibit the promotion stage of DEN-induced hepatocarcinogenesis. No cocarcinogenic effects were evident on administration of either of these chemicals with NaPB.

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(+)-(S-Methyl-l-cysteine S-oxide) in cabbage

Cited by 125 publications

References 20 publications

Ability of S-Methyl-L-cysteine to Annul the Inhibition of Yeast Growth by L-Ethionine and by S-Ethyl-L-cysteine

Ability of S-Methyl-L-cysteine to Annul the Inhibition of Yeast Growth by L-Ethionine and by S-Ethyl-L-cysteine

Interaction of N-alkyl-N-nitrosourethanes with thiols

Inhibitory Effects of S‐Methylcysteine and Cysteine on the Promoting Potential of Sodium Phenobarbital on Rat Liver Carcinogenesis

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