Products of Acidic Hydrolysis of S-Methyl-L-cysteine Sulfoxide; the Isolation of Methyl Methanethiolsulfonate, and Mechanism of the Hydrolysis<sup>1</sup>

Ostermayer, F.; Tarbell, D. S.

doi:10.1021/ja01499a070

Cited by 43 publications

(28 citation statements)

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“…The candidate metabolites SMCSO and NAc-SMCSO were synthesised following previously published methods [37][38][39] . The synthetic standards were subjected to 1 H-NMR, 2D HSQC and HMBC analysis, and spiked into human urine in order to confirm identity.…”

Section: Structural Identification Of Candidate Biomarkersmentioning

confidence: 99%

Identification of Human Urinary Biomarkers of Cruciferous Vegetable Consumption by Metabonomic Profiling

et al. 2011

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Consumption of cruciferous vegetables (CVs) is inversely correlated to many human diseases including cancer (breast, lung, and bladder), diabetes, cardiovascular and neurological disease.Presently, there are no readily measureable biomarkers of CV consumption and intake of CVs has relied on dietary recall. Here, biomarkers of CV intake were identified in the urine of 20 healthy Caucasian adult males using 1 H-NMR spectroscopy with multivariate statistical modeling. The study was separated into three phases of 14 days: a run-in period with restricted CV consumption (phase I); a high CV phase where participants consumed 250g/day of both broccoli and Brussels sprouts (phase II); a wash-out phase with a return to restricted CV consumption (phase III). Each study participant provided a complete cumulative urine collection over 48 hours at the end of each phase; a spot urine (U0), 0-10 hours (U0-10), 10-24 hours (U10-24) and 24-48 hours (U24-48) urine samples. Urine samples obtained after consumption of CV were differentiated from low CV diet samples by 4 singlet 1 H-NMR spectroscopic peaks, two of which were identified as S-methyl-L-cysteine sulphoxide (SMCSO) and N-acetyl-Smethyl-L-cysteine sulphoxide (NAc-SMCSO). These stable urinary biomarkers of CV consumption will facilitate future assessment of CV in nutritional population screening and dietary intervention studies and may correlate to population health outcomes.

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Section: Structural Identification Of Candidate Biomarkersmentioning

confidence: 99%

Identification of Human Urinary Biomarkers of Cruciferous Vegetable Consumption by Metabonomic Profiling

et al. 2011

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“…Identification during the present study of dipropyl disulfide and diallyl disulfide in addition to climethyl disulfide suggests the coexistence of the corresponding sulfoxides. Ostermayer and Tarbell ( 1960) described the hydrolysis of S-methyl-L-cysteine sulfoxicle by the equation 0 t 4CH,SCH,CHNH,COOH+2H,O--+ 0 CH+CH,+(CH,), S,+4NHs+4CH,COCOOH 0 A parallel reaction doubtless occurs in the formation of dipropyl and diallyl disulfides in cabbage. If this reaction is a general one and truly accounts for the major portion of the organic sulfur of cabbage (Synge and Wood, 1955), the origin of the remaining disulfides listed in Table 1 may be due to the presence of sulfoxides not yet reported as occurring naturally.…”

Section: The Volatile Sulfur Components Of Cabbagementioning

confidence: 99%

The Volatile Sulfur Components of Cabbage^a

Bailey

Bazinet

Driscoll

et al. 1961

Journal of Food Science

105

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Naturally occurring volatile sulfur compounds in cabbage have been identified by mass spectrometry and gas chromatography. Twenty sulfur compounds are reported of which five are isothiocyanates, five sulfides, nine disulfides and one trisulfide. Two additional isothiocyanates and one trisulfide are tentatively reported. The method of mass spectral analysis is described for representative members of these sulfur compounds. Gas chromatography of fresh, dehydrated and rehydrated cabbage clearly shows the presence of ally1 isothiocyanate in fresh cabbage and its regeneration by enzymatic action in dehydrated. cabbage. The identification of five isothiocyanates reveals the presence of corresponding thioglucosides from which the isothiocyanates are released by enzymatic hydrolysis. Similarly corresponding reactions leading to the formation of sulfides are discussed.

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“…SMCSO is known to be hydrolyzed into dimethyl disulfide (DMDS) and MMTSO 2 on heating (Fig. 1, Ostermayer and Tarbell, 1960).…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of Heated Cabbage Juice, S‐Methyl‐L‐Cysteine Sulfoxide and Methyl Methanethiosulfonate

Kyung

Han

Fleming

1997

Journal of Food Science

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Autoclaved cabbage juice was inhibitory to growth of Staphylococcus aureus. S-Methyl-L-cysteine sulfoxide (SMCSO), autoclaved either together with or separately from nutrient broth, also inhibited the growth of S. aureus, but inhibition was greater when SMCSO was autoclaved separately. Methyl methanethiosulfonate (MMTSO 2 ), a thermal breakdown product of SMCSO, completely inhibited growth of S. aureus at 10 ppm. MMTSO 2 was formed in both autoclaved samples of cabbage juice and aqueous solution of SMCSO. Thus, evidence indicates that the bacterial inhibitory activity in autoclaved cabbage juice was due to heatinduced formation of MMTSO 2 from SMCSO.

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Products of Acidic Hydrolysis of S-Methyl-L-cysteine Sulfoxide; the Isolation of Methyl Methanethiolsulfonate, and Mechanism of the Hydrolysis¹

Cited by 43 publications

References 0 publications

Identification of Human Urinary Biomarkers of Cruciferous Vegetable Consumption by Metabonomic Profiling

Identification of Human Urinary Biomarkers of Cruciferous Vegetable Consumption by Metabonomic Profiling

The Volatile Sulfur Components of Cabbage^a

Antibacterial Activity of Heated Cabbage Juice, S‐Methyl‐L‐Cysteine Sulfoxide and Methyl Methanethiosulfonate

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Products of Acidic Hydrolysis of S-Methyl-L-cysteine Sulfoxide; the Isolation of Methyl Methanethiolsulfonate, and Mechanism of the Hydrolysis1

Cited by 43 publications

References 0 publications

Identification of Human Urinary Biomarkers of Cruciferous Vegetable Consumption by Metabonomic Profiling

Identification of Human Urinary Biomarkers of Cruciferous Vegetable Consumption by Metabonomic Profiling

The Volatile Sulfur Components of Cabbagea

Antibacterial Activity of Heated Cabbage Juice, S‐Methyl‐L‐Cysteine Sulfoxide and Methyl Methanethiosulfonate

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Products of Acidic Hydrolysis of S-Methyl-L-cysteine Sulfoxide; the Isolation of Methyl Methanethiolsulfonate, and Mechanism of the Hydrolysis¹

The Volatile Sulfur Components of Cabbage^a