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Formation of volatile sulfur compounds and S-methyl-l-cysteine sulfoxide in Brassica oleracea vegetables
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Besides glucosinolates, Brassica vegetables accumulate sulfur-containing (+)-S-methyl-l-cysteine sulfoxide (SMCSO, methiin), mainly known from Allium vegetables. Such (+)-S-alk(en)yl-l-cysteine sulfoxides can degrade to volatile organosulfur compounds (VOSCs), which have been linked to health beneficial effects. In the present study, the accumulation of SMCSO and the formation of VOSCs was investigated in Brassica oleracea vegetables. SMCSO content of commercially available white and red cabbages was monitored over a three-month period and linked with the formation of VOSCs. S-Methyl methanethiosulfinate was the main VOSC released from SMCSO. Upon heating, it degraded to dimethyltrisulfide and dimethyldisulfide, which were less abundant in fresh homogenates. SMCSO made up approximately 1% of the dry matter of cabbages and the overall contents were similar in white and red cabbages (3.2-10.2 and 3.9-10.3 µmol/g fresh weight, respectively). Using proteome profiling it was shown that recovery of VOSCs correlated with abundance of two isoforms of cystine lyase.
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“Sulfides are considered to be the decomposition and thermal degradation products of methylthioproteins, catalyzed by cysteine sulfoxide lyase [100].”
From The Metabolic Pathways of Yeast and Acetic Acid Bacteria During Fruit Vinegar Fermentation and Their Influence on Flavor Development (2025) · cites this paper as [100]
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Research works printed but not linked: 42
- Akpolat, 2015, The effect of pH and temperature on cabbage volatiles during storage, Journal of Food Science, 80, S1878, 10.1111/1750-3841.12939 · DOI
- Armstrong, 1951, Thioether derivatives of cysteine and homocysteine, The Journal of Organic Chemistry, 16, 749, 10.1021/jo01145a015 · DOI
- Asemani, 2019, Allium vegetables for possible future of cancer treatment, Phytotherapy Research, 33, 3019, 10.1002/ptr.6490 · DOI
- Brady, 2014, De-novo designed library of benzoylureas as inhibitors of BCL-XL: Synthesis, structural and biochemical characterization, Journal of Medicinal Chemistry, 57, 1323, 10.1021/jm401948b · DOI
- Chin, 1993, Volatile sulfur compounds formed in disrupted tissues of different cabbage cultivars, Journal of Food Science, 58, 835, 10.1111/j.1365-2621.1993.tb09370.x · DOI
- Chin, 1994, Mechanisms of formation of volatile sulfur compounds following the action of cysteine sulfoxide lyases, Journal of Agricultural and Food Chemistry, 42, 1529, 10.1021/jf00043a026 · DOI
- Coode‐Bate, 2019, Accumulation of dietary S-methyl cysteine sulfoxide in human prostate tissue, Molecular Nutrition & Food Research, 63, 1900461, 10.1002/mnfr.201900461 · DOI
- Danner, 2015, Aboveground and belowground herbivores synergistically induce volatile organic sulfur compound emissions from shoots but not from roots, Journal of Chemical Ecology, 41, 631, 10.1007/s10886-015-0601-y · DOI
- Edmands, 2013, S-Methyl-L-cysteine sulphoxide: The Cinderella phytochemical?, Toxicology Research, 2, 11, 10.1039/C2TX20030A · DOI
- Frank, 2018, Influenceof saliva on individual in-mouth aroma release from raw cabbage (Brassica oleracea var. capitata f. rubra L.) and links to perception, Heliyon, 4, 10.1016/j.heliyon.2018.e01045 · DOI
- Hamamoto, 1986, The C-S lyases of higher plants : Isolation and properties of homogeneous cystine lyase from broccoli (Brassica oleracea var. botrytis) buds, Plant Physiology, 80, 702, 10.1104/pp.80.3.702 · DOI
- Hanschen, 2012, Characterization of products from the reaction of glucosinolate-derived isothiocyanates with cysteine and lysine derivatives formed in either model systems or broccoli sprouts, Journal of Agricultural and Food Chemistry, 60, 7735, 10.1021/jf301718g · DOI
- Hanschen, 2018, Leaching and degradation kinetics of glucosinolates during boiling of Brassica oleracea vegetables and the formation of their breakdown products, Food Chemistry, 263, 240, 10.1016/j.foodchem.2018.04.069 · DOI
- Hanschen, 2017, Isothiocyanates, nitriles, and epithionitriles from glucosinolates are affected by genotype and developmental stage in Brassica oleracea varieties, Frontiers in Plant Science, 8, 1095, 10.3389/fpls.2017.01095 · DOI
- Horie, 2006, Non-derivatized analysis of methiin and alliin in vegetables by capillary electrophoresis, Journal of Chromatography A, 1132, 337, 10.1016/j.chroma.2006.09.018 · DOI
- Kanehisa, 2016, BlastKOALA and GhostKOALA: KEGG tools for functional characterization of genome and metagenome sequences, Journal of Molecular Biology, 428, 726, 10.1016/j.jmb.2015.11.006 · DOI
- Kaspar, 2010, Protein analysis of laser capture micro-dissected tissues revealed cell-type specific biological functions in developing barley grains, Analytical and Bioanalytical Chemistry, 398, 2883, 10.1007/s00216-010-4120-y · DOI
- Kawamori, 1995, Chemoprevention of azoxymethane-induced colon carcinogenesis by dietary feeding of S-methyl methane thiosulfonate in male F344 rats, Cancer Research, 55, 4053
- Kellingray, 2021, Effects of in vitro metabolism of a broccoli leachate, glucosinolates and S-methylcysteine sulphoxide on the human faecal microbiome, European Journal of Nutrition, 60, 2141, 10.1007/s00394-020-02405-y · DOI
- Kiddle, 1999, C-S lyase activities in leaves of crucifers and non-crucifers, and the characterization of three classes of C-S lyase activities from oilseed rape (Brassica napus L.), Plant, Cell & Environment, 22, 433, 10.1046/j.1365-3040.1999.00416.x · DOI
- Kubec, 2009, Chromatographic methods for determination of S-substituted cysteine derivatives–a comparative study, Journal of Chromatography A, 1216, 6957, 10.1016/j.chroma.2009.08.032 · DOI
- Kubec, 1998, Thermal degradation of S-methylcysteine and its sulfoxides - Important flavor precursors of Brassica and Allium vegetables, Journal of Agricultural and Food Chemistry, 46, 4334, 10.1021/jf980379x · DOI
- Kubec, 2001, Gas-chromatographic determination of S-methylcysteine sulfoxide in cruciferous vegetables, European Food Research and Technology, 213, 386, 10.1007/s002170100384 · DOI
- Kyung, 1994, S-Methyl-L-cysteine sulfoxide as the precursor of methyl methanethiolsulfinate, the principal antibacterial compound in cabbage, Journal of Food Science, 59, 350, 10.1111/j.1365-2621.1994.tb06964.x · DOI
- Kyung, 1997, Antibacterial activity of heated cabbage juice, S-methyl-L-cysteine sulfoxide and methyl methanethiosulfonate, Journal of Food Science, 62, 406, 10.1111/j.1365-2621.1997.tb04013.x · DOI
- Mae, 1971, Metabolism of S-methylcysteine and its sulfoxide in chinese cabbage, Brassica pekinensis Rupr, Plant and Cell Physiology, 12, 881, 10.1093/oxfordjournals.pcp.a074692 · DOI
- Marino, 2021, An overview of registered clinical trials on glucosinolates and human health: The current situation. Frontiers, Nutrition, 8
- Marks, 1993, Effect of S-methyl cysteine sulphoxide and its metabolite methyl methane thiosulphinate, both occurring naturally in Brassica vegetables, on mouse genotoxicity, Food and Chemical Toxicology, 31, 491, 10.1016/0278-6915(93)90108-B · DOI
- Marks, 1992, S-Methylcysteine sulfoxide in Brassica vegetables and formation of methyl methanethiosulfinate from Brussels sprouts, Journal of Agricultural and Food Chemistry, 40, 2098, 10.1021/jf00023a012 · DOI
- Morris, 1956, The identification of (+)S-methyl-L-cysteine sulfoxide in plants, Journal of the American Chemical Society, 78, 1605, 10.1021/ja01589a028 · DOI
- Nakamura, 1996, S-Methyl methanethiosulfonate, bio-antimutagen in homogenates of Cruciferae and Liliaceae vegetables, Bioscience, Biotechnology, and Biochemistry, 60, 1439, 10.1271/bbb.60.1439 · DOI
- Olech, 2014, Jack bean urease inhibition by crude juices of Allium and Brassica plants, Determination of thiosulfinates. Food Chemistry, 145, 154, 10.1016/j.foodchem.2013.08.044 · DOI
- Palliyaguru, 2018, Isothiocyanates: Translating the power of plants to people, Molecular Nutrition & Food Research, 62, 1700965, 10.1002/mnfr.201700965 · DOI
- Pickering, 1967, Disproportionation of organic polysulfides, Journal of the American Chemical Society, 89, 2364, 10.1021/ja00986a021 · DOI
- Rabinkov, 1998, The mode of action of allicin: Trapping of radicals and interaction with thiol containing proteins, Biochimica et Biophysica Acta (BBA) - General Subjects, 1379, 233, 10.1016/S0304-4165(97)00104-9 · DOI · Paper page
- Rose, 2005, Bioactive S-alk(en)yl cysteine sulfoxide metabolites in the genus Allium: The chemistry of potential therapeutic agents, Natural Product Reports, 22, 351, 10.1039/b417639c · DOI
- Sønderby, 2010, Biosynthesis of glucosinolates – gene discovery and beyond, Trends in Plant Science, 15, 283, 10.1016/j.tplants.2010.02.005 · DOI
- Synge, 1956, (+)-(S-methyl-L-cysteine S-oxide) in cabbage, The Biochemical journal, 64, 252, 10.1042/bj0640252 · DOI
- Ukai, 1997, Purification and characterization of cystine lyase a from broccoli inflorescence, Bioscience, Biotechnology, and Biochemistry, 61, 1890, 10.1271/bbb.61.1890 · DOI
- Wermter, 2020, Seasonal variation of glucosinolate hydrolysis products in commercial wite and red cabbages (Brassica oleracea var. capitata), Foods, 9, 1682, 10.3390/foods9111682 · DOI
- Witzel, 2019, Identification and characterization of three epithiospecifier protein isoforms in Brassica oleracea, Frontiers in Plant Science, 10, 1552, 10.3389/fpls.2019.01552 · DOI
- Yan, 2019, Dimethyl disulfide (DMDS) as an effective soil fumigant against nematodes in China, PLOS ONE, 14, e0224456, 10.1371/journal.pone.0224456 · DOI
Cited by
Sorted by citations
Ge, Y., Wu, Y., Aihaiti, A., Wang, L., Wang, Y., Xing, J., Zhu, M., & Hong, J. (2025) · Microorganisms · doi:10.3390/microorganisms13030477 · Cited by 49
Metadata
- Authors
- Friedrich, K., Wermter, N. S., Andernach, L., Witzel, K., & Hanschen, F. S.
- Affiliations
- Leibniz Institute of Vegetable and Ornamental Crops (DE)
- Universität Hamburg (DE)
- Corresponding author
- Hanschen, Franziska S.
- Venue
- Food Chemistry
- Publisher
- Elsevier BV
- Published
- 2022-07
- Volume
- 383
- Pages
- 132544
- ISSN
- 0308-8146 (ISSN-L)
- OpenAlex
- W4214916360
- Cited by
- 41
- References
- 0
- Citations by year
- 2026: 8 · 2025: 8 · 2024: 14 · 2023: 9 · 2022: 2
- FWCI
- 4.54
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Food Chemistry (publishedVersion, cc-by-nc-nd)
- PubMed (publishedVersion)
- Funders
- Leibniz-Gemeinschaft (J16 / 2017)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Garlic and Onion Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Genomics, phytochemicals, and oxidative stress
- Life Sciences › Agricultural and Biological Sciences › Agronomy and Crop Science › Nitrogen and Sulfur Effects on Brassica
- Keywords
- volatile sulfur compounds, S-methyl-L-cysteine sulfoxide, Brassica oleracea, cabbage, red cabbage, glucosinolates, dimethyl disulfide, proteomic profiling, sulfur metabolism
- MeSH terms
- Brassica, Cysteine, Safrole, Sulfoxides, Sulfur Compounds, Vegetables
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