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Antioxidant Activity of Edible Isothiocyanates

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Lipid Oxidation in Food and Biological Systems

Abstract

Naturally occurring isothiocyanates (ITCs), products of hydrolysis of glucosinolates (GSLs), attract great attention due to their well-defined indirect antioxidant and antitumor properties, which come as a result of their ability to regulate transcription factors, signaling pathways, cell cycle and apoptosis. Majority of studies on antioxidant activity of ITCs, in particular of those present in Brassica vegetables (sulforaphane, sulforaphene, erucin), indicate that some health-promoting effects might be connected rather with their indirect antioxidant mechanism of action. In this chapter several aspects of chemical and biological activity of ITCs and some parent GSLs are presented, with emphasis on chemical structure, reactivity of isothiocyanate moiety (–NCS) and the role of side chain during reactions with the reactive oxygen species and with model radicals used in common antioxidant assays. The literature survey indicates that at ambient temperatures ITCs are preventive antioxidants removing hydroperoxides and they are not radical trapping agents. However, chain-breaking character can be observed at elevated temperatures during oxidation of bulk phase lipids.

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Notes

  1. 1.

    Main abbreviations and acronyms: ABTS/ABTS+•, radical cation formed from 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic) acid; DPPH•, 2,2-diphenyl-1-picrylhydrazyl radical; ERN, erucin; ERS, erysolin; FRAP, ferric reducing antioxidant power; GL, glucosinolate(s); GSL-ERN, glucoerucin; GSL-RPS, glucoraphasatin; GSL-SFE, glucoraphenin; GSL-SFN, glucoraphanin; HAT: hydrogen atom transfer; ITC, isothiocyanate(s), ORAC, oxygen radical absorbance capacity; ROS, reactive oxygen species; RPS, raphasatin; SFE, sulforaphene; SFN, sulforaphane; SOD, superoxide dismutase; TEAC, Trolox Equivalent Antioxidant Capacity; TOSC, total oxidant scavenging capacity.

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Acknowledgements

Financial support from the National Science Centre, Poland (NCN grant OPUS No. 2018/31/B/ST4/02354 and NCN grant PRELUDIUM No. 2014/15/N/ST5/02939) is gratefully acknowledged.

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Authors and Affiliations

  1. Faculty of Chemistry, University of Warsaw, Pasteura 1, Warsaw, Poland

    Jakub Cedrowski & Grzegorz Litwinienko

  2. Department of Molecular Biophysics, Division of Radiobiology, Faculty of Biology and Environmental Protection, University of Lodz, Pomorska 141/143, Lodz, Poland

    Jacek Grebowski

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  1. Jakub Cedrowski
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  2. Jacek Grebowski
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  3. Grzegorz Litwinienko
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Correspondence to Grzegorz Litwinienko .

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  1. Facultad de Química, Dpto Química Física, Universidad de Vigo, Vigo, Spain

    Carlos Bravo-Diaz

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Cedrowski, J., Grebowski, J., Litwinienko, G. (2022). Antioxidant Activity of Edible Isothiocyanates. In: Bravo-Diaz, C. (eds) Lipid Oxidation in Food and Biological Systems. Springer, Cham. https://doi.org/10.1007/978-3-030-87222-9_13

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