Chemical Aspects of Biological Activity of Isothiocyanates and Indoles, the Products of Glucosinolate Decomposition

Dominik Kołodziejski; Izabela Koss-Mikołajczyk; Ahmad Yaman Abdin; Jacob Claus; Agnieszka Bartoszek-Pączkowska

doi:10.2174/1381612825666190701151644

Chemical Aspects of Biological Activity of Isothiocyanates and Indoles, the Products of Glucosinolate Decomposition

Abstract

There is growing evidence that cancer chemoprevention employing natural, bioactive compounds may halt or at least slow down the different stages of carcinogenesis. A particularly advantageous effect is attributed to derivatives of sulfur-organic phytochemicals, such as glucosinolates (GLs) synthesized mainly in Brassicaceae plant family. GLs are hydrolysed enzymatically to bioactive isothiocyanates (ITC) and indoles, which exhibit strong anti-inflammatory and anti-carcinogenic activity. Highly bioavailable electrophilic ITC are of particular interest, as they can react with nucleophilic groups of important biomolecules to form dithiocarbamates, thiocarbamates and thioureas. These modifications seem responsible for the chemopreventive activity, but also for genotoxicity and mutagenicity. It was documented that ITC can permanently bind to important biomolecules such as glutathione, cytoskeleton proteins, transcription factors NF-κB and Nrf2, thiol-disulfide oxidoreductases, proteasome proteins or heat shock proteins. Furthermore, ITC may also affect epigenetic regulation of gene expression, e.g. by inhibition of histone deacetylases. Some other derivatives of glucosinolates, especially indoles, are able to form covalent bonds with nucleobases in DNA, which may result in genotoxicity and mutagenicity. This article summarizes the current state of knowledge about glucosinolates and their degradation products in terms of possible interactions with reactive groups of cellular molecules.

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Authors (5)

Dominik Kołodziejski
Izabela Koss-Mikołajczyk dr inż.
Ahmad Yaman Abdin
Jacob Claus prof
Agnieszka Bartoszek-Pączkowska prof. dr hab. inż.

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License: Copyright (2019 Bentham Science)

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Category:: Articles
Type:: artykuły w czasopismach
Published in:: CURRENT PHARMACEUTICAL DESIGN no. 25, pages 1717 - 1728,
ISSN: 1381-6128
Language:: English
Publication year:: 2019
Bibliographic description:: Kołodziejski D., Koss-Mikołajczyk I., Abdin A., Claus J., Bartoszek-Pączkowska A.: Chemical Aspects of Biological Activity of Isothiocyanates and Indoles, the Products of Glucosinolate Decomposition// CURRENT PHARMACEUTICAL DESIGN -Vol. 25,iss. 15 (2019), s.1717-1728
DOI:: Digital Object Identifier (open in new tab) 10.2174/1381612825666190701151644
Verified by:: Gdańsk University of Technology