Abstract
For decades, various plants have been studied as sources of biologically active compounds. Compounds with anticancer and antimicrobial properties are the most frequently desired. Cruciferous plants, including Brussels sprouts, broccoli, and wasabi, have a special role in the research studies. Studies have shown that consumption of these plants reduce the risk of lung, breast, and prostate cancers. The high chemopreventive and anticancer potential of cruciferous plants results from the presence of a large amount of glucosinolates, which, under the influence of myrosinase, undergo an enzymatic transformation to biologically active isothiocyanates (ITCs). Natural isothiocyanates, such as benzyl isothiocyanate, phenethyl isothiocyanate, or the best-tested sulforaphane, possess anticancer activity at all stages of the carcinogenesis process, show antibacterial activity, and are used in organic synthesis. Methods of synthesis of sulforaphane, as well as its natural or synthetic bifunctional analogues with sulfinyl, sulfanyl, sulfonyl, phosphonate, phosphinate, phosphine oxide, carbonyl, ester, carboxamide, ether, or additional isothiocyanate functional groups, and with the unbranched alkyl chain containing 2–6 carbon atoms, are discussed in this review. The biological activity of these compounds are also reported. In the first section, glucosinolates, isothiocyanates, and mercapturic acids (their metabolites) are briefly characterized. Additionally, the most studied anticancer and antibacterial mechanisms of ITC actions are discussed.
Highlights
Many are edible plants, such as Brussels sprouts, broccoli, radish, horse radish, cabbage, wasabi, and rocket [2,3]. These vegetables are characterized by high chemopreventive activity
GSLs are composed of three elements: β-D-thioglucose group, sulfonated oxime moiety, and side chain R, whose structures correspond to the α-amino acids used during biosynthesis (Figure 1)
Studies show that inhibition of histone deacetylase (HDAC) with SFN contribute to inhibition of the cell cycle in PC-3 cells in the G2/M phase [127], while inhibition of HDAC using benzyl isothiocyanate (BITC) causes the deactivation of NF-κB, which leads to decreased activity of cyclin D1 and, to the inhibition of the cell cycle [128]
Summary
The Brassicaceae family [1] called Cruciferae, includes more than 2000 plant species. Many are edible plants, such as Brussels sprouts, broccoli, radish, horse radish, cabbage, wasabi, and rocket [2,3]. These vegetables are characterized by high chemopreventive activity. E.g., while chewing the plants, results in the formation of a variety of glucosinolate breakdown products (Figure 2). The breakdown of GSLs initiated by enzymatic hydrolysis of the thioglucoside bond leads to the elimination of β-D-glucose and the formation of an unstable thiohydroximateO-sulfonate, which, depending on the pH, undergoes the so-called Lossen rearrangement to isothiocyanate (pH 7), or a decomposition to nitrile (pH 4). The epithiospecifier modifier protein (ESM) inhibits the formation of nitrile and favors the formation of isothiocyanates [32] (Figure 2). Detailed information about enzymatic hydrolysis of glucosinolates and the functions of specifier proteins were reviewed by Burow and Wittstock [33]
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