Chapter Six - Glucosinolates: Molecular structure, breakdown, genetic, bioavailability, properties and healthy and adverse effects

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Abstract

Glucosinolates are a large group of plant secondary metabolites with nutritional effects and biologically active compounds. Glucosinolates are mainly found in cruciferous plants such as Brassicaceae family, including common edible plants such as broccoli (Brassica oleracea var. italica), cabbage (B. oleracea var. capitata f. alba), cauliflower (B. oleracea var. botrytis), rapeseed (Brassica napus), mustard (Brassica nigra), and horseradish (Armoracia rusticana). If cruciferous plants are consumed without processing, myrosinase enzyme will hydrolyze the glucosinolates to various metabolites, such as isothiocyanates, nitriles, oxazolidine-2-thiones, and indole-3-carbinols. On the other hand, when cruciferous are cooked before consumption, myrosinase is inactivated and glucosinolates could be partially absorbed in their intact form through the gastrointestinal mucosa. This review paper summarizes the glucosinolate molecular breakdown, their genetic aspects from biosynthesis to precursors, their bioavailability (assimilation, absorption, and elimination of these molecules), their sensory properties, identified healthy and adverse effects, as well as the impact of processing on their bioavailability.

Section snippets

Glucosinolate molecular structure

Glucosinolates (GSLs) or mustard oil glucosides are secondary metabolites synthesized by numerous species in the order Capparales, which includes agriculturally important crop plants of the Brassicaceae family (also known as cruciferous, because of the shape arrangement of the four petals of the flower) (Barba et al., 2016; Bell and Wagstaff, 2014, Bell and Wagstaff, 2017; Wittstock & Halkier, 2002). GSLs are anions formed in a generic chemical structure (Fig. 1) by thiohydroximate-O-sulfonate

Genetic aspects of glucosinolates

Despite the great interest aroused by GSLs, due to their possible uses as enhancers of the defense mechanisms of crop plants (agricultural products) in different situations of stress, and despite the growing information that is being gathered about them, their extensive variety (> 200 different structures of GSLs are known) makes it difficult to decrypt the biosynthesis mechanism of each of them completely (Frerigmann & Gigolashvili, 2014).

Bioavailability of glucosinolates

To describe the concentration of a given compound or its metabolite at a target site, the term bioavailability was defined by the Food and Drug Administration (FDA) as “the rate and extent to which a therapeutic moiety is absorbed and becomes available to the site of drug action.” When it comes to the bioavailability of a substance that does not need to be absorbed into the bloodstream, it is simply defined as “the rate and extent to which the active moiety becomes available at the site of

Metabolism in producing plants

As mentioned above, GSLs have a fundamental role in the defense of plants belonging to the order Brassicales (Agerbirk et al., 2018), that is why normally their elimination of the biological material is through the fulfillment of its defense function, that is, through the chain of reactions that make possible its breakdown in different active metabolites. Once the stress situation occurs, being it abiotic or induced by any living organism, GSLs and enzymes with β-thioglucosidase glucohydrolase

Sensory properties of glucosinolates

Once the main function of GSLs has been specified, clarified and explained as phytoprotector secondary metabolites against threats from a wide range of natures, this revision collects other additional properties that these compounds possess, and that contribute to the interest they awaken, since they make GSLs products unique and potentially useful for different uses and in different areas of investigation.

Obviously, the possibility of transforming them into future drugs or possible therapeutic

Bioactivities of GSLs

While it is true that there is great information about the classification, structures, location, and even about some metabolic pathways of the GSLs, their possible beneficial effects on health have been left aside. However, these compounds possess certain properties that make them a possible and novel therapeutic tool. Therefore, in the last decade, more attention has been paid to GSLs in this aspect, demonstrating that a shift in their defensive role is possible, so that they can offer

The fate of glucosinolates during processing of vegetables from Brassica species

Mainly, the health-beneficial effects of GSLs are attributed to their hydrolytic products, ITCs. Nevertheless, their formation depends on a wide variety of plant-intrinsic factors, such as the concentration of GSLs and the activities of myrosinases, and on numerous extrinsic postharvest factors, such as storage, industrial processing conditions, domestic preparation, mastication, and digestion (Barba et al., 2016; Oliviero, Verkerk, & Dekker, 2018).

Main conclusions and future perspectives

It is well known that a regular consumption of vegetables from Brassica species is associated with several beneficial biological activities caused by the action of the breakdown products of GSLs. Anticarcinogenic effects might be the most aforementioned propriety, but recent studies have found other beneficial activities of GSLs, including regulatory functions in inflammation and stress response, antioxidant activities, and even direct antimicrobial properties. Future studies will undoubtedly

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