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From Designer Food Formulation to Oxidative Stress Mitigation: Health-Boosting Constituents of Cabbage
Published in Megh R. Goyal, Hafiz Ansar Rasul Suleria, Ramasamy Harikrishnan, The Role of Phytoconstitutents in Health Care, 2020
Faiza Ashfaq, Masood Sadiq Butt, Ahmad Bilal, Kanza Aziz Awan, Hafiz Ansar Rasul Suleria
Numerous studies have depicted that cruciferous vegetables possess a complex combination of bioactive ingredients, minerals, and antioxidant vitamins that could scavenge ROS, ultimately improving the levels of GSH, SOD, and CAT. Besides other ingredients, the GLS-myrosinase system exists inherently in brassica vegetables, and myrosinase hydro-lyzes GLS to isothiocyanates. The myrosinase is either natively present within the compartments of plant cells or in the mammalian intestine. It is still unclear that these S-containing compounds are either responsible for lowering cholesterol levels or the synergistic effect of several antioxidants in cabbage to improve the overall antioxidant status. Recent investigation on broccoli has associated isothiocyanates and sulforaphane with cholesterol-lowering activity [96].
Phytonutrients
Published in Parimelazhagan Thangaraj, Medicinal Plants, 2018
Ranganathan Kumar, Sulaxana Kumari Chauhan, Subramanian Vijayalakshmi, Shanmugam Nadanasabapathi
Three-day-old sprouts of cultivars of certain crucifers, including broccoli and cauliflower, contain 10 to 100 times higher amounts of the aliphatic glucosinolate glucoraphanin than the corresponding mature plants (Fahey et al. 1997). Myrosinase hydrolyzes glucoraphanin to yield sulforaphane, an isothiocyanate, which induces a phase II enzyme (Zhang et al. 1992). Hence, broccoli sprouts have more desirable anticancer properties than matured vegetables (Fahey et al. 1997; Nestle 1998).
Nutrition and the Risk of Common Forms of Cancer
Published in David Heber, Zhaoping Li, Primary Care Nutrition, 2017
Dietary glucosinolates are hydrolyzed by a plant enzyme called myrosinase when the vegetable is crushed, releasing the volatile metabolites, such as isothiocyanate. These compounds travel to the liver and induce phase 2 detoxifying enzymes, including glutathione S-transferases and UDP glucuronosyl transferases (UGTs). These enzymes in the liver catalyze conjugation reactions to inactivate or detoxify exogenous carcinogens and endogenous compounds, including sex steroid hormones related to cancer development (Mansuy 2011; Navarro et al. 2011; Boddupalli et al. 2012). Indole glucosinolate hydrolysis products, such as di-indolyl methane and indole-3-carbinol, also induce both phase 1 drug metabolic and phase 2 detoxifying enzymes by direct interaction with aryl-hydrocarbon receptor (AhR) or increasing the binding affinity of AhR to xenobiotic response elements (XREs) in target genes (Navarro et al. 2011).
Glucosinolate-Enriched Fractions from Maca (Lepidium meyenii) Exert Myrosinase-Dependent Cytotoxic Effects against HepG2/C3A and HT29 Tumor Cell Lines
Published in Nutrition and Cancer, 2022
Raquely M. Lenzi, Luciano H. Campestrini, Simone C. Semprebon, Jonas A.R. Paschoal, Monique A.G. Silva, Selma F. Zawadzki-Baggio, Mário S. Mantovani, Carmen L.O. Petkowicz, Juliana B.B. Maurer
GLs are water-soluble, highly stable, and relatively nonreactive compounds (17). In the plant cells, GLs coexist with the enzyme myrosinase (MYR) in specialized compartments. The damage to plant tissue (eg., insect attack, mastication, or processing) promotes MYR-mediated hydrolysis of GLs into their bioactive derivatives (17). GLs are hydrolyzed by MYR derived from both the plant tissue (released by the mastication process) and the intestinal microbiota. Additionally, unprocessed GLs can be absorbed through the gastrointestinal mucosa (18). GL derivatives, which are volatile compounds, impart characteristic spicy taste and pungency to cruciferous vegetables. The chemical properties of the hydrolyzed products depend on the structure of the GL side chain, plant species, and reaction conditions. Isothiocyanates (ITCs), which are typically formed under neutral conditions, are reported to exert anticancer effects (19).
Bioactivation of herbal constituents: mechanisms and toxicological relevance
Published in Drug Metabolism Reviews, 2019
Although ITCs are electrophiles capable of covalently modifying proteins, they occur in plants as glucosinolates (β-thioglucoside-N-hydrosulfates, Figure 16). When the physical structure of the vegetable is damaged, for example cutting or chewing, the enzyme myrosinase (β-thioglucoside glucohydrolase) present in cruciferous vegetables comes into contact with the glucosinolate converting it to an unstable thiohydroximate O-sulfonate, which yields the electrophilic isothiocyanate via Lossen rearrangement (Figure 16). Conjugation with glutathione (GSH) is the principal metabolic pathway of ITCs which readily react with the cysteine residue in GSH through thiocarbamation, a covalent bond formation between the electrophilic carbon atom in the ITC moiety and the sulfhydryl group in GSH. Reaction of the –N=C=S group with intracellular GSH drives rapid ITC accumulation in cells as the conjugates are unstable and readily dissociate to their parent compounds. GSH conjugation of ITCs is also facilitated by human GSTs, in particular GSTs M1-1 and P1-1 (Kolm et al. 1995). The formed dithiocarbamates are typically excreted as mercapturic acids in both urine and bile. The electrophilic carbon of ITCs also reacts irreversibly with amine groups in proteins to form stable thioureas with much slower rates of reaction (Brown et al. 2009). In addition, ITCs can undergo CYP-mediated oxidative desulfuration to electrophilic isocyanates leading to the formation of S-thiocarbamate conjugates (Figure 16) (Lee 1996; Yoshigae et al. 2013).
Cruciferous Vegetable Consumption and Stomach Cancer: A Case-Control Study
Published in Nutrition and Cancer, 2020
Maia E. W. Morrison, Janine M. Joseph, Susan E. McCann, Li Tang, Hani M. Almohanna, Kirsten B. Moysich
Intake of phytochemicals has been found to be inversely associated with development of various cancers, including stomach. Of these phytochemicals, glucosinolates, which are found in cruciferous plants, are broken down by chewing, food processing, or when they are brought into contact with the plant defense enzyme, myrosinase. Isothiocyanates (ITC) are an important result of this process because they have been shown in in vitro and animal studies to have anti-carcinogenic properties, including protecting against chemically induced tumors (10,20,21), interacting with the epigenome to restore normal epigenetic landscape in malignant cells, and regulating the epigenetic machinery (22).