Epithiospecifier protein activity in broccoli: The link between terminal alkenyl glucosinolates and sulphoraphane nitrile

Williams, David J.; Critchley, Christa; Pun, Sharon; Nottingham, Stephen F.; O’Hare, T.J.

doi:10.1016/j.phytochem.2008.09.018

Cited by 71 publications

(58 citation statements)

References 58 publications

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“…However, Williams et al . () found an opposite result in broccoli sprouts. It showed that the myrosinase activity rose to the highest at day 2 and then decreased.…”

Section: Discussionmentioning

confidence: 97%

Effects of abscisic acid on glucosinolate content, isothiocyanate formation and myrosinase activity in cabbage sprouts

Wang

Yang

Guo

et al. 2015

Int J of Food Sci Tech

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Effects of abscisic acid (ABA) on glucosinolate content, isothiocyanate formation and myrosinase activity in cabbage sprouts were investigated. Subsequently, their distributions in different organs were evaluated. ABA (50 lmol L À1 ) significantly increased glucosinolate content, isothiocyanate formation and myrosinase activity by 72.65%, 268.15% and 67.69%, respectively, in 5-day-old sprouts. Application of ABA alleviated the decrease rate of glucosinolate content and increased the myrosinase activity during germination. Besides, isothiocyanate formation rapidly increased after germinating for 3 days. The glucosinolate content and isothiocyanate formation reduced by 46.51% and 38.01%, respectively, in fluridon (Flu)-treated sprouts. Cotyledon of ABA-treated sprouts had the highest glucosinolate content and isothiocyanate formation, indicating that ABA was necessary to enhance the isothiocyanate formation in cabbage sprouts by increasing glucosinolate content and myrosinase activity.

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“…However, Williams et al . () found an opposite result in broccoli sprouts. It showed that the myrosinase activity rose to the highest at day 2 and then decreased.…”

Section: Discussionmentioning

confidence: 97%

Effects of abscisic acid on glucosinolate content, isothiocyanate formation and myrosinase activity in cabbage sprouts

Wang

Yang

Guo

et al. 2015

Int J of Food Sci Tech

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“…During the initial sprout growth phase in broccoli, ESP activity was shown to decrease and ITC formation to increase (Williams et al, 2008). In contrast, in further developmental stages, similar results to our study were reported.…”

Section: Discussionmentioning

confidence: 99%

Isothiocyanates, Nitriles, and Epithionitriles from Glucosinolates Are Affected by Genotype and Developmental Stage in Brassica oleracea Varieties

2017

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Vegetables of the Brassica oleracea group, such as broccoli, cauliflower, and cabbage, play an important role for glucosinolate consumption in the human diet. Upon maceration of the vegetable tissue, glucosinolates are degraded enzymatically to form volatile isothiocyanates, nitriles, and epithionitriles. However, only the uptake of isothiocyanates is linked to the cancer-preventive effects. Thus, it is of great interest to evaluate especially the isothiocyanate formation. Here, we studied the formation of glucosinolates and their respective hydrolysis products in sprouts and fully developed vegetable heads of different genotypes of the five B. oleracea varieties: broccoli, cauliflower as well as white, red, and savoy cabbages. Further, the effect of ontogeny (developmental stages) during the head development on the formation of glucosinolates and their respective hydrolysis products was evaluated at three different developmental stages (mini, fully developed, and over-mature head). Broccoli and red cabbage were mainly rich in 4-(methylsulfinyl)butyl glucosinolate (glucoraphanin), whereas cauliflower, savoy cabbage and white cabbage contained mainly 2-propenyl (sinigrin) and 3-(methylsulfinyl)propyl glucosinolate (glucoiberin). Upon hydrolysis, epithionitriles or nitriles were often observed to be the main hydrolysis products, with 1-cyano-2,3-epithiopropane being most abundant with up to 5.7 μmol/g fresh weight in white cabbage sprouts. Notably, sprouts often contained more than 10 times more glucosinolates or their hydrolysis products compared to fully developed vegetables. Moreover, during head development, both glucosinolate concentrations as well as hydrolysis product concentrations changed and mini heads contained the highest isothiocyanate concentrations. Thus, from a cancer-preventive point of view, consumption of mini heads of the B. oleracea varieties is recommended.

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“…However, the cancer-preventing effects from these vegetables are strongly associated to their ability to release ITC3641. As many Brassica vegetables comprise ESP that ultimately leads to EPT and nitrile formation21, ESP activity, and thus, EPT and nitrile formation changes upon plant development4243. Moreover, ESP transcripts, and thus levels, can be induced by herbivore feeding19.…”

Section: Discussionmentioning

confidence: 99%

Optimizing isothiocyanate formation during enzymatic glucosinolate breakdown by adjusting pH value, temperature and dilution in Brassica vegetables and Arabidopsis thaliana

Hanschen

Oliviero

Schreiner

et al. 2017

Sci Rep

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Consumption of glucosinolate-rich Brassicales vegetables is associated with a decreased risk of cancer with enzymatic hydrolysis of glucosinolates playing a key role. However, formation of health-promotingisothiocyanates is inhibited by the epithiospecifier protein in favour of nitriles and epithionitriles. Domestic processing conditions, such as changes in pH value, temperature or dilution, might also affect isothiocyanate formation. Therefore, the influences of these three factors were evaluated in accessions of Brassica rapa, Brassica oleracea, and Arabidopsis thaliana. Mathematical modelling was performed to determine optimal isothiocyanate formation conditions and to obtain knowledge on the kinetics of the reactions. At 22 °C and endogenous plant pH, nearly all investigated plants formed nitriles and epithionitriles instead of health-promoting isothiocyanates. Response surface models, however, clearly demonstrated that upon change in pH to domestic acidic (pH 4) or basic pH values (pH 8), isothiocyanate formation considerably increases. While temperature also affects this process, the pH value has the greatest impact. Further, a kinetic model showed that isothiocyanate formation strongly increases due to dilution. Finally, the results show that isothiocyanate intake can be strongly increased by optimizing the conditions of preparation of Brassicales vegetables.Brassicales plants, including Arabidopsis thaliana, broccoli, cabbage and pak choi contain glucosinolates (GLSs). These sulphur-containing secondary plant metabolites not only play an important role in the plant's defense against biotic stressors, but also affect the taste of these vegetables and contribute to human health 1 . To date, a total of 130 GLSs have been identified that can be subdivided according to the structure of their variable side chain into the group of aliphatic, aromatic or indole GLS 2 . These plant metabolites are stored in the plant vacuole or in specialized S-cells 3 , but upon cell disruption, they encounter the endogenous GLS-hydrolysing enzyme myrosinase, a β-d-thioglucosidase, and the GLSs will be hydrolysed to release isothiocyanates (ITCs), nitriles and epithionitriles (EPTs) 4 . Due to their electrophilicity, GLSs in general and ITCs in particular act as effective deterrents against a multitude of pathogens as these compounds have antifungal, antimicrobial as well as insecticidal properties [5][6][7] . For humans, ITCs, such as the 4-(methylsulphinyl)butyl ITC (4MSOB-ITC), exert a multitude of health beneficial effects, including antimicrobial, antiinflammatory, antithrombotic and chemopreventive effects [8][9][10]

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Epithiospecifier protein activity in broccoli: The link between terminal alkenyl glucosinolates and sulphoraphane nitrile

Cited by 71 publications

References 58 publications

Effects of abscisic acid on glucosinolate content, isothiocyanate formation and myrosinase activity in cabbage sprouts

Effects of abscisic acid on glucosinolate content, isothiocyanate formation and myrosinase activity in cabbage sprouts

Isothiocyanates, Nitriles, and Epithionitriles from Glucosinolates Are Affected by Genotype and Developmental Stage in Brassica oleracea Varieties

Optimizing isothiocyanate formation during enzymatic glucosinolate breakdown by adjusting pH value, temperature and dilution in Brassica vegetables and Arabidopsis thaliana

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