In vivo formation and bioavailability of isothiocyanates from glucosinolates in broccoli as affected by processing conditions

Oliviero, Teresa; Verkerk, Ruud; Vermeulen, Martijn; Dekker, Matthijs

doi:10.1002/mnfr.201300894

Cited by 46 publications

(49 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

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

Self Cite

101

View full text Add to dashboard Cite

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]

show abstract

Section: Discussionmentioning

confidence: 99%

“…Moreover, during cooking, GLS content of vegetables often decreases due to leaching effects35. Thus, thermal processing often reduces ITC formation and uptake3637. Ingested intact GLS, however, can also be degraded by human microbial myrosinases in the colon, and subsequently, ITC can be formed38.…”

mentioning

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

Self Cite

101

View full text Add to dashboard Cite

show abstract

“…However, although research shows direct evidence for GRP hydrolysis ex vivo and in vivo to bioactive SFN by cecal microbiota, SFN is only found in trace amounts [10]. Comparatively inactive nitriles [11,12], not bioactive ITC, are typically reported as products of microbial GSL hydrolysis ex vivo, as reviewed in [3], and ingestion of cooked broccoli typically provides only about one tenth the amount of SFN as that from raw broccoli hydrolyzed by plant myrosinase during digestion [13,14,15]. These findings suggest that if hydrolysis to SFN by microbiota could be enhanced, consumers might obtain greater health benefits from cooked broccoli.…”

Section: Introductionmentioning

confidence: 99%

Dietary Broccoli Alters Rat Cecal Microbiota to Improve Glucoraphanin Hydrolysis to Bioactive Isothiocyanates

et al. 2017

View full text Add to dashboard Cite

Broccoli consumption brings many health benefits, including reducing the risk of cancer and inflammatory diseases. The objectives of this study were to identify global alterations in the cecal microbiota composition using 16S rRNA sequencing analysis and glucoraphanin (GRP) hydrolysis to isothiocyanates ex vivo by the cecal microbiota, following different broccoli diets. Rats were randomized to consume AIN93G (control) or different broccoli diets; AIN93G plus cooked broccoli, a GRP-rich powder, raw broccoli, or myrosinase-treated cooked broccoli. Feeding raw or cooked broccoli for four days or longer both changed the cecal microbiota composition and caused a greater production of isothiocyanates ex vivo. A more than two-fold increase in NAD(P)H: quinone oxidoreductase 1 activity of the host colon mucosa after feeding cooked broccoli for seven days confirmed the positive health benefits. Further studies revealed that dietary GRP was specifically responsible for the increased microbial GRP hydrolysis ex vivo, whereas changes in the cecal microbial communities were attributed to other broccoli components. Interestingly, a three-day withdrawal from a raw broccoli diet reversed the increased microbial GRP hydrolysis ex vivo. Findings suggest that enhanced conversion of GRP to bioactive isothiocyanates by the cecal microbiota requires four or more days of broccoli consumption and is reversible.

show abstract

“…In most humans, the extent of activation of myrosinase (released by mastication of broccoli cells) within the human oral cavity and the rapid release of sulforaphane from glucoraphanin determine the overall bioavailability of sulforaphane from broccoli [8]. Free luminal sulforaphane is taken up by enterocytes in the jejunum of the small intestine [9] and in the proximal large intestine [5].…”

mentioning

confidence: 99%

A Glance at… Broccoli, glucoraphanin, and sulforaphane

Glade

Meguid²

2015

Nutrition

View full text Add to dashboard Cite

In vivo formation and bioavailability of isothiocyanates from glucosinolates in broccoli as affected by processing conditions

Abstract: For the first time, the effect of residual MYR activity on isothiocyanate bioavailability was systematically and quantitatively studied. Processing conditions have a large effect on the kinetics and bioavailability of isothiocyanates from broccoli.

Cited by 46 publications

References 30 publications

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

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

Dietary Broccoli Alters Rat Cecal Microbiota to Improve Glucoraphanin Hydrolysis to Bioactive Isothiocyanates

A Glance at… Broccoli, glucoraphanin, and sulforaphane

Contact Info

Product

Resources

About