Initial and Final Products, Nitriles, and Ascorbigens Produced in Myrosinase-Catalyzed Hydrolysis of Indole Glucosinolates

Agerbirk, Niels; Olsen, Carl Erik; Sørensen, Hilmer

doi:10.1021/jf9708498

Cited by 99 publications

(107 citation statements)

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“…Concerning the indol-3-ylmethylglucosinolates, these compounds may be transformed into a complex range of different products upon myrosinase catalyzed hydrolysis including indol-3-ylcarbinoles, indol-3-ylacetonitriles, ascorbigens and various indol-3-yloligomers [Agerbirk et al, 1998;Bones & Rossiter, 2006; Buskov et al, 2000 a, b; Jeffery & Aray, 2009]. Although indol-3-ylmethylglucosinolates are quantitatively dominating compounds in broccoli, only limited information is available on the potential biological effects of the individual indolyl derivatives [Bonnesen et al, 1999;Jensen et al, 1991;Loft et al, 1992;Vang et al, 2001].…”

Section: Unauthenticatedmentioning

confidence: 99%

“…Concerning the indol-3-ylmethylglucosinolates, these compounds may be transformed into a complex range of different products upon myrosinase catalyzed hydrolysis including indol-3-ylcarbinoles, indol-3-ylacetonitriles, ascorbigens and various indol-3-yloligomers [Agerbirk et al, 1998 Glucosinolates may also be transformed by non-enzymatic reactions, which can take place under reducing conditions and acidic pH, leading to the production of nitriles, or thionamides for 2-hydroxy substituted glucosinolates [Bellostas et al, 2008b;Bones & Rossiter, 2006].…”

Section: Effects Of Novel Processing Techniques On Glucosinolates Andmentioning

confidence: 99%

“…dithiocarbamates and thioureas [Bellostas et al, 2007[Bellostas et al, , 2008[Bellostas et al, a,b, 2009. It is therefore likely that the results from many studies concerning the low recovery of sulforaphane found in Brassica autolysates also could be explained by a further reaction of the isothiocyanate with nucleophiles to form dithiocarbamates or thioureas [Andersen et al, 2010a].Concerning the indol-3-ylmethylglucosinolates, these compounds may be transformed into a complex range of different products upon myrosinase catalyzed hydrolysis including indol-3-ylcarbinoles, indol-3-ylacetonitriles, ascorbigens and various indol-3-yloligomers [Agerbirk et al, 1998;Bones & Rossiter, 2006; Buskov et al, 2000 a, b; Jeffery & Aray, 2009]. Although indol-3-ylmethylglucosinolates are quantitatively dominating compounds in broccoli, only limited information is available on the potential biological effects of the individual indolyl derivatives [Bonnesen et al, 1999;Jensen et al, 1991;Loft et al, 1992;Vang et al, 2001].…”

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confidence: 99%

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Effects of Novel Processing Techniques on Glucosinolates and Membrane Associated Myrosinases in Broccoli

Frandsen¹,

Markedal²,

Martı́n-Belloso³

et al. 2014

Pol. J. Food Nutr. Sci.

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longed shelf-life by inactivation of micro-organisms and enzymes. HP/HT can at temperatures above 50 o C lead to pasteurization using pressure levels from 250-500 MPa [Wilson et al., 2008], while sterilization can be obtained with HP at temperatures higher than 70 o C . Focus is thus on the application of HP in combination with high temperatures (HT), which may lead to tissue compression, cell wall breakage and cell membrane disruption, depending on the HP and HT levels as well as the type of vegetable or fruit that are treated [Michel & Autio, 2002]. In the present study, where broccoli has been processed, the food quality is particularly connected with the enzyme-substrate (myrosinase--glucosinolate) system, where the different types of non-enzymatic and enzymatic catalyzed hydrolysis products give rise to effects from being health promoting to affecting the taste and odor [Hansen et al., 1995[Hansen et al., , 1997 Jeffery & Aray, 2009].PEF is considered a non-thermal treatment, which can lead to pasteurization at ambient temperatures using electrical field strengths of 20-30 kV/cm, and short pulses of 1-10 µs [Mosqueda-Melgar et al., 2008]. Application of short electric pulses may result in pore formation in cell membranes, and depending on the treatment intensity, time, electric field and pulse energy the membrane permeabilisation High pressure/high temperature (HP/HT) and pulsed electric field (PEF) treatment of food are among the novel processing techniques considered as alternatives to conventional thermal food processing. Introduction of new processing techniques with fast and gentle processing steps may reveal new possibilities for preservation of healthy bioactive compounds in processed food. However, effects on various food components due to autolysis and fast reactions prior to the applied HP/HT or PEF need to be considered as the total contribution of processing steps affects the obtained food quality. The present experiments were performed on broccoli (Brassica oleracea var. Italica) florets, purée and juice. Specific focus was given to effects of HP/HT and PEF processing on the content of glucosinolates and activities of myrosinase isoenzymes (EC.3.2.1.147) in the broccoli preparations. Certain conditions applied in HP/HT processing of broccoli florets were able to maintain a high level of intact glucosinolates. Treatment at 700 MPa and 20°C for 10 min was found to inactivate myrosinase activity, but also pressure treatments at 300 MPa and 20°C were able to maintain a high level of intact glucosinolates present in the untreated broccoli florets. PEF processing of broccoli purée and juice showed that the myrosinase activities resulted in nearly total glucosinolate transformations as result of autolysis during puréeing and juice making prior to the PEF processing. These data demonstrated that insight into potential effects on myrosinase activities from application of PEF processing implies specific focus on the sample steps preceding the PEF processing. Processing of broccoli and autolysis reaction...

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Section: Unauthenticatedmentioning

confidence: 99%

“…Concerning the indol-3-ylmethylglucosinolates, these compounds may be transformed into a complex range of different products upon myrosinase catalyzed hydrolysis including indol-3-ylcarbinoles, indol-3-ylacetonitriles, ascorbigens and various indol-3-yloligomers [Agerbirk et al, 1998 Glucosinolates may also be transformed by non-enzymatic reactions, which can take place under reducing conditions and acidic pH, leading to the production of nitriles, or thionamides for 2-hydroxy substituted glucosinolates [Bellostas et al, 2008b;Bones & Rossiter, 2006].…”

Section: Effects Of Novel Processing Techniques On Glucosinolates Andmentioning

confidence: 99%

mentioning

confidence: 99%

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Effects of Novel Processing Techniques on Glucosinolates and Membrane Associated Myrosinases in Broccoli

Frandsen¹,

Markedal²,

Martı́n-Belloso³

et al. 2014

Pol. J. Food Nutr. Sci.

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“…ABG formation is strongly dependent on the pH and the already formed ABG remains relatively stable at pH 4-5 characteristics of fermented cabbage products (Aleksandrova et al 1992). ABG is the most abundant indole GLS breakdown product in sauerkraut (Ciska and Pathak 2004;Agerbirk et al 1998), a plant food product that has been widely consumed for centuries.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Determination of Ascorbigen in Sauerkrauts

et al. 2011

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Ascorbigen (ABG), 2-C-(indol-3-yl)methyl-α-Lxylo-hex-3-ulofuranosono-1,4-lactone, was synthesised and its structure and purity was confirmed by means of 1 H NMR and 13 C NMR spectra and HPLC-PDA, respectively. The electrochemical behaviour of ABG was studied by cyclic voltammetry (CV) method for pH within the range of 3.0-7.0 and further characterisation was performed by differential pulse voltammetry (DPV) at pH 5.0. Voltammetric studies of ABG at glassy carbon electrode showed one irreversible oxidation peak (centred at E p =0.950 V for pH 5.0). The anodic peak current potential related to the irreversible oxidation of ABG was shifted towards more positive potentials with decreasing pH values. The linear response between concentration of ABG within the range of 0.08-0.75 mM and recorded current was observed. The DPV method was shown to be more sensitive when compared to the CV method. ABG showed a significant reducing activity provided by CV, whilst the antioxidant activity of ABG against O 2 −• was negligible. Electrochemical behaviour of ABG standard was applied successfully for the quantification of natural ABG in sauerkrauts by DPV and HPLC-CoulArray methods. Based on the developed analytical methods, ABG content increased during natural fermentation of cabbage at 0.5% and 1.5% NaCl levels, and results were comparable with those found in the literature.

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“…GC, LC and HPLC techniques for determination of glucosinolates and glucosinolate degradation products require in most cases more or less time consuming sample preparation steps prior to the chromatographic separation [3,5,14,[27][28][29]. Micellar electrokinetic capillary chromatography (MECC) has also been developed as a method of analysis for determination of glucosinolates, desulphoglucosinolates [30,31] and some of the glucosinolate degradation products, such as OZTs and nitriles [32][33][34]. There is however, no GC, HPLC or HPCE method described up to date for the simultaneous determination of glucosinolates and their degradation products.…”

Section: Introductionmentioning

confidence: 99%

Micellar electrokinetic capillary chromatography—Synchronous monitoring of substrate and products in the myrosinase catalysed hydrolysis of glucosinolates

Bellostas¹,

Sørensen²,

Sørensen³

2006

Journal of Chromatography A

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A micellar electrokinetic capillary chromatography (MECC) method has been developed for monitoring the myrosinase catalysed hydrolysis of 2-hydroxy substituted glucosinolates and the simultaneous formation of the corresponding degradation products (oxazolidine-2-thiones (OZTs) and nitriles). Glucosibarin ((2R)-2-hydroxy-2-phenylethylglucosinolate) was chosen as the model glucosinolate owing to the difficulties in determining hydrolysis rates of this type of substrates in traditional UV-assays. The method was afterwards validated with glucobarbarin ((2S)-2-hydroxy-2-phenylethylglucosinolate) and progoitrin ((2R)-2-hydroxybut-3-enylglucosinolate). Aromatic glucosinolates without a 2-hydroxy group in their side chains, such as glucotropaeolin (benzylglucosinolate) and gluconasturtiin (phenethylglucosinolate) were also tested. Formation of the glucosinolate hydrolysis products was monitored simultaneously at 206 nm and 230 nm. This allowed estimation of the extinction coefficient of the OZT derived from glucosibarin, which was found to be 18,000 M −1 cm −1 and 12,000 M −1 cm −1 at 206 nm and 230 nm, respectively. The developed method has limit of detection of 0.04 mM and 0.06 mM and limit of quantification of 0.2 mM and 0.3 mM for the glucosibarin derived OZT and nitrile, respectively. Linearity of the glucosinolate concentration was examined at six concentration levels from 2.5 mM to 100 mM and at 206 nm a straight line (R 2 = 0.9996) was obtained. The number of theoretical plates (N) at the optimal system conditions was 245,000 for the intact glucosibarin, 264,000 for the OZT and 252,000 for the nitrile.

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Initial and Final Products, Nitriles, and Ascorbigens Produced in Myrosinase-Catalyzed Hydrolysis of Indole Glucosinolates

Cited by 99 publications

References 36 publications

Effects of Novel Processing Techniques on Glucosinolates and Membrane Associated Myrosinases in Broccoli

Effects of Novel Processing Techniques on Glucosinolates and Membrane Associated Myrosinases in Broccoli

Electrochemical Determination of Ascorbigen in Sauerkrauts

Micellar electrokinetic capillary chromatography—Synchronous monitoring of substrate and products in the myrosinase catalysed hydrolysis of glucosinolates

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