The Structures of Sinigrin and Sinalbin; An Enzymatic Rearrangement

Ettlinger, Martin G.; Lundeen, Allan J.

doi:10.1021/ja01597a090

Cited by 158 publications

(41 citation statements)

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“…during food preparation, mastication or injury by predators such as insects) the enzyme is released and catalyses their hydrolysis to yield isothiocyanates principally, and also glucose and sulphate. The reaction involves an initial hydrolysis of the β-thioglucoside linkage with release of β--glucose [2]. The resultant thiohydroxamate intermediate (for which spectroscopic evidence has been obtained) releases sulphate and then undergoes a non-enzymic intramolecular Lossen rearrangement to give rise to isothiocyanates, as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

An unusual case of ‘uncompetitive activation’ by ascorbic acid: purification and kinetic properties of a myrosinase from Raphanus sativus seedlings

Shikita

Fahey

Golden

et al. 1999

Biochemical Journal

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Myrosinase (thioglucoside glucohydrolase ; EC 3.2.3.1) is a plant enzyme that hydrolyses glucosinolates, principally to isothiocyanates. Myrosinase was purified to homogeneity in good yield from 8-day-old seedlings of Raphanus sati us (daikon) using a four-step procedure involving chromatographies on anion exchange, hydrophobic Phenyl-Sepharose, gel filtration and concanavalin A-Sepharose. In order to stabilize the enzyme and to avoid excessive peak broadening during chromatography, 30 % (v\v) glycerol was added to dialysis and chromatography buffers. The purified enzyme was eluted as a single peak from a gelfiltration sizing column with an apparent molecular mass of 120 kDa. The enzyme was resolved into two subunits with molecular masses of 61 and 62 kDa by SDS\PAGE. Ascorbic acid activated the purified enzyme more than 100-fold. The V max and K m values for the hydrolysis of allyl glucosinolate (sinigrin) were 2.06 µmol\min per mg of protein and 23 µM in the absence of ascorbate and 280 µmol\min per mg of protein and 250 µM in

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Section: Introductionmentioning

confidence: 99%

An unusual case of ‘uncompetitive activation’ by ascorbic acid: purification and kinetic properties of a myrosinase from Raphanus sativus seedlings

Shikita

Fahey

Golden

et al. 1999

Biochemical Journal

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“…From the chemical aspect, glucosinolates are the substituted esters of thio-amino acids with the following chemical structure (Ettlinger 1956):…”

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confidence: 99%

The role and effects of glucosinolates of Brassica species - a review

Zukalova¹,

Vasak²

2002

PLANT SOIL ENVIRON

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Glucosinolates are the substituted esters of thio amino acids and their synthesis is based on the corresponding amino acids. Methionine and cysteine are the natural donors in the case of the Brassica plants and L-tryptophane in the indole glucosinolates, respectively. In Brassica genus, alkenyl glucosinolates are mostly present and their content and composition differ as far as the development stage and the part of the plant are concerned. The indole glucosinolates are present in a minority level. Their role of sulphur supply is questioned by their very low content between 2% in the beginning of vegetation and 0.1% in its end. Glucosinolates are discussed mostly from the aspect of their anti-nutrition, anti-microbial, anti-fungicidal, and anti-bacterial effects and as being natural bio-fumigants. Their decomposition products have the mentioned properties. The products originate by prepared passive protection by the two-component system. From the aspect of these properties, it is useful to divide them into the following three groups according to the characters of their decomposition products. The first group (I.), whose hydrolysis in the neutral and alkaline environment creates iso-thiocyanates. These bioactive compounds form the natural protection of the plant with bio-fumigatory effects particularly. Their anti-nutritive effects can be compensated by iodine, contrary to the second group (II.). This group is created by hydroxy-glucosinolates, whose decomposition products -iso-thio-cyanates -are not stable and they cycle while producing substituted 2-oxazolidinethione (goitrine -VTO). These glucosinolates represent a serious problem in feed industry since the VTO has a strong goitrogenic property. The third group (III.) -glucosinolates containing the indole group or the benzene ring (Sinalbin), create thio-cyanates during their hydrolysis. The role of indole glucosinolates has not been completely clarified so far. Their anti-carcinogenic effects are studied and they fulfil the role of an active protection.

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“…3. HPLC chromatogram of the standard solution of 4MTB-GSL NH 4 The conditions of HPLC analysis were as follows. Eluent: acetonitrile 65% and water 35% (V/V) containing 2.5 mM TDAB; Flow rate: 1.5 mL / min; Column temperature: 35°C; Column: Shiseido Capcellpak C8 UG120, particle size 5 µm, i.d.…”

Section: Resultsmentioning

confidence: 99%

“…However, the direct analytical method for 4MTB-GSL in Japanese radish has not been reported. Trifluoroacetate as paired ion reagent would degrade GSLs rapidly under the low pH character because GSLs are hydrolysed in strong acid solution 4 .…”

Section: Introductionmentioning

confidence: 99%

A Chromatographic Method for Separating and Identifying Intact 4-Methylthio-3-Butenyl Glucosinolate in Japanese Radish (Raphanus sativus L.)

Ito¹,

Horie²

2008

JARQ

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To isolate and measure intact 4-methylthio-3-butenyl glucosinolate (4MTB-GSL) in Japanese radish, we applied a paired ion chromatography method that uses tetradecylammonium ions (TDA) as counter ions. 4MTB-GSL was isolated as ammonium salts from the root of a Japanese radish and identified on the basis of myrosinase treatment, aglycon detection, negative fast atom bombardment (FAB)-mass spectra, and a UV spectrum. The linearity of the prepared standard solution and recovery of that added to Japanese radish extracts were high.

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The Structures of Sinigrin and Sinalbin; An Enzymatic Rearrangement

Cited by 158 publications

References 1 publication

An unusual case of ‘uncompetitive activation’ by ascorbic acid: purification and kinetic properties of a myrosinase from Raphanus sativus seedlings

An unusual case of ‘uncompetitive activation’ by ascorbic acid: purification and kinetic properties of a myrosinase from Raphanus sativus seedlings

The role and effects of glucosinolates of Brassica species - a review

A Chromatographic Method for Separating and Identifying Intact 4-Methylthio-3-Butenyl Glucosinolate in Japanese Radish (Raphanus sativus L.)

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