glucobrassicin and sinigrin

Red cabbage (

Topics: Brassica; Chromatography, Liquid; Cooking; Glucose; Glucosinolates; Imidoesters; Indoles; Microwaves; Oximes; Sulfoxides; Tandem Mass Spectrometry

Evolution of important glucosinolates (GLSs), namely, sinigrin, glucoraphanin, glucoerucin and glucobrassicin, in three commonly consumed Brassica vegetables viz. white cabbage, Chinese cabbage and bok choy during their processing into vegetable powder was investigated. Drying was noted to be a major processing step causing significant losses of GLSs. Interestingly, different GLSs and even the same GLSs in different vegetables showed different thermal stabilities during drying. The stability of GLSs in vegetable powder during in vitro gastric digestion was also studied. Glucoraphanin exhibited the highest stability while glucobrassicin was the most vulnerable GLS under in vitro gastric conditions. White cabbage is found to be a promising material for the production of vegetable powder as it contains high contents of GLSs, especially glucoraphanin and glucoerucin, which are important precursors of anticarcinogenic compounds, namely sulforaphane and erucin. These two GLSs were also noted to be stable during in vitro gastric digestion.

Topics: Brassica; Dietary Fiber; Digestion; Food Handling; Glucose; Glucosinolates; Imidoesters; Indoles; Nutritive Value; Oximes; Powders; Sulfoxides; Vegetables

Plants must constantly adjust their growth and defense responses to deal with the wide variety of stresses they encounter in their environment. Among phytohormones, brassinosteroids (BRs) are an important group of plant steroid hormones involved in numerous aspects of the plant lifecycle including growth, development and responses to various stresses including insect attacks. Here, we show that BRs regulate glucosinolate (GS) biosynthesis and function in insect herbivory. Preference tests and larval feeding experiments using the generalist herbivore, diamondback moth (Plutella xylostella), revealed that the larvae prefer to feed on Arabidopsis thaliana brassinosteroid insensitive 1 (bri1-5) plants over wild-type Ws-2 or BRI1-Flag (bri1-5 background) transgenic plants, which results in an increase in larval weight. Analysis of GS contents showed that 3-(methylsulfinyl) propyl GS (C3) levels were higher in bri1-5 than in Ws2 and BRI1-Flag transgenic plants, whereas sinigrin (2-propenylglucosinolate), glucoerucin (4-methylthiobutylglucosinolate) and glucobrassicin (indol-3-ylmethylglucosinolate) levels were lower in this mutant. We investigated the effect of brassinolide (BL) on GS biosynthesis in Arabidopsis and radish (Raphanus sativus L.) by monitoring the expression levels of GS biosynthetic genes, including MAM1, MAM3, BCAT4 and AOP2, which increased in a BL-dependent manner. These results suggest that BRs regulate GS profiles in higher plants, which function in defense responses against insects.

Topics: Arabidopsis; Arabidopsis Proteins; Brassinosteroids; Cytochrome P-450 Enzyme System; Gene Expression Regulation, Plant; Glucosinolates; Indoles; Mutation; Plants, Genetically Modified; Protein Kinases; Raphanus; Transaminases

The aim of the study was to investigate the effect of storage on the contents of glucosinolates (GLS) and their degradation products in a boiled white cabbage. A 24h storage at 4 °C resulted in a decrease in GLS content (20-40%, depending on the cooking time applied) in the edible parts. The most significant losses were observed for sinigrin (20-45%), and the least for glucobrassicin (12-32%). Storage had a diversified effect on GLS breakdown products (indole-3-acetonitrile, indole-3-carbinol, ascorbigen and 3,3'-diindolylmethane released from glucobrassicin and 4-methylsulfinylbutanenitrile released from glucoiberin) in the boiled cabbage. The increase in the content of indole-3-acetonitrile, especially considerable within the first 24h of storage (and a simultaneous decrease in glucobrassicin) clearly indicates that degradation of GLS may occur during storage or cooling to 4 °C.

Topics: Ascorbic Acid; Brassica; Drug Stability; Fermentation; Food Handling; Food Preservation; Glucosinolates; Hot Temperature; Indoles

We profiled and quantified glucosinolates (GSLs), anthocyanins, free amino acids, and vitamin C metabolites in forty-five lines of green and red cabbages. Analysis of these distinct cabbages revealed the presence of 11 GSLs, 13 anthocyanins, 22 free amino acids, and vitamin C. GSL contents were varied amongst the different lines of cabbage. The total GSL content was mean 10.6 μmol/g DW, and sinigrin was the predominant GSL accounted mean 4.0 μmol/g DW (37.7% of the total) followed by glucoraphanin (1.9) and glucobrassicin (2.4). Amongst the 13 anthocyanins, cyanidin 3-(sinapoyl) diglucoside-5-glucoside levels were the highest. The amounts of total free amino acids in green cabbage lines ranged 365.9 mg/100g fresh weight (FW) to 1089.1mg/100g FW. Vitamin C levels were much higher in red cabbage line (129.9 mg/100g FW). Thus, the amounts of GSLs, anthocyanins, free amino acids, and vitamin C varied widely, and the variations in these compounds between the lines of cabbage were significant.

Topics: Amino Acids; Anthocyanins; Ascorbic Acid; Brassica; Food Analysis; GABA Agents; Glucosinolates; Imidoesters; Indoles; Oximes; Sulfoxides; Vitamins

Quantitative differences in plant defence metabolites, such as glucosinolates, may directly affect herbivore preference and performance, and indirectly affect natural enemy pressure. By assessing insect abundance and leaf damage rate, we studied the responses of insect herbivores to six genotypes of Brassica oleracea var. acephala, selected from the same cultivar for having high or low foliar content of sinigrin, glucoiberin and glucobrassicin. We also investigated whether the natural parasitism rate was affected by glucosinolates. Finally, we assessed the relative importance of plant chemistry (bottom-up control) and natural enemy performance (top-down control) in shaping insect abundance, the ratio of generalist/specialist herbivores and levels of leaf damage. We found that high sinigrin content decreased the abundance of the generalist Mamestra brassicae (Lepidoptera, Noctuidae) and the specialist Plutella xylostella (Lepidoptera, Yponomeutidae), but increased the load of the specialist Eurydema ornatum (Hemiptera, Pentatomidae). Plants with high sinigrin content suffered less leaf injury. The specialist Brevicoryne brassicae (Hemiptera, Aphididae) increased in plants with low glucobrassicin content, whereas the specialists Pieris rapae (Lepidoptera, Pieridae), Aleyrodes brassicae (Hemiptera, Aleyrodidae) and Phyllotreta cruciferae (Coleoptera, Chrysomelidae) were not affected by the plant genotype. Parasitism rates of M. brassicae larvae and E. ornatum eggs were affected by plant genotype. The ratio of generalist/specialist herbivores was positively correlated with parasitism rate. Although both top-down and bottom-up forces were seen to be contributing, the key factor in shaping both herbivore performance and parasitism rate was the glucosinolate concentration, which highlights the impact of bottom-up forces on the trophic cascades in crop habitats.

Topics: Animals; Aphids; Brassica; Genotype; Glucosinolates; Herbivory; Indoles; Insecta; Larva; Lepidoptera; Plant Leaves; Wasps

Within the family of Brassicaceae, an important source of glucosinolates (GLSs) is represented by horseradish ( Armoracia rusticana P. Gaertner, B. Meyer & Scherbius), cultivated for its roots, which are grated fresh or processed into a sauce and used as a condiment. The characteristic pungent flavor of the root depends on the abundance of the bioactive GLS molecules. In crude plant extracts (sprouts and roots) of an accession of horseradish largely diffused in the Basilicata region (southern Italy), which develops many sprouts and produces white, fiery, and sharp-flavored marketable roots, we characterized the GLS profile by LC-ESI-LTQ-FTICR-MS and IRMPD. In sprouts and roots we identified 16 and 11 GLSs, respectively. We confirmed the presence of sinigrin, 4-hydroxyglucobrassicin, glucobrassicin, gluconasturtin, and 4-methoxyglucobrassicin and identified glucoiberin, gluconapin, glucocochlearin, glucoconringianin, glucosativin, glucoibarin, 5-hydroxyglucobrassicin, glucocapparilinearisin or glucobrassicanapin, glucotropaeolin, and glucoarabishirsutain, not previously characterized in horseradish. Of particular note was the presence of the putative 2-methylsulfonyl-oxo-ethyl-GLS.

Topics: Armoracia; Chromatography, Liquid; Cyclotrons; Fourier Analysis; Glucosinolates; Indoles; Italy; Mass Spectrometry; Plant Roots; Sulfuric Acids

Black mustard, Brassica nigra, is highly variable in both constitutive resistance and induction response following damage by herbivores. A focal population from Ithaca, New York, was used to test the following two predictions of optimal defense theory: (1) that allocation to resistance will reduce plant performance in the absence of herbivores; and (2) that induction response will be negatively correlated with constitutive resistance. The experiment consisted of a half-sib mating design with 47 paternal families and four dams per sire, fully crossed with a damage treatment consisting of 25% leaf removal by the cabbage white butterfly, Pieris rapae, when plants had four leaves. Leaf trichome density, sinigrin concentration, and glucobrassicin concentration were 38%, 19%, and 16% higher, respectively, for the seventh leaf of damaged plants. Paternal families did not vary significantly in their induction response. Narrow-sense heritabilities were h(S)(2) = 0.51, 0.76, and 0.50 for constitutive leaf trichome density, sinigrin concentration, and glucobrassicin concentration, respectively. Positive genetic correlations were found between glucobrassicin concentration and days to first flower, suggesting a genetic cost of resistance. Induction responses were negatively correlated with constitutive allocation for leaf trichome density and sinigrin concentration. The results were therefore consistent with optimal defense theory, offering modest evidence for both predictions.

Topics: Animals; Butterflies; Glucosinolates; Indoles; Mustard Plant; New York; Phenotype; Plant Leaves; Random Allocation

The aim of this study was to optimize by micellar electrokinetic chromatography the separation of four glucosinolates, i.e. sinigrin, glucobrassicin and methoxyglucobrassicin involved in Cruciferae resistance mechanisms and glucotropaeolin used as an internal standard. The separation borate buffer which contained sodium dodecyl sulphate, tetramethylammonium hydroxide and methanol was firstly optimized by using a three variable Doehlert experimental design. The optimum concentrations found enabled, for the first time, to obtain an acceptable resolution between the two indole glucosinolates, glucobrassicin and methoxyglucobrassicin. Modifications of the method such as a capillary pre-rinse with pure borate buffer and a step change in voltage during experiment were performed to improve the resolutions between glucosinolates and to reduce the analysis time. This method was validated by a statistical analysis and showed good linearity, repeatability and reproducibility.

Topics: Buffers; Chromatography, Micellar Electrokinetic Capillary; Glucosinolates; Hydroxamic Acids; Indoles; Isothiocyanates; Reproducibility of Results; Sensitivity and Specificity; Thioglucosides; Vegetables

Significant induction of mixed-function-oxidase (MFO) activity was observed in the small intestines of rats within 4-6 hr of ingestion of a single meal containing a Brassica vegetable (cabbage). Intact Brussels sprouts and a fractionated methanol-water extract of Brussels sprouts induced similar degrees of MFO activity in the livers, and small and large intestines of rats. However, the residue left after extraction of the polar compounds did not induce MFO activity. Different amounts of the various naturally-occurring thioglycosides and glucosinolates were found in the intact Brussels sprouts and in the extract, but virtually none were found in the extracted residue. When glucusinolates that were found in Brussels sprouts (sinigrin, progoitrin, glucobrassicin and glucotropaeolin) were fed separately to rats, only the indole glucosinolate, glucobrassicin, induced MFO activity (causing induction in the small intestines of the rats). This is consistent with the inducing activity of the various hydrolysis products of this glucosinolate. This is the first study in which an attempt has been made to define the inducing compounds in Brassica vegetables by feeding the individual purified glucosinolates.

Topics: Animals; Antithyroid Agents; Brassica; Enzyme Induction; Food Analysis; Glucosinolates; Hydroxamic Acids; Indoles; Intestine, Large; Intestine, Small; Intestines; Isothiocyanates; Liver; Male; Mixed Function Oxygenases; Rats; Rats, Inbred Strains; Thioglucosides; Thioglycosides