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The oomycete plant pathogen Phytophthora cinnamomi causes a highly destructive root rot that affects numerous hosts. Integrated management strategies are needed to control P. cinnamomi in seminatural oak rangelands. We tested how biofumigation affects crucial stages of the pathogen's life cycle in vitro, in infested soils under laboratory conditions and in planta. Different genotypes of three potential biofumigant plant species ( Brassica carinata, Brassica juncea, Brassica napus) were collected at different phenological stages, analysed for their glucosinolate contents, and subsequently tested. The most effective genotypes against mycelial growth and sporangial production were further tested on the viability of chlamydospores in artificially infested natural soils and in planta on Lupinus luteus, a host highly susceptible to P.cinnamomi. Brassica carinata and B. juncea genotypes inhibited mycelial growth, decreased sporangial production, and effectively inhibited the viability of chlamydospores in soil, but only B. carinata decreased disease symptoms in plants. Effective genotypes of Brassica had high levels of the glucosinolate sinigrin. Biofumigation with Brassica plants rich in sinigrin has potential to be a suitable tool for control of oak root disease caused by P. cinnamomi in Spanish oak rangeland ecosystems. [ABSTRACT FROM AUTHOR]

Plutella xylostella L. is a notorious pest of cruciferous crops causing worldwide losses of $4–5 billion per year. Developing classical biological control to this pest include an introduction of host plants that act as natural enemies showing deviation from the preference-performance regimen in the evolutionary ecology of plant-insect interactions. The present study was designed to understand the role of glucosinolate-myrosinase system during P. xylostella interactions with a novel host. Adult moth preference and larval performance study were conducted on a novel host Lepidium latifolium L. (LL) that has high sinigrin content and was compared with its laboratory host Arabidopsis thaliana (AT). The glucosinolate-myrosinase system was studied in a time course experiment during larval feeding in choice and no-choice experiments. Adult moths visit and prefers LL over AT for oviposition. Conversely, LL leaves were not preferred and proved detrimental for P. xylostella larvae. Aliphatic and indolic glucosinolates were found to decrease significantly ( p ≤ 0.05) in AT during initial 12 h of P. xylostella challenge, whereas, they were not affected in LL. Also, MYB transcription factor expression and myrosinase activity in LL do not suggest a typical host response to a specialist insect. This preference-performance mismatch of P. xylostella on LL mediated by glucosinolate pattern suggests that this novel plant could be utilized in P. xylostella management. [ABSTRACT FROM AUTHOR]

Glucosinolate (GSL) hydrolysis is mediated by the enzyme myrosinase which together with specifier proteins can give rise to isothiocyanates (ITCs), thiocyanates, and nitriles (NITs) in cruciferous plants. However, little is known about the metabolism of GSLs by the human gut flora. The aim of the work was to investigate the metabolic fates of sinigrin (SNG), glucotropaeolin (GTP), gluconasturtiin (GNT), and their corresponding desulfo-GSLs (DS-GSLs). Three human gut bacterial strains, Enterococcus casseliflavus CP1, Lactobacillus agilis R16, and Escherichia coli VL8, were chosen for this study. GNT was metabolized to completion within 24 h to phenethyl ITC and phenethyl NIT (PNIT) by all bacteria, except for L. agilis R16 which produced only PNIT. At least 80 % of GTP and SNG were metabolized by all bacteria within 24 h to the corresponding ITCs and NITs. The pH of media over time gradually became acidic for both L. agilis R16 and E. coli VL8, while for E. casseliflavus CP1 the media became slightly alkaline with NIT and ITC production occurring between pH 3.0 and 7.5. ITC production peaked between 4 and 10 h in most cases and gradually declined while NIT production increased and remained relatively constant over time. The total percentage products accounted for 3-53 % of the initial GSL. NITs were produced from DS-GSLs suggesting an alternative metabolism via desulfation for the food based GSLs. The metal ion dependency for NIT production for GNT and its DS form was investigated where it was shown that Fe increased NIT production, while Mg stimulated the formation of ITC. [ABSTRACT FROM AUTHOR]

Ecological and evolutionary processes historically have been assumed to operate on significantly different time-scales. We know now from theory and work in experimental and model systems that these processes can feed back on each other on mutually relevant time-scales., Here, we present evidence of a soil-mediated eco-evolutionary feedback on the population dynamics of an invasive biennial plant, Alliaria petiolata., As populations age, natural selection drives down production of A. petiolata's important antimycorrhizal allelochemical, sinigrin. This occurs due to density-dependent selection on sinigrin, which is favoured under interspecific, but disfavoured under intraspecific, competition., We show that population stochastic growth rates (λS) and plant densities are positively related to sinigrin concentration measured in seedling roots. This interaction is mediated by sinigrin's positive effect on seedling and summer survival, which are important drivers of λS., Together, these illustrate how the evolution of a trait shaped by natural selection can influence the ecology of a species over a period of just years to decades, altering its trajectory of population growth and interactions with the species in the soil and plant communities it invades., Our findings confirm the predictions that eco-evolutionary feedbacks occur in natural populations. Furthermore, they improve our conceptual framework for projecting future population growth by linking the variation in plant demography to a critical competitive trait (sinigrin) whose selective advantages decrease as populations age. [ABSTRACT FROM AUTHOR]

The selection of oviposition sites by aphidophagous insects is complex because of tritrophic interactions among host plant, aphid, and natural enemies. Several factors are known to affect the choice of oviposition site by aphidophagous hoverflies. The decisions of ovipositing females about where to lay their eggs are even more important in insects whose newly hatched offspring have limited dispersal ability, such as most aphidophages. In this study, we focused on the oviposition responses of two generalist aphidophagous syrphids ( Eupeodes luniger and Episyrphus balteatus ) toward host plant–aphid combinations differing in sinigrin content and the presence of intra- and interspecific competitors. The oviposition preference of Eupeodes luniger was significantly influenced in a reverse manner by the presence of intraguild competitors and also by the sinigrin content of host plants (P < 0.0001 for both factors). Likewise, the overall proportion of eggs laid by female Episyrphus balteatus was greater on aphids with relatively low levels of sinigrin. Our findings help in understanding the factors governing the oviposition responses of aphidophagous predators. [ABSTRACT FROM AUTHOR]

Sinigrin (allyl-glucosinolate or 2-propenyl-glucosinolate) is a natural aliphatic glucosinolate present in plants of the Brassicaceae family, such as broccoli and brussels sprouts, and the seeds of Brassica nigra (mustard seeds) which contain high amounts of sinigrin. Since ancient times, mustard has been used by mankind for its culinary, as well as medicinal, properties. It has been systematically described and evaluated in the classical Ayurvedic texts. Studies conducted on the pharmacological activities of sinigrin have revealed anti-cancer, antibacterial, antifungal, antioxidant, anti-inflammatory, wound healing properties and biofumigation. This current review will bring concise information about the known therapeutic activities of sinigrin. However, the information on known biological activities is very limited and, hence, further studies still need to be conducted and its molecular mechanisms also need to be explored. This review on the therapeutic benefits of sinigrin can summarize current knowledge about this unique phytocompounds. [ABSTRACT FROM AUTHOR]

1. Plant secondary metabolites can govern prey-predator interactions by altering the diet breadth of predators and sometimes provide an ecological refuge to prey. Brassicaceae plants and their specialist pests can be used as a model system for understanding the role of chemically mediated effects restricting the diet breadth of natural enemies, and consequently the occurrence of enemy-free space for the specialist pest. 2. The objective of the present study was to test the performance of the generalist predator Episyrphus balteatus De Geer ( Diptera: Syrphidae) fed on the specialist herbivore Brevicoryne brassicae L.( Homoptera: Aphididae), reared on two different brassica species: black mustard ( Brassica nigra), a wild species with high levels of sinigrin; and canola ( Brassica napus), a cultivated species without sinigrin. 3. The preference and performance of the predator and the performance of the prey were measured. Sinigrin was quantified by high-performance liquid chromatography in both leaf samples and aphids reared on the two host plants. 4. The cabbage aphid performed better on canola than on black mustard. The performance of the predator on this aphid when reared on canola was clearly better than when reared on black mustard. Females had a higher overall preference for cabbage aphids reared on canola than on black mustard. 5. The ability of aphids reared on plants with high glucosinolate content to reduce the performance of their generalist predators indicates that the presence of B. nigra may provide enemy-free space for the cabbage aphid from its predator, a concept that has useful application in the context of biological control for agricultural systems. [ABSTRACT FROM AUTHOR]

The joint toxicity of chlorantraniliprole, a novel insecticide that acts on ryanodine receptors, and sinigrin, a natural plant defense compound from brassicaceous vegetables, to the larvae of Spodoptera exigua (Hübner) was determined in this paper. Additionally, the joint effects of the two compounds on cytochrome P450 enzyme activity and on the expression levels of mRNA of three P450 genes (including CYP9A9, CYP6B, and CYP4G37) and an NADPH cytochrome P450 reductase gene (HQ852049) were investigated. The toxicity of the mixture of chlorantraniliprole and sinigrin to fourth-instar S. exigua larvae was 1.60-fold higher than the toxicity of the chlorantraniliprole-only treatment after 24 h. Induced by chlorantraniliprole and sinigrin, the specific activity of the P450 O-deethylase was affected in a time-, dose-, and organ-specific manner in fifth-instar S. exigua larvae. The effects were more pronounced in the midgut than in the fat body. The specific activity of the P450 O-deethylase in almost all treatments increased at 12, 24, and 36 h posttreatment compared with that in the control. Based on real-time PCR analyses, the expression levels of the P450 genes CYP9A9, CYP6B, and CYP4G37 and the NADPH cytochrome P450 reductase gene HQ852049 in fifth-instar S. exigua larvae were induced by chlorantraniliprole and sinigrin, and the trends were similar to the specific activity of the P450 O-deethylase. Therefore, the CYP9A9, CYP6B, and HQ852049 in the tested genes were the most inducible genes that were expressed when the S. exigua larvae were exposed to chlorantraniliprole and sinigrin. [ABSTRACT FROM AUTHOR]

An ion-pair reversed-phase high-performance liquid chromatography ( HPLC) method was developed for the analysis of sinigrin in Ethiopian mustard ( Brassica carinata A. Braun) seed and seed fractions. Separation was compared on several RP- HPLC columns (Inertsil® ODS-4 C18 and ZORBAX® Eclipse XDB-C18) with an isocratic eluent containing 100% aqueous (aq.) tetramethylammonium bromide (10 m m, pH 5.0). Sinigrin retention was affected by HPLC variables including the type of ion-pair reagent, buffer strength and pH, acetonitrile concentration, column temperature and eluent flow rate. Partial validation demonstrated this optimised chromatographic condition to be linear, accurate and precise. Multistage extraction using 70% (v/v) aq. methanol was more efficient than 50% (v/v) aq. acetonitrile. In addition, the matrix effect and recovery rate as well as processing efficiency of the analytical protocol were determined. This method is suitable for high throughput analysis of sinigrin in Ethiopian mustard seed and seed fractions. [ABSTRACT FROM AUTHOR]

Sinigrin is a class of glucosinolates found naturally in plants of the Brassicaceae family. Lately, studies have shown that sinigrin possesses anticancer, antibacterial and anti-inflammatory activities. Since its efficacy has not been explored on wound healing, we examined the effect of sinigrin on HaCaT cells. We also aimed at formulating sinigrin into phytosome to form a sinigrin–phytosome complex and study the wound healing and cytotoxic activities on A-375 and HaCaT cells. Sinigrin was efficiently formulated into the phytosome with an average particle size of 153 ± 39 nm, zeta potential of 10.09 ± 0.98 mV and complex efficiency of 69.5 ± 5%. The formation of the sinigrin–phytosome complex was confirmed by DSC and FTIR analysis. The sinigrin–phytosome complex significantly exhibited wound healing effects when compared to sinigrin alone. After 42 h, the phytosome complex completely healed the wound, whereas sinigrin alone showed only 71% wound closure. The sinigrin–phytosome complex displayed minimal toxicity towards HaCaT cells and at higher concentrations, it showed potent activity towards A-375. The results indicated that sinigrin–phytosome complex augmented the therapeutic potential of sinigrin towards the wound healing activity and this approach should be explored further for cancerous wound treatment. [ABSTRACT FROM AUTHOR]

Sinigrin is a major component of cruciferous vegetables such as cabbage, Brussels sprout, mustard greens and broccoli. The present study demonstrates the protective effects of sinigrin against the non-enzymatic glycation of albumin and lens crystallin based on fluorescence spectroscopy, circular dichroism and molecular interaction studies. Sinigrin was found to be a potent inhibitor for both the early (Amadori product) and advanced glycation end products (AGEs). In addition, the in vitro glycation studies of lens crystallin demonstrated the strong antiglycation activity of sinigrin. Computational studies using molecular docking approach revealed the interaction pattern of sinigrin with BSA and the binding affinity of sinigrin was found to be greater than the other potent natural inhibitors of glycation such as quercetin, apigenin, and curcumin. [ABSTRACT FROM AUTHOR]

Horseradish is grown for its enlarged taproot that is widely used as a dish condiment and as a source of horseradish peroxidase. Nowadays, the species is gaining great interest due to the richness in bioactive compounds that besides providing a high nutritional value are tested for innovative applications in different fields. Nevertheless, the effect of crop management on root yield and glucosinolates (GLS) biosynthesis is poorly documented. Aim of this study was to evaluate the root yield and GLS concentration of two field-grown horseradish accessions (Cor and Mon) grown with nitrogen (N) alone and both N and sulphur (S) (-N-S, +N-S and +N+S treatments) and harvested at different times [late autumn (LA), 2011 and 2012, early spring (ES), 2012]. Yield increased throughout the harvests up to 48% on average of the fertilised treatments and 25% in the unfertilised control. Conversely, root GLS concentration significantly declined in the unfertilised control throughout the harvests [from 7.6 in LA_2011 to 1.43 mmol/g dry matter (DM) in LA_2012] while it highly increased in plants grown with N alone and with both N and S by 46 and 98%, respectively, from LA_2011 to ES_2012 (up to 11.9 and 21.1 mmol/g DM, respectively); then it drastically decreased by 80% on average, in the next harvest. Among individual GLS, the concentration of sinigrin and nasturtin similarly varied as effect of the analysed factors, showing the highest values in Cor accession. The data show that although the level of GLS is highly dependent on genotype, fertilisation and harvesting date may play a primary role in determining the yield and GLS concentration in horseradish root. [ABSTRACT FROM AUTHOR]

Volatile allyl isothiocyanate (AITC) derives from the biodegradation of the glucosinolate sinigrin and has been associated with growth inhibition in several plants, including the model plant Arabidopsis thaliana. However, the underlying cellular mechanisms of this feature remain scarcely investigated in plants. In this study, we present evidence of an AITC-induced inhibition of actin-dependent intracellular transport in A. thaliana. A transgenic line of A. thaliana expressing yellow fluorescent protein (YFP)-tagged actin filaments was used to show attenuation of actin filament movement by AITC. This appeared gradually in a time- and dose-dependent manner and resulted in actin filaments appearing close to static. Further, we employed four transgenic lines with YFP-fusion proteins labeling the Golgi apparatus, endoplasmic reticulum (ER), vacuoles and peroxisomes to demonstrate an AITC-induced inhibition of actin-dependent intracellular transport of or, in these structures, consistent with the decline in actin filament movement. Furthermore, the morphologies of actin filaments, ER and vacuoles appeared aberrant following AITC-exposure. However, AITC-treated seedlings of all transgenic lines tested displayed morphologies and intracellular movements similar to that of the corresponding untreated and control-treated plants, following overnight incubation in an AITC-absent environment, indicating that AITC-induced decline in actin-related movements is a reversible process. These findings provide novel insights into the cellular events in plant cells following exposure to AITC, which may further expose clues to the physiological significance of the glucosinolate-myrosinase system. [ABSTRACT FROM AUTHOR]

Myrosinase, which is present in cruciferous plant species, plays an important role in the hydrolysis of glycosides such as glucosinolates and is involved in plant defense. Brassicaceae myrosinases are diverse although they share common ancestry, and structural knowledge about myrosinases from cabbage (Brassica oleracea) was needed. To address this, we constructed a three-dimensional model structure of myrosinase based on Sinapis alba structures using Iterative Threading ASSEmbly Refinement server (I-TASSER) webserver, and refined model coordinates were evaluated with ProQ and Verify3D. The resulting model was predicted with β/α fold, ten conserved N-glycosylation sites, and three disulfide bridges. In addition, this model shared features with the known Sinapis alba myrosinase structure. To obtain a better understanding of myrosinase--sinigrin interaction, the refined model was docked using Autodock Vina with crucial key amino acids. The key nucleophile residues GLN207 and GLU427 were found to interact with sinigrin to form a hydrogen bond. Further, 20-ns molecular dynamics simulation was performed to examine myrosinase--sinigrin complex stability, revealing that residue GLU207 maintained its hydrogen bond stability throughout the entire simulation and structural orientation was similar to that of the docked state. This conceptual model should be useful for understanding the structural features of myrosinase and their binding orientation with sinigrin. [ABSTRACT FROM AUTHOR]

This study identified glucosinolate (GLS) breakdown products and determined the relationships between such products and parent GLS in boiled Brussels sprouts. This is the first ever study to analyse all groups of GLS breakdown products (aliphatic, aralkyl and indole) in boiled vegetables. In the examined boiled Brussels sprouts, isothiocyanates were not determined in the edible parts or cooking water. The presence of seven breakdown products was determined as indole-3-acetonitrile, indole-3-carbinol, ascorbigen and 3,3'-diindolylmethane released form glucobrassicin, 3-butenylnitrile released from sinigrin, 4-methylsulfinylbutanenitrile released from glucoiberin, and 2-phenylacetonitrile released from gluconasturtiin. In the edible parts, the content of indole-3-acetonitrile and 3-butenylnitrile was particularly high at approximately 30 and 16 µmol/100 g FW, which was equivalent to 54 and 9% of the initial value of the parent GLS, respectively. [ABSTRACT FROM AUTHOR]

Inter-cropping mustard and oilseed radish in potato production has been shown to suppress potato cyst nematode (PCN) reproduction in field plots. This suppressive effect is mostly attributed to the release of glucosinolate (GSL) hydrolysis products such as isothiocyanates, following chopping and incorporation of the crop biomass. This study examined the degradation of sinigrin introduced into soil where Indian mustard and oilseed radish were cultivated and the effect on PCN suppression. Glucosinolate degradation was measured by introducing sinigrin into the soil samples pre-planting, pre- and post-incorporation of the brassicas, while the soil microbial activity was quantified as the concentration of fluorescein di-acetate (FDA) g −1 oven dry soil. Sinigrin was significantly ( P < 0.001) degraded pre- and post-incorporation of the brassicas cultivated in unsterilized soil. The total microbial activity increased significantly ( P < 0.001) pre- and post-incorporation of brassicas when compared with fallow controls. Unsterilized soils planted with oilseed radish resulted in a significant ( P < 0.027) suppression of G. pallida encysted eggs (30–35% mortality). Microbial activity correlated positively with G. pallida mortality ( R 2 = 0.94, P < 0.001), but inversely with sinigrin degradation. This study has revealed that brassicas used for biofumigation may affect soil borne pests and pathogens not just after incorporation of the crop residues, but also during active growth of these plants. [ABSTRACT FROM AUTHOR]

The antifungal properties of isothiocyanates released from the hydrolysis of the glucosinolate sinigrin were assessed on an Armillaria mellea strain in Petri dishes. The fumigation with sinigrin at 100 µM showed a fungicidal effect, while lower rates determined a temporary fungistatic effect. The application of increasing rates of solid and liquid biofumigant formulations on A. mellea inoculated potted peach plants showed an increase of soil nitrate concentration, basal respiration, microbial biomass, leaf nitrogen and chlorophyll concentration. These effects indicated a stimulating effect of Brassicaceae derivatives on soil biological activity and plant growth. The application of a rate of meal higher than 6.42 g kg−1 soil caused a stunted growth and the death of some plants showing a clear phytotoxic effect of the treatments. The inhibition of A. mellea growth observed in in vitro trials was not evidenced in in vivo experiments due to the lack of infection symptoms in experimentally inoculated potted trees. [ABSTRACT FROM AUTHOR]

Alliaria petiolata (garlic mustard, Brassicaceae) contains the glucosinolate sinigrin as well as alliarinoside, a γ-hydroxynitrile glucoside structurally related to cyanogenic glucosides. Sinigrin may defend this plant against a broad range of enemies, while alliarinoside confers resistance to specialized (glucosinolate-adapted) herbivores. Hydroxynitrile glucosides and glucosinolates are two classes of specialized metabolites, which generally do not occur in the same plant species. Administration of [UL-14C]-methionine to excised leaves of A. petiolata showed that both alliarinoside and sinigrin were biosynthesized from methionine. The biosynthesis of alliarinoside was shown not to bifurcate from sinigrin biosynthesis at the oxime level in contrast to the general scheme for hydroxynitrile glucoside biosynthesis. Instead, the aglucon of alliarinoside was formed from metabolism of sinigrin in experiments with crude extracts, suggesting a possible biosynthetic pathway in intact cells. Hence, the alliarinoside pathway may represent a route to hydroxynitrile glucoside biosynthesis resulting from convergent evolution. Metabolite profiling by LC-MS showed no evidence of the presence of cyanogenic glucosides in A. petiolata. However, we detected hydrogen cyanide (HCN) release from sinigrin and added thiocyanate ion and benzyl thiocyanate in A. petiolata indicating an enzymatic pathway from glucosinolates via allyl thiocyanate and indole glucosinolate derived thiocyanate ion to HCN. Alliarinoside biosynthesis and HCN release from glucosinolate-derived metabolites expand the range of glucosinolate-related defenses and can be viewed as a third line of defense, with glucosinolates and thiocyanate forming protein being the first and second lines, respectively. [ABSTRACT FROM AUTHOR]

The impact of sulfate deprivation and atmospheric H2S and SO2 nutrition on the content and composition of glucosinolates was studied in Brassica juncea and B. rapa. Both species contained a number of aliphatic, aromatic and indolic glucosinolates. The total glucosinolate content was more than 5.5-fold higher in B. juncea than in B. rapa, which could solely be attributed to the presence of high levels of sinigrin, which was absent in the latter species. Sulfate deprivation resulted in a strong decrease in the content and an altered composition of the glucosinolates of both species. Despite the differences in patterns in foliarly uptake and metabolism, their exposure hardly affected the glucosinolate composition of the shoot, both at sulfate-sufficient and sulfate-deprived conditions. This indicated that the glucosinolate composition in the shoot was hardly affected by differences in sulfur source (viz., sulfate, sulfite and sulfide). Upon sulfate deprivation, where foliarly absorbed H2S and SO2 were the sole sulfur source for growth, the glucosinolate composition of roots differed from sulfate-sufficient B. juncea and B. rapa, notably the fraction of the indolic glucosinolates was lower than that observed in sulfur-sufficient roots. [ABSTRACT FROM AUTHOR]

Cruciferous vegetables are well known and worldwide consumed due to their health benefits and cancer prevention properties. As a desirable cruciferous plant, Ethiopian mustard (Brassica carinata A. Braun) and its glucosinolate sinigrin were tested in the in vivo Drosophila melanogaster (SMART) and the in vitro HL60 (human promyelocytic leukaemia cell line) systems. High performance liquid chromatography (HPLC) analysis of plant samples confirmed the presence of sinigrin as principal B. carinata glucosinolate. SMART was performed by feeding D. melanogaster larvae either with different concentrations of plant/compound samples or combining them with hydrogen peroxide (a potent oxidative mutagen) being both antimutagenics. HL60 assays showed the tumoricidal activity of plant samples (IC50 = 0.28 mg·mL-1) and the breakdown products of sinigrin hydrolysis (IC50 = 2.71 μM). Our results enhance the potential of B. carinata as health promoter and chemopreventive in both systems and the leading role of sinigrin in these effects. [ABSTRACT FROM AUTHOR]

Aims: This study explores the biofumigation effects of glucosinolate (GSL) containing Brassica oleracea plant material on beneficial, non-target soil organisms, and aims to relate those effects to differences in GSL profiles. Methods: Leaf material of purple sprouting broccoli 'Santee', Savoy cabbage 'Wintessa', and the wild B. oleracea accession Winspit was analysed for GSL production and used for biofumigation experiments on the beneficial soil invertebrates, Folsomia candida (springtail) and Eisenia andrei (earthworm) and the soil bacterial community. Results: When mixed into soil, the Winspit plant material exerted the highest toxic effects on beneficial soil invertebrates by reducing survival and reproduction. Total GSL levels varied substantially between genotypes, in particular the aliphatic GSL (AGSL) sinigrin and gluconapin being highly abundant or exclusively present in Winspit. Differences between the genotypes regarding biofumigation effects on the soil microbial community were only observed on a temporal basis with the largest difference in bacterial community structure after 1 week. Conclusions: The high total GSL content in biofumigated soil could explain the toxicity of Winspit for soil invertebrates. These effects are likely to be the results of high AGSL levels in Winspit. The use of wild B. oleracea crops, such as Winspit, for biofumigation practices would need a proper assessment of the overall impact on soil biota before being applied on a wide scale. [ABSTRACT FROM AUTHOR]

Aflatoxins (AFs) are secondary metabolites produced by different species of Aspergillus , such as Aspergillus flavus and Aspergillus parasiticus , which possess mutagenic, teratogenic and carcinogenic activities in humans. In this study, active packaging devices containing allyl isothiocyanate (AITC) or oriental mustard flour (OMF) + water were tested to inhibit the growth of A . parasiticus and AFs production in fresh pizza crust after 30 d. The antimicrobial and anti-aflatoxin activities were compared to a control group (no antimicrobial treatment) and to a group added with commercial preservatives (sorbic acid + sodium propionate). A . parasiticus growth was only inhibited after 30 d by AITC in filter paper at 5 μL/L and 10 μL/L, AITC sachet at 5 μL/L and 10 μL/L and OMF sachet at 850 mg + 850 μL of water. However, AFs production was inhibited by all antimicrobial treatments in a dose-dependent manner. More importantly, AITC in a filter paper at 10 μL/L, AITC sachet at 10 μL/L, OMF sachet at 850 mg + 850 μL of water and sorbic acid + sodium propionate at 0.5–2.0 g/Kg completely inhibited AFs formation. The use of AITC in active packaging devices could be a natural alternative to avoid the growth of mycotoxinogenic fungi in refrigerated bakery products in substitution of common commercial preservatives. [ABSTRACT FROM AUTHOR]

Nanocomposite carboxymethyl cellulose films containing sinigrin ( SNG) were prepared by stirring 2% (w/v) carboxymethyl cellulose ( CMC) and 2% (w/v) glycerol (as a plasticizer) in distilled water with or without SNG (an antimicrobial precursor) as a 99% pure reagent ( pSNG) or as a crude extract ( cSNG). These films plus normal CMC film with or without SNG were tested on Escherichia coli O157:H7- inoculated beef for antimicrobial activity. Beef pieces measuring 6 × 5 × 2 cm3 (L × W × H) were dipped in an E. coli O157:H7 broth suspension containing >8 log10 CFU ml−1 and were drained for 3 min over a sterile cloth. They were wrapped in CMC or NCMC films, placed in a high oxygen barrier film (Deli *1), vacuum-packaged and stored at 8°C for 5, 8, 12 and 18 days. The CMC and NCMC films without SNG were not antimicrobial against E. coli O157:H7; however, NCMC and CMC films with SNG were highly antimicrobial. After 5 days at 8°C, E. coli O157:H7 was reduced more than 4 log10 by the NCMC• pSNG film and this reduction remained almost the same until 18 days at 8°C when E. coli O157:H7 was reduced >5 log10 CFU g−1 meat. Significance and Impact of the Study Transparent nanoparticulate carboxymethyl cellulose (CMC) films containing sinigrin (SNG), an antimicrobial precursor, controlled surface contamination of packaged fresh beef by the pathogen Escherichia coli O157:H7 when stored at 8°C. Films with nanoparticulation that carried pure SNG or the naturally occurring SNG in Oriental mustard were significantly more antimicrobial than similar films without nanoparticulation. As films without sinigrin were not antimicrobial, the combinations studied showed that nanoparticulation of the packaging film enhanced delivery of the antimicrobial incorporated within the film. [ABSTRACT FROM AUTHOR]

This work examined Escherichia coli O157:H7 strain 02-0304 for putative genes responsible for sinigrin hydrolysis. Sinigrin is a glucosinolate present in Oriental mustard ( Brassica juncea ), and its hydrolysis is mediated in plants by the enzyme myrosinase. Sinigrin hydrolysis by plant or bacterial myrosinase yields allyl isothiocyanate (AITC) which is bactericidal. In silico analysis using public databases found sequence similarity between plant myrosinase and enzymes encoded by genes from β -glucosidase families in E. coli O157:H7. Specifically, 6-phospho- β -glucosidase encoded by the genes bglA and ascB (family 1), and chbF (family 4) present in E. coli O157:H7 showed the highest similarity. Polymerase chain reaction (PCR) confirmed the presence of bglA , ascB , and chbF in the clinical E. coli strain tested. Disruption of these genes in wild-type E. coli O157:H7 strain 02-0304 using lambda-red replacement created single and double mutants. The relative importance of each gene in the hydrolysis of sinigrin by E. coli O157:H7 was also assessed by comparing gene expression and sinigrin degradation rates among the E. coli O157:H7 wild-type strain and its mutants. The results suggested that the genes bglA and ascB play a substantial role in the degradation of sinigrin by E. coli O157:H7 strain 02-0304. [ABSTRACT FROM AUTHOR]

Control of Salmonella in poultry is a public health concern as salmonellosis is one of the most common foodborne diseases worldwide. This study aimed to screen the ability of 5 Salmonella serovars to degrade the mustard glucosinolate, sinigrin (by bacterial myrosinase) in Mueller-Hinton broth at 25 °C for 21 d and to reduce Salmonella on fresh chicken breasts by developing an edible 0.2% (w/v) κ-carrageenan/2% (w/v) chitosan-based coating containing Oriental mustard extract, allyl isothiocyanate (AITC), EDTA or their combinations. Individual Salmonella serovars degraded 50.2%–55.9% of the sinigrin present in 21 d. κ-Carrageenan/chitosan-based coatings containing 250 mg Oriental mustard extract/g or 50 μl AITC/g reduced the numbers of Salmonella on chicken breasts 2.3 log 10 CFU/g at 21 d at 4 °C. However, when either mustard extract or AITC was combined with 15 mg/g EDTA in κ-carrageenan/chitosan-based coatings, Salmonella numbers were reduced 2.3 log 10 CFU/g at 5 d and 3.0 log 10 CFU/g at 21 d. Moreover, these treatments reduced numbers of lactic acid bacteria and aerobic bacteria by 2.5–3.3 log 10 CFU/g at 21 d. κ-Carrageenan/chitosan coatings containing either 50 μl AITC/g or 250 mg Oriental mustard extract/g plus 15 mg EDTA/g have the potential to reduce Salmonella on raw chicken. [ABSTRACT FROM AUTHOR]

Cauliflower ( Brassica oleraceae L. var. Botrytis ) is a good source of bioactive compounds, such as glucosinolates, phenolic compounds and vitamins. In this study, the effects of some processes ( i.e. boiling, steaming) on the sinigrin bioaccessibility as a major glucosinolate found in cruciferous vegetables after in vitro digestion, also in vitro antimutagenic activities, total phenols and total antioxidant capacities of cauliflower were determined. The sinigrin content was reduced by approximately 9.6% and 29.1% in steamed and boiled cauliflower ( p > 0.05), respectively. After in vitro simulated digestion, sinigrin content was decreased by 26.4% in raw samples, increased by 29.5% and 114.7% in steamed and boiled samples, respectively. In all samples, mutagenic effect to Salmonella typhimurium TA 100 was not seen. When samples were steamed, phenol content was increased by 14.83%. After boiling total phenol content of cauliflower was decreased by 1.8%. Total antioxidant capacities (TAC) measured by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3 ethylbenzothiazoline-6-sulfonic acid) (ABTS) methods were increased by 47% and 39%, respectively ( p < 0.05) in steamed samples and decreased by 8% and 7% with boiling, respectively ( p > 0.05). TAC in raw sample of cauliflower, which was investigated in phosphomolybdenum assays, was determined as 18.7 mg ascorbic acid equivalents (AAE)/100 g. In all cases, the highest antioxidant activity was determined in the steamed samples, while the lowest antioxidant activity was in boiled samples. [ABSTRACT FROM AUTHOR]

Factors, including pH, temperature, glucose concentration, and iron compounds, affect the activity of plant myrosinase and, consequently, endogenous glucosinolate degradation. These factors also may affect glucosinolate degradation by bacterial myrosinase. Therefore, this study examined the effect of temperature (4 to 21°C), glucose (0.05 to 1.0%), and iron (10 mM ferrous or ferric) on sinigrin degradation by Salmonella or Listeria monocytogenes cocktails in Mueller-Hinton broth and the effect of sinigrin degradation on bacterial viability. The degradation of sinigrin by both pathogens increased with higher temperatures (21 > 10 > 4°C). Salmonella and L. monocytogenes cocktails hydrolyzed 59.1 and 53.2% of sinigrin, respectively, at 21°C up to 21 days. Both iron compounds significantly enhanced sinigrin degradation by the pathogens. On day 7, sinigrin was not detected when the Salmonella cocktail was cultured with ferrous iron or when the L. monocytogenes cocktail was cultured in Mueller-Hinton broth containing ferric iron. In contrast, ferric and ferrous iron inhibited the activity of 0.002 U/ml myrosinase from white mustard by 63 and 35%, respectively, on day 1. Salmonella and L. monocytogenes cocktails were able to degrade >80% of sinigrin at 0.05 and 0.1% glucose; however, 0.25 to 1.0% glucose significantly reduced sinigrin degradation. Although both pathogens significantly degraded sinigrin, the allyl isothiocyanate (AITC) recoverable was ≤6.2 ppm, which is not inhibitory to Salmonella or L. monocytogenes. It is probable that the gradual hydrolysis of sinigrin to form AITC either did not produce an inhibitory level of AITC or the AITC formed was unstable in the aqueous medium and rapidly decomposed to new compounds that were less bactericidal against the pathogens. [ABSTRACT FROM AUTHOR]

Recently, controlled production of plants to enhance specific ingredients, such as sinigrin in Wasabi effective for antibacterial and anticancer, in the plants has become more important in order to use the ingredients efficiently. It is, however, difficult to develop a plant production method for controlling the sinigrin amount, because the sinigrin production mechanism is not clear. Therefore, it is crucial to evaluate distribution and metabolic pathways of sinigrin and related molecules in the wasabi tissue. Because time-of-flight (ToF)-SIMS provides molecular distributions of insulation samples including plant tissues on a submicron scale, it is useful for such a purpose. On the other hand, interpretation of intricate ToF-SIMS spectra of complex samples is often difficult. Recently, multivariate analysis techniques, such as principal component analysis and multivariate curve resolution, successfully applied into a variety of scientific fields have been also introduced into ToF-SIMS data. Moreover, gentle secondary ion mass spectrometry (G-SIMS), developed for analyzing static-SIMS spectra in terms of the degree of fragmentation, has recently been applied to various samples. In this study, sections of Wasabi petioles were evaluated with ToF-SIMS and the data analysis techniques to clarify the distribution of sinigrin molecule in the wasabi tissue. A combination of multivariate analysis and G-SIMS worked effectively to interpret the complex ToF-SIMS data of the plant tissue. As a result, the detailed distribution of sinigrin in the plant tissue was indicated by ToF-SIMS and the data analysis techniques. Copyright © 2014 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]