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Glucosinolates (GLs) are important precursors of anticancer isothiocyanates in cruciferous plants. However, GLs in aqueous solution have been found to decompose under certain conditions, and the effect of metal ions remains unclear. In this study, high-purity glucoraphanin and glucoraphenin were used to explore the effects of metal ions with thermal treatment. The degree of GLs decomposition was affected by the type and concentration of metal ions, temperature, and duration of heating. Fe 3+ (1 mM) was found to cause the decomposition of 78.1 % of glucoraphanin and 94.7 % of glucoraphenin in 12 h at 100 °C, while Cu 2+ completely decomposed both GLs. The decomposition products were all the corresponding nitriles, and decomposition dynamic curves were first-order. In addition to accelerating hydrolysis, metal ions may promote the generation of nitriles as catalysts. The exploration of GLs decomposition could help to adopt more effective methods to avoid the formation of toxic compounds., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier Ltd.)

Vegetables are frequently processed before consumption. However, vegetable functionalization continues beyond ingestion as the human digestive tract exposes vegetable products to various conditions (e.g. elevated temperature, pH alterations, enzymes, electrolytes, mechanical disintegration) which can affect the stability of micronutrients and phytochemicals. Besides the extent to which these compounds withstand the challenges posed by digestive conditions, it is equally important to consider their accessibility for potential absorption by the body. Therefore, this study investigated the impact of static in vitro digestion on the stability (i.e. concentration) and bioaccessibility of vitamin C, vitamin K1, glucosinolates, S-alk(en)yl-l-cysteine sulfoxides (ACSOs) and carotenoids in Brussels sprouts (Brassica oleracea var. gemmifera) and leek (Allium ampeloprasum var. porrum). Water-soluble compounds, glucosinolates and ACSOs, remained stable during digestion while vitamin C decreased by >48%. However, all water-soluble compounds were completely bioaccessible. Lipid-soluble compounds were also stable during digestion but were only bioaccessible for 26-81%., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

The complete exploitation of Brassica napus plants is a study hotspot, since it is an essential oil crop that is widely cultivated across the world. Glucosinolate is a unique secondary metabolite in the Brassicaceae family, and its content has a substantial influence on rapeseed development and quality. Its degradation products have various physiological functions, among which Nitrile specific proteins (NSPs) can hydrolyze glucosinolate and hence influence the balance of plant immunity and growth. However, the related gene families in B. napus have not been investigated. Here, 72 NSP family members were discovered and described in B. napus based on their sequence structures, physiological correlations, phonological locations, and expression levels. According to collinearity studies, the NSP proteins in B. napus and A. thaliana are closely related. Analysis of BnNSP expression patterns in various tissues revealed that BnNSPs exhibit high tissue specificity, implying that BnNSPs may play distinguish functions in various developmental phases. We discovered that NSPs may be regulated by hormones such as abscisic acid (ABA), gibberellin (GA), and metallic jasmonate (MeJA) based on the expression of NSPs during hormone treatment. The results provide valuable information for the future functional characterization of BnNSP genes.

The cultivation of Camelina sativa (L.) Crantz is rapidly increasing due to oil production resulting in a substantial volume of by-products, which still have an interesting composition in secondary metabolites, especially glucosinolates. Therefore, a green extraction procedure of glucosinolates by Pressurised Liquid Extraction was developed and optimized using a chemometric approach. Furthermore, the glucosinolates were purified by solid phase extraction, and a preliminary study on bioaccessibility and bioavailability study was carried out to evaluate the resistance of the glucosinolates to the digestive process. The application of pressurised liquid extraction to the recovery of glucosinolates from camelina sativa by-product, is a green, automatic, and rapid method, representing a valid alternative to conventional extraction method to obtain ingredients for food industries.

Moringa seeds are an excellent dietary source of phytochemicals (i.e., glucosinolates, GSLs; isothiocyanates, ITCs) with health-beneficial effects. Although numerous studies have been conducted on moringa seeds, the effect of germination on the regulation of GSLs remains scarcely explored. The present study investigated the dynamic changes of GSLs in moringa seeds during germination (at 25, 30, and 35 °C for 6 days in the dark) through an untargeted metabolomics approach and compared the antioxidant capacity of ungerminated and germinated moringa seeds. Our results showed that germination significantly increased the total GSL content from 150 (day 0) to 323 μmol/g (35 °C, day 6) on a dry weight (DW) basis, especially glucomoringin (GMG), the unique glucosinolate in moringa seeds, which was significantly upregulated from 61 (day 0) to 149 μmol/g DW (35 °C, day 4). The upregulation of GMG corresponded to the metabolism of tyrosine, which might be the initial precursor for the formation of GMG. In addition, germination enhanced the total ITC content from 85 (day 0) to 239 μmol SE/g DW (35 °C, day 6), indicating that germination may have also increased the activity of myrosinase. Furthermore, germination remarkably increased the total phenolic content (109-507 mg GAE/100 g DW) and antioxidant capacity of moringa seeds. Our findings suggest that moringa sprouts could be promoted as a novel food and/or ingredient rich in GMG.

Background: Multiple and simultaneous attacks by pathogens and insect pests frequently occur in nature. Plants respond to biotic stresses by activating distinct defense mechanisms, but little is known about how plants cope with multiple stresses. The focus of this study was the combined interaction of fungal infection caused by Leptosphaeria maculans (synonym Plenodomus lingam) and arthropod infestation by the diamondback moth (Plutella xylostella) in oilseed rape (Brassica napus). We hypothesized that infection by the fungal pathogen L. maculans could alter oilseed rape palatability to P. xylostella-chewing caterpillars. Feeding preference tests were complemented with analyses of defense gene transcription, and levels of glucosinolates (GLSs) and volatile organic compounds (VOCs) in L. maculans-inoculated and non-inoculated (control) leaves to determine possible causes of larval choice., Results: Caterpillars preferred true leaves to cotyledons, hence true leaves were used for further experiments. True leaves inoculated with L. maculans were more palatable to caterpillars over control leaves during the early stage of infection at 3 days post inoculation (dpi), but this preference disappeared in the later stages of infection at 7 dpi. In parallel, genes involved in the salicylic acid and ethylene pathways were up-regulated in L. maculans-inoculated leaves at 3 and 7 dpi; L. maculans increased the level of total aliphatic GLSs, specifically glucobrassicanapin, and decreased the level of glucoiberin at 3 dpi and altered the content of specific VOCs. A group of 55 VOCs with the highest variability between treatments was identified., Conclusion: We suggest that the P. xylostella preference for L. maculans-inoculated leaves in the early stage of disease development could be caused by the underlying mechanisms leading to changes in metabolic composition. Further research should pinpoint the compounds responsible for driving larval preference and evaluate whether the behavior of the adult moths, i.e. the stage that makes the first choice regarding host plant selection in field conditions, correlates with our results on larval host acceptance. © 2024 Society of Chemical Industry., (© 2024 Society of Chemical Industry.)

Two wild-growing Brassicaceae plants of Croatian origin, Aurinia leucadea (Guss.) K. Koch and Lepidium draba L., were investigated to uncover glucosinolates via GC/MS analysis of their degradation products. The main constituents of Aurinia leucadea (Guss.) K.Koch distillate were hex-5-enenitrile (28.8%) and but-3-enyl isothiocyanate (18.8%), while 4,5-epithiopentanenitrile (50%) and 5,6-epithiohexanenitrile (18.5%) were the main volatile compounds in autolysate. 4-(Methylsulfanyl)butyl isothiocyanate (96.4%) constituted almost the entire Lepidium draba L. distillate, while the autolysate was characterized by 4-(methylsulfinyl)butyl isothiocyanate (57.3%). So, regarding the glucosinolate degradation products, the main glucosinolates of A. leucadea were glucobrassicanapin and gluconapin, and of L. draba glucoerucin and glucoraphanin.

Abstract Background Wasabi, a Brassicaceae member, is well-known for its unique pungent and hot flavor which is produced from glucosinolate (GSL) degradation. Myrosinase (MYR) is a principle enzyme catalyzing the primary conversion of GSLs to GSL hydrolysis products (GHPs) which is responsible for plant defense system and food quality. Due to the limited information in relation to MYRs present in wasabi (Wasabia japonica M.), this study aimed to identify the MYR isogenes in W. japonica and analyze their roles in relation to GSL metabolism. Results In results, WjMYRI-1 was abundantly expressed in all organs, whereas WjMYRI-2 showed only trace expression levels. WjMYRII was highly expressed in the aboveground tissues. Interestingly, WjMYRII expression was significantly upregulated by certain abiotic factors, such as methyl jasmonate (more than 40-fold in petioles and 15-fold in leaves) and salt (tenfold in leaves). Young leaves and roots contained 97.89 and 91.17 µmol‧g−1 of GSL, whereas less GSL was produced in mature leaves and petioles (38.36 and 44.79 µmol‧g−1, respectively). Similar pattern was observed in the accumulation of GHPs in various plant organs. Notably, despite the non-significant changes in GSL production, abiotic factors treated samples enhanced significantly GHP content. Pearson’s correlation analysis revealed that WjMYRI-1 expression significantly correlated with GSL accumulation and GHP formation, suggesting the primary role of WjMYRI-1-encoding putative protein in GSL degradation. In contrast, WjMYRII expression level showed no correlation with GSL or GHP content, suggesting another physiological role of WjMYRII in stress-induced response. Conclusions In conclusions, three potential isogenes (WjMYRI-1, WjMYRI-2, and WjMYRII) encoding for different MYR isoforms in W. japonica were identified. Our results provided new insights related to MYR and GSL metabolism which are important for the implications of wasabi in agriculture, food and pharmaceutical industry. Particularly, WjMYRI-1 may be primarily responsible for GSL degradation, whereas WjMYRII (clade II) may be involved in other regulatory pathways induced by abiotic factors.

Gregarines are usually classified as parasites, but recent studies suggest that they should be viewed on a parasitism-mutualism spectrum and may even be seen as part of the gut microbiota of host insects. As such, they may also impact the consumption of their hosts and/or be involved in the digestion or detoxification of the host’s diet. To study such effects of a gregarine species on those traits in its host, the mustard leaf beetle (Phaedon cochleariae) was used. This beetle species feeds on Brassicaceae plants that contain glucosinolates, which form toxic compounds when hydrolyzed by myrosinases. We cleaned host eggs from gametocysts and spores and reinfected half of the larvae with gregarines, to obtain gregarine-free (G-) and gregarine-infected (G+) larvae. Growth and food consumption parameters of these larvae were assessed by rearing individuals on watercress (Nasturtium officinale, Brassicaceae). A potential involvement of gregarines in the glucosinolate metabolism of P. cochleariae larvae was investigated by offering G- and G+ larvae leaf discs of watercress (containing mainly the benzenic 2-phenylethyl glucosinolate and myrosinases) or pea (Pisum sativum, Fabaceae, lacking glucosinolates and myrosinases) treated with the aliphatic 4-pentenyl glucosinolate or the indole 1-methoxy-3-indolylmethyl glucosinolate. Larval and fecal samples were analyzed via UHPLC-QTOF-MS/MS to search for breakdown metabolites. Larval development, body mass, growth rate and efficiency to convert food into body mass were negatively affected by gregarine infection while the pupal mass remained unaffected. The breakdown metabolites of benzenic and aliphatic glucosinolates were conjugated with aspartic acid, while those of the indole glucosinolate were conjugated with glutamic acid. Gregarine infection did not alter the larvae’s ability to metabolize glucosinolates and was independent of plant myrosinases. In summary, some negative effects of gregarines on host performance could be shown, indicating parasitism. Future studies may further disentangle this gregarine-host relationship and investigate the microbiome potentially involved in the glucosinolate metabolism.

This study investigated the effect of salicylic acid (SA) treatment on preserving the color and nutritional quality of broccoli during postharvest cold storage. The results demonstrated that SA treatment significantly delayed the yellowing process, increased chlorophyll content, −a*/b* value, quantum yield (Fv/Fm), and fluorescence decline ratio (Rfd) and decreased L* value and yellowing index compared with untreated control. Meanwhile, the losses of glucoraphanin (GRA), glucobrassicin (GBS), sulforaphane (SFN), indole-3-methanol (I3C), and ascorbic acid (AsA) were obviously alleviated in the treated samples, and the accumulation of total phenols and total flavonoids was significantly increased. In addition, the total antioxidant capacity (T-AOC) of the treated samples was improved remarkably and the content of malondialdehyde (MDA) was significantly reduced. Multivariate statistical analysis visualized the distribution of sensory and nutritional variables in both groups of samples, further demonstrating that SA treatment was more effective in preserving GRA and AsA and effectively induced an improvement of the antioxidant capacity.

Radical difunctionalization of aliphatic alkynes provides direct access to valuable multi‐substituted alkenes, but achieving a high level of chemo‐ and stereo‐control remains a formidable challenge. Herein a novel photoredox neutral alkyne di‐functionalization is reported through functional group migration followed by a radical‐polar crossover and energy transfer‐enabled stereoconvergent isomerization of alkenes. In this sequence, a hydroxyalkyl and an aryl group are incorporated concomitantly into an alkyne, leading to diversely functionalized E‐allyl alcohols. The scope of alkynes is noteworthy, and the reaction tolerates aliphatic alkynes containing hydrogen donating C─H bonds that are prone to intramolecular hydrogen atom transfer. The protocol features broad functional group compatibility, high product diversity, and exclusive chemo‐ and stereoselectivity, thus providing a practical strategy for the elusive radical di‐functionalization of unactivated alkynes. [ABSTRACT FROM AUTHOR]

Kale is a functional food with anti-cancer, antioxidant, and anemia prevention properties. The harmful effects of the emerging pollutant microplastic (MP) on plants have been widely studied, but there is limited research how to mitigate MP damage on plants. Numerous studies have shown that Se is involved in regulating plant resistance to abiotic stresses. The paper investigated impact of MP and Se on kale growth, photosynthesis, reactive oxygen species (ROS) metabolism, phytochemicals, and endogenous hormones. Results revealed that MP triggered a ROS burst, which led to breakdown of antioxidant system in kale, and had significant toxic effects on photosynthetic system, biomass, and accumulation of secondary metabolites, as well as a significant decrease in IAA and a significant increase in GA. Under MP supply, Se mitigated the adverse effects of MP on kale by increasing photosynthetic pigment content, stimulating function of antioxidant system, enhancing secondary metabolite synthesis, and modulating hormonal networks., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

This study aimed to analyse the chemical profile and biological activities of 29 accessions of Brassica rapa (turnips) and 9 of Brassica napus (turnips and seeds) collections, maintained ex situ in Portugal. HPLC-HRMS allowed the determination of glucosinolates (GLS) and polyphenolic compounds. The antioxidant and antimicrobial activities were determined by using relevant assays. The chemical profiles showed that glucosamine, gluconasturtiin, and neoglucobrassin were the most abundant GLS in the extracts from the turnip accessions. Minor forms of GLS include gluconapoleiferin, glucobrassicanapin, glucoerucin, glucobrassin, and 4-hydroxyglucobrassin. Both species exhibited strong antioxidant activity, attributed to glucosinolates and phenolic compounds. The methanol extracts of Brassica rapa accessions were assessed against a panel of five Gram-negative bacteria (Enterobacter cloacae, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica subsp. enterica serovar, and Yersinia enterocolitica) and three Gram-positive bacteria (Bacillus cereus, Listeria monocytogenes, and Staphylococcus aureus). The extracts exhibited activity against S. enterica and S. aureus, and two showed inhibitory activity against E. coli and Y. enterocolitica. This study provides valuable insights into the chemical composition and biological properties of Brassica rapa and Brassica napus collections in Portugal. The selected accessions can constitute potential sources of natural antioxidants and bioactive compounds, which can be used in breeding programs and improving human health and to promote healthy food systems. [ABSTRACT FROM AUTHOR]

6-(Methylsulfinyl)hexyl isothiocyanate (6-MSITC), a derivative of glucosinolate with a six-carbon chain, is a compound found in wasabi and has diverse health-promoting properties. The biosynthesis of glucosinolates from methionine depends on a crucial step catalyzed methylthioalkylmalate synthases (MAMs), which are responsible for the generation of glucosinolates with varying chain lengths. In this study, our primary focus was the characterization of two methylthioalkyl malate synthases, MAM1-1 and MAM1-2, derived from Eutrema japonicum, commonly referred to as Japanese wasabi. Eutremajaponicum MAMs (EjMAMs) were expressed in an Escherichiacoli expression system, subsequently purified, and in vitro enzymatic activity was assayed. We explored the kinetic properties, optimal pH conditions, and cofactor preferences of EjMAMs and compared them with those of previously documented MAMs. Surprisingly, EjMAM1-2, categorized as a metallolyase family enzyme, displayed 20% of its maximum activity even in the absence of divalent metal cofactors or under high concentrations of EDTA. Additionally, we utilized AlphaFold2 to generate structural homology models of EjMAMs, and used in silico analysis and mutagenesis studies to investigate the key residues participating in catalytic activity. Moreover, we examined in vivo biosynthesis in E. coli containing Arabidopsis thaliana branched-chain amino acid transferase 3 (AtBCAT3) along with AtMAMs or EjMAMs and demonstrated that EjMAM1-2 exhibited the highest conversion rate among those MAMs, converting l-methionine to 2-(2-methylthio) ethyl malate (2-(2-MT)EM). EjMAM1-2 shows a unique property in vitro and highest activity on converting l-methionine to 2-(2-MT)EM in vivo which displays high potential for isothiocyanate biosynthesis in E. coli platform., (Copyright © 2024 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.)

The precipitation and deposition of waxes in high waxy crude oil often result in the low throughput and clogging of pipeline. Adding polymers is a practical approach to solve these problems. In this study, poly(styrene-co-docosyl maleate) s (PSDMs) were synthesized by reversible addition-fragmentation chain transfer polymerization. The chemical structure and molecular weight of copolymers were characterized using Fourier infrared spectroscopy, 1H nuclear magnetic resonance spectroscopy, and gel permeation chromatography. The ratio of phenyl to aliphatic branches varies from 10:8 to 25:8. The crystallization and morphology of waxes in model oil were investigated by x-ray diffraction, differential scanning calorimetry, and polarized light microscopy. The cold flow behaviors of crude oil were evaluated by rheological methods. With the increase of the ratio of phenyl to aliphatic branches, the crystallinity, viscosity, and yield stress of crude oil first increase and then decrease. In the presence of PSDM-2, the crystallinity and enthalpy of phase transition (H) are reduced by 44.2% and 48.9%. Thus, the pour point, viscosity, and yield stress of crude oil are reduced by 6.0°C, 76.8% and 77.4%, respectively. Therefore, welldefined PSDMs are promising to be remarkable flow improvers for waxy crude oils. [ABSTRACT FROM AUTHOR]

The precision control of monodisperse nanomaterials with spatially distinct functionalities and properties is of particular interest in materials science. Creating biocompatible/biodegradable nanoparticles that can be colloidally stable in aqueous solution further paves the way to a broad range of bio-related applications. In present work, we demonstrate the precise fabrication of aliphatic polycarbonate based one-dimensional (1D) cylinders and 2D platelet micelles using living crystallization-driven self-assembly (CDSA) by seeded growth method. By synthesizing aliphatic polycarbonate core-forming block copolymers with different corona-to-core ratios, excellent control over dimensions of 1D cylinders and 2D platelets with good uniformity is achieved through effectively epitaxial growth in ethanol based on the mass ratios of unimer-to-seed. Meanwhile, segmented nanoparticles with spatially-defined chemistries can further be prepared by sequential seeded growth approach. Moreover, these 1D/2D nanostructures are colloidally stable in water, and further show excellently biocompatible property towards L929 cells. These promising properties of polycarbonate-based micelles enable to a wide application as cargo vehicles in bio-related fields. [Display omitted] • Aliphatic polycarbonate core-forming block copolymers are prepared via sequential polymerizations. • Uniform 2D platelets are created by seeded growth using a BCP with short corona-to-core ratio. • 1D cylinders with low dispersity in length are fabricated by seeded growth using a BCP with long corona-to-core ratio. • The 1D and 2D nanostructures are colloidally stable in water and show excellent biocompatibility towards L929 cells. [ABSTRACT FROM AUTHOR]

Brassica vegetables are widely consumed all over the world, especially in North America, Asia, and Europe. They are a rich source of sulfur compounds, such as glucosinolates (GLSs) and isothiocyanates (ITCs), which provide health benefits but are also suspected of having a goitrogenic effect. Adhering to PRISMA guidelines, we conducted a systematic review to assess the impact of dietary interventions on thyroid function, in terms of the potential risk for people with thyroid dysfunctions. We analyzed the results of 123 articles of in vitro, animal, and human studies, describing the impact of brassica plants and extracts on thyroid mass and histology, blood levels of TSH, T3, T4, iodine uptake, and the effect on thyroid cancer cells. We also presented the mechanisms of the goitrogenic potential of GLSs and ITCs, the limitations of the studies included, as well as further research directions. The vast majority of the results cast doubt on previous assumptions claiming that brassica plants have antithyroid effects in humans. Instead, they indicate that including brassica vegetables in the daily diet, particularly when accompanied by adequate iodine intake, poses no adverse effects on thyroid function.

Abstract Background Brassicas (Brassicaceae) are recognized as excellent sources of nutrients and bioactive compounds. Among these, wild turnip (Brassica rapa L.), holds significant promising nutritional properties owed to its abundant glucosinolates and phenolic compounds. To enhance its potential values, the application of elicitors is crucial and good strategy prompting an enrichment in the concentration of phytochemicals, as well established in other relevant Brassicas, such as broccoli. While the responses triggered by certain elicitors such as salicylic acid, methyl jasmonate, or chitosan are widely documented, little is known about the impact of electrolyzed water, an economically viable elicitor. Through elicitation strategies, the aim of this work was to unravel insights into enhancing the phytochemical content of wild turnip sprouts for potential use as healthy food, comparing with well-studied broccoli as control of the experiments. Results Our findings revealed that wild turnip exhibited a notable higher glucosinolate (GSL) contents (487–712 mg 100 g−1 D.W.), than in broccoli sprouts. Furthermore, the use of electrolyzed water (2 vol.) boosted the accumulation of glucosinolates with significant increase up to twofolds the content. Specifically, treatments with salicylic acid (250 μM) and electrolyzed water (2 vol.) favored the significant increase of mainly aliphatic GSL (progoitrin, PRO; gluconapin, GNA; glucobrassicin, GBN). On the other hand, natural antioxidants such as of the characteristic acylated cyanidins present in wild turnip sprouts were not affected by the elicitor treatments, indicative of higher tolerance to oxidative stress in wild turnip. Conclusions These observations underlined the potential of using electrolyzed water in wild turnips as elicitor for GSL-enriched food ingredients. Further studies will be necessary to align with the broader goal of evaluating abiotic and biotic factors affecting the phytochemical composition in mature organs not only in germinating seeds and sprouts, for agricultural performance for quality and healthy foods purposes. Graphical Abstract

This study aimed to analyse the chemical profile and biological activities of 29 accessions of Brassica rapa (turnips) and 9 of Brassica napus (turnips and seeds) collections, maintained ex situ in Portugal. HPLC-HRMS allowed the determination of glucosinolates (GLS) and polyphenolic compounds. The antioxidant and antimicrobial activities were determined by using relevant assays. The chemical profiles showed that glucosamine, gluconasturtiin, and neoglucobrassin were the most abundant GLS in the extracts from the turnip accessions. Minor forms of GLS include gluconapoleiferin, glucobrassicanapin, glucoerucin, glucobrassin, and 4-hydroxyglucobrassin. Both species exhibited strong antioxidant activity, attributed to glucosinolates and phenolic compounds. The methanol extracts of Brassica rapa accessions were assessed against a panel of five Gram-negative bacteria (Enterobacter cloacae, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica subsp. enterica serovar, and Yersinia enterocolitica) and three Gram-positive bacteria (Bacillus cereus, Listeria monocytogenes, and Staphylococcus aureus). The extracts exhibited activity against S. enterica and S. aureus, and two showed inhibitory activity against E. coli and Y. enterocolitica. This study provides valuable insights into the chemical composition and biological properties of Brassica rapa and Brassica napus collections in Portugal. The selected accessions can constitute potential sources of natural antioxidants and bioactive compounds, which can be used in breeding programs and improving human health and to promote healthy food systems.

The production of double haploids ("DH") by microspore-derived embryos is one of the best breeding methods to generate new varieties with better traits and stable genetic background. In the previous study, radish 'DH' lines were generated with a different range of glucosinolate (GSL) contents, ranging from low to high levels of GSL. In this study, we performed metabolic and transcriptional profiling to elucidate the regulatory system behind the GSL biosynthesis process using the 'DH' radish lines. Four individual 'DH' lines were selected, of which two lines named 'HH' had high GSL content, while the other two lines, 'LL', had low GSL content. HPLC analysis in the vegetative (leaf and root) and reproductive tissue (seed) was detected seven GSL compounds from radish. Among seven GSLs, glucoraphasatin (GRH) occupied the largest proportion of total GSLs in both leaf and root tissues, while glucoraphenin (GRE) was taking a place as the major GSL in radish seeds. Six major genes (RsBCAT4, RsIPMDH1, RsCYP79F1, RsCYP83A1, RsUGT74B1, and RsGRS1) representing the major biosynthesis of aliphatic GSLs were selected for qRT-PCR analysis. Heat map analysis based on Pearson correlation coefficient showed that RsBCAT4, RsIPMDH1, RsCYP79F1, and RsCYP83A1 were positively correlated with the amount of GRH in leaf tissue. Meanwhile, RsGRS1 showed a strong correlation with the amount of GRH and total aliphatic GSLs in both leaf and root tissues. By using the 'DH' radish lines, this study revealed that regardless of tissues of radish, accumulation of total GSL is strongly affected by the RsGRS1 and also positively supported by the other biosynthetic genes like RsBCAT4, RsIPMDH1, RsCYP79F1, and RsCYP83A1. [ABSTRACT FROM AUTHOR]

We previously found that feeding rats with broccoli or cauliflower leads to the formation of characteristic DNA adducts in the liver, intestine and various other tissues. We identified the critical substances in the plants as 1-methoxy-3-indolylmethyl (1-MIM) glucosinolate and its degradation product 1-MIM-OH. DNA adduct formation and the mutagenicity of 1-MIM-OH in cell models were drastically enhanced when human sulfotransferase (SULT) 1A1 was expressed. The aim of this study was to clarify the role of SULT1A1 in DNA adduct formation by 1-MIM-OH in mouse tissues in vivo. Furthermore, we compared the endogenous mouse Sult1a1 and transgenic human SULT1A1 in the activation of 1-MIM-OH using genetically modified mouse strains. We orally treated male wild-type (wt) and Sult1a1-knockout (ko) mice, as well as corresponding lines carrying the human SULT1A1-SULT1A2 gene cluster (tg and ko-tg), with 1-MIM-OH. N2-(1-MIM)-dG and N6-(1-MIM)-dA adducts in DNA were analysed using isotope-dilution UPLC-MS/MS. In the liver, caecum and colon adducts were abundant in mice expressing mouse and/or human SULT1A1, but were drastically reduced in ko mice (1.2–10.6% of wt). In the kidney and small intestine, adduct levels were high in mice carrying human SULT1A1-SULT1A2 genes, but low in wt and ko mice (1.8–6.3% of tg-ko). In bone marrow, adduct levels were very low, independently of the SULT1A1 status. In the stomach, they were high in all four lines. Thus, adduct formation was primarily controlled by SULT1A1 in five out of seven tissues studied, with a strong impact of differences in the tissue distribution of mouse and human SULT1A1. The behaviour of 1-MIM-OH in these models (levels and tissue distribution of DNA adducts; impact of SULTs) was similar to that of methyleugenol, classified as "probably carcinogenic to humans". Thus, there is a need to test 1-MIM-OH for carcinogenicity in animal models and to study its adduct formation in humans consuming brassicaceous foodstuff. [ABSTRACT FROM AUTHOR]

Brassica crops are well known for the accumulation of glucosinolates—secondary metabolites crucial for plants' adaptation to various stresses. Glucosinolates also functioning as defence compounds pose challenges to food quality due to their goitrogenic properties. Their disruption leaves plants susceptible to insect pests and diseases. Hence, a targeted reduction in seed glucosinolate content is of paramount importance to increase food acceptance. GLUCOSINOLATE TRANSPORTERS (GTRs) present a promising avenue for selectively reducing glucosinolate concentrations in seeds while preserving biosynthesis elsewhere. In this study, 54 putative GTR protein sequences found in Brassica were retrieved, employing Arabidopsis GTR1 and GTR2 templates. Comprehensive bioinformatics analyses, encompassing gene structure organization, domain analysis, motif assessments, promoter analysis, and cis-regulatory elements, affirmed the existence of transporter domains and stress-related regulatory elements. Phylogenetic analysis revealed patterns of conservation and divergence across species. Glucosinolates have been shown to increase under stress conditions, indicating a potential role in stress response. To elucidate the role of GTRs in glucosinolate transportation under NaCl stress in two distinct Brassica species, B. juncea and B. napus, plants were subjected to 0, 100, or 200 mM NaCl. Based on the literature, key GTR genes were chosen and their expression across various plant parts was assessed. Both species displayed divergent trends in their biochemical profiles as well as glucosinolate contents under elevated salt stress conditions. Statistical modelling identified significant contributors to glucosinolate variations, guiding the development of targeted breeding strategies for low-glucosinolate varieties. Notably, GTR2A2 exhibited pronounced expressions in stems, contributing approximately 52% to glucosinolate content variance, while GTR2B1/C2 displayed significant expression in flowers. Additionally, GTR2A1 and GTR1A2/B1 demonstrated noteworthy expression in roots. This study enhances our understanding of glucosinolate regulation under stress conditions, offering avenues to improve Brassica crop quality and resilience. [ABSTRACT FROM AUTHOR]

Lepidium draba (hoary cress) is a perennial plant belonging to the Brassicaceae family that produces two dominant glucosinolates (GLSs): glucoraphanin (GRN) and sinalbin (SBN). They represent the stored form, which is converted upon the myrosinase (Myr) hydrolysis activity to active compounds, mainly isothiocyanates (ITCs) such as sulforaphane (SFN) or p-hydroxybenzyl isothiocyanate (pHBITC). Research on ITCs that have proven anticancer, antimicrobial, and chemoprotective properties is usually conducted with pure commercially available compounds. However, these are chemically reactive, making it difficult to use them directly for preventive purposes in dietary supplements. Efforts are currently being made to prepare dietary supplements enriched with GLS and/or Myr. In this study, we report a simple but efficient chromatographic procedure for the isolation and purification of GLSs from MeOH extract from hoary cress based on a combination of ion exchange and gel permeation chromatography on DEAE-Sephadex A-25 and Sephadex LH-20. To obtain the Myr required for efficient hydrolysis of GLSs into antibacterial ITCs, we developed a rapid method for its extraction from the seeds of Lepidium sativum (garden cress). The yields of GLSs were 22.9 ± 1.2 mg GRN (purity 96%) and 10.4 ± 1.1 mg SBN (purity 92%) from 1 g of dry plant material. Both purified GLSs were used as substrates for the Myr. Analysis of the composition of hydrolysis products (HPs) revealed differences in their hydrolysis rates and in the degree of conversion from GLSs to individual ITCs catalyzed by Myr. When GRNs were cleaved, SFNs were formed in an equimolar ratio, but the formation of pHBITCs was only half that of cleaved SBNs. The decrease in pHBITC content is due to its instability compared to SFN. While SFN is stable in aqueous media during the measurement, pHBITC undergoes non-enzymatic hydrolysis to p-hydroxybenzyl alcohol and thiocyanate ions. Testing of the antimicrobial effects of the HPs formed from GRN by Myr under premix or in situ conditions showed inhibition of the growth of model prokaryotic and eukaryotic microorganisms. This observation could serve as the jumping-off point for the design of a two-component mixture, based on purified GLSs and Myr that is, usable in food or the pharmaceutical industry in the future. [ABSTRACT FROM AUTHOR]

Non‐native annual grasses have invaded western rangelands in the United States, and novel approaches are needed to supplement existing management strategies. The aim of this study was to investigate biofumigation, the use of Brassicaceae products to suppress weeds, as a control for two non‐native annual grasses (cheatgrass, Bromus tectorum and ventenata, Ventenata dubia) and its effects on two dominant native perennial grasses (bluebunch wheatgrass, Pseudoroegneria spicata and Idaho fescue, Festuca idahoensis). We tested the effect of the biofumigant Brassica juncea (brown mustard), applied as seed meal and mulch, on germination metrics of the four grass species in Petri dishes. Germination metrics included emergence and viability, time to cotyledon and radicle emergence and their lengths at 14 days after sowing. Impacts on emergence and viability were assessed using a binomial mixed effects model, while time to cotyledon and radicle emergence and lengths were assessed using linear mixed effects models. Seed meal reduced emergence and viability at lower application rates for V. dubia and F. idahoensis than the other two species. Mulch did not consistently reduce emergence or viability. P. spicata was the least inhibited by the biofumigants. When using seed meal, radicle emergence and length were inhibited in B. tectorum, V. dubia and F. idahoensis and cotyledon emergence and length were inhibited for all. The mulch did not impact these metrics consistently and may not be a viable management tool. The use of seed meal biofumigant to suppress undesired annual grasses in rangelands seems promising, but response is species‐specific. [ABSTRACT FROM AUTHOR]

Here, we characterized the independent role of soil microbiomes (bacterial and fungal communities) in determining the flavor chemistry of harvested mustard seed (Brassica juncea). Given the known impacts of soil microbial communities on various plant characteristics, we hypothesized that differences in rhizosphere microbiomes would result in differences in seed flavor chemistry (glucosinolate content). In a glasshouse study, we introduced distinct soil microbial communities to mustard plants growing in an otherwise consistent environment. At the end of the plant life cycle, we characterized the rhizosphere and root microbiomes and harvested produced mustard seeds for chemical characterization. Specifically, we measured the concentrations of glucosinolates, secondary metabolites known to create spicy and bitter flavors. We examined associations between rhizosphere microbial taxa or genes and seed flavor chemistry. We identified links between the rhizosphere microbial community composition and the concentration of the main glucosinolate, allyl, in seeds. We further identified specific rhizosphere taxa predictive of seed allyl concentration and identified bacterial functional genes, namely genes for sulfur metabolism, which could partly explain the observed associations. Together, this work offers insight into the potential influence of the belowground microbiome on the flavor of harvested crops., (© 2024 The Authors. New Phytologist © 2024 New Phytologist Foundation.)

The cultivation of Camelina sativa (L.) Crantz is rapidly increasing due to oil production resulting in a substantial volume of by-products, which still have an interesting composition in secondary metabolites, especially glucosinolates. Therefore, a green extraction procedure of glucosinolates by Pressurised Liquid Extraction was developed and optimized using a chemometric approach. Furthermore, the glucosinolates were purified by solid phase extraction, and a preliminary study on bioaccessibility and bioavailability study was carried out to evaluate the resistance of the glucosinolates to the digestive process. The application of pressurised liquid extraction to the recovery of glucosinolates from camelina sativa by-product, is a green, automatic, and rapid method, representing a valid alternative to conventional extraction method to obtain ingredients for food industries., Competing Interests: The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (© 2024 The Authors.)

Brevicoryne brassicae , an aphid species, exclusively consumes plants from the Brassicaceae family and employs a sophisticated defense mechanism involving a myrosinase enzyme that breaks down glucosinolates obtained from its host plants. In this work, we employed combined quantum mechanical and molecular mechanical (QM/MM) calculations and molecular dynamics (MD) simulations to study the catalytic reaction of aphid myrosinase. A proper QM region to study the myrosinase reaction should contain the whole substrate, models of Gln-19, His-122, Asp-124, Asn-166, Glu-167, Lys-173, Tyr-180, Val-228, Tyr-309, Tyr-346, Ile-347, Glu-374, Glu-423, Trp-424, and a water molecule. The calculations show that Asp-124 and Glu-423 must be charged, His-122 must be protonated on NE2, and Glu-167 must be protonated on OE2. Our model reproduces the anomeric retaining characteristic of myrosinase and indicates that the deglycosylation reaction is the rate-determining step of the reaction. Based on the calculations, we propose a reaction mechanism for aphid myrosinase-mediated hydrolysis of glucosinolates with an overall barrier of 15.2 kcal/mol. According to the results, removing a proton from Arg-312 or altering it to valine or methionine increases glycosylation barriers but decreases the deglycosylation barrier. The proposed computational-based mechanism for aphid myrosinase unveils novel insights into its catalytic process using QM/MM modeling. [Display omitted] [ABSTRACT FROM AUTHOR]

This study explored the glucosinolate (GSL) content in Brassica plants and utilized in silico analysis approach to assess their antioxidant capabilities. GSLs, present abundantly in Brassica vegetables, offer potential health advantages, including antioxidant effects. Employing Ultra-Performance Liquid Chromatography (UPLC) coupled with tandem mass spectrometry (MS/MS), major GSLs were identified in 89 accessions from diverse species and subspecies. Statistical analysis and principal component analysis unveiled significant GSL variation and potential correlations among the Brassica germplasms. This study unveils the dominance of aliphatic GSLs over aromatic and indolyl compounds in all the accessions. Notably, Gluconapin (GNA) (33,049.23 µmol·kg -1 DW), Glucobrassicanapin (GBN) (9803.82 µmol·kg -1 DW), Progoitrin (PRO) (12,780.48 µmol·kg -1 DW) and Sinigrin (SIN) (14,872.93 µmol·kg -1 DW) were the most abundant compounds across the analyzed accessions. Moreover, in silico docking studies predicted promising antioxidant activity by evaluating the interactions of each GSL with antioxidant enzymes. Specifically, Sinigrin and Gluconapin exhibited a notably weaker influence on antioxidant enzymes. This provides key insights into the antioxidant potential of Brassica germplasm and highlights the importance of in silico analysis for evaluating bioactive properties. In general, the results of this study could be utilized in breeding programs to maximize GSL levels and antioxidant properties in Brassica crops and for developing functional foods with enhanced health benefits.

Glucosinolates, the main secondary metabolites accumulated in cruciferous flora, have a major impact on fortifying plant immunity against diverse pathogens. Although Botrytis cinerea exhibits varying sensitivity to these compounds, current research has yet to fully understand the intricate mechanisms governing its response to glucosinolates. Different species of the genus Botrytis were exposed to glucosinolate-derived isothiocyanates, revealing that B. fabae, B. deweyae, and B. convolute, species with the mfsG transporter gene (Bcin06g00026) not detected with PCR, were more sensitive to isothiocyanates than Botrytis species containing that gene, such as B. cinerea, B. pseudocinerea, and B. byssoidea. This finding was further corroborated by the inability of species with the mfsG gene not detected with PCR to infect plants with a high concentration of glucosinolate-derived isothiocyanates. These results challenge established correlations, revealing varying aggressiveness on different plant substrates. An expression analysis highlighted the gene's induction in the presence of isothiocyanate, and a bioinformatic investigation identified homologous genes in other Botrytis species. Our study underscored the importance of advanced biotechnology to help understand these proteins and thus offer innovative solutions for agriculture. [ABSTRACT FROM AUTHOR]

Grafting is an effective horticultural method to reduce Cd accumulation in crops. However, the mechanism of grafting inducing the decrease in Cd content in scions remains unclear. This study evaluated the effect of grafting on fruit quality, yield, and Cd content of Solanum melongena, and explored the potential mechanism of grafting reducing Cd content in scions. In the low Cd-contaminated soil, compared with un-grafted (UG) and self-grafted plants (SG), the fruit yield of inter-grafted plants (EG) increased by 38 %, and the fruit quality was not markedly affected. In EG, the decrease in total S and Cd content was not related to organic acids and thiol compounds. The decrease in total S and Cd content in EG leaves and fruits was closely related to the synthesis and transportation of glucosinolates (GSL). The genes encoding GSL synthesis in leaves, such as basic helix-loop-helix, myelocytomatosis proteins, acetyl-CoA, cytochrome P450, and glutathione S-transferases, were significantly downregulated. In EG leaves, the contents of five of the eight amino acids involved in GSL synthesis decreased significantly (P < 0.05). Notably, total GSL in EG stems, leaves, and fruits had a significant linear correlation with total S and Cd. In summary, the decrease in total S and Cd content in scions caused by grafting is closely related to GSL. Our findings provide a theoretical basis for the safe use of Cd-contaminated soil, exploring the long-distance transport of Cd in plants and cultivating crops with low Cd accumulation., Competing Interests: Declaration of competing interest The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2024 Elsevier B.V. All rights reserved.)

The adverse effects of arsenic-chelating drugs make it essential to replace invasive chelating therapy with non-invasive oral therapy for arsenic poisoning. The goal of the current investigation was to determine whether the uterine damage caused by arsenization could be repaired by the n-butanol fraction of Moringa oleifera seed (NB). The rats were orally administered with arsenic (10 mg/kg BW) for the initial 8 days, followed by NB (50 mg/kg) for the next 8 days without arsenic. The probable existence of different components in NB was evaluated by HPLC–MS. Pro and anti-inflammatory indicators were assessed by RT-PCR and western blot. ESR-α was detected via immunostaining. Arsenic-exposed rats had significantly increased lipid peroxidation and decreased antioxidant enzyme activity, which were markedly reduced after NB treatment. Weaker ESR-α expression and distorted uterine histomorphology following arsenication were retrieved significantly by NB. Meaningful restoration by NB was also achieved for altered mRNA and protein expression of various inflammatory and apoptotic indicators. Molecular interaction predicted that glucomoringin and methyl glucosinolate of moringa interact with the catalytic site of caspase-3 in a way that limits its activity. However, NB was successful in restoring the arsenic-mediated uterine hypofunction. The glucomoringin and methyl glucosinolate present in n-butanol fraction may play a critical role in limiting apoptotic event in the arsenicated uterus. [ABSTRACT FROM AUTHOR]

This study investigated the impact of Methyl Jasmonate (MeJA) application on the nutritional content and yield of five different colored radish microgreens. Microgreens were produced without substrate and subjected to 0.5 mM and 1.0 mM MeJA treatments on the 7th day, three days before harvest. The parameters measured included yield, dry matter, minerals, amino acids, secondary metabolites such as chlorophylls (Chls), anthocyanins, flavonoids, phenolics, glucosinolates (GSLs), vitamin C, and antioxidant capacity. MeJA at 1.0 mM generally improved yield and dry weight across cultivars, and all microgreens exhibited rich mineral and amino acid composition, with the influence of cultivar being more significant than MeJA treatment. However, MeJA enhanced all cultivars' anthocyanins, GSLs, phenolics, flavonoids, and antioxidant activities. Generally, as the antioxidant capacity is the primary factor influencing the nutritional quality of microgreens, MeJA-treated microgreens, especially with selected superior cultivars such as 'Asia purple' and 'Koregon red', could offer a potential for cultivation of value-added, eco-friendly microgreens with substrate-free cultivation.

This study investigated the impact of plasma-activated water (PAW) on Raphanus sativus (radish) roots at the level of proteins and metabolites. PAW treatment induced the accumulation of reactive oxygen species (ROS) and nitrogen oxide species (NO x ) in radish and enhanced the activities of antioxidant enzymes. Proteomic analysis resulted in the identification of 6054 proteins, including 1845 PAW-modulated proteins that were majorly associated with energy metabolism, ROS-detoxification, phytohormones signaling, and biosynthesis of glucosinolates. Subsequent metabolomics analysis identified 314 metabolites, of which 194 showed significant differences in response to PAW treatment. In particular, PAW treatment triggered the accumulation of functional compounds such as vitamin C, vitamin B5, glutathione, and glucosinolates, the well-known characteristic compounds of the Brassicaceae family. Further, integrating proteomics and metabolomics data provided novel insights into the molecular mechanism governing plasma-induced growth and the accumulation of these functional compounds in radish plants., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023 Elsevier Ltd. All rights reserved.)

In this paper, we take a historical perspective by going back to Verschaffelt's landmark study published in 1910, in which he found that glucosinolates were used as token stimuli by larvae of Pieris butterflies, specialist feeders on plants in the family Brassicaceae. This classic discovery provided key evidence for Fraenkel (Science 129:1466-1470, 1959) to elaborate on the function of secondary plant substances and for Ehrlich and Raven (Evolution 18:586-608, 1964) to put forward the hypothesis of insect-plant coevolution. The discovery by Schoonhoven (Kon Nederl Akad Wetensch Amsterdam Proc Ser C70:556-568, 1967) of taste neurons highly sensitive to glucosinolates in Pieris brassicae was an important milestone in elucidating the chemosensory basis of host-plant specialization. The molecular basis of glucosinolate sensitivity was elucidated recently (Yang et al., PLoS Genet 17, 2021) paving the way to unravel the evolution of gustatory receptors tuned to glucosinolates that are crucial for host-plant selection of Pieris butterflies. We propose a hypothetical model for the evolution of labeled-line neurons tuned to token stimuli., (© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)

Plants produce a myriad of specialized compounds in response to threats such as pathogens or pests and different abiotic factors. The stress-related induction of specialized metabolites can be mimicked using silver nitrate (AgNO 3 ) as an elicitor, which application in conservation agriculture has gained interest. In Arabidopsis thaliana, AgNO 3 triggers the accumulation of indole glucosinolates (IGs) and the phytoalexin camalexin as well as pheylpropanoid-derived defensive metabolites such as coumaroylagmatins and scopoletin through a yet unknown mechanism. In this work, the role of jasmonic (JA) and salicylic acid (SA) signaling in the AgNO 3 -triggered specialized metabolite production was investigated. To attain this objective, AgNO 3 , MeJA and SA were applied to A. thaliana lines impaired in JA or SA signaling, or affected in the endogenous levels of IGs and AGs. Metabolomics data indicated that AgNO 3 elicitation required an intact JA and SA signaling to elicit the metabolic response, although mutants impaired in hormone signaling retained certain capacity to induce specialized metabolites. In turn, plants overproducing or abolishing IGs production had also an altered hormonal signaling response, both in the accumulation of signaling molecules and the molecular response mechanisms (ORA59, PDF1.2, VSP2 and PR1 gene expression), which pointed out to a crosstalk between defense hormones and specialized metabolites. The present work provides evidence of a crosstalk mechanism between JA and SA underlying AgNO 3 defense metabolite elicitation in A. thaliana. In this mechanism, IGs would act as retrograde feedback signals dampening the hormonal response; hence, expanding the signaling molecule concept., Competing Interests: Declaration of competing interest The authors declare no conflict of interest., (Copyright © 2024 The Authors. Published by Elsevier Masson SAS.. All rights reserved.)

Salt stress substantially leads to flowering delay. The regulation of salt-induced late flowering has been studied at the transcriptional and protein levels; however, the involvement of secondary metabolites has rarely been investigated. Here, we report that FMO GS-OX s (EC 1.14.13.237), the enzymes that catalyze the biosynthesis of glucosinolates (GSLs), promote flowering transition in Arabidopsis thaliana. It has been reported that WRKY75 is a positive regulator, and MAF4 is a negative regulator of flowering transition. The products of FMO GS-OX s, methylsulfinylalkyl GSLs (MS GSLs), facilitate flowering by inducing WRKY75 and repressing the MAS-MAF4 module. We further show that the degradation of MS GSLs is involved in salt-induced late flowering and salt tolerance. Salt stress induces the expression of myrosinase genes, resulting in the degradation of MS GSLs, thereby relieving the promotion of WRKY75 and inhibition of MAF4, leading to delayed flowering. In addition, the degradation products derived from MS GSLs enhance salt tolerance. Previous studies have revealed that FMO GS-OX s exhibit alternative catalytic activity to form trimethylamine N-oxide (TMAO) under salt stress, which activates multiple stress-related genes to promote salt tolerance. Therefore, FMO GS-OX s integrate flowering transition and salt tolerance in various ways. Our study shed light on the functional diversity of GSLs and established a connection between flowering transition, salt resistance, and GSL metabolism., (© 2024 Scandinavian Plant Physiology Society.)

This study explored the glucosinolate (GSL) content in Brassica plants and utilized in silico analysis approach to assess their antioxidant capabilities. GSLs, present abundantly in Brassica vegetables, offer potential health advantages, including antioxidant effects. Employing Ultra-Performance Liquid Chromatography (UPLC) coupled with tandem mass spectrometry (MS/MS), major GSLs were identified in 89 accessions from diverse species and subspecies. Statistical analysis and principal component analysis unveiled significant GSL variation and potential correlations among the Brassica germplasms. This study unveils the dominance of aliphatic GSLs over aromatic and indolyl compounds in all the accessions. Notably, Gluconapin (GNA) (33,049.23 µmol·kg−1 DW), Glucobrassicanapin (GBN) (9803.82 µmol·kg−1 DW), Progoitrin (PRO) (12,780.48 µmol·kg−1 DW) and Sinigrin (SIN) (14,872.93 µmol·kg−1 DW) were the most abundant compounds across the analyzed accessions. Moreover, in silico docking studies predicted promising antioxidant activity by evaluating the interactions of each GSL with antioxidant enzymes. Specifically, Sinigrin and Gluconapin exhibited a notably weaker influence on antioxidant enzymes. This provides key insights into the antioxidant potential of Brassica germplasm and highlights the importance of in silico analysis for evaluating bioactive properties. In general, the results of this study could be utilized in breeding programs to maximize GSL levels and antioxidant properties in Brassica crops and for developing functional foods with enhanced health benefits.

Glucosinolates is a class of secondary metabolites with anti-inflammatory and anti-obesity properties and an intense bitter taste in tumorous stem mustard (TSM), which are used to produce a famous pickle named Zhacai. Spectrophotometric, chromatographic, or infrared techniques showed capacity to evaluate glucosinolate level. The aim of current study was to improve a spectrophotometric methodology to quantify total glucosinolates content (TGC) in TSM. Microwave treatment at medium temperature for 20 s was used to improve the previous method of water bath in enzyme inactivation. Absorbance should be tested at 420 nm for measuring TGC, while not 450 nm. The optimized extraction conditions of glucosinolates were that solid-liquid ratio was 1:22; temperature was 60°C; time was 30 min. The regression curve used for TGC calculation was made using a variety of individual glucosinolate. Recovery rate and variable coefficient of TGC quantitation in TSM were 103% and 5.98%. These results obtained by this method have high consistency within 3 days. In addition, we also introduced the limitations of this method. [ABSTRACT FROM AUTHOR]

• Non-enzymatic nitrile formation from glucosinolates in red cabbage is pH dependent. • Thermal stability of glucosinolates is mediated by different additives. • Amines formed from isothiocyanates are major hydrolysis products of glucosinolates. • Methylsulfinylalkyl amine levels increased during prolonged boiling of red cabbage. • Four different N , N '-dialkyl thioureas were quantified in boiled red cabbage. Red cabbage is a popular vegetable in Central Europe and a rich source of glucosinolates (GLSs). Upon hydrolysis, GLSs form health-promoting isothiocyanates (ITCs), but also nitriles and epithionitriles. Recently, ITCs were shown to undergo further hydrolysis, yielding amines. Here, we analyzed the degradation of GLSs and the formation of ITCs, nitriles, epithionitriles, and amines during domestic-like cooking of red cabbage with addition of vinegar or baking soda. Both additives strongly affected the stability of GLSs and the formation of nitriles during boiling. Primary amines were found as a major degradation product of GLSs. In control and vinegar samples, formation of methylsulfinylalkyl amines increased during boiling. Additionally, for the first time, the formation of several N , N '-dialk(en)yl thioureas during boiling of Brassica vegetables was demonstrated, resulting from the reaction of GLS-derived ITCs and amines, and they were subsequently quantified. As references, five N , N '-dialk(en)yl thioureas were synthesized and characterized by NMR and HRMS. [ABSTRACT FROM AUTHOR]

[Display omitted] • 29 types of individual glucosinolates were identified via widely targeted metabolomics. • GER were firstly affirmed in rapeseed materials. • GER could generate volatile 5-methylthio-pentanenitrile and 4-pentenonitrile. • 4-isothiocyanato-1-butene and dimethyl trisulfide provide pungent and cabbage notes. The degradation products of glucosinolates endow rapeseed oil with a characteristic aroma, however, the mechanism remains unclear. In this study, 29 individual glucosinolates were identified in six rapeseeds (Brassica napus) using widely targeted metabolism, including 22 aliphatic, 5 aromatic, and 2 indole glucosinolates. Characterization of thermally induced aromas from new precursors-glucoerucin was performed in different pH matrices via headspace-solid phase microextraction and gas chromatography-mass spectrometry. Six glucoerucin degradation were identified including 5-methylthio-pentanenitrile and dimethyl trisulfide et al. The results of thermal model showed that Glucoerucin could generate volatile 5-methylthio-pentanenitrile via dehydration and formed 1-isothiocyanato-4-(methylsulfanyl)butane via (394.9 μg/kg) by the Rosen rearrangement further product pungent odors 4-isothiocyanato-1-butene (5.6 μg/kg) at pH 5. Sulfur-containing compounds included dimethyl disulfide and dimethyl trisulfide can provide pungent and cabbage notes in matrices at pH 7 and 9. The results provide a new understanding in the forming mechanism of characteristic odor in fragrant rapeseed oil. [ABSTRACT FROM AUTHOR]

Sulfur containing compounds including glucosinolates (GLS), sulforaphane (SFN) and S-methyl-l-cysteine sulfoxide (SMCSO) have been proposed to be partly responsible for the beneficial health effects of cruciferous vegetables. As such, greater understanding of their measurements within foods is important to estimate intake in humans and to inform dietary intervention studies. Herein is described a simple and sensitive method for simultaneous analysis of 20 GLS, SFN and SMCSO by liquid chromatography mass spectrometry. Analytes were effectively retained and resolved on an Xbridge C18 column. Detection can be achieved using high resolution or unit resolution mass spectrometry; the latter making the method more applicable to large studies. Quantitative analysis using calibration standards was demonstrated for 10 GLS, SFN and SMCSO. A further 10 GLS were tentatively identified using high resolution mass spectrometry. The use of surrogate GLS standards was shown to be unreliable, with closely related GLS displaying significantly different ionisation efficiencies.

Glucosinolates (GLSs) are a well-studied sulfur-containing compound found in Brassicaceae plants that play critical roles in plant resistance and human health. Correctly identifying and reliably quantifying the total and individual GLS content is of great importance. An improved method as an alternative to the ISO 9167-1 (ISO) method is developed in the present study. An efficient extraction and purification procedure is proposed with a commercially available dimethylaminopropyl (DEA)-based weak anion exchange solid-phase extraction (SPE) cartridge instead of using the self-prepared ion-exchange columns in the ISO method. The GLSs are identified and quantified by ultra high-performance liquid chromatography (UHPLC) high-resolution mass spectrometry (HRMS). The method demonstrates a comparable quantification of total and individual GLSs on certified rapeseeds and other Brassicaceae vegetables when compared to the ISO method. The developed SPE method is simpler and more efficient, thus allowing for applications to a large sample size with reduced analysis time, improved repeatability and accuracy, and possible automation. [ABSTRACT FROM AUTHOR]

Broccoli is a popular cruciferous vegetable that is well known for its abundant health-promoting biochemicals. The most important of these beneficial biochemicals are glucosinolates, including glucoraphanin and glucobrassicin. Glucoraphanin and glucobrassicin can be broken down by myrosinases into sulforaphane and indole-3-carbinol, which have been demonstrated to have potent cancer-preventive properties. Efforts to increase glucoraphanin in broccoli seedlings have long been a focus; however, increasing glucoraphanin and glucobrassicin simultaneously, as well as enhancing myrosinase activity to release more sulforaphane and indole-3-carbinol, have yet to be investigated. This study aims to investigate the impact of the combined application of tryptophan and methionine on the accumulation of sulforaphane and indole-3-carbinol, as well as their precursors. Furthermore, we also examined whether this application has any effects on seedling growth and the presence of other beneficial compounds. We found that the application of methionine and tryptophan not only increased the glucoraphanin content by 2.37 times and the glucobrassicin content by 3.01 times, but that it also caused a higher myrosinase activity, resulting in a1.99 times increase in sulforaphane and a 3.05 times increase in indole-3-carbinol. In addition, better plant growth and an increase in amino acids and flavonoids were observed in broccoli seedlings with this application. In conclusion, the simultaneous application of tryptophan and methionine to broccoli seedlings can effectively enhance their health-promoting value and growth. Our study provides a cost-effective and multi-benefit strategy for improving the health value and yield of broccoli seedlings, benefiting both consumers and farmers. [ABSTRACT FROM AUTHOR]

This study investigated the impact of Methyl Jasmonate (MeJA) application on the nutritional content and yield of five different colored radish microgreens. Microgreens were produced without substrate and subjected to 0.5 mM and 1.0 mM MeJA treatments on the 7th day, three days before harvest. The parameters measured included yield, dry matter, minerals, amino acids, secondary metabolites such as chlorophylls (Chls), anthocyanins, flavonoids, phenolics, glucosinolates (GSLs), vitamin C, and antioxidant capacity. MeJA at 1.0 mM generally improved yield and dry weight across cultivars, and all microgreens exhibited rich mineral and amino acid composition, with the influence of cultivar being more significant than MeJA treatment. However, MeJA enhanced all cultivars’ anthocyanins, GSLs, phenolics, flavonoids, and antioxidant activities. Generally, as the antioxidant capacity is the primary factor influencing the nutritional quality of microgreens, MeJA-treated microgreens, especially with selected superior cultivars such as ‘Asia purple’ and ‘Koregon red’, could offer a potential for cultivation of value-added, eco-friendly microgreens with substrate-free cultivation.