Glucosinolate Degradation Research Articles

Enhancing the formation of functional glucosinolate degradation products in fermented broccoli stalk by-product with lactic acid bacteria

Broccoli stalk by-product (BsBP) is rich in glucosinolates (GSLs). Its fermentation process is generally characterized by the degradation of GSLs and formation of bioactive isothiocyanates (ITCs), in which lactic acid bacteria (LAB) play an important role. The GSLs-degrading capacity of 61 LAB strains was investigated in vitro. Lacticaseibacillus paracasei YC5, Pediococcus pentosaceus RBHZ36, and Lactiplantibacillus plantarum ND1, with high potential to transform GSLs into ITCs, were screened. The functional GSL degradation products (total content of sulforaphane, indol-3-carbinol, and ascorbigen) increased 22.0–33.5 % compared to natural fermentation after 24 h when BsBP was fermented by the three screened strains in pure culture. LAB fermentation also helped to increase the quantity of indolic GSL degradation products in BsBP brine, suggesting that LAB fermentation promoted BsBP GSLs transformation into bioactive ITCs. The proposed use of the LAB strains characterized in this study provided a fermented BsBP and brine with high profile of functional GSL degradation products.

Screening of glucosinolates degrading lactic acid bacteria and their utilization in rapeseed meal fermentation

Rapeseed meal is a promising food ingredient, but its utilization is limited by the presence of some potentially harmful ingredients, such as glucosinolates. Fermentation is a cost-effective method of detoxication but a food-grade starter culture with glucosinolates degradation capacity is required. In this study, 46 strains of lactic acid bacteria from traditional paocai brines were screened for their ability to glucosinolate degradation. The results showed that more than 50% of the strains significantly degraded glucosinolates. Two strains of Lactiplantibacillus (p7 and s7) with high capacity of glucosinolates degradation through producing enzymes were identified. Then, an optimized condition for rapeseed meal fermentation by p7 was established to degrade glucosinolates, which can achieve about 80% degradation. UPLC/Q-TOF-MS analysis showed that the degradation rate of individual glucosinolates was different and the degradation rate of gluconapin and progoitrin in rapeseed meal can reach more than 90%. Meanwhile, fermentation with p7 can improve safety of rapeseed meal by inhibiting the growth of Enterobacteriaceae and improve its nutritional properties by degrading phytic acid. The in vitro digestion experiments showed that the content of glucosinolates in rapeseed meal decreased significantly during gastric digestion. Meanwhile, fermentation with p7 can greatly improve the release of soluble protein and increase the contents of free essential amino acids, such as lysine (increased by 12 folds) and methionine (increased by 10 folds).

Electrochemical advanced oxidation of glucosinolates derived from rapeseed meal: Parameter optimization, degradation mechanism and toxicity assessment

Glucosinolates (GLS) are a group of antinutritional compounds present in rapeseed meal that limit its use as feed ingredients. Considering their potentially hazardous effects on both the aquatic environment and animal health, it is necessary to develop green and efficient degradation options for GLS. In the current work, the electrochemical advanced oxidation technology with a boron-doped diamond (BDD) electrode was initially employed for the degradation of GLS. To facilitate parameter optimization, a sequential strategy comprising a definitive screening design and a central composite rotatable design was implemented. Particular attention was paid to the differing roles of five electrolyte salts (NaCl, NaNO3, Na2SO4, NaHCO3 and Na3PO4) during the electrolytic oxidations. The optimal conditions for GLS degradation were found to be a flow rate of 400 mL min−1, a applied current density of 7.75 mA cm−2 and a 2.0 mM NaNO3 medium, yielding mineralization of 82.2 % at 120 min of electrolysis. By combining the results of computational simulation and LC/MS analysis, four possible degradation pathways of allyl GLS at the BDD anode were proposed. And the ecotoxicity of each detected degradation product was determined using the ECOSAR program. Further biological toxicity assay revealed that crude GLS electrolysis reduced the toxicity on model organism Caenorhabditis elegans, reducing its death percentage by 26.80 % and its lipofuscin level by 37.59 % at 48 h. The results showed great promise of BDD technology in engineering applications as a powerful option for the treatment of GLS derived from rapeseed meal.

Myrosinase isogenes in wasabi (Wasabia japonica Matsum) and their putative roles in glucosinolate metabolism

BackgroundWasabi, 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.ResultsIn 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.ConclusionsIn 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.

Glucosinolate extract from radish (Raphanus sativus L.) seed attenuates high-fat diet-induced obesity: insights into gut microbiota and fecal metabolites.

Radish seed is a functional food with many beneficial health effects. Glucosinolates are characteristic components in radish seed that can be transformed into bioactive isothiocyanates by gut microbiota. The present study aims to assess anti-obesity efficacy of radish seed glucosinolates (RSGs) and explored the underlying mechanisms with a focus on gut microbiota and fecal metabolome. High-fat diet-induced obese mice were supplemented with different doses of RSGs extract for 8 weeks. Changes in body weight, serum lipid, alanine aminotransferase (ALT), and aspartate aminotransferase (AST) levels; and pathological changes in the liver and adipose tissue were examined. Fecal metabolome and 16S rRNA gene sequencing were used to analyze alterations in fecal metabolite abundance and the gut microbiota, respectively. Results showed that RSG extract prevented weight gain and decreased serum lipid, ALT, AST levels and lipid deposition in liver and epididymal adipocytes in obese mice. Treatment with RSG extract also increased gut microbiota diversity and altered the dominant bacteria genera in the gut microbiota, decreasing the abundance of Faecalibaculum and increasing the abundance of Allobaculum, Romboutsia, Turicibacter, and Akkermansia. Fecal metabolome results identified 570 differentially abundant metabolites, of which glucosinolate degradation products, such as sulforaphene and 7-methylsulfinylheptyl isothiocyanate, were significantly upregulated after RSG extract intervention. Furthermore, enrichment analysis of metabolic pathways showed that the anti-obesity effects of RSG extract may be mediated by alterations in bile secretion, fat digestion and absorption, and biosynthesis of plant secondary metabolites. Overall, RSG extract can inhibit the development of obesity, and the obesity-alleviating effects of RSG are related to alternative regulation of the gut microbiota and glucosinolate metabolites.

Degradation of glucosinolates and formation of isothiocyanates, nitriles, amines, and N,N’-dialk(en)yl thioureas during domestic boiling of 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.

A novel infrared roasting to improve the flavour profile of virgin rapeseed oils

SummaryIn this work, a novel roasting method for virgin rapeseed oil (VRO) production was proposed. The effect of infrared roasting (IR) on oxidation stability, Maillard reaction, glucosinolate degradation and volatiles of VRO was evaluated at 110–170 °C. The results showed that VROs from IR exhibited better oxidation stability (higher oxidative stability index and DPPH radical scavenging activity) of VROs than that from traditional roller roasting (TRR). This was attributed to the higher contents of tocopherols (748.78 mg kg−1) and canolol (680.69 mg kg−1) measured in IR‐VROs than tocopherols (682.15 mg kg−1) and canolol (564.28 mg kg−1) in TRR‐VROs. IR could provide a more effective thermal fracture of rapeseed, facilitating to higher releases of tocopherols and canolol. Moreover, during IR, free amino acid (from 25.60 to 15.03 mg kg−1), reducing sugars (from 7.65 to 2.04 mg kg−1) and glucosinolate (from 28.73 to 13.00 mg kg−1) were decreased more than TRR, especially at 150 °C, indicating more intense Maillard reaction and glucosinolate degradation. Hence, more nitriles/isothiocyanates (657.43 μg kg−1) and pyrazines (269.64 μg kg−1) were generated in IR‐VROs than TRR‐VROs (600.82 and 163.89 μg kg−1, respectively). From sensory analysis, the flavour profile of IR‐VRO was more than TRR‐VRO at 150 °C. IR holds the potential to produce VROs with better flavours.

Microbial degradation of plant toxins.

Plants produce a variety of secondary metabolites in response to biotic and abiotic stresses. Although they have many functions, a subclass of toxic secondary metabolites mainly serve plants as deterring agents against herbivores, insects, or pathogens. Microorganisms present in divergent ecological niches, such as soil, water, or insect and rumen gut systems have been found capable of detoxifying these metabolites. As a result of detoxification, microbes gain growth nutrients and benefit their herbivory host via detoxifying symbiosis. Here, we review current knowledge on microbial degradation of toxic alkaloids, glucosinolates, terpenes, and polyphenols with an emphasis on the genes and enzymes involved in breakdown pathways. We highlight that the insect-associated microbes might find application in biotechnology and become targets for an alternative microbial pest control strategy.

Thermal degradation and oxidation of glucosinolates in model systems and Brassica vegetable broth is mediated by redox-active compounds

Glucosinolates (GLSs) are secondary plant metabolites with health-promoting effects found in Brassica vegetables. Recently, next to non-enzymatic degradation yielding nitriles, 4-(methylthio)butyl GLS (4MTB-GLS) was shown to undergo side chain oxidation during thermal treatment, forming 4-(methylsulfinyl)butyl GLS (4MSOB-GLS). Here, we investigated natural plant components and artificial analogs on their capability of altering the thermal reactivity of 4MTB-GLS in vegetable broths and model systems using buffers. Addition of ascorbic acid and dehydroascorbic acid caused varying effects: in broth samples, it increased nitrile formation, while in buffer, 4MSOB-GLS was formed. In further experiments, the antioxidant compounds quercetin and Trolox triggered the side chain oxidation of 4MTB-GLS, while H2S terminated its degradation. A synergistic effect of ascorbic acid and Fe2+ was observed, degrading 98% of 4MTB-GLS to the nitrile after 60 min of boiling. Deepening the understanding of factors that influence the non-enzymatic degradation of GLSs will help to preserve their health-promoting effects.

Nitrile-Specific Protein NSP2 and Its Interacting Protein MPK3 Synergistically Regulate Plant Disease Resistance in Arabidopsis.

Glucosinolates and their degradation products have a wide range of actions and are important components of plant defense. NSP2 (nitrile-specific protein 2) is a key regulator in the breakdown process of glucosinolates. However, the precise function of NSP2 in plant disease resistance beyond its role in glucosinolate degradation is still unclear. In this study, we discovered that NSP2 which was induced by Pst DC3000, influenced PR genes expression and reactive oxygen burst. Additionally, omics analysis revealed that NSP2 was engaged in plant-pathogen interaction and several hormone signal transduction pathways. Furthermore, immunoprecipitation-tandem mass spectrometry analysis (IP-MS), bimolecular fluorescence complementation (BiFC), and co-immunoprecipitation demonstrated that NSP2 interacts with MPK3. Genetic analysis shows that NSP2 may be a function downstream of MPK3. Upon pathogen inoculation, NSP2 protein levels increase while MPK3 protein levels decrease. Moreover, the level of phosphorylated NSP2 decreases. Taken together, this study sheds light on a new mode of synergistic action between NSP2 and MPK3 in the disease resistance process.

A novel type of sprout food development: Effects of germination on phytic acid, glucosinolates, and lipid profiles in rapeseed

Germination, a new processing technology, is widely used to improve the nutritional value of plant seeds. Cereals and legumes sprouts are widely popular around the world. In this study, a novel form of sprouts-based rapeseed was produced. Germination promoted the degradation of phytic acid and glucosinolates (GLs) in rapeseed. On the fourth day of germination, the degradation rate of phytic acid in rapeseed was nearly 80%, and the degradation rate of GLs reached more than 90%. The changes in lipid species and content by sprouting were assessed. The crude fat content was significantly reduced during rapeseed germination. Using non-targeted lipidomics, three hundred eighty-nine lipid molecules in 4 categories and 17 subclasses were identified in rapeseed/rapeseed sprouts. Glycerides were most abundant, followed by fatty acids, glycerophospholipids, and sphingolipids. Germination affected not only the lipid content but also its composition. Some functional lipids (such as FAHFAs) were generated and enriched during germination. The content of monounsaturated fatty acids first raised and then decreased during germination. The finding will serve as a theoretical reference for developing novel sprouts based on rapeseed, furnish primary data concerning the nutritional content of rapeseed sprouts, and provide fresh ideas for rapeseed resource exploitation.

Insight into the microwave pretreatment of rapeseeds on the flavor characteristics of rapeseed oils

Microwave heating is a new technique employed for the pretreatment of rapeseed oil (RO) and can vary RO flavor with different processing time. This study investigated the flavor characteristics of RO from microwaved rapeseeds with different processing time using scanning electron microscope (SEM), electronic nose (E-nose) and two-dimensional gas chromatography coupled with headspace solid-phase micro-extraction and mass spectrometry (HS-SPME-GC×GC-MS). SEM results show that microwave pretreatment induced cell swelling and disintegration, forming a creased surface of rapeseeds. E-nose found that W1W, W1S, W2W and W5S were the main sensors to distinguish the RO flavors. HS-SPME-GC×GC-MS detected a total of 333 volatile compounds with 105 key aroma compounds in ROs. The longer microwave pretreatment, the more volatile compounds formed, especially heterocyclic compounds and glucosinolate degradation compounds. In general, ROs were classified as: 0–3 min of green and woody flavors, 4–6 min of oxidized flavor and 7–10 min of smoky, roasted and pungent flavors. Microwave of 4–6 min was considered as the transitional state from 0-3 min to 7–10 min, and 10 min was regarded as an overheated sample distinguishable from other ROs.

Immunomodulatory and Antioxidant Effects of Spray-Dried Encapsulated Kale Sprouts after In Vitro Gastrointestinal Digestion.

The health-related compounds present in kale are vulnerable to the digestive process or storage conditions. Encapsulation has become an alternative for their protection and takes advantage of their biological activity. In this study, 7-day-old Red Russian kale sprouts grown in the presence of selenium (Se) and sulfur (S) were spray-dried with maltodextrin to assess their capacity to protect kale sprout phytochemicals from degradation during the digestion process. Analyses were conducted on the encapsulation efficiency, particle morphology, and storage stability. Mouse macrophages (Raw 264.7) and human intestinal cells (Caco-2) were used to assess the effect of the intestinal-digested fraction of the encapsulated kale sprout extracts on the cellular antioxidant capacity, the production of nitric oxide (NOx), and the concentrations of different cytokines as indicators of the immunological response. The highest encapsulation efficiency was observed in capsules with a 50:50 proportion of the hydroalcoholic extract of kale and maltodextrin. Gastrointestinal digestion affected compounds' content in encapsulated and non-encapsulated kale sprouts. Spray-dried encapsulation reduced the phytochemicals' degradation during storage, and the kale sprouts germinated with S and Se showed less degradation of lutein (35.6%, 28.2%), glucosinolates (15.4%, 18.9%), and phenolic compounds (20.3%, 25.7%), compared to non-encapsulated ones, respectively. S-encapsulates exerted the highest cellular antioxidant activity (94.2%) and immunomodulatory activity by stimulating IL-10 production (88.9%) and COX-2 (84.1%) and NOx (92.2%) inhibition. Thus, encapsulation is an effective method to improve kale sprout phytochemicals' stability and bioactivity during storage and metabolism.

Overexpression of LSU1 and LSU2 confers cadmium tolerance by manipulating sulfur metabolism in Arabidopsis

Phytoremediation using plants is an environmentally friendly and cost-effective strategy for removing cadmium (Cd) from soil. Plants used for phytoremediation must have a high Cd accumulation capacity and strong Cd tolerance. Therefore, understanding the molecular mechanism of Cd tolerance and accumulation in plants is of great interest. In response to Cd exposure, plants produce various thio-rich compounds, such as glutathione, phytochelatins, and metallothioneins, which play important roles in Cd immobilization, sequestration, and detoxification. Therefore, sulfur (S) metabolism is crucial for Cd tolerance and accumulation. In this study, we report that the overexpression of low-S responsive genes, LSU1 and LSU2, confers Cd tolerance in Arabidopsis. First, LSU1 and LSU2 promoted S assimilation under Cd stress. Second, LSU1 and LSU2 inhibited the biosynthesis and promoted the degradation of aliphatic glucosinolates, which could limit the consumption and enhance the release of S, thus, facilitating the production of the S-rich metabolites, glutathione, phytochelatins, and metallothioneins. We further demonstrated that the Cd tolerance mediated by LSU1 and LSU2 was dependent on the myrosinases BGLU28 and BGLU30, which catalyze the degradation of aliphatic glucosinolates. In addition, the overexpression of LSU1 and LSU2 improved Cd accumulation, which has great potential for the phytoremediation of Cd-contaminated soil.

Thermal processing-induced changes in volatilome and metabolome of Brussels sprouts: focus on glucosinolate metabolism

This study aimed to investigate the influence of different thermal treatment methods (boiling, steaming) on the metabolome and volatilome of Brussels sprouts. Targeted, quantitative analysis of primary metabolites (amino acids and sugars), glucosinolates as well as untargeted analysis of volatile organic compounds (VOCs) were performed. The composition of primary metabolites was affected only by boiling, where the loss of nutrients was observed. Glucosinolate content increased after cooking, which can be explained by the loosening of the plant tissues and its better extractability. Most marked changes were noticed in the volatilome. Among the degradation products of glucosinolates, isothiocyanates were the main chemical group in the raw and boiled vegetable. In contrast, steaming favored the formation of nitriles. Another dominant group of VOCs were aldehydes, which were the most abundant in raw Brussels sprouts and their level significantly decreased after thermal treatment. It is well known that isothiocyanates are substances with widely proven bioactive properties. Therefore, their formation in the glucosinolate degradation process is favorable. Based on the obtained results, it was concluded that boiling seems to be the most beneficial form of Brussels sprouts’ processing.

Identification of glucosinolates and volatile odor compounds in microwaved radish (Raphanus sativus L.) seeds and the corresponding oils by UPLC-IMS-QTOF-MS and GC × GC-qMS analysis

The effect of microwave treatment on the content of glucosinolates (GSL) in radish seeds and volatile odor compounds in the microwaved radish seed oils (MRSO) is still unclear. In this study, a total of 13 GSL were identified and quantified in five radish seed varieties by UPLC-IMS-QTOF-MS, among which glucoraphenin, glucoraphasatin, glucoerucin accounting for up to 90 %. Total GSL decreased by 47.39–67.88% after microwave processing. Moreover, 58 odor compounds were identified in MRSO, including 6 sulfides, 12 nitriles, 2 isothiocyanates, 10 alcohols, 12 aldehydes, 5 ketones, 6 acids, and 5 others. The major odor compounds were (methyldisulfanyl)methane, dimethyltrisulfane, (methylsulfinyl)methane, 3-(methylsulfanyl)-1-propanol, methyl thiocyanate, hexanenitrile, 5-(methylsulfanyl)pentanenitrile, and 4-isothiocyanato-1-butene with odor activity value (OAV) higher than 1. The principal components analysis (PCA) results can distinguish MRSO from five different radish seed varieties, three of which (H20-18, H20-19 and H20-28) were in one group and other two (H20-23 and H20-26) were in another group. In addition, aliphatic GSL showed positive correlations with sulfides, isothiocyanates, and nitriles, while negative correlations with alcohols. This work provides a new insight into the odor contribution of GSL degradation products.

Glucosinolates, a natural chemical arsenal: More to tell than the myrosinase story.

Glucosinolates are a group of thioglucosides that belong to the class of plant nitrogen-containing natural products. So far, very little biological activity has been associated with intact glucosinolates. The hydrolysis of glucosinolates has, for long, attracted attention because of the potent biological activity of the hydrolysis products. From allelopathic to antiparasitic, antimicrobial and antineoplastic effects, the activity spectrum of the degradation products of typical glucosinolates has been the subject of much research. The present review seeks to address the various means of glucosinolate degradation (thermal, enzymatic, or chemical degradation) and the ensuing products. It also aims to draw a comparative profile of the various antimicrobial effects of these degradation products to provide a further understanding of the biological function of these important compounds.

Variation in glucosinolates and the formation of functional degradation products in two Brassica species during spontaneous fermentation

Vegetables from the Brassica species are excellent sources of glucosinolates (GLSs), the precursors of health-promoting isothiocyanates (ITCs). Fermentation enhances the biotransformation of GLSs into potential bioactive ITCs. To explore the biotransformation of GLSs during Brassica fermentation, the changes in GLSs during the fermentation of two Brassica species (i.e., cauliflower and broccoli); the formation of corresponding breakdown products; and the shifts in physicochemical parameters, bacterial communities, and myrosinase activities involved in GLSs degradation were systematically investigated. Nine aliphatic, three indolic, and two benzenic GLSs were identified in fermented cauliflower (FC) and fermented broccoli (FB). Aliphatic glucoiberin and glucoraphanin were the major forms of GLS in FC and FB, respectively; indolic glucobrassicin was also abundant in both FC and FB. The total GLS content decreased by 85.29% and 65.48% after 3 d of fermentation in FC and FB, respectively. After 2 d of fermentation, a significant increase in bioactive GLS degradation products (P < 0.05), including sulforaphane (SFN), iberin (IBN), 3,3-diindolylmethane (DIM), and ascorbigen (ARG), was observed in FC and FB compared to in fresh cauliflower and broccoli. Moreover, variations in pH value and titratable acidity in FC and FB correlated with Brassica fermentation and were accomplished by lactic acid bacteria, including Weissella, Lactobacillus-related genera, Leuconostoc, Lactococcus, and Streptococcus. These changes may enhance the biotransformation of GSLs to ITCs. Overall, our results indicate fermentation leads to the degradation of GLSs and the accumulation of functional degradation products in FC and FB.

Comprehensive two-dimensional gas chromatography-time of flight mass spectrometry as a tool for tracking roasting-induced changes in the volatilome of cold-pressed rapeseed oil

The aim of this study was to track changes in the volatilome of cold-pressed oil and press cakes obtained from roasted seeds and to combine it with the profile of non-volatile metabolites in a single study, in order to understand pathways of volatile organic compound (VOC) formation caused by thermal processing. Comprehensive two-dimensional gas chromatography-time of flight mass spectrometry was used for the analysis of VOCs in cold-pressed oils and corresponding press cakes obtained after roasting of seeds at 140 and 180 °C prior to pressing. Contents of primary metabolites (amino acids, saccharides, fatty acids) as well as selected secondary metabolites (glucosinolates, polyphenols) were determined, as many of them serve as precursors to volatile compounds formed especially in thermal reactions. After roasting, the formation of Maillard reaction products increased, which corresponded to the reduction of free amino acids and monosaccharides. Moreover, levels of the products of thermal oxidation of fatty acids, such as aldehydes and ketones, increased with the increasing temperature of roasting, although no significant changes were noted for fatty acids. Among sulphur-containing compounds, contents of the products and intermediates of methionine Strecker degradation increased significantly with the increasing temperature of roasting. Degradation of glucosinolates to nitriles occurred after thermal treatment. The results of this study confirmed that seed roasting before cold pressing has a significant effect on the volatiles, but also indicated roasting-induced changes in non-volatile metabolites of oil and press cake. Such an approach helps to understand metabolic changes occurring during rapeseed processing in cold-pressed oil production.Graphical

Plant matrix concentration and redox status influence thermal glucosinolate stability and formation of nitriles in selected Brassica vegetable broths

Brassica vegetables are frequently consumed foods of nutritional interest, because they are rich in glucosinolates (GLSs). Among GLS breakdown products, especially isothiocyanates are known for their health-beneficial effects, while nitriles are less beneficial. To increase the understanding of the plant matrix’s influence on GLS degradation, differently concentrated vegetable broths were prepared from selected Brassica vegetables (kohlrabi and red cabbage) and subsequently boiled. Altogether, heat stability and conversion of GLSs to the corresponding nitriles were both strongly influenced by vegetable type and plant matrix concentration in the broths. After boiling kohlrabi broths for 120 min, recovery of 4-(methylthio)butyl-GLS as nitrile was 55.5 % in 1 g/mL broth and 8.4 % in 0.25 g/mL broth. In follow-up experiments, a pronounced influence of the matrix’s redox status was identified, with H2S being an important factor. A better understanding of these processes will help to preserve health-promoting effects of GLSs in Brassica vegetables in the future.