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Keywords = epithionitrile

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12 pages, 4405 KiB  
Article
Integrative Analyses of Metabolites and Transcriptome Reveal the Metabolic Pattern of Glucosinolates in Potherb Mustard (Brassica juncea var. multiceps)
by Jie Wang, Shunhao Yu, Xiliang Ren, Yating Wang, Zhongrui Wang, Qiufeng Meng, Yunping Huang and Yuhong Wang
Plants 2024, 13(17), 2481; https://doi.org/10.3390/plants13172481 - 5 Sep 2024
Viewed by 1275
Abstract
Potherb mustard (Brassica juncea var. multiceps) is one of the most commonly consumed leafy vegetable mustards, either fresh or in pickled form. It is rich in glucosinolates, whose hydrolyzed products confer potherb mustard’s distinctive flavor and chemopreventive properties. In this study, [...] Read more.
Potherb mustard (Brassica juncea var. multiceps) is one of the most commonly consumed leafy vegetable mustards, either fresh or in pickled form. It is rich in glucosinolates, whose hydrolyzed products confer potherb mustard’s distinctive flavor and chemopreventive properties. In this study, the composition and content of glucosinolates, as well as the hydrolysis pattern of sinigrin were investigated in potherb mustard leaves of different varieties. Variations in the glucosinolate profile and accumulation were observed among the potherb mustard varieties studied, with sinigrin being the predominant one in all varieties, accounting for 81.55% to 97.27%. Sinigrin tended to be hydrolyzed to isothiocyanate (ITC) rather than epithionitrile (EPN) in potherb mustard, while 3-butenyl nitrile (SIN-NIT) could be hardly detected. Transcriptome analysis revealed a higher expression level of numerous genes involved in aliphatic glucosinolate biosynthesis in X11 compared to X57, corresponding to the higher aliphatic glucosinolate accumulation in X11 (91.07 µmol/g) and lower level in X57 (25.38 µmol/g). ESM1 is known to repress nitrile formation and favor isothiocyanate production during glucosinolate hydrolysis. In this study, all four ESM1s showed a higher expression level in X11 compared to X57, which may determine the hydrolysis pattern of sinigrin in potherb mustard. Altogether, our findings shed light on the glucosinolate metabolic pattern in potherb mustard, which will also facilitate the engineering of metabolic pathways at key checkpoints to enhance bioactive compounds for tailored flavor or pharmaceutical needs. Full article
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16 pages, 2936 KiB  
Article
Genome-Wide Identification and Expression Analysis of ESPs and NSPs Involved in Glucosinolate Hydrolysis and Insect Attack Defense in Chinese Cabbage (Brassica rapa subsp. pekinensis)
by Danni Han, Jingru Tan, Zhichen Yue, Peng Tao, Juanli Lei, Yunxiang Zang, Qizan Hu, Huasen Wang, Shizhong Zhang, Biyuan Li and Yanting Zhao
Plants 2023, 12(5), 1123; https://doi.org/10.3390/plants12051123 - 2 Mar 2023
Cited by 3 | Viewed by 2275
Abstract
Glucosinolates are secondary plant metabolites that are part of the plant’s defense system against pathogens and pests and are activated via enzymatic degradation by thioglucoside glucohydrolases (myrosinases). Epithiospecifier proteins (ESPs) and nitrile-specifier proteins (NSPs) divert the myrosinase-catalyzed hydrolysis of a given glucosinolate to [...] Read more.
Glucosinolates are secondary plant metabolites that are part of the plant’s defense system against pathogens and pests and are activated via enzymatic degradation by thioglucoside glucohydrolases (myrosinases). Epithiospecifier proteins (ESPs) and nitrile-specifier proteins (NSPs) divert the myrosinase-catalyzed hydrolysis of a given glucosinolate to form epithionitrile and nitrile rather than isothiocyanate. However, the associated gene families have not been explored in Chinese cabbage. We identified three ESP and fifteen NSP genes randomly distributed on six chromosomes in Chinese cabbage. Based on a phylogenetic tree, the ESP and NSP gene family members were divided into four clades and had similar gene structure and motif composition of Brassica rapa epithiospecifier proteins (BrESPs) and B. rapa nitrile-specifier proteins (BrNSPs) in the same clade. We identified seven tandem duplicated events and eight pairs of segmentally duplicated genes. Synteny analysis showed that Chinese cabbage and Arabidopsis thaliana are closely related. We detected the proportion of various glucosinolate hydrolysates in Chinese cabbage and verified the function of BrESPs and BrNSPs in glucosinolate hydrolysis. Furthermore, we used quantitative RT-PCR to analyze the expression of BrESPs and BrNSPs and demonstrated that these genes responded to insect attack. Our findings provide novel insights into BrESPs and BrNSPs that can help further promote the regulation of glucosinolate hydrolysates by ESP and NSP to resist insect attack in Chinese cabbage. Full article
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28 pages, 5389 KiB  
Review
Role of Sulfur Compounds in Vegetable and Mushroom Aroma
by Monika A. Marcinkowska and Henryk H. Jeleń
Molecules 2022, 27(18), 6116; https://doi.org/10.3390/molecules27186116 - 19 Sep 2022
Cited by 53 | Viewed by 6253
Abstract
At the base of the food pyramid is vegetables, which should be consumed most often of all food products, especially in raw and unprocessed form. Vegetables and mushrooms are rich sources of bioactive compounds that can fulfill various functions in plants, starting from [...] Read more.
At the base of the food pyramid is vegetables, which should be consumed most often of all food products, especially in raw and unprocessed form. Vegetables and mushrooms are rich sources of bioactive compounds that can fulfill various functions in plants, starting from protection against herbivores and being natural insecticides to pro-health functions in human nutrition. Many of these compounds contain sulfur in their structure. From the point of view of food producers, it is extremely important to know that some of them have flavor properties. Volatile sulfur compounds are often potent odorants, and in many vegetables, belonging mainly to Brassicaeae and Allium (Amaryllidaceae), sulfur compounds determine their specific flavor. Interestingly, some of the pathways that form volatile sulfur compounds in vegetables are also found in selected edible mushrooms. The most important odor-active organosulfur compounds can be divided into isothiocyanates, nitriles, epithionitriles, thiols, sulfides, and polysulfides, as well as others, such as sulfur containing carbonyl compounds and esters, R-L-cysteine sulfoxides, and finally heterocyclic sulfur compounds found in shiitake mushrooms or truffles. This review paper summarizes their precursors and biosynthesis, as well as their sensory properties and changes in selected technological processes. Full article
(This article belongs to the Special Issue Volatile Sulfur Compounds in Food Flavours)
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24 pages, 3394 KiB  
Article
The Impact of Domestic Cooking Methods on Myrosinase Stability, Glucosinolates and Their Hydrolysis Products in Different Cabbage (Brassica oleracea) Accessions
by Omobolanle O. Oloyede, Carol Wagstaff and Lisa Methven
Foods 2021, 10(12), 2908; https://doi.org/10.3390/foods10122908 - 24 Nov 2021
Cited by 17 | Viewed by 3751
Abstract
Glucosinolate hydrolysis products are responsible for the health-promoting properties of Brassica vegetables. The impact of domestic cooking on the myrosinase stability, glucosinolates and hydrolysis products in 18 cabbage accession was investigated. Cabbages were steamed, microwaved, and stir-fried before analysis. Cooking significantly affected myrosinase [...] Read more.
Glucosinolate hydrolysis products are responsible for the health-promoting properties of Brassica vegetables. The impact of domestic cooking on the myrosinase stability, glucosinolates and hydrolysis products in 18 cabbage accession was investigated. Cabbages were steamed, microwaved, and stir-fried before analysis. Cooking significantly affected myrosinase stability and glucosinolate concentrations within and between cabbage morphotypes. Myrosinase was most stable after stir-frying, with up to 65% residual activity. Steaming and microwaving resulted in over 90% loss of myrosinase activity in some accessions. Stir-frying resulted in the greatest decrease in glucosinolate concentration, resulting in up to 70% loss. Steamed cabbages retained the highest glucosinolates after cooking (up to 97%). The profile and abundance of glucosinolate hydrolysis products detected varied across all cooking methods studied. Cooking reduced the amounts of nitriles and epithionitriles formed compared to raw samples. Steaming led to a significant increase in the concentration of beneficial isothiocyanates present in the cabbage and a significantly lower level of nitriles compared to other samples. Microwaving led to a reduction in the concentrations of both nitriles and isothiocyanates when compared to other cooking methods and raw cabbage. The results obtained help provide information on the optimal cooking methods for cabbage, suggesting that steaming may be the best approach to maximising beneficial isothiocyanate production. Full article
(This article belongs to the Special Issue Advanced Research on Glucosinolates in Food Products)
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26 pages, 13809 KiB  
Article
Influence of Cabbage (Brassica oleracea) Accession and Growing Conditions on Myrosinase Activity, Glucosinolates and Their Hydrolysis Products
by Omobolanle O. Oloyede, Carol Wagstaff and Lisa Methven
Foods 2021, 10(12), 2903; https://doi.org/10.3390/foods10122903 - 23 Nov 2021
Cited by 22 | Viewed by 4479
Abstract
Glucosinolates are secondary plant metabolites present in Brassica vegetables. The endogenous enzyme myrosinase is responsible for the hydrolysis of glucosinolates, yielding a variety of compounds, including health-promoting isothiocyanates. The influence of cabbage accession and growing conditions on myrosinase activity, glucosinolates (GSL) and their [...] Read more.
Glucosinolates are secondary plant metabolites present in Brassica vegetables. The endogenous enzyme myrosinase is responsible for the hydrolysis of glucosinolates, yielding a variety of compounds, including health-promoting isothiocyanates. The influence of cabbage accession and growing conditions on myrosinase activity, glucosinolates (GSL) and their hydrolysis products (GHPs) of 18 gene-bank cabbage accessions was studied. Growing conditions, cabbage morphotype and accession all significantly affected myrosinase activity and concentration of glucosinolates and their hydrolysis products. In general, cabbages grown in the field with lower growth temperatures had significantly higher myrosinase activity than glasshouse samples. Profile and concentration of glucosinolates and their hydrolysis products differed across the accessions studied. Aliphatic glucosinolates accounted for more than 60 % of total glucosinolates in most of the samples assessed. Nitriles and epithionitriles were the most abundant hydrolysis products formed. The results obtained showed that consumption of raw cabbages might reduce the amount of beneficial hydrolysis products available to the consumer, as more nitriles were produced from hydrolysis compared to beneficial isothiocyanates. However, red and white cabbages contained high concentrations of glucoraphanin and its isothiocyanate, sulforaphane. This implies that careful selection of accessions with ample concentrations of certain glucosinolates can improve the health benefits derived from raw cabbage consumption. Full article
(This article belongs to the Special Issue Advanced Research on Glucosinolates in Food Products)
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14 pages, 303 KiB  
Review
Toxicity of Canola-Derived Glucosinolate Degradation Products in Pigs—A Review
by Jung Wook Lee, In Ho Kim and Tofuko Awori Woyengo
Animals 2020, 10(12), 2337; https://doi.org/10.3390/ani10122337 - 9 Dec 2020
Cited by 21 | Viewed by 3340
Abstract
Canola co-products are widely included in swine diets as sources of proteins. However, inclusion of canola co-products in diets for pigs is limited by toxicity of glucosinolate degradation products. Aliphatic and aromatic glucosinolates are two major classes of glucosinolates. Glucosinolate degradation products derived [...] Read more.
Canola co-products are widely included in swine diets as sources of proteins. However, inclusion of canola co-products in diets for pigs is limited by toxicity of glucosinolate degradation products. Aliphatic and aromatic glucosinolates are two major classes of glucosinolates. Glucosinolate degradation products derived from aliphatic glucosinolates (progoitrin) include crambene, epithionitriles, and goitrin, whereas indole-3-acetonitrile, thiocyanate, and indole-3-carbinol are the major aromatic glucosinolates (glucobrassicin)-derived degradation products. At acidic pH (<5.7), progoitrin is degraded by myrosinases to crambene and epithionitriles in the presence of iron, regardless of the presence of epithiospecifier protein (ESP), whereas progoitrin is degraded by myrosinases to goitrin in the absence of ESP, regardless of the presence of iron at neutral pH (6.5). Indole-3-acetonitrile is the major degradation product derived from glucobrassicin in the absence of ESP, regardless of the presence of iron at acidic pH (<4.0), whereas thiocyanate and indole-3-carbinol are the major glucobrassicin-derived degradation products in the absence of ESP, regardless of the presence of iron at neutral pH (7.0). In conclusion, the composition of glucosinolate degradation products is affected by parent glucosinolate composition and hindgut pH. Thus, toxicity of canola co-product-derived glucosinolates can be potentially alleviated by modifying the hindgut pH of pigs. Full article
(This article belongs to the Special Issue Feeds and Feeding Programs in Functional Meat Production)
22 pages, 3298 KiB  
Article
Seasonal Variation of Glucosinolate Hydrolysis Products in Commercial White and Red Cabbages (Brassica oleracea var. capitata)
by Nicole S. Wermter, Sascha Rohn and Franziska S. Hanschen
Foods 2020, 9(11), 1682; https://doi.org/10.3390/foods9111682 - 17 Nov 2020
Cited by 28 | Viewed by 5044
Abstract
Brassica vegetables contain glucosinolates, which are well-known for their potential to form health-promoting isothiocyanates. Among those crucifers, white and red cabbage are commonly consumed vegetables, exhibiting different glucosinolate and hydrolysis profiles thereof. Regarding the health beneficial effects from these vegetables, more information, especially [...] Read more.
Brassica vegetables contain glucosinolates, which are well-known for their potential to form health-promoting isothiocyanates. Among those crucifers, white and red cabbage are commonly consumed vegetables, exhibiting different glucosinolate and hydrolysis profiles thereof. Regarding the health beneficial effects from these vegetables, more information, especially concerning the seasonal variation of glucosinolate profiles and the formation of their bioactive hydrolysis products in commercial cabbages, is needed. In this study, glucosinolates and glucosinolate hydrolysis product profiles in red and white cabbages from three different food retailers were monitored over six different sampling dates across the selling season in autumn. For the first time, it was shown that, while glucosinolate profiles were similar in each cabbage variety, glucosinolate hydrolysis product profiles and hydrolysis behavior varied considerably over the season. The highest total isothiocyanate concentrations were observed in conventional red (1.66 μmol/g FW) and organic white (0.93 μmol/g FW) cabbages purchased at the first sampling date in September. Here, red cabbage was with up to 1.06 μmol/g FW of 4-(methylsulfinyl)butyl isothiocyanate (sulforaphane), an excellent source for this health-promoting isothiocyanate. Cabbages purchased 11 weeks later in autumn released lower levels of isothiocyanates, but mainly nitriles and epithionitriles. The results indicate that commercial cabbages purchased in early autumn could be healthier options than those purchased later in the year. Full article
(This article belongs to the Special Issue Advanced Research on Glucosinolates in Food Products)
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12 pages, 3959 KiB  
Article
Hepatotoxicity of Two Progoitrin-Derived Nitriles in New Zealand White Rabbits
by Mark Grey Collett, Zoe Maree Matthews and Kathleen Henry Parton
Toxins 2020, 12(11), 695; https://doi.org/10.3390/toxins12110695 - 2 Nov 2020
Cited by 5 | Viewed by 2072
Abstract
Cattle occasionally develop brassica-associated liver disease (BALD) and photosensitisation when grazing turnip or swede (Brassica spp.) forage crops. The liver toxin in these brassica varieties has yet to be discovered. Progoitrin is the dominant glucosinolate in incriminated crops. Apart from goitrin, progoitrin [...] Read more.
Cattle occasionally develop brassica-associated liver disease (BALD) and photosensitisation when grazing turnip or swede (Brassica spp.) forage crops. The liver toxin in these brassica varieties has yet to be discovered. Progoitrin is the dominant glucosinolate in incriminated crops. Apart from goitrin, progoitrin hydrolysis yields the nitrile, 1-cyano-2-hydroxy-3-butene (CHB), and the epithionitrile, 1-cyano-2-hydroxy-3,4-epithiobutane (CHEB). The two compounds were custom-synthesised. In a small pilot trial, New Zealand White rabbits were given either CHB or CHEB by gavage. Single doses of 0.75 mmol/kg of CHB or 0.25 mmol/kg of CHEB were subtoxic and elicited subclinical effects. Higher doses were severely hepatotoxic, causing periportal to massive hepatic necrosis associated with markedly elevated serum liver biomarkers often resulting in severe illness or death within 24 h. The possibility that one or both of these hepatotoxic nitriles causes BALD in cattle requires further investigation. Full article
(This article belongs to the Special Issue Plant Toxins Affecting Animal Health and Production)
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32 pages, 4019 KiB  
Review
Glucosinolates: Natural Occurrence, Biosynthesis, Accessibility, Isolation, Structures, and Biological Activities
by V. P. Thinh Nguyen, Jon Stewart, Michel Lopez, Irina Ioannou and Florent Allais
Molecules 2020, 25(19), 4537; https://doi.org/10.3390/molecules25194537 - 3 Oct 2020
Cited by 107 | Viewed by 12311
Abstract
Glucosinolates (GSLs) are secondary plant metabolites abundantly found in plant order Brassicales. GSLs are constituted by an S-β-d-glucopyrano unit anomerically connected to O-sulfated (Z)-thiohydroximate moiety. The side-chain of the O-sulfate thiohydroximate moiety, which is derived [...] Read more.
Glucosinolates (GSLs) are secondary plant metabolites abundantly found in plant order Brassicales. GSLs are constituted by an S-β-d-glucopyrano unit anomerically connected to O-sulfated (Z)-thiohydroximate moiety. The side-chain of the O-sulfate thiohydroximate moiety, which is derived from a different amino acid, contributes to the diversity of natural GSL, with more than 130 structures identified and validated to this day. Both the structural diversity of GSL and their biological implication in plants have been biochemically studied. Although chemical syntheses of GSL have been devised to give access to these secondary metabolites, direct extraction from biomass remains the conventional method to isolate natural GSL. While intact GSLs are biologically inactive, various products, including isothiocyanates, nitriles, epithionitriles, and cyanides obtained through their hydrolysis of GSLs, exhibit many different biological activities, among which several therapeutic benefits have been suggested. This article reviews natural occurrence, accessibility via chemical, synthetic biochemical pathways of GSL, and the current methodology of extraction, purification, and characterization. Structural information, including the most recent classification of GSL, and their stability and storage conditions will also be discussed. The biological perspective will also be explored to demonstrate the importance of these prominent metabolites. Full article
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16 pages, 2959 KiB  
Article
Molecular Modeling of Epithiospecifier and Nitrile-Specifier Proteins of Broccoli and Their Interaction with Aglycones
by Juan Román, Dorian González, Mario Inostroza-Ponta and Andrea Mahn
Molecules 2020, 25(4), 772; https://doi.org/10.3390/molecules25040772 - 11 Feb 2020
Cited by 14 | Viewed by 4539
Abstract
Glucosinolates are secondary plant metabolites of Brassicaceae. They exert their effect after enzymatic hydrolysis to yield aglycones, which become nitriles and epithionitriles through the action of epithiospecifier (ESP) and nitrile-specifier proteins (NSP). The mechanism of action of broccoli ESP and NSP is [...] Read more.
Glucosinolates are secondary plant metabolites of Brassicaceae. They exert their effect after enzymatic hydrolysis to yield aglycones, which become nitriles and epithionitriles through the action of epithiospecifier (ESP) and nitrile-specifier proteins (NSP). The mechanism of action of broccoli ESP and NSP is poorly understood mainly because ESP and NSP structures have not been completely characterized and because aglycones are unstable, thus hindering experimental measurements. The aim of this work was to investigate the interaction of broccoli ESP and NSP with the aglycones derived from broccoli glucosinolates using molecular simulations. The three-dimensional structure of broccoli ESP was built based on its amino-acid sequence, and the NSP structure was constructed based on a consensus amino-acid sequence. The models obtained using Iterative Threading ASSEmbly Refinement (I-TASSER) were refined with the OPLS-AA/L all atom force field of GROMACS 5.0.7 and were validated by Veryfy3D and ERRAT. The structures were selected based on molecular dynamics simulations. Interactions between the proteins and aglycones were simulated with Autodock Vina at different pH. It was concluded that pH determines the stability of the complexes and that the aglycone derived from glucoraphanin has the highest affinity to both ESP and NSP. This agrees with the fact that glucoraphanin is the most abundant glucosinolate in broccoli florets. Full article
(This article belongs to the Special Issue Computational Methods in Drug Design and Food Chemistry)
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10 pages, 1203 KiB  
Communication
Identification of N-Acetyl-S-(3-Cyano-2-(Methylsulfanyl)Propyl-Cysteine as a Major Human Urine Metabolite from the Epithionitrile 1-Cyano-2,3-Epithiopropane, the Main Glucosinolate Hydrolysis Product from Cabbage
by Franziska S. Hanschen, Susanne Baldermann, Adrian Brobrowski, Andrea Maikath, Melanie Wiesner-Reinhold, Sascha Rohn and Monika Schreiner
Nutrients 2019, 11(4), 908; https://doi.org/10.3390/nu11040908 - 23 Apr 2019
Cited by 9 | Viewed by 3595
Abstract
Brassica vegetables such as cabbage or pak choi contain alkenyl glucosinolates which can release epithionitriles and to a lesser degree isothiocyanates upon enzymatic hydrolysis. Here, for the first time, the metabolism of an epithionitrile was investigated in humans, namely 1-cyano-2,3-epithiopropane (CETP). After consumption [...] Read more.
Brassica vegetables such as cabbage or pak choi contain alkenyl glucosinolates which can release epithionitriles and to a lesser degree isothiocyanates upon enzymatic hydrolysis. Here, for the first time, the metabolism of an epithionitrile was investigated in humans, namely 1-cyano-2,3-epithiopropane (CETP). After consumption of Brassica oleracea var. capitata f. alba and Brassica carinata sprouts, the main urinary metabolite of CETP was identified as N-acetyl-S-(3-cyano-2-(methylsulfanyl)propyl-cysteine using an UHPLC-ESI-QToF-MS approach and synthesis of the metabolite. This urinary epithionitrile metabolite is an S-methylated mercapturic acid. No other metabolites were detected. Then, in a preliminary pilot experiment the excretion kinetics of CETP were investigated in three volunteers. After consumption of a B. carinata sprout preparation containing 50.8 µmol of CETP, urinary N-acetyl-S-(3-cyano-2-(methylsulfanyl)propyl-cysteine concentrations were the highest three hours after consumption, ranging from 23.9 to 37.2 µM, and declined thereafter. Thus, epithionitriles are bioavailable compounds that are metabolized similarly to isothiocyanates by the mercapturic acid pathway. In the future, more epithionitrile metabolites should be identified and the pharmacokinetics of these important class of dietary compounds should be assessed in more detail. Full article
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