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GlucosinolatesHydrolysisThioglucosidesBrassicaBrassicaceaeIsothiocyanatesArabidopsisOximesHerbivoryMustard PlantArabidopsis ProteinsSinapisPlant LeavesAzorhizobium caulinodansGlycoside HydrolasesThiocyanatesGene Expression Regulation, PlantLepidiumImidoestersManihotOxylipinsPhytochemicalsAnticarcinogenic AgentsPhloemAphidsPlants, Genetically ModifiedOvipositionBrassica rapaSelenium CompoundsCyclopentanesButterfliesCookingChromatography, High Pressure LiquidCytochrome P-450 Enzyme SystemDisease ResistanceAlternariaIndolesLepidoptera
IsothiocyanatesCompoundsAliphatic glucosinolatesCleaves off the glucose groupCruciferous vegetablesNitrilesArabidopsisIsothiocyanateEnzymeIndolic glucosinolatesBiosynthesisSulforaphaneAllylCow's milkMustardBrassicaceaePungentCabbageSinigrinProductsThiocyanate-formingBroccoliGeneralistPhytochemistryDefenseITCsPotassiumSecondaryAminoDegradationOccurrenceHydrolyticEpithionitrilesCentral carbon atomHorseradishProteinsEcologicalSupplementsPlantGroupNaturallyPlantsActivity
Isothiocyanates14
  • Scientists at the Max Planck Institute for Chemical Ecology in Jena have long been studying the glucosinolates and isothiocyanates that constitute the special defense mechanism of cabbage family plants, which include rapeseed, radishes and mustard. (mpg.de)
  • Glutathione conjugation cannot detoxify isothiocyanates nearly as effectively as hydrolysis can. (mpg.de)
  • Hydrolysis products of glucosinolates, isothiocyanates, have been associated with health benefits and contribute to the flavor of Brassica. (nih.gov)
  • Upon tissue damage, e.g. by herbivory, glucosinolates and myrosinases get mixed and glucosinolates are broken down to an array of biologically active compounds of which isothiocyanates are toxic to a wide range of organisms. (biomedcentral.com)
  • Besides uses as an ingredient for food and feed, the contents of bioactive phytochemicals such as terpenoids, alkaloids, glucosinolates, tocopherols, polyprenols, isothiocyanates, carotenoids and phenolics, have allowed to envisage potential applications of C. spinosa as a health promoter plant. (scialert.net)
  • Current research suggests that glucosinolates (and isothiocyanates) act via several mechanisms, ultimately exhibiting anti-inflammatory, antioxidant, and chemo-protective effects. (frontiersin.org)
  • acephala) accessions exhibited particular similarities in the composition of LOX volatiles, while the LOX volatilome fraction of B. incana and B. mollis partially coincided with that of another wild species, Diplotaxis tenuifolia L. Regarding volatiles formed in the glucosinolate (GSL) pathway, Savoy cabbage and wild species B. incana, B. mollis, and D. tenuifolia showed more intense emission of isothiocyanates than cabbage and kale. (irb.hr)
  • Upon hydrolysis, GLSs form health-promoting isothiocyanates (ITCs), but also nitriles and epithionitriles. (bvsalud.org)
  • Boiling reduces the content of its distinctive sulfur-containing glucosinolate molecules, isothiocyanates, and sulforaphane, whereas steaming, microwaving, or stir-frying better preserves these components. (growzo.in)
  • Glucosinolates and their hydrolysis products, particularly isothiocyanates and other sulfur-containing chemicals, are responsible for the alleged bitterness of cruciferous vegetables like broccoli. (growzo.in)
  • cruciferous vegetables are rich unique sources of glucosinolates, whose hydrolytic products, primarily isothiocyanates (ITCs) and indoles, may have cancer chemopreventive properties. (24mantra.com)
  • Chopping and chewing of these cruciferous vegetables lead to the breakdown of glucosinolates which give rise to indoles and isothiocyanates which may help in the prevention of cancer. (24mantra.com)
  • Isothiocyanates (ITCs) are classified as a separate group of volatile sulfur compounds naturally occurring by enzymatic hydrolysis of glucosinolates in the presence of the myrosinase enzyme. (ktf-split.hr)
  • Glucosinolates, isothiocyanates and indoles Chapter 3. (hollownine.com)
Compounds10
  • Glucosinolates constitute a natural class of organic compounds that contain sulfur and nitrogen and are derived from glucose and an amino acid. (wikipedia.org)
  • different glucosinolates have different side groups, and it is variation in the side group that is responsible for the variation in the biological activities of these plant compounds. (wikipedia.org)
  • MSM contains glucosinolates that undergo hydrolysis to compounds with pesticidal properties. (usda.gov)
  • Horseradish contains cancer-fighting compounds known as glucosinolates. (foodrevolution.org)
  • Glycosides are a major group of plant secondary compounds characterized by one or more sugars conjugated to a lipophilic, possibly toxic aglycone, which is released upon hydrolysis. (silverchair.com)
  • Glucosinolates are sulphur containing compounds and they are responsible for the unique sharp taste and pungent aroma characteristic of these cruciferous vegetables. (24mantra.com)
  • When these vegetables are cut, crushed or chewed the actions of the enzyme myrosinase (released from the cells) hydrolyses these glucosinolates into other compounds. (happyleefitness.com)
  • Most of our glucosinolates and related compounds are certified as primary reference standards. (phytolab.com)
  • When the raw vegetables are chopped or chewed, an enzyme called myrosinase that is also present in these plants breaks the glucosinolates apart (through hydrolysis) into a variety of biologically active compounds, many of which are potent antioxidants and are known to prevent cancer. (hollownine.com)
  • Cruciferous vegetables are particularly rich in a group of sulfur-containing compounds called glucosinolates. (hollownine.com)
Aliphatic glucosinolates3
  • They are biosynthesized from amino acids: so-called aliphatic glucosinolates derived from mainly methionine, but also alanine, leucine, isoleucine, or valine. (wikipedia.org)
  • Examples of structures of aliphatic glucosinolates ( 1 , 4-methylthiobutylglucosinolate), aromatic (i.e. (biomedcentral.com)
  • Cytochrome P450 CYP79F1 from Arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates. (mpg.de)
Cleaves off the glucose group2
  • The plants contain the enzyme myrosinase, which, in the presence of water, cleaves off the glucose group from a glucosinolate. (wikipedia.org)
  • Upon mixing the sinigrin and myrosinase formulations together with water, a hydrolysis reaction occurs in which the myrosinase cleaves off the glucose group from the glucosinolate, and the remaining molecule quickly converts to allyl isothiocyanate (AITC). (mustgrow.ca)
Cruciferous vegetables8
  • A possible protective component, glucosinolates, which are phytochemicals found almost exclusively in cruciferous vegetables, have been identified from preclinical and clinical studies. (frontiersin.org)
  • This review summarizes the current knowledge surrounding cruciferous vegetables and their glucosinolates in relation to the specified health conditions. (frontiersin.org)
  • Although these vegetables contain a range of nutrients known to have beneficial health properties, studies have focused on the health effects of glucosinolates that are found almost exclusively in cruciferous vegetables. (frontiersin.org)
  • Apart from these the cruciferous vegetables are rich sources of glucosinolates. (24mantra.com)
  • In a study carried out it was observed that these cruciferous vegetables contain non-nutritive components such as glucosinolate hydrolysis products, sulforaphane, and indole-3-carbinol. (24mantra.com)
  • The concentration of glucosinolate in cruciferous vegetables can vary depending on the species, cultivar and environmental conditions. (24mantra.com)
  • Many of the health benefits derived from eating cruciferous vegetables (cabbage, brussels sprouts, broccoli etc.), especially those which are thought to be beneficial for breast and prostate health, are thought to be derived from the group of secondary metabolites known as glucosinolates. (happyleefitness.com)
  • Cruciferous vegetables belong to the large Brassicaceae or mustard family and contain sulfur-containing glucosinolates that gives them a distinctive aroma and taste. (hollownine.com)
Nitriles3
  • Formation of simple nitriles upon glucosinolate hydrolysis affects direct and indirect defense against the specialist herbivore, pieris rapae. (mpg.de)
  • The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory. (mpg.de)
  • AthNIT1-3 have a strong substrate preference for phenylpropionitrile (PPN) and other nitriles which may originate from the breakdown of glucosinolates. (umbc.edu)
Arabidopsis10
  • Full details of the sequence of reactions that converts individual amino acids into the corresponding glucosinolate have been studied in the cress Arabidopsis thaliana. (wikipedia.org)
  • ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis. (mpg.de)
  • Altered glucosinolate hydrolysis in genetically engineered Arabidopsis thaliana and its influence on the larval development of Spodoptera littoralis. (mpg.de)
  • Glucosinolate research in the Arabidopsis era. (mpg.de)
  • A novel 2-oxoacid-dependent dioxygenase involved in the formation of the goiterogenic 2-hydroxybut-3-enyl glucosinolate and generalist insect resistance in Arabidopsis thaliana. (mpg.de)
  • Geographic and evolutionary diversification of glucosinolates among near relatives of Arabidopsis thaliana (Brassicaceae). (mpg.de)
  • Comparative analysis of quantitative trait loci controlling glucosinolates, myrosinase and insect resistance in Arabidopsis thaliana. (mpg.de)
  • Benzoic acid glucosinolate esters and other glucosinolates from Arabidopsis thaliana. (mpg.de)
  • Genetic control of natural variation in Arabidopsis glucosinolate accumulation. (mpg.de)
  • Gene duplication in the diversification of secondary metabolism: Tandem 2-oxoglutarate-dependent dioxygenases control glucosinolate biosynthesis in Arabidopsis. (mpg.de)
Isothiocyanate7
  • The essence of glucosinolate chemistry is their ability to convert into an isothiocyanate (a "mustard oil") upon hydrolysis of the thioglucoside bond by the enzyme myrosinase. (wikipedia.org)
  • Specifier proteins occur in some, but not all glucosinolate-containing plants and promote the formation of biologically active non-isothiocyanate products upon myrosinase-catalyzed glucosinolate breakdown. (biomedcentral.com)
  • B . Using allylglucosinolate ( 4 , aliphatic side chain with terminal double bond) as an example, the hydrolysis by myrosinase ( a ) is shown that leads to the formation of an isothiocyanate upon spontaneous rearrangement of the aglycone ( b ) or to the formation of alternative products ( c - e ). (biomedcentral.com)
  • Concentrations of various glucosinolate hydrolysis products differed according to USDA grade, with U.S. Fancy having greater allyl isothiocyanate (AITC) and U.S. No. 1 having greater 1-cyano 2,3-epithiopropane (CETP). (foodrevolution.org)
  • Deodorized yellow mustard powder has antimicrobial properties from glucosinolate (sinalbin) hydrolysis catalyzed by the endogenous enzyme myrosinase, generating antimicrobial isothiocyanate (PHBIT). (umanitoba.ca)
  • One trial included the inoculation of Staphylococcus (S.) carnosus, a meat starter culture with myrosinase-like activity, onto the hams (after salt equilibration) to accelerate formation of antimicrobial isothiocyanate from mustard glucosinolate and help control the pathogen. (umanitoba.ca)
  • Moringin is an isothiocyanate obtained from myrosinase-mediated hydrolysis of the glucosinolate precursor glucoMoringin present in Moringa oleifera seeds. (targetmol.jp)
Enzyme1
  • However, boiling broccoli causes the myrosinase enzyme needed for hydrolysis to denature. (nih.gov)
Indolic glucosinolates2
Biosynthesis4
  • The role of cytochromes P450 in biosynthesis and evolution of glucosinolates. (mpg.de)
  • Determination of the absolute configuration of the glucosinolate methyl sulfoxide group reveals a stereospecific biosynthesis of the side chain. (mpg.de)
  • Furthermore, a substance-specific side chain (its structure depending on the amino acid involved in the initial phase of the glucosinolate biosynthesis) is bound to the central carbon atom. (phytolab.com)
  • The biosynthesis of glucosinolates with a phenyl or benzyl ring in the core structure starts from either phenylalanine or tyrosine (e.g. glucobarbarin , glucolimnanthin , glucomoringin , gluconasturtiin , glucotropaeolin and sinalbin ), while indolyl-containing side chains as in glucobrassicin originate from the amino acid tryptophane. (phytolab.com)
Sulforaphane1
  • Most other supplements contain the precursor, sulforaphane glucosinolate or glucoraphanin. (advancedliving.com)
Allyl1
  • For example, allylglucosinolate and allyl glucosinolate refer to the same compound: both versions are found in the literature. (wikipedia.org)
Cow's milk1
  • 12 During the process of ripening, the beneficial bacteria in Parmigiano-Reggiano promote an extensive hydrolysis of cow's milk proteins resulting in peptides that exhibit positive immunoregulatory activities. (donnieyance.com)
Mustard3
  • Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. (wikipedia.org)
  • The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damaged. (wikipedia.org)
  • In order to ensure hydrolysis, broccoli must either be mildly cooked or active sources of myrosinase, such as mustard seed powder, can be added postcooking. (nih.gov)
Brassicaceae3
  • El objetivo de este estudio fue evaluar el efecto de diferentes tipos de semilla molida de Brassicaceae y de sus dosis de aplicación en la emergencia de Avena fatua , Lolium multiflorum, Lactuca serriola y Amaranthus retroflexus , las cuales son algunas de las principales malezas en los sistemas de producción de hortalizas. (cambridge.org)
  • Several species of the Brassicaceae, well known for their glucosinolate-myrosinase defence system, are invasive species. (uni-bielefeld.de)
  • Like all Brassicaceae, indeed, it also contains glucosinolates which give the plant its typical pungent taste. (alleanzaverde.com)
Pungent1
  • Besides being responsible for the pungent and bitter taste of these plants, the glucosinolates and their hydrolysis products also protect plants against herbivores and have been shown to have antimicrobial, antiviral, antifungal and anticarcinogenic properties. (phytolab.com)
Cabbage3
  • Glucosinolates occur in various edible plants such as cabbage (white cabbage, Chinese cabbage, broccoli), Brussels sprouts, watercress, horseradish, capers, and radishes where the breakdown products often contribute a significant part of the distinctive taste. (wikipedia.org)
  • Changes in glucosinolate concentrations, myrosinase activity and production of hydrolysis products of glucosinolates in cabbage (Brassica oleracea var. (hutton.ac.uk)
  • Red cabbage is a popular vegetable in Central Europe and a rich source of glucosinolates (GLSs). (bvsalud.org)
Sinigrin1
  • We compared small intestinal homogenate hydrolysis activity of three rodent and two avian species against four substrates: amygdalin and sinigrin, two plant-derived glucosides, the sugar lactose, whose hydrolysis models some activity against flavonoid and isoflavonoid glucosides, and the disaccharide sugar maltose (from starch), used as a comparator. (silverchair.com)
Products3
  • In the new study, Kushad and his team looked for the products of glucosinolate hydrolysis, which activate enzymes involved in detoxification of cancer-causing molecules. (foodrevolution.org)
  • Specific emphasis is laid on the role of glucosinolates and their hydrolysis products in the invasion potential. (uni-bielefeld.de)
  • The authors describe the anticarcinogenic bioactivities of glucosinolate hydrolysis products, the mineral selenium derived from crucifers, and the mechanisms involved in the protective properties against cancer. (24mantra.com)
Thiocyanate-forming1
Broccoli2
Generalist1
  • Glucosinolate hydrolysis and its impact on generalist and specialist insect herbivores. (mpg.de)
Phytochemistry1
Defense2
  • The researchers were able to show experimentally that the defense based on glucosinolates is actually effective against fungal attacks. (mpg.de)
  • The glucosinolate-myrosinase system is an activated chemical defense system found in plants of the Brassicales order. (biomedcentral.com)
ITCs2
  • Recently, ITCs were shown to undergo further hydrolysis, yielding amines. (bvsalud.org)
  • 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. (bvsalud.org)
Potassium1
  • As the sulfate group is negatively charged, glucosinolates are most often isolated in the form of their potassium salts. (phytolab.com)
Secondary1
  • Glucosinolates occur as secondary metabolites of almost all plants of the order Brassicales. (wikipedia.org)
Amino2
  • Most glucosinolates are actually derived from chain-elongated homologues of these amino acids, e.g. glucoraphanin is derived from dihomomethionine, which is methionine chain-elongated twice. (wikipedia.org)
  • Glucosinolates are amino acid-derived thioglucosides with a sulfated aldoxime moiety and variable side chains (Figure 1 A) that are present in the Brassicales [ 11 - 13 ]. (biomedcentral.com)
Degradation1
  • Our portfolio currently includes a total of 25 glucosinolates and one glucosinolate-derived goitrogenic degradation product. (phytolab.com)
Occurrence1
  • Outside of the Brassicales, the genera Drypetes and Putranjiva in the family Putranjivaceae, are the only other known occurrence of glucosinolates. (wikipedia.org)
Hydrolytic1
  • Glucosinolates are stored separately from their hydrolytic enzymes, the myrosinases, in plant tissues. (biomedcentral.com)
Epithionitriles1
Central carbon atom1
  • Every glucosinolate contains a central carbon atom, which is bound to the sulfur atom of the thioglucose group, and via a nitrogen atom to a sulfate group (making a sulfated aldoxime). (wikipedia.org)
Horseradish2
Proteins1
  • Comparative biochemical characterization of nitrile-forming proteins from plants and insects that alter myrosinase-catalysed hydrolysis of glucosinolates. (mpg.de)
Ecological1
  • The glucosinolate-myrosinase system in an ecological and evolutionary context. (mpg.de)
Supplements1
  • Although there is evidence that consumption of a high glucosinolate diet is linked with reduced incidence of chronic diseases, future large-scale placebo-controlled human trials including standardized glucosinolate supplements are needed. (frontiersin.org)
Plant1
  • The glucosinolate-myrosinase system represents one of the best studied plant chemical defenses. (biomedcentral.com)
Group3
  • The semisystematic naming of glucosinolates consists of the chemical name of the group "R" in the diagram followed by "glucosinolate", with or without a space. (wikipedia.org)
  • The group found that the higher-grade U.S. Fancy accessions had significantly more glucosinolates than U.S. No. 1. (foodrevolution.org)
  • All glucosinolates are composed of a central carbon that is bound via a sulfur atom to a glucose, and via a nitrogen atom to a sulfate group. (phytolab.com)
Naturally1
Plants1
Activity2
  • The product of PPN hydrolysis, phenylacetic acid has auxin activity. (umbc.edu)
  • Thus, application of moderate pressures (200-400 MPa) can potentially be used to retain myrosinase activity needed for subsequent glucosinolate hydrolysis. (reading.ac.uk)