Show legend Show as text

Structure type: monomer
Trivial name: sinigrin
Compound class: glycoside, glucosinolate

• Article ID: 12036
  Bernays EA, Oppenheim S, Chapman RF, Kwon H, Gould F "Taste sensitivity of insect herbivores to deterrents is greater in specialists than in generalists: a behavioral test of the hypothesis with two closely related caterpillars" - Journal of Chemical Ecology 26(2) (2000) 547–563
  

  Sensitivity of caterpillars of Heliothis virescens, a generalist, and H. subflexa, a specialist, to eight different plant secondary compounds was examined behaviorally. The compounds were nicotine hydrogen tartrate, hordenine, caffeine, sinigrin, linamarin, arbutin, chlorogenic acid, and salicin. All compounds deterred feeding, at least at the higher concentrations, but the generalist was less affected than the specialist. Thus the hypothesis that specialists have greater sensitivity to deterrents than generalists was supported. In most cases deterrence occurred on first encounter, indicating that the response was sensory; in some cases short-term postingestive effects also appeared to play a role. The larger quantities of deterrent-containing food ingested by H. virescens sometimes resulted in measurable postingestive effects during the second control test. This did not occur in H. subflexa, which more commonly rejected the deterrent-containing food on first contact. The contrast between the species is discussed in relation to tradeoffs involved in different diet breadths.

  Heliothis virescens, Heliothis subflexa, caterpillar, diet breadth, deterrent compound, feeding behavior, postingestive toxicity, plant secondary metabolite

  Publication DOI: 10.1023/A:1005430010314
  Journal NLM ID: 7505563
  Publisher: Springer
  Institutions: Entomology Department, University of Arizona, Tucson, USA, Entomology Department, North Carolina State University, Raleigh, USA, Division of Neurobiology, University of Arizona, Tucson, USA
  Methods: biological assays
  
   
  
  (plant)
  CSDB ID 64933 (all data & tools)
• Article ID: 12356
  Leoni O, Iori R, Palmieri S "Hydrolysis of glucosinolates using nylon-immobilized myrosinase to produce pure bioactive molecules" - Biotechnology and Bioengineering 68(6) (2000) 660-664
  

  Bioactive compounds were produced from natural glucosinolates, secondary plant metabolites, using myrosinase (thioglucoside glucohydrolase EC 3.2.3.1) isolated from ripe seeds of Sinapis alba. The enzyme was immobilized on granular nylon 6.6 with the crosslinking technique. Immobilized myrosinase displayed extraordinary operational and storage stability. Using a small thermostatted continuous packed-bed bioreactor, the enzyme activity was unchanged after 15 days of continuous use at 37°C and after >1 year of storage at room temperature. The bioreactor was particularly efficient in producing pure isothiocyanates, but it was less efficient for pure nitrile production.

  immobilization, bioreactor, myrosinase, glucosinolates, isothiocyanates, nitriles

  NCBI PubMed ID: 10799991
  Publication DOI: 10.1002/(sici)1097-0290(20000620)68:6<660::aid-bit9>3.0.co;2-l
  Journal NLM ID: 7502021
  Publisher: New York: Wiley-VCH
  Correspondence: sandro.palmieri@iol.it
  Institutions: Istituto Sperimentale per le Colture Industriali of Italian Ministry of Agricultural and Forestry Politics, Bologna, Italy
  
   
  
  Brassica juncea
  CSDB ID 66273 (all data & tools)
• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67431 (all data & tools)
• Article ID: 12760
  Tolrà RP, Alonso R, Poschenrieder C, Barceló D, Barceló J "Determination of glucosinolates in rapeseed and Thlaspi caerulescens plants by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry" - Journal of Chromatography A 889(1-2) (2000) 75-81
  

  Liquid chromatography-atmospheric pressure chemical ionization mass spectrometry was used to identify glucosinolates in plant extracts. Optimization of the analytical conditions and the determination of the method detection limit was performed using commercial 2-propenylglucosinolate (sinigrin). Optimal values for the following parameters were determined: nebulization pressure, gas temperature, flux of drying gas, capillar voltage, corona current and fragmentor conditions. The method detection limit for sinigrin was 2.85 ng. For validation of the method the glucosinolates in reference material (rapeseed) from the Community Bureau of Reference Materials (BCR) were analyzed. The method was applied for the determination of glucosinolates in Thlaspi caerulescens plants.

  Thlaspi caerulescence; plant materials; glucosinolates; sulfur compounds; carbohydrates

  NCBI PubMed ID: 10985538
  Publication DOI: 10.1016/s0021-9673(00)00373-3
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Correspondence: juan.barcelo@uab.es
  Institutions: Laboratorio de Fisiología Vegetal, Facultad de Ciencias, Universidad Autónoma de Barcelona, Bellaterra, Spain, Instituto Investigaciones Químicas y Ambientales, CSIC Barcelona, Barcelona, Spain
  Methods: extraction, LC, APCI-MS
  
   
  
  Thlaspi caerulescens, Brassica napus
  CSDB ID 68198 (all data & tools)
• Article ID: 12766
  Trigo JR "The chemistry of antipredator defense by secondary compounds in neotropical Lepidoptera: facts, perspectives and caveats" - Journal of the Brazilian Chemical Society 11(6) (2000) 551-561
  

  Chemical defense against predation in butterflies and moths has been studied since nineteenth century. A classical example is that of the larvae of the monarch butterfly Danaus plexippus, which feed on leaves of Asclepias curassavica (Asclepiadaceae), sequestering cardenolides. The adults are protected against predation by birds. Several other substances may be involved in chemical defense, such as iridoid glycosides, cyanogenic glycosides, glucosinolates, pyrrolizidine and tropane alkaloids, aristolochic acids, glycosidase inhibitors and pyrazines. The acquisition of these substances by lepidopterans can be due to sequestration from larval or adult host plants or de novo biosynthesis. Many Lepidoptera are known to be unpalatable, including the butterflies Troidini (Papilionidae), Pierinae (Pieridae), Eurytelinae, Melitaeinae, Danainae, Ithomiinae, Heliconiinae and Acraeinae (Nymphalidae), and Arctiidae moths, but knowledge of the chemical substances responsible for property is often scarce. This review discusses mainly three topics: field and laboratory observations on rejection of butterflies and moths by predators, correlation between unpalatability and chemicals found in these insects, and bioassays that test the activity of these chemicals against predators. Perspectives and future directions are suggested for this subject.

  pyrrolizidine alkaloids; tropane alkaloids; aristolochic acids; cardenolides; cyanogenic glycosides; glucosinolates

  Publication DOI: 10.1590/S0103-50532000000600002
  Journal NLM ID: 101511356
  Publisher: Sociedade Brasileira de Quimica
  Correspondence: trigo@unicamp.br
  Institutions: Departamento de Zoologia, Instituto de Biologia, Universidade Estadual de Campinas, Campinas, Brazil
  
   
  
  (plant)
  CSDB ID 68234 (all data & tools)
• Article ID: 12792
  Vierheilig H, Bennett R, Kiddle G, Kaldorf M, Ludwig-Müller J "Differences in glucosinolate patterns and arbuscular mycorrhizal status of glucosinolate-containing plant species" - New Phytologist 146(2) (2000) 343-352
  

  Under defined laboratory conditions it was shown that two glucosinolate-containing plant species, Tropaeolum majus and Carica papaya, were colonized by arbuscular mycorrhizal (AM) fungi, whereas it was not possible to detect AM fungal structures in other glucosinolate-containing plants (including several Brassicaceae). Benzylglucosinolate was present in all of the T. majus cultivars and in C. papaya it was the major glucosinolate. 2-Phenylethylglucosinolate was found in most of the non-host plants tested. Its absence in the AM host plants indicates a possible role for the isothiocyanate produced from its myrosinase-catalysed hydrolysis as a general AM inhibitory factor in non-host plants. The results suggest that some of the indole glucosinolates might also be involved in preventing AM formation in some of the species. In all plants tested, both AM hosts and non-hosts, the glucosinolate pattern was altered after inoculation with one of three different AM fungi (Glomus mosseae, Glomus intraradices and Gigaspora rosea), indicating signals between AM fungi and plants even before root colonization. The glucosinolate induction was not specifically dependent on the AM fungus. A time-course study in T. majus showed that glucosinolate induction was present during all stages of mycorrhizal colonization.

  Brassicaceae, glucosinolates, arbuscular mycorrhiza, Glomus, Tropaeolum majus

  NCBI PubMed ID: 33862976
  Publication DOI: 10.1046/j.1469-8137.2000.00642.x
  Journal NLM ID: 9882884
  Publisher: Blackwell Publishing
  Correspondence: jutta.ludwig-mueller@mailbox.tu-dresden.de
  Institutions: Institut für Phytopathologie, Christian-Albrechts-Universität, Kiel, Germany, Cellular Metabolism and Enzymology Group, Institute of Food Research, Norwich Research Park, Colney, UK, Biochemistry and Physiology Department, IACR–Rothamsted, Harpenden, UK, Institut für Ökologie, Lehrbereich Umweltwissenschaften, Friedrich-Schiller-Universität, Jena, Germany, Institut für Botanik, Technische Universität Dresden, Dresden, Germany
  Methods: HPLC, extraction
  
   
  
  Tropaeolum majus cv. SKK, Tropaeolum majus cv. Nanum, Tropaeolum majus cv. BGF, Carica papaya, Lepidium sativum, Sinapis alba, Barbarea praecox, Barbarea vulgaris, Nasturtium officinale, Brassica napus, Brassica nigra, Reseda alba, Reseda lutea, Reseda luteola
  CSDB ID 68371 (all data & tools)
• Article ID: 12799
  Vogt T "Glycosyltransferases involved in plant secondary metabolism" - Book: Evolution of Metabolic Pathways (2000) 317-347
  

  glycosyltransferases, glycosides, plant secondary metabolism

  WWW link: https://books.google.ru/books/about/Evolution_of_Metabolic_Pathways.html?id=tSwKpXKVmOkC&redir_esc=y
  Publisher: Elsevier
  Editors: Romeo JT, Ibrahim R, Varin L, De Luca V
  Institutions: Leibniz-Institut for Ptlanzenbiochemie, Halle/Saale, Germany
  
   
  
  (plant)
  CSDB ID 68401 (all data & tools)
• Article ID: 12800
  Vogt T, Jones P "Glycosyltransferases in plant natural product synthesis: characterization of a supergene family" - Trends in Plant Science 5(9) (2000) 380-386
  

  Glycosyltransferases of plant secondary metabolism transfer nucleotide-diphosphate-activated sugars to low molecular weight substrates. Until recently, glycosyltransferases were thought to have only limited influence on the basic physiology of the plant. This view has changed. Glycosyltransferases might in fact have an important role in plant defense and stress tolerance. Recent results obtained with several recombinant enzymes indicate that many glycosyltransferases are regioselective or regiospecific rather than highly substrate specific. This might indicate how plants evolve novel secondary products, placing enzymes with broad substrate specificities downstream of the conserved, early, pivotal enzymes of plant secondary metabolism.

  glycosyltransferases, glycosides, plant secondary metabolism

  NCBI PubMed ID: 10973093
  Publication DOI: 10.1016/s1360-1385(00)01720-9
  Journal NLM ID: 9890299
  Publisher: Elsevier
  Correspondence: Vogt T ; Jones P
  Institutions: Department of Plant Secondary Metabolism, Leibniz Institute for Plant Biochemistry, Halle/Saale, Germany, Department of Horticulture, Viticulture and Oenology, University of Adelaide, Glen Osmond, Australia, Plant Biochemistry Laboratory, Department of Plant Biology, and the Center for Molecular Plant Physiology (Place), The Royal Veterinary and Agricultural University, Frederiksberg, Denmark
  
   
  
  (plant)
  CSDB ID 68411 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: sinalbin
Compound class: glycoside, glucosinolate

• Article ID: 12356
  Leoni O, Iori R, Palmieri S "Hydrolysis of glucosinolates using nylon-immobilized myrosinase to produce pure bioactive molecules" - Biotechnology and Bioengineering 68(6) (2000) 660-664
  

  Bioactive compounds were produced from natural glucosinolates, secondary plant metabolites, using myrosinase (thioglucoside glucohydrolase EC 3.2.3.1) isolated from ripe seeds of Sinapis alba. The enzyme was immobilized on granular nylon 6.6 with the crosslinking technique. Immobilized myrosinase displayed extraordinary operational and storage stability. Using a small thermostatted continuous packed-bed bioreactor, the enzyme activity was unchanged after 15 days of continuous use at 37°C and after >1 year of storage at room temperature. The bioreactor was particularly efficient in producing pure isothiocyanates, but it was less efficient for pure nitrile production.

  immobilization, bioreactor, myrosinase, glucosinolates, isothiocyanates, nitriles

  NCBI PubMed ID: 10799991
  Publication DOI: 10.1002/(sici)1097-0290(20000620)68:6<660::aid-bit9>3.0.co;2-l
  Journal NLM ID: 7502021
  Publisher: New York: Wiley-VCH
  Correspondence: sandro.palmieri@iol.it
  Institutions: Istituto Sperimentale per le Colture Industriali of Italian Ministry of Agricultural and Forestry Politics, Bologna, Italy
  
   
  
  Sinapis alba
  CSDB ID 66277 (all data & tools)
• Article ID: 12490
  Mithen RF, Dekker M, Verkerk R, Rabot S, Johnson IT "The nutritional significance, biosynthesis and bioavailability of glucosinolates in human foods" - Journal of the Science of Food and Agriculture 80(7) (2000) 967-984
  

  The glucosinolates are a large group of sulphur-containing compounds which occur in all the economically important varieties of Brassica vegetable. Their common structure comprises a β-D-thioglucose group, a sulphonated oxime moiety and a variable side-chain derived from methionine, tryptophan or phenylalanine. When the plant tissue is damaged the glucosinolates are hydrolysed by the endogenous enzyme ‘myrosinase’ (thioglucoside glycohydrolase EC 3:2:3:1), to release a range of breakdown products including the bitter, biologically active isothiocyanates. Although these compounds exert antinutritional effects in animals there is also substantial evidence that they are the principal source of anticarcinogenic activity in Brassica vegetables, and this provides a strong motive for the manipulation of glucosinolate levels in vegetables for human consumption. This review provides an overview of the evidence for a beneficial role for glucosinolates in human health, and describes the current state of knowledge regarding the genetics and biosynthesis of glucosinolates, their chemical analysis, their behaviour during cooking and processing, and their bioavailability to humans. As the genetic basis of glucosinolate biosynthesis becomes more apparent, and tools for marker-assisted plant breeding become more available, the selective breeding of horticultural brassicas with different levels and types of glucosinolates, whether by conventional means or genetic manipulation, is becoming a practical possibility. However before this strategy becomes commercially viable, the health benefits of glucosinolates for human beings must be unequivocally established.

  plant breeding, brassicas; glucosinolates; processing; health; nutrition

  Publication DOI: 10.1002/(SICI)1097-0010(20000515)80:7<967::AID-JSFA597>3.0.CO;2-V
  Journal NLM ID: 0376334
  Publisher: Chichester, West Sussex: John Wiley And Sons Ltd
  Institutions: Institute of Food Research, Norwich Research Park, Colney, UK, John Innes Centre, Norwich Research Park, Colney, UK, Integrated Food Technology, Department of Food Technology and Nutritional Sciences, Wageningen University, Wageningen, The Netherlands, INRA, Unite D’Ecologie et de Physiologie Du Systeme Digestif, Jouy-en-Josas, France
  
   
  
  (plant)
  CSDB ID 66904 (all data & tools)
• Article ID: 12521
  Nastruzzi C, Cortesi R, Esposito E, Menegatti E, Leoni O, Iori R, Palmieri S "In vitro antiproliferative activity of isothiocyanates and nitriles generated by myrosinase-mediated hydrolysis of glucosinolates from seeds of cruciferous vegetables" - Journal of Agricultural and Food Chemistry 48(8) (2000) 3572-3575
  

  A comparison of the effect of isothiocyanates and nitriles derived from some glucosinolates, namely, epi-progoitrin, sinalbin, glucotropaeolin, glucocheirolin, and glucoraphenin, on human erythroleukemic in vitro cultured cells was studied. Many studies have in fact evidenced that a consumption of vegetable containing glucosinolates could reduce the development of colorectal cancer. In the experimental conditions used, the production of isothiocyanates and nitriles from glucosinolates is almost quantitative as confirmed by HPLC or GC-MS analysis. The obtained results demonstrated that in general nitriles are considerably less potent than the corresponding isothiocyanates in inhibiting cancer cell growth. Particularly, the isothiocyanates inhibitory activity on K562 cells growth is higher in the case of products derived from epi-progoitrin, glucotropaeolin, glucoraphenin, and glucocheirolin; while for nitriles the higher activity in inhibiting K562 cells growth is showed by sinalbin-derived product. Considering the antiproliferative activity found for isothiocyanates and nitriles, further studies will be aimed to the possible application of glucosinolate-derived products as chemopreventive cancer agents for the reduction of colorectal cancer.

  enzymes and enzyme reactions; antitumor compounds; antiproliferative agents

  NCBI PubMed ID: 10956152
  Publication DOI: 10.1021/jf000191p
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: Nastruzzi C
  Institutions: Dipartimento di Scienze Farmaceutiche, Università di Ferrara, Ferrara, Italy, Istituto di Chimica e Tecnologia del Farmaco, Università di Perugia, Perugia, Italy, Istituto Sperimentale per le Colture Industriali MiRAAF, Bologna, Italy
  Methods: biological assays
  
   
  
  Cruciferae
  CSDB ID 67056 (all data & tools)
• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67428 (all data & tools)
• Article ID: 12760
  Tolrà RP, Alonso R, Poschenrieder C, Barceló D, Barceló J "Determination of glucosinolates in rapeseed and Thlaspi caerulescens plants by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry" - Journal of Chromatography A 889(1-2) (2000) 75-81
  

  Liquid chromatography-atmospheric pressure chemical ionization mass spectrometry was used to identify glucosinolates in plant extracts. Optimization of the analytical conditions and the determination of the method detection limit was performed using commercial 2-propenylglucosinolate (sinigrin). Optimal values for the following parameters were determined: nebulization pressure, gas temperature, flux of drying gas, capillar voltage, corona current and fragmentor conditions. The method detection limit for sinigrin was 2.85 ng. For validation of the method the glucosinolates in reference material (rapeseed) from the Community Bureau of Reference Materials (BCR) were analyzed. The method was applied for the determination of glucosinolates in Thlaspi caerulescens plants.

  Thlaspi caerulescence; plant materials; glucosinolates; sulfur compounds; carbohydrates

  NCBI PubMed ID: 10985538
  Publication DOI: 10.1016/s0021-9673(00)00373-3
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Correspondence: juan.barcelo@uab.es
  Institutions: Laboratorio de Fisiología Vegetal, Facultad de Ciencias, Universidad Autónoma de Barcelona, Bellaterra, Spain, Instituto Investigaciones Químicas y Ambientales, CSIC Barcelona, Barcelona, Spain
  Methods: extraction, LC, APCI-MS
  
   
  
  Thlaspi caerulescens, Brassica napus
  CSDB ID 68205 (all data & tools)
• Article ID: 12792
  Vierheilig H, Bennett R, Kiddle G, Kaldorf M, Ludwig-Müller J "Differences in glucosinolate patterns and arbuscular mycorrhizal status of glucosinolate-containing plant species" - New Phytologist 146(2) (2000) 343-352
  

  Under defined laboratory conditions it was shown that two glucosinolate-containing plant species, Tropaeolum majus and Carica papaya, were colonized by arbuscular mycorrhizal (AM) fungi, whereas it was not possible to detect AM fungal structures in other glucosinolate-containing plants (including several Brassicaceae). Benzylglucosinolate was present in all of the T. majus cultivars and in C. papaya it was the major glucosinolate. 2-Phenylethylglucosinolate was found in most of the non-host plants tested. Its absence in the AM host plants indicates a possible role for the isothiocyanate produced from its myrosinase-catalysed hydrolysis as a general AM inhibitory factor in non-host plants. The results suggest that some of the indole glucosinolates might also be involved in preventing AM formation in some of the species. In all plants tested, both AM hosts and non-hosts, the glucosinolate pattern was altered after inoculation with one of three different AM fungi (Glomus mosseae, Glomus intraradices and Gigaspora rosea), indicating signals between AM fungi and plants even before root colonization. The glucosinolate induction was not specifically dependent on the AM fungus. A time-course study in T. majus showed that glucosinolate induction was present during all stages of mycorrhizal colonization.

  Brassicaceae, glucosinolates, arbuscular mycorrhiza, Glomus, Tropaeolum majus

  NCBI PubMed ID: 33862976
  Publication DOI: 10.1046/j.1469-8137.2000.00642.x
  Journal NLM ID: 9882884
  Publisher: Blackwell Publishing
  Correspondence: jutta.ludwig-mueller@mailbox.tu-dresden.de
  Institutions: Institut für Phytopathologie, Christian-Albrechts-Universität, Kiel, Germany, Cellular Metabolism and Enzymology Group, Institute of Food Research, Norwich Research Park, Colney, UK, Biochemistry and Physiology Department, IACR–Rothamsted, Harpenden, UK, Institut für Ökologie, Lehrbereich Umweltwissenschaften, Friedrich-Schiller-Universität, Jena, Germany, Institut für Botanik, Technische Universität Dresden, Dresden, Germany
  Methods: HPLC, extraction
  
   
  
  Tropaeolum majus cv. SKK, Tropaeolum majus cv. Nanum, Tropaeolum majus cv. BGF, Carica papaya, Lepidium sativum, Sinapis alba, Barbarea praecox, Barbarea vulgaris, Nasturtium officinale, Brassica napus, Brassica nigra, Reseda alba, Reseda lutea, Reseda luteola
  CSDB ID 68375 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucobrassicin
Compound class: glycoside, glucosinolate

• Article ID: 12555
  O'Callaghan KJ, Stone PJ, Hu X, Griffiths DW, Davey MR, Cocking EC "Effects of glucosinolates and flavonoids on colonization of the roots of Brassica napus by Azorhizobium caulinodans ORS571" - Applied and Environmental Microbiology 66(5) (2000) 2185-2191
  

  Plants of Brassica napus were assessed quantitatively for their susceptibility to lateral root crack colonization by Azorhizobium caulinodans ORS571(pXLGD4) (a rhizobial strain carrying the lacZ reporter gene) and for the concentration of glucosinolates in their roots by high-pressure liquid chromatography (HPLC). High- and low-glucosinolate-seed (HGS and LGS) varieties exhibited a relatively low and high percentage of colonized lateral roots, respectively. HPLC showed that roots of HGS plants contained a higher concentration of glucosinolates than roots of LGS plants. One LGS variety showing fewer colonized lateral roots than other LGS varieties contained a higher concentration of glucosinolates than other LGS plants. Inoculated HGS plants treated with the flavonoid naringenin showed significantly more colonization than untreated HGS plants. This increase was not mediated by a naringenin-induced lowering of the glucosinolate content of HGS plant roots, nor did naringenin induce bacterial resistance to glucosinolates or increase the growth of bacteria. The erucic acid content of seed did not appear to influence colonization by azorhizobia. Frequently, leaf assays are used to study glucosinolates and plant defense; this study provides data on glucosinolates and bacterial colonization in roots and describes a bacterial reporter gene assay tailored easily to the study of ecologically important phytochemicals that influence bacterial colonization. These data also form a basis for future assessments of the benefits to oilseed rape plants of interaction with plant growth-promoting bacteria, especially diazotrophic bacteria potentially able to extend the benefits of nitrogen fixation to nonlegumes.

  Brassica napus, glucosinolates, Azorhizobium caulinodans ORS571

  NCBI PubMed ID: 10788398
  Publication DOI: 10.1128/AEM.66.5.2185-2191.2000
  Journal NLM ID: 7605801
  Publisher: American Society for Microbiology
  Correspondence: Edward.Cocking@nottingham.ac.uk
  Institutions: Scottish Crop Research Institute, Invergowrie, UK, Plant Science Division, University of Nottingham, Nottingham, UK
  Methods: biological assays
  
   
  
  Brassica napus
  CSDB ID 67198 (all data & tools)
• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67424 (all data & tools)
• Article ID: 12760
  Tolrà RP, Alonso R, Poschenrieder C, Barceló D, Barceló J "Determination of glucosinolates in rapeseed and Thlaspi caerulescens plants by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry" - Journal of Chromatography A 889(1-2) (2000) 75-81
  

  Liquid chromatography-atmospheric pressure chemical ionization mass spectrometry was used to identify glucosinolates in plant extracts. Optimization of the analytical conditions and the determination of the method detection limit was performed using commercial 2-propenylglucosinolate (sinigrin). Optimal values for the following parameters were determined: nebulization pressure, gas temperature, flux of drying gas, capillar voltage, corona current and fragmentor conditions. The method detection limit for sinigrin was 2.85 ng. For validation of the method the glucosinolates in reference material (rapeseed) from the Community Bureau of Reference Materials (BCR) were analyzed. The method was applied for the determination of glucosinolates in Thlaspi caerulescens plants.

  Thlaspi caerulescence; plant materials; glucosinolates; sulfur compounds; carbohydrates

  NCBI PubMed ID: 10985538
  Publication DOI: 10.1016/s0021-9673(00)00373-3
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Correspondence: juan.barcelo@uab.es
  Institutions: Laboratorio de Fisiología Vegetal, Facultad de Ciencias, Universidad Autónoma de Barcelona, Bellaterra, Spain, Instituto Investigaciones Químicas y Ambientales, CSIC Barcelona, Barcelona, Spain
  Methods: extraction, LC, APCI-MS
  
   
  
  Thlaspi caerulescens, Brassica napus
  CSDB ID 68207 (all data & tools)
• Article ID: 12792
  Vierheilig H, Bennett R, Kiddle G, Kaldorf M, Ludwig-Müller J "Differences in glucosinolate patterns and arbuscular mycorrhizal status of glucosinolate-containing plant species" - New Phytologist 146(2) (2000) 343-352
  

  Under defined laboratory conditions it was shown that two glucosinolate-containing plant species, Tropaeolum majus and Carica papaya, were colonized by arbuscular mycorrhizal (AM) fungi, whereas it was not possible to detect AM fungal structures in other glucosinolate-containing plants (including several Brassicaceae). Benzylglucosinolate was present in all of the T. majus cultivars and in C. papaya it was the major glucosinolate. 2-Phenylethylglucosinolate was found in most of the non-host plants tested. Its absence in the AM host plants indicates a possible role for the isothiocyanate produced from its myrosinase-catalysed hydrolysis as a general AM inhibitory factor in non-host plants. The results suggest that some of the indole glucosinolates might also be involved in preventing AM formation in some of the species. In all plants tested, both AM hosts and non-hosts, the glucosinolate pattern was altered after inoculation with one of three different AM fungi (Glomus mosseae, Glomus intraradices and Gigaspora rosea), indicating signals between AM fungi and plants even before root colonization. The glucosinolate induction was not specifically dependent on the AM fungus. A time-course study in T. majus showed that glucosinolate induction was present during all stages of mycorrhizal colonization.

  Brassicaceae, glucosinolates, arbuscular mycorrhiza, Glomus, Tropaeolum majus

  NCBI PubMed ID: 33862976
  Publication DOI: 10.1046/j.1469-8137.2000.00642.x
  Journal NLM ID: 9882884
  Publisher: Blackwell Publishing
  Correspondence: jutta.ludwig-mueller@mailbox.tu-dresden.de
  Institutions: Institut für Phytopathologie, Christian-Albrechts-Universität, Kiel, Germany, Cellular Metabolism and Enzymology Group, Institute of Food Research, Norwich Research Park, Colney, UK, Biochemistry and Physiology Department, IACR–Rothamsted, Harpenden, UK, Institut für Ökologie, Lehrbereich Umweltwissenschaften, Friedrich-Schiller-Universität, Jena, Germany, Institut für Botanik, Technische Universität Dresden, Dresden, Germany
  Methods: HPLC, extraction
  
   
  
  Tropaeolum majus cv. SKK, Tropaeolum majus cv. Nanum, Tropaeolum majus cv. BGF, Carica papaya, Lepidium sativum, Sinapis alba, Barbarea praecox, Barbarea vulgaris, Nasturtium officinale, Brassica napus, Brassica nigra, Reseda alba, Reseda lutea, Reseda luteola
  CSDB ID 68379 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: neoglucobrassicin
Compound class: glycoside, glucosinolate

• Article ID: 12555
  O'Callaghan KJ, Stone PJ, Hu X, Griffiths DW, Davey MR, Cocking EC "Effects of glucosinolates and flavonoids on colonization of the roots of Brassica napus by Azorhizobium caulinodans ORS571" - Applied and Environmental Microbiology 66(5) (2000) 2185-2191
  

  Plants of Brassica napus were assessed quantitatively for their susceptibility to lateral root crack colonization by Azorhizobium caulinodans ORS571(pXLGD4) (a rhizobial strain carrying the lacZ reporter gene) and for the concentration of glucosinolates in their roots by high-pressure liquid chromatography (HPLC). High- and low-glucosinolate-seed (HGS and LGS) varieties exhibited a relatively low and high percentage of colonized lateral roots, respectively. HPLC showed that roots of HGS plants contained a higher concentration of glucosinolates than roots of LGS plants. One LGS variety showing fewer colonized lateral roots than other LGS varieties contained a higher concentration of glucosinolates than other LGS plants. Inoculated HGS plants treated with the flavonoid naringenin showed significantly more colonization than untreated HGS plants. This increase was not mediated by a naringenin-induced lowering of the glucosinolate content of HGS plant roots, nor did naringenin induce bacterial resistance to glucosinolates or increase the growth of bacteria. The erucic acid content of seed did not appear to influence colonization by azorhizobia. Frequently, leaf assays are used to study glucosinolates and plant defense; this study provides data on glucosinolates and bacterial colonization in roots and describes a bacterial reporter gene assay tailored easily to the study of ecologically important phytochemicals that influence bacterial colonization. These data also form a basis for future assessments of the benefits to oilseed rape plants of interaction with plant growth-promoting bacteria, especially diazotrophic bacteria potentially able to extend the benefits of nitrogen fixation to nonlegumes.

  Brassica napus, glucosinolates, Azorhizobium caulinodans ORS571

  NCBI PubMed ID: 10788398
  Publication DOI: 10.1128/AEM.66.5.2185-2191.2000
  Journal NLM ID: 7605801
  Publisher: American Society for Microbiology
  Correspondence: Edward.Cocking@nottingham.ac.uk
  Institutions: Scottish Crop Research Institute, Invergowrie, UK, Plant Science Division, University of Nottingham, Nottingham, UK
  Methods: biological assays
  
   
  
  Brassica napus
  CSDB ID 67200 (all data & tools)
• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67425 (all data & tools)
• Article ID: 12792
  Vierheilig H, Bennett R, Kiddle G, Kaldorf M, Ludwig-Müller J "Differences in glucosinolate patterns and arbuscular mycorrhizal status of glucosinolate-containing plant species" - New Phytologist 146(2) (2000) 343-352
  

  Under defined laboratory conditions it was shown that two glucosinolate-containing plant species, Tropaeolum majus and Carica papaya, were colonized by arbuscular mycorrhizal (AM) fungi, whereas it was not possible to detect AM fungal structures in other glucosinolate-containing plants (including several Brassicaceae). Benzylglucosinolate was present in all of the T. majus cultivars and in C. papaya it was the major glucosinolate. 2-Phenylethylglucosinolate was found in most of the non-host plants tested. Its absence in the AM host plants indicates a possible role for the isothiocyanate produced from its myrosinase-catalysed hydrolysis as a general AM inhibitory factor in non-host plants. The results suggest that some of the indole glucosinolates might also be involved in preventing AM formation in some of the species. In all plants tested, both AM hosts and non-hosts, the glucosinolate pattern was altered after inoculation with one of three different AM fungi (Glomus mosseae, Glomus intraradices and Gigaspora rosea), indicating signals between AM fungi and plants even before root colonization. The glucosinolate induction was not specifically dependent on the AM fungus. A time-course study in T. majus showed that glucosinolate induction was present during all stages of mycorrhizal colonization.

  Brassicaceae, glucosinolates, arbuscular mycorrhiza, Glomus, Tropaeolum majus

  NCBI PubMed ID: 33862976
  Publication DOI: 10.1046/j.1469-8137.2000.00642.x
  Journal NLM ID: 9882884
  Publisher: Blackwell Publishing
  Correspondence: jutta.ludwig-mueller@mailbox.tu-dresden.de
  Institutions: Institut für Phytopathologie, Christian-Albrechts-Universität, Kiel, Germany, Cellular Metabolism and Enzymology Group, Institute of Food Research, Norwich Research Park, Colney, UK, Biochemistry and Physiology Department, IACR–Rothamsted, Harpenden, UK, Institut für Ökologie, Lehrbereich Umweltwissenschaften, Friedrich-Schiller-Universität, Jena, Germany, Institut für Botanik, Technische Universität Dresden, Dresden, Germany
  Methods: HPLC, extraction
  
   
  
  Tropaeolum majus cv. SKK, Tropaeolum majus cv. Nanum, Tropaeolum majus cv. BGF, Carica papaya, Lepidium sativum, Sinapis alba, Barbarea praecox, Barbarea vulgaris, Nasturtium officinale, Brassica napus, Brassica nigra, Reseda alba, Reseda lutea, Reseda luteola
  CSDB ID 68380 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucobrassicin
Compound class: glycoside

• Article ID: 12605
  Preobrazhenskaya MN, Korolev AM "Indole derivatives in vegetables of the Cruciferae family" - Russian Journal of Bioorganic Chemistry 26(2) (2000) 85-97
  

  The chemical background of the biological activities of vegetables of the Cruciferae family is considered. These vegetables contain alkaloids of the glucobrassicin group that are decomposed by the enzyme myrosinase (thioglucosidase, EC 3.2.3.1) released upon damage to the plant cells. This results in several indole derivatives, with ascorbigen and indole-3-carbinol predominating. In the gastrointestinal tract, these compounds form 5H,11H-indolo[3,2-b]carbazole, a natural ligand of the aromatic hydrocarbon receptor (Ah receptor) and a functional analogue of 2,3,7,8-tetrachlorodibenzo-p-dioxin, a dangerous xenobiotic. The indolocarbazole—Ah receptor complex activates the gene of CYP1A1, an isoenzyme of cytochrome P450-dependent monoamine oxidase, which enhances the 2-hydroxylation (inactivation) of estrogens. In its turn, the resulting lowered level of estrogens inhibits the growth of hormone-dependent tumors or prevents their appearance. The mechanism of xenobiotic inactivation, underlying the anticarcinogenic action of food products including vegetables of the Cruciferae family and some homogeneous indole compounds, is similar. Some other effects of nutrient indole compounds, e.g., the inhibition of expression of the cyclin-dependent kinase 6 (CDK6) by indole-3-carbinol that leads to the cell cycle arrest in G1 phase, are also considered. Analysis of the biological effects of the Cruciferae diet has helped start clinical studies of indole-3-carbinol as an antitumor and anticarcinogenic remedy for patients with a high risk of tumor diseases.

  aromatic hydrocarbon receptor, ascorbigen, cytochrome P450 monoamine oxidase, glucobrassicin alkaloids, indole-3-carbinol, indolocarbazole

  NCBI PubMed ID: 10808405
  Publication DOI: 10.1007/BF02759153
  Journal NLM ID: 9420101
  Publisher: Springer Science and Business Media
  Correspondence: Preobrazhenskaya MN
  Institutions: Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russia
  
   
  
  (Brassicaceae)
  CSDB ID 67372 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: neoglucobrassicin
Compound class: glycoside

• Article ID: 12605
  Preobrazhenskaya MN, Korolev AM "Indole derivatives in vegetables of the Cruciferae family" - Russian Journal of Bioorganic Chemistry 26(2) (2000) 85-97
  

  The chemical background of the biological activities of vegetables of the Cruciferae family is considered. These vegetables contain alkaloids of the glucobrassicin group that are decomposed by the enzyme myrosinase (thioglucosidase, EC 3.2.3.1) released upon damage to the plant cells. This results in several indole derivatives, with ascorbigen and indole-3-carbinol predominating. In the gastrointestinal tract, these compounds form 5H,11H-indolo[3,2-b]carbazole, a natural ligand of the aromatic hydrocarbon receptor (Ah receptor) and a functional analogue of 2,3,7,8-tetrachlorodibenzo-p-dioxin, a dangerous xenobiotic. The indolocarbazole—Ah receptor complex activates the gene of CYP1A1, an isoenzyme of cytochrome P450-dependent monoamine oxidase, which enhances the 2-hydroxylation (inactivation) of estrogens. In its turn, the resulting lowered level of estrogens inhibits the growth of hormone-dependent tumors or prevents their appearance. The mechanism of xenobiotic inactivation, underlying the anticarcinogenic action of food products including vegetables of the Cruciferae family and some homogeneous indole compounds, is similar. Some other effects of nutrient indole compounds, e.g., the inhibition of expression of the cyclin-dependent kinase 6 (CDK6) by indole-3-carbinol that leads to the cell cycle arrest in G1 phase, are also considered. Analysis of the biological effects of the Cruciferae diet has helped start clinical studies of indole-3-carbinol as an antitumor and anticarcinogenic remedy for patients with a high risk of tumor diseases.

  aromatic hydrocarbon receptor, ascorbigen, cytochrome P450 monoamine oxidase, glucobrassicin alkaloids, indole-3-carbinol, indolocarbazole

  NCBI PubMed ID: 10808405
  Publication DOI: 10.1007/BF02759153
  Journal NLM ID: 9420101
  Publisher: Springer Science and Business Media
  Correspondence: Preobrazhenskaya MN
  Institutions: Institute of New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russia
  
   
  
  (Brassicaceae)
  CSDB ID 67373 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: 4-hydroxybrassicin
Compound class: glycoside, glucosinolate

• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67426 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: gluconasturtiin, gluconasturtin
Compound class: glycoside, glucosinolate

• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67427 (all data & tools)
• Article ID: 12760
  Tolrà RP, Alonso R, Poschenrieder C, Barceló D, Barceló J "Determination of glucosinolates in rapeseed and Thlaspi caerulescens plants by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry" - Journal of Chromatography A 889(1-2) (2000) 75-81
  

  Liquid chromatography-atmospheric pressure chemical ionization mass spectrometry was used to identify glucosinolates in plant extracts. Optimization of the analytical conditions and the determination of the method detection limit was performed using commercial 2-propenylglucosinolate (sinigrin). Optimal values for the following parameters were determined: nebulization pressure, gas temperature, flux of drying gas, capillar voltage, corona current and fragmentor conditions. The method detection limit for sinigrin was 2.85 ng. For validation of the method the glucosinolates in reference material (rapeseed) from the Community Bureau of Reference Materials (BCR) were analyzed. The method was applied for the determination of glucosinolates in Thlaspi caerulescens plants.

  Thlaspi caerulescence; plant materials; glucosinolates; sulfur compounds; carbohydrates

  NCBI PubMed ID: 10985538
  Publication DOI: 10.1016/s0021-9673(00)00373-3
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Correspondence: juan.barcelo@uab.es
  Institutions: Laboratorio de Fisiología Vegetal, Facultad de Ciencias, Universidad Autónoma de Barcelona, Bellaterra, Spain, Instituto Investigaciones Químicas y Ambientales, CSIC Barcelona, Barcelona, Spain
  Methods: extraction, LC, APCI-MS
  
   
  
  Thlaspi caerulescens, Brassica napus
  CSDB ID 68206 (all data & tools)
• Article ID: 12792
  Vierheilig H, Bennett R, Kiddle G, Kaldorf M, Ludwig-Müller J "Differences in glucosinolate patterns and arbuscular mycorrhizal status of glucosinolate-containing plant species" - New Phytologist 146(2) (2000) 343-352
  

  Under defined laboratory conditions it was shown that two glucosinolate-containing plant species, Tropaeolum majus and Carica papaya, were colonized by arbuscular mycorrhizal (AM) fungi, whereas it was not possible to detect AM fungal structures in other glucosinolate-containing plants (including several Brassicaceae). Benzylglucosinolate was present in all of the T. majus cultivars and in C. papaya it was the major glucosinolate. 2-Phenylethylglucosinolate was found in most of the non-host plants tested. Its absence in the AM host plants indicates a possible role for the isothiocyanate produced from its myrosinase-catalysed hydrolysis as a general AM inhibitory factor in non-host plants. The results suggest that some of the indole glucosinolates might also be involved in preventing AM formation in some of the species. In all plants tested, both AM hosts and non-hosts, the glucosinolate pattern was altered after inoculation with one of three different AM fungi (Glomus mosseae, Glomus intraradices and Gigaspora rosea), indicating signals between AM fungi and plants even before root colonization. The glucosinolate induction was not specifically dependent on the AM fungus. A time-course study in T. majus showed that glucosinolate induction was present during all stages of mycorrhizal colonization.

  Brassicaceae, glucosinolates, arbuscular mycorrhiza, Glomus, Tropaeolum majus

  NCBI PubMed ID: 33862976
  Publication DOI: 10.1046/j.1469-8137.2000.00642.x
  Journal NLM ID: 9882884
  Publisher: Blackwell Publishing
  Correspondence: jutta.ludwig-mueller@mailbox.tu-dresden.de
  Institutions: Institut für Phytopathologie, Christian-Albrechts-Universität, Kiel, Germany, Cellular Metabolism and Enzymology Group, Institute of Food Research, Norwich Research Park, Colney, UK, Biochemistry and Physiology Department, IACR–Rothamsted, Harpenden, UK, Institut für Ökologie, Lehrbereich Umweltwissenschaften, Friedrich-Schiller-Universität, Jena, Germany, Institut für Botanik, Technische Universität Dresden, Dresden, Germany
  Methods: HPLC, extraction
  
   
  
  Tropaeolum majus cv. SKK, Tropaeolum majus cv. Nanum, Tropaeolum majus cv. BGF, Carica papaya, Lepidium sativum, Sinapis alba, Barbarea praecox, Barbarea vulgaris, Nasturtium officinale, Brassica napus, Brassica nigra, Reseda alba, Reseda lutea, Reseda luteola
  CSDB ID 68376 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucobarbarin
Compound class: glycoside, glucosinolate

• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67429 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucoraphenin
Compound class: glycoside, glucosinolate

• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67430 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: gluconapin
Compound class: glycoside, glucosinolate

• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67432 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucobrassicianapin
Compound class: glycoside, glucosinolate

• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67433 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: progoitrin
Compound class: glycoside, glucosinolate

• Article ID: 12611
  Rask L, Andréasson E, Ekbom B, Eriksson S, Pontoppidan B, Meijer J "Myrosinase: gene family evolution and herbivore defense in Brassicaceae" - Plant Molecular Biology 42(1) (2000) 93-113
  

  Glucosinolates are a category of secondary products present primarily in species of the order Capparales. When tissue is damaged, for example by herbivory, glucosinolates are degraded in a reaction catalyzed by thioglucosidases, denoted myrosinases, also present in these species. Thereby, toxic compounds such as nitriles, isothiocyanates, epithionitriles and thiocyanates are released. The glucosinolate-myrosinase system is generally believed to be part of the plant's defense against insects, and possibly also against pathogens. In this review, the evolution of the system and its impact on the interaction between plants and insects are discussed. Further, data suggesting additional functions in the defense against pathogens and in sulfur metabolism are reviewed.

  cyanogenic glucosides, myrosinase, glucosinolates, O-β-glucosidase, plant–insect interaction

  NCBI PubMed ID: 10688132
  Publication DOI: 10.1023/A:1006380021658
  Journal NLM ID: 9106343
  Publisher: Dordrecht: Kluwer Academic
  Institutions: Department of Medical Biochemistry and Microbiology, Uppsala University, Uppsala, Sweden, Department of Plant Biology, Swedish University of Agricultural Sciences, Uppsala, Sweden, Department of Entomology, Swedish University of Agricultural Sciences, Uppsala, Sweden
  
   
  
  (Brassicaceae)
  CSDB ID 67434 (all data & tools)
• Article ID: 12760
  Tolrà RP, Alonso R, Poschenrieder C, Barceló D, Barceló J "Determination of glucosinolates in rapeseed and Thlaspi caerulescens plants by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry" - Journal of Chromatography A 889(1-2) (2000) 75-81
  

  Liquid chromatography-atmospheric pressure chemical ionization mass spectrometry was used to identify glucosinolates in plant extracts. Optimization of the analytical conditions and the determination of the method detection limit was performed using commercial 2-propenylglucosinolate (sinigrin). Optimal values for the following parameters were determined: nebulization pressure, gas temperature, flux of drying gas, capillar voltage, corona current and fragmentor conditions. The method detection limit for sinigrin was 2.85 ng. For validation of the method the glucosinolates in reference material (rapeseed) from the Community Bureau of Reference Materials (BCR) were analyzed. The method was applied for the determination of glucosinolates in Thlaspi caerulescens plants.

  Thlaspi caerulescence; plant materials; glucosinolates; sulfur compounds; carbohydrates

  NCBI PubMed ID: 10985538
  Publication DOI: 10.1016/s0021-9673(00)00373-3
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Correspondence: juan.barcelo@uab.es
  Institutions: Laboratorio de Fisiología Vegetal, Facultad de Ciencias, Universidad Autónoma de Barcelona, Bellaterra, Spain, Instituto Investigaciones Químicas y Ambientales, CSIC Barcelona, Barcelona, Spain
  Methods: extraction, LC, APCI-MS
  
   
  
  Thlaspi caerulescens, Brassica napus
  CSDB ID 68201 (all data & tools)
• Article ID: 12792
  Vierheilig H, Bennett R, Kiddle G, Kaldorf M, Ludwig-Müller J "Differences in glucosinolate patterns and arbuscular mycorrhizal status of glucosinolate-containing plant species" - New Phytologist 146(2) (2000) 343-352
  

  Under defined laboratory conditions it was shown that two glucosinolate-containing plant species, Tropaeolum majus and Carica papaya, were colonized by arbuscular mycorrhizal (AM) fungi, whereas it was not possible to detect AM fungal structures in other glucosinolate-containing plants (including several Brassicaceae). Benzylglucosinolate was present in all of the T. majus cultivars and in C. papaya it was the major glucosinolate. 2-Phenylethylglucosinolate was found in most of the non-host plants tested. Its absence in the AM host plants indicates a possible role for the isothiocyanate produced from its myrosinase-catalysed hydrolysis as a general AM inhibitory factor in non-host plants. The results suggest that some of the indole glucosinolates might also be involved in preventing AM formation in some of the species. In all plants tested, both AM hosts and non-hosts, the glucosinolate pattern was altered after inoculation with one of three different AM fungi (Glomus mosseae, Glomus intraradices and Gigaspora rosea), indicating signals between AM fungi and plants even before root colonization. The glucosinolate induction was not specifically dependent on the AM fungus. A time-course study in T. majus showed that glucosinolate induction was present during all stages of mycorrhizal colonization.

  Brassicaceae, glucosinolates, arbuscular mycorrhiza, Glomus, Tropaeolum majus

  NCBI PubMed ID: 33862976
  Publication DOI: 10.1046/j.1469-8137.2000.00642.x
  Journal NLM ID: 9882884
  Publisher: Blackwell Publishing
  Correspondence: jutta.ludwig-mueller@mailbox.tu-dresden.de
  Institutions: Institut für Phytopathologie, Christian-Albrechts-Universität, Kiel, Germany, Cellular Metabolism and Enzymology Group, Institute of Food Research, Norwich Research Park, Colney, UK, Biochemistry and Physiology Department, IACR–Rothamsted, Harpenden, UK, Institut für Ökologie, Lehrbereich Umweltwissenschaften, Friedrich-Schiller-Universität, Jena, Germany, Institut für Botanik, Technische Universität Dresden, Dresden, Germany
  Methods: HPLC, extraction
  
   
  
  Tropaeolum majus cv. SKK, Tropaeolum majus cv. Nanum, Tropaeolum majus cv. BGF, Carica papaya, Lepidium sativum, Sinapis alba, Barbarea praecox, Barbarea vulgaris, Nasturtium officinale, Brassica napus, Brassica nigra, Reseda alba, Reseda lutea, Reseda luteola
  CSDB ID 68369 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucobrassicin
Compound class: glycoside, glucosinolate
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 12884
  Yudina LN, Korolev AM, Reznikova MI, Preobrazhenskaya MN "Investigation of neoascorbigen" - Chemistry of Heterocyclic Compounds 36(2) (2000) 144–151
  

  The synthesis of N-methoxyascorbigen (neoascorbigen) — a natural substance from plants of the Cruciferae family — and also N-ethoxyascorbigen is described. In an acidic media under drastic conditions N-alkoxyascorbigens undergo transformations with the release of ascorbic acid and the formation of oligomers of 1-alkoxy-3-methyleneindolenine or with opening of the lactone ring, decarboxylation, and dehydration and the formation of 2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enone. Amides of neoascorbigen, 3-O-methylglycoside of N-ethoxyascorbigen, and the product of the reduction of N-ethoxyascorbigen by sodium borohydride were obtained for the first time.

  2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enones, neoascorbigen, N-ethoxyascorbigen

  Publication DOI: 10.1007/BF02283542
  Journal NLM ID: 0050006
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: Scientific-Research Institute of the Search for New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russia
  
   
  
  (Cruciferae)
  CSDB ID 68859 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: neoglucobrassicin
Compound class: glycoside, glucosinolate
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 12884
  Yudina LN, Korolev AM, Reznikova MI, Preobrazhenskaya MN "Investigation of neoascorbigen" - Chemistry of Heterocyclic Compounds 36(2) (2000) 144–151
  

  The synthesis of N-methoxyascorbigen (neoascorbigen) — a natural substance from plants of the Cruciferae family — and also N-ethoxyascorbigen is described. In an acidic media under drastic conditions N-alkoxyascorbigens undergo transformations with the release of ascorbic acid and the formation of oligomers of 1-alkoxy-3-methyleneindolenine or with opening of the lactone ring, decarboxylation, and dehydration and the formation of 2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enone. Amides of neoascorbigen, 3-O-methylglycoside of N-ethoxyascorbigen, and the product of the reduction of N-ethoxyascorbigen by sodium borohydride were obtained for the first time.

  2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enones, neoascorbigen, N-ethoxyascorbigen

  Publication DOI: 10.1007/BF02283542
  Journal NLM ID: 0050006
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: Scientific-Research Institute of the Search for New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russia
  
   
  
  (Cruciferae)
  CSDB ID 68860 (all data & tools)