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Indole glucosinolate breakdown and its biological effects

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Abstract

Most species in the Brassicaceae produce one or more indole glucosinolates. In addition to the parent indol-3-ylmethylglucosinolate (IMG), other commonly encountered indole glucosinolates are 1-methoxyIMG, 4-hydroxyIMG, and 4-methoxyIMG. Upon tissue disruption, enzymatic hydrolysis of IMG produces an unstable aglucone, which reacts rapidly to form indole-3-acetonitrile and indol-3-ylmethyl isothiocyanate. The isothiocyanate, in turn, can react with water, ascorbate, glutathione, amino acids, and other plant metabolites to produce a variety of physiologically active indole compounds. Myrosinase-initiated breakdown of the substituted indole glucosinolates proceeds in a similar manner to that of IMG. Induction of indole glucosinolate production in response to biotic stress, experiments with mutant plants, and artificial diet assays suggest a significant role for indole glucosinolates in plant defense. However, some crucifer-feeding specialist herbivores recognize indole glucosinolates and their breakdown products as oviposition and/or feeding stimulants. In mammalian diets, IMG can have both beneficial and deleterious effects. Most IMG breakdown products induce the synthesis of phase 1 detoxifying enzymes, which may in some cases prevent carcinogenesis, but in other cases promote carcinogenesis. Recent advances in indole glucosinolate research have been fueled by their occurrence in the well-studied model plant Arabidopsis thaliana. Knowledge gained from genetic and biochemical experiments with A. thaliana can be applied to gain new insight into the ecological and nutritional properties of indole glucosinolates in other plant species.

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References

  • Agerbirk N, Bjergegaard C, Olsen CE, Sørensen H (1996) Kinetic investigation of the transformations of indol-3-ylcarbinol into oligomeric indolyl compounds based on micellar electrokinetic capillary chromatography. J Chromatogr A 745:239–248

    Article  CAS  Google Scholar 

  • Agerbirk N, Olsen CE, Sørensen H (1998) Initial and final products, nitriles and ascorbigens produced in myrosinase-catalyzed hydrolysis of indole glucosinolates. J Agric Food Chem 46:1563–1571

    Article  CAS  Google Scholar 

  • Agerbirk N, Petersen BL, Olsen CE et al (2001) 1,4-Dimethoxyglucobrassicin in Barbarea and 4-hydroxyglucobrassicin in Arabidopsis and Brassica. J Agric Food Chem 49:1502–1507

    Article  PubMed  CAS  Google Scholar 

  • Agerbirk N, Ørgaard M, Nielsen JK (2003) Glucosinolates, flea beetle resistance, and leaf pubescence as taxonomic characters in the genus Barbarea (Brassicaceae). Phytochemistry 63:69–80

    Article  PubMed  CAS  Google Scholar 

  • Aleksandrova LG, Korolev AM, Preobrazhenskaya MN (1992) Study of natural ascorbigen and related compounds by HPLC. Food Chem 45:61–69

    Article  CAS  Google Scholar 

  • Anderton MJ, Manson MM, Verschoyle RD et al (2004) Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice. Clin Cancer Res 10:5233–5241

    Article  PubMed  CAS  Google Scholar 

  • Baird WM, Hooven LA, Mahadevan B (2005) Carcinogenic polycyclic aromatic hydrocarbon-DNA adducts and mechanism of action. Environ Mol Mutagen 45:106–114

    Article  PubMed  CAS  Google Scholar 

  • Barth C, Jander G (2006) Arabidopsis myrosinases TGG1 and TGG2 have redundant function in glucosinolate breakdown and insect defense. Plant J 46:549–562

    Article  PubMed  CAS  Google Scholar 

  • Bartlet E, Kiddle G, Williams I, Wallsgrove R (1999) Wound-induced increases in the glucosinolate content of oilseed rape and their effect on subsequent herbivory by a crucifer specialist. Entomol Exp Appl 91:163–167

    Article  CAS  Google Scholar 

  • Bellostas N, Kachlicki P, Sørensen JC, Sørensen H (2007) Glucosinolate profiling of B. oleracea varieties used for food. Sci Hort 114:234–242

    Article  CAS  Google Scholar 

  • Bennet RN, Kiddle G, Wallsgrove RM (1997) Involvement of cytochrome P450 in glucosinolate biosynthesis in white mustard (a biochemical anomaly). Plant Physiol 114:1283–1291

    Google Scholar 

  • Bennet RN, Mellon FA, Kroon PA (2004) Screening crucifer seeds as sources of specific intact glucosinolates using ion-pair high-performance liquid chromatography negative ion electrospray mass spectrometry. J Agric Food Chem 52:428–438

    Article  CAS  Google Scholar 

  • Birch ANE, Griffiths DW, Hopkins RJ et al (1992) Glucosinolate responses of Swede, kale, forage and oilseed rape to root damage by turnip root fly (Delia floralis) larvae. J Sci Food Agric 60:1–9

    Article  CAS  Google Scholar 

  • Birch ANE, Griffiths DW, Hopkins RJ, MacFarlane-Smith WH (1996) A time-course study of chemical and physiological responses in Brassicas induced by turnip root fly (Delia floralis) larval feeding. Entomol Exp Appl 80:221–223

    Article  CAS  Google Scholar 

  • Bjeldanes LF, Kim JY, Grose KR et al (1991) Aromatic hydrocarbon responsiveness-receptor agonists generated from indole-3-carbinol in vitro and in vivo: comparisons with 2,3,7,8-tetrachlorodibenzo-p-dioxin. Proc Natl Acad Sci USA 88:9543–9547

    Article  PubMed  CAS  Google Scholar 

  • Bodnaryk RP (1992) Effects of wounding on glucosinolates in the cotyledons of oilseed rape and mustard. Phytochemistry 31:2671–2677

    Article  CAS  Google Scholar 

  • Bodnaryk RP (1994) Potent effect of jasmonates on indole glucosinolates in oilseed rape and mustard. Phytochemistry 35:301–305

    Article  CAS  Google Scholar 

  • Bones AM, Rossiter JT (2006) The enzymic and chemically induced decomposition of glucosinolates. Phytochemistry 67:1053–1067

    Article  PubMed  CAS  Google Scholar 

  • Bonnesen C, Stephensen PU, Andersen O et al (1999) Modulation of cytochrome P-450 and glutathione S-transferase isoform expression in vivo by intact and degraded indolyl glucosinolates. Nutr Cancer 33:178–187

    Article  PubMed  CAS  Google Scholar 

  • Bonnesen C, Eggleston IM, Hayes JD (2001) Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines. Cancer Res 61:6120–6130

    PubMed  CAS  Google Scholar 

  • Brader G, Tas E, Palva ET (2001) Jasmonate-dependent induction of indole glucosinolates in Arabidopsis by culture filtrates of the nonspecific pathogen Erwinia carotovora. Plant Physiol 126:849–860

    Article  PubMed  CAS  Google Scholar 

  • Bradfield CA, Bjeldanes LF (1987) High-performance liquid chromatographic analysis of anticarcinogenic indoles in Brassica oleracea. J Agric Food Chem 35:46–49

    Article  CAS  Google Scholar 

  • Brown PD, Tokuhisa JG, Reichelt M, Gershenzon J (2003) Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana. Phytochemistry 62:471–481

    Article  PubMed  CAS  Google Scholar 

  • Burow M, Wittstock U (2008) Regulation and function of specifier proteins in plants. Phytochem Rev

  • Burow M, Markert J, Gershenzon J, Wittstock U (2006) Comparative biochemical characterization of nitrile-forming proteins from plants and insects that alter myrosinase-catalysed hydrolysis of glucosinolates. FEBS J 273:2432–2446

    Article  PubMed  CAS  Google Scholar 

  • Burow M, Rice M, Hause B et al (2007a) Cell- and tissue-specific localization and regulation of the epithiospecifier protein in Arabidopsis thaliana. Plant Mol Biol 64:173–185

    Article  PubMed  CAS  Google Scholar 

  • Burow M, Zhang ZY, Ober JA et al (2007b) ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis. Phytochemistry 69:663–671

    Article  PubMed  CAS  Google Scholar 

  • Buskov S (2001) Glucosinolates, glucosinolate hydrolysis products and lipids: characterization by packed column chromatographic techniques NMR and MS. Thesis, Chemistry Department, The Royal Veterinary and Agricultural University, Copenhagen

  • Buskov S, Hansen LB, Olsen CE et al (2000a) Determination of ascorbigens in autolysates of various Brassica species using supercritical fluid chromatography. J Agric Food Chem 48:2693–2701

    Article  PubMed  CAS  Google Scholar 

  • Buskov S, Olsen CE, Sørensen H, Sørensen S (2000b) Supercritical fluid chromatography as basis for identification and quantitative determination of indol-3-ylmethyl oligomers and ascorbigens. J Biochem Biophys Methods 43:175–195

    Article  PubMed  CAS  Google Scholar 

  • Cartea ME, Velasco P, Obregón S et al (2008) Seasonal variation in glucosinolate content in Brassica oleracea crops grown in northwestern Spain. Phytochemistry 69:403–410

    Article  PubMed  CAS  Google Scholar 

  • Celenza J, Bender J (2008) Crosstalk among tryptophan secondary metabolism pathways. Phytochem Rev

  • Celenza JL, Quiel JA, Smolen GA et al (2005) The Arabidopsis ATR1 Myb transcription factor controls indolic glucosinolate homeostasis. Plant Physiol 137:253–262

    Article  PubMed  CAS  Google Scholar 

  • Chavadej S, Brisson N, McNeil JN, De Luca V (1994) Redirection of tryptophan leads to production of low indole glucosinolate canola. Proc Natl Acad Sci USA 91:2166–2170

    Article  PubMed  CAS  Google Scholar 

  • Chevolleau S, Gasc N, Rollin P, Tulliez J (1997) Enzymatic, chemical, and thermal breakdown of 3H-Labeled glucobrassicin, the parent indole glucosinolate. J Agric Food Chem 45:4290–4296

    Article  CAS  Google Scholar 

  • De Vos M, Kriksunov K, Jander G (2008) Indole-3-acetonitrile production from indole glucosinolates deters oviposition by Pieris rapae (white cabbage butterfly). Plant Physiol 146:916–926

    Article  PubMed  CAS  Google Scholar 

  • Doughty KJ, Porter AJR, Morton AM et al (1991) Variation in the glucosinolate content of oilseed rape (Brassica napus L.) leaves. II. Response to infection by Alternaria brassicae (Berk.) Sacc. Ann Appl Biol 118:469–477

    Article  CAS  Google Scholar 

  • Doughty KJ, Kiddle GA, Pye BJ et al (1995) Selective induction of glucosinolate in oilseed rape leaves by methyl jasmonate. Phytochemistry 38:347–350

    Article  CAS  Google Scholar 

  • El Sayed G, Louveaux A, Mavratzotis M et al (1996) Effects of glucobrassicin, epigoitrin and related breakdown products on locusts feeding: Shouwia purpurea and desert locust relationships. Entomol Exp Appl 78:231–236

    Article  CAS  Google Scholar 

  • Elliott MC, Stowe BB (1970) A novel sulphonated natural indole. Phytochemistry 9:1629

    Article  CAS  Google Scholar 

  • Fahey JW, Zalcmann AT, Talalay P (2001) The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56:5–51

    Article  PubMed  CAS  Google Scholar 

  • Frechard A, Fabre N, Pean C et al (2001) Novel indole-type glucosinolates from woad (Isatis tinctoria L.). Tetrahedron Lett 42:9015–9017

    Article  CAS  Google Scholar 

  • Gigolashvili T, Berger B, Mock HP et al (2007) The transcription factor HIG1/MYB51 regulates indolic glucosinolate biosynthesis in Arabidopsis thaliana. Plant J 56:886–890

    Article  CAS  Google Scholar 

  • Glawischnig E, Hansen BG, Olsen CE, Halkier BA (2004) Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis. Proc Natl Acad Sci USA 101:8245–8250

    Article  PubMed  CAS  Google Scholar 

  • Gmelin R, Virtanen AI (1961) Glucobrassicin, der Precursor von SCN−, 3-Indolylacetonitril und Ascorbigen in Brassica oleracea Species. Ann Acad Sci Fenn Ser A II. Chem 107:1–25

    Google Scholar 

  • Griffiths DW, Birch ANE, MacFarlane-Smith WH (1994) Induced changes in the indole glucosinolate content of oil-seed and forage rape (Brassica napus) plant in response to either turnip root fly (Delia floralis) larval feeding or artificial root damage. J Sci Food Agric 65:171–178

    Article  CAS  Google Scholar 

  • Grose KR, Bjeldanes LF (1992) Oligomerization of indole-3-carbinol in aqueous acid. Chem Res Toxicol 5:188–193

    Article  PubMed  CAS  Google Scholar 

  • Halkier BA, Gershenzon J (2006) Biology and biochemistry of glucosinolates. Annu Rev Plant Biol 57:303–333

    Article  PubMed  CAS  Google Scholar 

  • Hanley AB, Parsley KR (1990) Identification of 1-methoxyindolyl-3-methyl isothiocyanate as an indole glucosinolate breakdown product. Phytochemistry 29:769–777

    Article  CAS  Google Scholar 

  • Hanley AB, Belton PS, Fenwick GR, Janes NF (1985) Ring oxygenated glucosinolates of Brassica species. Phytochemistry 24:598–600

    Article  CAS  Google Scholar 

  • Harvey JA, Gols R, Wagenaar R, Bezemer TM (2007) Development of an insect herbivore and its pupal parasitoid reflect differences in direct plant defense. J Chem Ecol 33:1556–1569

    Article  PubMed  CAS  Google Scholar 

  • Higdon JV, Delage B, Williams DE, Dashwood RH (2007) Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis. Pharmacol Res 55:224–236

    Article  PubMed  CAS  Google Scholar 

  • Holst B, Williamson G (2004) A critical review of the bioavailability of glucosinolates and related compounds. Nat Prod Rep 21:425–447

    Article  PubMed  CAS  Google Scholar 

  • Hopkins RJ, Griffiths DW, Birch ANE, McKinlay RG (1998) Influence of increasing herbivore pressure on modification of glucosinolate content of Swedes (Brassica napus spp. rapifera). J Chem Ecol 24:2003–2019

    Article  CAS  Google Scholar 

  • Hrncirik K, Valusek J, Velisek J (2001) Investigation of ascorbigen as a breakdown product of glucobrassicin autolysis in Brassica vegetables. Eur Food Res Technol 212:576–581

    Article  CAS  Google Scholar 

  • Huang XP, Renwick JAA (1993) Differential selection of host plants by two Pieris species: the role of oviposition stimulants and deterrents. Entomol Exp Appl 68:59–69

    Article  Google Scholar 

  • Huang XP, Renwick JAA (1994) Relative activities of glucosinolates as oviposition stimulants for Pieris rapae and P. napi oleracea. J Chem Ecol 20:1025–1037

    Article  CAS  Google Scholar 

  • Irwin RE, Strauss SY, Storz S et al (2003) The role of herbivores in the maintenance of flower color polymorphism in wild radish. Ecology 84:1733–1743

    Article  Google Scholar 

  • Isidoro N, VBartlet E, Ziesmann J, Williams IH (1998) Antennal contact chemosensilla in Psylliodes chrysocephala responding to cruciferous allelochemicals. Physiol Entomol 23:131–138

    Article  Google Scholar 

  • Jensen SK, Michaelsen S, Kachlicki P, Sørensen H (1991) 4-Hydroxyglucobrassicin and degradation products of glucosinolates in relation to unsolved problems with the quality of double low oilseed rape. In: McGregor DI (ed) Eighth int. rapeseed congress. GCIRC 1991 Congress, Saskatchewan, Canada, pp 1359–1364

    Google Scholar 

  • Jongen WM (1996) Glucosinolates in Brassica: occurrence and significance as cancer-modulating agents. Proc Nutr Soc 55:433–446

    Article  PubMed  CAS  Google Scholar 

  • Kim YS, Milner JA (2005) Targets for indole-3-carbinol in cancer prevention. J Nutr Biochem 16:65–73

    Article  PubMed  CAS  Google Scholar 

  • Kim JH, Jander G (2007) Myzus persicae (green peach aphid) feeding on Arabidopsis induces the formation of a deterrent indole glucosinolate. Plant J 49:1008–1019

    PubMed  CAS  Google Scholar 

  • Kim JH, Lee BW, Schroeder FC, Jander G (2008) Identification of indole glucosinolate breakdown products with antifeedant effects on Myzus persicae (green peach aphid). Plant J Advance online publication

  • Kirkegaard JA, Sarvar M (1998) Biofumigation potential of Brassicas I. Variation in glucosinolate profiles of diverse field-grown Brassicas. Plant Soil 201:71–89

    Article  CAS  Google Scholar 

  • Kiss G, Neukom H (1966) Über die Struktur des Ascorbigens. Helv Chim Acta 49:989–992

    Article  CAS  Google Scholar 

  • Kliebenstein DJ, Kroymann J, Brown P et al (2001) Genetic control of natural variation in Arabidopsis glucosinolate accumulation. Plant Physiol 126:811–825

    Article  PubMed  CAS  Google Scholar 

  • Kliebenstein DJ, Figuth A, Mitchell-Olds T (2002) Genetic architecture of plastic methyl jasmonate responses in Arabidopsis thaliana. Genetics 161:1685–1696

    PubMed  CAS  Google Scholar 

  • Kliebenstein DJ, Rowe HC, Denby KJ (2005) Secondary metabolites influence Arabidopsis/Botrytis interactions: variation in host production and pathogen sensitivity. Plant J 44:25–36

    Article  PubMed  CAS  Google Scholar 

  • Koroleva OA, Davies A, Deeken R et al (2000) Identification of a new glucosinolate-rich cell type in Arabidopsis flower stalk. Plant Physiol 124:599–608

    Article  PubMed  CAS  Google Scholar 

  • Loivamäki M, Holopainene JK, Nerg A-M (2004) Chemical changes induced by methyl jasmonate in oilseed rape grown in the laboratory and in the field. J Agric Food Chem 52:7607–7613

    Article  PubMed  CAS  Google Scholar 

  • Loub WD, Wattenberg LW, Davis DW (1975) Aryl hydrocarbon hydroxylase induction in rat tissues by naturally occurring indoles of cruciferous plants. J Natl Cancer Inst 54:985–988

    PubMed  CAS  Google Scholar 

  • Ludwig-Mueller J (2008) Glucosinolate and the clubroot disease: defence compounds or auxin precursors. Phytochem Rev. doi:10.1007/s11101-008-9096-2

    Google Scholar 

  • Ludwig-Müller J, Bendell U, Thermann P et al (1993) Concentrations of indole-3-acetic acid in plants of tolerant and susceptible varieties of Chinese cabbage infected with Plasmodiophora brassicae Woron. New Phytol 125:763–769

    Article  Google Scholar 

  • Ludwig-Müller J, Schubert B, Pieper K et al (1997) Glucosinolate content in susceptible and resistant Chinese cabbage varieties during development of clubroot disease. Phytochemistry 44:407–414

    Article  Google Scholar 

  • Ludwig-Müller J, Bennett RN, Kiddle G et al (1999a) The host range of Plasmodiophora brassicae and its relationship to endogenous glucosinolate content. New Phytol 141:443–458

    Article  Google Scholar 

  • Ludwig-Müller J, Pieper K, Ruppel M et al (1999b) Indole glucosinolate and auxin biosynthesis in Arabidopsis thaliana (L.) Heynh. glucosinolate mutants and the development of clubroot disease. Planta 208:409–419

    Article  PubMed  Google Scholar 

  • Ludwig-Müller J, Bennett RN, Garcia-Garrido JM et al (2002) Reduced arbuscular mycorrhizal root colonization in Tropaeolum majus and Carica papaya after jasmonic acid application can not be attributed to increased glucosinolate levels. J Plant Physiol 159:517–523

    Article  Google Scholar 

  • Martin N, Müller C (2007) Induction of plant responses by a sequestering insect: relationship of glucosinolate concentration and myrosinase activity. Basic Appl Ecol 8:13–25

    Article  CAS  Google Scholar 

  • McDanell R, McLean AE, Hanley AB et al (1987) Differential induction of mixed-function oxidase (MFO) activity in rat liver and intestine by diets containing processed cabbage: correlation with cabbage levels of glucosinolates and glucosinolate hydrolysis products. Food Chem Toxicol 25:363–368

    Article  PubMed  CAS  Google Scholar 

  • McDanell R, McLean AE, Hanley AB et al (1988) Chemical and biological properties of indole glucosinolates (glucobrassicins): a review. Food Chem Toxicol 26:59–70

    Article  PubMed  CAS  Google Scholar 

  • Mewis I, Appel HM, Hom A et al (2005) Major signaling pathways modulate Arabidopsis glucosinolate accumulation and response to both phloem-feeding and chewing insects. Plant Physiol 138:1149–1162

    Article  PubMed  CAS  Google Scholar 

  • Mewis I, Tokuhisa JG, Schultz JC et al (2006) Gene expression and glucosinolate accumulation in Arabidopsis thaliana in response to generalist and specialist herbivores of different feeding guilds and the role of defense signaling pathways. Phytochemistry 67:2450–2462

    Article  PubMed  CAS  Google Scholar 

  • Mikkelsen MD, Petersen BL, Glawischnig E et al (2003) Modulation of CYP79 genes and glucosinolate profiles in Arabidopsis by defense signaling pathways. Plant Physiol 131:298–308

    Article  PubMed  CAS  Google Scholar 

  • Mohn T, Cutting B, Ernst B, Hamburger M (2007) Extraction and analysis of intact glucosinolates—A validated pressurized liquid extraction/liquid chromatography–mass spectrometry protocol for Isatis tinctoria, and qualitative analysis of other cruciferous plants. J Chromatogr A 1166:142–151

    Article  PubMed  CAS  Google Scholar 

  • Müller, C (2008) Interactions between plants containing glucosinolates and myrosinases and the sawfly Athalia rosae. Phytochem Rev

  • Müller C, Agerbirk N, Olsen CE et al (2001) Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae. J Chem Ecol 27:2505–2516

    Article  PubMed  Google Scholar 

  • Müller C, Wittstock U (2005) Uptake and turn-over of glucosinolates sequestered in the sawfly Athalia rosae. Insect Biochem Mol Biol 35:1189–1198

    Article  PubMed  CAS  Google Scholar 

  • Nafisi M, Goregaoker S, Botanga CJ et al (2007) Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis. Plant Cell 19:2039–2052

    Article  PubMed  CAS  Google Scholar 

  • Pedras MSC, Nycholat CM, Montaut S et al (2002) Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Phytochemistry 59:611–625

    Article  PubMed  CAS  Google Scholar 

  • Pedras MSC, Okinyo POD (2008) Remarkable incorporation of the first sulfur containing indole derivative: another piece in the biosynthetic puzzle of crucifer phytoalexins. Org Biomol Chemistry 6:51–54

    Article  CAS  Google Scholar 

  • Pedras MSC, Zheng Q, Sarma-Mamillapalle VK (2007) The phytoalexins from Brassicaceae: structure, biological activity, synthesis and biosynthesis. Nat Prod Commun 2:319–330

    CAS  Google Scholar 

  • Petersen BL, Chen S, Hansen CH et al (2002) Composition and content of glucosinolates in developing Arabidopsis thaliana. Planta 214:562–571

    Article  PubMed  CAS  Google Scholar 

  • Piotrowski M, Schemenewitz A, Lopukhina A et al (2004) Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure. J Biol Chem 279:50717–50725

    Article  PubMed  CAS  Google Scholar 

  • Preobrazhenskaya MN, Bukhman VM, Korolev AM, Efimov SA (1993a) Ascorbigen and other indole-derived compounds from Brassica vegetables and their analogs as anticarcinogenic and immunomodulating agents. Pharmacol Ther 60:301–313

    Article  PubMed  CAS  Google Scholar 

  • Preobrazhenskaya MN, Korolev AM, Lazhko EI et al (1993b) Ascorbigen as a precursor of 5,11-dihydroindolo[3,2-b]carbazole. Food Chem 48:57–62

    Article  CAS  Google Scholar 

  • Reifenrath K, Riederer M, Müller C (2005) Leaf surface wax layers of Brassicaceae lack feeding stimulants for Phaedon cochleariae. Entomol Exp Appl 115:41–50

    Article  CAS  Google Scholar 

  • Renwick JAA, Radke CD, Sachdev-Gupta K, Städler E (1992) Leaf surface chemicals stimulating oviposition by Pieris rapae (Lepidoptera: Pieridae) on cabbage. Chemoecology 3:33–38

    Article  CAS  Google Scholar 

  • Roessingh P, Städler E, Baur R et al (1997) Tarsal chemoreceptors and oviposition behavior of the cabbage root fly (Delia radicum) sensitive to fractions and new compounds of host leaf surface extracts. Physiol Entomol 22:140–148

    Article  CAS  Google Scholar 

  • Rostás M, Bennett R, Hilker M (2002) Comparative physiological responses in Chinese cabbage induced by herbivory and fungal infection. J Chem Ecol 28:2449–2463

    Article  PubMed  Google Scholar 

  • Rothschild M, Schoonhoven LM (1977) Assessment of egg load by Pieris brassicae (Lepidoptera: Pieridae). Nature 266:352–355

    Article  Google Scholar 

  • Safe S (2001) Molecular biology of the Ah receptor and its role in carcinogenesis. Toxic Lett 120:1–7

    Article  CAS  Google Scholar 

  • Sasagawa C, Matsushima T (1991) Mutagen formation on nitrite treatment of indole compounds derived from indole-glucosinolate. Mutat Res 250:169–174

    PubMed  CAS  Google Scholar 

  • Schraudolf H, Bauerle R (1986) N-acetyl-3-indolylmethylglucosinolate in seedlings of Tovaria pendula Ruiz et Pav. Z Naturforsch 41c:526–528

    Google Scholar 

  • Shapiro TA, Fahey JW, Wade KL et al (1998) Human metabolism and excretion of cancer chemoprotective glucosinolates and isothiocyanates of cruciferous vegetables. Cancer Epidemiol Biomarkers Prev 7:1091–1100

    PubMed  CAS  Google Scholar 

  • Slominski BA, Campbell LD (1989) Formation of indole glucosinolate breakdown products in autolyzed steamed and cooked Brassica vegetables. J Agric Food Chem 37:1297–1302

    Article  CAS  Google Scholar 

  • Städler E, Reifenrath K (2008) Glucosinolates on the leaf surface perceived by insect herbivores: review of ambiguous results and new investigations. Phytochem Rev

  • Städler E, Renwick JAA, Radke CD, Sachdev-Gupta K (1995) Tarsal contact chemoreceptor response to glucosinolates and cardenolides mediating oviposition in Pieris rapae. Physiol Entomol 20:175

    Article  Google Scholar 

  • Staub RE, Feng C, Onisko B et al (2002) Fate of indole-3-carbinol in cultured human breast tumor cells. Chem Res Toxicol 15:101–109

    Article  PubMed  CAS  Google Scholar 

  • Stephensen PU, Bonnesen C, Bjeldanes LF, Vang O (1999) Modulation of cytochrome P4501A1 activity by ascorbigen in murine hepatoma cells. Biochem Pharmacol 58:1145–1153

    Article  CAS  Google Scholar 

  • Stephensen PU, Bonnesen C, Schaldach C et al (2000) N-Methoxyindole-3-carbinol is a more efficient inducer of cytochrome P-450 1A1 in cultured cells than indole-3-carbinol. Nutr Cancer 36:112–121

    Article  PubMed  CAS  Google Scholar 

  • Tabor MW, Shertzer HG, Myers BL (1988) In vitro metabolism of the dietary chemopreventive agent indole-3-carbinol. FASEB J 2(5):abstract 4881

    Google Scholar 

  • Textor S, Gershenzon J (2008) Glucosinolate induction by herbivores. Phytochem Rev

  • Tiedink HG, Davies JA, Visser NA et al (1989) The stability of the nitrosated products of indole, indole-3-acetonitrile, indole-3-carbinol and 4-chloroindole. Food Chem Toxicol 27:723–730

    Article  PubMed  CAS  Google Scholar 

  • Travers-Martin N, Müller C (2007) Specificity of induction responses in Sinapis alba and their effects on a specialist herbivore. J Chem Ecol 33:1582–1597

    Article  PubMed  CAS  Google Scholar 

  • Traw MB (2002) Is induction response negatively correlated with constitutive resistance in black mustard? Evolution 56:2196–2205

    PubMed  Google Scholar 

  • Truscott RJW, Johnstone PK, Minchinton IR, Sang JP (1983) Indole glucosinolates in Swede (Brassica napobrassica L. Mill). J Agric Food Chem 31:863–867

    Article  CAS  Google Scholar 

  • van Dam NM, Witjes L, Svatos A (2004) Interactions between aboveground and belowground induction of glucosinolates in two wild Brassica species. New Phytol 161:801–810

    Article  Google Scholar 

  • van Loon JJA, Blaakmeer A, Griepink FC et al (1992) Leaf surface compound from Brassica oleracea (Cruciferae) induces oviposition by Pieris brassicae (Lepidoptera: Pieridae). Chemoecology 3:39–44

    Article  Google Scholar 

  • Vanderpas J (2006) Nutritional epidemiology and thyroid hormone metabolism. Annu Rev Nutr 26:293–322

    Article  PubMed  CAS  Google Scholar 

  • Vierheilig H, Bennett R, Kiddle G et al (2000) Differences in glucosinolate patterns and arbuscular mycorrhizal status of glucosinolate-containing plant species. New Phytol 146:343–352

    Article  CAS  Google Scholar 

  • Vorwerk S, Biernacki S, Hillebrand H et al (2001) Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster. Planta 212:508–516

    Article  PubMed  CAS  Google Scholar 

  • Wakabayashi K, Nagao M, Ochiai M et al (1985) A mutagen precursor in Chinese cabbage, indole-3-acetonitrile, which becomes mutagenic on nitrite treatment. Mutat Res 143:17–21

    Article  PubMed  CAS  Google Scholar 

  • Wattenberg LW (1971) Studies of polycyclic hydrocarbon hydroxylases of the intestine possibly related to cancer. Cancer 28:99–102

    Article  PubMed  CAS  Google Scholar 

  • Windsor AJ, Reichelt M, Figuth A et al (2005) Geographic and evolutionary diversification of glucosinolates among near relatives of Arabidopsis thaliana (Brassicaceae). Phytochemistry 66:1321–1333

    Article  PubMed  CAS  Google Scholar 

  • Wittstock U, Agerbirk N, Stauber EJ et al (2004) Successful herbivore attack due to metabolic diversion of a plant chemical defense. Proc Natl Acad Sci USA 101:4859–4864

    Article  PubMed  CAS  Google Scholar 

  • Zhao Y, Hull AK, Gupta NR et al (2002) Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3. Genes Dev 16:3100–3112

    Article  PubMed  CAS  Google Scholar 

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Author notes

  1. Jae Hak Kim

    Present address: Monsanto Company, St. Louis, MO, USA

Authors and Affiliations

  1. Faculty of Life Science, University of Copenhagen, 1871, Frederiksberg C, Denmark

    Niels Agerbirk

  2. Boyce Thompson Institute for Plant Research, 1 Tower Road, Ithaca, NY, 14853, USA

    Martin De Vos, Jae Hak Kim & Georg Jander

Authors
  1. Niels Agerbirk
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  2. Martin De Vos
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  3. Jae Hak Kim
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  4. Georg Jander
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Correspondence to Georg Jander.

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Agerbirk, N., De Vos, M., Kim, J.H. et al. Indole glucosinolate breakdown and its biological effects. Phytochem Rev 8, 101–120 (2009). https://doi.org/10.1007/s11101-008-9098-0

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  • DOI: https://doi.org/10.1007/s11101-008-9098-0

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