Chapter five Glucosinolate hydrolysis and its impact on generalist and specialist insect herbivores

Recent Advances in Phytochemistry

Volumn 37, Issue C, 2003, Pages 101-125

  Wittstock, Ute ^a   Kliebenstein, Daniel J ^a   Lambrix, Virginia ^a   Reichelt, Michael ^a   Gershenzon, Jonathan ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957765891     PISSN: 00799920     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0079-9920(03)80020-5     Document Type: Article

References (81)

1. Chew F.S. Biological effects of glucosinolates. In: Cutler H.G. (Ed). Biologically Active Natural Products (1988), American Chemical Society, Washington DC 155-181
2. Louda S., and Mole S. Glucosinolates: Chemistry and ecology. In: Rosenthal G.A., and Berenbaum M.R. (Eds). Herbivores: Their Interaction with Secondary Plant Metabolites (Vol. 1 The Chemical Participants) (1991), Academic Press, Inc., San Diego 123-164
3. Rask L., Andreasson E., Ekbom B., Eriksson S., Pontoppidan B., and Meijer J. Myrosinase: gene family evolution and herbivore defense in Brassicaceae. Plant Mol. Biol. 42 (2000) 93-113
4. Li Q., Eigenbrode S.D., Stringam G.R., and Thiagarajah M.R. Feeding and growth of Plutella xylostella and Spodoptera eridania on Brassica juncea with varying glucosinolate concentrations and myrosinase activities. J. Chem. Ecol. 26 (2000) 2401-2419
5. Chew F.S., and Renwick J.A.A. Host plant choice in Pieris butterflies. In: Carde R.T., and Bell W.J. (Eds). Chemical Ecology of Insects Vol. 2 (1995), Chapman & Hall, New York 214-238
6. Nielsen J.K., Hansen M.L., Agerbirk N., Petersen B.L., and Halkier B.A. Responses of the flea beetles Phyllotreta nemorum and P. cruciferae to metabolically engineered Arabidopsis thaliana with an altered glucosinolate profile. Chemoecology 11 (2001) 75-83
7. Bradburne R.P., and Mithen R. Glucosinolate genetics and the attraction of the aphid parasitoid Diaeretiella rapae to Brassica. Proc. R. Soc. Lond. Ser. B-Biol. Sci. 267 (2000) 89-95
8. Bones A.M., and Rossiter J.T. The myrosinase-glucosinolate system, its organisation and biochemistry. Physiol. Plant. 97 (1996) 194-208
9. Brocker E.R., and Benn M.H. The intramolecular formation of epithioalkanenitriles from alkenylglucosinolates by Crambe abyssinica seed flour. Phytochemistry 22 (1983) 770-772
10. Tookey H.L. Crambe thioglucoside glucohydrolase (EC 3.2.3.1): Separation of a protein required for epithiobutane formation. Can. J. Biochem. 51 (1973) 1654-1660
11. Petroski R.J., and Tookey H.L. Interactions of thioglucoside glucohydrolase and epithiospecifier protein of cruciferous plants to form 1-cyanoepithioalkanes. Phytochemistry 21 (1982) 1903-1905
12. Macleod A.J., and Rossiter J.T. The occurence and activity of epithiospecifier protein in some Cruciferae seeds. Phytochemistry 24 (1985) 1895-1898
13. Gmelin R., and Virtanen A.I. A new type of enzymatic cleavage of mustard oil glucosides. Formation of allylthiocyanate in Thlaspi arvense L. and benzylthiocyanate in Lepidium ruderale L. and Lepidium sativum L. Acta Chem. Scand. 13 (1959) 1474-1475
14. Cole R. Isothiocyanates, nitriles and thiocyanates as products of autolysis of glucosinolates in Cruciferae. Phytochemistry 15 (1976) 759-762
15. Chevolleau S., Gasc N., Rollin P., and Tulliez J. Enzymatic, chemical, and thermal breakdown of H-3-labeled glucobrassicin, the parent indole glucosinolate. J. Agric. Food Chem. 45 (1997) 4290-4296
16. Agerbirk N., Olsen C.E., and Sørensen H. Initial and final products, nitriles, and ascorbigens produced in myrosinase-catalyzed hydrolysis of indole glucosinolates. J. Agric. Food Chem. 46 (1998) 1563-1571
17. Attieh J., Sparace S.A., and Saini H.S. Purification and properties of multiple isoforms of a novel thiol methyltransferase involved in the production of volatile sulfur compounds from Brassica oleracea. Arch. Biochem. Biophys. 380 (2000) 257-266
18. Attieh J., Djiana R., Koonjul P., Etienne C., Sparace S.A., and Saini H.S. Cloning and functional expression of two plant thiol methyltransferases: A new class of enzymes involved in the biosynthesis of sulfur volatiles. Plant Mol. Biol. 50 (2002) 511-521
19. Stoewsand G.S. Bioactive organosulfur phytochemicals in Brassica oleracea vegetables-a review. Food Chem. Toxicol. 33 (1995) 537-543
20. Buskov S., Serra B., Rosa E., Sørensen H., and Sørensen J.C. Effects of intact glucosinolates and products produced from glucosinolates in myrosinase-catalyzed hydrolysis on the potato cyst nematode (Globodera rostochiensis cv. Woll). J. Agric. Food Chem. 50 (2002) 690-695
21. Lichtenstein E.P., Strong F.M., and Morgan D.G. Identification of 2-phenylethylisothiocyanate as an insecticide occuring naturally in the edible part of turnips. J. Agric. Food Chem. 10 (1962) 30-33
22. Zhang Y., Talalay P., Cho C.-G., and Posner G.H. A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc. Natl. Acad. Sci. USA 89 (1992) 2399-2403
23. Vaughn S.F., and Berhow M.A. 1-Cyano-2-hydroxy-3-butene, a phytotoxin from crambe (Crambe abyssinica) seedmeal. J. Chem. Ecol. 24 (1998) 1117-1126
24. Tierens K., Thomma B.P.H., Brouwer M., Schmidt J., Kistner K., Porzel A., Mauch-Mani B., Cammue B.P.A., and Broekaert W.F. Study of. Plant Physiol. 125 (2001) 1688-1699
25. Peterson C.J., Tsao R., and Coats J.R. Glucosinolate aglucones and analogues: Insecticidal properties and a QSAR. Pest. Sci. 54 (1998) 35-42
26. Kawakishi S., and Kaneko T. Interaction of oxidized glutathione with allyl isothiocyanate. Phytochemistry 24 (1985) 715-718
27. Kawakishi S., and Kaneko T. Interaction of proteins with allyl isothiocyanate. J. Agric. Food Chem. 35 (1987) 85-88
28. Ohkawa H., Ohkawa R., Yamamoto I., and Casida J.E. Enzymatic mechanisms and toxicological significance of hydrogen cyanide liberation from various organothiocyanates and organonitriles in mice and houseflies. Pest. Biochem. Physiol. 2 (1972) 95-112
29. Wadleigh R.W., and Yu S.J. Metabolism of organothiocyanate allelochemicals by glutathione transferase in three lepidopterous insects. J. Econ. Entomol. 81 (1988) 776-780
30. Wallig M.A., Gould D.H., and Fettman M.J. Comparative toxicities of the naturally occuring nitrile 1-cyano-3,4-epithiobutane and the synthetic nitrile n-valeronitrile in rats: differences in target organs, metabolism and toxic mechanisms. Fd. Chem. Toxic. 26 (1988) 149-157
31. Peterson C.J., Cosse A., and Coats J.R. Insecticidal components in the meal of Crambe abyssinica. J. Agric. Urb. Entomol. 17 (2000) 27-35
32. Bartlet E., Blight M.M., Hick A.J., and Williams I.H. The responses of the cabbage seed weevil (Ceutorhynchus assimilis) to the odour of oilseed rape (Brassica napus) and to some volatile isothiocyanates. Entomol. Exp. Appl. 68 (1993) 295-302
33. Evans K.A., and Allen-Williams L.J. Response of cabbage seed weevil (Ceutorhynchus assimilis) to baits of extracted and synthetic host-plant odor. J. Chem. Ecol. 24 (1998) 2101-2114
34. Blight M.M., Pickett J.A., Wadhams L.J., and Woodcock C.M. Antennal responses of Ceutorhynchus assimilis and Psylliodes chrysocephala to volatiles from oilseed rape. Ann. Appl. Biol. 23 (1989) 329-334
35. Blight M.M., Pickett J.A., Wadhams L.J., and Woodcock C.M. Antennal perception of oilseed rape, Brassica napus (Brassicaceae), volatiles by the cabbage seed weevil Ceutorhynchus assimilis (Coleoptera, Curculionidae). J. Chem. Ecol. 21 (1995) 1649-1664
36. Staedler E. Chemoreceptions of host plant chemicals by ovipositing females of Delia (Hylemya) brassicae. Entomol. Exp. Appl. 24 (1978) 511-520
37. Nielsen J.K. Host plant discrimination within Cruciferae: Feeding responses of four leaf beetles (Coleoptera: Chrysomelidae) to glucosinolates, cucurbitacins and cardenolides. Entomol. Exp. Appl. 24 (1978) 41-54
38. Geervliet J.B.F., Vet L.E.M., and Dicke M. Volatiles from damaged plants as major cues in long-range host-searching by the specialist parasitoid Cotesia rubecula. Entomol. Exp. Appl. 73 (1994) 289-297
39. Geervliet J.B.F., Posthumus M.A., Vet L.E.M., and Dicke M. Comparative analysis of headspace volatiles from different caterpillar-infested or uninfested food plants of Pieris species. J. Chem. Ecol. 23 (1997) 2935-2954
40. Van Poecke R.M., Posthumus M.A., and Dicke M. Herbivore-induced volatile production by Arabidopsis thaliana leads to attraction of the parasitoid Cotesia rubecula: Chemical, behavioural, and gene-expression analysis. J. Chem. Ecol. 27 (2001) 1911-1928
41. Mattiacci L., and Dicke M. The parasitoid Cotesia glomerata (Hymenoptera: Braconidae) discriminates between first and fifth larval instars of its host Pieris brassicae, on the basis of contact cues from frass, silk, and herbivore-damaged leaf tissue. J. Insect Behav. 8 (1995) 485-498
42. Wittstock U., and Halkier B.A. Glucosinolate research in the Arabidopsis era. Trends in Plant Sci. 7 (2002) 263-270
43. Kliebenstein D.J., Kroymann J., Brown P., Figuth A., Pedersen D., Gershenzon J., and Mitchell-Olds T. Genetic control of natural variation in Arabidopsis glucosinolate accumulation. Plant Physiol. 126 (2001) 811-825
44. Lambrix V., Reichelt M., Mitchell-Olds T., Kliebenstein D.J., and Gershenzon J. The Arabidopsis epithiospecifier protein promotes the hydrolysis of glucosinolates to nitriles and influences Trichoplusia ni herbivory. Plant Cell 13 (2001) 2793-2807
45. Lister C., and Dean C. Recombinant inbred lines for mapping RFLP and phenotypic markers in Arabidopsis thaliana. Plant J. 4 (1993) 745-750
46. Bernardi R., Negri A., Ronchi S., and Palmieri S. Isolation of the epithiospecifier protein from oil-rape (Brassica napus ssp oleifera) seed and its characterization. FEBS Lett. 467 (2000) 296-298
47. Kliebenstein D., Pedersen D., Barker B., and Mitchell-olds T. Comparative analysis of quantitative trait loci controlling glucosinolates, myrosinase and insect resistance in Arabidopsis thaliana. Genetics 161 (2002) 325-332
48. Jander G., Cui J.P., Nhan B., Pierce N.E., and Ausubel F.M. The TASTY locus on chromosome 1 of Arabidopsis affects feeding of the insect herbivore Trichoplusia ni. Plant Physiol. 126 (2001) 890-898
49. Wadleigh R.W., and Yu S.J. Detoxification of isothiocyanate allelochemicals by glutathione transferase in three lepidopterous species. J. Chem. Ecol. 14 (1988) 1279-1288
50. Francis F., Haubruge E., Gaspar C., and Dierickx P.J. Glutathione S-transferases of Aulacorthum solani and Acyrthosiphon pisum: Partial purification and characterization. Comp. Biochem. Physiol. B-Biochem. Mol. Biol. 129 (2001) 165-171
51. Yu S.J. Microsomal oxidation of allelochemicals in generalist (Spodoptera frugiperda) and semispecialist (Anticarsia gemmatalis) insects. J. Chem. Ecol. 13 (1987) 423-436
52. Ratzka A., Vogel H., Kliebenstein D., Mitchell-Olds T., and Kroymann J. Disarming the mustard oil bomb. Proc. Natl. Acad. Sci. USA 99 (2002) 11223-11228
53. Müller C., Agerbirk N., Olsen C.E., Boeve J.L., Schaffner U., and Brakefield P.M. Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae. J. Chem. Ecol. 27 (2001) 2505-2516
54. Aliabadi A., Renwick J.A.A., and Whitman D.W. Sequestration of glucosinolates by harlequin bug Murgantia histrionica. J. Chem. Ecol. 28 (2002) 1749-1762
55. Bridges M., Jones A.M.E., Bones A.M., Hodgson C., Cole R., Bartlet E., Wallsgrove R., Karapapa V.K., Watts N., and Rossiter J.T. Spatial organization of the glucosinolate-myrosinase system in Brassica specialist aphids is similar to that of the host plant. Proc. R. Soc. Lond. Ser. B-Biol. Sci 269 (2002) 187-191
56. Kliebenstein D.J., Lambrix V.M., Reichelt M., Gershenzon J., and Mitchell-Ols T. Gene duplication in the diversification of secondary, metabolism: Tandem 2-oxoglutarate-dependent dioxygenases control glucosinolate biosynthesis in Arabidopsis. Plant Cell 13 (2001) 681-693
57. Seo S.T., and Tang C.S. Hawaiian fruit flies (Diptera: Tephritidae): toxicity of benzyl isothiocyanate against eggs or 1st instars of three species. J. Econ. Entomol. 75 (1982) 1132-1135
58. Bartelt R.J., and Mikolajczak K.L. Toxicity of compounds derived from Limnanthes alba seed to fall armyworm (Lepidoptera: Noctuidae) and European corn borer (Lepidoptera: Pyralidae) larvae. J. Econ. Entomol. 82 (1989) 1054-1060
59. El Sayed G., Louveaux A., Mavratzotis M., Rollin P., and Quinsac A. Effects of glucobrassicin, epiprogoitrin and related breakdown products on locusts feeding: Schouwia purpurea and desert locust relationships. Entomol. Exp. Appl. 78 (1996) 231-236
60. Borek V., Elberson L.R., Mccaffrey J.P., and Morra M.J. Toxicity of isothiocyanates produced by glucosinolates in Brassicaceae species to black vine weevil eggs. J. Agric. Food Chem. 46 (1998) 5318-5323
61. Görnitz K. Weitere Untersuchungen über Insekten-Attraktivstoffe aus Cruciferen. Nachrichtenbl. Dt. Pflanzensch. 10 (1956) 137-147
62. Schnitzler W.H., and Müller H.P. Über die Lockwirkung eines Senföls (Allylisothiocyanat) auf die Grosse Kohlfliege. Phorbia floralis., Zeitschr. angew. Entom. 63 (1969) 1-8
63. Nair K.S.S., and Mcewen F.L. Host selection by the adult cabbage maggot, Hylemya brassicae, (Diptera: Anthomyiidae): Effect of glucosinolates and common nutrients on oviposition. Can. Entomol. 108 (1976) 1021-1030
64. Finch S. Volatile plant chemicals and their effect on host plant finding by the cabbage, root fly. Entomol. Exp. Appl. 24 (1978) 150-159
65. Finch S., and Skinner G. Trapping cabbage root flies in traps baited with plant extracts and with natural and synthetic isothiocyanates. Entomol. Exp. Appl. 31 (1982) 133-139
66. Smart L.E., and Blight M.M. Field discrimination of oilseed rape, Brassica nap0us, volatiles by cabbage seed weevil, Ceutorhynchus assimilis. J. Chem. Ecol. 23 (1997) 2555-2567
67. Bartlet E., Blight M.M., Lane P., and Williams I.H. The responses of the cabbage seed weevil Ceutorhynchus assimilis to volatile compounds from oilseed rape in a linear track olfactometer. Entomol. Exp. Appl. 85 (1997) 257-262
68. Pivnick K.A., Lamb R.J., and Reed D. Response of flea beetles, Phyllotreta spp., to mustard oils and nitriles in field trapping experiments. J. Chem. Ecol. 18 (1992) 863-873
69. Feeny P., Paauwe K.L., and Demong N.J. Flea beetles and mustard oils: Host plant specificity of Phyllotreta cruciferae and P. striolata adults (Coleoptera: Chrysomelidae). Ann Entomol. Soc. Am. 63 (1970) 832-841
70. Toitayavan M., and Altieri M.A. Synomone-mediated interactions between the parasitoid Diaeretiella rapae and Brevicoryne brassicae under field conditions. Entomophaga 35 (1990) 499-507
71. Pivnick K.A. Response of Meteorus leviventris, (Hymenoptera: Braconidae) to mustard oils in field trapping experiments. J. Chem. Ecol. 19 (1993) 2075-2079
72. Murchie A.K., Smart L.E., and Williams I.H. Responses of Dasineura, brassicae and its parasitoids Platygaster subuliformis and Omphale clypealis to field traps baited with organic isothiocyanates. J. Chem. Ecol. 23 (1997) 917-927
73. Greenhalgh R., and Mitchell N.D. The involvement of flavour volatiles in the resistance to downy mildew of wild and cultivated forms of Brassica oleracea. New Phytol. 77 (1976) 391-398
74. Mithen R.F., and Lewis B.G. In vitro activity of glucosinolates and their products against Leptosphaeria maculans. Trans. Br. Mycol. Soc. 87 (1986) 433-440
75. Brader G., Tas E., and Palva E.T. Jasmonate-dependent induction of indole glucosinolates in Arabidopsis by culture filtrates of the nonspecific pathogen Erwinia caratovora. Plant Physiol. 126 (2001) 849-860
76. Bending G.D., and Lincoln S.D. Inhibition of soil nitrifying bacteria communities and their activities by glucosinolate hydrolysis products. Soil Biol. Biochem. 32 (2000) 1261-1269
77. Donkin S.G., Eiteman M.A., and Williams P.L. Toxicity of glucosinolates and their enzymatic decomposition products to Caenorhabditis elegans. J. Nematol. 27 (1995) 258-262
78. Galletti S., Bernardi R., Leoni O., Rollin P., and Palmieri S. Preparation and biological activity of four epiprogoitrin myrosinase-derived products. J. Agric. Food Chem. 49 (2001) 471-476
79. Nastruzzi C., Cortesi R., Esposito E., Menegatti E., Leoni O., Iori R., and Palmieri S. In vitro antiproliferative activity of isothiocyanates and nitriles generated by myrosinase-mediated hydrolysis of glucosinolates from seeds of cruciferous vegetables. J. Agric. Food Chem. 48 (2000) 3572-3575
80. Matusheski N.V., and Jeffery E.H. Comparison of the bioactivity of two glucoraphanin hydrolysis products found in broccoli, sulforaphane and sulforaphane nitrile. J. Agric. Food Chem. 49 (2001) 5743-5749
81. Basten G.P., Bao Y.P., and Williamson G. Sulforaphane and its glutathione conjugate but not sulforaphane nitrile induce UDP-glucuronosyl transferase (UGT1A1) and glutathione transferase (GSTA1) in cultured cells. Carcinogenesis 23 (2002) 1399-1404