Herbivore-induced phenylacetonitrile is biosynthesized from de novo-synthesized l-phenylalanine in the giant knotweed, Fallopia sachalinensis

FEBS Letters

Volumn 587, Issue 12, 2013, Pages 1811-1817

  Noge, Koji ^a   Tamogami, Shigeru ^a  

^a AKITA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Fallopia sachalinensis; Methyl jasmonate; Phenylacetonitrile; Phenylalanine; Plant herbivore interaction; Popillia japonica

Indexed keywords

BENZYL CYANIDE DERIVATIVE; JASMONIC ACID METHYL ESTER; NITRILE; PHENYLALANINE;

AMINO ACID SYNTHESIS; ARTICLE; BEETLE; BIOSYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; FALLOPIA; FALLOPIA SACHALINENSIS; NONHUMAN; PLANT INSECT INTERACTION; PLANT LEAF; PLANT PARAMETERS; POPILLIA JAPONICA; PRIORITY JOURNAL;

ACETATES; ACETONITRILES; ANIMALS; BEETLES; CYCLOPENTANES; HERBIVORY; OXYLIPINS; PHENYLALANINE; PLANT LEAVES; POLYGONACEAE;

COLEOPTERA; FALLOPIA SACHALINENSIS; HEXAPODA; POPILLIA JAPONICA;

EID: 84878805593     PISSN: 00145793     EISSN: 18733468     Source Type: Journal    
DOI: 10.1016/j.febslet.2013.04.038     Document Type: Article

References (50)

1. T.C.J. Turlings, J.H. Tumlinson, and W.J. Lewis Exploitation of herbivore-induced plant odors by host-seeking parasitic wasps Science 250 1990 1251 1253
2. R.A. Dixon, and N.L. Paiva Stress-induced phenylpropanoid metabolism Plant Cell 7 1995 1085 1097
3. J. Kuć Phytoalexins, stress metabolism, and disease resistance in plants Annu. Rev. Phytopathol. 33 1995 275 297
4. H.T. Alborn, T.C.J. Turlings, T.H. Jones, G. Stenhagen, J.H. Loughrin, and J.H. Tumlinson An elicitor of plant volatiles from beet armyworm oral secretion Science 276 1997 945 949
5. A. Schmidt, D. Scheel, and D. Strack Elicitor-stimulated biosynthesis of hydroxycinnamoyltyramines in cell suspension cultures of Solanum tuberosum Planta 205 1998 51 55
6. P.W. Paré, M.A. Farag, V. Krishnamachari, H. Zhang, C.-M. Ryu, and J.W. Kloepper Elicitors and priming agents initiate plant defense responses Photosynth. Res. 85 2005 149 159
7. H. Dittrich, T.M. Kutchan, and M.H. Zenk The jasmonate precursor, 12-oxo-phytodienoic acid, induces phytoalexin synthesis in Petroselinum crispum cell cultures FEBS Lett. 309 1992 33 36
8. H. Gundlach, M.J. Muller, T.M. Kutchan, and M.H. Zenk Jasmonic acid is a signal transducer in elicitor-induced plant cell cultures Proc. Natl. Acad. Sci. USA 89 1992 2389 2393
9. K.J. Doughty, G.A. Kiddle, B.J. Pye, R.M. Wallsgrove, and J.A. Pickett Selective induction of glucosinolates in oilseed rape leaves by methyl jasmonate Phytochemistry 38 1995 347 350
10. I. Baldwin Inducible nicotine production in native Nicotiana as an example of adaptive phenotypic plasticity J. Chem. Ecol. 25 1999 3 30
11. A. Ishihara, Y. Ogura, S. Tebayashi, and H. Iwamura Jasmonate-induced changes in flavonoid metabolism in barley (Hordeum vulgare) leaves Biosci. Biotechnol. Biochem. 66 2002 2176 2182
12. G.A. Howe Jasmonates as signals in the wound response J. Plant Growth Regul. 23 2004 223 237
13. S. Tamogami, Y. Takahashi, M. Abe, K. Noge, R. Rakwal, and G.K. Agrawal Conversion of airborne nerolidol to DMNT emission requires additional signals in Achyranthes bidentata FEBS Lett. 585 2011 1807 1813
14. G. Sembdner, and B. Parthier The biochemistry and the physiological and molecular actions of jasmonates Annu. Rev. Plant Physiol. Plant Mol. Biol. 44 1993 569 589
15. R.A. Creelman, and J.E. Mullet Biosynthesis and action of jasmonates in plants Annu. Rev. Plant Physiol. Plant Mol. Biol. 48 1997 355 381
16. J.G. Turner, C. Ellis, and A. Devoto The jasmonate signaling pathway Plant Cell 14 2002 S153 S164
17. R. Halitschke, and I.T. Baldwin Jasmonates and related compounds in plant-insect interactions J. Plant Growth Regul. 23 2004 238 245
18. C. Wasternack Jasmonates: an update on biosynthesis, signal transduction and action in plant stress response, growth and development Ann. Bot. (Lond.) 100 2007 681 697
19. A. Ishihara, Y. Ohtsu, and H. Iwamura Biosynthesis of oat avenanthramide phytoalexins Phytochemistry 50 1999 237 242
20. H. Chen, A.D. Jones, and G.A. Howe Constitutive activation of the jasmonate signaling pathway enhances the production of secondary metabolites in tomato FEBS Lett. 580 2006 2540 2546
21. V. Tzin, and G. Galili New insights into the shikimate and aromatic amino acids biosynthesis pathways in plants Mol. Plant 3 2010 956 972
22. D.S. Seigler Plant Secondary Metabolism 1998 Kluwer Academic Publishers Dordrecht
23. K. Noge, M. Abe, and S. Tamogami Phenylacetonitrile from the giant knotweed, Fallopia sachalinensis, infested by the Japanese beetle, Popillia japonica, is induced by exogenous methyl jasmonate Molecules 16 2011 6481 6488
24. J. Takabayashi, and M. Dicke Plant-carnivore mutualism through herbivore-induced carnivore attractants Trends Plant Sci. 1 1996 109 113
25. J.H. Loughrin, D.A. Potter, and T.R. Hamilton-Kemp Volatile compounds induced by herbivory act as aggregation kairomones for the Japanese beetle (Popillia japonica Newman) J. Chem. Ecol. 21 1995 1457 1467
26. F. Brilli, P. Ciccioli, M. Frattoni, M. Prestininzi, A.F. Spanedda, and F. Loreto Constitutive and herbivore-induced monoterpenes emitted by Populus × euroamericana leaves are key volatiles that orient Chrysomela populi beetles Plant Cell Environ. 32 2009 542 552
27. B.A. Tapper, and G.W. Butler Oximes, nitriles and 2-hydroxynitriles as precursors in the biosynthesis of cyanogenic glucosides Biochem. J. 124 1971 935 941
28. R.A. Kahn, S. Bak, I. Svendsen, A.B. Halkier, and B.L. Møller Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum Plant Physiol. 115 1997 1661 1670
29. P.M. Dewick Cyanogenic glycosides Medicinal Natural Products-A Biosynthetic Approach Second ed. 2002 Wiley Chichester, UK 455 457
30. A.M. Bones, and J.T. Rossiter The enzymic and chemically induced decomposition of glucosinolates Phytochemistry 67 2006 1053 1067
31. E. Schönbrunn, S. Eschenburg, W.A. Shuttleworth, J.V. Schloss, N. Amrhein, J.N.S. Evans, and W. Kabsch Interaction of the herbicide glyphosate with its target enzyme 5-enolpyruvylshikimate 3-phosphate synthase in atomic detail Proc. Natl. Acad. Sci. USA 98 2001 1376 1380
32. SAS Institute Inc. (2003) JMP 5.1, Cary, NC.
33. B.M. Silva, S. Casal, P.B. Andrade, R.M. Seabra, M.B. Oliveira, and M.A. Ferreira Development and evaluation of a GC/FID method for the analysis of free amino acids in quince fruit and jam Anal. Sci. 19 2003 1285 1290
34. K. Fujii, Y. Ikai, H. Oka, M. Suzuki, and K. Harada A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: combination of Marfey's method with mass spectrometry and its practical application Anal. Chem. 69 1997 5146 5151
35. 11C in Nicotiana tabacum reveals insight into methyl jasmonate induced changes in metabolism J. Chem. Ecol. 36 2010 1058 1067
36. C.D. Broeckling, D.V. Huhman, M.A. Farag, J.T. Smith, G.D. May, P. Mendes, R.A. Dixon, and L.W. Sumner Metabolic profiling of Medicago truncatula cell cultures reveals the effects of biotic and abiotic elicitors on metabolism J. Exp. Bot. 56 2005 323 336
37. J. Görlach, H.-R. Raesecke, D. Rentsch, M. Regenass, P. Roy, M. Zala, C. Keel, T. Boller, N. Amrhein, and J. Schmid Temporally distinct accumulation of transcripts encoding enzymes of the prechorismate pathway in elicitor-treated, cultured tomato cells Proc. Natl. Acad. Sci. USA 92 1995 3166 3170
38. A. Kundu, N. Jawali, and A. Mitra Shikimate pathway modulates the elicitor-stimulated accumulation of fragrant 2-hydroxy-4-methoxybenzaldehyde in Hemidesmus indicus roots Plant Physiol. Biochem. 56 2012 104 108
39. K. Seidelmann, H. Weinert, and H.-J. Ferenz Wings and legs are production sites for the desert locust courtship-inhibition pheromone, phenylacetonitrile J. Insect Physiol. 49 2003 1125 1133
40. Y. Asano, and Y. Kato Z-Phenylacetaldoxime degradation by a novel aldoxime dehydratase from Bacillus sp. strain OxB-1 FEMS Microbiol. Lett. 158 1998 185 190
41. R.A. Kahn, T. Fahrendorf, B.A. Halkier, and B.L. Møller Substrate specificity of the cytochrome P450 enzymes CYP79A1 and CYP71E1 involved in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench Arch. Biochem. Biophys. 363 1999 9 18
42. U. Wittstock, and B.A. Halkier Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of l-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate J. Biol. Chem. 275 2000 14659 14666
43. L.T. Maslenkova, T.S. Miteva, and L.P. Popova Changes in the polypeptide patterns of barley seedlings exposed to jasmonic acid and salinity Plant Physiol. 98 1992 700 707
44. P.E. Staswick, W. Su, and S.H. Howell Methyl jasmonate inhibition of root growth and induction of a leaf protein are decreased in an Arabidopsis thaliana mutant Proc. Natl. Acad. Sci. USA 89 1992 6837 6840
45. T. Beardmore, S. Wetzel, and M. Kalous Interactions of airborne methyl jasmonate with vegetative storage protein gene and protein accumulation and biomass partitioning in Populus plants Can. J. For. Res. 30 2000 1106 1113
46. Y. Ogura, A. Ishihara, and H. Iwamura Induction of hydroxycinnamic acid amides and tryptophan by jasmonic acid, abscisic acid and osmotic stress in barley leaves Z. Naturforsch C. 56 2001 193 202
47. T.G. Köllner, C. Lenk, N. Zhao, I. Seidl-Adams, J. Gershenzon, F. Chen, and J. Degenhardt Herbivore-induced SABATH methyltransferases of maize that methylate anthranilic acid using S-adenosyl-l-methionine Plant Physiol. 153 2010 1795 1807
48. D.P.S. Verma, and C.-S. Zhang Regulation of proline and arginine biosynthesis in plants B.K. Singh, Plant Amino Acids 1999 Marcel Dekker, Inc. New York, NY 249 265
49. K. Urano, K. Maruyama, Y. Ogata, Y. Morishita, M. Takada, N. Sakurai, H. Suzuki, K. Saito, D. Shibata, M. Kobayashi, K. Yamaguchi-Shinozaki, and K. Shinozaki Characterization of the ABA-regulated global responses to dehydration in Arabidopsis by metabolomics Plant J. 57 2009 1065 1078
50. M. Erb, S. Meldau, and G.A. Howe Role of phytohormones in insect-specific plant reactions Trends Plant Sci. 17 2012 250 259