Journal of Plant Growth Regulation

, Volume 23, Issue 3, pp 179–199 | Cite as

Biosynthesis and Metabolism of Jasmonates

  • Florian Schaller
  • Andreas SchallerEmail author
  • Annick Stintzi


Jasmonates are derived from oxygenated fatty acids via the octadecanoid pathway and characterized by a pentacyclic ring structure. They have regulatory function as signaling molecules in plant development and adaptation to environmental stress. Until recently, it was the cyclopentanone jasmonic acid (JA) that attracted most attention as a plant growth regulator. It becomes increasingly clear, however, that biological activity is not limited to JA but extends to, and may even differ between its many metabolites and conjugates as well as its cyclopentenone precursors. The enzymes of jasmonate biosynthesis and metabolism may thus have a regulatory function in controlling the activity and relative levels of different signaling molecules. Such a function is supported by both the characterization of loss of function mutants in Arabidopsis, and the biochemical characterization of the enzymes themselves.


Jasmonates Octadecanoid pathway Oxylipins Plant defense Plant development Plant hormones Signaling 


  1. Abramovitz, AS, Massey, V 1976Interaction of phenols with old yellow enzyme - Physical evidence for charge-transfer complexesJ Biol Chem25153275336Google Scholar
  2. Agrawal, GK, Jwa, NS, Shibato, J, Han, O, Iwahashi, H, Rakwal, R 2003Diverse environmental cues transiently regulate OsOPR1 of the “octadecanoid pathway” revealing its importance in rice defense/stress and developmentBiochem Biophys Res Commun31010731082Google Scholar
  3. Agrawal, GK, Tamogami, S, Han, O, Iwahashi, H, Rakwal, R 2004Rice octadecanoid pathwayBiochem Biophys Res Commun317115Google Scholar
  4. Almeras, E, Stolz, S, Vollenweider, S, Reymond, P, Mene-Saffrane, L, Farmer, EE 2003Reactive electrophile species activate defense gene expression in ArabidopsisPlant J34205216Google Scholar
  5. Bachmann, A, Hause, B, Maucher, H, Garbe, E, Voros, K, Weichert, H, Wasternack, C, Feussner, I 2002Jasmonate-induced lipid peroxidation in barley leaves initiated by distinct 13-LOX forms of chloroplastsBiol Chem38316451657Google Scholar
  6. Baertschi, SW, Ingram, CD, Harris, TM, Brash, AR 1988Absolute configuration of cis-12-oxophytodienoic acid of flaxseed: implications for the mechanism of biosynthesis from the 13(S)-hydroperoxide of linolenic acidBiochemistry271824Google Scholar
  7. Bartel, B, LeClere, S, Magidin, M, Zolman, BK 2001Inputs to the active indole-3-acetic acid pool: De novo synthesis, conjugate hydrolysis, and indole-3-butyric acid β-oxidationJournal of Plant Growth Regulation20198216Google Scholar
  8. Behrends, W, Engeland, K, Kindl, H 1988Characterization of two forms of the multifunctional protein acting in fatty acid beta-oxidationArch Biochem Biophys263161169Google Scholar
  9. Beisson, F, Koo, AJ, Ruuska, S, Schwender, J, Pollard, M, Thelen, JJ, Paddock, T, Salas, JJ, Savage, L, Milcamps, A, Mhaske, VB, Cho, Y, Ohlrogge, JB 2003Arabidopsis genes involved in acyl lipid metabolism. A 2003 census of the candidates, a study of the distribution of expressed sequence tags in organs, and a web-based databasePlant Physiol132681697Google Scholar
  10. Bell, E, Mullet, JE 1993Characterization of an Arabidopsis lipoxygenase gene responsive to methyl jasmonate and woundingPlant Physiol1031131137Google Scholar
  11. Bell, E, Creelman, RA, Mullet, JE 1995A chloroplast lipoxygenase is required for wound-induced jasmonic acid accumulation in ArabidopsisProc Natl Acad Sci USA9286758679Google Scholar
  12. Berger, S, Bell, E, Mullet, JE 1996Two methyl jasmonate-insensitive mutants show altered expression of AtVsp in response to methyl jasmonate and woundingPlant Physiol111525531Google Scholar
  13. Biesgen, C, Weiler, EW 1999Structure and regulation of OPR1 and OPR2, two closely related genes encoding 12-oxophytodienoic acid-10,11-reductases from Arabidopsis thalianaPlanta208155165CrossRefPubMedGoogle Scholar
  14. Birkett, MA, Campbell, CA, Chamberlain, K, Guerrieri, E, Hick, AJ, Martin, JL, Matthes, M, Napier, JA, Pettersson, J, Pickett, JA, Poppy, GM, Pow, EM, Pye, BJ, Smart, LE, Wadhams, GH, Wadhams, LJ, Woodcock, CM 2000New roles for cis-jasmone as an insect semiochemical and in plant defenseProc Natl Acad Sci USA9793299334Google Scholar
  15. Blechert, S, Brodschelm, W, Hölder, S, Kammerer, L, Kutchan, TM, Mueller, MJ, Xia, ZQ, Zenk, MH 1995The octadecanoic pathway: signal molecules for the regulation of secondary pathwaysProc Natl Acad Sci USA9240994105Google Scholar
  16. Blechert, S, Bockelmann, C, Brümmer, O, Füβlein, M, Gundlach, H, Haider, G, Hölder, S, Kutchan, TM, Weiler, EW, Zenk, MH 1997Structural separation of biological activities of jasmonates and related compoundsJ Chem Soc Perkin Trans135493560Google Scholar
  17. Blechert, S, Bockelmann, C, Füβlein, M, Schrader, T, Stelmach, B, Niesel, U, Weiler, EW 1999Structure-activity analyses reveal the existence of two separate groups of active octadecanoids in elicitation of the tendril-coiling response of Bryonia dioica JacqPlanta207470479Google Scholar
  18. Blee, E 1998Phytooxylipins and plant defense reactionsProg Lipid Res373372Google Scholar
  19. Blee, E 2002Impact of phyto-oxylipins in plant defenseTrends Plant Sci7315322Google Scholar
  20. Block, MA, Dome, AJ, Joyard, J, Douce, R 1983Preparation and characterization of membrane fractions enriched in outer and inner envelope membranes from spinach chloroplasts. II. Biochemical characterizationJ Biol Chem2581328113286Google Scholar
  21. Brash, AR 1999Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrateJ Biol Chem2742367923682CrossRefGoogle Scholar
  22. Breithaupt, C, Strassner, J, Breitinger, U, Huber, R, Macheroux, P, Schaller, A, Clausen, T 2001X-ray structure of 12-oxophytodienoate reductase 1 provides structural insight into substrate binding and specificity within the family of OYEStructure9419429Google Scholar
  23. Chandra, S, Heinstein, PF, Low, PS 1996Activation of phospholipase A by plant defense elicitorsPlant Physiol110979986Google Scholar
  24. Conconi, A, Miquel, M, Browse, JA, Ryan, CA 1996aIntracellular levels of free linolenic and linoleic acids increase in tomato leaves in response to woundingPlant Physiol111797803Google Scholar
  25. Conconi, A, Smerdon, MJ, Howe, GA, Ryan, CA 1996bThe octadecanoid signalling pathway in plants mediates a response to ultraviolet radiationNature383826829Google Scholar
  26. Costa, CL, Arruda, P, Benedetti, CE 2000An Arabidopsis gene induced by wounding functionally homologous to flavoprotein oxidoreductasesPlant Mol Biol446171Google Scholar
  27. Creelman, RA, Mullet, JE 1997Biosynthesis and action of jasmonates in plantsAnnu Rev Plant Physiol Plant Mol Biol48355381CrossRefPubMedGoogle Scholar
  28. Crombie, L, Morgan, DO 1988Formation of acylic α- and γ-ketols and 12-oxophytodienoic acid from linolenic acid 13-hydroperoxide by a flax enzyme preparation. Evidence for a single enzyme leading to a common allene epoxide intermediateJ Chem Soc PerkinTrans558560Google Scholar
  29. Dathe, W, Ronsch, H, Preiss, A, Schade, W, Sembdner, G, Schreiber, K 1981Endogenous plant hormones of the broad bean, Vicia faba L. (-)-Jasmonic acid, a plant growth inhibitor in pericarpPlanta153530535Google Scholar
  30. Deighton, N, Muckenschnabel, II, Goodman, BA, Williamson, B 1999Lipid peroxidation and the oxidative burst associated with infection of Capsicum annuum by Botrytis cinereaPlant J20485492Google Scholar
  31. Demole, E, Lederer, E, Mercier, D 1962Isolement et determination de la structure du jasmonate de methyle, constituant odorant characteristique de l’essence de jasminHelv Chim Acta45675685Google Scholar
  32. Dhondt, S, Geoffroy, P, Stelmach, BA, Legrand, M, Heitz, T 2000Soluble phospholipase A2 activity is induced before oxylipin accumulation in tobacco mosaic virus-infected tobacco leaves and is contributed by patatin-like enzymesPlant J23431440Google Scholar
  33. Eastmond, PJ, Hooks, MA, Williams, D, Lange, P, Bechtold, N, Sarrobert, C, Nussaume, L, Graham, IA 2000Promoter trapping of a novel medium-chain acyl-CoA oxidase, which is induced transcriptionally during Arabidopsis seed germinationJ Biol Chem2753437534381Google Scholar
  34. Falkenstein, E, Groth, B, Mithöfer, A, Weiler, EW 1991Methyljasmonate and linolenic acid are potent inducers of tendril coilingPlanta185316322Google Scholar
  35. Farmer, EE, Ryan, CA 1990Interplant Communication: Airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leavesProc Natl Acad Sci USA8777137716PubMedGoogle Scholar
  36. Farmer, EE, Johnson, RR, Ryan, CA 1991Regulation of expression of proteinase inhibitor genes by methyl jasmonate and jasmonic acidPlant Physiol989951002Google Scholar
  37. Farmer, EE, Ryan, CA 1992Octadecanoid-derived signals in plantsTrends Cell Biol2236241Google Scholar
  38. Feussner, I, Wasternack, C, Kindl, H, Kühn, H 1995Lipoxygenase-catalyzed oxygenation of storage lipids is implicated in lipid mobilization during germinationProc Natl Acad Sci USA921184911853Google Scholar
  39. Feussner, I, Kühn, H, Wasternack, C 1997Do specific linoleate 13-lipoxygenases initiate β-oxidation?FEBS Lett40615Google Scholar
  40. Feussner, I, Kühn, H, Wasternack, C 2001Lipoxygenase-dependent degradation of storage lipidsTrends Plant Sci6268273CrossRefPubMedGoogle Scholar
  41. Feussner, I, Wasternack, C 2002The lipoxygenase pathwayAnnu Rev Plant Biol53275297Google Scholar
  42. Feys, BJF, Benedetti, CE, Penfold, CN, Turner, JG 1994Arabidopsis mutants selected for resistance to the phytotoxin coronatine are male sterile, insensitive to methyl jasmonate, and resistant to a bacterial pathogenPlant Cell6751759CrossRefPubMedGoogle Scholar
  43. Fox, KM, Karplus, PA 1994Old yellow enzyme at 2 A resolution: overall structure, ligand binding, and comparison with related flavoproteinsStructure210891105Google Scholar
  44. Froehlich, JE, Itoh, A, Howe, GA 2001Tomato allene oxide synthase and fatty acid hydroperoxide lyase, two cytochrome P450 s involved in oxylipin metabolism, are targeted to different membranes of chloroplast envelopePlant Physiol125306317Google Scholar
  45. Fulda, M, Schnurr, J, Abbadi, A, Heinz, E, Browse, J 2004Peroxisomal Acyl-CoA synthetase activity is essential for seedling development in Arabidopsis thalianaPlant. Cell16394405Google Scholar
  46. Gerhardt, B 1983Localization of β-oxidation enzymes in peroxisomes isolated from nonfatty plant tissuesPlanta159238246Google Scholar
  47. Germain, V, Rylott, EL, Larson, TR, Sherson, SM, Bechtold, N, Carde, J-P, Bryce, JH, Graham, IA, Smith, SM 2001Requirement for 3-ketoacyl-CoA thiolase-2 in peroxisome development, fatty acid β-oxidation and breakdown of triacylglycerol in lipid bodies of Arabisopsis seedlingsPlant J28112Google Scholar
  48. Gidda, SK, Miersch, O, Levitin, A, Schmidt, J, Wasternack, C, Varin, L 2003Biochemical and molecular characterization of a hydroxyjasmonate sulfotransferase from Arabidopsis thalianaJ Biol Chem2781789517900Google Scholar
  49. Göbel, C, Feussner, I, Schmidt, A, Scheel, D, Sanchez-Serrano, J, Hamberg, M, Rosahl, S 2001Oxylipin profiling reveals the preferential stimulation of the 9-lipoxygenase pathway in elicitor-treated potato cellsJ Biol Chem27662676273Google Scholar
  50. Grechkin, AN, Fazilev, FN, Mukhtarova, LS 1995The lipoxygenase pathway in garlic (Allium sativun L.) bulbs: detection of the novel divinyl ether oxylipinsFEBS Lett371159162Google Scholar
  51. Grechkin, AN, Mukhtarova, LS, Hamberg, M 2000The lipoxygenase pathway in tulip (Tulipa gesneriand): detection of the ketol routeBiochem J352501509Google Scholar
  52. Gundlach, H, Muller, MJ, Kutchan, TM, Zenk, MH 1992Jasmonic acid as a signal transducer in elicitor-induced plant cell culturesProc Natl Acad Sci USA8923892393PubMedGoogle Scholar
  53. Gundlach, H, Zenk, MH 1998Biological activity and biosynthesis of pentacyclic oxylipins: The linoleic acid pathwayPhytochemistry47527537Google Scholar
  54. Haider, G, Schrader, T, Füβlein, M, Blechert, S, Kutchan, TM 2000Structure-activity relationships of synthetic analogs of jasmonic acid and coronatine on induction of benzo[c] phenanthridine alkaloid accumulation in Eschscholzia californica cell culturesBiol Chem381741748Google Scholar
  55. Halitschke, R, Baldwin, IT 2003Antisense LOX expression increases herbivore performance by decreasing defense responses and inhibiting growth-related transcriptional reorganization in Nicotiana attenuataPlant J36794807Google Scholar
  56. Hamberg, M, Hughes, MA 1988Fatty acid allene oxides. III. Albumin-induced cyclization of 12,13(5)-epoxy-9(Z), 11-octadecadienoic acidLipids23469475Google Scholar
  57. Hamberg, M, Fahlstadius, P 1990Allene oxide cyclase: a new enzyme in plant lipid metabolismArch Biochem Biophys276518526Google Scholar
  58. Hamberg, M 2000New cyclopentenone fatty acids formed from linoleic and linolenic acids in potatoLipids35353363Google Scholar
  59. Harms, K, Atzorn, R, Brash, A, Kühn, H, Wasternack, C, Willmitzer, L, Pena-Cortes, H 1995expression of a flax allene oxide synthase cDNA leads to increased endogenous jasmonic acid (JA) levels in transgenic potato plants but not to a corresponding activation of JA-responding genesPlant Cell716451654Google Scholar
  60. Harms, K, Ramirez, II, Pena-Cortez, H 1998Inhibition of wound-induced accumulation of allene oxide synthase transcripts in flax leaves by aspirin and salicylic acidPlant Physiol11810571065PubMedGoogle Scholar
  61. Hause, B, Stenzel, I, Miersch, O, Maucher, H, Kramell, R, Ziegler, J, Wasternack, C 2000Tissue-specific oxylipin signature of tomato flowers: allene oxide cyclase is highly expressed in distinct flower organs and vascular bundlesPlant J24113126PubMedGoogle Scholar
  62. Hause, B, Hause, G, Kutter, C, Miersch, O, Wasternack, C 2003aEnzymes of jasmonate biosynthesis occur in tomato sieve elementsPlant Cell Physiol44643648Google Scholar
  63. Hause, B, Stenzel, I, Miersch, O, Wasternack, C 2003bOccurrence of the allene oxide cyclase in different organs and tissues of Arabidopsis thalianaPhytochemistry64971980Google Scholar
  64. Hawkes V, Turner J (2004) “How are signalling pathways involving jasmonate and calcium linked to the wound response in Arabidopsis.” Abstract, International Conference on Arabidopsis Research, Berlin 11-14 July, 2004Google Scholar
  65. Hayashi, M, Toriyama, K, Kondo, M, Nishimura, M 19982,4-Dichlorophenoxybutyric acid-resistant mutants of Arabidopsis have defects in glyoxysomal fatty acid β-oxidationPlant Cell10183195CrossRefPubMedGoogle Scholar
  66. He, Y, Gan, S 2001Identical promoter elements are involved in regulation of the OPR1 gene by senescence and jasmonic acid in ArabidopsisPlant Mol Biol47595605Google Scholar
  67. He, Y, Fukushige, H, Hildebrand, DF, Gan, S 2002Evidence supporting a role of jasmonic acid in Arabidopsis leaf senescencePlant Physiol128876884Google Scholar
  68. Hisamatsu, Y, Goto, N, Hasegawa, K, Shigemori, H 2003Arabidopsides A and B, two new oxylipins from Arabidopsis thalianaTearhedron Lett4455535556Google Scholar
  69. Howe, GA, Lightner, J, Browse, J, Ryan, CA 1996An octadecanoid pathway mutant (JL5) of tomato is compromised in signaling for defense against insect attackPlant Cell820672077CrossRefPubMedGoogle Scholar
  70. Howe, GA, Lee, GI, Itoh, A, Li, L, DeRocher, AE 2000Cytochrome P450-dependent metabolism of oxylipins in tomato. Cloning and expression of allene oxide synthase and fatty acid hydroperoxide lyasePlant Physiol123711724PubMedGoogle Scholar
  71. Howe, GA, Schilmiller, AL 2002Oxylipin metabolism in response to stressCurr Opin Plant Biol5230236Google Scholar
  72. Ishiga, Y, Funato, A, Tachiki, T, Toyoda, K, Shiraishi, T, Yamada, T, Ichinose, Y 2002Expression of the 12-oxophytodienoic acid 10,11-reductase gene in the compatible interaction between pea and fungal pathogenPlant Cell Physiol4312101220Google Scholar
  73. Ishiguro, S, Kawai-Oda, A, Nishida, I, Okada, K 2001The defective in anther dehiscence1 gene encodes a novel phospholipase A1 catalyzing the initial step of jasmonic acid biosynthesis, which synchronizes pollen maturation, anther dehiscence, and flower opening in ArabidopsisPlant Cell1321912209CrossRefPubMedGoogle Scholar
  74. Ishikawa, A, Yoshihara, T, Nakamura, K 1994Jasmonate-inducible expression of a potato cathepsin D inhibitor-GUS gene fusion in tobacco cellsPlant Mol Biol26403414Google Scholar
  75. Itoh, A, Schilmiller, AL, McCaig, BC, Howe, GA 2002Identification of a jasmonate-regulated allene oxide synthase that metabolizes 9-hydroperoxides of linoleic and linolenic acidsJ Biol Chem2774605146058Google Scholar
  76. Iuchi, S, Yamaguchi-Shinozaki, K, Urao, T, Terao, T, Shinozaki, K 1996Novel drought-inducible genes in the highly drought-tolerant cowpea: cloning of cDNAs and analysis of the expression of the corresponding genesPlant Cell Physiol3710731082Google Scholar
  77. Jacinto, T, McGurl, B, Franceschi, V, Delano-Freier, J, Ryan, CA 1997Tomato prosystemin promoter confers wound-inducible, vascular bundle-specific expression of the β-glucuronidase gene in transgenic tomato plantsPlanta203406412Google Scholar
  78. Joyard, J, Block, MA, Douce, R 1991Molecular aspects of plastid envelope biochemistryEur J Biochem199489509Google Scholar
  79. Kelly, AA, Froehlich, JE, Dormann, P 2003Disruption of the two digalactosyldiacylglycerol synthase genes DGD1 and DGD2 in Arabidopsis reveals the existence of an additional enzyme of galactolipid synthesisPlant Cell1526942706Google Scholar
  80. Kessler, A, Halitschke, R, Baldwin, IT 2004Silencing the jasmonate cascade: induced plant defenses and insect populationsScience305665668PubMedGoogle Scholar
  81. Koch, T, Bandemer, K, Boland, W 1997Biosynthesis of cis-jasmone: A pathway for the inactivation and the disposal of the plant stress hormone jasmonic acid to the gas phase?Helvetica Chimica Acta80838850Google Scholar
  82. Koda, Y 1992The role of jasmonic acid and related compounds in the regulation of plant developmentInt Rev Cytol135155199Google Scholar
  83. Koda, Y, Kikuta, Y 1992Wound-induced accumulation of jasmonic acid in tissues of potato tubersPlant Cell Physiol35751756Google Scholar
  84. Koda, Y 1997Possible involvement of jasmonates in various morphogenic eventsPhysiologia Plantarum100639646Google Scholar
  85. Kolomiets, MV, Hannapel, DJ, Chen, H, Tymeson, M, Gladon, RJ 2001Lipoxygenase is involved in the control of potato tuber developmentPlant Cell13613626Google Scholar
  86. Kramell, R, Miersch, O, Hause, B, Ortel, B, Parthier, B, Wasternack, B 1997Amino acid conjugates of jasmonic acid induce jasmonate-responsive gene expression in barley (Hordeum vulgare L.) leavesFEBS Lett414197202Google Scholar
  87. Kramell, R, Miersch, O, Atzorn, R, Parthier, B, Wasternack, C 2000Octadecanoid-derived alteration of gene expression and the “oxylipin signature” in stressed barley leaves. Implications for different signaling pathwaysPlant Physiol123177188Google Scholar
  88. Kubigsteltig, I, Laudert, D, Weiler, EW 1999Structure and regulation of the Arabidopsis thaliana allene oxide synthase genePlanta208463471PubMedGoogle Scholar
  89. Kubigsteltig, II, Weiler, EW 2003Arabidopsis mutants affected in the transcriptional control of allene oxide synthase, the enzyme catalyzing the entrance step in octadecanoid biosynthesisPlanta217748757Google Scholar
  90. Laudert, D, Pfannschmidt, U, Lottspeich, F, Holländer-Czytko, H, Weiler, EW 1996Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP74), the first enzyme of the octadecanoid pathway to jasmonatesPlant Mol Biol31323335Google Scholar
  91. Laudert, D, Hennig, P, Stelmach, BA, Müller, A, Andert, L, Weiler, EW 1997Analysis of 12-oxo-phytodienoic acid enantiomers in biological samples by capillary gas chromatography-mass spectrometry using cyclodextrin stationary phasesAnal Biochem246211217Google Scholar
  92. Laudert, D, Weiler, EW 1998Allene oxide synthase: A major control point Arabidopsis thaliana octadecanoid signallingPlant J15675684Google Scholar
  93. Laudert, D, Schaller, F, Weiler, EW 2000Transgenic Nicotiana tabacum and Arabidopsis thaliana plants overexpressing allene oxide synthasePlanta211163165Google Scholar
  94. Li, C, Liu, G, Xu, C, Lee, GI, Bauer, P, Ling, HQ, Ganal, MW, Howe, GA 2003The tomato suppressor of prosystemin-mediated responses2 gene encodes a fatty acid desaturase required for the biosynthesis of jasmonic acid and the production of a systemic wound signal for defense gene expressionPlant Cell1516461661PubMedGoogle Scholar
  95. Li, L, Li, C, Lee, GI, Howe, GA 2002Distinct roles for jasmonate synthesis and action in the systemic wound response of tomatoProc Natl Acad Sci USA9964166421Google Scholar
  96. Li, L, Zhao, Y, McCaig, BC, Wingerd, BA, Wang, J, Whalon, ME, Pichersky, E, Howe, GA 2004The tomato homolog of CORONATINE-INSENSITIVE1 is required for the maternal control of seed maturation, jasmonate-signaled defense responses, and glandular trichome developmentPlant Cell16126143PubMedGoogle Scholar
  97. Lorenzo, O, Chico, JM, Sanchez-Serrano, JJ, Solano, R 2004JASMONATE-INSENSITIVE1 encodes a MYC transcription factor essential to discriminate between different jasmonate-regulated defense responses in ArabidopsisPlant Cell1619381950CrossRefGoogle Scholar
  98. Massey, V, Schopfer, LM, Dunham, WR (1984) “On the enigma of Old Yellow Enzyme’s spectral properties” In: Bray, RC, Engel, PC, Mayhew, SG (eds.), Flavins and Flavoproteins, Walter de Gruyter & Co, BerlinGoogle Scholar
  99. Massey, V, Schopfer, LM 1986Reactivity of old yellow enzyme with β-NADPH and other pyridine nucleotide derivativesJ Biol Chem26112151222Google Scholar
  100. Matsui, H, Nakamura, G, Ishiga, Y, Toshima, H, Inagaki, Y, Toyoda, K, Shiraishi, T, Ichinose, Y 2004Structure and expression of 12-oxophytodienoate reductase (subgroup I) genes in pea, and characterization of the oxidoreductase activities of their recombinant productsMol Genet Genomics271110Google Scholar
  101. Maucher, H, Hause, B, Feussner, I, Ziegler, J, Wasternack, C 2000Allene oxide synthases of barley (Hordeum vulgare cv. Salome): tissue specific regulation in seedling developmentPlant J21199213Google Scholar
  102. Maucher, H, Stenzel, I, Miersch, O, Stein, N, Prasad, M, Zierold, U, Schweizer, P, Dorer, C, Hause, B, Wasternack, C 2004The allene oxide cyclase of barley (Hordeum vulgare L.)-cloning and organ-specific expressionPhytochemistry65801811Google Scholar
  103. McConn, M, Browse, J 1996The critical requirement for linolenic acid is pollen development, not photosynthesis, in an Arabidopsis mutantPlant Cell8403416CrossRefPubMedGoogle Scholar
  104. McConn, M, Creelman, RA, Bell, E, Mullet, JE, Browse, J 1997Jasmonate is essential for insect defense in ArabidopsisProc Natl Acad Sci USA9454735477Google Scholar
  105. Melan, MA, Dong, X, Endara, ME, Davis, KR, Ausubel, FM, Peterman, TK 1993An Arabidopsis thaliana lipoxygenase gene can be induced by pathogens, abscisic acid, and methyl jasmonatePlant Physiol101441450Google Scholar
  106. Meyer, A, Miersch, O, Buttner, C, Dathe, W, Sembdner, G 1984Occurrence of the plant growth regulator jasmonic acid in plantsJ Plant Growth Regul318Google Scholar
  107. Miersch, O, Sembdner, G, Schreiber, K 1989Occurrence of jasmonic acid analogues in Vicia fabaPhytochemistry28339340Google Scholar
  108. Miersch, O, Kramell, R, Parthier, B, Wasternack, B 1999Structure-activity relations of substituted, deleted or stereospecifically altered jasmonic acid in gene expression of barley leavesPhytochemistry50353361Google Scholar
  109. Miersch, O, Weichert, H, Stenzel, I, Hause, B, Maucher, H, Feussner, I, Wasternack, C 2004Constitutive overexpression of allene oxide cyclase in tomato (Lycopersicon esculentum cv. Lukullus) elevates levels of some jasmonates and octadecanoids in flower organs but not in leavesPhytochemistry65847856Google Scholar
  110. Muckenschnabel, I, Williamson, B, Goodman, BA, Lyon, GD, Stewart, D, Deighton, N 2001Markers for oxidative stress associated with soft rots in French beans (Phaseolus vulgaris) infected by Botrytis cinereaPlanta212376381Google Scholar
  111. Mueller, MJ, Brodschelm, W, Spannagl, E, Zenk, MH 1993Signaling in the elicitation process is mediated through the octadecanoid pathway leading to jasmonic acidProc Natl Acad Sci USA9074907494Google Scholar
  112. Mueller, MJ 1997Enzymes involved in jasmonic acid biosynthesisPhysiol Plant100653663Google Scholar
  113. Müssig, C, Biesgen, C, Lisso, J, Uwer, U, Weiler, EW, Altmann, T 2000A novel stress-inducible 12-oxophytodienoate reductase from Arabidopsis thaliana provides a potential link between brassinosteroid-action and jasmonic-acid synthesisJ Plant Physiol157143152Google Scholar
  114. Narvaez-Vasquez, J, Florin-Christensen, J, Ryan, CA 1999Positional specificity of a phospholipase A2 activity induced by wounding, systemin, and oligosaccharide elicitors in tomato leavesPlant Cell1122492260Google Scholar
  115. Narvaez-Vasquez, J, Ryan, CA 2004The cellular localization of prosystemin: a functional role for phloem parenchyma in systemic wound signalingPlanta218360369PubMedGoogle Scholar
  116. O’Donnell, PJ, Calvert, C, Atzorn, R, Wasternack, C, Leyser, HMO, Bowles, DJ 1996Ethylene as a signal mediating the wound response of tomato plantsScience27419141917CrossRefPubMedGoogle Scholar
  117. Pan, Z, Durst, F, Werck-Reichhart, D, Gardner, HW, Camara, B, Cornish, K, Backhaus, RA 1995The major protein of guayule rubber particles is a cytochrome P450J Biol Chem7084878494Google Scholar
  118. Parchmann, S, Gundlach, H, Mueller, MJ 1997Induction of 12-oxo-phytodienoic acid in wounded plants and elicited plant cell culturesPlant Physiol11510571064Google Scholar
  119. Park, JH, Halitschke, R, Kim, HB, Baldwin, IT, Feldmann, KA, Feyereisen, R 2002A knock-out mutation in allene oxide synthase results in male sterility and defective wound signal transduction in Arabidopsis due to a block in jasmonic acid biosynthesisPlant J31112Google Scholar
  120. Parthier, B 1991Jasmonates, new regulators of plant growth and development: many facts and few hypotheses on their actionsBot Acta104446454Google Scholar
  121. Preisig-Müller, R, Gühnemann-Schäfer, K, Kindl, H 1994Domains of the tetrafunctional protein acting in glyoxysomal fatty acid β-oxidation. Demonstration of epimerase and isomerase activities on a peptide lacking hydratase activityJ Biol Chem2692047520481Google Scholar
  122. Rance, II, Fournier, J, Esquerre-Tugaye, MT 1998The incompatible interaction between Phytophthora parasitica var. nicotianae race 0 and tobacco is suppressed in transgenic plants expressing antisense lipoxygenase sequencesProc Natl Acad Sci USA9565546559Google Scholar
  123. Reymond, P, Farmer, EE 1998Jasmonate and salicylate as global signals for defense gene expressionCurr Opin Plant Biol1404411CrossRefPubMedGoogle Scholar
  124. Reymond, P, Weber, H, Damond, M, Farmer, EE 2000Differential gene expression in response to mechanical wounding and insect feeding in ArabidopsisPlant Cell12707719CrossRefPubMedGoogle Scholar
  125. Richmond, TA, Bleecker, AB 1999A defect in β-oxidation causes abnormal inflorescence development in ArabidopsisPlant Cell1119111924CrossRefPubMedGoogle Scholar
  126. Rowley, AF, Kuhn, H T.S 1998Eicosanoids and related compounds in plant and animalsPortland PressLondonGoogle Scholar
  127. Roy, S, Pouenat, ML, Caumont, C, Cariven, C, Prevost, MC, Esquerre-Tugaye, MT 1995Phospholipase-activity and phospholipid patterns in tobacco cells treated with fungal elicitorPlant Science1071725Google Scholar
  128. Royo, J, Leon, J, Vancanneyt, G, Albar, JP, Rosahl, S, Ortego, F, Castanera, P, Sanchez-Serrano, JJ 1999Antisense-mediated depletion of a potato lipoxygenase reduces wound induction of proteinase inhibitors and increases weight gain of insect pestsProc Natl Acad Sci USA9611461151CrossRefPubMedGoogle Scholar
  129. Ryan, CA, Moura, DS 2002Systemic wound signaling in plants: a new perceptionProc Natl Acad Sci USA9965196520PubMedGoogle Scholar
  130. Rylott, EL, Rogers, CA, Gilday, AD, Edgell, T, Larson, TR, Graham, IA 2003Arabidopsis mutants in short- and medium-chain acyl-CoA oxidase activities accumulate acyl-CoAs and reveal that fatty acid ?-oxidation is essential for embryo developmentJ Biol Chem2782137021377Google Scholar
  131. Sanders, PM, Lee, PY, Biesgen, C, Boone, JD, Beals, TP, Weiler, EW, Goldberg, RB 2000The Arabidopsis DELAYED DEHISCENCE1 gene encodes an enzyme in the jasmonic acid synthesis pathwayPlant Cell1210421061Google Scholar
  132. Schaller, F, Weiler, EW 1997aEnzymes of octadecanoid biosynthesis in plants. 12-oxo-phytodienoate 10,11-reductaseEur J Biochem245294299Google Scholar
  133. Schaller, F, Weiler, EW 1997bMolecular cloning and characterization of 12-oxophytodienoate reductase, an enzyme of the octadecanoid signaling pathway from Arabidopsis thaliana. Structural and functional relationship to yeast old yellow enzymeJ Biol Chem2722806628072Google Scholar
  134. Schaller, F, Hennig, P, Weiler, EW 199812-Oxophytodienoate-10,11-reductase: occurrence of two isoenzymes of different specificity against stereoisomers of 12-oxophytodienoic acidPlant Physiol11813451351Google Scholar
  135. Schaller, F, Biesgen, C, Mussig, C, Altmann, T, Weiler, EW 200012-Oxophytodienoate reductase 3 (OPR3) is the isoenzyme involved in jasmonate biosynthesisPlanta210979984CrossRefPubMedGoogle Scholar
  136. Schaller, F 2001Enzymes of the biosynthesis of octadecanoid-derived signalling moleculesJ Exp Bot521123Google Scholar
  137. Schnurr, J, Shockey, J, Browse, J 2004The acyl-CoA synthetase encoded by LACS2 is essential for normal cuticle development in ArabidopsisPlant Cell16629642Google Scholar
  138. Sembdner, G, Parthier, B 1993The biochemistry and the physiological and molecular actions of jasmonatesAnnu Rev Plant Physiol Plant Mol Biol44569589CrossRefGoogle Scholar
  139. Seo, HS, Song, JT, Cheong, J-J, Lee, J-H, Lee, Y-W, Hwang, I, Lee, JS, Choi, YD 2001Jasmonic acid carboxyl methyltransferase: A key enzyme for jasmonate-regulated plant responsesProc Natl Acad Sci U S A9847884793Google Scholar
  140. Shockey, JM, Fulda, MS, Browse, J 2003Arabidopsis contains a large superfamily of acyl-activating enzymes. Phylogenetic and biochemical analysis reveals a new class of acyl-coenzyme A synthetasesPlant Physiol13210651076Google Scholar
  141. Siedow, JN 1991Plant lipoxygenase: Structure and functionAnnu Rev Plant Physiol42145188Google Scholar
  142. Sivasankar, S, Sheldrick, B, Rothstein, SJ 2000Expression of allene oxide synthase determines defense gene activation in tomatoPlant Physiol12213351342PubMedGoogle Scholar
  143. Smyth, DR, Bowman, JL, Meyerowitz, EM 1990Early flower development in ArabidopsisPlant Cell2755767CrossRefPubMedGoogle Scholar
  144. Sobajima, H, Takeda, M, Sugimori, M, Kobashi, N, Kiribuchi, K, Cho, EM, Akimoto, C, Yamaguchi, T, Minami, E, Shibuya, N, Schaller, F, Weiler, EW, Yoshihara, T, Nishida, H, Nojiri, H, Omori, T, Nishiyama, M, Yamane, H 2003Cloning and characterization of a jasmonic acid-responsive gene encoding 12-oxophytodienoic acid reductase in suspension-cultured rice cellsPlanta216692698Google Scholar
  145. Somerville, C, Browse, J 1991plant lipids: metabolism, mutants, and membranesScience2528087Google Scholar
  146. Song, WC, Brash, AR 1991Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P-450Science253781784Google Scholar
  147. Song, WC, Funk, CD, Brash, AR 1993Molecular cloning of an allene oxide synthase: A cytochrome P450 specialized for the metabolism of fatty acid hydroperoxidesProc Natl Acad Sci U S A9085198523Google Scholar
  148. Staswick, PE, Su, W, Howell, SH 1992Methyl jasmonate inhibition of root growth and induction of a leaf protein are decreased in an Arabidopsis thaliana mutantProc Natl Acad Sci U S A8968376840Google Scholar
  149. Staswick, PE, Tiryaki, I, Rowe, ML 2002Jasmonate response locus JAR1 and several related Arabidopsis genes encode enzymes of the firefly luciferase superfamily that show activity on jasmonic, salicylic, and indole-3-acetic acids in an assay for adenylationPlant Cell1414051415CrossRefPubMedGoogle Scholar
  150. Staswick, PE, Tiryaki, I 2004The oxylipin signal jasmonic acid is activated by an enzyme that conjugates it to isoleucine in ArabidopsisPlant Cell1621172127PubMedGoogle Scholar
  151. Stelmach, BA, Muller, A, Hennig, P, Laudert, D, Andert, L, Weiler, EW 1998Quantitation of the octadecanoid 12-oxo-phytodienoic acid, a signalling compound in plant mechanotransductionPhytochemistry47539546Google Scholar
  152. Stelmach, BA, Muller, A, Hennig, P, Gebhardt, S, Schubert-Zsilavecz, M, Weiler, EW 2001A novel class of oxylipins, sn1-O-(12-oxophytodienoyl)-sn2-O-(hexadecatrienoyl)-monogalactosyl diglyceride, from Arabidopsis thalianaJ Biol Chem2761283212838Google Scholar
  153. Stenzel, I, Hause, B, Maucher, H, Pitzschke, A, Miersch, O, Ziegler, J, Ryan, CA, Wasternack, C 2003aAllene oxide cyclase dependence of the wound response and vascular bundle-specific generation of jasmonates in tomato-amplification in wound signallingPlant J3577589Google Scholar
  154. Stenzel, I, Hause, B, Miersch, O, Kurz, T, Maucher, H, Weichert, H, Ziegler, J, Feussner, I, Wasternack, C 2003bJasmonate biosynthesis and the allene oxide cyclase family of Arabidopsis thalianaPlant Mol Biol51895911Google Scholar
  155. Stintzi, A, Browse, J 2000The Arabidopsis male-sterile mutant, opr3, lacks the 12-oxophytodienoic acid reductase required for jasmonate synthesisProc Natl Acad Sci U S A971062510630Google Scholar
  156. Stintzi, A, Weber, H, Reymond, P, Browse, J, Farmer, EE 2001Plant defense in the absence of jasmonic acid: the role of cyclopentenonesProc Natl Acad Sci U S A981283712842Google Scholar
  157. Stott, K, Saito, K, Thiele, DJ, Massey, V 1993Old Yellow Enzyme. The discovery of multiple isozymes and a family of related proteinsJ Biol Chem26860976106Google Scholar
  158. Stra?ner, J, Furholz, A, Macheroux, P, Amrhein, N, Schaller, A 1999A homolog of old yellow enzyme in tomato. Spectral properties and substrate specificity of the recombinant proteinJ Biol Chem2743506735073Google Scholar
  159. Strassner, J, Schaller, F, Frick, UB, Howe, GA, Weiler, EW, Amrhein, NA, Macheroux, P, Schaller, A 2002Characterization and cDNA-microarray expression analysis of 12-oxophytodienoate reductases reveals differential roles for octadecanoid biosynthesis in the local versus the systemic wound responsePlant J32585601CrossRefPubMedGoogle Scholar
  160. Stuhlfelder, C, Mueller, MJ, Warzecha, H 2004Cloning and expression of a tomato cDNA encoding a methyl jasmonate cleaving esteraseEur J Biochem27129762983PubMedGoogle Scholar
  161. Stumpe, M, Kandzia, R, Gobel, C, Rosahl, S, Feussner, I 2001A pathogen-inducible divinyl ether synthase (CYP74D) from elicitor-treated potato suspension cellsFEBS Lett507371376Google Scholar
  162. Swiatek, A, Dongen, W, Esmans, EL, Onckelen, H 2004Metabolic fate of jasmonates in tobacco bright yellow-2 cellsPlant Physiol135161172PubMedGoogle Scholar
  163. Tilton, GB, Shockey, JM, Browse, J 2004Biochemical and molecular characterization of ACH2, an acyl-CoA thioesterase from Arabidopsis thaliana.J Biol Chem27974877494Google Scholar
  164. Ueda, J, Kato, J 1980Isolation and identification of a senescence-promoting substance from wormwood (Artemisia absinthium L.)Plant Physiol66246249Google Scholar
  165. Ueda, J, Kato, J, Yamane, H, Takahashi, N 1981Inhibitory effect of methyl jasmonate and related compounds on kinetin-induced retardation of oat leaf senescencePhysiol Plant52305309Google Scholar
  166. van der Stelt, M, Noordermeer, MA, Kiss, T, Van Zadelhoff, G, Merghart, B, Veldink, GA, Vliegenthart, JF 2000Formation of a new class of oxylipins from N-acyl (ethanol) amines by the lipoxygenase pathwayEur J Biochem26720002007Google Scholar
  167. Vance, RE, Hong, S, Gronert, K, Serhan, CN, Mekalanos, JJ 2004The opportunistic pathogen Pseudomonas aeruginosa carries a secretable arachidonate 15-lipoxygenaseProc Natl Acad Sci USA10121352139Google Scholar
  168. Vaz, AD, Chakraborty, S, Massey, V 1995Old Yellow enzyme: aromatization of cyclic enones and the mechanism of a novel dismutation reactionBiochemistry3442464256Google Scholar
  169. Veronesi, C, Rickauer, M, Fournier, J, Pouenat, ML, Esquerre-Tugaye, MT 1996Lipoxygenase gene expression in the tobacco-Phytophthora parasitica nicotianae interactionPlant Physiol1129971004Google Scholar
  170. Vick, BA, Zimmerman, DC 1979Distribution of a fatty acid cyclase enzyme system in plantsPlant Physiol64203205Google Scholar
  171. Vick, BA, Zimmerman, DC 1983The biosynthesis of jasmonic acid: a physiological role for plant lipoxygenaseBiochem Biophys Res Commun111470477Google Scholar
  172. Vick, BA, Zimmerman, DC 1984Biosynthesis of jasmonic acid by several plant speciesPlant Physiol75458461Google Scholar
  173. Vick, BA, Zimmerman, DC 1987Pathways of fatty acid hydroproxide metabolism in spinach leaf chloroplastsPlant Physiol8510731078Google Scholar
  174. Vollenweider, S, Weber, H, Stolz, S, Chetelat, A, Farmer, EE 2000Fatty acid ketodienes and fatty acid ketotrienes: Michael addition acceptors that accumulate in wounded and diseased Arabidopsis leavesPlant J24467476CrossRefPubMedGoogle Scholar
  175. von Dahl, CC, Baldwin, IT 2004Methyl jasmonate and cis-jasmone do not dispose of the herbivore-induced jasmonate burst in Nicotiana attenuataPhysiol Plant120474481PubMedGoogle Scholar
  176. von Malek, B, Graaff, E, Schneitz, K, Keller, B 2002The Arabidopsis male-sterile mutant dde2-2 is defective in the ALLENE OXIDE SYNTHASE gene encoding one of the key enzymes of the jasmonic acid biosynthesis pathwayPlanta216187192CrossRefPubMedGoogle Scholar
  177. Wallis, JG, Browse, J 2002Mutants of Arabidopsis reveal many roles for membrane lipidsProg Lipid Res41254278Google Scholar
  178. Wang, C, Avdiushko, S, Hildebrand, DF 1999Overexpression of a cytoplasm-localized allene oxide synthase promotes the wound-induced accumulation of jasmonic acid in transgenic tobaccoPlant Mol Biol40783793Google Scholar
  179. Wang, C, Zien, CA, Afitlhile, M, Welti, R, Hildebrand, DF, Wang, X 2000Involvement of phospholipase D in wound-induced accumulation of jasmonic acid in ArabidopsisPlant Cell1222372246Google Scholar
  180. Wang, X 2004Lipid signalingCurr Opin Plant Biol7329336Google Scholar
  181. Warburg, O, Christian, W 1932Ein zweites Sauerstoff-übertragendes Ferment und sein AbsorptionspektrumNaturwissenschaften20688Google Scholar
  182. Warburg, O, Christian, W 1933Über das gelbe Ferment und seine WirkungenBiochem Z266377411Google Scholar
  183. Wasternack, C, Hause, B 2002Jasmonates and octadecanoids: signals in plant stress. responses and developmentProg Nucl Acid Res Mol Biol72165221Google Scholar
  184. Weber, H, Vick, BA, Farmer, EE 1997Dinor-oxo-phytodienoic acid: a new hexadecanoid signal in the jasmonate familyProc Natl Acad Sci U S A941047310478Google Scholar
  185. Weber, H, Chetelat, A, Caldelari, D, Farmer, EE 1999Divinyl ether fatty acid synthesis in late blight-diseased potato leavesPlant Cell11485494Google Scholar
  186. Weichert, H, Stenzel, I, Berndt, E, Wasternack, C, Feussner, I 1999Metabolic profiling of oxylipins upon salicylate treatment in barley leaves-preferential induction of the reductase pathway by salicylateFEES Lett464133137Google Scholar
  187. Weiler, EW, Albrecht, T, Groth, B, Xia, Z-Q, Luxem, M, Liss, H, Andert, L, Spengler, P 1993Evidence for the involvement of jasmonates and their octadecanoid precursors in the tendril coiling response of Bryonia dioicaPhytochemistry32591600Google Scholar
  188. Weiler, EW, Kutchan, TM, Gorba, T, Brodschelm, W, Niesel, U, Bublitz, F 1994The Pseudomonas phytotoxin coronatine mimics octadecanoid signalling molecules of higher plantsFEBS Lett345913Google Scholar
  189. Weiler, EW, Laudert, D, Schaller, F, Stelmach, B, Hennig, P (1998) “Fatty acid-derived signaling molecules in the interaction of plants with their environment” In: Romeo, JT, Downum, KR, Verpoorte, R (eds.), Phytochemical signals and plant-microbe interactions. Recent advances in phytochemistry, Plenum Press, New York, pp 179–205Google Scholar
  190. Xie, D-X, Feys, BF, James, S, Nieto-Rostro, M, Turner, JG 1998COI1: an Arabidopsis gene required for jasmonate-regulated defense and fertilityScience28010911094CrossRefPubMedGoogle Scholar
  191. Yokoyama, M, Yamaguchi, S, Inomata, S, Komatsu, K, Yoshida, S, Ida, T, Yokokawa, Y, Yamaguchi, M, Kaihara, S, Takimoto, A 2000Stress-induced factor involved in flower formation of Lemna is an α-ketol derivative of linolenic acidPlant Cell Physiol4110113Google Scholar
  192. Yoshihara, T, Omer, E-SA, Koshino, H, Sakamura, S, Kikuta, Y, Koda, Y 1989Structure of a tuber-inducing stimulus from potato leaves (Solanum tuberosum L.)Agric Biol Chem328352837Google Scholar
  193. Zheng, Y, Massey, V, Schaller, A, Palfey, BA, Carey, PA 2001Comparison of resonance Raman spectra of flavin 3,4-dihydroxybenzoate charge-transfer complexes in three flavoenzymesJ Raman Spectrosc32579586Google Scholar
  194. Ziegler, J, Hamberg, M, Miersch, O, Parthier, B 1997Purification and characterization of allene oxide cyclase from dry corn seedsPlant Physiol114565573Google Scholar
  195. Ziegler, J, Wasternack, C, Hamberg, M 1999On the specificity of allene oxide cyclaseLipids3410051015Google Scholar
  196. Ziegler, J, Stenzel, I, Hause, B, Maucher, H, Hamberg, M, Grimm, R, Ganal, M, Wasternack, C 2000Molecular cloning of allene oxide cyclase. The enzyme establishing the stereochemistry of octadecanoids and jasmonatesJ Biol Chem2751913219138Google Scholar
  197. Zimmerman, DC, Feng, P 1978Characterization of a prostaglandin-like metabolite of linolenic acid produced by a flaxseed extractLipids13313316Google Scholar
  198. Zolman, BK, Yoder, A, Bartel, B 2000Genetic analysis of indole-3-butyric acid responses Arabidopsis thaliana reveals four mutant classesGenetics15613231337PubMedGoogle Scholar
  199. Zolman, BK, Monroe-Augustus, M, Thompson, B, Hawes, JW, Krukenberg, KA, Matsuda, SP, Bartel, B 2001achy1, an Arabidopsis mutant with impaired ?-oxidation, is defective in a peroxisomal ?-hydroxyisobutyryl-CoA hydrolaseJ Biol Chem2763103731046Google Scholar
  200. Zolman, BK, Silva, ID, Bartel, B 2001bThe Arabidopsis pxa1 mutant is defective in an ATP-binding cassette transporter-like protein required for peroxisomal fatty acid ?-oxidationPlant Physiol12712661278Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • Florian Schaller
    • 1
  • Andreas Schaller
    • 2
    Email author
  • Annick Stintzi
    • 2
  1. 1.Ruhr-Universität BochumLehrstuhl fur PflanzenphysiologieBochumGermany
  2. 2.Universität HohenheimInstitut fur Physiologie und Biotechnologie der Pflanzen (260)StuttgartGermany

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