Log in

Occurrence and identification of jasmonic acid and its amino acid conjugates induced by osmotic stress in barley leaf tissue

  • Published:
Journal of Plant Growth Regulation Aims and scope Submit manuscript

Abstract

The effect of osmotically active substances on the alteration of endogenous jasmonates was studied in barley (Hordeum vulgare L. cv. Salome) leaf tissue. Leaf segments were subjected to solutions of d-sorbitol, d-mannitol, polyethylene glycol 6000, sodium chloride, or water as a control. Alterations of endogenous jasmonates were monitored qualitatively and quantitatively using immunoassays. The structures of jasmonates isolated were determined on the basis of authentic substances by capillary gas chromatography-mass spectrometry. The stereochemistry of the conjugates was confirmed by high performance liquid chromatography with diastereoisomeric references. In barley leaves, jasmonic acid and its amino acid conjugates, for example, with valine, leucine, and isoleucine, are naturally occurring jasmonates. In untreated leaf segments, only low levels of these native jasmonates were found. After treatment of the leaf tissues with sorbitol, mannitol, as well as with polyethylene glycol, an increase of both jasmonic acid and its conjugates could be observed, depending on the stress conditions used. In contrast, salt stress was without any stimulating effect on the levels of endogenous jasmonates. From barley leaf segments exposed to sorbitol (1m) for 24 h, jasmonic acid was identified as the major accumulating compound. Jasmonic acid-amino acid conjugates increased likewise upon stress treatment.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Abbreviations

JM:

methyl jasmonate

JA:

jasmonic acid

JIP(s):

jasmonate-induced protein(s)

PEG:

polyethylene glycol

RIA:

radioimmunoassay

ELISA:

enzyme-linked immunosorbent assay

HPLC:

high performance liquid chromatography

GC-MS:

gas chromatography-mass spectrometry

R t :

retention time

IAA:

indole-3-acetic acid

References

  • Albrecht T, Kehlen A, Stahl K, Knöfel HD, Sembdner G, Weiler EW (1993) Quantification of rapid, transient increases in jasmonic acid in wounded plants using a monoclonal antibody. Planta 191:86–94

    Article  CAS  Google Scholar 

  • Anderson JM, Spilatro SR, Klauer SF, Franceschi VR (1989) Jasmonic acid-dependent increase in the level of vegetative storage proteins in soybean. Plant Sci 62:45–52

    Article  CAS  Google Scholar 

  • Bandurski RS, Schulze A, Domagalski W (1987) Synthesis and metabolism of conjugates of indole-3-acetic acid. In: Schreiber K, Schütte HR, Sembdner G (eds) Conjugated plant hormones: Structure, metabolism and function. Deutscher Verlag der Wissenschaften, Berlin, pp 11–20

    Google Scholar 

  • Bohlmann F, Wegner P, Jakupovic J, King RM (1984) Structure and synthesis of N-(acetoxy-)jasmonoyl phenylalanine methyl ester from Praxelis clematidea. Tetrahedron 40:2537–2540

    Article  CAS  Google Scholar 

  • Brückner C, Kramell R, Schneider G, Knöfel H-D, Sembdner G, Schreiber K (1986) N-[(-)-Jasmonoyl]-S-tyrosine: A conjugate of jasmonic acid from Vicia faba. Phytochemistry 25:2236–2237

    Article  Google Scholar 

  • Bruckner C, Kramell R, Schneider G, Schmidt J, Preiss A, Sembdner G, Schreiber K (1988) N-[(-)-Jasmonoyl]-S-tryptophan and a related tryptophan conjugate from Vicia faba. Phytochemistry 27:275–276

    Article  Google Scholar 

  • Cohen JD (1982) Identification and quantitative analysis of indole-3-acetyl-l-aspartate from seeds of Glycine max L. Plant Physiol 70:749–753

    PubMed  CAS  Google Scholar 

  • Cohen JD, Slovin JP, Bialek K (1987) Biochemical and molecular studies of native auxin conjugates. In: Schreiber K, Schütte HR, Sembdner G (eds) Conjugated plant hormones: Structure, metabolism and function. Deutscher Verlag der Wissenschaften, Berlin, pp 54–60

    Google Scholar 

  • Cross BE, Webster GRB (1970) New metabolites of Gibberella fujikuroi. XV. N-Jasmonoyl- and N-dihydrojasmonoyl-isoleucine. J Chem Soc 1839–1842

  • Dathe W, Rönsch H, Preiss A, Schade W, Sembdner G, Schreiber K (1981) Endogenous plant hormones of the broad bean Vicia faba L. (-)-Jasmonic acid, a plant growth inhibitor in pericarp. Planta 153:530–535

    Article  CAS  Google Scholar 

  • Epstein E, Baldi BG, Cohen JD (1986) Identification of indole-3-acetyl glutamate from seeds of Glycine max L. Plant Physiol 80:256–258

    PubMed  CAS  Google Scholar 

  • Farmer EE, Johnson RR, Ryan CA (1992) Regulation of expression of proteinase inhibitor genes by methyl jasmonate and jasmonic acid. Plant Physiol 98:995–1002

    PubMed  CAS  Google Scholar 

  • Gräbner R, Schneider G, Sembdner G (1976) Fraktionierung von Gibberellinen, Gibberellinkonjugaten und anderen Phytohormonen durch DEAE-Sephadex-Chromatographie. J Chromatogr 121:110–115

    Article  PubMed  Google Scholar 

  • Gundlach H, Müller MJ, Kutchan TM, Zenk MH (1992) Jasmonic acid is a signal transducer in elicitor-induced plant. Proc Natl Acad Sci USA 89:2389–2393

    Article  PubMed  CAS  Google Scholar 

  • Herrmann G, Kramell H-M, Kramell R, Weidhase RA, Sembdner G (1987) Biological activity of jasmonic acid conjugates. In: Schreiber K, Schütte HR, Sembdner G (eds) Conjugated plant hormones: Structure, metabolism and function. Deutscher Verlag der Wissenschaften, Berlin, 315–322

    Google Scholar 

  • Herrmann G, Lehmann J, Peterson A, Sembdner G, Weidhase RA, Parthier B (1989) Species and tissue specificity of jasmonate-induced abundant proteins. J Plant Physiol 134:703–709

    CAS  Google Scholar 

  • Knöfel HD, Brückner C, Kramell R, Sembdner G, Schreiber K (1990) Radioimmunoassay for the natural plant growth growth regulator (-)-jasmonic acid. Biochem Physiol Pflanzen 186:387–394

    Google Scholar 

  • Koda Y, Kikuta Y, Tazaki H, Tsu**o Y, Sakamura S, Yoshihara T (1991) Potato tuber-inducing activities of jasmonic acid and related compounds. Phytochemistry 30:1435–1438

    Article  CAS  Google Scholar 

  • Kramell R, Schmidt J, Schneider G, Sembdner G, Schreiber K (1988) Synthesis of N-(jasmonoyl)amino acid conjugates. Tetrahedron 44:5791–5801

    Article  CAS  Google Scholar 

  • Lehmann J, Herrmann G, Weidhase RA, Parthier B (1990) Induction of specific polypeptides in response to leaf senescence by methyl jasmonate, a putative plant growth regulator. In: Kutacek M, Elliot MC, Machackova I (eds) Molecular aspects of hormonal regulation of plant development. Proceedings of Symposium 39 and Colloquia 30 and 31 of the 14th Biochemical Congress held in Prague, Czechoslovakia 1988, pp 241–246

  • Lehmann J, Atzorn R, Brückner C, Reinbothe S, Leopold J, Wasternack C, Parthier B (1994) Specific expression of endogenous jasmonate, jasmonate- and ABA-inducible transcripts and proteins in osmotically stressed barley leaf segments. Planta, submitted

  • Mason HS, DeWald DB, Creelman RA, Mullet JE (1992) Coregulation of soybean vegetative storage protein gene expression by methyl jasmonate and soluble sugars. Plant Physiol 98:859–867

    PubMed  CAS  Google Scholar 

  • Meyer A, Schmidt J, Gross D, Jensen E, Rudolph A, Vorkefeld S, Sembdner G (1991) Amino acid conjugates as metabolites of the plant growth regulator dihydrojasmonic acid in barley (Hordeum vulgare). J Plant Growth Regul 10:17–25

    Article  CAS  Google Scholar 

  • Miersch O, Preiss A, Sembdner G, Schreiber K (1987) (+)-7-iso-Jasmonic acid and related compounds from Botryodiplodia theobromae. Phytochemistry 26:1037–1039

    Article  CAS  Google Scholar 

  • Money NP (1989) Osmotic pressure of aqueous polyethylene glycols: Relationship between molecular weight and vapor pressure deficit. Plant Physiol 91:766–769

    PubMed  CAS  Google Scholar 

  • Müller-Uri F, Parthier B, Nover L (1988) Jasmonate-induced alteration of gene expression in barley leaf segments analyzed by in vivo and in vitro protein synthesis. Planta 176:241–247

    Article  Google Scholar 

  • Parthier B, Brückner C, Dathe W, Hause B, Herrmann G, Knöfel HD, Kramell HM, Kramell R, Lehmann J, Miersch O, Reinbothe S, Sembdner G, Wasternack C, zur Nieden U (1992) Jasmonates: Metabolism, biological activities, and modes of action in senescence and stress responses. In: Karssen CM, Van Loon LC, Vreugdenhil D (eds) Progress in plant growth regulation 1991. Kluwer Academic Publishers, Dordrecht, pp 276–285

    Google Scholar 

  • Schmidt J, Kramell R, Brückner C, Schneider G, Sembdner G, Schreiber K, Stach J, Jensen E (1990) Gas chromatographic/mass spectrometric and tandem mass spectrometric investigations of synthetic amino acid conjugates of jasmonic acid and endogenously occurring related compounds from Vicia faba L. Biomed Environ Mass Spectrum 19:327–338

    Article  CAS  Google Scholar 

  • Schneider G, Kramell R, Bruckner C (1989) Separation of diastereomeric amino acid conjugates of jasmonic acid. J Chromatogr 483:459–462

    Article  CAS  Google Scholar 

  • Sembdner G, Parthier B (1993) The biochemistry and the physiological and molecular actions of jasmonates. Annu Rev Plant Physiol 44:569–589

    Article  CAS  Google Scholar 

  • Sembdner G, Meyer A, Miersch O, Brückner C (1990) Metabolism of jasmonic acid. In: Pharis RP, Rood SB (eds) Plant growth substances 1988. Springer Verlag, Berlin, pp 374–379

    Google Scholar 

  • Sembdner G, Atzorn R, Schneider G (1994) Plant hormone conjugation. In: Palme K (ed) Molecular Signal Transduction Pathways in Plants. Kluwer Academic Publishers, Dordrecht, submitted

    Google Scholar 

  • Staswick PE, Huang JF, Rhee Y (1991) Nitrogen and methyl jasmonate induction of soybean vegetative storage protein genes. Plant Physiol 96:130–136

    Article  PubMed  CAS  Google Scholar 

  • Ueda J, Kato J (1980) Isolation and identification of a senescence-promoting substance from wormwood (Artemisia absinthium L.). Plant Physiol 66:246–249

    PubMed  CAS  Google Scholar 

  • Vick BA, Zimmerman DC (1983) The biosynthesis of jasmonic acid: A physiological role for plant lipoxygenase. Biochem Biophys Res Commun 111:470–477

    Article  PubMed  CAS  Google Scholar 

  • Weidhase RA, Kramell HM, Lehmann J, Liebisch HW, Lerbs W, Parthier B (1987) Methyl jasmonate-induced changes in the polypeptide pattern of senescing barley leaf segments. Plant Sci 51:177–186

    Article  CAS  Google Scholar 

  • Weiler EW (1986) Plant hormone immunoassays based on monoclonal and polyclonal antibodies. In: Linsken HF, Jackson JF (eds) Immunoassays in plant sciences: Modern methods of plant analysis. New series, vol 4. Springer Verlag, Berlin, pp 1–17

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kramell, R., Atzorn, R., Schneider, G. et al. Occurrence and identification of jasmonic acid and its amino acid conjugates induced by osmotic stress in barley leaf tissue. J Plant Growth Regul 14, 29–36 (1995). https://doi.org/10.1007/BF00212643

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00212643

Keywords

Navigation