The Dinor Isoprostane Pathway in Plants

  • Christane Loeffler
  • Ingeborg Thoma
  • Markus Krischke
  • Martin J. Mueller
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 525)


Isoprostanes are products of free radical-catalyzed oxidation of arachidonic acid (20:4) in mammals [1], However, isoprostanoids can be formed virtually from any natural polyunsaturated fatty acid that contains at least three double bonds. a-Linolenic acid (18:3) fulfills that criterion, and thus, can be oxidized to a variety of C-18 isoprostane classes (dinor isoprostanes) [2]. Dinor isoprostanes in animals are either derived from β- oxidation of C20 isoprostanes or peroxidation of γ-linolenic acid (18:3) but not from α-linolenic acid which is only a trace fatty acid in mammals [3,4]. In contrast, higher plants generally are devoid of arachidonate and biosynthesize α-linolenate as one of the major polyunsaturated fatty acids. Since α-linolenate derived dinor isoprostanes differ in structure from mammalian dinor isoprostanes, plant dinor isoprostanes have been termed phytoprostanes [5].


Jasmonic Acid Butyl Hydroperoxide Physiol Regulatory Integrative Comp Tobacco Cell Suspension Culture Trace Fatty Acid 
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  1. 1.
    Roberts LJ, Morrow JD. Products of the isoprostane pathway: unique bioactive compounds and markers of lipid peroxidation. Cell Mol Life Sci 2002; 59:808–820.PubMedCrossRefGoogle Scholar
  2. 2.
    Mueller MJ. Radically novel prostaglandins in animals and plants: the isoprostanes. Chem Biol 1998; 5:323–333.CrossRefGoogle Scholar
  3. 3.
    Hou X, Roberts II LJ, Taber DF, Morrow JD, Kanai K, Gobeil JR, F Beauchamp MH, Bemier SG, Lepage G, Varma DR, Chemtob S. 2,3-Dinor-5,6-dihydro-15-F2t-isoprostane: a bioactive prostanoid metabolite. Am J Physiol Regulatory Integrative Comp Physiol 2001; 281:R391–R400.Google Scholar
  4. 4.
    Burke A, Lawson JA, Meagher EA, Rokach J, FitzGerald GA. J Biol Chem 2000; 275:2499–2504.PubMedCrossRefGoogle Scholar
  5. 5.
    Imbusch R, Mueller MJ. Formation of isoprostane F2-like compounds (phytoprostanes F) from a-linolenic acid in plants. Free Rad Biol Med 2000; 28:720–726.Google Scholar
  6. 6.
    Parchmann S, Mueller MJ. Evidence for the formation of dinor isoprostanes E1 from α-linolenic acid in plants. J Biol Chem 1998; 273:32650–32655.PubMedCrossRefGoogle Scholar
  7. 7.
    Thoma I, Loeffler L, Sinha AK, Gupta M, Krischke M, Steffan B, Roitsch T, Mueller MJ. Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants. Plant J, 2003, acceptedGoogle Scholar
  8. 8.
    Krischke M, Loeffler C, Mueller MJ. Biosynthesis of 14,15-dehydro-12-oxo-phytodienoic acid and related cyclopentenones via the phytoprostane D1 pathway. Phytochemistry 2003; in press.Google Scholar
  9. 9.
    Chen Y, Morrow JD, Roberts II LJ. Formation of reactive cyclopentenone compounds in vivo as products of the isoprostane pathway. J Biol Chem 1999; 274:10863–10868.PubMedCrossRefGoogle Scholar
  10. 10.
    Mueller MJ, Brodschelm W, Spannagl E, Zenk MH. Signaling in the elicitation process is mediated through the octadecanoid pathway leading to jasmonic acid. Proc Natl Acad Sci USA 1993; 90:7490–7494.PubMedCrossRefGoogle Scholar
  11. 11.
    Mueller MJ, Brodschelm W. Quantification of jasmonic acid by capillary gas chromatography-negative chemical ionization-mass spectrometry. Anal Biochem, 1994;218:425–435.PubMedCrossRefGoogle Scholar
  12. 12.
    Parchmann S, Gundlach H, Mueller MJ. Induction of 12-oxo-phytodienoic acid in wounded plants and elicited plant cell cultures. Plant Physiol 1997; 115:1057–1064.PubMedCrossRefGoogle Scholar
  13. 13.
    Mueller MJ. Enzymes involved in jasmonic acid biosynthesis. Physiol Plant 1997; 100:653–663.CrossRefGoogle Scholar
  14. 14.
    Imbusch R, Mueller MJ. Analysis of oxidative stress and wound-inducible dinor isoprostanes F1 (phytoprostanes F1 in plants. Plant Physiol 2000; 124:1293–1303.PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2003

Authors and Affiliations

  • Christane Loeffler
  • Ingeborg Thoma
  • Markus Krischke
  • Martin J. Mueller
    • 1
  1. 1.Julius-von-Sachs-Institut fuer Biowissenschaflen, Pharmazeutische BiologieWuerzburgGermany

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