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Amino acid conjugates as metabolites of the plant growth regulator dihydrojasmonic acid in barley (Hordeum vulgare)

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Abstract

The biotransformation of [2-14C](±)9, 10-dihydrojasmonic acid (DJA) was studied in excised shoots of 6-day-old barley seedlings after 72 h. From the ethyl acetate extract, some minor metabolites were isolated and purified by DEAE-Sephadex A-25 chromatography, thin-layer chromatography (TLC), C18-cartridges, and high-performance liquid chromatography (HPLC). The structural identification of these metabolites was performed by gas chromatography-mass spectrometry (GC-MS), circular dichroism (CD), and amino acid analysis, and the following amino acid conjugates were found:N-[(−)9,10-dihydrojasmonoyl]valine,N-[(−)9,10-dihydrojasmonoyl]isoleucine,N-[9,10-dihydrojasmonoyl]leucine,N-[11-hydroxy-9,10-dihydrojasmonoyl]valine,N-[11-hydroxy-9,10-dihydrojasmonoyl]isoleucine,N-[12-hydroxy-9,10-dihydrojasmonoyl]isoleucine; and the cucurbic acid-related compoundsN-{[3-hydroxy-2(4-hydroxypentyl)-cyclopent-1-yl]-acetyl}isoleucine andN-{[3-hydroxy-2(5-hydroxypentyl)-cyclopent-1-yl]-acetyl}isoleucine. The results suggest conjugation with isoleucine and valine, as well as preferential hydroxylation at position C-11 or hydrogenation at position C-6, as being important steps in the metabolism of (±)DJA in barley shoots.

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Authors and Affiliations

  1. Institute of Plant Biochemistry, Academy of Sciences of the GDR, Weinberg 3, 4050, Halle (Saale), GDR

    A. Meyer, J. Schmidt, D. Gross, S. Vorkefeld & G. Sembdner

  2. Institute of Biology and Geology, University of Tromsö, Tromsö, Norway

    E. Jensen

  3. Central Institute of Genetics and Research on Cultivated Plants, Academy of Sciences of the GDR, 4325, Gatersleben, GDR

    A. Rudolph

Authors
  1. A. Meyer
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  2. J. Schmidt
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  3. D. Gross
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  4. E. Jensen
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  5. A. Rudolph
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  6. S. Vorkefeld
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  7. G. Sembdner
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Meyer, A., Schmidt, J., Gross, D. et al. Amino acid conjugates as metabolites of the plant growth regulator dihydrojasmonic acid in barley (Hordeum vulgare). J Plant Growth Regul 10, 17–25 (1991). https://doi.org/10.1007/BF02279306

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  • DOI: https://doi.org/10.1007/BF02279306

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