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Zimmerlin A, Salaün JP, Durst F, et al. Cytochrome p-450-dependent hydroxylation of lauric Acid at the subterminal position and oxidation of unsaturated analogs in wheat microsomes. Plant Physiol. 1992;100(2):868-73doi: 10.1104/pp.100.2.868.
Zimmerlin, A., Salaün, J. P., Durst, F., & Mioskowski, C. (1992). Cytochrome p-450-dependent hydroxylation of lauric Acid at the subterminal position and oxidation of unsaturated analogs in wheat microsomes. Plant physiology, 100(2), 868-73. https://doi.org/10.1104/pp.100.2.868
Zimmerlin, A, et al. "Cytochrome p-450-dependent hydroxylation of lauric Acid at the subterminal position and oxidation of unsaturated analogs in wheat microsomes." Plant physiology vol. 100,2 (1992): 868-73. doi: https://doi.org/10.1104/pp.100.2.868
Zimmerlin A, Salaün JP, Durst F, Mioskowski C. Cytochrome p-450-dependent hydroxylation of lauric Acid at the subterminal position and oxidation of unsaturated analogs in wheat microsomes. Plant Physiol. 1992 Oct;100(2):868-73. doi: 10.1104/pp.100.2.868. PMID: 16653069; PMCID: PMC1075637.
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Plant Physiol. 1992 Oct;100(2):868-73. doi: 10.1104/pp.100.2.868.

Cytochrome p-450-dependent hydroxylation of lauric Acid at the subterminal position and oxidation of unsaturated analogs in wheat microsomes.

Plant physiology

A Zimmerlin, J P Salaün, F Durst, C Mioskowski

Affiliations

  1. Département d'Enzymologie Cellulaire et Moléculaire, Institut de Biologie Moléculaire des Plantes, Centre National de la Recherche Scientifique UPR 406, 28, rue Goethe, F-67083 Strasbourg Cedex, France.

PMID: 16653069 PMCID: PMC1075637 DOI: 10.1104/pp.100.2.868

Abstract

Microsomes from etiolated wheat (Triticum aestivum L. cv Etoile de Choisy) shoots catalyzed the reduced nicotinamide adenine dinucleotide phosphate-dependent hydroxylation of lauric acid predominantly at the subterminal or (omega-1) position (65%). Minor amounts of 10-hydroxy- (31%) and 9-hydroxylaurate (4%) were also formed. The reaction was catalyzed by cytochrome P-450, since enzyme activity was strongly inhibited by tetcyclacis, carbon monoxide, and antibodies against NADPH-cytochrome c (P-450)-reductase. The apparent K(m) for lauric acid was estimated to be 8.5 +/- 2.0 mum. Seed treatment with the safener naphthalic acid anhydride or treatment of seedlings with phenobarbital increased cytochrome P-450 content and lauric acid hydroxylase (LAH) activity of the microsomes. A combination of both treatments further stimulated LAH activity. A series of radiolabeled unsaturated lauric acid analogs (8-, 9-, 10-, and 11-dodecenoic acids) was used to explore the regioselectivity and catalytic capabilities of induced wheat microsomes. It has been found that wheat microsomes catalyzed the reduced nicotinamide adenine dinucleotide phosphate-dependent epoxidation of sp2 carbons concurrently with hydroxylation at saturated positions. The regioselectivity of oxidation of the unsaturated substrates and that of lauric acid were similar. Preincubation of wheat microsomes with reduced nicotinamide adenine dinucleotide phosphate and 11-dodecenoic acid resulted in a partial loss of LAH activity.

References

  1. Biochem Biophys Res Commun. 1990 Mar 16;167(2):498-503 - PubMed
  2. Mol Cell Biochem. 1975 Aug 30;8(2):69-79 - PubMed
  3. Annu Rev Pharmacol Toxicol. 1983;23:481-503 - PubMed
  4. Biochem J. 1986 Apr 15;235(2):365-73 - PubMed
  5. Pharmacol Ther. 1980;11(3):469-96 - PubMed
  6. Eur J Biochem. 1978 Sep 15;90(1):155-9 - PubMed
  7. Biochem Int. 1983 Feb;6(2):191-8 - PubMed
  8. Biochemistry. 1973 Oct 23;12(22):4488-98 - PubMed
  9. Biochem Biophys Res Commun. 1990 Apr 16;168(1):206-13 - PubMed
  10. J Biochem. 1985 Mar;97(3):755-63 - PubMed
  11. Mol Cell Biochem. 1983;53-54(1-2):155-61 - PubMed
  12. Methods Enzymol. 1979;63:103-38 - PubMed
  13. Plant Physiol. 1982 Jul;70(1):122-6 - PubMed
  14. Arch Biochem Biophys. 1988 Feb 1;260(2):540-5 - PubMed
  15. Xenobiotica. 1989 Oct;19(10):1123-48 - PubMed
  16. J Biol Chem. 1984 Apr 10;259(7):4136-41 - PubMed
  17. J Lipid Res. 1990 Aug;31(8):1477-82 - PubMed
  18. Plant Physiol. 1992 Oct;100(2):874-81 - PubMed
  19. Arch Biochem Biophys. 1984 Jul;232(1):1-7 - PubMed
  20. Plant Physiol. 1980 Oct;66(4):600-4 - PubMed

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