Skip to main content
Plant Physiology logoLink to Plant Physiology
. 1991 Nov;97(3):1059–1072. doi: 10.1104/pp.97.3.1059

Hydroperoxide Lyase and Other Hydroperoxide-Metabolizing Activity in Tissues of Soybean, Glycine max

Harold W Gardner 1,2, David Weisleder 1,2, Ronald D Plattner 1,2
PMCID: PMC1081123  PMID: 16668490

Abstract

Hydroperoxide lyase (HPLS) activity in soybean (Glycine max) seed/seedlings, leaves, and chloroplasts of leaves required detergent solubilization for maximum in vitro activity. On a per milligram of protein basis, more HPLS activity was found in leaves, especially chloroplasts, than in seeds or seedlings. The total yield of hexanal from 13(S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid (13S-HPOD) from leaf or chloroplast preparations was 58 and 66 to 85%, respectively. Because of significant competing hydroperoxide-metabolizing activities from other enzymes in seed/seedling preparations, the hexanal yields from this source were lower (36-56%). Some of the products identified from the seed or seedling preparations indicated that the competing activity was mainly due to both a hydroperoxide peroxygenase and reactions catalyzed by lipoxygenase. Different HPLS isozyme compositions in the seed/seedling versus the leaf/chloroplast preparations were indicated by differences in the activity as a function of pH, the Km values, relative Vmax with 13S-HPOD and 13(S)-hydroperoxy-cis-9,trans-11,cis-15-octadecatrienoic acid (13S-HPOT), and the specificity with different substrates. With regard to the latter, both seed/seedling and chloroplast HPLS utilized the 13S-HPOD and 13S-HPOT substrates, but only seeds/seedlings were capable of metabolizing 9(S)-hydroperoxy-trans-10,cis-12-octadecadienoic acid into 9-oxononanoic acid, isomeric nonenals, and 4-hydroxynonenal. From 13S-HPOD and 13S-HPOT, the products were identified as 12-oxo-cis-9-dodecenoic acid, as well as hexanal from 13S-HPOD and cis-3-hexenal from 13S-HPOT. In seed preparations, there was partial isomerization of the cis-3 or cis-9 into trans-2 or trans-10 double bonds, respectively.

Full text

PDF
1059

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Blée E., Schuber F. Efficient epoxidation of unsaturated fatty acids by a hydroperoxide-dependent oxygenase. J Biol Chem. 1990 Aug 5;265(22):12887–12894. [PubMed] [Google Scholar]
  2. Christopher J., Pistorius E., Axelrod B. Isolation of an isozyme of soybean lipoxygenase. Biochim Biophys Acta. 1970 Jan 14;198(1):12–19. doi: 10.1016/0005-2744(70)90028-8. [DOI] [PubMed] [Google Scholar]
  3. Gardner H. W. Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism. Biochim Biophys Acta. 1989 Feb 20;1001(3):274–281. doi: 10.1016/0005-2760(89)90111-2. [DOI] [PubMed] [Google Scholar]
  4. Garssen G. J., Veldink G. A., Vliegenthart J. F., Boldingh J. The formation of threo-11-hydroxy-trans-12: 13-epoxy-9-cis-octadecenoic acid by enzymic isomerisation of 13-L-hydroperoxy-9-cis, 11-transoctadecadienoic acid by soybean lipoxygenase-1. Eur J Biochem. 1976 Feb 2;62(1):33–36. doi: 10.1111/j.1432-1033.1976.tb10094.x. [DOI] [PubMed] [Google Scholar]
  5. Garssen G. J., Vliegenthart J. F., Boldingh J. An anaerobic reaction between lipoxygenase, linoleic acid and its hydroperoxides. Biochem J. 1971 Apr;122(3):327–332. doi: 10.1042/bj1220327. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Gitler C. Use of ANS to detect phospholipids and apolar molecules in chromatograms. Anal Biochem. 1972 Nov;50(1):324–325. doi: 10.1016/0003-2697(72)90512-x. [DOI] [PubMed] [Google Scholar]
  7. Hamberg M., Hamberg G. Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.). Arch Biochem Biophys. 1990 Dec;283(2):409–416. doi: 10.1016/0003-9861(90)90662-i. [DOI] [PubMed] [Google Scholar]
  8. Kühn H., Wiesner R., Lankin V. Z., Nekrasov A., Alder L., Schewe T. Analysis of the stereochemistry of lipoxygenase-derived hydroxypolyenoic fatty acids by means of chiral phase high-pressure liquid chromatography. Anal Biochem. 1987 Jan;160(1):24–34. doi: 10.1016/0003-2697(87)90609-9. [DOI] [PubMed] [Google Scholar]
  9. Matthew J. A., Chan H. W., Galliard T. A simple method for the preparation of pure 9-D-hydroperoxide of linoleic acid and methyl linoleate based on the positional specificity of lipoxygenase in tomato fruit. Lipids. 1977 Mar;12(3):324–326. doi: 10.1007/BF02533358. [DOI] [PubMed] [Google Scholar]
  10. Smith P. K., Krohn R. I., Hermanson G. T., Mallia A. K., Gartner F. H., Provenzano M. D., Fujimoto E. K., Goeke N. M., Olson B. J., Klenk D. C. Measurement of protein using bicinchoninic acid. Anal Biochem. 1985 Oct;150(1):76–85. doi: 10.1016/0003-2697(85)90442-7. [DOI] [PubMed] [Google Scholar]
  11. Vick B. A., Zimmerman D. C. Metabolism of Fatty Acid Hydroperoxides by Chlorella pyrenoidosa. Plant Physiol. 1989 May;90(1):125–132. doi: 10.1104/pp.90.1.125. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Zimmerman D. C., Coudron C. A. Identification of Traumatin, a Wound Hormone, as 12-Oxo-trans-10-dodecenoic Acid. Plant Physiol. 1979 Mar;63(3):536–541. doi: 10.1104/pp.63.3.536. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Plant Physiology are provided here courtesy of Oxford University Press

RESOURCES