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Formation of (2E)-4-Hydroxy-2-nonenal and (2E)-4-Hydroxy-2-hexenal by Plant Enzymes: A Review Suggests a Role in the Physiology of Plants

DOI: 10.4236/aer.2016.42006, PP. 56-61

Keywords: (3Z)-Nonenal, (3Z)-Hexenal, (2E)-4-Hydroxy-2-nonenal, (2E)-4-Hydroxy-2-hexenal, (2E)-4-Hydroperoxy-2-hexenal, Lipoxygenase, Hydroperoxide Peroxygenase, Hydroperoxide Lyase, (2E)-4-Hydroperoxy-2-Nonenal, 3, 4-Epoxynonanal, (2E)-4-Oxo-2-nonenal, Glycine max, Vica faba, Plant Pathogen

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Abstract:

It is demonstrated that (3Z)-nonenal (NON) and (3Z)-hexenal (HEX) are oxidized in a cascade by lipoxygenase (LOX) and hydroperoxide peroxygenase (HP peroxygenase) into (2E)-4-hydroxy-2- nonenal (HNE) and (2E)-4-hydroxy-2-hexenal (HHE), respectively. In turn, HNE inactivates LOX terminating the cascade. The hydroxy-alkenals produced serve to inhibit plant pathogens, which initiated the cascade. In addition to LOX, other unknown oxygenases may be involved in the cascade.

References

[1]  Noordermeer, M.A., Fuessner, I., Kolbe, A., Veldink, G.A. and Vliegenthart, J.F.G. (2000) Oxygenation of (3Z)-Alkenals to 4-Hydroxy-(2E)-Alkenals in Plant Extracts: A Nonenzymatic Process. Biochemical and Biophysical Research Communications, 277, 112-116. http://dx.doi.org/10.1006/bbrc.2000.3641
[2]  Gardner, H.W. and Hamberg, M. (1993) Oxygenation of (3Z)-Nonenal to (2E)-4-Hydroxy-2-nonenal in the Broad Bean (Vica faba L.). Journal of Biological Chemistry, 268, 6971-6977.
[3]  Takamura, H. and Gardner, H.W. (1996) Oxygenation of (3Z)-Alkenal to (2E)-4-Hydroxy-2-alkenal in Soybean Seed (Glycine max L.). Biochimica et Biophysica Acta, 1303, 83-91.
http://dx.doi.org/10.1016/0005-2760(96)00076-8
[4]  Schneider, C., Tallman, K.A,, Porter, N.A. and Brash, A.R. (2001) Two Distinct Pathways of Formation of 4-Hydroxy- nonenal Mechanisms of Nonenzymatic Transformation of the 9- and 13-Hydroperoxides of Linoleic Acid to 4-Hydro- xyalkenals. The Journal of Biological Chemistry, 276, 20831-20838.
http://dx.doi.org/10.1074/jbc.M101821200
[5]  Schneider, C., Porter, N.A. and Brash, A.R. (2008) Routes to 4-Hydroxynonenal: Fundamental Issues in the Mechanisms of Lipid Peroxidation. The Journal of Biological Chemistry, 283, 15539-15543.
http://dx.doi.org/10.1074/jbc.R800001200
[6]  Grechkin, A.N., Mukhtarova, L.S. and Hamberg, M. (2005) Thermal Conversions of Trimethylsilyl Peroxides of Linoleic and Linolenic Acid. Chemistry and Physics of Lipids, 138, 93-101.
http://dx.doi.org/10.1016/j.chemphyslip.2005.09.001
[7]  Gardner, H.W., Weisleder, D. and Plattner, R.D. (1991) Hydroperoxide Lyase and Other Hydroperoxide-Metabolizing Activity in Tissues of Soybean, Glycine max. Plant Physiology, 97, 1059-1072.
http://dx.doi.org/10.1104/pp.97.3.1059
[8]  Hamberg, M., and Fahlstadius, P. (1992) On the Specificity of a Fatty Acid Epoxygenase in Broad Bean (Vicia faba L.). Plant Physiology, 99, 987-995. http://dx.doi.org/10.1104/pp.99.3.987
[9]  Hamberg, M. and Hamberg, G. (1990) Hydroperoxide-Dependent Epoxidation of Unsaturated Fatty Acids in the Broad Bean (Vica faba L.). Archives of Biochemistry and Biophysics, 283, 409-416.
http://dx.doi.org/10.1016/0003-9861(90)90662-I
[10]  Blee, E. and Schuber, F. (1990) Efficient Epoxidation of Unsaturated Fatty Acids by a Hydroperoxide-Dependent Oxygenase. The Journal of Biological Chemistry, 265, 12887-12894.
[11]  Blee, E. and Schuber, F. (1990) Stereochemistry of the Epoxidation of Fatty Acids Catalyzed by Soybean Peroxygenase. Biochemical and Biophysical Research Communications, 173, 1354-1360.
http://dx.doi.org/10.1016/S0006-291X(05)80937-4
[12]  Gardner H.W., Bartelt, R.J. and Weisleder, D. (1992) A Facile Synthesis of 4-Hydroxy-2(E)-nonenal. Lipids, 27, 686-689. http://dx.doi.org/10.1007/BF02536025
[13]  Gardner, H.W., Weisleder, D. and Plattner, R.D. (1991) An Enzyme Preparation from Seeds of Soybean Glycine max Converts 9S-Hydroperoxide of Linoleic Acid into 4-Hydroxy-trans-2-nonenal. Plant Physiology Meeting, Albuquerque, NM, 28 July-1 August 1991.
[14]  Gardner, H.W. and Grove, M.J. (1998) Soybean Lipoxygenase-1 Oxidizes 3Z-Nonenal. Plant Physiology, 116, 1359- 1366. http://dx.doi.org/10.1104/pp.116.4.1359
[15]  Garssen, G.J., Vliegenthart, J.F.G. and Boldingh, J. (1971) An Anaerobic Reaction between Lipoxygenase, Linoleic Acid and Its Hydroperoxide. Biochemical Journal, 122, 327-332.
http://dx.doi.org/10.1042/bj1220327
[16]  Verhagen, J., Veldink, G.A., Egmond, M.R., Vliegenthart, J.F.G., Boldingh, J. and van der Star, J. (1978) Steady-State Kinetics of the Anaerobic Reaction of Soybean Lipoxygenase-1 with Linoleic Acid and 13-L-hydroperoxylinoleic Acid. Biochimica et Biophysica Acta (BBA)—Lipids and Lipid Metabolism, 529, 369-379. http://dx.doi.org/10.1016/0005-2760(78)90081-4
[17]  Smith, W.L. and Lands, W.E.M. (1972) Oxygenation of Unsaturated Fatty Acids by Soybean Lipoxygenase. The Journal of Biological Chemistry, 247, 1038-1047.
[18]  Fukushige, H., Wang, C., Simpson, T.D., Gardner, H.W. and Hildebrand, D.F. (2005) Purification of Linoleic Acid Hydroperoxides Generated by Soybean Seed Lipoxygenases 2 and 3. Journal of Agricultural and Food Chemistry, 53, 5691-5694. http://dx.doi.org/10.1021/jf047958o
[19]  Gardner, H.W. (1998) 9-Hydroxy-traumatin, a New Metabolite of the Lipoxygenase Pathway. Lipids, 33, 745-749. http://dx.doi.org/10.1007/s11745-998-0265-z
[20]  Nakashima, A., von Reuss, S.H., Tasaka, H., Nomura, M., Mochizuki, S., Iijima, Y., Aoki, K., Shibata, D., Boland, W., Takabayashi, J. and Matsui, K. (2013) Traumatin- and Dinortraumatin-Containing Galactolipids in Arabidopsis: Their Formation in Tissue-Disrupted Leaves as Counterparts of Green Leaf Volatiles. The Journal of Biological Chemistry, 288, 26078-26088. http://dx.doi.org/10.1074/jbc.m113.487959
[21]  Gardner, H.W. and Deighton, N. (2001) Effect of 4-Hydroxy-2(E)-nonenal on Soybean Lipoxygenase-1. Lipids, 36, 623-628. http://dx.doi.org/10.1007/s11745-001-0766-9
[22]  Boyington, J.C., Gtaffney, B.J. and Amzel, L.M. (1993) The Three-Dimensional Structure of an Arachidonic Acid 15-Lipoxygenase. Science, 260, 1482-1486. http://dx.doi.org/10.1126/science.8502991
[23]  Minor, W., Steczko, J., Stec, B., Otwinowski, Z., Bolin, J.T., Walter, R. and Axelrod, B. (1996) Crystal Structure of Soybean Lipoxygenase L-1 at 1.4 Angstrom Resolution. Biochemistry, 35, 10687-10701. http://dx.doi.org/10.1021/bi960576u
[24]  Uchida, K. and Stadtman, E.R. (1992) Modification of Histidine Residues in Proteins by Reaction with 4-Hydroxyno- nenal. Proceedings of the National Academy of Sciences of the United States of America, 89, 4544-4548. http://dx.doi.org/10.1073/pnas.89.10.4544
[25]  Deighton, N., Muckenschnabel, I., Goodman, B.A. and Williamson, B. (1999) Lipid Peroxidation and the Oxidative Burst Associated with Infection of Capsicum annuum by Botrytis cinerea. The Plant Journal, 20, 485-492. http://dx.doi.org/10.1046/j.1365-313x.1999.00622.x
[26]  Adams, L.K., Benson, E.E., Staines, H.J., Bremmer, D.H., Millam, S. and Deighton, N. (1999) Effects of the Lipid Peroxidation Products 4-Hydroxy-2-nonenal and Malondialdehyde on the Proliferation and Morphogenetic Development of in Vitro Plant Cells. Journal of Plant Physiology, 155, 376-386.
http://dx.doi.org/10.1016/S0176-1617(99)80120-5
[27]  Kohlmann, M., Bachmann, A., Weichert, H., Kohbe, A., Balkenhohl, T., Wasternack, C. and Feussner, I. (1999) Formation of Lipoxygenase-Pathway-Derived Aldehydes in Barley Leaves upon Methyl Jasmonate Treatment. European Journal of Biochemistry, 260, 885-895.
http://dx.doi.org/10.1046/j.1432-1327.1999.00231.x
[28]  Gardner, H.W. (1989) Soybean Lipoxygenase-1 Enzymically Forms Both (9S)- and (13S)-Hydroperoxides from Linoleic Acid by a pH-Dependent Mechanism. Biochimica et Biophysica Acta (BBA)—Lipids and Lipid Metabolism, 1001, 274-281. http://dx.doi.org/10.1016/0005-2760(89)90111-2

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