Abstract
Using MALDI-TOF mass spectrometry, we have shown that leukocytic myeloperoxidase (MPO) in the presence of its substrates (H2O2 and Br−) does not induce any changes in saturated 1,2-dipalmitoyl-sn-glycero-3-phosphocholine. Incubation of liposomes prepared from mono-unsaturated phosphatidylcholine (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) with the (MPO + H2O2 + Br−) system resulted in formation of bromohydrins as the main products. 1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine (lysophosphatidylcholine) was the main product of the reaction of polyunsaturated phosphatidylcholine (1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine) with the (MPO + H2O2 + Br−) system. The formation of lysophospholipids as well as of bromohydrins was not observed when the enzyme or one of its substrates (H2O2 or Br−) was absent from the incubation medium, or if an inhibitor of MPO (sodium azide) or hypobromite scavengers (taurine or methionine) were added. Thus, it can be postulated that the formation of bromohydrins as well as lysophospholipids by the (MPO + H2O2 + Br−) system results from reactions of hypobromite formed during MPO catalysis with double bonds of acyl chains of phosphatidylcholine. Such destructive processes may take place in vivo in membrane-or lipoprotein-associated unsaturated lipids in centers of inflammation.
Similar content being viewed by others
Abbreviations
- DMPC:
-
1,2-dimyristoyl-sn-glycero-3-phosphocholine
- EPO:
-
eosinophil peroxidase
- HOCl/OCl− :
-
hypochlorite
- HOBr/OBr− :
-
hypobromite
- lyso-PC:
-
1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine
- MALDI-TOF:
-
matrix-assisted laser desorption/ionization time-of-flight mass spectrometry
- MPO:
-
myeloperoxidase
- PAPC:
-
1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine
- POPC:
-
1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine
References
Kettle, A. J., and Winterbourn, C. C. (1997) Redox Rep., 3, 3–15.
Carr, A. C., Decker, E. A., Park, Y. J., and Frei, B. (2001) Free Rad. Biol. Med., 31, 62–72.
Gaut, J. P., Yeh, G. C., Tran, H. D., Byun, J., Henderson, J. P., Richter, G. M., Brennan, M. L., Lusis, A. J., Belaaouaj, A., Hotchkiss, R. S., and Heinecke, J. W. (2001) Proc. Natl. Acad. Sci. USA, 98, 11961–11966.
Panasenko, O. M., Arnhold, J., and Sergienko, V. I. (2002) Biol. Membr. (Moscow), 19, 403–434.
Ohnishi, S., Murata, M., and Kawanishi, S. (2002) Cancer Lett., 178, 37–42.
Weiss, S. J. (1982) J. Biol. Chem., 257, 2947–2953.
Schiller, J., Arnhold, J., Grunder, W., and Arnold, K. (1994) Biol. Chem. Hoppe Seyler, 375, 167–172.
Spickett, C. M., Jerlich, A., Panasenko, O. M., Arnhold, J., Pitt, A. R., Stelmaszynska, T., and Schaur, R. J. (2000) Acta Biochim. Polonica, 47, 889–899.
Evgina, S. A., Panasenko, O. M., Sergienko, V. I., and Vladimirov, Yu. A. (1992) Biol. Membr. (Moscow), 19, 946–953.
Stelmaszynska, T., Kukovetz, E., Egger, G., and Schaur, R. J. (1992) Int. J. Biochem., 24, 121–128.
Panasenko, O. M., Evgina, S. A., Aidyraliev, R. K., Sergienko, V. I., and Vladimirov, Yu. A. (1994) Free Rad. Biol. Med., 16, 143–148.
Panasenko, O. M., Arnhold, J., Schiller, J., Arnold, K., and Sergienko, V. I. (1994) Biochim. Biophys. Acta, 1215, 259–266.
Panasenko, O. M., Evgina, S. A., Driomina, E. S., Sharov, V. S., Sergienko, V. I., and Vladimirov, Yu. A. (1995) Free Rad. Biol. Med., 19, 133–140.
Panasenko, O. M., and Arnhold, J. (1996) Biol. Membr. (Moscow), 13, 89–99.
Panasenko, O. M. (1997) Biofactors, 6, 181–190.
Drobnies, A. E., Venczel, E. A., and Cornell, R. B. (1998) Biochim. Biophys. Acta, 1393, 90–98.
Winterbourn, C. C., van den Berg, J. J., Roitman, E., and Kuypers, F. A. (1992) Arch. Biochem. Biophys., 296, 547–555.
Arnhold, J., Panasenko, O. M., Schiller, J., Vladimirov, Yu. A., and Arnold, K. (1995) Chem. Phys. Lipids, 78, 55–64.
Jerlich, A., Pitt, A. R., Schaur, R. J., and Spickett, C. M. (2000) Free Rad. Biol. Med., 28, 673–682.
Arnhold, J., Osipov, A. N., Spalteholz, H., Panasenko, O. M., and Schiller, J. (2001) Free Rad. Biol. Med., 31, 1111–1119.
Panasenko, O. M., Osipov, A. N., Schiller, J., and Arnhold, J. (2002) Biochemistry (Moscow), 67, 889–900.
Arnhold, J., Osipov, A. N., Spalteholz, H., Panasenko, O. M., and Schiller, J. (2002) Biochim. Biophys. Acta, 1572, 91–100.
Thomas, E. L., Bozeman, P. M., Jefferson, M. M., and King, C. C. (1995) J. Biol. Chem., 270, 2906–2913.
Furtmuller, P. G., Burner, U., and Obinger, C. (1998) Biochemistry, 37, 17923–17930.
Carr, A., van den Berg, J. J. M., and Winterbourn, C. C. (1998) Biochim. Biophys. Acta, 1392, 254–264.
Carr, A., Winterbourn, C. C., and van den Berg, J. J. M. (1996) Arch. Biochem. Biophys., 327, 227–233.
Schiller, J., Arnhold, J., Benard, S., Mueller, M., Reichl, S., and Arnold, K. (1999) Analyt. Biochem., 267, 46–56.
Petkovic, M., Schiller, J., Mueller, M., Benard, S., Reichl, S., Arnold, K., and Arnhold, J. (2001) Analyt. Biochem., 289, 202–216.
Spalteholz, H., Wenske, K., Panasenko, O. M., Schiller, J., and Arnhold, J. (2004) Chem. Phys. Lipids, 129, 85–96.
Nesmeyanov, A. N., and Nesmeyanov, N. A. (1974) Fundamentals of Organic Chemistry [in Russian], Vol. 1, Khimiya, Moscow, pp. 160–181.
Siess, W., Zangl, K. J., Essler, M., Bauer, M., Brandl, R., Corrinth, C., Bittman, R., Tigyi, G., and Aepfelbacher, M. (1999) Proc. Natl. Acad. Sci. USA, 96, 6931–6936.
Yokoyama, M., Inoue, N., and Kawashima, S. (2000) Ann. N. Y. Acad. Sci., 902, 241–247.
Kita, T., Kume, N., Yokode, M., Ishii, K., Arai, H., Horiuchi, H., Moriwaki, H., Minami, M., Kataoka, H., and Wakatsuki, Y. (2000) Ann. N. Y. Acad. Sci., 902, 95–100.
Kohno, M., Yokokawa, K., Yasunari, K., Minami, M., Kano, H., Hanehira, T., and Yoshikawa, J. (1998) Circulation, 98, 353–359.
Rikitake, Y., Hirata, K., Kawashima, S., Inoue, N., Akita, H., Kawai, Y., Nakagawa, Y., and Yokoyama, M. (2000) Atherosclerosis, 152, 79–87.
Froese, D. E., McMaster, J., Man, R. Y., Choy, P. C., and Kroeger, E. A. (1999) Mol. Cell. Biochem., 197, 1–6.
Watanabe, T., Pakala, R., Katagiri, T., and Benedict, C. R. (2001) J. Hypertens., 19, 1065–1073.
Watanabe, T., Pakala, R., Katagiri, T., and Benedict, C. R. (2001) Circulation, 104, 16–18.
Furtmuller, P. G., Jantschko, W., Zederbauer, M., Jakopitsch, C., Arnhold, J., and Obinger, C. (2004) Jpn. J. Infect. Dis., 57, S30–S31.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © O. M. Panasenko, H. Spalteholz, J. Schiller, J. Arnhold, 2006, published in Biokhimiya, 2006, Vol. 71, No. 5, pp. 707–718.
Rights and permissions
About this article
Cite this article
Panasenko, O.M., Spalteholz, H., Schiller, J. et al. Leukocytic myeloperoxidase-mediated formation of bromohydrins and lysophospholipids from unsaturated phosphatidylcholines. Biochemistry (Moscow) 71, 571–580 (2006). https://doi.org/10.1134/S0006297906050178
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1134/S0006297906050178