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Biochemistry (Moscow)

, Volume 71, Issue 5, pp 571–580 | Cite as

Leukocytic myeloperoxidase-mediated formation of bromohydrins and lysophospholipids from unsaturated phosphatidylcholines

  • O. M. PanasenkoEmail author
  • H. Spalteholz
  • J. Schiller
  • J. Arnhold
Article

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.

Key words

myeloperoxidase hypobromite HOBr unsaturated phospholipids bromohydrin lysophosphatidylcholine MALDI-TOF mass spectrometry 

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

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Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • O. M. Panasenko
    • 1
    Email author
  • H. Spalteholz
    • 2
  • J. Schiller
    • 2
  • J. Arnhold
    • 2
  1. 1.Research Institute of Physico-Chemical MedicineMoscowRussia
  2. 2.Institute of Medical Physics and BiophysicsUniversity of LeipzigLeipzigGermany

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