Formation of lysophospholipids from unsaturated phosphatidylcholines under the influence of hypochlorous acid

作者: J Arnhold , Anatoly N Osipov , H Spalteholz , Oleg M Panasenko , J Schiller

DOI: 10.1016/S0304-4165(02)00271-4

关键词: SaponificationDocosahexaenoic acidUnsaturated fatty acidHydrolysisHypochlorous acidSaturated fatty acidFatty acidLysophospholipidsChemistryOrganic chemistryChromatography

摘要: The formation of lysophosphatidylcholines from unsaturated phosphatidylcholines upon treatment with hypochlorous acid was evaluated by means MALDI-TOF mass spectrometry and 31P NMR spectroscopy. With an increasing number double bonds in a fatty residue, the yield saturated residue increased considerably comparison to total amount higher molecular weight products like chlorohydrins glycols. High amounts were formed phospholipids containing arachidonic or docosahexaenoic residues. In monounsaturated residues, position bond did not influence lyso-products. Besides exclusive chlorohydrin glycol, caused cleavage independent its location at first second glycerol backbone. contrast, strong alkaline conditions, i.e. saponification led also hydrolysis phosphatidylcholines. It is concluded that both spectroscopy are able detect lysophosphatidylcholines. We conclude lysophospholipids can be relevant vivo under acute inflammatory conditions.

参考文章(45)
A J Kettle, C C Winterbourn, Superoxide-dependent hydroxylation by myeloperoxidase Journal of Biological Chemistry. ,vol. 269, pp. 17146- 17151 ,(1994) , 10.1016/S0021-9258(17)32533-4
DS Lin, WE Connor, DP Wolf, M Neuringer, DL Hachey, Unique lipids of primate spermatozoa: desmosterol and docosahexaenoic acid. Journal of Lipid Research. ,vol. 34, pp. 491- 499 ,(1993) , 10.1016/S0022-2275(20)40740-0
J. Carrell Morris, The Acid Ionization Constant of HOCl from 5 to 35 The Journal of Physical Chemistry. ,vol. 70, pp. 3798- 3805 ,(1966) , 10.1021/J100884A007
Jürgen Schiller, Jürgen Arnhold, Wilfried Gründer, Klaus Arnold, THE ACTION OF HYPOCHLOROUS ACID ON POLYMERIC COMPONENTS OF CARTILAGE Biological chemistry Hoppe-Seyler. ,vol. 375, pp. 167- 172 ,(1994) , 10.1515/BCHM3.1994.375.3.167
A. J. Kettle, C. C. Winterbourn, Myeloperoxidase: a key regulator of neutrophil oxidant production Redox Report. ,vol. 3, pp. 3- 15 ,(1997) , 10.1080/13510002.1997.11747085
R.A Meyers, Encyclopedia of Analytical Chemistry s.n.. ,(2000)
Johannes Everse, Kathleen E. Everse, Matthew B. Grisham, Peroxidases in chemistry and biology CRC Press. ,(1990)
David G. Gorenstein, Phosphorus-31 NMR : principles and applications Academic Press. ,(1984)