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  1. 1. Synthesis and some properties of phosphatidylhydroxyacetone as à new phospholipid formed by free-radical fragmentation of cardiolipin Vasilkevich Alexey, Kisel Mikhail Minsk, Belarus O OO C RP O O O C R O O O A number of biochemical processes in body as well as external physical and chemical condition is accompanied by the formation of reactive oxygen and nitrogen intermediates, which may afterwards cause cellular damage. Determination of the mentioned processes pathways and the role of the newly formed substances is an important biochemical subject. P O O O O R OH O P O O O R' OH H2O P O O O O R OH O P O O O R' O O O H P OH O O O R H O O P O O O R' LH L O O P O O O R' Phosphatidylhydroxyacetone (PHA) is the phospholipid along with phosphatidic acid (PA) found in mouse liver mitochondria subjected to oxidative stress (Yurkova, 2008). PA and PHA are detected as cardiolipin fragmentation products by thin-layer chromatography combined with MALDI-TOF mass spectrometry in oxidized samples, but not in unperturbed ones. The formation of PAand PHAin copper-treated model membrane correlats well with the decrease of cardiolipin (Yurkova, 2011). We have been first to synthesize PHA from phosphatidylcholine at preparative amount by the means of microbial phospholipase D from Streptomyces netropsis. The yield comprised about 80 %. Reaction time: 30 min, temperature 37 °Ñ, 1 ml reaction mixture chloroform:water 2:1 contained PC (35 mg), hydroxyacetone (20 µl), phospolipase D and NaAc buffer (pH 5,5). O OO C C13H27 P O O O C C13H27 O O OO C C13H27 P O O OPhospholipase D C C13H27 O O OH HO N+ O O ON+ Dimyristoylphosphatidylcholine Dimyristoylphosphatidylhydroxyacetone -1 1622 cm PHA PC 30 40 50 60 70 80 90 100 110 120 130 140 0 20 40 60 80 100 d, nm PHA percentage, % Liposome diameter Calculation by liposome number Calculation by liposome size - 31P NMR 4.71 4.93 PC PHA Reference: Triphenylphosphine Equipment: NMR: Avance 500 (Bruker) IR: FTIR-spectrophotometer Bomem Michelson 100 Liposome size determination: 90Plus Particle Size Analyzer, Brookhaven Instruments Corporation References: Yurkova et al. Archives of Biochemistry and Biophysics 480 (2008) 17–26, Yurkova et al. Chemistry and Physics of Lipids 164 (2011) 393– 400 Phosphatidylhydroxyacetone (PHA) Why to study? ?-The new synthetic phospholipid having carbonyl group may exhibit new biologically active properties ?-Allows to study the role of cardiolipin fragmentation processes in body more deeply. Laboratory of Lipid Chemistry Head of laboratory - Prof. Mikhail Kisel, D.Sc. tel. +375 (17) 263-71-31 e-mail: Research Areas ?Chemical and enzymatic synthesis of physiologically active lipids and related compounds; ?Study of enzymatic and free-radical reactions mechanisms leading to the signal lipids formation and the addressed regulation of such reactions by lipid effectors; ?Construction of liposomal drug-delivery systems; ?Synthesis and investigation of lipoid compounds for plant protection. Applied Research ?Technological process for 5-aminolevulinic acid hydrochloride which is the chemical substance for "Alamin" – a preparation for diagnostics and therapy of bladder cancer. ?Technological process for 5-aminolevulinic acid hexyl ester which is the effective regulator of plant growth. ?Preparative form of systemic fungicide "Baifucide" (active substance difenoconazole) for plant protection against fungal disease. ?Fluorescent and chromogenic lipid substrates for assaying lipolytic enzymes. - 1H NMR 1H NMR DM PC DM PHA (CH 3 ) 3 choline CH 2 hydroxyacetone CH 3 hydroxyacetone Modified method: Samples in D O2 Detergent CHAPS Reference Triphenylphosphine 0 min 15 min PHA PC PC Thin-layer chromatography Eluent: chloroform-methanol-water (65-25-4). Revealing reagent: molybdate reagent (Vaskovsky, 1975)


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