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Release of 1-0-Alkylglyceryl 3-Phosphorylcholine, O-Deacetyl

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Release of 1-0-Alkylglyceryl 3-Phosphorylcholine, O-Deacetyl Proc. Natil. Acad. Sci. USA Vol. 77, No. 12, pp. 7019-7023, December 1980 Biochemistry Release of 1-0-alkylglyceryl 3-phosphorylcholine, O-deacetyl platelet-activating factor, from leukocytes: Chemical ionization mass spectrometry of phospholipids (platelet aggregation/anaphylaxis mediator/phospholipase A2) JUDITH POLONSKY*, MARTINE TENCE*t, PIERRE VARENNE*, BHUPESH C. DAS*, JEAN LUNELt, AND JACQUES BENVENISTEt *Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, 91190 Gif-sur-Yvette, France; tInstitut National de la Sante et de la Recherche MWdicale, U. 131, 32 rue des Carnets, 92140 Clamart, France; and *Rh6ne-Poulenc Recherche et D6veloppement, Centre Nicolas Grillet 94400 Vitry, France Communicated by D. H. R. Barton, August 12, 1980 ABSTRACT Evidence is presented for the simultaneous physicochemical and biological properties of PAF. Because this release of platelet-activating factor (PAF-acether) and of its was obtained by successive methylation, hydrogenation, and deacetylated derivative (lyso-PAF-acether) from hog leukocytes. On the basis of spectroscopy and chemical reactions, the acetylation of the commercially available lyso-ethanolamine structure of 0-deacetyl-PAF is shown to be 1-aalkylglyceryl plasmalogen, the structure 1-O-alkyl-2-O-acetyl-sn-glyceryl 3-phosphorylcholine, an alkyl ether analog of lyso-phosphati- 3-phosphorylcholine and the name PAF-acether were proposed dylcholine. Acetylation of lyso-PAF yields a compound with (11). The same result has been reached by Hanahan's group (12) biological activity and chromatographical behavior indistin- for PAF and also by Snyder's group (13) for antihypertensive guishable from those of native PAF. Lyso-PAF may be consid- ered to be either the precursor or the enzymatic degradation polar renomedillary lipid (APRL) using choline plasmalogen product of PAF. The usefulness of chemical ionization mass as starting material. Recently, 1-O-octadecyl-2-O-acetyl-sn for structural determination of phospholipids is glyceryl 3-phosphorylcholine was synthesized and it showed biological properties identical with those of PAF-acether (un- published data). Platelet-activating factor (PAF) is. a mediator of anaphylaxis We herein report the isolation and structural elucidation of and inflammation discovered in the early 1970s (1, 2). It ag- the PAF-acether precursor, 1-O-alkylglyceryl 3-phosphoryl- gregates rabbit, rat, guinea pig, and human platelets and lib- choline, which is released along with PAF by hog leukocytes. erates their vasoactive amines. PAF is released by blood leu- Acetylation of this glyceryl ether phosphorylcholine, named kocytes from various mammalian species and by macrophages, a with under immunological and nonimmunological stimuli (1-7). lyso-PAF-acether, produced compound biological ac- PAF was also shown to originate from platelets themselves tivity and chromatogrAphical behavior indistinguishable from during aggregation provoked by the ionophore A 23187 (8). those of the native PAF-acether. We also demonstrate here the Structural analysis of purified PAF preparations led, in 1977, potential of chemical ionization (CI) mass spectrometry for to postulation of a phospholipidic structure for PAF, unique structural determination of phospholipids. among the mediators of anaphylaxis (9). The low availability of PAF precluded its structural study by the currently used MATERIALS AND METHODS methods. Some insight into the structure of PAF nevertheless Chemicals. 1-O-Hexadecyl-rac-glycerol 3-phosphoryl- was gained by using different lipases and specific chemical choline (I; n = 14) was purchased from Medmark (Grfinwald, treatments. The results obtained indicated that PAF was a 2- Munich). RED-Al [NaAlH2(OCH2-CH2-O-CH3)2, 70% in O-acylglyceryl phosphorylcholine not having an ester group benzene] was supplied by Aldrich (Beerse, Belgium). 1-0- at position 1 (9, 10). Octadecyl-2-OAcglyceryl 3-phosphorylcholine (II; n = 16), The absence of a hydroxyl group at position 1 was evidenced 1-0-octadecyl-rac-glycerol (III; n = 16), and its isopropylidene by lack of effect of attempted acetylation of highly purified derivative (IV; n = 16) were gifts of J. J. Godfroid (Universit6 PAF preparations on either the activity or the chromatogra- Paris VII). phical behavior of PAF (10). During these experiments it was Release of PAF-Acether and Lyso-PAF-Acether. Purifi- discovered that acetylation of partially purified PAF gave rise cation of hog blood leukocytes and extraction of the released to a significant increase in PAF activity and that the increased lipids were detailed elsewhere (2, 9, 10). Briefly, leukocytes activity was maintained after thorough purification. This ob- were purified by differential centrifugations and washings and servation suggested that a "precursor" of PAF was present in then incubated for 18 hr at pH 9.5. The chloroform-soluble this preparation and that the ester function present in PAF lipids extracted from leukocyte supernatants were then frac- might be an acetate group. This led to the partial synthesis of tionated by silicic acid column chromatography and by high- a highly active platelet-activating component possessing the pressure liquid chromatography (HPLC) (9, 10). The publication costs of this article were defrayed in part by page Abbreviations: PAF, platelet-activating factor; lyso-, devoid of an acyl charge payment. This article must therefore be hereby marked "ad- group; HPLC, high-pressure liquid chromatography; TLC, thin-layer vertisement" in accordance with 18 U. S. C. §1734 solely to indicate chromatography; CI, chemical ionization; EI, electron impact; amu, this fact. atomic mass units; PtdCho, phosphatidylcholine. 7019 Downloaded by guest on October 1, 2021 7020 Biochemistry: Polonsky et al. Proc. Nati. Acad. Sci. USA 77 (1980) Bioassay. Assay for platelet aggregation was performed on of diluted sulfuric acid to the cooled solution. III was purified washed rabbit platelets as described (9, 10). PAF activity was by preparative TLC in methylene dichloride/methanol, 95:5 expressed in arbitrary units; 1 unit is the amount, in Al, of me- (vol/vol), and eluted from the silica gel with methylene di- dium necessary for 50% of the maximum aggregation induced chloride/ethanol, 90/10 (vol/vol). III (n = 14) w'as prepared by thrombin at 0.1 unit/ml. in the same manner from 9.3 mg of I (n = 14). The isopropyl- Chromatographic, Spectroscopic, and Chemical Proce- idene derivatives (IV) were prepared by treatment of the cor- dures. Thin-layer chromatography (TLC) of phospholipids was responding 1-O-alkylglycerols with 2,2-dimethoxypropane and performed on silica gel 60 F 254 plates (Merck, Darmstadt, p-toluenesulfonic acid in benzene for 1.5 hr. The products were Federal Republic of Germany) in chloroform/methanol/water, isolated by usual work-up and purified by preparative TLC in 70:35:7 (vol/vol); TLC of other products was performed on methylene dichloride/methanol, 96:4 (vol/vol). silica gel F 1500 LS 254 plates (Schleicher & Schuell, Dassel, Mild acidic hydrolysis was carried out by treatment with 10% Federal Republic of Germany) which first were washed with (wt/vol) trichloracetic acid for 30 min at 370C as described by ethanol, acetone, and diethyl ether and heated for 1 hr at 600C. Dawson (15). Catalytic hydrogenation was performed in 95% Detection was by use of iodine vapor, Dittmer or Dragendorff ethanol with platinum oxide as catalyst, for 3 hr, at a hydrogen reagents, or spraying with 50% sulfuric acid followed by pressure of 3 bars. heating. HPLC was conducted on a Varian liquid chromato- Acetylation: Combined fractions bi and b2 of phospholipid graph, model 8500, equipped with a differential refractometer; I (3.5 mg) were mixed with acetic anhydride (0.3 ml) and Micropak Si-5 columns (Varian) 25 cm X 12.7 mm (8 mm inside pyridine (0.3 ml) and kept at 220C for 18 hr. The reagents were diameter) were used and elution was performed with chloro- removed under vacuum and the crude product was purified form/methanol/water, 66:50:5 (vol/vol), at a flow rate of 200 by HPLC. II (n = 14) was prepared in the same manner from ml/hr [at 100 bars (107 Pa)]. synthetic I (n = 14) and had a retention time of 20 min on Infrared spectra were measured in chloroform solutions with HPLC. a Perkin-Elmer 297 spectrophotometer. 1H NMR spectra were obtained with a Cameca spectrometer, and chemical shifts are RESULTS given in ppm with respect to internal Me4Si. Electron impact (EI) mass spectra were recorded on an AEI MS50 instrument. CI Mass Spectrometry of Phospholipids. Failure to obtain CI mass spectra were measured at 200-260'C and a gas (iso- interpretable mass spectra of glycerophospholipids under El butane) pressure of 0.5-0.6 torr (66.6-80.0 Pa) in an AEI MS9 prompted us to undertake an investigation of the use of CI mass spectrometer equipped with a CI source (14). spectrometry for the determination of structure of phospho- Reduction with RED-Al: The reagent (0.5 ml) was added to lipids. Analysis of a large number of nonderivatized glycero- 5 mg of the natural phospholipid (I) dissolved in 1.5 ml of phospholipids and also of sphingomyelin by Cl provided a benzene. The solution was heated at 370C for 1 hr; products substantial amount of structural information. In general, it were recovered by extraction with diethyl ether after addition showed MH+ of low abundance but displayed characteristic CH2 -R I CHOH I "0 x/e R .-CH2'.(CH2)j- CH3 CH2-O P-OCH2- CH2N-Me R =-CO (CH2)ri CH3 : I 2 :Oe0Me b a ion A: cleavage a + 2H ion B: A-H20 or cleavage b CH2 - O-CH2 (CH2)nCH3 CHOH @ O / Me CH2 - (CH2)nCH3 CH2-O=P-OCH2CH2N % O-CH2 Me C CHOH I HS I 0° Me CH2-O- POCH2 CH2NM CH2 -O-CH2 (CH2)n CH3 I OMe Me CHOH _ 0 (B CH2-O =P11 I OMe D s Me aD.1 Me - CH2 =CH- N HO CH2 CH2 N I Me H H M/I 90 m/ 72 FIG.
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