1-O-hexadec-1'-enyl-2-acetyl-sn-glycero-3-phosphocholine and its biological activity.
1-O-Alk-1'-enyl analog of platelet-activating factor (PAF, 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine, alkylacetyl-GPC) was prepared semi-synthetically from choline plasmalogens of beef heart muscle. The main compound was identified mass spectrometrically as 1-hexadec-1'-enyl-2-acetyl-sn-glycero-3-phosphocholine (16:O alk-1'-enylacetyl-GPC, 16:O vinyl form of PAF) and its platelet aggregation activity was about one-fifth of that of the corresponding 16:O alkylacetyl-GPC. The irreversible platelet aggregation activity induced by 5X10(-10) M 16:O alk-1'-enylacetyl-GPC was completely inhibited by 5X10(-7) M CV-3988 and 1X10(-7) M L-652, 731, specific PAF antagonists, and more than 99% of the activity was also lost by acid treatment. The hydrogenated product, alkylacetyl analog, showed quite same activity as that of authentic 16:O alkylacetyl-GPC. The platelets desensitized with 16:O alkylacetyl-GPC and with 16:O alk-1'-enylacetyl-GPC were not aggregated with 5X10(-10) M 16:O alk-1'-enylacetyl-GPC, suggesting that alk-1'-enylacetyl-GPC occupied the same receptor site of alkylacetyl-GPC.
Nakayama
R
R
Department of Medical Chemistry, Kansai Medical School, Osaka, Japan.
Yasuda
K
K
Satouchi
K
K
Saito
K
K
D000818:Animals; D002417:Cattle; D005663:Furans / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D009206:Myocardium / Q000032:analysis; D010742:Phospholipid Ethers / Q000494:pharmacology; D010955:Plasmalogens / Q000378:metabolism; D010972:Platelet Activating Factor / Q000031:analogs & derivatives* / Q000494:pharmacology; D010974:Platelet Aggregation / Q000187:drug effects*
D005663:Furans; D010742:Phospholipid Ethers; D010955:Plasmalogens; D010972:Platelet Activating Factor; C032459:choline plasmalogens; C055475:1-O-hexadec-1'-enyl-2-acetyl-sn-glycero-3-phosphocholine; C037913:CV 3988; C047504:2,5-bis(3,4,5-trimethoxyphenyl)tetrahydrofuran