1-O-十六碳-1'-烯基-2-乙酰基-sn-甘油-3-磷酸胆碱及其生物活性。
1-O-hexadec-1'-enyl-2-acetyl-sn-glycero-3-phosphocholine and its biological activity.
作者信息
Nakayama R, Yasuda K, Satouchi K, Saito K
机构信息
Department of Medical Chemistry, Kansai Medical School, Osaka, Japan.
出版信息
Biochem Biophys Res Commun. 1988 Mar 30;151(3):1256-61. doi: 10.1016/s0006-291x(88)80501-1.
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.
血小板活化因子（PAF，1-O-烷基-2-乙酰基-sn-甘油-3-磷酸胆碱，烷基乙酰基-GPC）的1-O-烯丙基-1'-烯基类似物是由牛心肌的胆碱缩醛磷脂半合成制备的。主要化合物经质谱鉴定为1-十六碳-1'-烯基-2-乙酰基-sn-甘油-3-磷酸胆碱（16:O烯丙基-1'-烯基乙酰基-GPC，PAF的16:O乙烯基形式），其血小板聚集活性约为相应的16:O烷基乙酰基-GPC的五分之一。5×10（-10）M的16:O烯丙基-1'-烯基乙酰基-GPC诱导的不可逆血小板聚集活性被5×10（-7）M的CV-3988和1×10（-7）M的L-652,731（特异性PAF拮抗剂）完全抑制，并且经酸处理后超过99%的活性也丧失。氢化产物，即烷基乙酰基类似物，表现出与正宗的16:O烷基乙酰基-GPC相当的活性。用16:O烷基乙酰基-GPC和16:O烯丙基-1'-烯基乙酰基-GPC脱敏的血小板不会被5×10（-10）M的16:O烯丙基-1'-烯基乙酰基-GPC聚集，这表明烯丙基-1'-烯基乙酰基-GPC占据了烷基乙酰基-GPC的相同受体位点。
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