Influence of alkyl ether chain length of acetyl glyceryl ether phosphorylcholine and its ethanolamine analog on biological activity toward rabbit platelets.
Influence of alkyl ether chain length of acetyl glyceryl ether phosphorylcholine and its ethanolamine analog on biological activity toward rabbit platelets.
复制标题
乙酰甘油醚磷酰胆碱及其乙醇胺类似物的烷基醚链长对兔血小板生物活性的影响。
DOI：
10.1016/0003-9861(81)90504-x
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发表时间：
1981
影响因子：
3.9
通讯作者：
Hanahan,DJ
中科院分区：
文献类型：
--
作者：
Satouchi,K;Pinckard,RN;Hanahan,DJ
利用牛心肌中含有乙烯基醚的卵磷脂（缩醛磷脂）作为起始原料，通过简单的半合成方法制备了一种有效的新型脂质化学介质1-O-烷基-2-乙酰基-sn-甘油基-3-磷酸胆碱（AGEPC），得到了一种具有混合链烷基残基的衍生物。为了更密切地关注AGEPC的各种组分相对于其生物活性的重要性，重要的是开发用于分离富含特定链长的烷基残基的分子的方法。在目前的研究中，人们发现，一个简单的薄层色谱技术，使用甲醇-水（2：1，体积比）的溶剂系统，提供了一个很好的分离半合成AGEPC成两个物种，一个包含超过95摩尔% 16：0和其他95摩尔% 18：0的烷基链物种。同样的程序允许1-O-烷基-2-乙酰基-sn-甘油基-3-磷酰乙醇胺（AGEPE）的物种的相当的分离从AGEPC通过磷脂酶D的作用。基于它们从洗涤的兔血小板中释放5-羟色胺的有效性，AGEPC和AGEPE的16：0-富集衍生物分别比相应的18：0-富集衍生物表现出显著更高的比活性，以摩尔计为3 - 6倍。这些研究结果进行了讨论的重要性的烷基醚基团的链长在AGEPC的生物活性的表达。
The preparation of the potent new lipid chemical mediator, 1-O-alkyl-2-acetyl-sn-glyceryl-3-phosphorylcholine (AGEPC), through a facile semisynthetic procedure utilizing the vinyl ether-containing lecithins (plasmalogens) of bovine heart muscle as the starting material results in a derivative with mixed chain alkyl residues. In order to focus more closely on the importance of the various components of AGEPC relative to its biological activity, it was of importance to develop a method for isolation of molecules rich in a specific chain length of the alkyl residue. In the current study it was found that a simple thin-layer chromatographic technique, using a solvent system of methanol water (2: 1, v v), afforded an excellent separation of semisynthetic AGEPC into two species, one containing over 95 mol% 16: 0 and the other 95 mol% 18: 0 alkyl chain species. The same procedure allowed a comparable separation of the species of 1-O-alkyl-2-acetyl-sn-glyceryl-3-phosphorylethanolamine (AGEPE) prepared from AGEPC by phospholipase D action. On the basis of their effectiveness in releasing serotonin from washed rabbit platelets, the 16: 0-rich derivatives of AGEPC and AGEPE exhibited significantly higher specific activities, from three to six-fold, on a molar basis, respectively, than the corresponding 18: 0-rich derivatives. These findings are discussed in relation to the importance of the chain length of the alkyl ether group in expression of the biological activity of AGEPC.