Rate of acyl migration in lysophosphatidylcholine (LPC) is dependent upon the nature of the acyl group. Greater stability of sn-2 docosahexaenoyl LPC compared to the more saturated LPC species.
Rate of acyl migration in lysophosphatidylcholine (LPC) is dependent upon the nature of the acyl group. Greater stability of sn-2 docosahexaenoyl LPC compared to the more saturated LPC species.
复制标题
DOI：
10.1371/journal.pone.0187826
复制
发表时间：
2017
期刊：
影响因子：
3.7
通讯作者：
Subbaiah PV
中科院分区：
文献类型：
--
作者：
Sugasini D;Subbaiah PV
以前的一些研究报道了sn-2酰基溶血磷脂酰胆碱(LPCS)由于酰基迁移而发生快速异构化，特别是在生理pH和温度下。然而，这些研究大多是使用sn-2棕榈酸酯LPC进行的，而自然产生的sn-2 LPC主要是不饱和的。在本研究中，我们研究了四种天然存在的sn-2酰基LPCS(sn-2 16：0、sn-2 18：1、sn-2 20：4和sn-2 22：6)在不同温度下在水或有机溶剂中的酰基迁移，并用LC/MS分析了其异构体组成。在37℃、pH 7.4时，水溶液中的酰基迁移速率(从sn-2到sn-1)为16：0 lpC>；18：1 lpC>；20：4 lpC>；22：6 lpC。在此条件下，sn-216：0LPC的异构化速率是sn-222：6的2-5倍。LPCS与血清白蛋白的络合加速了所有物种的酰基迁移，但sn-2 22：6 LPC受白蛋白的影响最小。在较低的温度下(22℃、4℃和-20℃)，迁移率较低，但LPC物种之间的差异仍然存在。所有的sn-2酰基LPCS在有机溶剂(氯仿：甲醇，2：1v/v)中都比较稳定，但在所有温度下，在溶剂中酰基对酰基迁移的影响也很明显。在-20℃的有机溶剂中储存4周，sn-2 22：6LPC的异构化程度约为10%，而sn-2的异构化程度为55%。这些结果表明，sn-2多不饱和LPCS可以在-20℃或更低的温度下保存数天，不会发生明显的异构化。此外，他们还表明，在体内产生的sn-2多不饱和LPCs在生理条件下比先前假设的要稳定得多。
Several previous studies reported that sn-2 acyl lysophosphatidylcholines (LPCs) undergo rapid isomerization due to acyl migration, especially at physiological pH and temperature. However, these studies have been carried out using mostly sn-2 palmitoyl LPC, whereas the naturally occurring sn-2 LPCs are predominantly unsaturated. In this study, we investigated the acyl migration in four naturally occurring sn-2 acyl LPCs (sn-2 16:0, sn-2 18:1, sn-2 20:4, and sn-2 22:6) stored at various temperatures in aqueous or organic solvents, employing LC/MS to analyze the isomer composition. At 37°C and pH 7.4, the order of acyl migration rates (from sn-2 to sn-1) in aqueous buffer was 16:0 LPC> 18:1 LPC> 20:4 LPC> 22:6 LPC. The rate of isomerization of sn-2 16:0 LPC was 2–5 times greater than that of sn-2 22:6 under these conditions. Complexing the LPCs to serum albumin accelerated the acyl migration of all species, but sn-2 22:6 LPC was least affected by the presence of albumin. The migration rates were lower at lower temperatures (22°C, 4°C, and -20°C), but the differences between the LPC species persisted. All the sn-2 acyl LPCs were more stable in organic solvent (chloroform: methanol, 2:1 v/v), but the effect of the acyl groups on acyl migration was evident in the solvent also, at all temperatures. Storage of sn-2 22:6 LPC at -20°C for 4 weeks in the organic solvent resulted in about 10% isomerization, compared to 55% isomerization for sn-2 16:0. These results show that the sn-2 polyunsaturated LPCs can be stored at -20°C or below for several days without appreciable isomerization. Furthermore, they demonstrate that the sn-2 polyunsaturated LPCs generated in vivo are much more stable under physiological conditions than previously assumed.
登录
查看更多内容
DOI：
10.1016/j.plefa.2014.01.005
发表时间：
2015-01-01
影响因子：
3
作者：
Lagarde, M.;Hachem, M.;Guichardant, M.
通讯作者：
Guichardant, M.
影响因子：
4.6
作者：
Sugasini D;Thomas R;Yalagala PCR;Tai LM;Subbaiah PV
通讯作者：
Subbaiah PV
影响因子：
1.9
作者：
Yang P;Belikova NA;Billheimer J;Rader DJ;Hill JS;Subbaiah PV
通讯作者：
Subbaiah PV
影响因子：
2.7
作者：
Nakanishi, Hiroki;Iida, Yasuhiro;Taguchi, Ryo
通讯作者：
Taguchi, Ryo
影响因子：
6.1
作者：
Kielbowicz, Grzegorz;Smuga, Damian;Wawrzenczyk, Czeslaw
通讯作者：
Wawrzenczyk, Czeslaw