✦ LIBER ✦

Synthesis and polymorphic phase behaviour of polyunsaturated phosphatidylcholines and phosphatidylethanolamines

✍ Scribed by C.J. Dekker; W.S.M. Geurts van Kessel; J.P.G. Klomp; J. Pieters; B. De Kruijff

Publisher: Elsevier Science
Year: 1983
Tongue: English
Weight: 833 KB
Volume: 33
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(83)90012-9

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✦ Synopsis

A series of phosphatidylcholines and phosphatidylethanolamines was synthesized containing two acyl chains of the following polyunsaturated fatty acids: linoleic acid (18:2), linolenic acid (18:3), arachidonic acid (20:4) and docosahexaenoic acid (22:6). In addition two phospholipids with mixed acid composition were synthesized: 16:0/18:1 c phosphatidylcholine and 16:0/18:1 c phosphatidylethanolamine. The structural properties of these lipids in aqueous dispersions in the absence and in the presence of equimolar cholesterol were studied using 3~P-NMR, freeze fracturing and differential scanning calorimetry (DSC).

The phosphatidylcholines adopt a bllayer configuration above 0°C. Incorporation of 50 mol% of cholesterol in polyunsaturated species induces a transition at elevated temperatures into structures with 3~P-NMR characteristics typical of non-bilayer organizations. When the acyl chains contain three or more double bonds, this non-bilayer organization is most likely the hexagonal HII phase. 16:0/18:1 c phosphatidylethanolamine shows a bilayer to hexagonal transition temperature of 75°C. The polyunsaturated phosphatidylethanolamines exhibit a bilayer to hexagonal transition temperature below 0°C which decreases with increasing unsaturation and which is lowered by approximately 10°C upon incorporation of 50 mol% of cholesterol. Finally, it was found that small amounts of polyunsaturated fatty acyl chains in a phosphatidylethanolamine disproportionally lower its bilayer to hexagonal transition temperature.

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