Neutral and ionic ether glycerolipids, especially alkylacylglycerophosphocholines and 1
-alkenylacylglycerophosphocholines, are formed from exogenous 1-O-alkylglycerols, 1-O-(1
-alkenyl)glycerols or 2-O-alkylglycerols by photomixotrophic cell suspension cultures of rape (
Brassica napus). Best yields of ether glycerolipids were obtained by incubating rape cells with optically active 1-O-alkyl-sn-glycerols. Racemic or symmetric alkylglycerols are also utilized by rape cell suspension cultures for the biosynthesis of optically active ionic ether glycerolipids. In contrast, 3-O-hexadecyl-sn-glycerol is not incorporated into ether glycerophospholipids of rape cells. Incorporation of the substrates into ionic ether lipids is dependent on chain length (C
14>C
16>C
18) and degree of unsaturation (C
18:1
C
18:0) of alkyl chains.
Stereochemically uniform 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholines and 2-O-alkyl-1-acyl-sn-glycero-3-phosphocholines with defined alkyl moieties can be prepared from exogenous alkylglycerols. This method recommends itself especially for the preparation of 1-O-(1
-alkenyl)-2-acyl-sn-glycero-3-phosphocholines (
choline plasmalogens
) from 1-O-(1
-alkenyl)-sn-glycerols. Ether glycerophospholipids with physiological activity, such as 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholines (platelet activating factor, PAF) and 1-O-alkyl-sn-glycero-3-phosphocholines (lyso PAF), were synthesized from 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholines formed by cell suspension cultures of rape.