Biologically active ether lipids. Biotransformation of rac-1(3)-O-alkylglycerols in cell suspension cultures of rape and semisynthesis of 1-O-alkyl-2-palmitoyl-sn-glycero-3-phospho-(N-palmitoyl)ethanolamines, potent antitumor agents.
Biotransformation of rac-1(3)-O-hexadecylglycerol by photomixotrophic rape (Brassica napus) cells in suspension culture leads to 1-O-hexadecyl-2-acyl-sn-glycero-3-phosphocholines and small proportions of other ether lipids, e.g. 1-O-hexadecyl-2-acyl-sn-glycero-3-phosphoethanolamines. Reaction of the hexadecylacyl-glycerophosphocholines with ethanolamine in the presence of phospholipase D from Streptomyces chromofuscus yields additional hexadecylacylglycerophosphoethanolamines. Partial hydrolysis of the combined hexadecylacylglycerophosphoethanolamines followed by reacylation of the resulting lyso compound with palmitic anhydride gives 1-O-hexadecyl-2-palmitoyl-sn-glycero-3-phospho-(N-palmitoyl) ethanolamine, a nontoxic ether glycerophospholipid with antitumor activity. The corresponding 1-O-tetradecyl,1-O-octadecyl, and 1-O-[(Z)-9'-octadecnyl] derivatives are prepared similarly.
Apte
S S
SS
Bundesanstalt für Fettforschung, H.P. Kaufmann Institut, Münster, FRG.
Weber
N
N
Mangold
H K
HK
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001711:Biotransformation; D001937:Brassica / Q000378:metabolism*; D002478:Cells, Cultured; D005995:Glyceryl Ethers / Q000138:chemical synthesis / Q000378:metabolism*; D007202:Indicators and Reagents; D010714:Phosphatidylethanolamines / Q000138:chemical synthesis / Q000378:metabolism*; D010739:Phospholipase D / Q000378:metabolism; D013302:Streptomyces / Q000201:enzymology
D000970:Antineoplastic Agents; D005995:Glyceryl Ethers; D007202:Indicators and Reagents; D010714:Phosphatidylethanolamines; D010739:Phospholipase D; C004348:chimyl alcohol