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

FEBS Lett. 1990 Jun 4;265(1-2):104-6. doi: 10.1016/0014-5793(90)80894-o.

Abstract

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.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Biotransformation
  • Brassica / metabolism*
  • Cells, Cultured
  • Glyceryl Ethers / chemical synthesis
  • Glyceryl Ethers / metabolism*
  • Indicators and Reagents
  • Phosphatidylethanolamines / chemical synthesis
  • Phosphatidylethanolamines / metabolism*
  • Phospholipase D / metabolism
  • Streptomyces / enzymology

Substances

  • Antineoplastic Agents
  • Glyceryl Ethers
  • Indicators and Reagents
  • Phosphatidylethanolamines
  • Phospholipase D
  • chimyl alcohol