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Journal of Lipid Research, Vol. 48, 2255-2263, October 2007
Copyright © 2007 by American Society for Biochemistry and Molecular Biology

The acylation of lipophilic alcohols by lysosomal phospholipase A₂

Akira Abe^*, Miki Hiraoka and James A. Shayman^1,*

^* Nephrology Division, Department of Internal Medicine, University of Michigan, Ann Arbor, MI 48109
Department of Opthamology, Nippon Medical School, Sendagi, Bunkyo-ku, Tokyo

Published, JLR Papers in Press, July 12, 2007.

¹ To whom correspondence should be addressed. e-mail: jshayman{at}umich.edu

A novel lysosomal phospholipase A₂ (LPLA2) with specificity toward phosphatidylethanolamine and phosphatidylcholine was previously purified and cloned. LPLA2 transfers sn-1 or sn-2 acyl groups of phospholipids to the C1 hydroxyl of the short-chain ceramide N-acetylsphingosine (NAS) under acidic conditions. The common features of lipophilic alcohols serving as acceptor molecules in the transacylase reaction were examined. 1-O-Hexadecyl-2-acetyl-sn-glycerol (HAG) was acylated by LPLA2 similar to NAS. HAG competed with NAS and inhibited NAS acylation. The transacylation of 1-O-hexadecyl-glycerol (HG), 1-O-palmityl-2-O-methyl-sn-glycerol (PMG), and monoacylglycerols was also investigated. HG, PMG, 1- or 3-palmitoyl-sn-glycerol, and 2-palmitoylglycerol were converted to 1,3-alkylacylglycerol, 1,2-dialkyl-3-acylglycerol, 1,3-diacylglycerol, and 1,2- or 2,3-diacylglycerol, respectively. HG and monoacylglycerol inhibited the acylation of NAS by the enzyme with IC₅₀ values of 35 and 45 µM, respectively. Additionally, the enzyme acylated glycerol to produce 1- or 3-acyl-sn-glycerol but not 2-acylglycerol. Therefore, the preferred acceptor molecules for LPLA2 are primary alcohols with one long carbon chain and one small nonpolar residue linked to the C2 position of ethanol. The enzyme acylated other natural lipophilic alcohols, including anandamide and oleoylethanolamide. Thus, LPLA2 may function to remodel acyl groups and modulate the biological and pharmacological activities of some lipophilic alcohols.

Supplementary key words N-acetylsphingosine • ceramide • anandamide • 1-O-hexadecyl-2-acetyl-sn-glycerol • D-threo-1-phenyl-2-decanoylamino-3-morpholino-propanol • amiodarone

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