Enzymatic synthesis of anandamide, an endogenous cannabinoid receptor ligand, through N-acylphosphatidylethanolamine pathway in testis: involvement of Ca(2+)-dependent transacylase and phosphodiesterase activities.
Rat testis was shown to contain significant amounts of both N-acylethanolamine, including N-arachidonoylethanolamine (anandamide), and N-acylphosphatidylethanolamine (N-acylPE), including N-arachidonoylPE. The fatty acid profiles of the N-acyl moieties of the two classes resembled each other. We confirmed that testis microsomes contain a phosphodiesterase activity catalyzing the release of anandamide from N-arachidonoylPE. They also contain an enzyme activity catalyzing the transfer of arachidonic acid from the 1-position of diacylphospholipids to PE to form N-arachidonoylPE. These results suggest that the N-acylPE pathway is important in the synthesis of anandamide in this tissue.
Sugiura
T
T
Faculty of Pharmaceutical Sciences, Teikyo University, Kanagawa, Japan.
Kondo
S
S
Sukagawa
A
A
Tonegawa
T
T
Nakane
S
S
Yamashita
A
A
Waku
K
K
D000217:Acyltransferases / Q000378:metabolism*; D000818:Animals; D016718:Arachidonic Acid / Q000378:metabolism; D001095:Arachidonic Acids / Q000096:biosynthesis*; D002118:Calcium / Q000494:pharmacology*; D002186:Cannabinoids / Q000096:biosynthesis; D063388:Endocannabinoids; D007700:Kinetics; D008297:Male; D008861:Microsomes / Q000201:enzymology*; D010714:Phosphatidylethanolamines / Q000378:metabolism*; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism*; D053284:Polyunsaturated Alkamides; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug / Q000378:metabolism*; D013379:Substrate Specificity; D013737:Testis / Q000378:metabolism*
D001095:Arachidonic Acids; D002186:Cannabinoids; D063388:Endocannabinoids; D010714:Phosphatidylethanolamines; D053284:Polyunsaturated Alkamides; D043882:Receptors, Cannabinoid; D011955:Receptors, Drug; D016718:Arachidonic Acid; D000217:Acyltransferases; D010727:Phosphoric Diester Hydrolases; D002118:Calcium; C078814:anandamide