| Biosynthesis and inactivation of N-arachidonoylethanolamine (anandamide) and N-docosahexaenoylethanolamine in bovine retina. | |
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MedLine Citation:
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PMID: 10577359 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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N-Arachidonoylethanolamine (anandamide; AEA) and 2-arachidonoylglycerol (2-AG), the two proposed endogenous agonists of cannabinoid receptors, and the putative AEA biosynthetic precursor, N-arachidonoylphosphatidylethanolamine (NArPE), were identified in bovine retina by means of gas chromatography-electron impact mass spectrometry (GC-EIMS). This technique also allowed us to identify N-docosahexanoylethanolamine (DHEA) and 2-docosahexanoylglycerol (2-DHG), two derivatives of docosahexaenoic acid (DHA), one of the most abundant fatty acids esterified in retina phospholipids and necessary for optimal retinal function. N-Docosahexaenoylphosphatidylethanolamine (NDHPE), the potential biosynthetic precursor for DHEA, was also found. The fatty acid composition of the sn-1 and sn-2 positions of bovine retina's most abundant phospholipid classes, also determined here, were in agreement with a phospholipid-dependent mechanism for 2-AG, 2-DHG, AEA, and DHEA biosynthesis, as very high levels of polyunsaturated fatty acids, including DHA, were found on the sn-2 position of phosphatidylcholine (PC) and -ethanolamine (PE), and measurable amounts of di-docosahexanoyl-PC and -PE, two potential biosynthetic precursors of NDHPE, were detected. Accordingly, we found that isolated particulate fractions from bovine retina could release AEA and DHEA in a time-dependent fashion. Finally, a fatty acid amide hydrolase (FAAH)-like activity with subcellular distribution and pH dependency similar to those reported for the brain enzyme was also detected in bovine retina. This activity was inhibited by FAAH inhibitors, phenylmethylsulfonyl fluoride and arachidonoyltrifluoromethylketone, and appeared to recognize DHEA with a lower efficiency than AEA. These data indicate that AEA and its congeners may play a physiological role in the mammalian eye. |
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Authors:
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T Bisogno; I Delton-Vandenbroucke; A Milone; M Lagarde; V Di Marzo |
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Publication Detail:
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Type: In Vitro; Journal Article |
Journal Detail:
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Title: Archives of biochemistry and biophysics Volume: 370 ISSN: 0003-9861 ISO Abbreviation: Arch. Biochem. Biophys. Publication Date: 1999 Oct |
Date Detail:
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Created Date: 1999-11-08 Completed Date: 1999-11-08 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0372430 Medline TA: Arch Biochem Biophys Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 300-7 Citation Subset: IM |
Affiliation:
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Istituto per la Chimica Molecole di Interesse Biologico, CNR, Arco Felice, Napoli, Italy. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amides
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antagonists & inhibitors*,
metabolism* Amidohydrolases / metabolism Animals Arachidonic Acids / antagonists & inhibitors*, biosynthesis* Cannabinoids / metabolism Cattle Docosahexaenoic Acids / metabolism Ethanolamines / antagonists & inhibitors*, metabolism* Fatty Acids / analysis Gas Chromatography-Mass Spectrometry Glycerides / metabolism Kinetics Phosphatidylcholines / chemistry, metabolism Phosphatidylethanolamines / chemistry, metabolism Polyunsaturated Alkamides Receptors, Cannabinoid Receptors, Drug / agonists Retina / metabolism* |
| Chemical | |
Reg. No./Substance:
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0/Amides; 0/Arachidonic Acids; 0/Cannabinoids; 0/Ethanolamines; 0/Fatty Acids; 0/Glycerides; 0/Phosphatidylcholines; 0/Phosphatidylethanolamines; 0/Polyunsaturated Alkamides; 0/Receptors, Cannabinoid; 0/Receptors, Drug; 25167-62-8/Docosahexaenoic Acids; 53847-30-6/2-arachidonylglycerol; 94421-68-8/anandamide; EC 3.5.-/Amidohydrolases; EC 3.5.1.-/fatty-acid amide hydrolase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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