Identification of an unusual naturally occurring apolar fatty acid amide in mammalian brain and a method for its quantitative determination

Carbonare, Maurizio Dalle; Tonidandel, L.; Berto, Fiorenzo; Luise, Diego; Mardegan, Andrea; Giordano, Giuseppe; Dalt, Liviana Da; Guiotto, A.; Battistin, Leontino; Leon, Alberta; Traldi, Pietro

doi:10.1002/rcm.2313

Cited by 3 publications

(2 citation statements)

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“…A few examples of mammalian N-acylamides are the acetylated polyamines, the ceramides, and sphingomyleins. The identification of N-stearoylisopropylamine [107] and the phophocholine-NAE conjugates [108] from mouse brain suggests that many other mammalian fatty acid amides await discovery.…”

Section: N-acylamidesmentioning

confidence: 99%

Biosynthesis, degradation and pharmacological importance of the fatty acid amides

Farrell

Merkler

2008

Drug Discovery Today

109

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The identification of two biologically active fatty acid amides, N-arachidonoylethanolamine (anandamide) and oleamide, has generated a great deal of excitement and stimulated considerable research. However, anandamide and oleamide are merely the best-known and best-understood members of a much larger family of biologically-occurring fatty acid amides. In this review, we will outline which fatty acid amides have been isolated from mammalian sources, detail what is known about how these molecules are made and degraded in vivo, and highlight their potential for the development of novel therapeutics. Keywords N-acylamino acid; N-acyldopamine; N-acylethanolamine; primary fatty acid amide; N-acylamideThe fatty acid amide bond has long been recognized in nature, being important in the structure of the ceramides [1] and the sphingolipids [2]. The first non-sphingosine based fatty acid amide isolated from a natural source was N-palmitoylethanolamine from egg yolk in 1957 [3]. Interest in the N-acylethanolamines (NAEs) dramatically increased upon the identification of Narachidonoylethanolamine (anandamide) as the endogenous ligand for the cannabinoid receptors in the mammalian brain [4]. It is now known that a family of NAEs is found in the brain and in other tissues [5,6].In addition to the NAEs, other classes of fatty acid amides have been characterized, namely the N-acylamino acids (NAAs) [7], the N-acyldopamines (NADAs) [8] and the primary fatty acid amides (PFAMs) [9,10] (Figure 1). Relative to NAEs, much less is currently known about the NAAs, the NADAs and the PFAMs, except that they are found in biological systems. The goal of this review is to summarize the current state of knowledge regarding the different classes of endogenous fatty acid amides and highlight their potential for drug discovery (see refs. [11-13] for earlier reviews) © 2008 Elsevier Ltd. All rights reserved.Corresponding author: Merkler, D.J (E-mail: merkler@cas.usf.edu) phone 813-974-3579; fax 813-974-1733. Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.Teaser SentenceFatty acid amides are a family of mammalian bioactive compounds. These molecules and the enzymes involved in their metabolism provide an opportunity to develop new drugs to treat human disease. -palmitoyl-, N-stearoyl-and N-oleoylethanolamine [5,11], each compromising ≥25% of total brain NAEs. Other less abundant NAEs found in the brain are anandamide, N-linoleoyl-, N-linolenoyl-, N-dihomo-γ-linolenoyl-and N-docosatetraenoylethanolamine [11]. In addition to the brain, the NAEs are widespread in the peripheral tissues [5]. The mos...

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Section: N-acylamidesmentioning

confidence: 99%

Biosynthesis, degradation and pharmacological importance of the fatty acid amides

Farrell

Merkler

2008

Drug Discovery Today

109

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“…However, their endogenous formation is at present questionable. A number of different fatty acid amides have recently been found in brain tissues at low concentrations, including oleamide [152,153], Nstearoyl-isopropylamine [154], N-arachidonoyl-serine [155], N-acyl-dopamine [156][157][158][159], N-acyl-GABA [160], and N-acyl-taurine [161]. Some of them have pharmacological activities, but their biological significance is at present uncertain.…”

Section: Endocannabinoids -2-arachidonoylglycerol the Real Endocannamentioning

confidence: 99%

Endocannabinoids

Hansen¹,

Petersen²,

Artmann³

et al. 2006

Eur. J. Lipid Sci. Technol.

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EndocannabinoidsThe endocannabinoid system embraces a group of lipid molecules, enzymes and receptor proteins. This system appears to be involved in the modulation of neurotransmitter release thereby modifying learning and memory, in the regulation of food intake, and in the modulation of inflammation and pain and several other physiological/ pathophysiological conditions. Furthermore, naturally occurring structural analogues of one of the endocannabinoids also appear to have beneficial biological activity in animal models of pain and obesity, although these endogenous compounds cannot activate cannabinoid receptors. The intention of this short review is to give an updated overview of this very large field from a biochemical and pharmacological point of view.

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Current literature in mass spectrometry

2006

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (4 Weeks journals ‐ Search completed at 28th. June 2006)

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Identification of an unusual naturally occurring apolar fatty acid amide in mammalian brain and a method for its quantitative determination

Cited by 3 publications

References 27 publications

Biosynthesis, degradation and pharmacological importance of the fatty acid amides

Biosynthesis, degradation and pharmacological importance of the fatty acid amides

Endocannabinoids

Current literature in mass spectrometry

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