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Biosynthesis and Fate of Endocannabinoids

  • Chapter
Endocannabinoids

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 231))

Abstract

Since the discovery of the two cannabinoid receptors, CB1 and CB2, several molecules, commonly defined as endocannabinoids, able to bind to and functionally activate these receptors, have been discovered and characterized. Although the general thought was that the endocannabinoids were mainly derivatives of the n-6 fatty acid arachidonic acid, recent data have shown that also derivatives (ethanolamides) of n-3 fatty acids may be classified as endocannabinoids. Whether the n-3 endocannabinoids follow the same biosynthetic and metabolic routes of the n-6 endocannabinoids is not yet clear and so warrants further investigation. In this review, we describe the primary biosynthetic and metabolic pathways for the two well-established endocannabinoids, anandamide and 2-arachidonoylglycerol.

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Abbreviations

2-AG:

2-Arachidonoylglycerol

2-AGE:

2-Arachidonoylglyceryl ether

AA:

Arachidonic acid

Abh4:

Alpha/beta hydrolase 4

ABHD:

Alpha/beta hydrolase domain

AEA:

Anandamide

Asp:

Aspartic acid

CB:

Cannabinoid

Cis:

Cysteine

COX-2:

Cyclooxygenase-2

DAG:

Diacylglycerol

DGL:

Diacylglycerol lipase

DHA:

Docosahexaenoic acid

DHEA:

Docosahexaenoyl-ethanolamide

DTT:

Dithiothreitol

EMT:

Endocannabinoid membrane transporter

EPA:

Eicosapentaenoic acid

EPEA:

Eicosapentaenoyl-ethanolamide

FAAH:

Fatty acid amide hydrolase

FABP:

Fatty acid binding protein

FLAT:

FAAH-like anandamide transporter

GpAEA:

Glycerophospho-arachidonoylethanolamide

GPR:

G-protein coupled receptor

GSH:

Glutathione

HEK:

Human embryonic kidney

His:

Histidine

Hsp:

Heat shock protein

LOX:

Lipoxygenase

Lys:

Lysine

MAFP:

Methylarachidonoylfluorophosphonate

MGL:

Monoacylglycerol lipase

NAAA:

N-acylethanolamine-selective acid amidase

NADA:

N-arachidonoyldopamine

NAE:

N-acyl-ethanolamine

NAGly:

N-arachidonoylglycine

NAM:

N-arachidonoylmaleimide

NAPE:

N-acylphosphatidylethanolamine

NArS:

N-arachidonoylserine

NAT:

N-acyltransferase

OEA:

Oleoyethanolamide

OLDA:

N-oleoyl dopamine

pAEA:

Phosphoanandamide

PE:

Phosphatidylethanolamine

PEA:

Palmitoylethanolamide

PHARC:

Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, cataract

PL:

Phospholipase

PPAR:

Peroxisome proliferator-activated receptor

PUFA:

Polyunsaturated fatty acid

SEA:

Stearoylethanolamide

Ser:

Serine

TRPM:

Transient receptor potential melastatin

TRPV:

Transient receptor potential vanilloid

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  1. School of Medical Sciences, Institute of Medical Sciences, University of Aberdeen, Foresterhill, Aberdeen, AB25 2ZD, Scotland, UK

    Maria Grazia Cascio & Pietro Marini

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  1. Maria Grazia Cascio
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  2. Pietro Marini
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Correspondence to Maria Grazia Cascio .

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  1. Professor of Neuropharmacology, University of Aberdeen Institute of Medical Sciences, Aberdeen, United Kingdom

    Roger G. Pertwee

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Cascio, M.G., Marini, P. (2015). Biosynthesis and Fate of Endocannabinoids. In: Pertwee, R. (eds) Endocannabinoids. Handbook of Experimental Pharmacology, vol 231. Springer, Cham. https://doi.org/10.1007/978-3-319-20825-1_2

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