Oxygenation of Anandamide by Lipoxygenases

Guus van Zadelhoff; Mario van der Stelt

doi:10.1007/978-1-0716-2728-0_26

Oxygenation of Anandamide by Lipoxygenases

Guus van Zadelhoff, Mario van der Stelt^*

^*Corresponding author for this work

Leiden University

Research output: Chapter in Book/Report/Conference proceeding › Chapter › Academic › peer-review

Abstract

The endocannabinoids anandamide and 2-arachidonoylglycerol are not only metabolized by serine hydrolases, such as fatty acid amide hydrolase, monoacylglycerol lipase, and α,β-hydrolases 6 and 12, but they also serve as substrates for cyclooxygenases, cytochrome P450s, and lipoxygenases. These enzymes oxygenate the 1Z,4Z-pentadiene system of the arachidonic acid backbone of endocannabinoids, thereby giving rise to an entirely new array of bioactive lipids. Hereby, a protocol is provided for the enzymatic synthesis, purification, and characterization of various oxygenated metabolites of anandamide generated by lipoxygenases, which enables the biological study and detection of these metabolites.

Original language	English
Title of host publication	Endocannabinoid Signaling
Subtitle of host publication	Methods and Protocols
Editors	Mauro Maccarrone
Place of Publication	New York
Publisher	Humana Press
Pages	307-316
Number of pages	10
Edition	2
ISBN (Electronic)	978-1-0716-2728-0
ISBN (Print)	978-1-0716-2727-3
DOIs	https://doi.org/10.1007/978-1-0716-2728-0_26
Publication status	Published - 25 Sept 2023

Publication series

Name	Methods in Molecular Biology
Publisher	Humana Press
Volume	2576
ISSN (Print)	1064-3745
ISSN (Electronic)	1940-6029

Bibliographical note

Publisher Copyright:
© 2023, The Author(s), under exclusive license to Springer Science+Business Media, LLC, part of Springer Nature.

Keywords

2-Arachidonoylglycerol
Anandamide
Endocannabinoid
Lipoxygenase
Oxygenated metabolite

Access to Document

10.1007/978-1-0716-2728-0_26

978-1-0716-2728-0_26Final published version, 241 KBLicence: Taverne

Cite this

@inbook{7943614aa32a47129c4b4bd144eb531a,

title = "Oxygenation of Anandamide by Lipoxygenases",

abstract = "The endocannabinoids anandamide and 2-arachidonoylglycerol are not only metabolized by serine hydrolases, such as fatty acid amide hydrolase, monoacylglycerol lipase, and α,β-hydrolases 6 and 12, but they also serve as substrates for cyclooxygenases, cytochrome P450s, and lipoxygenases. These enzymes oxygenate the 1Z,4Z-pentadiene system of the arachidonic acid backbone of endocannabinoids, thereby giving rise to an entirely new array of bioactive lipids. Hereby, a protocol is provided for the enzymatic synthesis, purification, and characterization of various oxygenated metabolites of anandamide generated by lipoxygenases, which enables the biological study and detection of these metabolites.",

keywords = "2-Arachidonoylglycerol, Anandamide, Endocannabinoid, Lipoxygenase, Oxygenated metabolite",

author = "{van Zadelhoff}, Guus and {van der Stelt}, Mario",

note = "Publisher Copyright: {\textcopyright} 2023, The Author(s), under exclusive license to Springer Science+Business Media, LLC, part of Springer Nature.",

year = "2023",

month = sep,

day = "25",

doi = "10.1007/978-1-0716-2728-0_26",

language = "English",

isbn = "978-1-0716-2727-3",

series = "Methods in Molecular Biology",

publisher = "Humana Press",

pages = "307--316",

editor = "Maccarrone, {Mauro }",

booktitle = "Endocannabinoid Signaling",

edition = "2",

}

TY - CHAP

T1 - Oxygenation of Anandamide by Lipoxygenases

AU - van Zadelhoff, Guus

AU - van der Stelt, Mario

PY - 2023/9/25

Y1 - 2023/9/25

N2 - The endocannabinoids anandamide and 2-arachidonoylglycerol are not only metabolized by serine hydrolases, such as fatty acid amide hydrolase, monoacylglycerol lipase, and α,β-hydrolases 6 and 12, but they also serve as substrates for cyclooxygenases, cytochrome P450s, and lipoxygenases. These enzymes oxygenate the 1Z,4Z-pentadiene system of the arachidonic acid backbone of endocannabinoids, thereby giving rise to an entirely new array of bioactive lipids. Hereby, a protocol is provided for the enzymatic synthesis, purification, and characterization of various oxygenated metabolites of anandamide generated by lipoxygenases, which enables the biological study and detection of these metabolites.

AB - The endocannabinoids anandamide and 2-arachidonoylglycerol are not only metabolized by serine hydrolases, such as fatty acid amide hydrolase, monoacylglycerol lipase, and α,β-hydrolases 6 and 12, but they also serve as substrates for cyclooxygenases, cytochrome P450s, and lipoxygenases. These enzymes oxygenate the 1Z,4Z-pentadiene system of the arachidonic acid backbone of endocannabinoids, thereby giving rise to an entirely new array of bioactive lipids. Hereby, a protocol is provided for the enzymatic synthesis, purification, and characterization of various oxygenated metabolites of anandamide generated by lipoxygenases, which enables the biological study and detection of these metabolites.

KW - 2-Arachidonoylglycerol

KW - Anandamide

KW - Endocannabinoid

KW - Lipoxygenase

KW - Oxygenated metabolite

UR - http://www.scopus.com/inward/record.url?scp=85138458400&partnerID=8YFLogxK

U2 - 10.1007/978-1-0716-2728-0_26

DO - 10.1007/978-1-0716-2728-0_26

M3 - Chapter

C2 - 36152198

AN - SCOPUS:85138458400

SN - 978-1-0716-2727-3

T3 - Methods in Molecular Biology

SP - 307

EP - 316

BT - Endocannabinoid Signaling

A2 - Maccarrone, Mauro

PB - Humana Press

CY - New York

ER -

Oxygenation of Anandamide by Lipoxygenases

Abstract

Publication series

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this