2001
DOI: 10.1074/jbc.m105854200
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Metabolism of Prostaglandin Glycerol Esters and Prostaglandin Ethanolamides in Vitro and in Vivo

Abstract: Prostaglandin glycerol esters (PG-Gs) and prostaglandin ethanolamides (PG-EAs) are generated by the action of cyclooxygenase-2 on the endocannabinoids 2-arachidonylglycerol (2-AG) and arachidonylethanolamide, respectively. These novel eicosanoids may have unique pharmacological properties and/or serve as latent sources of prostaglandins at sites remote from their tissue of origin. Therefore, we investigated the metabolism of PG-Gs and PG-EAs in vitro and in vivo. PGE 2 -G was rapidly hydrolyzed in rat plasma t… Show more

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Cited by 126 publications
(120 citation statements)
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“…These metabolites are rather stable to further metabolism, except for prostamide E 2 that undergoes slow dehydration/isomerization to prostamide B 2 (Kozak et al, 2001). Prostaglandin E 2 glyceryl ester is rapidly hydrolyzed in rat, but not in human, plasma (Kozak et al, 2001). Regarding lipoxygenase products of AEA and 2-AG, these are formed with both 12-and 15-, but not so easily with 5-, lipoxygenases (Kozak & Marnett, 2002a;van der Stelt et al, 2002).…”
Section: De Petrocellis Et Almentioning
confidence: 99%
See 1 more Smart Citation
“…These metabolites are rather stable to further metabolism, except for prostamide E 2 that undergoes slow dehydration/isomerization to prostamide B 2 (Kozak et al, 2001). Prostaglandin E 2 glyceryl ester is rapidly hydrolyzed in rat, but not in human, plasma (Kozak et al, 2001). Regarding lipoxygenase products of AEA and 2-AG, these are formed with both 12-and 15-, but not so easily with 5-, lipoxygenases (Kozak & Marnett, 2002a;van der Stelt et al, 2002).…”
Section: De Petrocellis Et Almentioning
confidence: 99%
“…Cyclooxygenase-2, and subsequent action of the various prostaglandin synthases, transforms AEA and 2-AG into the corresponding prostaglandin ethanolamides (or prostamides) and prostaglandin glyceryl esters, which, in some assays, exhibit high potency even though they have no activity on either cannabinoid or prostanoid receptors (Woodward et al, 2001;Ross et al, 2002). These metabolites are rather stable to further metabolism, except for prostamide E 2 that undergoes slow dehydration/isomerization to prostamide B 2 (Kozak et al, 2001). Prostaglandin E 2 glyceryl ester is rapidly hydrolyzed in rat, but not in human, plasma (Kozak et al, 2001).…”
Section: De Petrocellis Et Almentioning
confidence: 99%
“…1. AEA and 2-AG can be also oxidized by cyclooxygenase-2, different lipoxygenase isozymes, as well as by cytochrome P450, to generate, respectively, prostaglandin-ethanolamides [15] and prostaglandin-glyceryl esters [16], hydroxy-anandamides and hydroxyleicosatetraenoylglycerols [17], and epoxy-eicosatrienoyl-glycerols [18].…”
Section: The Endocannabinoid Systemmentioning
confidence: 99%
“…Reaction mixtures containing both COX-2 and PGDS were treated with either arachidonic acid or 2-AG at concentrations ranging from 0 to 20 M. Reactions were incubated at room temperature for 0 -5 min. To obtain a common chemical moiety for mass spectrometric analysis, namely the free acid PGD 2 , reaction products were treated with rat plasma, which contains a very active glycerol ester hydrolase (17). PGDS catalyzed the isomerization of both PGH 2 and PGH 2 -G to D-series prostanoids in a time-and concentration-dependent manner (Fig.…”
Section: Endocannabinoid-derived Prostanoids Of the D-series-pgdmentioning
confidence: 99%
“…MeOH and water were removed in vacuo, and residues were taken up in 25 l of Me 2 SO and vigorously vortexed. Fresh, frozen rat plasma was then added to effect ester hydrolysis (final volume of 300 l) as previously described (17). Plasma-treated samples were incubated for 20 min at 37°C.…”
mentioning
confidence: 99%