Presence, formation and putative biological activities of N-acyl serotonins, a novel class of fatty-acid derived mediators in the intestinal tract

K.C.M. Verhoeckx, T. Voortman, M.G.J. Balvers, H.F.J. Hendriks, H.M. Wortelboer, R.F. Witkamp

Research output: Contribution to journalArticleAcademicpeer-review

43 Citations (Scopus)

Abstract

Following the discovery of the endocannabinoid arachidonoyl ethanolamide (anandamide) and other N-acyl-ethanolamines, several other compounds have been found in which amino acids or neurotransmitters rather than ethanolamide are linked to fatty acids. Studies have shown that the local availability of fatty acid precursors, which in turn is modulated by dietary intake of lipids, determines the pattern of conjugates formed. Less information is available whether the same might be true for the amines or neurotransmitters involved. We hypothesized that N-arachidonoyl-serotonin (AA-5-HT) and its analogs could be endogenously present in those tissues that have high contents of serotonin. We investigated the endogenous presence of N-acyl serotonins in different parts of the gastro-intestinal tract of pigs and mice. We discovered that AA-5-HT, oleoyl-serotonin, palmitoyl-serotonin, and stearoyl-serotonin were endogenously present, particularly in the jejunum and ileum. Their formation in vitro was stimulated by the addition of serotonin to intestinal tissue incubations. Furthermore, in a mouse study we showed that the pattern of formation is dependent on the relative amount of fatty acids in the diet. The formation of docosahexaenoyl-serotonin and eicosapentaenoyl-serotonin was elevated in mice fed with a diet containing fish oil. Preliminary data showed that several of the serotonin conjugates are able to inhibit glucagon-like peptide-1 secretion and FAAH activity in vitro. Taken together, our data suggest that N-acyl serotonins are a novel class of lipid mediators present in the gut with highly promising biological properties
Original languageEnglish
Pages (from-to)578-586
JournalBiochimica et Biophysica Acta. Molecular and Cell Biology of Lipids
Volume1811
Issue number10
DOIs
Publication statusPublished - 2011

Fingerprint

Serotonin
Fatty Acids
Neurotransmitter Agents
Ethanolamines
Diet
Lipids
Endocannabinoids
Glucagon-Like Peptide 1
Fish Oils
Jejunum
Ileum
Amines
Swine
Amino Acids

Keywords

  • glucagon-like peptide-1
  • rat-brain
  • arachidonoyl-serotonin
  • endocannabinoid inactivation
  • electrospray-ionization
  • quantitative method
  • mass-spectrometry
  • amide hydrolase
  • anandamide
  • analogs

Cite this

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title = "Presence, formation and putative biological activities of N-acyl serotonins, a novel class of fatty-acid derived mediators in the intestinal tract",
abstract = "Following the discovery of the endocannabinoid arachidonoyl ethanolamide (anandamide) and other N-acyl-ethanolamines, several other compounds have been found in which amino acids or neurotransmitters rather than ethanolamide are linked to fatty acids. Studies have shown that the local availability of fatty acid precursors, which in turn is modulated by dietary intake of lipids, determines the pattern of conjugates formed. Less information is available whether the same might be true for the amines or neurotransmitters involved. We hypothesized that N-arachidonoyl-serotonin (AA-5-HT) and its analogs could be endogenously present in those tissues that have high contents of serotonin. We investigated the endogenous presence of N-acyl serotonins in different parts of the gastro-intestinal tract of pigs and mice. We discovered that AA-5-HT, oleoyl-serotonin, palmitoyl-serotonin, and stearoyl-serotonin were endogenously present, particularly in the jejunum and ileum. Their formation in vitro was stimulated by the addition of serotonin to intestinal tissue incubations. Furthermore, in a mouse study we showed that the pattern of formation is dependent on the relative amount of fatty acids in the diet. The formation of docosahexaenoyl-serotonin and eicosapentaenoyl-serotonin was elevated in mice fed with a diet containing fish oil. Preliminary data showed that several of the serotonin conjugates are able to inhibit glucagon-like peptide-1 secretion and FAAH activity in vitro. Taken together, our data suggest that N-acyl serotonins are a novel class of lipid mediators present in the gut with highly promising biological properties",
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author = "K.C.M. Verhoeckx and T. Voortman and M.G.J. Balvers and H.F.J. Hendriks and H.M. Wortelboer and R.F. Witkamp",
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Presence, formation and putative biological activities of N-acyl serotonins, a novel class of fatty-acid derived mediators in the intestinal tract. / Verhoeckx, K.C.M.; Voortman, T.; Balvers, M.G.J.; Hendriks, H.F.J.; Wortelboer, H.M.; Witkamp, R.F.

In: Biochimica et Biophysica Acta. Molecular and Cell Biology of Lipids, Vol. 1811, No. 10, 2011, p. 578-586.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Presence, formation and putative biological activities of N-acyl serotonins, a novel class of fatty-acid derived mediators in the intestinal tract

AU - Verhoeckx, K.C.M.

AU - Voortman, T.

AU - Balvers, M.G.J.

AU - Hendriks, H.F.J.

AU - Wortelboer, H.M.

AU - Witkamp, R.F.

PY - 2011

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AB - Following the discovery of the endocannabinoid arachidonoyl ethanolamide (anandamide) and other N-acyl-ethanolamines, several other compounds have been found in which amino acids or neurotransmitters rather than ethanolamide are linked to fatty acids. Studies have shown that the local availability of fatty acid precursors, which in turn is modulated by dietary intake of lipids, determines the pattern of conjugates formed. Less information is available whether the same might be true for the amines or neurotransmitters involved. We hypothesized that N-arachidonoyl-serotonin (AA-5-HT) and its analogs could be endogenously present in those tissues that have high contents of serotonin. We investigated the endogenous presence of N-acyl serotonins in different parts of the gastro-intestinal tract of pigs and mice. We discovered that AA-5-HT, oleoyl-serotonin, palmitoyl-serotonin, and stearoyl-serotonin were endogenously present, particularly in the jejunum and ileum. Their formation in vitro was stimulated by the addition of serotonin to intestinal tissue incubations. Furthermore, in a mouse study we showed that the pattern of formation is dependent on the relative amount of fatty acids in the diet. The formation of docosahexaenoyl-serotonin and eicosapentaenoyl-serotonin was elevated in mice fed with a diet containing fish oil. Preliminary data showed that several of the serotonin conjugates are able to inhibit glucagon-like peptide-1 secretion and FAAH activity in vitro. Taken together, our data suggest that N-acyl serotonins are a novel class of lipid mediators present in the gut with highly promising biological properties

KW - glucagon-like peptide-1

KW - rat-brain

KW - arachidonoyl-serotonin

KW - endocannabinoid inactivation

KW - electrospray-ionization

KW - quantitative method

KW - mass-spectrometry

KW - amide hydrolase

KW - anandamide

KW - analogs

U2 - 10.1016/j.bbalip.2011.07.008

DO - 10.1016/j.bbalip.2011.07.008

M3 - Article

VL - 1811

SP - 578

EP - 586

JO - Biochimica et Biophysica Acta. Molecular and Cell Biology of Lipids

JF - Biochimica et Biophysica Acta. Molecular and Cell Biology of Lipids

SN - 1388-1981

IS - 10

ER -