Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties

M.G.J. Balvers, K.C.M. Verhoeckx, P. Plastina, H.M. Wortelboer, J. Meijerink, R.F. Witkamp

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

n-3 PUFAs have beneficial health effects which are believed to be partly related to their anti-inflammatory properties, however the exact mechanisms behind this are unknown. One possible explanation could be via their conversion to N-acyl ethanolamines (NAEs), which are known to possess anti-inflammatory properties. Using fatty acid precursors we showed that 3T3-L1 adipocytes are indeed able to convert docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) to their NAE derivatives docosahexaenoyl ethanolamine (DHEA) and eicosapentaenoyl ethanolamine (EPEA), respectively. This synthesis took place on top of an apparent background formation of these NAEs in standard culture medium. In addition we were able to demonstrate the presence of DHEA, but not of EPEA, in human plasma. DHEA and EPEA were found to decrease LPS induced adipocyte IL-6 and MCP-1 levels. Results of combined incubations with PPAR-¿ and CB2 antagonists suggest a role of these receptors in mediating the reduction of IL-6 by DHEA. Our results are in line with the hypothesis that in addition to other pathways, formation of N-acyl ethanolamines may contribute to the biological activity of n-3 PUFAs. Different targets, including the endocannabinoid system, may be involved in the immune-modulating activity of these “fish-oil-derived NAEs.”
Original languageEnglish
Pages (from-to)1107-1114
JournalBiochimica et Biophysica Acta. Molecular and Cell Biology of Lipids
Volume1801
Issue number10
DOIs
Publication statusPublished - 2010

Fingerprint

Ethanolamines
Ethanolamine
Eicosapentaenoic Acid
Docosahexaenoic Acids
Adipocytes
Anti-Inflammatory Agents
Omega-3 Fatty Acids
Interleukin-6
Endocannabinoids
Peroxisome Proliferator-Activated Receptors
Fish Oils
Culture Media
Fatty Acids

Keywords

  • n-3 fatty-acids
  • insulin-resistance
  • cannabinoid receptor
  • endocannabinoids
  • system
  • cyclooxygenases
  • inflammation
  • macrophages
  • activation
  • anandamide

Cite this

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title = "Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties",
abstract = "n-3 PUFAs have beneficial health effects which are believed to be partly related to their anti-inflammatory properties, however the exact mechanisms behind this are unknown. One possible explanation could be via their conversion to N-acyl ethanolamines (NAEs), which are known to possess anti-inflammatory properties. Using fatty acid precursors we showed that 3T3-L1 adipocytes are indeed able to convert docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) to their NAE derivatives docosahexaenoyl ethanolamine (DHEA) and eicosapentaenoyl ethanolamine (EPEA), respectively. This synthesis took place on top of an apparent background formation of these NAEs in standard culture medium. In addition we were able to demonstrate the presence of DHEA, but not of EPEA, in human plasma. DHEA and EPEA were found to decrease LPS induced adipocyte IL-6 and MCP-1 levels. Results of combined incubations with PPAR-¿ and CB2 antagonists suggest a role of these receptors in mediating the reduction of IL-6 by DHEA. Our results are in line with the hypothesis that in addition to other pathways, formation of N-acyl ethanolamines may contribute to the biological activity of n-3 PUFAs. Different targets, including the endocannabinoid system, may be involved in the immune-modulating activity of these “fish-oil-derived NAEs.”",
keywords = "n-3 fatty-acids, insulin-resistance, cannabinoid receptor, endocannabinoids, system, cyclooxygenases, inflammation, macrophages, activation, anandamide",
author = "M.G.J. Balvers and K.C.M. Verhoeckx and P. Plastina and H.M. Wortelboer and J. Meijerink and R.F. Witkamp",
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Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties. / Balvers, M.G.J.; Verhoeckx, K.C.M.; Plastina, P.; Wortelboer, H.M.; Meijerink, J.; Witkamp, R.F.

In: Biochimica et Biophysica Acta. Molecular and Cell Biology of Lipids, Vol. 1801, No. 10, 2010, p. 1107-1114.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties

AU - Balvers, M.G.J.

AU - Verhoeckx, K.C.M.

AU - Plastina, P.

AU - Wortelboer, H.M.

AU - Meijerink, J.

AU - Witkamp, R.F.

PY - 2010

Y1 - 2010

N2 - n-3 PUFAs have beneficial health effects which are believed to be partly related to their anti-inflammatory properties, however the exact mechanisms behind this are unknown. One possible explanation could be via their conversion to N-acyl ethanolamines (NAEs), which are known to possess anti-inflammatory properties. Using fatty acid precursors we showed that 3T3-L1 adipocytes are indeed able to convert docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) to their NAE derivatives docosahexaenoyl ethanolamine (DHEA) and eicosapentaenoyl ethanolamine (EPEA), respectively. This synthesis took place on top of an apparent background formation of these NAEs in standard culture medium. In addition we were able to demonstrate the presence of DHEA, but not of EPEA, in human plasma. DHEA and EPEA were found to decrease LPS induced adipocyte IL-6 and MCP-1 levels. Results of combined incubations with PPAR-¿ and CB2 antagonists suggest a role of these receptors in mediating the reduction of IL-6 by DHEA. Our results are in line with the hypothesis that in addition to other pathways, formation of N-acyl ethanolamines may contribute to the biological activity of n-3 PUFAs. Different targets, including the endocannabinoid system, may be involved in the immune-modulating activity of these “fish-oil-derived NAEs.”

AB - n-3 PUFAs have beneficial health effects which are believed to be partly related to their anti-inflammatory properties, however the exact mechanisms behind this are unknown. One possible explanation could be via their conversion to N-acyl ethanolamines (NAEs), which are known to possess anti-inflammatory properties. Using fatty acid precursors we showed that 3T3-L1 adipocytes are indeed able to convert docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) to their NAE derivatives docosahexaenoyl ethanolamine (DHEA) and eicosapentaenoyl ethanolamine (EPEA), respectively. This synthesis took place on top of an apparent background formation of these NAEs in standard culture medium. In addition we were able to demonstrate the presence of DHEA, but not of EPEA, in human plasma. DHEA and EPEA were found to decrease LPS induced adipocyte IL-6 and MCP-1 levels. Results of combined incubations with PPAR-¿ and CB2 antagonists suggest a role of these receptors in mediating the reduction of IL-6 by DHEA. Our results are in line with the hypothesis that in addition to other pathways, formation of N-acyl ethanolamines may contribute to the biological activity of n-3 PUFAs. Different targets, including the endocannabinoid system, may be involved in the immune-modulating activity of these “fish-oil-derived NAEs.”

KW - n-3 fatty-acids

KW - insulin-resistance

KW - cannabinoid receptor

KW - endocannabinoids

KW - system

KW - cyclooxygenases

KW - inflammation

KW - macrophages

KW - activation

KW - anandamide

U2 - 10.1016/j.bbalip.2010.06.006

DO - 10.1016/j.bbalip.2010.06.006

M3 - Article

VL - 1801

SP - 1107

EP - 1114

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 -