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2 results on '"20:35,11,14-endocannabinoids"'

1. Novel CB1-ligands maintain homeostasis of the endocannabinoid system in ω3- and ω6-long-chain-PUFA deficiency

Author

Andreas Thomas, Dilyana Filipova, Inga Schmidt-Soltau, Wilhelm Stoffel, Ina Hammels, Symeon Papadopoulos, Matthias Vogel, Britta Jenke, Erika Binczek, and Mario Thevis

Subjects
Fatty Acid Desaturases, 0301 basic medicine, Cannabinoid receptor, FADS2, 20:35,11,14-endocannabinoids, diet effects, surrogate cannabinoid receptor 1 ligands, QD415-436, 030204 cardiovascular system & hematology, Biochemistry, Energy homeostasis, Receptor, Cannabinoid, CB2, Mice, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, Endocrinology, Receptor, Cannabinoid, CB1, Fatty Acids, Omega-6, lipid metabolism, ω3 fatty acids, Fatty Acids, Omega-3, arachidonic acid, Animals, Humans, Research Articles, Mice, Knockout, chemistry.chemical_classification, biology, endocannabinoid system-orexin-circuitry, food and beverages, Cell Biology, Lipid signaling, polyunsaturated fatty acid, Endocannabinoid system, Cell biology, cannabinoid receptor 1, HEK293 Cells, 030104 developmental biology, Fatty acid desaturase, chemistry, biology.protein, fatty acid desaturase 2-deficient mouse model, lipids (amino acids, peptides, and proteins), Arachidonic acid, Endocannabinoids, Polyunsaturated fatty acid
Abstract

Mammalian ω3- and ω6-PUFAs are synthesized from essential fatty acids (EFAs) or supplied by the diet. PUFAs are constitutive elements of membrane architecture and precursors of lipid signaling molecules. EFAs and long-chain (LC)-PUFAs are precursors in the synthesis of endocannabinoid ligands of Gi/o protein-coupled cannabinoid receptor (CB)1 and CB2 in the endocannabinoid system, which critically regulate energy homeostasis as the metabolic signaling system in hypothalamic neuronal circuits and behavioral parameters. We utilized the auxotrophic fatty acid desaturase 2-deficient (fads2−/−) mouse, deficient in LC-PUFA synthesis, to follow the age-dependent dynamics of the PUFA pattern in the CNS-phospholipidome in unbiased dietary studies of three cohorts on sustained LC-PUFA-free ω6-arachidonic acid- and DHA-supplemented diets and their impact on the precursor pool of CB1 ligands. We discovered the transformation of eicosa-all cis-5,11,14-trienoic acid, uncommon in mammalian lipidomes, into two novel endocannabinoids, 20:35,11,14-ethanolamide and 2-20:35,11,14-glycerol. Their function as ligands of CB1 has been characterized in HEK293 cells. Labeling experiments excluded Δ8-desaturase activity and proved the position specificity of FADS2. The fads2−/− mutant might serve as an unbiased model in vivo in the development of novel CB1 agonists and antagonists.

Published
2019
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2. Novel CB1-ligands maintain homeostasis of the endocannabinoid system in ω3- and ω6-long-chain-PUFA deficiency.

Author

Hammels I, Binczek E, Schmidt-Soltau I, Jenke B, Thomas A, Vogel M, Thevis M, Filipova D, Papadopoulos S, and Stoffel W

Subjects
Animals, Endocannabinoids genetics, Fatty Acid Desaturases deficiency, Fatty Acids, Omega-3 pharmacology, Fatty Acids, Omega-6 pharmacology, HEK293 Cells, Humans, Mice, Mice, Knockout, Receptor, Cannabinoid, CB1 genetics, Receptor, Cannabinoid, CB1 metabolism, Receptor, Cannabinoid, CB2 agonists, Receptor, Cannabinoid, CB2 genetics, Receptor, Cannabinoid, CB2 metabolism, Endocannabinoids metabolism, Fatty Acids, Omega-3 deficiency, Fatty Acids, Omega-6 deficiency, Receptor, Cannabinoid, CB1 agonists
Abstract

Mammalian ω3- and ω6-PUFAs are synthesized from essential fatty acids (EFAs) or supplied by the diet. PUFAs are constitutive elements of membrane architecture and precursors of lipid signaling molecules. EFAs and long-chain (LC)-PUFAs are precursors in the synthesis of endocannabinoid ligands of G i/o protein-coupled cannabinoid receptor (CB)1 and CB2 in the endocannabinoid system, which critically regulate energy homeostasis as the metabolic signaling system in hypothalamic neuronal circuits and behavioral parameters. We utilized the auxotrophic fatty acid desaturase 2-deficient ( fads2 -/- ) mouse, deficient in LC-PUFA synthesis, to follow the age-dependent dynamics of the PUFA pattern in the CNS-phospholipidome in unbiased dietary studies of three cohorts on sustained LC-PUFA-free ω6-arachidonic acid- and DHA-supplemented diets and their impact on the precursor pool of CB1 ligands. We discovered the transformation of eicosa-all cis -5,11,14-trienoic acid, uncommon in mammalian lipidomes, into two novel endocannabinoids, 20:3 5,11,14 -ethanolamide and 2-20:3 5,11,14 -glycerol. Their function as ligands of CB1 has been characterized in HEK293 cells. Labeling experiments excluded Δ8-desaturase activity and proved the position specificity of FADS2. The fads2 -/- mutant might serve as an unbiased model in vivo in the development of novel CB1 agonists and antagonists., (Copyright © 2019 Hammels et al. Published by The American Society for Biochemistry and Molecular Biology, Inc.)

Published
2019
Full Text
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