Oleic Acid Amides With Potential Pharmacological Effects in the Overweight Treatment

2018 ◽  
Vol 69 (4) ◽  
pp. 790-794
Author(s):  
Catalina Negut ◽  
Lucia Pintilie ◽  
Constantin Tanase ◽  
Denisa Ioana Udeanu ◽  
Constantin Draghici ◽  
...  
Keyword(s):  
Body Weight ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Food Intake ◽  
Nmr Spectra ◽  
Acid Amide ◽  
Pharmacological Effects ◽  
13C Nmr Spectra ◽  
1H And 13C Nmr ◽  
Fatty Acid Amide

Fatty acid amide analogues were synthesized from oleic acid, activated by 1,1�-carbonildiimidazole to oleoylimidazole and amines, and characterized by IR, MS, 1H- and 13C-NMR spectra. The compounds were investigated for their influence on body weight and food-intake effects on an obesity-induced mouse model.

scholarly journals Role for fatty acid amide hydrolase (FAAH) in the leptin-mediated effects on feeding and energy balance

2018 ◽  
Vol 115 (29) ◽  
pp. 7605-7610 ◽  
Author(s):  
Georgia Balsevich ◽  
Martin Sticht ◽  
Nicole P. Bowles ◽  
Arashdeep Singh ◽  
Tiffany T. Y. Lee ◽  
...  
Keyword(s):  
Body Weight ◽  
Fatty Acid ◽  
Food Intake ◽  
Fatty Acid Amide Hydrolase ◽  
Acid Amide ◽  
Endocannabinoid System ◽  
Mediated Effects ◽  
Leptin Sensitivity ◽  
Amide Hydrolase ◽  
Fatty Acid Amide

Endocannabinoid signaling regulates feeding and metabolic processes and has been linked to obesity development. Several hormonal signals, such as glucocorticoids and ghrelin, regulate feeding and metabolism by engaging the endocannabinoid system. Similarly, studies have suggested that leptin interacts with the endocannabinoid system, yet the mechanism and functional relevance of this interaction remain elusive. Therefore, we explored the interaction between leptin and endocannabinoid signaling with a focus on fatty acid amide hydrolase (FAAH), the primary degradative enzyme for the endocannabinoid N-arachidonoylethanolamine (anandamide; AEA). Mice deficient in leptin exhibited elevated hypothalamic AEA levels and reductions in FAAH activity while leptin administration to WT mice reduced AEA content and increased FAAH activity. Following high fat diet exposure, mice developed resistance to the effects of leptin administration on hypothalamic AEA content and FAAH activity. At a functional level, pharmacological inhibition of FAAH was sufficient to prevent leptin-mediated effects on body weight and food intake. Using a novel knock-in mouse model recapitulating a common human polymorphism (FAAH C385A; rs324420), which reduces FAAH activity, we investigated whether human genetic variance in FAAH affects leptin sensitivity. While WT (CC) mice were sensitive to leptin-induced reductions in food intake and body weight gain, low-expressing FAAH (AA) mice were unresponsive. These data demonstrate that FAAH activity is required for leptin’s hypophagic effects and, at a translational level, suggest that a genetic variant in the FAAH gene contributes to differences in leptin sensitivity in human populations.

Assessment of anandamide's pharmacological effects in mice deficient of both fatty acid amide hydrolase and cannabinoid CB1 receptors

2007 ◽  
Vol 557 (1) ◽  
pp. 44-48 ◽  
Author(s):  
Laura E. Wise ◽  
Christopher C. Shelton ◽  
Benjamin F. Cravatt ◽  
Billy R. Martin ◽  
Aron H. Lichtman
Keyword(s):  
Fatty Acid ◽  
Fatty Acid Amide Hydrolase ◽  
Acid Amide ◽  
Cb1 Receptors ◽  
Pharmacological Effects ◽  
Amide Hydrolase ◽  
Fatty Acid Amide

scholarly journals Potential of Fatty Acid Amide Hydrolase (FAAH), Monoacylglycerol Lipase (MAGL), and Diacylglycerol Lipase (DAGL) Enzymes as Targets for Obesity Treatment: A Narrative Review

2021 ◽  
Vol 14 (12) ◽  
pp. 1316
Author(s):  
Justin Matheson ◽  
Xin Ming Matthew Zhou ◽  
Zoe Bourgault ◽  
Bernard Le Foll
Keyword(s):  
Body Weight ◽  
Fatty Acid ◽  
Fatty Acid Amide Hydrolase ◽  
Acid Amide ◽  
Obesity Treatment ◽  
Monoacylglycerol Lipase ◽  
Diacylglycerol Lipase ◽  
Genetic Deletion ◽  
Amide Hydrolase ◽  
Fatty Acid Amide

The endocannabinoid system (ECS) plays an integral role in maintaining metabolic homeostasis and may affect hunger, caloric intake, and nutrient absorption. Obesity has been associated with higher levels of the endogenous cannabinoid transmitters (endocannabinoids). Therefore, the ECS is an important target in obesity treatment. Modulating the enzymes that synthesize and degrade endocannabinoids, namely fatty acid amide hydrolase (FAAH), monoacylglycerol lipase (MAGL), and diacylglycerol lipase (DAGL), may be a promising strategy to treat obesity. This review aims to synthesize all studies investigating pharmacological or genetic manipulation of FAAH, MAGL, or DAGL enzymes in association with obesity-related measures. Pharmacological inhibition or genetic deletion of FAAH tended to promote an obesogenic state in animal models, though the relationships between human FAAH polymorphisms and obesity-related outcomes were heterogeneous, which could be due to FAAH having both pro-appetitive and anti-appetitive substrates. Genetic deletion of Mgll and Dagla as well as pharmacological inhibition of DAGL tended to reduce body weight and improve metabolic state in animal studies, though the effects of Mgll manipulation were tissue-dependent. Monitoring changes in body weight in ongoing clinical trials of FAAH inhibitors may clarify whether FAAH inhibition is a potential therapeutic strategy for treatment obesity. More preclinical work is needed to characterize the role of MAGL and DAGL modulation in obesity-related outcomes.

Some Considerations Regarding the 1H and 13C Spectra of 4-(1-azulenyl)-2,6-bis(2-heteroaryl-vinyl)- pyrylium and Pyridinium and their Corresponding Pyridines

2018 ◽  
Vol 69 (1) ◽  
pp. 64-69
Author(s):  
Liviu Birzan ◽  
Mihaela Cristea ◽  
Constantin C. Draghici ◽  
Alexandru C. Razus
Keyword(s):  
Double Bond ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Pyridinium Salts ◽  
13C Nmr Spectra ◽  
1H And 13C Nmr ◽  
Pyrylium Salts

The 1H and 13C NMR spectra of several 2,6-diheteroarylvinyl heterocycles containing 4-azulenyl moiety were recorded and their proton and carbon chemical shifts were compared with those of the compounds without double bond between the heterocycles. The influence of the nature of central and side heterocycles, molecule polarization and anisotropic effects were revealed. The highest chemical shifts were recorded for the pyrylium salts and the lowest at pyridines, but in the case of the pyridinium salts, the protons chemical shifts at the central heterocycle are more shielded due to a peculiar anisotropy of the attached vinyl groups.

scholarly journals Synthesis, Quantification, and Characterization of Fatty Acid Amides from In Vitro and In Vivo Sources

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2543
Author(s):  
Ruidong Ni ◽  
Suzeeta Bhandari ◽  
Perry R. Mitchell ◽  
Gabriela Suarez ◽  
Neel B. Patel ◽  
...  
Keyword(s):  
Drosophila Melanogaster ◽  
Fatty Acid ◽  
Apis Mellifera ◽  
Chemical Synthesis ◽  
Acid Amide ◽  
Fatty Acid Amides ◽  
Fatty Acid Amide

Fatty acid amides are a diverse family of underappreciated, biologically occurring lipids. Herein, the methods for the chemical synthesis and subsequent characterization of specific members of the fatty acid amide family are described. The synthetically prepared fatty acid amides and those obtained commercially are used as standards for the characterization and quantification of the fatty acid amides produced by biological systems, a fatty acid amidome. The fatty acid amidomes from mouse N18TG2 cells, sheep choroid plexus cells, Drosophila melanogaster, Bombyx mori, Apis mellifera, and Tribolium castaneum are presented.

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