Synthesis of Fatty-Acid Ethanolamides from Linum catharticum Oils and Cololabis saira Fats

Karaulov, A. E.; Rybin, Viatcheslav; Kuklev, Dmitry V.; Akulin, V. N.

doi:10.1023/b:conc.0000039128.78645.a8

Cited by 6 publications

(4 citation statements)

References 8 publications

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“…Most commonly, direct conversion of FAG to FAAA has been studied using ethanolamine as a solvent with ,, or without sodium methoxide catalyst. A conversion of FAG to FAAA through fatty acid methyl ester (FAME) has also been reported with analogous reaction conditions and with excellent yields for both steps …”

Section: Introductionmentioning

confidence: 94%

“…A number of studies have reported conversion of fatty acid triglycerides (FAG) from terrestrial biomass (i.e., vegetable oil) to alkanolamides. , In general, FAAA can be synthesized from alkanolamine with a fatty acyl donor, such as free fatty acids, fatty acid chlorides, fatty acid alkyl esters, and FAG. , Acyl chlorides have been used to deliver FAAA products with sufficient purity for biological studies , but are likely unsuitable for industrial-scale production because of cost and the corrosive nature of the reagents. Fatty acid conversion to FAAA can be accomplished using sodium methoxide catalyst but requires harsh reaction conditions due to ionic salt formation .…”

Section: Introductionmentioning

confidence: 99%

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Efficient Production of Alkanolamides from Microalgae

Mudiyanselage

Yao

Viamajala

et al. 2015

Ind. Eng. Chem. Res.

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Fatty acid alkanolamides (FAAA) are lipid derivatives with industrial applications as biosurfactants and biolubricants. Although conventionally produced from vegetable oils, use of alternative renewable sources that do not compete with the food supply chain, such as microalgae, is desirable. We studied the production of FAAA through direct in situ amidation of algal biomass or by amidation of fatty acid methyl esters (FAME) recovered from in situ transesterification of algae. In situ transesterification resulted in spontaneous formation of a distinct FAME phase, which could be easily recovered and converted to FAAA. With this two-step transesterification-followed-by-amidation method, >95% of algal lipids were recovered as FAAA products. In situ amidation did not result in a separate product phase, likely because of the amphiphilic nature of the product. However, extraction with ethyl acetate allowed recovery of nearly 90% of the biomass lipids as FAAA after in situ amidation.

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Section: Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Efficient Production of Alkanolamides from Microalgae

Mudiyanselage

Yao

Viamajala

et al. 2015

Ind. Eng. Chem. Res.

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“…As there was no commercially available reference standard of THEA, we first confirmed that any signal obtained by MS was not the result of a molecule of identical mass and retention time. Therefore, it was necessary to synthesize a THEA standard from accepted methodologies (29). Importantly, we first assessed our synthesis protocol for DHEA so that we could compared it to a commercially available DHEA standard and were then able to synthesize and purify a THEA standard that could be used for accurate identification of THEA in mouse whole brain.…”

Section: Discussionmentioning

confidence: 99%

“…Methods for DHEA and THEA synthesis were adopted from Karaulov et al (29). Briefly, DHA (Nu-Chek Prep, Inc., Elysian, MN) and THA methyl esters (Larodan, Inc., Monroe, MI) were treated with fresh monoethanolamine (1:5 molar ratio; Millipore-Sigma, Burlington, MA) and trifluoroacetic acid (Millipore-Sigma).…”

Section: Organic Synthesis Of Dhea and Theamentioning

confidence: 99%

Tetracosahexaenoylethanolamide, a novel N-acylethanolamide, is elevated in ischemia and increases neuronal output

Lin

Metherel

Miceli

et al. 2020

Journal of Lipid Research

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N-acylethanolamines (NAEs) are endogenous lipid-signaling molecules derived from fatty acids that regulate numerous biological functions, including in the brain. Interestingly, NAEs are elevated in the absence of fatty acid amide hydrolase (FAAH) and following CO2-induced ischemia/hypercapnia, suggesting a neuroprotective response. Tetracosahexaenoic acid (THA) is a product and precursor to docosahexaenoic acid (DHA), however, the NAE product – tetracosahexaenoylethanolamide (THEA) – has never been reported. Presently, THEA was chemically synthesized as an authentic standard to confirm THEA presence in biological tissues. Whole brains were collected and analyzed for unesterified THA, total THA and THEA in wild-type and FAAH-KO mice that were euthanized by either head-focused microwave fixation, CO2 + microwave or CO2 only. PPAR activity by transient transfection assay and ex vivo neuronal output in medium spiny neurons (MSN) of the nucleus accumbens by patch clamp electrophysiology were determined following THEA exposure. THEA in the wild-type mice was nearly doubled (p<0.05) following ischemia/hypercapnia (CO2 euthanization) and up to 12-times higher (p<0.001) in the FAAH-KO compared to wild-type. THEA did not increase (p>0.05) transcriptional activity of PPARs relative to control, but 100nM THEA increased (p<0.001) neuronal output in MSN of the nucleus accumbens. Here were identify a novel NAE, THEA, in the brain that is elevated upon ischemia/hypercapnia and by knockout of the FAAH enzyme. While THEA did not activate PPAR, it augmented the excitability of MSN in the nucleus accumbens. Overall, our results suggest THEA is a novel NAE that is produced in the brain upon ischemia/hypercapnia and regulates neuronal excitation.

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