- AMOUNTS OF ARACHIDONIC ACID IN THE BUDS OF Populus balzamifera IN THE COURSE OF THE ANNUAL CYCLE
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The paper gives information on the amount of arachidonic acid in the buds of Populus balzamifera.The presence of arachidonic acid in the buds was confirmed by TLC, GLC, coulometric titration, and an iodine number calculation.The dynamics of the amount of arachidonic acid in the buds during the annual cycle are given.
- Isaeva, E. V.,Levin, E', D.
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- Proline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acids
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The α-hydrophobic long chain-α-amino esters are prepared by α-hydroxylation of a series of fatty acid esters [derived from oleic acid (OA), linoleic acid (LA), arachidonic acid (ARA) and docosahexaenoic acid (DHA)] followed by Mitsunobu reaction and hydrazinolysis of the phthalimide. These amino esters are mixed with aldehydes and electrophilic alkenes to give very good chemical yields and diastereoselectivities of prolinate derivatives incorporating a hydrophobic long chain at the α-position. This multicomponent 1,3-dipolar cycloaddition (1,3-DC) takes place at room temperature. The synthesis of the homologue hydrophobic chain of OA is performed by its oxidation to aldehyde/racemic N-tert-butylsulfinyl imine/Neff reaction. Final 1,3-DC with benzaldehyde and N-methylmaleimide affords homologue prolinate derivative in good yield.
- Selva, Elisabet,Soto, J. Javier,Nájera, Carmen,Foubelo, Francisco,Sansano, José M.
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p. 1378 - 1386
(2019/02/05)
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- Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach
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A dual catalysis approach enables selective functionalization of unconventional feedstocks composed of complex fatty acid mixtures with highly unsaturated portions like eicosapentaenoate (20:5) along with monounsaturated compounds. The degree of unsaturation is unified by selective heterogeneous hydrogenation on Pd/γ-Al2O3, complemented by effective activation to a homogeneous carbonylation catalyst [(dtbpx)PdH(L)]+ by addition of diprotonated diphosphine (dtbpxH2)(OTf)2. By this one-pot approach, neat 20:5 as a model substrate is hydrogenated to up to 80% to the monounsaturated analogue (20:1), this is functionalized to the desired C21 α,ω-diester building block with a linear selectivity of over 90%. This catalytic approach is demonstrated to be suitable for crude microalgae oil from Phaeodactylum tricornutum genetically engineered for this purpose, as well as tall oil, an abundant waste material. Both substrates were fully converted with an overall selectivity to the linear α,ω-diester of up to 75%.
- Hess, Sandra K.,Schunck, Natalie S.,Goldbach, Verena,Ewe, Daniela,Kroth, Peter G.,Mecking, Stefan
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supporting information
p. 13487 - 13491
(2017/10/05)
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- A rapid and sensitive profiling of free fatty acids using liquid chromatography electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) after chemical derivatization
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Free fatty acids (FFAs) have diverse roles in cellular energy and signaling and they are critical molecules in various biological states. Due to the poor ionization efficiency of FFAs under electrospray ionization mass spectrometry (ESI-MS) conditions, it is a challenging aspect to construct a robust platform for profiling of various FFAs in biological samples using liquid chromatography ESI-MS. In the present study, we applied trimethylsilyldiazomethane (TMSD) derivatization to improve ionization efficiencies in the profiling of FFAs. Multiple reaction monitoring (MRM) was used for the selective quantification of methylated FFAs. The optimal TMSD methylation was validated for a reliable FFA profiling. Furthermore, the high-throughput analysis of FFAs was successfully performed in short analysis and derivatization times. To verify the utility and effectiveness of the developed method, we compared both methylation and nonmethylation (intact FFA) data in the profiling of FFAs in mice liver and plasma. It is noteworthy that the methylation derivatization provided better results in FFA profiling. Further, we performed statistical data analysis where HBV and mock mice tissues were discriminated when the methylated FFAs data were used. In the lipidomics field, the present method can also be applied for the profiling of FFAs in biological samples for biomarker discovery. The present validated LC/ESI-MS/MS assay method may also be used for FFA profiling modeling studies in other biomedical samples.
- Mok, Hyuck Jun,Lee, Jae Won,Bandu, Raju,Kang, Hong Seok,Kim, Kyun-Hwan,Kim, Kwang Pyo
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p. 32130 - 32139
(2016/05/09)
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- Synthesis of 14,15-EET from Arachidonic Acid Using Urea-Hydrogen Peroxide as the Oxidant
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14,15- Epoxyeicosatrienoic acid (14,15-EET) is an endogenous bioactive lipid with pharmacological benefits in multiple cardiovascular diseases. We describe here a practical synthesis of 14,15-EET from arachidonic acid using urea-hydrogen peroxide (UHP) as the oxidant.
- Xie, Fuchun,Li, Bingbing X.,Alkayed, Nabil J.,Xiao, Xiangshu
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p. 105 - 110
(2015/10/20)
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- GC-EI-MS analysis of fatty acid composition in brain and serum of twitcher mouse
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Globoid cell leukodystrophy or Krabbe disease is an inherited autosomal recessive disorder caused by mutations in the galactosylceramidase gene. The objective of the study was to present information about the fatty acid (FA) composition of the brain and serum of twitcher mice, a mouse model of Krabbe disease, compared to wild type, in order to identify biomarker of disease progression. We defined the FA profiles by identifying the main components present in serum and brain using GC-EI-MS analysis. The FA percentage composition was measured and data were analyzed considering the disease and the mouse age as experimental factors. Significant correlations were established, both in brain and in serum, in the fatty acid percentage composition of twitcher compared to wild type mice. The most abundant saturated fatty acid in brain was the palmitic acid (C16:0) with mean values significantly increased in twitcher mouse (p = 0.0142); moreover, three monounsaturated, three polyunsaturated (PUFA) and a plasmalogen were significantly correlated to disease. In the serum highly significant differences were observed between the two groups for three polyunsaturated fatty acids. In fact, the docosahexaenoic acid (C22:6n3c) content was significantly increased (p = 0.0116), while the C20 PUFA (C20:3n6c and C20:5n3c) were significantly decreased in twitcher serum samples. Our study shows a specific FA profile that may help to define a possible pattern that could distinguish between twitcher and wild type; these data are likely to provide insight in the identification of new biomarkers to monitor the disease progression and thereby permit the critical analysis of therapeutic approaches.
- Zanfini, Assunta,Dreassi, Elena,Berardi, Anna,Piomboni, Paola,Costantino-Ceccarini, Elvira,Luddi, Alice
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p. 1115 - 1125
(2015/02/19)
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- Mild acetal cleavage using B-chlorocatecholborane in the synthesis of rearrangement-sensitive 2-arachidonoylglycerol
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A mild method for the cleavage of an acetal to afford a rearrangement sensitive diol using B-chlorocatecholborane was developed for the synthesis of the endogenous cannabinoid neurochemical messenger 2-arachidonoylglycerol. The tendency for rearrangement of 2-arachidonoylglycerol to the corresponding 1-arachidonoylglycerol was precluded with this reagent. Features of the partial recyclization to an isomeric acetal provide mechanistic detail.
- Roche, Michael J.,Madren, Seth M.,Tallent, C. Ray,Carroll, F. Ivy,Seltzman, Herbert H.
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p. 3825 - 3827
(2012/08/28)
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- DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS
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Provided are efficient, cost-effective and water tolerant methods (e.g., single-vial methods) for preparing fatty acid esters from organic matter, comprising: obtaining organic matter comprising at least one fat substituent, contacting the organic matter in a reaction mixture with a basic solution under conditions suitable to provide for hydrolytic release of monomeric fatty acids from the at least one fat substituent to provide a base-treated reaction mixture, and esterifying the monomeric fatty acids of the base-treated reaction mixture by acidification of the reaction mixture and treating in the presence of an organic alcohol to provide fatty acid esters. The methods optionally further comprise, prior to esterifying, neutralizing the base-treated reaction mixture to provide for neutralized fatty acids, separating the neutralized fatty acids from the neutralized reaction mixture, and dissolving the separated fatty acids in the esterification reaction mixture. Also provided are related methods and kits for fat analysis.
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Page/Page column 18; 21-22; 29
(2008/12/07)
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- Synthesis of all-trans arachidonic acid and its effect on rabbit platelet aggregation
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A simple and high-yielding method to convert natural all-cis PUFA derivatives to the corresponding all-trans geometrical isomers is described. The method is based on the thiyl radical-catalyzed cis-trans isomerization. The all-trans isomer of arachidonic acid was found to cause rabbit platelet aggregation at concentrations higher than 0.1 mM and inhibition of PAF-induced platelet aggregation in a concentration dependent manner with an IC50 in the micromolar range.
- Anagnostopoulos, Dimitris,Chatgilialoglu, Chryssostomos,Ferreri, Carla,Samadi, Abdelouahid,Siafaka-Kapadai, Athanassia
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p. 2766 - 2770
(2007/10/03)
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- Synthesis of 15N-, 13C-, and 2H-labeled methanandamide analogs
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Four isotopically labeled, metabolically stable analogs of arachidonylethanolamide (anandamide), an endogenous cannabinoid ligand, were synthesized via a five-step reaction sequence starting from arachidonic acid. These stable methanandamide derivatives will serve as probes for studying the conformational properties of anandamide in model membrane systems using solid-state NMR spectroscopy. The synthetic methods described can be applied to the preparations of other anandamide analogs with isotopic labeling in different positions of the molecule, which could be utilized in biochemical and pharmacological experiments. Copyright
- Yao, Fen-Mei,Palmer, Sonya L.,Khanolkar, Atmaram D.,Tian, Xiaoyu,Guo, Jianxin,Makriyannis, Alexandros
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p. 115 - 129
(2007/10/03)
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- Hemisynthesis and preliminary evaluation of novel endocannabinoid analogues
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Three new endocannabinoid analogues in which amide moiety was replaced either by oxomethylene group or ester moiety with simultaneous substitution of both α-hydrogens with methyl groups were synthesized and their abilities to interact with CB1-receptor and FAAH were investigated.
- El Fangour, Siham,Balas, Laurence,Rossi, Jean-Claude,Fedenyuk, Andrey,Gretskaya, Natalia,Bobrov, Mikhail,Bezuglov, Vladimir,Hillard, Cecilia J.,Durand, Thierry
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p. 1977 - 1980
(2007/10/03)
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- A convenient method for the synthesis and one-pot reaction of acyl chlorides using a scavenging resin
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A simple, efficient and fast method for the preparation of acyl halides from fatty carboxylic acids using a solid phase scavenging approach is presented herein. The title compounds can then be isolated, used as a solution or react in one-pot to form esters and amides with good to excellent yields.
- Girard,Tranchant,Niore,Herscovici
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p. 1577 - 1580
(2007/10/03)
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- Insecticidal compounds against mosquito larvae from Oscillatoria agardhii strain 27
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It was found that Oscillatoria agardhii strain 27 produced compounds toxic against mosquito larvae (Aedes albopictus), therefore, these compounds were extracted and separated for insecticide development. Structural characterization of the toxic fraction by 1H-NMR and GC-MS showed that these compounds are not the neurotoxins or hepatotoxins conventionally produced by Oscillatoria, but it contained a mixture of unsaturated fatty acids, oleic, linoleic, and γ-linolenic acids, as well as saturated fatty acids, myristic, palmitic, and stearic acids. In a bioassay developed for these hydrophobic compounds using mosquito larvae, authentic unsaturated fatty acids were shown to be toxic, whereas saturated ones were active. The results suggested that it might be possible to use unsaturated fatty acids as environmentally safe and effective insecticides without the side effects of the chemically synthesized insecticides. (C) 2000 by John Wiley and Sons, Inc.
- Harada, Ken-Ichi,Suomalainen, Mette,Uchida, Hideaki,Masui, Hiroaki,Ohmura, Kuniyo,Kiviranta, Jari,Niku-Paavola, Marja-Leena,Ikemoto, Takaya
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p. 114 - 119
(2007/10/03)
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- A convenient strategy for the synthesis of β,γ-unsaturated aldehydes and acids. A construction of skipped dienes
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A novel strategy is described for the synthesis of β,γ-unsaturated aldehydes which are the useful-synthons for the synthesis of arachidonic acid and other eicosanoid products. These β,γ-unsaturated aldehydes have been used in the total synthesis of arachidonic acid.
- Saha, Goutam,Basu, Manas K.,Kim, Seongjin,Jung, Young-Ju,Adiyaman, Yurdanur,Adiyaman, Mustafa,Powell, William S.,FitzGerald, Garret A.,Rokach, Joshua
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p. 7179 - 7183
(2007/10/03)
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- A selective method for the preparation of aliphatic methyl esters in the presence of aromatic carboxylic acids
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2,2-Dimethoxypropane, methanol and a catalytic amount of HCl selectively esterify aliphatic carboxylic acids, in the presence of aromatic carboxylic acids, at room temperature and in high yields.
- Rodriguez,Nomen,Spur,Godfroid
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p. 8563 - 8566
(2007/10/03)
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- 1,1'-OXALYLDIIMIDAZOLE, A NEW REAGENT FOR ACTIVATION OF CARBOXYLIC ACID
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Carboxylic acids and their salts are converted into the 1-acylimidazoles by the title reagent.This reaction is applied for esterification of fatty acids.
- Murata, Shizuaki
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p. 1819 - 1820
(2007/10/02)
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