- Synthesis of all-Z-1,6,9,12,15-octadecapenten-3-one, a vinyl ketone polyunsaturated marine natural product isolated from callysponga sp
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The synthesis of the marine natural product 1,6Z,9Z,12Z,15Z- octadecapentaen- 3-one (1) has been achieved by two different routes starting from the ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively. Using EPA ethyl ester as starting material the polyunsaturated vinyl ketone lipid 1 was obtained in 17% overall yield.
- Langseter, Anne Marie,Stenstroom, Yngve,Skattebool, Lars
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Read Online
- Antioxidative Properties and Chemical Changes of Quercetin in Fish Oil: Quercetin Reacts with Free Fatty Acids to Form Its Ester Derivatives
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In this research, we studied the antioxidative properties and chemical changes of quercetin in fish oil during accelerated storage at 60 °C for 5 days. Gas chromatography (GC) analysis showed that quercetin inhibited aldehyde formation and unsaturated fatty acid oxidation in fish oil significantly; however, the inhibitory effects decreased gradually with prolonged heating time. Moreover, quercetin was consumed with increasing heating time. Some new phenolic derivatives were discovered in the fish oil with quercetin, with their structures fully elucidated by LC-MS/MS and comparison with newly synthesized ones (characterized by MS and NMR spectroscopy). Based on their chemical structures, we proposed that quercetin reacted with EPA and DHA to form the corresponding quercetin fatty acid esters in fish oil. In addition, the newly formed quercetin-3-O-eicosapentaenoate and quercetin-3-O-docosahexaenoate showed weaker DPPH and ABTS radical cation scavenging activity but much improved lipophilicity, higher cell membrane affinity, and hence enhanced cellular antioxidant activity compared with the parent quercetin. Overall, quercetin could be used as a safe dietary polyphenol to inhibit lipid oxidation. The newly formed quercetin-polyunsaturated fatty acid esters may render improved bioactivity to humans, which needs further investigation.
- Liu, Shaojun,Zhu, Yamin,Liu, Ning,Fan, Daming,Wang, Mingfu,Zhao, Yueliang
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p. 1057 - 1067
(2021/02/01)
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- PROCESSES IN THE PREPARATION OF POLYUNSATURATED KETONE COMPOUNDS
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A process comprising the following steps: a-i) treating a polyunsaturated ester with a base in a solvent of lower alcohol and water to form the corresponding polyunsaturated acid; a-ii) treating the product from step a-i), especially the crude product, with a halolactonization agent in the solvent of lower alcohol and water, to form the corresponding polyunsaturated halolactone; and a-iii) treating the product from step a-ii), especially the crude product, with a reagent in the solvent of lower alcohol and water to convert the polyunsaturated halolactone to the corresponding polyunsaturated epoxide lower alkyl ester.
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Page/Page column 36-37
(2019/12/04)
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- Fatty Acid Cysteamine Conjugates as Novel and Potent Autophagy Activators That Enhance the Correction of Misfolded F508del-Cystic Fibrosis Transmembrane Conductance Regulator (CFTR)
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A depressed autophagy has previously been reported in cystic fibrosis patients with the common F508del-CFTR mutation. This report describes the synthesis and preliminary biological characterization of a novel series of autophagy activators involving fatty acid cysteamine conjugates. These molecular entities were synthesized by first covalently linking cysteamine to docosahexaenoic acid. The resulting conjugate 1 synergistically activated autophagy in primary homozygous F508del-CFTR human bronchial epithelial (hBE) cells at submicromolar concentrations. When conjugate 1 was used in combination with the corrector lumacaftor and the potentiator ivacaftor, it showed an additive effect, as measured by the increase in the chloride current in a functional assay. In order to obtain a more stable form for oral dosing, the sulfhydryl group in conjugate 1 was converted into a functionalized disulfide moiety. The resulting conjugate 5 is orally bioavailable in the mouse, rat, and dog and allows a sustained delivery of the biologically active conjugate 1.
- Vu, Chi B.,Bridges, Robert J.,Pena-Rasgado, Cecilia,Lacerda, Antonio E.,Bordwell, Curtis,Sewell, Abby,Nichols, Andrew J.,Chandran, Sachin,Lonkar, Pallavi,Picarella, Dominic,Ting, Amal,Wensley, Allison,Yeager, Maisy,Liu, Feng
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p. 458 - 473
(2017/04/26)
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- PROCESS FOR THE PREPARATION OF A POLYUNSATURATED KETONE COMPOUND
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The invention relates to the manufacture of certain polyunsaturated compounds employing a particular application of the Mitsonobu reaction in the presence of at least one anti-oxidant. We have found a method of making a pharmaceutically-acccptable polyunsaturated ester or thioester compound directly, which can ultimately be converted to the advantageous ketone compounds, in which unwanted oxidation and cis/trans isomerization are substantially reduced or eliminated using particular Mitsonobu chemistry.
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Page/Page column 21; 22
(2015/02/19)
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- One-pot synthesis of polyunsaturated fatty acid amides with anti-proliferative properties
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A one-pot environmentally friendly transamidation of ω-3 fatty acid ethyl esters to amides and mono- or diacylglycerols was investigated via the use of a polymer-supported lipase. The method was used to synthesize a library of fatty acid monoglyceryl esters and amides. These new derivatives were found to have potent growth inhibition effects against A549 lung cancer cells.
- Tremblay, Hugo,St-Georges, Catherine,Legault, Marc-Andr,Morin, Caroline,Fortin, Samuel,Marsault, Eric
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p. 5635 - 5638
(2015/01/09)
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- PROCEDURE FOR THE OBTAINMENT OF FATTY ACIDS OF PHARMACOLOGICAL AND NUTRITIONAL INTEREST
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This invention refers to a procedure for obtaining fatty acids of pharmacological and nutritional interest that comprises the steps of feeding a gas comprising CO2 into a reactor that contains a culture that comprises at least one species of microalgae capable of photosynthesis, the process of photosynthesis by the species of microalgae from the CO2 supplied, producing a biomass that contains a general formula (I) compound: extraction of the general formula (I) compound from the biomass obtained and concentration and/or purification of this compound.
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Paragraph 0151-0160
(2013/08/14)
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- METHOD FOR THE SYNTHESIS OF DHA
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A method for preparing docosahexaenoic acid (DHA). The method comprises coupling a compound represented by Formula I with a compound represented by Formula II followed by partial hydrogenation to obtain a compound represented by Formula III. The compound represented by Formula III acts as a DHA precursor and thus can be hydrolysed to obtain DHA. Novel starting materials represented by Formula I and Formula II, and synthetic routes for preparing the same are also provided.
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Page/Page column 65-66
(2012/10/08)
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- Concise syntheses of three ω-3 polyunsaturated fatty acids
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The synthesis of the three ω-3 polyunsaturated fatty acids, eicosatetraenoic acid (3), docosapentaenoic acid (4), and stearidonic acid (5) has been achieved using eicosapentaenoic acid or docosahexaenoic acid as the starting materials.
- Jakobsen, Martin Gjerde,Vik, Anders,Hansen, Trond Vidar
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supporting information
p. 5837 - 5839
(2013/01/13)
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- Chemoenzymatic synthesis of a focused library of enantiopure structured 1-O-alkyl-2,3-diacyl-sn-glycerol type ether lipids
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A highly efficient two-step chemoenzymatic synthesis of enantiopure structured ether lipids of the 1-O-alkyl-2,3-diacyl-sn-glycerol type has been developed. Chimyl, batyl and selachyl alcohols possessing pure saturated fatty acid (SFA) attached to the sn-3 position and pure EPA and DHA attached to the sn-2 position were obtained under full regiocontrol. This was offered by mild conditions and a highly efficient lipase that operated at room temperature. High-resolution 1H NMR spectroscopy was used to monitor the progress of the reactions and to evaluate the full regiocontrol of the reactions involved by keeping track of all prospective adducts involved in these reactions. This was extended to preparation of a focused library of eight monoacyl intermediate adducts for all even-numbered SFA ranging from C2-C16 and the corresponding EPA and DHA structured diacyl glycerol ethers (DAGE) products for chimyl, batyl and selachyl alcohols, the total of 72 compounds.
- Magnusson, Carlos D.,Gudmundsdottir, Anna V.,Haraldsson, Gudmundur G.
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body text
p. 1821 - 1836
(2011/04/17)
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- METHOD FOR INCREASING THE CONTENT OF DOCOSAHEXAENOIC ACID IN FAT-CONTAINING MATERIALS OR IN FATS AND OILS
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[PROBLEMS] To provide a fat-and-oil in which the content of docosahexaenoic acid is increased. [MEANS FOR SOLVING PROBLEMS] A process for producing highly unsaturated fatty acids comprising culturing a stramenopile capable of producing highly unsaturated fatty acids in a culture medium containing an inhibitor for fatty acid desaturases; fats-and-oils in which the content of highly unsaturated fatty acids, particularly docosahexaenoic acid produced by the relevant method, is increased. A method for enhancing the productivity of highly unsaturated fatty acids in stramenopiles, comprising culturing a stramenopile in a culture medium containing an inhibitor for fatty acid desaturases; stramenopiles having the enhanced productivity of highly unsaturated fatty acids, generated by the relevant method. Particularly, the process for producing highly unsaturated fatty acids, the method for enhancing the productivity of highly unsaturated fatty acids, and the stramenopile having the enhanced productivity of highly unsaturated fatty acids, wherein the stramenopile is a microorganism classified into Labyrinthulea.
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Page/Page column 3-4
(2010/05/13)
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- ORALLY ACTIVE CURCUMINOID COMPOUNDS
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The invention discloses a compound of formula (I) wherein, at least one of R1, R2, R3 and R4 is -C(=O)Rn and R1, R2 R3 and R4 are H or CH3 and Rn is alkyl or alkenyl group. The alkenyl group have one or more number of double bonds either in cis form or trans form or both. In Rn, where n is 12 to 30 carbons; and pharmaceutically acceptable salt thereof. The said alkenyl groups are preferably selected from the group consisting of eicosapentaenoic acid (EPA) or DHA (docosahexaenoic acid). This invention further discloses processes for their preparation of compounds of formula I and pharmaceutical compositions that contain these compounds.
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Page/Page column 20
(2010/04/03)
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- Chemoenzymatic synthesis of symmetrically structured triacylglycerols possessing short-chain fatty acids
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Synthesis of symmetrically structured triacylglycerols possessing bioactive n-3 polyunsaturated fatty acids (eicosapentaenoic acid or docosahexaenoic acid) at the 2-position and a short-chain fatty acid (C2, C4, C6) located at the end-positions by a highly efficient two-step chemoenzymatic process is described. Full regiocontrol devoid of any acyl-migration side reactions was obtained in both a lipase promoted step to introduce the short-chain fatty acids exclusively into the primary alcohol positions of glycerol using activated vinyl esters at low temperature and a subsequent coupling reaction involving free EPA and DHA using EDAC as a coupling agent.
- Magnusson, Carlos D.,Haraldsson, Gudmundur G.
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experimental part
p. 2728 - 2731
(2010/05/17)
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- Synthesis and stability of phosphatidylcholines bearing polyenoic acid hydroperoxides at the sn-2 position
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The antitumor and antimalarial activity of fish oils may involve the action of phospholipid hydroperoxides. Two such phosphatidylcholines, 1 and 2, bearing the hydroperoxides of docosahexaenoic and eicosapentaenoic acids - the two major fatty acids in fish oils - have been synthesized. In spite of its high degree of unsaturation, 1 is sufficiently stable to permit its use in biological studies.
- Onyango, Arnold N.,Inoue, Takafumi,Nakajima, Shuhei,Baba, Naomichi,Kaneko, Takao,Matsuo, Mitsuyoshi,Shimizu, Sakayu
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p. 1755 - 1757
(2007/10/03)
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- Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids
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There are indications in the recent literature that the location of polyunsaturated fatty acids, such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), in triacylglycerols (TAG) may influence their oxidative stability. To address that question, two types of structured lipids were designed and synthesized: firstly, a TAG molecule possessing pure EPA or DHA at the mid-position with stearic acid at the outer positions; and secondly, a TAG molecule possessing pure EPA or DHA located at one of the outer positions with stearic acid at the mid-position and the remaining end position. The former adduct was synthesized in two steps by a chemoenzymatic approach. In the first step 1,3-distearoylglycerol was afforded in good yield (74%) by esterifying glycerol with two equivalents of stearic acid in ether in the presence of silica gel using LipozymeTM as a biocatalyst. This was followed by a subsequent chemical esterification with pure EPA or DHA using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide as a coupling agent in the presence of 4-dimethylaminopyridine in dichloro-methane in excellent yields (94 and 91%, respectively). The latter adduct was synthesized in two enzymatic steps. In the first step tristearoylglycerol was prepared in very high yield (88%) by esterifying glycerol with a stoichiometric amount of stearic acid under vacuum at 70-75 °C using an immobilized Candida antarctica lipase without a solvent. That adduct was subsequently treated in an acidolysis reaction with two equivalents of EPA or DHA without solvent at 70-75 °C or in toluene at 40 °C in the presence of Lipozyme to afford the desired product in moderate yields (44 and 29%, respectively).
- Haraldsson, Gudmundur G.,Halldorsson, Arnar,Kulas, Elin
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p. 1139 - 1145
(2007/10/03)
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- Syntheses of some polyunsaturated sulfur- and oxygen-containing fatty acids related to eicosapentaenoic and docosahexaenoic acids.
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With the aim of enhancing selectively the beneficial biological effects of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) a number of polyunsaturated fatty acids containing sulfur or oxygen atoms in the chain has been synthesized starting from EPA and DHA, respectively. Oxidative degradation of these acids led to the corresponding aldehydes all-(Z)-3,6,9,12-pentadecatetraenal and all-(Z)-3,6,9,12,15-octadecapentaenal. Reactions with DBU converted these aldehydes quantitatively into the conjugated isomers (2E,6Z,9Z,12Z)-pentadecatetraenal and (2E,6Z,9Z,12Z,15Z)-octadecapentaenal, respectively. The four aldehydes were transformed by a sequence of reactions comprising reduction to the alcohols, halogenation and substitution with mercapto esters into the corresponding sulfur containing polyunsaturated fatty acid esters. The oxygen containing esters were prepared from the respective alcohol by boron trifluoride catalysed reaction with ethyl diazoacetate.
- Flock,Lundquist,Skattebol
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p. 436 - 445
(2007/10/03)
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- The Synthesis of Homogeneous Triglycerides of Eicosapentaenoic Acid and Docosahexaenoic Acid by Lipase
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A highly efficient synthesis of homogeneous triglycerides of either pure eicosapentaenoic acid, 1, or docosahexaenoic acid, 2, by an immobilized non-regiospecific yeast lipase from Candida antarctica is described.Two methods were used: Interesterification of tributyrin and direct esterification of glycerol with stoichiometric amount of 99percent EPA or DHA as ethyl esters and free fatty acids, respectively.Both processes were performed under vacuum at 65 deg C in the absence of any solvent.The volatile co-products were condensed into a cooled trap, thus shifting the equilibrium toward completion.Complete incorporation was reached in less than 72 h for all cases, but the direct esterification was found to proceed considerably faster than the transesterification as were both processes involving EPA as compared to DHA.High-field 1H NMR spectroscopy analysis offered detailed investigation of the intermediate glycerides during the direct esterification reaction.The purity of the resulting crude products which were afforded in excellent yields was very high.
- Haraldsson, Gudmundur G.,Gudmundsson, Birgir Oe.,Almarsson, Oern
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p. 941 - 952
(2007/10/02)
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- Method of purifying polyunsaturated aliphatic compounds and apparatus therefor
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[Object] A fatty acid-related polyunsaturated compound can be selectively purified using an industrially operable successive method under moderate conditions., [Content] A highly purified fatty acid-related polyunsaturated compound is obtained by a process comprising steps of forming a complex with silver on account of the high degree of unsaturation of the fatty acid-related polyunsaturated compound, isolating the complex from other fats on account of the hydrophilicity of the complex and then applying dissociating procedures to the complex to obtain the fatty acid-related polyunsaturated compound as a target substance on account of the hydrophobicity of the fatty acid-related polyunsaturated compound. As to the procedures for dissociation, addition of a dissociating agent and reduction of silver are disclosed. As to the dissociating agent, various compounds which produce insoluble composition with silver other than water are disclosed. Furthermore, an apparatus appropriately used to carry out this method is also disclosed.
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- A SIMPLE PROCESS FOR THE PURIFICATION OF ARACHIDONIC ACID
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Pure arachidonic acid (1) and docosahexanoic acid (3) are available by a two-step purification method from commercial 50percent acids with high efficiency.
- Corey, E. J.,Wright, Stephen W.
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p. 2729 - 2730
(2007/10/02)
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