- 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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- Epigallocatechin (EGC) esters as potential sources of antioxidants
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Epigallocatechin (EGC) was acylated with selected fatty acids, namely propionic acid [C3:0], caprylic acid [C8:0], lauric acid [C12:0], stearic acid [C18:0]) and docosahexaenoic acid (DHA)[C22:6n-3] in order to increase its lipophilicity. Monoesters were
- Ambigaipalan, Priyatharini,Oh, Won Young,Shahidi, Fereidoon
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- Preparation of Quercetin Esters and Their Antioxidant Activity
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Quercetin, a polyphenolic compound, is widely distributed in plants and has numerous health benefits. However, its hydrophilicity can compromise its use in lipophilic systems. For this reason, quercetin was esterified with 12 different fatty acids as their acyl chlorides with varying chain lengths and degrees of unsaturation. Two monoesters (Q-3′-O-monoester and Q-3-O-monoester) and four diesters (Q-7,3′-O-diester, Q-3′,4′-O-diester, Q-3,3′-O-diester, and Q-3,4′-O-diester) were the major products as was shown by HPLC-MS and 1H-NMR data. The lipophilicity of quercetin derivatives was calculated; this was found to increase with fatty acid chain length. The antioxidant potential of quercetin and its derivatives was evaluated by using DPPH radical and ABTS radical cation scavenging activity; quercetin showed the highest radical scavenging activity among all tested samples. Despite the decrease of antioxidant activity in this study, the derivatives may show better antioxidant activity in lipophilic media and display improved absorption and bioavailability in the body once consumed.
- Oh, Won Young,Ambigaipalan, Priyatharini,Shahidi, Fereidoon
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p. 10653 - 10659
(2019/10/19)
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- Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
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N-Acyl amino acids directly bind mitochondria and function as endogenous uncouplers of UCP1-independent respiration. We found that administration of N-acyl amino acids to mice improves glucose homeostasis and increases energy expenditure, indicating that this pathway might be useful for treating obesity and associated disorders. We report the full account of the synthesis and mitochondrial uncoupling bioactivity of lipidated N-acyl amino acids and their unnatural analogues. Unsaturated fatty acid chains of medium length and neutral amino acid head groups are required for optimal uncoupling activity on mammalian cells. A class of unnatural N-acyl amino acid analogues, characterized by isoindoline-1-carboxylate head groups (37), were resistant to enzymatic degradation by PM20D1 and maintained uncoupling bioactivity in cells and in mice.
- Lin, Hua,Long, Jonathan Z.,Roche, Alexander M.,Svensson, Katrin J.,Dou, Florence Y.,Chang, Mi Ra,Strutzenberg, Timothy,Ruiz, Claudia,Cameron, Michael D.,Novick, Scott J.,Berdan, Charles A.,Louie, Sharon M.,Nomura, Daniel K.,Spiegelman, Bruce M.,Griffin, Patrick R.,Kamenecka, Theodore M.
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supporting information
p. 3224 - 3230
(2018/04/23)
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- A study of synthetic approaches to 2-acyl DHA lysophosphatidic acid
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Lysophosphatidic acid (LPA) is a chemical mediator with a very simple glycerophospholipid structure. 1-Acyl LPA and 2-acyl LPA are biosynthesized in vivo. Unlike 1-acyl LPA, the biological function of 2-acyl LPA has been hardly elucidated and even organic synthesis of 2-acyl LPA had not been established. We suppressed acyl migration by formation of a salt with a phosphate group in order to synthesize 2-acyl LPA condensed with docosahexaenoic acid.
- Yamamoto, Yoshinori,Itoh, Toshimasa,Yamamoto, Keiko
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p. 8186 - 8192
(2017/10/13)
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- Lipophilization of resveratrol and effects on antioxidant activities
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Resveratrol (R), a polyphenol, was structurally modified via esterification with selected fatty acids to expand its potential application in lipophilic foods, drugs, and cosmetics. The esterification was carried out using 12 different fatty acids with varying chain lengths and degrees of unsaturation (C3:0-C22:6). Two monoesters, two diesters, and one triester were identified by high-performance liquid chromatography-mass spectrometry, and the monoesters (R-3-O-monodocosahexaenoate and R-4'-O-monodocosahexaenoate) were structurally confirmed by nuclear magnetic resonance. The lipophilicity of resveratrol and its alkyl esters was calculated using ALOGPS 2.1. Resveratrol exhibited greater antioxidant activity in both 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation scavenging assays. Resveratrol esters with long-chain fatty acids (C18:0 and C18:1) showed higher antioxidant activity in the DPPH radical scavenging assay, whereas short-chain fatty acid (C3:0, C4:0, and C6:0) showed higher antioxidant activity in the ABTS radical cation scavenging assay. The results may imply that resveratrol derivatives could be used in lipophilic media as health beneficial antioxidants.
- Oh, Won Young,Shahidi, Fereidoon
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p. 8617 - 8625
(2017/11/09)
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- FATTY ACID ANTIVIRAL CONJUGATES AND THEIR USES
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The invention relates to fatty acid antiviral conjugates; compositions comprising an effective amount of a fatty acid antiviral conjugate; and methods for treating or preventing a viral infection comprising the administration of an effective amount of a fatty acid antiviral conjugate.
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Paragraph 0836; 0837
(2016/06/01)
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- DNA SYNTHASE INHIBITOR
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PROBLEM TO BE SOLVED: To provide a compound having DNA synthase inhibitory activity, and a pharmaceutical composition comprising the compound as an active ingredient (DNA synthase inhibitor, anticancer agent and antiinflammatory agent). SOLUTION: A DNA synthase inhibitor comprises a compound represented by general formula (1) as an active ingredient. An example of the compound is carboxylate ester of plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone). COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0127-0129
(2016/10/10)
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- FATTY ACID ANTIVIRAL CONJUGATES AND THEIR USES
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The invention relates to fatty acid antiviral conjugates; compositions comprising an effective amount of a fatty acid antiviral conjugate; and methods for treating or preventing a viral infection comprising the administration of an effective amount of a fatty acid antiviral conjugate.
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Paragraph 0958; 0959
(2014/09/30)
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- ASCORBATE ESTERS OF OMEGA-3 FATTY ACIDS
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The present invention provides ascorbate esters of omega-3 fatty acids as their pharmaceutically-acceptable salts and pharmaceutically- acceptable formulations for use as dietary supplements with enhanced antioxidant properties, in improving the effectiveness of other drugs and in treatment of hypertriglyceridemia, hypercholestolemia, diabetes, psychiatric and neurological disorders, attention deficit and hyperactivity disorder, and as cosmeceuticals.
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Page/Page column 19-20
(2014/09/16)
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- NOVEL ANTI-CANCER ISOCARBOSTYRIL ALKALOID CONJUGATES
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The present application is directed to covalent conjugates between an isocarbostyril alkaloid and a lipophilic biomolecule, to pharmaceutical compositions comprising the conjugates and to therapeutic uses thereof, in particular for treating cancer.
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Paragraph 0087
(2013/03/26)
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- FATTY ACID ANTIVIRAL CONJUGATES AND THEIR USES
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The invention relates to fatty acid antiviral conjugates; compositions comprising an effective amount of a fatty acid antiviral conjugate; and methods for treating or preventing a a viral infection comprising the administration of an effective amount of a fatty acid antiviral conjugate.
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Paragraph 00194
(2013/07/05)
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- METHODS OF PREPARING FREE POLYUNSATURATED FATTY ACIDS
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Provided herein are methods of making compositions of free fatty acids and alkyl esters of polyunsaturated fatty acids (PUFAs). Also provided are compositions comprising a PUFA selected from a free fatty acid or a ester wherein the PUFA is made according to a method of the invention.
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Page/Page column 29
(2012/09/10)
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- Analogs of 2-arachidonoylglycerin containing the no-donor group
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1, 3-Dinitroglyceryl esters of fatty acids, analogs of endocannabinoid 2-arachidonoylglycerin, were synthesized. Various methods for esterifying fatty acids with glycerine dinitrate were developed.
- Serkov,Gretskaya,Bezuglov
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p. 367 - 370
(2012/10/30)
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- Improved LC-MS method for the determination of fatty acids in red blood cells by LC-orbitrap MS
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We report a new method for fast and sensitive analyses of biologically relevant fatty acids (FAs) in red blood cells (RBC) by liquid chromatography mass spectrometry (LC-MS). A new chemical derivatization approach was developed forming picolylamides from FAs in a quantitative reaction. Fourteen derivatized FA standards, including saturated and unsaturated FAs from C14 to C22, were efficiently separated within 15 min. In addition, the use of a recently introduced benchtop orbitrap mass spectrometer under positive electrospray ionization (ESI) full scan mode showed a 2-10-fold improvement in sensitivity compared with a conventional tandem MS method, with a limit of detection in the low femtomole range for saturated and unsaturated FAs. The developed method was applied to determine FA concentrations in RBC with intra- and interday coefficients of variation below 10%.
- Li, Xingnan,Franke, Adrian A.
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experimental part
p. 3192 - 3198
(2011/11/04)
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- Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response
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We previously found that vitamin K3 (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase γ (pol γ). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglones conjugated with C2:0 to C22:6 fatty acid (5-O-acyl juglones). The chemically modified juglones enhanced mammalian pol inhibition and their cytotoxic and anti-inflammatory activities. The juglone conjugated with oleic acid (C18:1-acyl juglone) showed the strongest inhibition of DNA replicative pol α activity and human colon carcinoma (HCT116) cell growth in 10 synthesized 5-O-acyl juglones. C12:0-Acyl juglone was the strongest inhibitor of DNA repair-related pol λ, as well as the strongest suppression of the production of tumor necrosis factor (TNF)-α production induced by lipopolysaccharide (LPS) in the compounds tested. Moreover, this compound caused the greatest reduction in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ears. C12:0- and C18:1-Acyl juglones selectively inhibited the activities of mammalian pol species, but did not influence the activities of other pols and DNA metabolic enzymes tested. These data indicate that the novel 5-O-acyl juglones target anti-cancer and/or anti-inflammatory agents based on mammalian pol inhibition. Moreover, the results suggest that acylation of juglone is an effective chemical modification to improve the anti-cancer and anti-inflammation of vitamin K3 derivatives, such as juglone.
- Maruo, Sayako,Kuriyama, Isoko,Kuramochi, Kouji,Tsubaki, Kazunori,Yoshida, Hiromi,Mizushina, Yoshiyuki
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experimental part
p. 5803 - 5812
(2011/11/05)
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- FATTY ACID DERIVATIVES OF CATECHINS AND METHODS OF THEIR USE
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The present disclosure relates to fatty acid derivatives of green tea catechins including epicatechin (EC), epicatechin gallate (ECG), epigallocatechin (EGC), epigallocatechin gallate (EGCG) and their epimers (e.g. catechin, catechin gallate, gallocatechi
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Page/Page column 28-29
(2011/10/31)
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- FATTY ACID ACETYLATED SALICYLATES AND THEIR USES
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The invention relates to Fatty Acid Acetylated Salicylate Derivatives; compositions comprising an effective amount of a Fatty Acid Acetylated Salicylate Derivative; and methods for treating or preventing an inflammatory disorder comprising the administration of an effective amount of a Fatty Acid Acetylated Salicylate Derivative.
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Page/Page column 113
(2010/03/04)
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- PLASMALOGEN COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND METHODS FOR TREATING DISEASES OF THE AGING
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Described herein are routes of synthesis and therapeutic uses of 1-alkyl, 2-acyl glycerol derivatives of formula I: which when administered to mammalian biological systems result in increased cellular concentrations of specific sn-2 substituted ethanolamine plasmalogens independent of the ether lipid synthesis capacity of the system. Elevating levels of the specific sn-2 substituted species in this way can cause lowering of membrane cholesterol levels and the lowering of amyloid secretion. These compounds can be used for the treatment or prevention of diseases of aging associated with increased membrane cholesterol, increased amyloid, and decreased plasmalogen levels, such as neurodegeneration (including Alzheimer''s disease, Parkinson''s disease and age-related macular degeneration), cognitive impairment, dementia, cancer (e.g. prostate, lung, breast, ovarian, and kidney cancers), osteoporosis, bipolar disorder and vascular diseases (such as atherosclerosis, hypercholesterolemia).
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Page/Page column 30-31; 39
(2010/07/09)
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- NOVEL ALIPHATIC COMPOUND, METHOD OF SYNTHESIS, AND METHOD OF UTILIZATION
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The present invention relates to aliphatic compounds of the formula I, or stereoisomers thereof, or their pharmaceutically acceptable salts: wherein A represents an optionally substituted CH3CnH(2n-2m)- (wherein n denotes an integer of 4 to 22, and m represents an unsaturation number which is an integer of 0 to 7), 1 represents an integer of 0 to 10, s represents 0 or 1, provided that when s is 0, p+q = 4 or 5, but when s is 1, p+q = 3 or 4, and in each case, either p or q is an integer of 1 or more, R represents an alkyl group having 1 to 10 carbon atoms which may be straight-chain or branched-chain, and RA represents hydrogen or an alkyl group having 1 to 10 carbon atoms which may be straight-chain or branched-chain, and their use in suppression of platelet aggregation, in suppression of inflammation, and in prevention and treatment of circulatory diseases.
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- Syntheses of some polyunsaturated trifluoromethyl ketones as potential phospholipase A2 inhibitors
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The trifluoroketones were prepared as potential inhibitors of cPLA2. Reacting the alcohol with the bromoketone in dichloromethane as solvent and in the presence of silver oxide gave the epoxide. Oxidation with periodinane afforded the desired trifluoroketone in good yield. The presence of a strong broad band due to the OH stretching vibration in the infrared spectrum showed that the compound was formed essentially as the hydrate.
- Holmeide, Anne Kristin,Skattebol, Lars
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p. 2271 - 2276
(2007/10/03)
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- Polyunsaturated fatty acid anilides as inhibitors of acyl- COA:Cholesterol acyltransferase (ACAT)
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A series of polyunsaturated fatty acid anilides were synthesized and evaluated as ACAT inhibitors. Compound 24 had potent inhibitory activity against microsomal ACAT derived from U937, HepG2 and Caco-2 cell lines. Therefore, it might be expected to act as an antiarteriosclerotic and hypocholesterolemic agent. Interestingly, the ACAT inhibitory potency of 24 varied significantly depending on the source of the enzyme.
- Matsuyama, Naoto,Kosaka, Tetsuya,Fukuhara, Mina,Soda, Yasuji,Mizuno, Koji
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p. 2039 - 2042
(2007/10/03)
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