- Antioxidative Properties and Chemical Changes of Quercetin in Fish Oil: Quercetin Reacts with Free Fatty Acids to Form Its Ester Derivatives
-
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
-
p. 1057 - 1067
(2021/02/01)
-
- Preparation of Quercetin Esters and Their Antioxidant Activity
-
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
-
p. 10653 - 10659
(2019/10/19)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF IRRITABLE BOWEL SYNDROME
-
The disclosures herein provide compounds of formula I, formula II, formula III, formula IV, formula V, formula VI, formula VII, formula VIII, formula IX, formula X, formula XI, formula XII, formula XIII, formula XIV and formula XV or its pharmaceutical acceptable salts, as well as polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These salts may be formulated as pharmaceutical compositions. The pharmaceutical compositions may be formulated for oral administration, suppository, transdermal, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of irritable bowel syndrome (IBS), inflammatory bowel diseases or its associated complications.
- -
-
-
- Discovery of Hydrolysis-Resistant Isoindoline N -Acyl Amino Acid Analogues that Stimulate Mitochondrial Respiration
-
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.
-
supporting information
p. 3224 - 3230
(2018/04/23)
-
- Lipophilization of resveratrol and effects on antioxidant activities
-
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
-
p. 8617 - 8625
(2017/11/09)
-
- Compositions and methods for the treatment of inflammatory bowel disease
-
The invention relates to the compounds of formula I and formula II or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I or formula II; and methods for treating or preventing inflammatory bowel disease may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of gastrointestinal diseases and inflammation such as inflammatory bowel disease, ulcerative colitis, mild-to-moderate Crohn's disease, rheumatoid arthritis, inflammatory arthritis, psoriatic arthritis, liver cirrhosis and idiopathic urticaria.
- -
-
-
- Compositions and methods for the treatment of metabolic syndrome
-
The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of fo
- -
-
Page/Page column 25-28; 29-31
(2016/06/01)
-
- Antiphlogistic enteropathy and method for treating dermatopathy compsn.
-
The invention relates to the compounds of formula I and formula II or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I or formula II; and methods for treating or preventing inflammatory bowel disease may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of gastrointestinal diseases and inflammation such as inflammatory bowel disease, ulcerative colitis, mild-to-moderate Crohn's disease, rheumatoid arthritis, inflammatory arthritis, psoriatic arthritis, liver cirrhosis and idiopathic urticaria.
- -
-
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATORY DISORDERS
-
The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for treating or preventing inflammatory disorders may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of intermittent claudication resulting from obstructed arteries in the limbs, and vascular dementia, improves blood flow through peripheral blood vessels and therefore helps with blood circulation in the arms and legs (e.g. intermittent claudication), and the brain (hence its use in vascular dementia), venous disease, Peyronie's disease, neuropathic injuries, strokes, sickle cell disease, nausea and headaches in the mountains (altitude sickness), non-alcoholic steatohepatitis and alcoholic liver disease, fibrotic lesions induced by radiation therapy for breast cancer, cytokine release syndrome, cancer, type 1 diabetes and type 2 diabetes, asthma, bronchodilation, kidney diseases, renal protection, vascular ischemia, neuroprotection, vasodilation, Alzheimer's disease, dementia, stroke, and treatment of endometriosis.
- -
-
Paragraph 0113; 0114
(2015/05/05)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATION
-
The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of inflammation may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of Type II diabetes, Type I diabetes, insulin resistance, cardiovascular disease, arrhythmia, atherosclerosis, coronary artery disease, hypertriglyceridemia, dyslipidemia, retinopathy, nephropathy, neuropathy, macular adema, arthritis, osteoarthritis, rheumatoid arthritis, inflammatory bowel syndrome, neudegeneration, Alzheimer's disease, Huntington's disease, Ulcerative colitis, Crohn's disease, Multiple Sclerosis, muscular dystropthy, metabolic syndrome, fatty liver, bone diseases, inflammatory diseases.
- -
-
Paragraph 0112; 0123; 0124
(2015/06/03)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF AUTONOMIC AND OTHER NEUROLOGICAL DISORDERS
-
The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of autonomic and other neurological disorders may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of neurogenic orthostatic hypotension (NOH), as well as NOH associated with multiple system atrophy (MSA), familial amyloid polyneuropathy (FAP), pure autonomic failure (PAF), and Parkinson's disease (PD), intradialytic hypotension (IDH) or hemodialysis-induced hypotension, hypotension associated with fibromyalgia syndrome (FMS) and chronic fatigue syndrome (CFS).
- -
-
Paragraph 0120; 0121
(2015/08/04)
-
- MULTI-DAY DELIVERY OF BIOLOGICALLY ACTIVE SUBSTANCES
-
Compositions and methods for modifying biologically active substances to achieve multi-day delivery of such substances, particularly through oral or parenteral administration, are disclosed. The compositions include the biologically active substance conjugated to a carrier having a suitably long half life, typically more than one day, wherein the conjugate optionally contains a spacer linking the carrier to the biologically active substance. Pharmaceutical formulations of the conjugates are also disclosed, as are methods of extending delivery of a single dose of a biologically active substance for more than one day.
- -
-
Paragraph 0113
(2015/09/22)
-
- DNA SYNTHASE INHIBITOR
-
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
- -
-
Paragraph 0122-0124
(2016/10/10)
-
- ASCORBATE ESTERS OF OMEGA-3 FATTY ACIDS
-
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.
- -
-
Page/Page column 17-18
(2014/09/16)
-
- FATTY ACID ANTICANCER DERIVATIVES AND THEIR USES
-
The invention relates to fatty acid anticancer derivatives; compositions comprising an effective amount of a fatty acid anticancer derivative; and methods for treating or preventing cancer comprising the administration of an effective amount of a fatty ac
- -
-
Paragraph 0316-0317
(2015/01/07)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATORY DISORDERS
-
The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for treating or preventing inflammatory disorders may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of intermittent claudication resulting from obstructed arteries in the limbs, and vascular dementia, improves blood flow through peripheral blood vessels and therefore helps with blood circulation in the arms and legs (e.g. intermittent claudication), and the brain (hence its use in vascular dementia), venous disease, Peyronie's disease, neuropathic injuries, strokes, sickle cell disease, nausea and headaches in the mountains (altitude sickness), non-alcoholic steatohepatitis and alcoholic liver disease, fibrotic lesions induced by radiation therapy for breast cancer, cytokine release syndrome, cancer, type 1 diabetes and type 2 diabetes, asthma, bronchodilation, kidney diseases, renal protection, vascular ischemia, neuroprotection, vasodilation, Alzheimer's disease, dementia, stroke, and treatment of endometriosis.
- -
-
Paragraph 00100; 00101
(2013/12/03)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF MODERATE TO SEVERE PAIN
-
The invention relates to the compounds of formula (I) and formula (II) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I) or formula (II), and methods for treating or preventing or modulating moderate to severe pain in a disease may be formulated for oral buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of pain, severe pain, chronic pain, chemotherapy induced pain, epilepsy, glaucoma, arthritis, tooth aches, inflammation, musculoskeletal pain, sciatica, radiculopathy pain, migraine, neuropathic pain, post herpetic neuralgia, neuralgia pain, multiple sclerosis, multiple sclerosis, restless legs syndrome (RLS), cluster headache, depression, fibromyalgia, amyotrophic lateral sclerosis (ALS), convulsions, partial seizures, mood-stabilizing agent and bipolar disorder.
- -
-
Paragraph 0097; 00106; 00107
(2013/12/03)
-
- COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATION
-
The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of inflammation may he formulated for oral buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of Type II diabetes, Type I diabetes, insulin resistance, cardiovascular disease, arrhythmia, atherosclerosis, coronary artery disease, hypertriglyceridemia, dyslipidemia, retinopathy, nephropathy, neuropathy, macular adema, arthritis, osteoarthritis, rheumatoid arthritis, inflammatory bowel syndrome, neudegeneration, Alzheimer's disease, Huntington's disease. Ulcerative colitis, Crohn's disease. Multiple Sclerosis, muscular dystropthy, metabolic syndrome, fatty liver, bone diseases, inflammatory diseases.
- -
-
Paragraph 0094; 00105; 00106
(2013/12/03)
-
- Analogs of 2-arachidonoylglycerin containing the no-donor group
-
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
-
p. 367 - 370
(2012/10/30)
-
- Improved LC-MS method for the determination of fatty acids in red blood cells by LC-orbitrap MS
-
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.
-
experimental part
p. 3192 - 3198
(2011/11/04)
-
- Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response
-
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
-
experimental part
p. 5803 - 5812
(2011/11/05)
-
- FATTY ACID DERIVATIVES OF CATECHINS AND METHODS OF THEIR USE
-
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
- -
-
Page/Page column 28-29
(2011/10/31)
-
- Self-assembling structures of long-chain sugar-based amphiphiles influenced by the introduction of double bonds
-
Nine phenyl glucoside or galactoside amphiphiles possessing a saturated or unsaturated long alkyl-chain group as the self-assembling unit of a highly organized molecular architecture were synthesized. Their self-assembly properties were investigated by using energy-filtering TEM (EF-TEM), SEM, CD, XRD, and FT-IR techniques. Compound 2, possessing one cis double bond in the lipophilic portion, exhibited twisted helical fibers, which formed a bilayered structure with a 3.59 nm period, while 3 exhibited helical ribbons and left-handed nanotubu-lar structures with 150-200 nm inner diameters and a wall thickness of approximately 20 nm. Very interestingly, 4, possessing three cis double bonds, exhibited a nanotubular structure with an inner diameter of approximately 70 nm and a d spacing value of 4.62 nm. On the other hand, 7, possessing two trans double bonds in the lipophilic region, exhibited crystal- or plate-like structures, which formed a bilayer structure with a d spacing value of 3.93 nm. These results indicate that the self-assembly properties are strongly dependent on the type of double bond. Furthermore, 8 and 9, with the galactopyr anose moiety, revealed helical ribbon and well-defined double helical fiber structures, respectively. These findings support the view that the orientation of the intermolecular hydrogen-bonding interaction between the sugar moieties plays a critical role in producing the nanotubular structures. According to CD and powder XRD experiments, the relatively strong intermolecular hydrogen-bonding interaction of the glucopyranoside moiety in 3 and 4 provided a highly ordered chiral packing structure. Even though these compounds formed a weak hydrophobic interaction between lipophilic groups, it led to the formation of the nanotubular structure.
- Jung, Jong Hwa,Do, Youngkyu,Lee, Young-A.,Shimizu, Toshimi
-
p. 5538 - 5544
(2007/10/03)
-
- Polyunsaturated fatty acid anilides as inhibitors of acyl- COA:Cholesterol acyltransferase (ACAT)
-
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
-
p. 2039 - 2042
(2007/10/03)
-