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Alpha-Hydroxy acid

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61. Cholesteryl esters of ω-(O-acyl)-hydroxy fatty acids in vernix caseosa (Full text)

Cholesteryl esters of ω-(O-acyl)-hydroxy fatty acids in vernix caseosa Cholesteryl esters of ω-(O-acyl)-hydroxy FAs (Chl-ωOAHFAs) were identified for the first time in vernix caseosa and characterized using chromatography and MS. Chl-ωOAHFAs were isolated using adsorption chromatography on silica gel and magnesium hydroxide. Their general structure was established using high-resolution and tandem MS of intact lipids, and products of their transesterification and derivatizations. Individual (...) molecular species were characterized using nonaqueous reversed-phase HPLC coupled to atmospheric pressure chemical ionization. The analytes were detected as protonated molecules, and their structures were elucidated in the negative ion mode using controlled thermal decomposition and data-dependent fragmentation. About three hundred molecular species of Chl-ωOAHFAs were identified in this way. The most abundant Chl-ωOAHFAs contained 32:1 ω-hydroxy FA (ω-HFA) and 14:0, 15:0, 16:0, 16:1, and 18:1 FAs

2017 Journal of lipid research PubMed

62. Oxidation of C18 Hydroxy-Polyunsaturated Fatty Acids to Epoxide or Ketone by Catalase-Related Hemoproteins Activated with Iodosylbenzene (Full text)

Oxidation of C18 Hydroxy-Polyunsaturated Fatty Acids to Epoxide or Ketone by Catalase-Related Hemoproteins Activated with Iodosylbenzene Small catalase-related hemoproteins with a facility to react with fatty acid hydroperoxides were examined for their potential mono-oxygenase activity when activated using iodosylbenzene. The proteins tested were a Fusarium graminearum 41 kD catalase hemoprotein (Fg-cat, gene FGSG_02217), a Pseudomonas fluorescens Pfl01 catalase (37.5 kD, accession number (...) WP_011333788.1), and a Mycobacterium avium ssp. paratuberculosis 33 kD catalase (gene MAP-2744c). 13-Hydroxy-octadecenoic acids (which are normally unreactive) were selected as substrates because these enzymes react specifically with the corresponding 13S-hydroperoxides (Pakhomova et al. 18:2559-2568, 5; Teder et al. 1862:706-715, 14). In the presence of iodosylbenzene Fg-cat converted 13S-hydroxy-fatty acids to two products: the 15,16-double bond of 13S-hydroxy α-linolenic acid was oxidized

2017 Lipids PubMed

63. Anti-allergic Hydroxy Fatty Acids from Typhonium blumei Explored through ChemGPS-NP (Full text)

Anti-allergic Hydroxy Fatty Acids from Typhonium blumei Explored through ChemGPS-NP Increasing prevalence of allergic diseases with an inadequate variety of treatment drives forward search for new alternative drugs. Fatty acids, abundant in nature, are regarded as important bioactive compounds and powerful nutrients playing an important role in lipid homeostasis and inflammation. Phytochemical study on Typhonium blumei Nicolson and Sivadasan (Araceae), a folk anti-cancer and anti-inflammatory (...) medicine, yielded four oxygenated fatty acids, 12R-hydroxyoctadec-9Z,13E-dienoic acid methyl ester (1) and 10R-hydroxyoctadec-8E,12Z-dienoic acid methyl ester (2), 9R-hydroxy-10E-octadecenoic acid methyl ester (3), and 12R*-hydroxy-10E-octadecenoic acid methyl ester (4). Isolated compounds were identified by spectroscopic methods along with GC-MS analysis. Isolated fatty acids together with a series of saturated, unsaturated and oxygenated fatty acids were evaluated for their anti-inflammatory and anti

2017 Frontiers in pharmacology PubMed

64. Synthesis of Cyclooxygenase Metabolites of 8,9-Epoxyeicosatrienoic Acid (EET): 11- and 15-Hydroxy 8,9-EETs (Full text)

Synthesis of Cyclooxygenase Metabolites of 8,9-Epoxyeicosatrienoic Acid (EET): 11- and 15-Hydroxy 8,9-EETs COX metabolites of 8,9-EET, previously observed as potent mitogenic lipid mediators, were synthesized for the first time by using two synthetic approaches. These synthetic materials allow for structural confirmation of COX metabolites of 8,9-EET and further study of their biological roles.

2017 Organic & biomolecular chemistry PubMed

65. 10-Hydroxy-2-decenoic acid, a natural product, improves hyperglycemia and insulin resistance in obese/diabetic KK-Ay mice, but does not prevent obesity (Full text)

10-Hydroxy-2-decenoic acid, a natural product, improves hyperglycemia and insulin resistance in obese/diabetic KK-Ay mice, but does not prevent obesity 10-Hydroxy-2-decenoic acid (10H2DA) is a fatty acid found in royal jelly (RJ). In healthy mice, it activates 5'-AMP-activated protein kinase (AMPK) and increases glucose transporter 4 (GLUT4) translocation. Therefore, we examined whether 10H2DA has a potential therapeutic effect against type 2 diabetes in obese/diabetic KK-Ay mice. 10H2DA (3 mg (...) in skeletal muscles; however, this expression did not correlate with increased GLUT4 translocation. Furthermore, 10H2DA neither enhanced the expression of adiponectin receptor mRNA nor activated the insulin signaling cascade, such as GSK-3β phosphorylation, in the liver. We found that 10H2DA-treated mice had a significant increase in the expression of peroxisome proliferator-activated receptor gamma coactivator 1 alpha (Pgc-1α) mRNA in skeletal muscles compared with non-treated group (P=0.0024

2017 The Journal of Veterinary Medical Science PubMed

66. A role for lipids as agents to alleviate stroke damage: the neuroprotective effect of 2-hydroxy arachidonic acid (Full text)

A role for lipids as agents to alleviate stroke damage: the neuroprotective effect of 2-hydroxy arachidonic acid 28966640 2018 11 13 1673-5374 12 8 2017 Aug Neural regeneration research Neural Regen Res A role for lipids as agents to alleviate stroke damage: the neuroprotective effect of 2-hydroxy arachidonic acid. 1273-1275 10.4103/1673-5374.213545 Ugidos Irene F IF 0000-0002-3727-0544 Área de Biología Celular, Instituto de Biomedicina, Universidad de León, León, Spain. Pérez-Rodríguez Diego D

2017 Neural Regeneration Research PubMed

67. 2-Hydroxy-4-Methylselenobutanoic Acid as New Organic Selenium Dietary Supplement to Produce Selenium-Enriched Eggs. (PubMed)

2-Hydroxy-4-Methylselenobutanoic Acid as New Organic Selenium Dietary Supplement to Produce Selenium-Enriched Eggs. Food-based strategies need to be developed to improve the selenium (Se) status of individuals. The aim of this study was to evaluate the effects of a new organic Se [2-hydroxy-4-methylselenobutanoic acid (HMSeBA)] on selected performance criteria and Se deposition in egg of laying hens. Isa Brown laying hens, 18 weeks of age were randomly allocated to two dietary treatments (...) and fed for 10 weeks. The hens were fed two corn-soybean meal-based diets comprising a control basal diet without Se supplementation and a test diet supplemented with Se at 0.2 mg/kg from HMSeBA. No difference was observed among dietary treatments on feed intake, egg weight and laying rate, whereas egg yolk fatty acid profile and vitamin E content were positively influenced by HMSeBA supplementation. Hens fed Se-supplemented diet exhibited greater (P < 0.001) egg yolk total Se contents, which averaged

2017 Biological trace element research

68. On the importance of albumin binding for the flux of 7α-hydroxy-3-oxo-4-cholestenoic acid in the brain (Full text)

On the importance of albumin binding for the flux of 7α-hydroxy-3-oxo-4-cholestenoic acid in the brain We confirmed previous findings by a Japanese group that there is an accumulation of 7α-hydroxy-3-oxo-4-cholestenoic acid (7-Hoca) in human subdural hematomas. The accumulation correlated with the time from the bleeding to the sample collection. We present evidence that these accumulations are likely to be caused by the strong affinity of 7-Hoca to albumin and the marked difference between (...) plasma and brain with respect to levels of albumin. In the circulation, 80-90% of 7-Hoca is bound to albumin with a ratio between the steroid acid and albumin of ∼1.4 ng/mg. In cerebrospinal fluid (CSF), the ratio between 7-Hoca and albumin is ∼30 ng/mg. When albumin or hemolyzed blood in a dialysis bag was exposed to CSF, there was a flux of 7-Hoca from CSF to the albumin. We suggest that the major explanation for accumulation of 7-Hoca in subdural hematoma is a flux from the brain into the hematoma

2017 Journal of lipid research PubMed

69. Inhibition of breast cancer cell growth by the Pteris semipinnata extract ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (Full text)

Inhibition of breast cancer cell growth by the Pteris semipinnata extract ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid Previous studies have demonstrated strong anti-tumor effects of ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid (5F), an extract from Pteris semipinnata, in liver, lung, stomach and anaplastic thyroid cancer cells. However, whether 5F inhibits the growth of breast cancer cells remains unclear. The present study assessed the effect of 5F on breast cancer cells. The breast cancer

2017 Oncology letters PubMed

70. An L-threonine transaldolase is required for L-threo-β-hydroxy-α-amino acid assembly during obafluorin biosynthesis (Full text)

An L-threonine transaldolase is required for L-threo-β-hydroxy-α-amino acid assembly during obafluorin biosynthesis β-Lactone natural products occur infrequently in nature but possess a variety of potent and valuable biological activities. They are commonly derived from β-hydroxy-α-amino acids, which are themselves valuable chiral building blocks for chemical synthesis and precursors to numerous important medicines. However, despite a number of excellent synthetic methods for their asymmetric (...) enzyme family and identifies further gene clusters encoding L-threonine transaldolases. We also present preliminary data suggesting that L-threonine transaldolases might be useful for the preparation of L-threo-β-hydroxy-α-amino acids.

2017 Nature communications PubMed

71. Branched Fatty Acid Esters of Hydroxy Fatty Acids are Preferred Substrates of the MODY8 Protein Carboxyl Ester Lipase (Full text)

Branched Fatty Acid Esters of Hydroxy Fatty Acids are Preferred Substrates of the MODY8 Protein Carboxyl Ester Lipase A recently discovered class of endogenous mammalian lipids, branched fatty acid esters of hydroxy fatty acids (FAHFAs), possesses anti-diabetic and anti-inflammatory activities. Here, we identified and validated carboxyl ester lipase (CEL), a pancreatic enzyme hydrolyzing cholesteryl esters and other dietary lipids, as a FAHFA hydrolase. Variants of CEL have been linked

2016 Biochemistry PubMed

72. Branched Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) Protect against Colitis by Regulating Gut Innate and Adaptive Immune Responses (Full text)

Branched Fatty Acid Esters of Hydroxy Fatty Acids (FAHFAs) Protect against Colitis by Regulating Gut Innate and Adaptive Immune Responses We recently discovered a structurally novel class of endogenous lipids, branched palmitic acid esters of hydroxy stearic acids (PAHSAs), with beneficial metabolic and anti-inflammatory effects. We tested whether PAHSAs protect against colitis, which is a chronic inflammatory disease driven predominantly by defects in the innate mucosal barrier and adaptive

2016 The Journal of biological chemistry PubMed

73. A liquid chromatography–mass spectrometry-based workflow for measurement of branched Fatty Acid esters of Hydroxy Fatty Acids (FAHFAs) (Full text)

A liquid chromatography–mass spectrometry-based workflow for measurement of branched Fatty Acid esters of Hydroxy Fatty Acids (FAHFAs) Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are a recently discovered class of endogenous mammalian lipids with antidiabetic and anti-inflammatory effects. We previously identified 16 different FAHFA families, such as branched palmitic acid esters of hydroxy stearic acids (PAHSAs); each family consists of multiple isomers in which the branched

2016 Nature protocols PubMed

74. HadD, a novel fatty acid synthase type II protein, is essential for alpha- and epoxy-mycolic acid biosynthesis and mycobacterial fitness (Full text)

HadD, a novel fatty acid synthase type II protein, is essential for alpha- and epoxy-mycolic acid biosynthesis and mycobacterial fitness Mycolic acids (MAs) have a strategic location within the mycobacterial envelope, deeply influencing its architecture and permeability, and play a determinant role in the pathogenicity of mycobacteria. The fatty acid synthase type II (FAS-II) multienzyme system is involved in their biosynthesis. A combination of pull-downs and proteomics analyses led (...) to the discovery of a mycobacterial protein, HadD, displaying highly specific interactions with the dehydratase HadAB of FAS-II. In vitro activity assays and homology modeling showed that HadD is, like HadAB, a hot dog folded (R)-specific hydratase/dehydratase. A hadD knockout mutant of Mycobacterium smegmatis produced only the medium-size alpha'-MAs. Data strongly suggest that HadD is involved in building the third meromycolic segment during the late FAS-II elongation cycles, leading to the synthesis

2018 Scientific reports PubMed

75. 2-Bromopalmitate targets retinoic acid receptor alpha and overcomes all-trans retinoic acid resistance of acute promyelocytic leukemia. (Full text)

2-Bromopalmitate targets retinoic acid receptor alpha and overcomes all-trans retinoic acid resistance of acute promyelocytic leukemia. Fatty acid oxidation dependency of leukemia cells has been documented in recent studies. Pharmacologic inhibition of fatty acid oxidation, thereby, displays significant effects in suppressing leukemia. 2-Bromopalmitate, a palmitate analogue, was initially identified as an inhibitor of fatty acid oxidation, and recently recognized as an inhibitor of protein (...) binds at cysteine 105 and cysteine 174 of retinoic acid receptor alpha (RARα) and stabilizes RARα protein in the presence of all-trans retinoic acid which is known to induce RARα degradation, leading to enhanced transcription of RARα-target genes. Mutation of both cysteines largely abrogates the synergistic effect of 2-Bromopalmitate on all-trans retinoic acid-induced differentiation, demonstrating that 2-Bromopalmitate promotes all-trans retinoic acid-induced differentiation through binding RARα

2018 Haematologica PubMed

76. Effect of alpha-lipoic acid on asymmetric dimethylarginine and disability in multiple sclerosis patients: A randomized clinical trial (Full text)

Effect of alpha-lipoic acid on asymmetric dimethylarginine and disability in multiple sclerosis patients: A randomized clinical trial Multiple Sclerosis (MS) is an inflammatory and demyelinating disease of the central nervous system. Oxidative stress plays a major role in the onset and progression of MS. Asymmetric dimethylarginine (ADMA) formation is dependent on oxidative stress status.We examined whether alpha-lipoic acid (ALA) as a potent antioxidant could improve the Expanded Disability

2017 Electronic physician PubMed

77. Metabolomics analysis of serum 25-hydroxy-vitamin D in the Alpha-Tocopherol, Beta-Carotene Cancer Prevention (ATBC) Study (Full text)

Metabolomics analysis of serum 25-hydroxy-vitamin D in the Alpha-Tocopherol, Beta-Carotene Cancer Prevention (ATBC) Study Vitamin D has been discussed in the context of cardiovascular disease, cancer, bone health and other outcomes. Epidemiological studies have reported on the importance of vitamin D in cancer prevention and treatment. The discovery of vitamin D-associated metabolites through agnostic metabolomics analyses offers a new approach for elucidating disease aetiology and health (...) -related pathway identification.Baseline serum 25-hydroxy-vitamin D [25(OH)D] and 940 serum metabolites were measured in 392 men from eight nested cancer case-control studies in the Alpha-Tocopherol, Beta-Carotene Cancer Prevention Study of Finnish male smokers (aged 50-69 years). The metabolomic profiling was conducted using mass spectrometry. We used linear regression to estimate the standardized beta-coefficient as the effect metric for the associations between metabolites and 25(OH)D levels.A

2016 International journal of epidemiology PubMed

78. Effect of alpha-linolenic acid in combination with the flavonol quercetin on markers of cardiovascular disease risk in healthy, non-obese adults: A randomized, double-blinded placebo-controlled crossover trial. (PubMed)

Effect of alpha-linolenic acid in combination with the flavonol quercetin on markers of cardiovascular disease risk in healthy, non-obese adults: A randomized, double-blinded placebo-controlled crossover trial. Alpha-linolenic acid (ALA) and quercetin are characteristic compounds in plant-based diets. Cardioprotective effects have been described for both substances, although a possible benefit of combining ALA and quercetin has not, to our knowledge, been evaluated yet. The aim of this study (...) cholesterol, low-density lipoprotein cholesterol, non-high-density lipoprotein cholesterol, and apolipoprotein B to a similar extent. No effect on high-density lipoprotein cholesterol, apolipoprotein A1, glucose, uric acid, oxidized low-density lipoprotein, C-reactive protein, or lipid-adjusted retinol, α-tocopherol, or β-carotene was seen in either group.Although dietary supplements of 3.6 g/d ALA over an 8-wk period improved lipid profiles in healthy adults, antioxidative and oxidative status

2019 Nutrition (Burbank, Los Angeles County, Calif.)

79. Reduction in maternal serum values of glucose and gamma-glutamyltransferase after supplementation with alpha-lipoic acid in women with gestational diabetes mellitus. (PubMed)

Reduction in maternal serum values of glucose and gamma-glutamyltransferase after supplementation with alpha-lipoic acid in women with gestational diabetes mellitus. Alpha-lipoic acid (ALA) is a short chain fatty acid which has a key role in energy production. ALA is also known as a universal antioxidant. The aim of the present study was to explore the effects of ALA supplementation in women with gestational diabetes mellitus.A randomized double-blind placebo-controlled clinical trial study (...) decreased in the drug group after the intervention. However, values of urea, creatinine, uric acid, aspartate transaminase and alkaline phosphatase were not changed significantly after the trial.The present study has shown that supplementation with 100 mg/day of ALA had some beneficial effects on glucose metabolism and liver function in women with gestational diabetes mellitus.© 2018 Japan Society of Obstetrics and Gynecology.

2019 The journal of obstetrics and gynaecology research

80. Glycoprotein Ib clustering in platelets can be inhibited by alpha-linolenic acid as revealed by cryo-electron tomography. (PubMed)

Glycoprotein Ib clustering in platelets can be inhibited by alpha-linolenic acid as revealed by cryo-electron tomography. Platelet adhesion to the sub-endothelial matrix and damaged endothelium occurs through a multi-step process mediated in the initial phase by glycoprotein Ib binding to von Willebrand factor, which leads to the subsequent formation of a platelet plug. The plant-derived omega-3 fatty acid alpha-linolenic acid is an abundant alternative to fish-derived n-3 FA and has anti (...) -inflammatory and anti-thrombotic properties. In this study, we investigated the impact of alpha-linolenic acid on human platelet binding to vWF under high-shear flow conditions (mimicking blood flow in stenosed arteries). Pre-incubation of fresh human blood from healthy donors with alpha-linolenic acid at dietary relevant concentrations reduced platelet binding and rolling on vWF-coated microchannels at a shear rate of 100 dyn/cm2. Depletion of membrane cholesterol by incubation of platelet-rich-plasma

2019 Haematologica

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