21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

Code of Federal Regulations, 2010 CFR

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl and ethyl esters of fatty acids produced... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

Code of Federal Regulations, 2011 CFR

2011-04-01

... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl and ethyl esters of fatty acids produced... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

Marine Omega-3 Phospholipids: Metabolism and Biological Activities

PubMed Central

Burri, Lena; Hoem, Nils; Banni, Sebastiano; Berge, Kjetil

2012-01-01

The biological activities of omega-3 fatty acids (n-3 FAs) have been under extensive study for several decades. However, not much attention has been paid to differences of dietary forms, such as triglycerides (TGs) versus ethyl esters or phospholipids (PLs). New innovative marine raw materials, like krill and fish by-products, present n-3 FAs mainly in the PL form. With their increasing availability, new evidence has emerged on n-3 PL biological activities and differences to n-3 TGs. In this review, we describe the recently discovered nutritional properties of n-3 PLs on different parameters of metabolic syndrome and highlight their different metabolic bioavailability in comparison to other dietary forms of n-3 FAs. PMID:23203133

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2014 CFR

2014-07-01

...[(heptadecafluorooctyl)sulfonyl]amino]ethyl]-.omega.-hydroxy- 29457-72-5 1-Octanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,6,6,7...-octanethiol and .alpha.-(1-oxo-2-propenyl)-.omega.-methoxypoly(oxy-1,2-ethanediyl) 68891-96-3 Chromium...[(heptadecafluorooctyl)sulfonyl]amino]ethyl]-.omega.-methoxy- 70225-14-8 1-Octanesulfonic acid, 1,1,2,2,3,3,4,4,5,5,6,6,7...

A novel self-micro-emulsifying delivery system (SMEDS) formulation significantly improves the fasting absorption of EPA and DHA from a single dose of an omega-3 ethyl ester concentrate.

PubMed

Qin, Yan; Nyheim, Hilde; Haram, Else Marie; Moritz, Joseph M; Hustvedt, Svein Olaf

2017-10-16

Absorption of EPA and DHA from Omega-3-acid ethyl ester (EE) concentrate supplements occurs most efficiently when taken in context of a fatty meal; adequate fat intake is required to release bile salts that emulsify and pancreatic enzymes that digest omega-3-containing lipids in the intestine. Current guidelines recommend reduction in fat intake and therefore there is a need to optimize the absorption of Omega-3 in those consuming low-fat or no-fat meals. To this end, BASF has developed an Absorption Acceleration Technology, a novel self-micro-emulsifying delivery system (SMEDS) formulation of highly concentrated Omega-3-acid EE which enables rapid emulsification and microdroplet formation upon entering the aqueous environment of the gut therefore enhances the absorption. Two separate single dose, crossover studies were conducted to determine the relative bioavailability of omega-3-acid EE concentrate, either as a novel SMEDS formulation (PRF-021) or as control, in healthy fasted male and female adults at two dose levels (Study 1 "low dose": 630 mg EPA + DHA in PRF-021 vs. 840 mg EPA + DHA in control; Study 2 "high dose": 1680 mg EPA + DHA in PRF-021 vs. 3360 mg EPA + DHA in control). Blood samples were collected immediately before supplementation and at defined time intervals for 48 h. Plasma concentration of total EPA and DHA were determined for pharmacokinetic analysis, area under the curve (AUC) and maximum observed concentration (C max ) was determined. Total EPA plus DHA absorption from SMEDS formulation PRF-021 were 6.4 and 11.5 times higher compared to control in low- and high-dose studies respectively, determined as the ratio of baseline corrected, dose normalized AUC 0-24h of PRF-021 over that of control. EPA and DHA individually showed differing levels of enhancement: the AUC 0-24h ratio for EPA was 23.8 and 25.7 in low and high dose studies, respectively, and the AUC 0-24h ratio for DHA was 3.6 and 5.6 in low and high dose studies, respectively. C max was also increased for both EPA and DHA 2.7- to 9.2-fold. PRF-021 is a novel SMEDS formulation of Omega-3-acid EE demonstrating a marked improvement in absorption of a single dose of EPA and DHA EE under fasted conditions. This allows adequate absorption of Omega-3 from the supplement without the requirement of a high-fat meal.

Usefulness of Icosapent Ethyl (Eicosapentaenoic Acid Ethyl Ester) in Women to Lower Triglyceride Levels (Results from the MARINE and ANCHOR Trials).

PubMed

Mosca, Lori; Ballantyne, Christie M; Bays, Harold E; Guyton, John R; Philip, Sephy; Doyle, Ralph T; Juliano, Rebecca A

2017-02-01

There are limited data on the efficacy and safety of triglyceride (TG)-lowering agents in women. We conducted subgroup analyses of the effects of icosapent ethyl (a high-purity prescription form of the ethyl ester of the omega-3 fatty acid, eicosapentaenoic acid) on TG levels (primary efficacy variable) and other atherogenic and inflammatory parameters in a total of 215 women with a broad range of TG levels (200-2000 mg/dl) enrolled in two 12-week placebo-controlled trials: MARINE (n = 18; placebo, n = 18) and ANCHOR (n = 91; placebo, n = 88). Icosapent ethyl 4 g/day significantly reduced TG levels from baseline to week 12 versus placebo in both MARINE (-22.7%; p = 0.0327) and ANCHOR (-21.5%; p <0.0001) without increasing low-density lipoprotein cholesterol levels. Significant improvements were also observed in non-high-density lipoprotein cholesterol levels in MARINE (-15.7%; p = 0.0082) and ANCHOR (-14.2%; p <0.0001) and total cholesterol levels in MARINE (-14.9%; p = 0.0023) and ANCHOR (-12.1%; p <0.0001), along with significant increases of >500% in eicosapentaenoic acid levels in plasma and red blood cells (all p <0.001). Icosapent ethyl was well tolerated, with adverse-event profiles comparable with findings in the overall studies. In conclusion, icosapent ethyl 4 g/day significantly reduced TG levels and other atherogenic parameters in women without increasing low-density lipoprotein cholesterol levels compared with placebo; the clinical implications of these findings are being evaluated in the REDUCtion of Cardiovascular Events With Eicosapentaenoic Acid [EPA]-Intervention Trial (REDUCE-IT) cardiovascular outcomes study. Copyright © 2016 The Author(s). Published by Elsevier Inc. All rights reserved.

Effects of omega-3 fatty acid supplementation on neurocognitive functioning and mood in deployed U.S. soldiers: a pilot study.

PubMed

Dretsch, Michael N; Johnston, Daniel; Bradley, Ryan S; MacRae, Holden; Deuster, Patricia A; Harris, William S

2014-04-01

Omega-3 fatty acids (FAs) may have neuroprotective properties for psychological health and cognition. The objective of this study was to evaluate the effectiveness of omega-3 FAs (eicosapentaenoic + docosahexaenoic; Harris-Schacky [HS]-Omega-3 Index) on neuropsychological functioning among U.S. Soldiers deployed to Iraq. This randomized, double-blind, placebo-controlled trial included Soldiers between the ages of 18 and 55 years who were randomly assigned to either the active treatment group (n = 44) or placebo group (n = 34). Active treatment was 2.5 g per day of eicosapentaenoic + docosahexaenoic (Lovaza; GlaxoSmithKline, Research Triangle Park, North Carolina). The placebo was corn oil ethyl esters. HS-Omega-3 Index, a neurocognitive battery (Central Nervous System-Vital Signs, Morrisville, North Carolina), and psychological health scales were assessed at baseline and after 60 days of treatment. Although the results revealed that omega-3 FAs significantly increased the HS-Omega-3 Index (p = 0.001), there were no significant effects on indices psychological health and neurocognitive functioning by treatment group. Nevertheless, there was a significant inverse correlation between the changes in the HS-Omega-3 Index and daytime sleepiness (r = 0.30, p = 0.009). Short-term treatment with 2.5 g of omega-3 FAs did not alter measures of neurocognition or psychological health, but there was evidence of a relationship between omega-3 levels and daytime sleepiness. Reprint & Copyright © 2014 Association of Military Surgeons of the U.S.

Efficacy and safety of TAK-085 compared with eicosapentaenoic acid in Japanese subjects with hypertriglyceridemia undergoing lifestyle modification: the omega-3 fatty acids randomized double-blind (ORD) study.

PubMed

Tatsuno, Ichiro; Saito, Yasushi; Kudou, Kentarou; Ootake, Jun

2013-01-01

Hypertriglyceridemia is a risk factor for cardiovascular disease, and clinical practice guidelines advocate treatment to reduce triglyceride (TG) levels. In Japan, an EPA-E (eicosapentaenoic acid-ethyl ester) product has been used clinically for treating dyslipidemia. We investigated the TG-lowering effects of TAK-085 (EPA-E + docosahexaenoic acid-ethyl ester) in comparison with EPA-E in Japanese patients with hypertriglyceridemia (TG ≥150 mg/dL and <750 mg/dL). In this multicenter, 12-week, double-blind study, subjects were stratified for coadministration of a 3-hydroxy-3-methyl-glutaryl-CoA reductase inhibitor then randomized to TAK-085 2 g once daily (n = 205), TAK-085 2 g twice daily (n = 210), or EPA-E 0.6 g three times daily (n = 195). Each one gram of fatty acid in TAK-085 contains approximately 465 mg of EPA plus 375 mg of docosahexaenoic acid-ethyl as ethyl esters. Guidance on lifestyle modifications was provided throughout. The primary end point was the percent change in TG levels (baseline from end of treatment), which was -10.8 ± 22.6, -22.9 ± 23.1, and -11.2 ± 25.7 in the TAK-085 2 g/day, TAK-085 4 g/day, and EPA-E 1.8 g/day groups, respectively. TAK-085 4 g/day produced a significantly greater reduction in TG than EPA-E 1.8 g/day (P < .0001), whereas TAK-085 2 g/day was not inferior to EPA-E 1.8 g/day. Changes in other lipid parameters were relatively modest. There were no notable safety or tolerability differences between the groups. In Japanese patients with modest hypertriglyceridemia who also underwent lifestyle intervention, TAK-085 4 g/day reduced TG more than EPA-E 1.8 g/day. TAK-085 2 g/day had similar effects on TG as EPA-E 1.8 g/day. TAK-085 was well-tolerated. Copyright © 2013 National Lipid Association. Published by Elsevier Inc. All rights reserved.

2-Decenoic acid ethyl ester, a derivative of unsaturated medium-chain fatty acids, facilitates functional recovery of locomotor activity after spinal cord injury.

PubMed

Hirakawa, A; Shimizu, K; Fukumitsu, H; Soumiya, H; Iinuma, M; Furukawa, S

2010-12-29

There is increasing evidence that omega-3 polyunsaturated fatty acids (PUFAs) have therapeutic potential in various animal models of neuronal injury. However, very few studies have examined the effect of medium-chain fatty acids (MCFAs) on neuronal injury. So in the present study we synthesized various MCFAs and their derivatives, and found that exposure to trans-2-decenoic acid ethyl ester (DAEE) markedly activated extracellular signal-regulated protein kinases 1 and 2 (ERK1/2) in cultured cortical neurons. Therefore, we examined the effect of DAEE treatment on a rat model of spinal cord injury. DAEE (150 μg/kg body weight) administered after hemisection of the spinal cord resulted in improved functional recovery, decreased the lesion size, increased the activation of ERK1/2, and enhanced the expression of bcl-2 and brain-derived neurotrophic factor (BDNF) mRNA in the injury site of the spinal cord. Furthermore, it also increased neuronal survival after spinal cord injury. These results indicate that the possibility that DAEE will become a promising tool for reducing the secondary damage observed following primary physical injury to the spinal cord. Copyright © 2010 IBRO. Published by Elsevier Ltd. All rights reserved.

Application of ethyl esters and d3-methyl esters as internal standards for the gas chromatographic quantification of transesterified fatty acid methyl esters in food.

PubMed

Thurnhofer, Saskia; Vetter, Walter

2006-05-03

Ethyl esters (FAEE) and trideuterium-labeled methyl esters (d3-FAME) of fatty acids were prepared and investigated regarding their suitability as internal standards (IS) for the determination of fatty acids as methyl esters (FAME). On CP-Sil 88, ethyl esters of odd-numbered fatty acids eluted approximately 0.5 min after the respective FAME, and only coelutions with minor FAME were observed. Depending on the problem, one or even many FAEE can be added as IS for the quantification of FAME by both GC-FID and GC-MS. By contrast, d3-FAME coeluted with FAME on the polar GC column, and the use of the former as IS requires application of GC-MS. In the SIM mode, m/z 77 and 90 are suggested for d3-methyl esters of saturated fatty acids, whereas m/z 88 and 101 are recommended for ethyl esters of saturated fatty acids. These m/z values give either no or very low response for FAME and can thus be used for the analysis of FAME in food by GC-MS in the SIM mode. Fatty acids in sunflower oil and mozzarella cheese were quantified using five saturated FAEE as IS. Gravimetric studies showed that the transesterification procedure could be carried out without of loss of fatty acids. GC-EI/MS full scan analysis was suitable for the quantitative determination of all unsaturated fatty acids in both food samples, whereas GC-EI/MS in the SIM mode was particularly valuable for quantifying minor fatty acids. The novel GC-EI/MS/SIM method using fatty acid ethyl esters as internal standards can be used to quantify individual fatty acids only, that is, without determination of all fatty acids (the common 100% method), although this is present. This was demonstrated by the exclusive quantification of selected fatty acids including methyl-branched fatty acids, erucic acid (18:1n-9trans), and polyunsaturated fatty acids in cod liver oil and goat's milk fat.

Aroma enhancement and enzymolysis regulation of grape wine using β-glycosidase

PubMed Central

Zhu, Feng-Mei; Du, Bin; Li, Jun

2014-01-01

Adding β-glycosidase into grape wine for enhancing aroma was investigated using gas chromatography-mass spectrometry (GC-MS) and Kramer sensory evaluation. Compared with the extract from control wines, the extract from enzyme-treated wines increased more aromatic compounds using steam distillation extraction (SDE) and GC-MS analyses. Theses aromatic compounds were as follows: 3-methyl-1-butanol formate, 3-pentanol, furfural, 3-methyl-butanoic acid, 2-methyl-butanoic acid, 3-hydroxy-butanoic acid ethyl ester, hexanoic acid, hexanoic acid ethyl ester, benzyl alcohol, octanoic acid, octanoic acid ethyl ester, dodecanoic acid, and ethyl ester. The enzymolysis regulation conditions, including enzymolysis temperature, enzymolysis time, and enzyme amount, were optimized through L9(34) orthogonal test. Kramer sensory evaluation was performed by an 11-man panel of judges. The optimum enzymolysis regulation conditions were found to be temperature of 45°C, enzymolysis time of 90 min, and enzyme amount of 58.32 U/mL grape wine, respectively. The Kramer sensory evaluation supported that the enzyme-treated wines produced a stronger fragrance. PMID:24804072

21 CFR 182.60 - Synthetic flavoring substances and adjuvants.

Code of Federal Regulations, 2014 CFR

2014-04-01

... aldehyde). N-Butyric acid (butanoic acid). d- or l-Carvone (carvol). Cinnamaldehyde (cinnamic aldehyde... aldehyde, caprinaldehyde, aldehyde C-10). Ethyl acetate. Ethyl butyrate. 3-Methyl-3-phenyl glycidic acid ethyl ester (ethyl-methyl-phenyl-glycidate, so-called strawberry aldehyde, C-16 aldehyde). Ethyl...

Effects of MAT9001 containing eicosapentaenoic acid and docosapentaenoic acid, compared to eicosapentaenoic acid ethyl esters, on triglycerides, lipoprotein cholesterol, and related variables.

PubMed

Maki, Kevin C; Bobotas, George; Dicklin, Mary R; Huebner, Margie; Keane, William F

Long-chain omega-3 fatty acid concentrate pharmaceuticals are used in the United States for treatment of severe hypertriglyceridemia (≥500 mg/dL) and are under investigation as adjuncts to statins for lowering cardiovascular risk in patients with high triglycerides (TGs; 200-499 mg/dL). To evaluate MAT9001, an investigational prescription-only omega-3 fatty acid agent containing predominantly eicosapentaenoic acid (EPA) and docosapentaenoic acid, in 42 men and women with fasting TG 200 to 400 mg/dL. In this open-label, crossover trial, subjects received MAT9001 and EPA ethyl esters (EPA-EE) in random order. They were housed in a clinical research unit for 2 14-day treatment periods, separated by a ≥35-day washout. Lipoprotein lipids, apolipoproteins (Apos) and proprotein convertase subtilisin kexin type 9 levels were measured before and at the end of each treatment period. MAT9001, compared with EPA-EE, resulted in significantly (P < .05) larger reductions from pretreatment levels for TG (-33.2% vs -10.5%), total cholesterol (-9.0% vs -6.2%), non-high-density lipoprotein cholesterol (-8.8% vs -4.6%), very low-density lipoprotein cholesterol (-32.5% vs -8.1%), Apo C3 (-25.5% vs -5.0%), and proprotein convertase subtilisin kexin type 9 (-12.3% vs +8.8%). MAT9001 also produced a significantly (P = .003) larger reduction in Apo A1 (-15.3% vs -10.2%), but responses for high-density lipoprotein cholesterol (-11.3% vs -11.1%), low-density lipoprotein cholesterol (-2.4% vs -4.3%), and Apo B (-3.8% vs -0.7%), respectively, were not significantly different relative to EPA-EE. MAT9001 produced significantly larger reductions than EPA-EE in several lipoprotein-related variables that would be expected to favorably alter cardiovascular disease risk in men and women with hypertriglyceridemia. Copyright © 2016 National Lipid Association. Published by Elsevier Inc. All rights reserved.

The use of fatty acid esters to enhance free acid sophorolipid synthesis.

PubMed

Ashby, Richard D; Solaiman, Daniel K Y; Foglia, Thomas A

2006-02-01

Fatty acid esters were prepared by transesterification of soy oil with methanol (methyl-soyate, Me-Soy), ethanol (ethyl-soyate, Et-Soy) and propanol (propyl-soyate, Pro-Soy) and used with glycerol as fermentation substrates to enhance production of free-acid sophorolipids (SLs). Fed-batch fermentations of Candida bombicola resulted in SL yields of 46 +/- 4 g/l, 42 +/- 7 g/l and 18 +/- 6 g/l from Me-Soy, Et-Soy, and Pro-Soy, respectively. Liquid chromatography with atmospheric pressure ionization mass spectrometry (LC/API-MS) showed that Me-Soy resulted in 71% open-chain SLs with 59% of those molecules remaining esterified at the carboxyl end of the fatty acids. Et-Soy and Pro-Soy resulted in 43% and 80% open-chain free-acid SLs, respectively (containing linoleic acid and oleic acid as the principal fatty acid species linked to the sophorose sugar at the omega-1 position), with no evidence of residual esterification.

Omega-3 fatty acids in baked freshwater fish from south of Brazil.

PubMed

Andrade, A D; Visentainer, J V; Matsushita, M; de Souza, N E

1997-03-01

Lipid and fatty acid levels in the edible flesh of 17 baked freshwater fish from Brazil's southern region were determined. Analyses of fatty acids methyl esters were performed by gas chromatography. Palmitic acid (C16:0) was the predominant saturated fatty acid, accouting for 50-70% of total saturated acids. Linoleic acid (C18:2 omega 6), linolenic acid (C18:3 omega 3), and docosahexaenoic acid (C22:6 omega 3) were the predominant polyunsatured fatty acids (PUFA). The data revealed that species such as barbado, corvina, pintado, and truta were good sources of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), and that most freshwater fish examined were good sources of PUFA-omega 3.

21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

Code of Federal Regulations, 2013 CFR

2013-04-01

... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

Code of Federal Regulations, 2012 CFR

2012-04-01

... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... Methyl and ethyl esters of fatty acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the...

Omega-3 fatty acid therapy reduces triglycerides and interleukin-6 in hypertriglyeridemic HIV patients.

PubMed

Metkus, T S; Timpone, J; Leaf, D; Bidwell Goetz, M; Harris, W S; Brown, T T

2013-10-01

Cardiovascular disease and osteoporosis are common in HIV-infected patients and residual systemic inflammation is thought to contribute to both of these disorders. We performed a randomized placebo-controlled trial of omega-3-acid (O3A) ethyl esters in HIV-infected patients with hypertriglyceridaemia, hypothesizing that O3A would decrease serum levels of triglycerides, markers of systemic inflammation, and markers of bone turnover. HIV-infected patients (n = 48 recruited at three sites) with CD4 count >200 cells/μL, suppressed viral load, and triglycerides >200 mg/dL were randomized to placebo or 3.6 g/d of O3A. Fasting lipid profiles and markers of inflammation and bone turnover were assessed at baseline and after 8 weeks of treatment. Baseline HIV status, lipid profile, bone metabolism and cardiovascular risk factors were similar between the groups. Inflammatory markers were similar between the treatment groups at baseline, except for interleukin (IL)-6 and tumour necrosis factor (TNF)-α, which were higher in the O3A group. The concentration of triglycerides in patients receiving O3A decreased by a median (interquartile range (IQR)) of -34 (-149, 9.5) mg/dL vs. a median increase of 46.5 (-51, 123) mg/dL in the placebo group (P = 0.01). The median percentage change in IL-6 was greater in the O3A group compared with the placebo group [-39% (-63, 12%) vs. 29% (10, 177%), respectively; P = 0.006]. Similar results were observed for TNF-α, but not other inflammatory or bone turnover markers. O3A ethyl esters decreased the concentrations of triglycerides, IL-6 and TNF-α in patients with well-controlled HIV infection and hypertriglyceridaemia. Larger studies are required to confirm these findings and investigate their clinical significance. © 2013 British HIV Association.

Ethyl ester formation is enhanced by ethanol addition in mini Swiss cheese with and without added propionibacteria.

PubMed

Thierry, Anne; Maillard, Marie-Bernadette; Richoux, Romain; Lortal, Sylvie

2006-09-06

Esters are important contributors to cheese flavor, but their mechanisms of synthesis in cheese are largely unknown. This study aimed to determine whether ethanol concentration limits the formation of ethyl esters in cheese. Mini Swiss cheeses were manufactured with (E) or without (C) the addition of ethanol to cheese milk. Ethanol concentrations (enzymatic analysis) were 64 +/- 17 and 330 +/- 82 microg g(-1), respectively, in C and E cheeses. E cheeses also contained 5.4 +/- 2.3 times more of the five ethyl esters quantified than C cheeses, regardless of the concentrations of esters in C cheeses (range 1-128 ng g(-1)). Furthermore, the presence of propionibacteria added as acid-producing secondary starters was associated with greater concentrations of esters, due to the increase in acid concentrations that propionibacteria induced and/or to an involvement of propionibacteria enzymes in ester synthesis. This study demonstrates that ethanol is the limiting factor of ethyl ester synthesis in Swiss cheese.

Synthesis of fruity ethyl esters by acyl coenzyme A: alcohol acyltransferase and reverse esterase activities in Oenococcus oeni and Lactobacillus plantarum.

PubMed

Costello, P J; Siebert, T E; Solomon, M R; Bartowsky, E J

2013-03-01

To assess the abilities of commercial wine lactic acid bacteria (LAB) to synthesize potentially flavour active fatty acid ethyl esters and determine mechanisms involved in their production. Oenococcus oeni AWRI B551 produced significant levels of ethyl hexanoate and ethyl octanoate following growth in an ethanolic test medium, and ester formation generally increased with increasing pH (4.5 > 3.5), anaerobiosis and precursor supplementation. Cell-free extracts of commercial O. oeni strains and Lactobacillus plantarum AWRI B740 were also tested for ester-synthesizing capabilities in a phosphate buffer via: (i) acyl coenzyme A: alcohol acyltransferase (AcoAAAT) activity and (ii) reverse esterase activity. For both ester-synthesizing activities, strain-dependent variation was observed, with AcoAAAT activity generally greater than reverse esterase. Reverse esterase in O. oeni AWRI B551 also esterified 1-propanol to produce propyl octanoate, and deuterated substrates ([(2)H(6)]ethanol and [(2)H(15)]octanoic acid) to produce the fully deuterated ester, [(2)H(5)]ethyl [(2)H(15)]octanoate. Wine LAB exhibit ethyl ester-synthesizing capability and possess two different ester-synthesizing activities, one of which is associated with an acyl coenzyme A: alcohol acyltransferase. This study demonstrates that wine LAB exhibit enzyme activities that can augment the ethyl ester content of wine. This knowledge will facilitate greater control over the impacts of malolactic fermentation on the fruity sensory properties and quality of wine. © 2012 Australian Wine Research Institute © 2012 The Society for Applied Microbiology.

Potential benefits of eicosapentaenoic acid on atherosclerotic plaques.

PubMed

Nelson, J R; Wani, O; May, H T; Budoff, M

2017-04-01

Residual cardiovascular (CV) risk remains in some patients despite optimized statin therapy and may necessitate add-on therapy to reduce this risk. Eicosapentaenoic acid (EPA), an omega-3 polyunsaturated fatty acid, lowers plasma triglyceride levels without raising low-density lipoprotein cholesterol levels and has potential beneficial effects on atherosclerotic plaques. Animal studies have shown that EPA reduces levels of pro-inflammatory cytokines and chemokines. In clinical trials utilizing a wide spectrum of plaque imaging modalities, EPA has shown beneficial effects on plaque characteristics. Studies of patients with coronary artery disease receiving statin therapy suggest that EPA may decrease plaque vulnerability and prevent plaque progression. EPA also decreased pentraxin-3 and macrophage accumulation. A large, randomized, Japanese study reported that EPA plus a statin resulted in a 19% relative reduction in major coronary events at 5years versus a statin alone in patients with hypercholesterolemia (P=0.011). Icosapent ethyl, a high-purity prescription form of EPA ethyl ester, has been shown to reduce triglyceride levels and markers of atherosclerotic inflammation. Results of an ongoing CV outcomes study will further define the potential clinical benefits of icosapent ethyl in reducing CV risk in high-risk patients receiving statin therapy. Copyright © 2017 The Authors. Published by Elsevier Inc. All rights reserved.

Minimal food effect for eicosapentaenoic acid and docosahexaenoic acid bioavailability from omega-3-acid ethyl esters with an Advanced Lipid TechnologiesTM (ALT®)-based formulation.

PubMed

Lopez-Toledano, Miguel A; Thorsteinsson, Thorsteinn; Daak, Ahmed A; Maki, Kevin C; Johns, Colleen; Rabinowicz, Adrian L; Sancilio, Frederick D

The absorption of eicosapentaenoic acid (EPA; 20:5n-3) and docosahexaenoic acid (DHA; 22:6n-3) omega-3-acid ethyl esters (EEs) is influenced by food. There is a need for a formulation of EE that is less impacted by food effect. SC401 is a novel Advanced Lipid Technologies-based formulation of EPA-EE and DHA-EE. In the presence of an aqueous medium, Advanced Lipid Technologies forms stable micelles in situ independent of bile salt secretion. This effect is hypothesized to improve EPA-EE and DHA-EE bioavailability while it helps mitigate the food effect associated with their consumption. The aim of the article was to assess the effect of food on the bioavailability of DHA and EPA after a single oral dose of 1530 mg omega-3 fatty acids EE (SC401) in 24 healthy subjects under fasted and low-fat (9% of total calories from fat) and high-fat (50% of total calories from fat) meal conditions. This was a randomized, open-label, single-dose, 3-period, 3-way crossover study. Blood samples for pharmacokinetic analyses were taken at predose and at 0.5, 1, 2, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 8, 10, 12 and 24 hours postdose. To assess the safety of the intervention, active monitoring of adverse events, physical examinations, vital signs, clinical laboratory assessments (chemistry, hematology, and urinalysis), and 12-lead electrocardiograms were conducted. SC401 showed high bioavailability of both EPA and DHA in fasted, low-fat meal, and high-fat meal conditions. No differences were found in SC401 DHA AUC 0-t (t = 24 hours) among the 3 conditions (91.69% high-fat/fasted, 97.12% low-fat/fasted, and 105.92% low-fat/high-fat; P > .05 in all cases). In contrast, SC401 EPA AUC 0-t was affected by food intake (179.06% high-fat/fasted, P < .0001; 150.05% low-fat/fasted, P < .0001) and the amount of fat taken with SC401 (83.80% low-fat/high-fat; P = .0009). SC401 was safe and well tolerated. A single dose of SC401 resulted in high levels of EPA and DHA total lipids in plasma in fasting and fed conditions. SC401 overcame the food effect for DHA and partially ameliorated it for EPA. SC401 represents a convenient option for treatment of severe hypertriglyceridemia, especially for patients under a restricted intake of dietary fat. Copyright © 2017 National Lipid Association. Published by Elsevier Inc. All rights reserved.

Review of Vaccinia Virus and Baculovirus Viability Versus Virucides

DTIC Science & Technology

2008-03-01

21 disinfectant. Sugimoto and Toyoshima (1979) reported on the inactivation of VACV by Na-Cocoyi-L-Arginine Ethyl Ester, DL- Pyroglutamic Acid Salt...12, pp 473-475. Sugimoto, Y.; Toyoshima, S. N"-Cocoyi-L-Arginine Ethyl Ester, DL- Pyroglutamic Acid Salt, as an Inactivator of Hepatitis B Surface...20 5.1.3 Ascorbic Acid ....................................................................... 20 5.1.4 Dithiothreitol Reducing Agent

DOE Office of Scientific and Technical Information (OSTI.GOV)

Uranga, Carla C., E-mail: curanga@cicese.edu.mx; Beld, Joris, E-mail: joris.beld@drexelmed.edu; Mrse, Anthony, E-mail: amrse@ucsd.edu

The Botryosphaeriaceae are a family of trunk disease fungi that cause dieback and death of various plant hosts. This work sought to characterize fatty acid derivatives in a highly virulent member of this family, Lasiodiplodia theobromae. Nuclear magnetic resonance and gas chromatography-mass spectrometry of an isolated compound revealed (Z, Z)-9,12-ethyl octadecadienoate, (trivial name ethyl linoleate), as one of the most abundant fatty acid esters produced by L. theobromae. A variety of naturally produced esters of fatty acids were identified in Botryosphaeriaceae. In comparison, the production of fatty acid esters in the soil-borne tomato pathogen Fusarium oxysporum, and the non-phytopathogenic fungusmore » Trichoderma asperellum was found to be limited. Ethyl linoleate, ethyl hexadecanoate (trivial name ethyl palmitate), and ethyl octadecanoate, (trivial name ethyl stearate), significantly inhibited tobacco seed germination and altered seedling leaf growth patterns and morphology at the highest concentration (0.2 mg/mL) tested, while ethyl linoleate and ethyl stearate significantly enhanced growth at low concentrations, with both still inducing growth at 98 ng/mL. This work provides new insights into the role of naturally esterified fatty acids from L. theobromae as plant growth regulators with similar activity to the well-known plant growth regulator gibberellic acid. - Highlights: • Lasiodiplodia theobromae produces a wide variety of fatty acid esters in natural substrates. • Ethyl stearate and ethyl linoleate inhibit tobacco germination at 0.2 mg/mL. • Ethyl stearate and ethyl linoleate induce tobacco germination at 98 ng/mL. • Tobacco growth increase in ethyl stearate and ethyl linoleate parallels gibberellic acid. • A role as plant growth regulators is proposed for fatty acid esters.« less

Effects of Food on the Pharmacokinetics of Omega-3-Carboxylic Acids in Healthy Japanese Male Subjects: A Phase I, Randomized, Open-label, Three-period, Crossover Trial.

PubMed

Shimada, Hitoshi; Nilsson, Catarina; Noda, Yoshinori; Kim, Hyosung; Lundström, Torbjörn; Yajima, Toshitaka

2017-09-01

Omega-3-carboxylic acids (OM3-CA) contain omega-3 free fatty acids, such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), as carboxylic acids. Food intake is known to affect the bioavailability of ethyl ester fatty acid formulations. We conducted a phase I study to investigate the effects of the timing of OM3-CA administration relative to food intake on the pharmacokinetics of EPA and DHA. In this randomized, open-label, three-period crossover study, Japanese healthy male subjects were administered 4×1 g OM3-CA capsules with continued fasting, before a meal, or after a meal. All subjects fasted for ≥10 h prior to drug/meal administration. The primary objective was to examine the effect of meal timing on the pharmacokinetics of EPA and DHA after OM3-CA administration. The secondary objectives were to examine the safety and tolerability of OM3-CA. A total of 42 Japanese subjects was enrolled in the study. The baseline-adjusted maximum concentration and area under the concentration-time curve from 0 to 72 h for EPA, DHA, and EPA +DHA were lower in the fasting and before meal conditions than in the after meal condition. The maximum total EPA, total DHA, and total EPA+DHA concentrations were reached later when administered in fasting conditions than in fed conditions, indicating slower absorption in fasting conditions. Diarrhea was reported by five, six, and no subjects in the fasting, before meal, and after meal conditions, respectively. The timing of OM3-CA administration relative to food intake influences the systemic bioavailability of EPA and DHA in healthy Japanese male subjects. NCT02372344.

4-Hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as potent anti-tumor agents.

PubMed

Hayakawa, Ichiro; Shioya, Rieko; Agatsuma, Toshinori; Furukawa, Hidehiko; Naruto, Shunji; Sugano, Yuichi

2004-01-19

Based on the structure of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester (1), which exhibits selective cytotoxicity against a tumorigenic cell line, (2,4-dimethoxyphenyl)-(4-hydroxy-3-methyl-6-phenylbenzofuran-2-yl)-methanone (18m) was designed and synthesized as a biologically stable derivative containing no ester group. Although the potency of 18m was almost the same as our initial hit compound 1, 18m is expected to last longer in the human body as an anticancer agent.

Long-term safety and efficacy of TAK-085 in Japanese subjects with hypertriglyceridemia undergoing lifestyle modification: the omega-3 fatty acids randomized long-term (ORL) study.

PubMed

Tatsuno, Ichiro; Saito, Yasushi; Kudou, Kentarou; Ootake, Jun

2013-01-01

TAK-085 is an omega-3 preparation that contains eicosapentaenoic acid ethyl-ester (EPA-E) and docosahexaenoic acid-ethyl ester used in the management of hypertriglyceridemia. The aim of the study was to evaluate the long-term safety (adverse events [AEs], laboratory parameters, vital signs, weight, and electrocardiograms) and effects on lipid profiles, especially triglyceride levels, of TAK-085 in Japanese patients with hypertriglyceridemia (triglyceride levels ≥150 mg/dL and <750 mg/dL). In this multicenter, open-label, randomized study, adults with hypertriglyceridemia undergoing lifestyle modification received TAK-085 2 g (2 g once daily; n = 165) or 4 g (2 g twice daily; n = 171), or EPA-E 1.8 g (0.6 g three times daily; n = 167) for 52 weeks. Patients were stratified for co-administration of a statin. TAK-085 was well tolerated throughout the 52-week study. Overall, no substantial differences were found in the tolerability of TAK-085 2 g, TAK-085 4 g, and EPA-E 1.8 g with incidence rates for AEs of 83.6%, 86.0%, and 89.2%, respectively. Most AEs were mild or moderate in severity. Triglyceride levels decreased from baseline in all groups by week 4, and the decreases were maintained throughout the study. At week 52 the reduction in triglycerides with TAK-085 2 g (-13.9%) was similar to that with EPA-E 1.8 g (-12.1%), whereas the reduction seen with TAK-085 4 g (-25.5%) was greater than that with EPA-E 1.8 g, as assessed by point estimates and 95% confidence intervals. TAK-085 was safe and well tolerated for up to 52 weeks of treatment in Japanese patients with hypertriglyceridemia undergoing lifestyle modification. Reductions in triglyceride levels achieved after 4 weeks were maintained at 52 weeks. Copyright © 2013 National Lipid Association. Published by Elsevier Inc. All rights reserved.

Metabolic engineering of Saccharomyces cerevisiae for production of fatty acid short- and branched-chain alkyl esters biodiesel.

PubMed

Teo, Wei Suong; Ling, Hua; Yu, Ai-Qun; Chang, Matthew Wook

2015-01-01

Biodiesel is a mixture of fatty acid short-chain alkyl esters of different fatty acid carbon chain lengths. However, while fatty acid methyl or ethyl esters are useful biodiesel produced commercially, fatty acid esters with branched-chain alcohol moieties have superior fuel properties. Crucially, this includes improved cold flow characteristics, as one of the major problems associated with biodiesel use is poor low-temperature flow properties. Hence, microbial production as a renewable, nontoxic and scalable method to produce fatty acid esters with branched-chain alcohol moieties from biomass is critical. We engineered Saccharomyces cerevisiae to produce fatty acid short- and branched-chain alkyl esters, including ethyl, isobutyl, isoamyl and active amyl esters using endogenously synthesized fatty acids and alcohols. Two wax ester synthase genes (ws2 and Maqu_0168 from Marinobacter sp.) were cloned and expressed. Both enzymes were found to catalyze the formation of fatty acid esters, with different alcohol preferences. To boost the ability of S. cerevisiae to produce the aforementioned esters, negative regulators of the INO1 gene in phospholipid metabolism, Rpd3 and Opi1, were deleted to increase flux towards fatty acyl-CoAs. In addition, five isobutanol pathway enzymes (Ilv2, Ilv5, Ilv3, Aro10, and Adh7) targeted into the mitochondria were overexpressed to enhance production of alcohol precursors. By combining these engineering strategies with high-cell-density fermentation, over 230 mg/L fatty acid short- and branched-chain alkyl esters were produced, which is the highest titer reported in yeast to date. In this work, we engineered the metabolism of S. cerevisiae to produce biodiesels in the form of fatty acid short- and branched-chain alkyl esters, including ethyl, isobutyl, isoamyl and active amyl esters. To our knowledge, this is the first report of the production of fatty acid isobutyl and active amyl esters in S. cerevisiae. Our findings will be useful for engineering S. cerevisiae strains toward high-level and sustainable biodiesel production.

Can pleiotropic effects of eicosapentaenoic acid (EPA) impact residual cardiovascular risk?

PubMed

Nelson, John R; True, Wayne S; Le, Viet; Mason, R Preston

2017-11-01

Residual cardiovascular (CV) risk persists even in statin-treated patients with optimized low-density lipoprotein cholesterol (LDL-C) levels. Other pathways beyond cholesterol contribute to CV risk and the key to reducing residual risk may be addressing non-cholesterol risk factors through pleiotropic mechanisms. The purpose of this review is to examine the literature relating to the potential role of the omega-3 fatty acid eicosapentaenoic acid (EPA) in reducing residual CV risk. The literature shows that EPA can robustly lower plasma triglyceride (TG) levels without raising LDL-C levels and documents EPA to have a broad range of beneficial effects on the atherosclerotic pathway, including those on lipids, lipoproteins, inflammation, oxidation, phospholipid membranes, and the atherosclerotic plaque itself. Clinical imaging studies have consistently demonstrated that EPA decreases plaque vulnerability and prevents plaque progression. The evidence therefore points to a potential role for EPA to reduce residual CV risk. A large randomized study of statin-treated Japanese patients demonstrated that EPA ethyl ester reduced major coronary events by 19% (P = 0.011). However, while there has been significant benefit demonstrated in this and another Japanese CV outcomes study, the question as to whether EPA can play a role in reducing residual CV risk remains to be addressed in broader populations. The large, global, ongoing, randomized, placebo-controlled REDUCE-IT study of high-risk statin-treated patients with persistent hypertriglyceridemia is currently underway to investigate the potential of icosapent ethyl (high-purity prescription EPA ethyl ester) as an add-on therapy to reduce residual CV risk.

40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Ni-tro-thio-phene-car-boxy-lic acid... Substances § 721.5375 Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino... reporting. (1) The chemical substance ni-tro-thio-phene-car-boxy-lic acid, ethyl ester, bis...

40 CFR 721.5375 - Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino]-alkyl-phenyl...

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Ni-tro-thio-phene-car-boxy-lic acid... Substances § 721.5375 Ni-tro-thio-phene-car-boxy-lic acid, ethyl es-ter, bis-[[[[(sub-sti-tut-ed)] amino... reporting. (1) The chemical substance ni-tro-thio-phene-car-boxy-lic acid, ethyl ester, bis...

A library synthesis of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester derivatives as anti-tumor agents.

PubMed

Hayakawa, Ichiro; Shioya, Rieko; Agatsuma, Toshinori; Furukawa, Hidehiko; Naruto, Shunji; Sugano, Yuichi

2004-09-06

As a result of a hit-to-lead program using a technique of solution-phase parallel synthesis, a highly potent (2,4-dimethoxyphenyl)-[6-(3-fluorophenyl)-4-hydroxy-3-methylbenzofuran-2-yl]methanone (15b) was synthesized as an optimized derivative of 4-hydroxy-3-methyl-6-phenylbenzofuran-2-carboxylic acid ethyl ester (1), which was discovered as a screening hit from small-molecule libraries and exhibited selective cytotoxicity against a tumorigenic cell line.

Potential grape-derived contributions to volatile ester concentrations in wine.

PubMed

Boss, Paul K; Pearce, Anthony D; Zhao, Yanjia; Nicholson, Emily L; Dennis, Eric G; Jeffery, David W

2015-04-29

Grape composition affects wine flavour and aroma not only through varietal compounds, but also by influencing the production of volatile compounds by yeast. C9 and C12 compounds that potentially influence ethyl ester synthesis during fermentation were studied using a model grape juice medium. It was shown that the addition of free fatty acids, their methyl esters or acyl-carnitine and acyl-amino acid conjugates can increase ethyl ester production in fermentations. The stimulation of ethyl ester production above that of the control was apparent when lower concentrations of the C9 compounds were added to the model musts compared to the C12 compounds. Four amino acids, which are involved in CoA biosynthesis, were also added to model grape juice medium in the absence of pantothenate to test their ability to influence ethyl and acetate ester production. β-Alanine was the only one shown to increase the production of ethyl esters, free fatty acids and acetate esters. The addition of 1 mg∙L(-1) β-alanine was enough to stimulate production of these compounds and addition of up to 100 mg∙L(-1) β-alanine had no greater effect. The endogenous concentrations of β-alanine in fifty Cabernet Sauvignon grape samples exceeded the 1 mg∙L(-1) required for the stimulatory effect on ethyl and acetate ester production observed in this study.

40 CFR 721.10457 - 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol...

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 1,2-Benzenedicarboxylic acid, mixed... Substances § 721.10457 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1... reporting. (1) The chemical substance identified as 1,2-benzenedicarboxylic acid, mixed esters with benzyl...

40 CFR 721.10457 - 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1-hexanol...

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 1,2-Benzenedicarboxylic acid, mixed... Substances § 721.10457 1,2-Benzenedicarboxylic acid, mixed esters with benzyl alc., cyclohexanol, 2-ethyl-1... reporting. (1) The chemical substance identified as 1,2-benzenedicarboxylic acid, mixed esters with benzyl...

Aroma Volatile Compounds from Two Fresh Pineapple Varieties in China

PubMed Central

Zheng, Liang-Yong; Sun, Guang-Ming; Liu, Yu-Ge; Lv, Ling-Ling; Yang, Wen-Xiu; Zhao, Wei-Feng; Wei, Chang-Bin

2012-01-01

Volatile compounds from two pineapples varieties (Tainong No.4 and No.6) were isolated by headspace solid phase microextraction (HS-SPME) and identified and quantified by gas chromatography-mass spectrometry (GC/MS). In the Tainong No. 4 and No. 6 pineapples, a total of 11 and 28 volatile compounds were identified according to their retention time on capillary columns and their mass spectra, and quantified with total concentrations of 1080.44 μg·kg−1 and 380.66 μg·kg−1 in the Tainong No.4 and No. 6 pineapples, respectively. The odor active values (OAVs) of volatile compounds from pineapples were also calculated. According to the OAVs, four compounds were defined as the characteristic aroma compounds for the Tainong No. 4 pineapple, including furaneol, 3-(methylthio)propanoic acid methyl ester, 3-(methylthio)propanoic acid ethyl ester and δ-octalactone. The OAVs of five compounds including ethyl-2-methylbutyrate, methyl-2-methylbutyrate, 3-(methylthio)propanoic acid ethyl ester, ethyl hexanoate and decanal were considered to be the characteristic aroma compounds for the Tainong No. 6 pineapple. PMID:22837701

Characterization of the Key Aroma Compounds in Chinese Syrah Wine by Gas Chromatography-Olfactometry-Mass Spectrometry and Aroma Reconstitution Studies.

PubMed

Zhao, Pengtao; Gao, Jinxin; Qian, Michael; Li, Hua

2017-06-24

The key aroma compounds and the organoleptic quality of two Chinese Syrah wines from the Yunnan Shangri-La region and Ningxia Helan mountain region were characterized. The most important eighty aroma-active compounds were identified by Gas Chromatography-Olfactometry. In both Syrah samples, ethyl 2-methylpropanoate, ethyl 3-methylbutanoate, 3-methylbutyl acetate, 2- and 3-methyl-1-butanol, ethyl hexanoate, ethyl octanoate, 2-phenethyl acetate, methional, 3-methylbutanoic acid, hexanoic acid, octanoic acid, β -damascenone, guaiacol, 2-phenylethanol, trans -whiskylactone, 4-ethylguaiacol, eugenol, 4-ethylphenol, and sotolon were detected to have the highest odor intensities. In the chemical analysis, 72 compounds were quantitated by Stir Bar Sorptive Extraction combined with Gas Chromatography Mass Spectrometry. Based on the Odor Activity Value (OAV), the aromas were reconstituted by combining aroma compounds in the synthetic wine, and sensory descriptive analysis was used to verify the chemical data. Fatty acid ethyl esters, acetate esters, and β -damascenone were found with higher OAVs in the more fruity-smelling sample of Helan Mountain rather than Shangri-La.

A Simple, Safe Method for Preparation of Biodiesel

ERIC Educational Resources Information Center

Behnia, Mahin S.; Emerson, David W.; Steinberg, Spencer M.; Alwis, Rasika M.; Duenas, Josue A.; Serafino, Jessica O.

2011-01-01

An experiment suitable for organic chemistry students is described. Biodiesel, a "green" fuel, consists of methyl or ethyl esters of long-chain fatty acids called FAMES (fatty acid methyl esters) or FAEES (fatty acid ethyl esters). A quick way to make FAMES is a base-catalyzed transesterification of oils or fats derived from plants or from animal…

Symbiotic zooxanthellae provide the host-coral Montipora digitata with polyunsaturated fatty acids.

PubMed

Papina, M; Meziane, T; van Woesik, R

2003-07-01

We compared the fatty acid composition of the host-coral Montipora digitata with the fatty acid composition in the coral's endosymbiotic dinoflagellates (zooxanthellae). Fatty acids as methyl esters were determined using gas chromatography (GC) and verified by GC-mass spectrometry. We found the main difference between the fatty acids in the host and their symbionts were that zooxanthellae supported higher proportions of polyunsaturated fatty acids. The presence of fatty acids specific to dinoflagellates (i.e. 18:4omega3, 22:5omega3 and 22:6omega3) in the host tissue suggests that zooxanthellae provide the coral host not only with saturated fatty acids, but also with diverse polyunsaturated fatty acids.

40 CFR 721.6120 - Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. 721.6120 Section 721.6120 Protection of Environment...-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. (a) Chemical substances and significant new uses...

40 CFR 721.6120 - Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. 721.6120 Section 721.6120 Protection of Environment...-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. (a) Chemical substances and significant new uses...

40 CFR 721.6120 - Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester.

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. 721.6120 Section 721.6120 Protection of Environment...-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. (a) Chemical substances and significant new uses...

40 CFR 721.6120 - Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester.

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. 721.6120 Section 721.6120 Protection of Environment...-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. (a) Chemical substances and significant new uses...

40 CFR 721.6120 - Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester.

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phosphoric acid, 1,2-eth-a-ne-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. 721.6120 Section 721.6120 Protection of Environment...-diyl tet-ra-kis(2-chloro-1-meth-yl-ethyl) ester. (a) Chemical substances and significant new uses...

Carbodithioic acid esters of fluoxetine, a novel class of dual-function spermicides.

PubMed

Kiran Kumar, S T V S; Kumar, Lalit; Sharma, Vishnu L; Jain, Ashish; Jain, Rajeev K; Maikhuri, Jagdamba P; Kumar, Manish; Shukla, Praveen K; Gupta, Gopal

2008-10-01

Carbodithioic acid esters of fluoxetine have been prepared by replacing the methylamino function in aminopropane chain with carbodithioic acid ester group and by adding various S-2-hydroxypropyl ester of dialkyl carbodithioic acid at 3-methylamino group. Some of these compounds showed spermicidal, antifungal and anti-Trichomonas activities. The study revealed that incorporation of carbodithioic acid residue directly into fluoxetine structure leads to compounds with better antifungal and anti-Trichomonas activities, and N-methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]carbodithioic acid S-(2-pyrrolidino-ethyl) ester (14) has shown better profile than both fluoxetine and nonoxynol-9. Further lead optimization may yield a potent dual-function spermicide.

21 CFR 172.225 - Methyl and ethyl esters of fatty acids produced from edible fats and oils.

Code of Federal Regulations, 2014 CFR

2014-04-01

... from edible fats and oils. 172.225 Section 172.225 Food and Drugs FOOD AND DRUG ADMINISTRATION... acids produced from edible fats and oils. Methyl esters and ethyl esters of fatty acids produced from edible fats and oils may be safely used in food, subject to the following prescribed conditions: (a) The...

Preparation and characterization of bio-diesels from various bio-oils.

PubMed

Lang, X; Dalai, A K; Bakhshi, N N; Reaney, M J; Hertz, P B

2001-10-01

Methyl, ethyl, 2-propyl and butyl esters were prepared from canola and linseed oils through transesterification using KOH and/ or sodium alkoxides as catalysts. In addition, methyl and ethyl esters were prepared from rapeseed and sunflower oils using the same catalysts. Chemical composition of the esters was determined by HPLC for the class of lipids and by GC for fatty acid compositions. The bio-diesel esters were characterized for their physical and fuel properties including density, viscosity, iodine value, acid value, cloud point, pure point, gross heat of combustion and volatility. Methyl and ethyl esters prepared from a particular vegetable oil had similar viscosities, cloud points and pour points, whereas methyl, ethyl, 2-propyl and butyl esters derived from a particular vegetable oil had similar gross heating values. However, their densities, which were 2 7% higher than those of diesel fuels, statistically decreased in the order of methyl approximately 2-propyl > ethyl > butyl esters. Butyl esters showed reduced cloud points (-6 degrees C to -10 degrees C) and pour points (-13 degrees C to -16 degrees C) similar to those of summer diesel fuel having cloud and pour points of -8 degrees C and -15 degrees C, respectively. The viscosities of bio-diesels (3.3-7.6 x 10(-4) Pa s at 40 degrees C) were much less than those of pure oils (22.4-45.1 x 10(-4) Pa s at 40 degrees C) and were twice those of summer and winter diesel fuels (3.50 and 1.72 x 10(-4) Pa s at 40 degrees C), and their gross heat contents of approximately 40 MJ/kg were 11% less than those of diesel fuels (approximately 45 MJ/kg). For different esters from the same vegetable oil, methyl esters were the most volatile, and the volatility decreased as the alkyl group grew bulkier. However, the bio-diesels were considerably less volatile than the conventional diesel fuels.

Electrode Potentials of l-Tryptophan, l-Tyrosine, 3-Nitro-l-tyrosine, 2,3-Difluoro-l-tyrosine, and 2,3,5-Trifluoro-l-tyrosine.

PubMed

Mahmoudi, Leila; Kissner, Reinhard; Nauser, Thomas; Koppenol, Willem H

2016-05-24

Electrode potentials for aromatic amino acid radical/amino acid couples were deduced from cyclic voltammograms and pulse radiolysis experiments. The amino acids investigated were l-tryptophan, l-tyrosine, N-acetyl-l-tyrosine methyl ester, N-acetyl-3-nitro-l-tyrosine ethyl ester, N-acetyl-2,3-difluoro-l-tyrosine methyl ester, and N-acetyl-2,3,5-trifluoro-l-tyrosine methyl ester. Conditional potentials were determined at pH 7.4 for all compounds listed; furthermore, Pourbaix diagrams for l-tryptophan, l-tyrosine, and N-acetyl-3-nitro-l-tyrosine ethyl ester were obtained. Electron transfer accompanied by proton transfer is reversible, as confirmed by detailed analysis of the current waves, and because the slopes of the Pourbaix diagrams obey Nernst's law. E°'(Trp(•),H(+)/TrpH) and E°'(TyrO(•),H(+)/TyrOH) at pH 7 are 0.99 ± 0.01 and 0.97 ± 0.01 V, respectively. Pulse radiolysis studies of two dipeptides that contain both amino acids indicate a difference in E°' of approximately 0.06 V. Thus, in small peptides, we recommend values of 1.00 and 0.96 V for E°'(Trp(•),H(+)/TrpH) and E°'(TyrO(•),H(+)/TyrOH), respectively. The electrode potential of N-acetyl-3-nitro-l-tyrosine ethyl ester is higher, while because of mesomeric stabilization of the radical, those of N-acetyl-2,3-difluoro-l-tyrosine methyl ester and N-acetyl-2,3,5-trifluoro-l-tyrosine methyl ester are lower than that of tyrosine. Given that the electrode potentials at pH 7 of E°'(Trp(•),H(+)/TrpH) and E°'(TyrO(•),H(+)/TyrOH) are nearly equal, they would be, in principle, interchangeable. Proton-coupled electron transfer pathways in proteins that use TrpH and TyrOH are thus nearly thermoneutral.

Increase of medium-chain fatty acid ethyl ester content in mixed H. uvarum/S. cerevisiae fermentation leads to wine fruity aroma enhancement.

PubMed

Hu, Kai; Jin, Guo-Jie; Mei, Wen-Chao; Li, Ting; Tao, Yong-Sheng

2018-01-15

Medium-chain fatty acid (MCFA) ethyl esters, as yeast secondary metabolites, significantly contribute to the fruity aroma of foods and beverages. To improve the MCFA ethyl ester content of wine, mixed fermentations with Hanseniaspora uvarum Yun268 and Saccharomyces cerevisiae were performed. Final volatiles were analyzed by gas solid phase microextraction-chromatography-mass spectrometry, and aroma characteristics were quantitated by sensory analysis. Results showed that mixed fermentation increased MCFA ethyl ester content by 37% in Cabernet Gernischt wine compared to that obtained by pure fermentation. Partial least-squares regression analysis further revealed that the improved MCFA ethyl esters specifically enhanced the temperate fruity aroma of wine. The enhancement of MCFA ethyl esters was attributed to the increased contents of MCFAs that could be induced by the presence of H. uvarum Yun268 in mixed fermentation. Meanwhile, the timing of yeast inoculations significantly affected the involving biomass of each strain and the dynamics of ethanol accumulation. Copyright © 2017 Elsevier Ltd. All rights reserved.

40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid, .alpha.-chloro-.alpha...

40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid, .alpha.-chloro-.alpha...

40 CFR 721.10300 - Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester.

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Benzeneacetic acid, .alpha.-chloro-.alpha.-phenyl-, ethyl ester. 721.10300 Section 721.10300 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10300 Benzeneacetic acid, .alpha.-chloro-.alpha...

Comparative study on fermentation performance in the genome shuffled Candida versatilis and wild-type salt tolerant yeast strain.

PubMed

Qi, Wei; Guo, Hong-Lian; Wang, Chun-Ling; Hou, Li-Hua; Cao, Xiao-Hong; Liu, Jin-Fu; Lu, Fu-Ping

2017-01-01

The fermentation performance of a genome-shuffled strain of Candida versatilis S3-5, isolated for improved tolerance to salt, and wild-type (WT) strain were analysed. The fermentation parameters, such as growth, reducing sugar, ethanol, organic acids and volatile compounds, were detected during soy sauce fermentation process. The results showed that ethanol produced by the genome shuffled strain S3-5 was increasing at a faster rate and to a greater extent than WT. At the end of the fermentation, malic acid, citric acid and succinic acid formed in tricarboxylic acid cycle after S3-5 treatment elevated by 39.20%, 6.85% and 17.09% compared to WT, respectively. Moreover, flavour compounds such as phenethyl acetate, ethyl vanillate, ethyl acetate, isoamyl acetate, ethyl myristate, ethyl pentadecanoate, ethyl palmitate and phenylacetaldehyde produced by S3-5 were 2.26, 2.12, 2.87, 34.41, 6.32, 13.64, 2.23 and 78.85 times as compared to WT. S3-5 exhibited enhanced metabolic ability as compared to the wild-type strain, improved conversion of sugars to ethanol, metabolism of organic acid and formation of volatile compounds, especially esters, Moreover, S3-5 might be an ester-flavour type salt-tolerant yeast. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

Peripheral substitution of pheophorbides and bacteriopheophorbides to promote inclusion into inert carrier systems for PDT

NASA Astrophysics Data System (ADS)

Roehrs, Susanne; Ruebner-Heuermann, Anja; Hartwich, G.; Scheer, H.; Moser, Joerg G.

1996-01-01

Pheophorbide a ethyl ester, pyropheophorbide a ethyl ester, and bacteriopheophorbide ethyl ester were substituted in 31-position with tert.butyl phenoxy or tert.butyl benzoic acid ester groups resp. in order to enhance affinity to (beta) -cyclodextrin dimers which form inclusion complexes with these photosensitizing drugs. This is a first step to construct inert transport complexes in order to photosensitize specifically cancer cells.

Proton-Ionizable Crown Ethers. A Short Review

DTIC Science & Technology

1989-05-30

acid methyl ester using sodium hydride as the base in tetrahydrofuran. The m3thyl ester group was hydrolyzed to the carboxylic acid as shown in Procedure...prepared via the appropriate hydroxydibenzo-crown ether and allyl bromide RýIý R2 or ethyl acrylate as shown in Procedure N. 5 2 . 5 6 Disulfonic acid ...similar to Procedure p. 7 4 Once the precursor binrephtho-crown was obtained, it was coupled with bromoacetic acid methyl ester and R, , - R

Method for high specific bioproductivity of .alpha.,.omega.-alkanedicarboxylic acids

DOEpatents

Mobley, David Paul; Shank, Gary Keith

2000-01-01

This invention provides a low-cost method of producing .alpha.,.omega.-alkanedicarboxylic acids. Particular bioconversion conditions result in highly efficient conversion of fatty acid, fatty acid ester, or alkane substrates to diacids. Candida tropicalis AR40 or similar yeast strains are grown in a medium containing a carbon source and a nitrogen source at a temperature of 31.degree. C. to 38.degree. C., while additional carbon source is continuously added, until maximum cell growth is attained. Within 0-3 hours of this point, substrate is added to the culture to initiate conversion. An .alpha.,.omega.-alkanedicarboxylic acid made according to this method is also provided.

Biocatalytic ammonolysis of (5S)-4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl)-5-ethyl ester: preparation of an intermediate to the dipeptidyl peptidase IV inhibitor Saxagliptin.

PubMed

Gill, Iqbal; Patel, Ramesh

2006-02-01

An efficient biocatalytic method has been developed for the conversion of (5S)-4,5-dihydro-1H-pyrrole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl)-5-ethyl ester (1) into the corresponding amide (5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid, 1-(1,1-dimethylethyl)ester (2), which is a critical intermediate in the synthesis of the dipeptidyl peptidase IV (DPP4) inhibitor Saxagliptin (3). Candida antartica lipase B mediates ammonolysis of the ester with ammonium carbamate as ammonia donor to yield up to 71% of the amide. The inclusion of Ascarite and calcium chloride as adsorbents for carbon dioxide and ethanol byproducts, respectively, increases the yield to 98%, thereby offering an efficient and practical alternative to chemical routes which yield 57-64%.

Optimization of esterification of dicarboxylic acids and 2-ethyl-1-hexanol

NASA Astrophysics Data System (ADS)

Jafri, Nur Hafifah Nahdirah; Othman, Nor Hamidah Abu; Salimon, Jumat

2018-04-01

Dicarboxylate ester has the potential alternative as plasticizer which environmentally friendly in polymeric formulation especially for poly (vinyl chloride) (PVC). Dicarboxylate ester compounds were synthesized via esterification between dicarboxylic acid and 2-ethyl-1-hexanol by using sulfuric acid as catalyst. The effects of reaction parameters were studied by optimizing temperature, mole ratio of reactants, amount of catalyst and reaction to obtain highest ester conversion. The optimum results showed dicarboxylic acid successfully converted to the dicarboxylate ester at parameters; 4 hours; 120 °C; catalyst amount: 2% w/w of diacid; and mole ratio: 1:2.5. Functional group analysis was conducted by using ATR-FTIR spectroscopy.

A new pure ω-3 eicosapentaenoic acid ethyl ester (AMR101) for the management of hypertriglyceridemia: the MARINE trial.

PubMed

Jacobson, Terry A

2012-06-01

ω-3 fatty acids reduce triglyceride (TG) levels, but corresponding increases in low-density lipoprotein cholesterol (LDL-C) levels may compromise achievement of lipid goals in patients with elevated cardiovascular risk. AMR101 is an investigational agent containing ≥96% of pure icosapent ethyl (the ethyl ester of eicosapentaenoic acid). The Phase III Multi-Center, Placebo-Controlled, Randomized, Double-Blind, 12-Week Study with an Open-Label Extension (MARINE) investigated the efficacy and safety of AMR101 in 229 patients with very high TG levels (≥500 mg/dl). AMR101 4 g/day significantly reduced median placebo-adjusted TG levels from baseline by 33.1% (p < 0.0001), and AMR101 2 g/day reduced TG levels by 19.7% (p = 0.0051). Changes in LDL-C were minimal and nonsignificant. AMR101 may offer substantial TG lowering without increases in LDL-C levels.

[Chemical constituents from whole plants of Aconitum tanguticum (III)].

PubMed

Li, Yan-Rong; Li, Chun; Wang, Zhi-Min; Yang, Li-Xin

2014-04-01

Nineteen compounds were isolated from the whole plants of Aconitum tanguticum by various of chromatographic techniques and their structures were determined through spectral analysis (1D, 2D-NMR and MS) and comparison with the literature data. These compounds were identified as 5-hydroxymethy furfural (1), 5-acetoxymethyl furfural (2), pyrrolezanthine [5-hydroxymethyl-1-[2-(4-hydroxyphenyl) -ethyl] -1H-pyrrole-2-carbaldehyde] (3), lichiol B (4), phthalic acid dibutyl ester (5), 3, 4-dihydroxy phenylethanol (6), 3, 4-dihydroxy phenylethanol glucoside (7), salidroside (8), p-hydroxy phenylethanol (9), p-hydroxybenzoie acid glucoside (10), p-hydroxybenzoic acid (11), gastrodin (12), 1-(3, 4-dimethoxyphenyl) -1, 2-ethanediol (13), p-hydroxy benzaldehyde (14), p-hydroxy acetophenone (15), 3, 4-dihydroxy phenyl ethyl acetate (16), syringic aldehyde (17), ethyl beta-D-fructopyranoside (18), and p-hydroxybenzoic acid methyl ester (19). Compounds 3 and 4 were isolated from the Ranunculaceae family for the first time, and compounds 2, 6 and 9-19 were isolated from the Aconitum genus for the first time, and compounds 1 and 5 were isolated from the species for the first time.

Triterpene Esters and Biological Activities from Edible Fruits of Manilkara subsericea (Mart.) Dubard, Sapotaceae

PubMed Central

Fernandes, Caio P.; Corrêa, Arthur L.; Lobo, Jonathas F. R.; Caramel, Otávio P.; de Almeida, Fernanda B.; Castro, Elaine S.; Souza, Kauê F. C. S.; Burth, Patrícia; Amorim, Lidia M. F.; Santos, Marcelo G.; Ferreira, José Luiz P.; Falcão, Deborah Q.; Carvalho, José C. T.; Rocha, Leandro

2013-01-01

Manilkara subsericea (Mart.) Dubard (Sapotaceae) is popularly known in Brazil as “guracica.” Studies with Manilkara spp indicated the presence of triterpenes, saponins, and flavonoids. Several activities have been attributed to Manilkara spp such as antimicrobial, antiparasitic and antitumoral, which indicates the great biological potential of this genus. In all, 87.19% of the hexanic extract from fruits relative composition were evaluated, in which 72.81% were beta- and alpha-amyrin esters, suggesting that they may be chemical markers for M. subsericea. Hexadecanoic acid, hexadecanoic acid ethyl ester, (E)-9-octadecenoic acid ethyl ester, and octadecanoic acid ethyl ester were also identified. Ethanolic crude extracts from leaves, stems, and hexanic extract from fruits exhibited antimicrobial activity against Staphylococcus aureus ATCC25923. These extracts had high IC50 values against Vero cells, demonstrating weak cytotoxicity. This is the first time, to our knowledge, that beta- and alpha-amyrin caproates and caprylates are described for Manilkara subsericea. PMID:23509702

Amidation reaction of eugenyl oxyacetate ethyl ester with 1,3 diaminopropane

NASA Astrophysics Data System (ADS)

Suryanti, V.; Wibowo, F. R.; Kusumaningsih, T.; Wibowo, A. H.; Khumaidah, S. A.; Wijayanti, L. A.

2016-04-01

Eugenol having various substituents on the aromatic ring (hydroxy, methoxy and allyl) are useful for starting material in synthesizing of its derivatives. Eugenol derivatives have shown wide future potential applications in many areas, especially as future drugs against many diseases. The aim of this work was to synthesize an amide of eugenol derivative. The starting material used was eugenol from clove oil and the reaction was conducted in 3 step reactions to give the final product. Firstly, eugenol was converted into eugenyl oxyacetate [2-(4-allyl-2-methoxyphenoxy) acetic acid] as a white crystal with 70.5% yield, which was then esterified with ethanol to have eugenyl oxyacetate ethyl ester [ethyl 2-(4-allyl-2-methoxyphenoxy) acetate] as brown liquid in 75.7%. The last step was the reaction between eugenyl oxyacetate ethyl ester and 1,3 diaminopropane to give 2-(4-allyl-2-methoxyphenoxy)-N-(3-aminopropyl) acetamide as a brown powder with 71.6% yield, where the amidation reaction was occurred.

In Vitro and Ex Vivo Evaluation of Novel Curcumin-Loaded Excipient for Buccal Delivery.

PubMed

Laffleur, Flavia; Schmelzle, Franziska; Ganner, Ariane; Vanicek, Stefan

2017-08-01

This study aimed to develop a mucoadhesive polymeric excipient comprising curcumin for buccal delivery. Curcumin encompasses broad range of benefits such as antioxidant, anti-inflammatory, and chemotherapeutic activity. Hyaluronic acid (HA) as polymeric excipient was modified by immobilization of thiol bearing ligands. L-Cysteine (SH) ethyl ester was covalently attached via amide bond formation between cysteine and the carboxylic moiety of hyaluronic acid. Succeeded synthesis was proved by H-NMR and IR spectra. The obtained thiolated polymer hyaluronic acid ethyl ester (HA-SH) was evaluated in terms of stability, safety, mucoadhesiveness, drug release, and permeation-enhancing properties. HA-SH showed 2.75-fold higher swelling capacity over time in comparison to unmodified polymer. Furthermore, mucoadhesion increased 3.4-fold in case of HA-SH and drug release was increased 1.6-fold versus HA control, respectively. Curcumin-loaded HA-SH exhibits a 4.4-fold higher permeation compared with respective HA. Taking these outcomes in consideration, novel curcumin-loaded excipient, namely thiolated hyaluronic acid ethyl ester appears as promising tool for pharyngeal diseases.

n-3 PUFA esterified to glycerol or as ethyl esters reduce non-fasting plasma triacylglycerol in subjects with hypertriglyceridemia: a randomized trial.

PubMed

Hedengran, Anne; Szecsi, Pal B; Dyerberg, Jørn; Harris, William S; Stender, Steen

2015-02-01

To date, treatment of hypertriglyceridemia with long-chain n-3 polyunsaturated fatty acids (n-3 PUFA) has been investigated solely in fasting and postprandial subjects. However, non-fasting triacylglycerols are more strongly associated with risk of cardiovascular disease. The objective of this study was to investigate the effect of long-chain n-3 PUFA on non-fasting triacylglycerol levels and to compare the effects of n-3 PUFA formulated as acylglycerol (AG-PUFA) or ethyl esters (EE-PUFA). The study was a double-blinded randomized placebo-controlled interventional trial, and included 120 subjects with non-fasting plasma triacylglycerol levels of 1.7-5.65 mmol/L (150-500 mg/dL). The participants received approximately 3 g/day of AG-PUFA, EE-PUFA, or placebo for a period of eight weeks. The levels of non-fasting plasma triacylglycerols decreased 28% in the AG-PUFA group and 22% in the EE-PUFA group (P < 0.001 vs. placebo), with no significant difference between the two groups. The triacylglycerol lowering effect was evident after four weeks, and was inversely correlated with the omega-3 index (EPA + DHA content in erythrocyte membranes). The omega-3 index increased 63.2% in the AG-PUFA group and 58.5% in the EE-PUFA group (P < 0.001). Overall, the heart rate in the AG-PUFA group decreased by three beats per minute (P = 0.045). High-density lipoprotein (HDL) cholesterol increased in the AG-PUFA group (P < 0.001). Neither total nor non-HDL cholesterol changed in any group. Lipoprotein-associated phospholipase A2 (LpPLA2) decreased in the EE-PUFA group (P = 0.001). No serious adverse events were observed. Supplementation with long-chain n-3 PUFA lowered non-fasting triacylglycerol levels, suggestive of a reduction in cardiovascular risk. Regardless of the different effects on heart rate, HDL, and LpPLA2 that were observed, compared to placebo, AG-PUFA, and EE-PUFA are equally effective in reducing non-fasting triacylglycerol levels.

Production of 10(S)-hydroxy-8(E)-octadecenoic and 7,10(S,S)-hydroxy-8(E)-octadecenoic ethyl esters by Novozym 435 in solvent-free media

USDA-ARS?s Scientific Manuscript database

Novozym 435, lipase B from Candida antarctica, was used in this study for the production of ethyl esters. For the first time, trans-hydroxy-fatty acid ethyl esters were synthesized in vitro in solvent-free media. We studied the effects of the substrate–ethanol molar ratio and enzyme synthetic stabil...

Liner Technology Program. Volume 3. Liner Development Methodology Manual

DTIC Science & Technology

1982-05-01

derivative of trimesic acid, trimenoyl-l- (2-ethyl) aziridine BNO Hydroxyl ethyl ester of carboxy-terminated polybutadiene Catocene Liquid ferrocene ...diisocyanate MAPO rris-l-(2-methyl) aziridinyl phosphine oxide I.’ lNA Methyl nedic anhydride; methyl endo-cis-cicyolo-2,2,1-5- heptene-2,3-dicarboxylic

Convenient synthesis of 6-nor-9,10-dihydrolysergic acid methyl ester.

PubMed

Crider, A M; Grubb, R; Bachmann, K A; Rawat, A K

1981-12-01

6-Nor-9,10-dihydrolysergic acid methyl ester (IV) was prepared by demethylation of 9,10-dihydrolysergic acid methyl ester (II) with 2,2,2-trichloroethyl chloroformate, followed by reduction of the intermediate carbamate (III) with zinc in acetic acid. The 6-ethyl-V and 6-n-propyl-VI derivatives were prepared by alkylation of IV with the appropriate halide. All of the ergoline derivatives were evaluated for stereotyped behavior in rats, with 6-nor-6-ethyl-9,10-dihydrolysergic acid methyl ester (V) being active but much less potent than apomorphine. Compound VI was evaluated for its effect on blood pressure; at a dose of 30 mg/kg ip, it significantly lowered, diastolic pressure in normotensive rats.

Analysis of aroma compounds of pitaya fruit wine

NASA Astrophysics Data System (ADS)

Gong, Xiao; Ma, Lina; Li, Liuji; Yuan, Yuan; Peng, Shaodan; Lin, Mao

2017-12-01

In order to analyze the volatile components in red pitaya fruit wine, the study using headspace solid phase microextractionand gas chromatography-mass spectrometry technology of pitaya fruit juice and wine aroma composition analysis comparison. Results showed that 55 volatile components were detected in red pitaya fruit wine, including 12 kinds of alcohol (18.16%), 18 kinds of esters (66.17%), 7 kinds of acids (5.94%), 11 kinds of alkanes (4.32%), one kind of aldehyde (0.09%), 2 kinds of olefins (0.09%) and 3 kinds of other volatile substances (0.23%). Relative contents among them bigger have 11 species, such as decanoic acid, ethyl ester (22.92%), respectively, diisoamylene (20.75%), octanoic acid, ethyl ester (17.73%), etc. The red pitaya fruit wine contained a lot of aroma components, which offer the products special aroma like brandy, rose and fruit.

Application of AlkBGT and AlkL from Pseudomonas putida GPo1 for Selective Alkyl Ester ω-Oxyfunctionalization in Escherichia coli

PubMed Central

Eggink, Gerrit; Weusthuis, Ruud A.

2016-01-01

ABSTRACT The enzyme system AlkBGT from Pseudomonas putida GPo1 can efficiently ω-functionalize fatty acid methyl esters. Outer membrane protein AlkL boosts this ω-functionalization. In this report, it is shown that whole cells of Escherichia coli expressing the AlkBGT system can also ω-oxidize ethyl nonanoate (NAEE). Coexpression of AlkBGT and AlkL resulted in 1.7-fold-higher ω-oxidation activity on NAEE. With this strain, initial activity on NAEE was 70 U/g (dry weight) of cells (gcdw), 67% of the initial activity on methyl nonanoate. In time-lapse conversions with 5 mM NAEE the main product was 9-hydroxy NAEE (3.6 mM), but also 9-oxo NAEE (0.1 mM) and 9-carboxy NAEE (0.6 mM) were formed. AlkBGT also ω-oxidized ethyl, propyl, and butyl esters of fatty acids ranging from C6 to C10. Increasing the length of the alkyl chain improved the ω-oxidation activity of AlkBGT on esters of C6 and C7 fatty acids. From these esters, application of butyl hexanoate resulted in the highest ω-oxidation activity, 82 U/gcdw. Coexpression of AlkL only had a positive effect on ω-functionalization of substrates with a total length of C11 or longer. These findings indicate that AlkBGT(L) can be applied as a biocatalyst for ω-functionalization of ethyl, propyl, and butyl esters of medium-chain fatty acids. IMPORTANCE Fatty acid esters are promising renewable starting materials for the production of ω-hydroxy fatty acid esters (ω-HFAEs). ω-HFAEs can be used to produce sustainable polymers. Chemical conversion of the fatty acid esters to ω-HFAEs is challenging, as it generates by-products and needs harsh reaction conditions. Biocatalytic production is a promising alternative. In this study, biocatalytic conversion of fatty acid esters toward ω-HFAEs was investigated using whole cells. This was achieved with recombinant Escherichia coli cells that produce the AlkBGT enzymes. These enzymes can produce ω-HFAEs from a wide variety of fatty acid esters. Medium-chain-length acids (C6 to C10) esterified with ethanol, propanol, or butanol were applied. This is a promising production platform for polymer building blocks that uses renewable substrates and mild reaction conditions. PMID:27084021

Influence of Grape Composition on Red Wine Ester Profile: Comparison between Cabernet Sauvignon and Shiraz Cultivars from Australian Warm Climate.

PubMed

Antalick, Guillaume; Šuklje, Katja; Blackman, John W; Meeks, Campbell; Deloire, Alain; Schmidtke, Leigh M

2015-05-13

The relationship between grape composition and subsequent red wine ester profile was examined. Cabernet Sauvignon and Shiraz, from the same Australian very warm climate vineyard, were harvested at two different stages of maturity and triplicate wines were vinified. Grape analyses focused on nitrogen and lipid composition by measuring 18 amino acids by HPLC-FLD, 3 polyunsaturated fatty acids, and 6 C6-compounds derived from lipid degradation by GC-MS. Twenty esters and four higher alcohols were analyzed in wines by HS-SPME-GC-MS. Concentrations of the ethyl esters of branched acids were significantly affected by grape maturity, but the variations were inconsistent between cultivars. Small relative variations were observed between wines for ethyl esters of fatty acids, whereas higher alcohol acetates displayed the most obvious differences with concentrations ranging from 1.5- to 26-fold higher in Shiraz than in Cabernet Sauvignon wines regardless of the grape maturity. Grape analyses revealed the variations of wine ester composition might be related to specific grape juice nitrogen composition and lipid metabolism. To the authors' knowledge the present study is the first to investigate varietal differences in the ester profiles of Shiraz and Cabernet Sauvignon wines made with grapes harvested at different maturity stages.

[Studies on chemical constituents from leaves of Vaccinium bracteatum].

PubMed

Li, Zeng-Liang; Zhang, Lin; Tian, Jing-Kui; Zhou, Wen-Ming

2008-09-01

To investigate the chemical constituents from the leaves of Vaccinium bracteatum. Many column chromatographic techniques were used for the isolation and separation of chemical constituents. Their structures were elucidated on the basis of spectral analysis and chemical evidences. Twelve compounds were isolated from the plant, and they were identified as chrysoeriol (1), scopoletin (2), trans-p-hydroxycinnamic acid (3), trans-p-hydroxycinnamic acid ethyl ester (4), cafeic acid ethyl ester (5), beta-sitosterol (6), iuteolin (7), quercetin (8), esculetin (9), cafeic acid (10), isolariciresinol-9-O-beta-D-xyloside (11), 10-O-trans-p-coumaroylsandoside (12). Compounds 4, 5, 11, 12 were isolated from the genus Vaccinium for the first time, and compounds 1, 2, 9, 10 were isolated from this plant for the first time.

Gas chromatography-mass spectrometry of ethyl palmitate calibration and resolution with ethyl oleate as biomarker ethanol sub acute in urine application study

NASA Astrophysics Data System (ADS)

Suaniti, Ni Made; Manurung, Manuntun

2016-03-01

Gas Chromatography-Mass Spectrometry is used to separate two and more compounds and identify fragment ion specific of biomarker ethanol such as palmitic acid ethyl ester (PAEE), as one of the fatty acid ethyl esters as early detection through conyugated reaction. This study aims to calibrate ethyl palmitate and develop analysis with oleate acid. This methode can be used analysis ethanol and its chemistry biomarker in ethanol sub-acute consumption as analytical forensic toxicology. The result show that ethanol level in urine rats Wistar were 9.21 and decreased 6.59 ppm after 48 hours consumption. Calibration curve of ethyl palmitate was y = 0.2035 x + 1.0465 and R2 = 0.9886. Resolution between ethyl palmitate and oleate were >1.5 as good separation with fragment ion specific was 88 and the retention time was 18 minutes.

Canned bluefin tuna, an in vitro cardioprotective functional food potentially safer than commercial fish oil based pharmaceutical formulations.

PubMed

Tenore, Gian Carlo; Calabrese, Giorgio; Ritieni, Alberto; Campiglia, Pietro; Giannetti, Daniela; Novellino, Ettore

2014-09-01

Commercial canned fish species typical in the Italian market were evaluated for their lipid profile. Bluefin tuna samples showed the highest content in omega-3 fatty acids (n-3 PUFA) among the canned fish samples analyzed. Tests on H9C2 cardiomyocytes revealed that bluefin tuna n-3 PUFA may responsible for a significant cell protection against both physiological and doxorubicin-induced oxidative stress. Analogous tests performed by incubating cardiac cells with n-3 PUFA ethyl esters, of which most of fish oil pharmaceutical formulations (FOPF) are based, showed cytotoxicity at high doses. Our results highlighted that n-3 PUFA contents in a 50 g canned bluefin tuna portion would be almost equivalent to and potentially safer than those of 1 FOPF capsule (1000 mg)/die usually suggested for hyperlipidaemic subjects. Thus, Italian commercial canned bluefin tuna could be indicated as a functional food with potential health benefits for the prevention and care of cardiovascular disorders. Copyright © 2014 Elsevier Ltd. All rights reserved.

Biosynthesis of polyunsaturated fatty acids in the developing brain. I. Metabolic transformations of intracranially administered 1-/sup 14/C linolenic acid. [Rats

DOE Office of Scientific and Technical Information (OSTI.GOV)

Dhopeshwarkar, G.A.; Subramanian, C.

1971-01-01

Thirteen-day old rats were given intracranial injections of 1-/sup 14/C linolenic acid (all cis 9, 12, 15 octadecatrienoic acid) and were sacrificed after 8 hr. Analysis of brain fatty acids showed that 16 : 0, 18 : 0, 18 : 1, 18 : 3, 20 : 3, 20 : 4, 20 : 5, 22 : 5 and 22 : 6 were labeled. The total fatty acid methyl esters were separated into classes according to degree of unsaturation on a AgNO/sub 3/ : SiO/sub 2/ impregnated plate. The bands were scraped off and the eluted fatty acds were first analyzed bymore » radio-gas liquid chromatography and then subjected to reductive ozonolysis to determine double bond position. The saturated acids, 16 : 0 and 18 : 0, as well as the monounsaturated 18 : 1, must have been formed from radioactive acetate produced by ..beta.. oxidation of the injected linolenate. Among the polyunsaturated fatty acids, the triene fraction was characterized and identified as 18 : 3 ..omega..3 (..delta../sup 9/,/sup 12/,/sup 15/), the starting material, and 20 : 3 ..omega..3 (..delta../sup 11/,/sup 14/,/sup 17/); the tetraene fraction was identified as 20 : 4 ..omega..3 (..delta../sup 8/,/sup 11/,/sup 14/,/sup 17/); the pentaene fraction was identified as 20 : 5 ..omega..3 (..delta../sup 5/,/sup 8/,/sup 11/,/sup 14/,/sup 17/) and 22 : 5 ..omega..3 (..delta../sup 7/,/sup 10/,/sup 13/,/sup 16/,/sup 19/); and, finally, the hexaene fraction was shown to be 22 : 6 ..omega..3 (..delta../sup 4/,/sup 7/,/sup 10/,/sup 13/,/sup 16/,/sup 19/). The biosynthesis of these ..omega..3 family fatty acids in the brain in situ is discussed.« less

Analysis of fatty acid ethyl esters in hair as possible markers of chronically elevated alcohol consumption by headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS).

PubMed

Pragst, F; Auwaerter, V; Sporkert, F; Spiegel, K

2001-09-15

Fatty acid ethyl esters (FAEE) are products of the nonoxidative ethanol metabolism, which are known to be detectable in blood only about 24h after the last alcohol intake. After deposition in hair they should be suitable long-term markers of chronically elevated alcohol consumption. Therefore, a method for the analysis of ethyl myristate, ethyl palmitate, ethyl oleate and ethyl stearate from hair was developed based on the extraction of the hair sample by a dimethylsulphoxide (DMSO)/n-hexane mixture, separation and evaporation of the n-hexane phase and application of headspace solid-phase microextraction (HS-SPME) in combination with gas chromatography-mass spectrometry (GC-MS) to the extract. For use as internal standards, the corresponding D(5)-ethyl esters were prepared. The HS-SPME/GC-MS measurements were automatically performed using a multi-purpose sampler. The detection limits of the FAEE were between 0.01 and 0.04ng/mg and the reproducibility was between 3.5 and 16%. By application of the method to hair samples of 21 fatalities with known heavy alcohol abuse 0.045-2.4ng/mg ethyl myristate, 0.35-13.5ng/mg ethyl palmitate, 0.25-7.7ng/mg ethyl oleate and 0.05-3.85ng/mg ethyl stearate were measured. For social drinkers (30-60g ethanol per week), the concentrations were about one order of magnitude smaller. For 10 teetotalers negative results or traces of ethyl palmitate were found. It was shown by supplementary investigations in single cases that FAEE are also present in sebum, that there is no strong difference in their concentrations between pubic, chest and scalp hair, and that they are detectable in hair segments after a 2 months period of abstinence. From the results follows that the measurement of FAEE concentrations in hair is a useful way for a retrospective detection of alcohol abuse.

One-pot synthesis of polyunsaturated fatty acid amides with anti-proliferative properties.

PubMed

Tremblay, Hugo; St-Georges, Catherine; Legault, Marc-André; Morin, Caroline; Fortin, Samuel; Marsault, Eric

2014-12-15

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. Copyright © 2014 Elsevier Ltd. All rights reserved.

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2012 CFR

2012-07-01

...-0319306979-40-8 Poly(oxy-1,2-ethanediyl), .alpha.-[2-(methylamino)ethyl]-.omega.-[(1,1,3,3-tetramethylbutyl...]amino]ethyl]-.omega.-hydroxy- 38850-52-1 1-Propanaminium, 3-[(carboxymethyl)[(1,1,2,2,3,3,4,4,5,5,6,6,6...-heptadecafluorooctyl)sulfonyl]methylamino]carbonyl]-.omega.-butoxy- 52166-82-2 1-Propanaminium, N,N,N-trimethyl-3-[[(1...

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2013 CFR

2013-07-01

...-0319306979-40-8 Poly(oxy-1,2-ethanediyl), .alpha.-[2-(methylamino)ethyl]-.omega.-[(1,1,3,3-tetramethylbutyl...]amino]ethyl]-.omega.-hydroxy- 38850-52-1 1-Propanaminium, 3-[(carboxymethyl)[(1,1,2,2,3,3,4,4,5,5,6,6,6...-heptadecafluorooctyl)sulfonyl]methylamino]carbonyl]-.omega.-butoxy- 52166-82-2 1-Propanaminium, N,N,N-trimethyl-3-[[(1...

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2011 CFR

2011-07-01

...-0319306979-40-8 Poly(oxy-1,2-ethanediyl), .alpha.-[2-(methylamino)ethyl]-.omega.-[(1,1,3,3-tetramethylbutyl...]amino]ethyl]-.omega.-hydroxy- 38850-52-1 1-Propanaminium, 3-[(carboxymethyl)[(1,1,2,2,3,3,4,4,5,5,6,6,6...-heptadecafluorooctyl)sulfonyl]methylamino]carbonyl]-.omega.-butoxy- 52166-82-2 1-Propanaminium, N,N,N-trimethyl-3-[[(1...

40 CFR 721.9582 - Certain perfluoroalkyl sulfonates.

Code of Federal Regulations, 2010 CFR

2010-07-01

...-0319306979-40-8 Poly(oxy-1,2-ethanediyl), .alpha.-[2-(methylamino)ethyl]-.omega.-[(1,1,3,3-tetramethylbutyl...]amino]ethyl]-.omega.-hydroxy- 38850-52-1 1-Propanaminium, 3-[(carboxymethyl)[(1,1,2,2,3,3,4,4,5,5,6,6,6...-heptadecafluorooctyl)sulfonyl]methylamino]carbonyl]-.omega.-butoxy- 52166-82-2 1-Propanaminium, N,N,N-trimethyl-3-[[(1...

Functionalization of 6-nitrobenzo[1,3]dioxole with carbonyl compounds via TDAE methodology.

PubMed

Amiri-Attou, Ouassila; Terme, Thierry; Vanelle, Patrice

2005-05-13

We report herein the synthesis of substituted 2-(6-nitrobenzo[1,3]dioxol-5-yl)-1- aryl ethanols and 2-(6-nitrobenzo[1,3]dioxol-5-yl)-propionic acid ethyl esters from the reaction of 5-chloromethyl-6-nitrobenzo[1,3]dioxole with various aromatic carbonyl and alpha- carbonyl ester derivatives using the tetrakis(dimethylamino)ethylene (TDAE) methodology.

Control of postharvest Botrytis fruit rot of strawberry by volatile organic compounds of Candida intermedia.

PubMed

Huang, R; Li, G Q; Zhang, J; Yang, L; Che, H J; Jiang, D H; Huang, H C

2011-07-01

A study was conducted to identify volatile organic compounds or volatiles produced by Candida intermedia strain C410 using gas chromatography-mass spectrometry, and to determine efficacy of the volatiles of C. intermedia in suppression of conidial germination and mycelial growth of Botrytis cinerea and control of Botrytis fruit rot of strawberry. Results showed that, among 49 volatiles (esters, alcohols, alkenes, alkanes, alkynes, organic acids, ketones, and aldehydes) identified from C. intermedia cultures on yeast extract peptone dextrose agar, two compounds, 1,3,5,7-cyclooctatetraene and 3-methyl-1-butanol, were the most abundant. Synthetic chemicals of 1,3,5,7-cyclooctatetraene; 3-methyl-1-butanol; 2-nonanone; pentanoic acid, 4-methyl-, ethyl ester; 3-methyl-1-butanol, acetate; acetic acid, pentyl ester; and hexanoic acid, ethyl ester were highly inhibitory to conidial germination and mycelial growth of B. cinerea. Inhibition of conidial germination and mycelial growth of B. cinerea by volatiles of C. intermedia was also observed. Meanwhile, results showed that incidence and severity of Botrytis fruit rot of strawberry was significantly (P < 0.01) reduced by exposure of the strawberry fruit to the volatiles from C. intermedia cultures or C. intermedia-infested strawberry fruit. These results suggest that the volatiles of C. intermedia C410 are promising biofumigants for control of Botrytis fruit rot of strawberry.

Production and Characterization of Ethyl Ester from Crude Jatropha curcas Oil having High Free Fatty Acid Content

NASA Astrophysics Data System (ADS)

Kumar, Rajneesh; Dixit, Anoop; Singh, Shashi Kumar; Singh, Gursahib; Sachdeva, Monica

2015-09-01

The two step process was carried out to produce biodiesel from crude Jatropha curcas oil. The pretreatment process was carried out to reduce the free fatty acid content by (≤2 %) acid catalyzed esterification. The optimum reaction conditions for esterification were reported to be 5 % H2SO4, 20 % ethanol and 1 h reaction time at temperature of 65 °C. The pretreatment process reduced the free fatty acid of oil from 7 to 1.85 %. In second process, alkali catalysed transesterification of pretreated oil was carried and the effects of the varying concentrations of KOH and ethanol: oil ratios on percent ester recovery were investigated. The optimum reaction conditions for transesterification were reported to be 3 % KOH (w/v of oil) and 30 % (v/v) ethanol: oil ratio and reaction time 2 h at 65 °C. The maximum percent recovery of ethyl ester was reported to be 60.33 %.

Synthesis of carboxylic acids, esters, alcohols and ethers containing a tetrahydropyran ring derived from 6-methyl-5-hepten-2-one.

PubMed

Hanzawa, Yohko; Hashimoto, Kahoko; Kasashima, Yoshio; Takahashi, Yoshiko; Mino, Takashi; Sakamoto, Masami; Fujita, Tsutomu

2012-01-01

3-hydroxy acids, 3-hydroxy-3,7-dimethyloct-6-enoic acid (1) and 3-hydroxy-2,2,3,7-tetramethyloct-6-enoic acid (2), were prepared from 6-methyl-5-hepten-2-one, and they were subsequently used to prepare (2,6,6-trimethyltetrahydropyran-2-yl)acetic acid (3) and 2-methyl-2-(2,6,6-trimethyltetrahydropyran-2-yl)propanoic acid (4), respectively, via cyclization with an acidic catalyst such as boron trifluoride diethyl etherate or iodine. The reaction of carboxylic acids 3 and 4 with alcohols, including methanol, ethanol, and 1-propanol, produced the corresponding methyl, ethyl, and propyl esters, which all contained a tetrahydropyran ring. Reduction of carboxylic acids 3 and 4 afforded the corresponding alcohols. Subsequent reactions of these alcohols with several acyl chlorides produced novel esters. The alcohols also reacted with methyl iodide and sodium hydride to provide novel ethers. A one-pot cyclization-esterification of 1 to produce esters containing a tetrahydropyran ring, using iodine as a catalyst, was also investigated.

Effects of prescription niacin and omega-3 fatty acids on lipids and vascular function in metabolic syndrome: a randomized controlled trial[S

PubMed Central

Shearer, Gregory C.; Pottala, James V.; Hansen, Susan N.; Brandenburg, Verdayne; Harris, William S.

2012-01-01

The metabolic syndrome includes both dyslipidemia and impaired vascular function. Because extended-release niacin (ERN) and prescription omega-3 acid ethyl-esters (P-OM3) independently improve these characteristics, we tested their effects in combination. Sixty metabolic syndrome subjects were randomized to 16 weeks of treatment on dual placebo, P-OM3 (4g/day), ERN (2 g/day), or combination in a double-blind trial. Lipoprotein subfractions and vascular endpoints were measured and tested using ANCOVA. ERN increased HDL cholesterol by 5.4 mg/dl from baseline (P = 0.04), decreased triglycerides (TG) by 39 mg/dl (−21%, P = 0.003), and decreased the augmentation index, which is a measure of vascular stiffness, by 3.5 units (P = 0.04). P-OM3 reduced TG by 26 mg/dl (−13%, P = 0.04). Combination treatment increased HDL cholesterol by 7.8 mg/dl (P = 002) and decreased TG by 72 mg/dl (−34%) but there was no improvement in vascular stiffness. Detailed analysis of lipoprotein subfractions revealed increased large, bouyant HDL2 (3.3 mg/dl; P = 0.002) and decreased VLDL1+2 (−32%; P < 0.0001), among subjects treated with combination therapy, that were not present with either therapy alone. ERN and P-OM3 alone improved characteristics of metabolic syndrome; however, whereas subjects on combination therapy did not have improved vascular stiffness, TG and HDL levels improved as did certain lipoprotein subfractions. PMID:22892157

Functional analyses on antioxidant, anti-inflammatory, and antiproliferative effects of extracts and compounds from Ilex latifolia Thunb., a Chinese bitter tea.

PubMed

Hu, Ting; He, Xiao-Wei; Jiang, Jian-Guo

2014-08-27

Ilex latifolia Thunb., widely distributed in China, has been used as a functional food and drunk for a long time. This study was aimed to identify the bioactive constituents with antioxidant, antitumor, and anti-inflammatory properties. I. latifolia was extracted with 95% ethanol and then partitioned into four fractions: petroleum ether fraction, ethyl acetate fraction, n-butanol fraction, and water fraction. Results showed that the ethyl acetate fraction was found to have significant ferric reducing antioxidant power activity, DPPH radical scavenging activity, and oxygen radical absorbance capacity, cytotoxicity against human cervix carcinoma HeLa cells, and inhibitory effect on NO production in macrophage RAW 264.7 cells. Five compounds were isolated from the ethyl acetate fraction, and they were identified as ethyl caffeate (1), ursolic acid (2), chlorogenic acid (3), 3,4-di-O-caffeoylquinic acid methyl ester (4), and 3,5-di-O-caffeoylquinic acid methyl ester (5), the last two of which were isolated for the first time from I. latifolia. Compounds 4 and 5 exhibited cytotoxicity actions against tumor cell line. Compound 3 showed the strongest anti-inflammatory activity of all the compounds. The results obtained in this work might contribute to the understanding of biological activities of I. latifolia and further investigation on its potential application values for food and drug.

[Study on the chemical constituents from Clematis brevicaudata].

PubMed

Yang, Ai-Mei; Du, Jing; Miao, Zhong-Huan; Yuan, Hui-Jun

2009-10-01

To study the chemical constituents from Clematis brevicaudata. The compounds were isolated by column chromatography and their structures were elucidated through spectroscopic analysis (NMR). Eight compounds were isolated and identified as: palmitic acid (1), 1-docosanol (2), pentacosanoic acid-2', 3'-dihydroxypropyl ester (3), beta-sitosterol (4), daucosterol (5), a mixture of the trans-p-coumarate of the n-alkanols (6), 3,4-dihydroxy-trans coumatate ethyl ester (7), syringaresinol-O-D-glucopyranoside (8). All these compounds are obtained from Clematis brevicaudata for the first time.

40 CFR 721.10072 - Benzene, 1,1′-methylenebis[4-isocyanato-, polymer with benzenedicarboxylic acid, butyl dialkyl...

Code of Federal Regulations, 2010 CFR

2010-07-01

...-isocyanato-, polymer with benzenedicarboxylic acid, butyl dialkyl ester, poly[oxy(methyl-1,2-ethanediyl)], .alpha.-hydro-.omega.-hydroxy-, oxirane, alkyl-, polymer with oxirane, ether with propanepolyol and...-isocyanato-, polymer with benzenedicarboxylic acid, butyl dialkyl ester, poly[oxy(methyl-1,2-ethanediyl...

40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2'-(1,2-diazenediyl)bis[2-methylbutanenitrile]- and 2,2'-(1,2-diazenediyl)bis[2-methylpropanenitrile]-initiated. 721.10326...

Monitoring codling moth (Lepidoptera: Tortricidae) in sex phermone-treated orchards with (E)-4,8-dimethyl-1,3,7-nonatriene or pear ester in combination with codlemone and acetic acid

USDA-ARS?s Scientific Manuscript database

Traps baited with ethyl (E,Z)-2,4-decadienoate (pear ester) or (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT) in two- or three-way combinations with the sex pheromone (E,E)-8,10-dodecadien-1-ol (codlemone) and acetic acid (AA) were evaluated for codling moth, Cydia pomonella (L.). All studies were conduct...

Efficient synthesis of (+/-)-4-methyloctanoic acid, aggregation pheromone of rhinoceros beetles of the genus Oryctes (Coleoptera: Dynastidae, Scarabaeidae).

PubMed

Ragoussis, Valentine; Giannikopoulos, Alexandros; Skoka, Efthymia; Grivas, Panagiotis

2007-06-27

(+/-)-4-Methyloctanoic acid and its ethyl ester are aggregation pheromones of many rhinoceros beetles of the genus Oryctes and are investigated for the control of these pests by olfactory trapping. A simple, economical, and high-yield (>50%) synthesis of (+/-)-4-methyloctanoic acid and its ethyl ester is presented starting from n-hexanal. The key step in this sequence is an orthoester Claisen rearrangement for the elongation of the carbon chain by two.

75 FR 37738 - 1-Naphthaleneacetic Acid; Time-Limited Tolerance, Technical Correction

Federal Register 2010, 2011, 2012, 2013, 2014

2010-06-30

...-Naphthaleneacetic Acid; Time-Limited Tolerance, Technical Correction AGENCY: Environmental Protection Agency (EPA..., ethylene oxide, fenvalerate, et al.; tolerance actions. Today's rule restores the time-limited tolerance...-3) establishing a time-limited tolerance for residues of 1-naphthaleneacetic acid ethyl ester in or...

Biocatalytic Asymmetric Synthesis of (1R, 2S)-N-Boc-vinyl-ACCA Ethyl Ester with a Newly Isolated Sphingomonas aquatilis.

PubMed

Zhu, Shaozhou; Shi, Ying; Zhang, Xinyu; Zheng, Guojun

2018-02-01

1-amino cyclopropane-1-carboxylic acid (ACCA) and its derivatives are essential pharmacophoric unit that widely used in drug research and development. Specifically, (1R, 2S)-N-Boc-vinyl-ACCA ethyl ester (vinyl-ACCA) is a key chiral intermediate in the synthesis of highly potent hepatitis C virus (HCV) NS3/4A protease inhibitors such as asunaprevir and simeprevir. Developing strategies for the asymmetric synthesis of vinyl-ACCA is thus extremely high demand. In this study, 378 bacterial strains were isolated from soil samples using N-Boc-vinyl-ACCA ethyl ester as the sole carbon source and were screened for esterase activity. Fourteen of which worked effectively for the asymmetric synthesis of (1R, 2S)-N-Boc-1-vinyl ACCA ethyl ester. The strain CY-2, identified as Sphingomonas aquatilis, which showed the highest stability and enantioselectivity was selected as whole cell biocatalyst for further study. A systematic study of all factors influencing the enzymatic hydrolysis was performed. Under optimized conditions, resolution of rac-vinyl-ACCA to (1R, 2S)-N-Boc-1-vinyl ACCA ethyl ester with 88.2% ee and 62.4% conversion (E = 9) was achieved. Besides, S. aquatilis was also used to transform other 10 different substrates. Notably, it was found that 7 of them could be stereoselectively hydrolyzed, especially for (1R,2S)-1-amino-vinyl-ACCA ethyl ester hydrochloride (99.6% ee, E>200). Our investigations provide a new efficient whole cell biocatalyst for resolution of ACCA and might be developed for industry application.

Determination of selected fate and aquatic toxicity characteristics of acrylic acid and a series of acrylic esters.

PubMed

Staples, C A; Murphy, S R; McLaughlin, J E; Leung, H W; Cascieri, T C; Farr, C H

2000-01-01

Acrylic acid, methyl acrylate, ethyl acrylate, and butyl acrylate are commercially important and widely used materials. This paper reports the results of a series of fate and aquatic toxicity studies. The mobility in soil of acrylic acid and its esters ranged from 'medium' to 'very high'. Calculated bioconcentration factors ranged from 1 to 37, suggesting a low bioconcentration potential. Acrylic acid and methyl acrylate showed limited biodegradability in the five day biochemical oxygen demand (BOD5) test, while ethyl acrylate and butyl acrylate were degraded easily (77% and 56%, respectively). Using the OECD method 301D 28-d closed bottle test, degradability for acrylic acid was 81% at 28 days, while the acrylic esters ranged from 57% to 60%. Acrylic acid degraded rapidly to carbon dioxide in soil (t1/2 < 1 day). Toxicity tests were conducted using freshwater and marine fish, invertebrates, and algae. Acrylic acid effect concentrations for fish and invertebrates ranged from 27 to 236 mg/l. Effect concentrations (LC50 or EC50) for fish and invertebrates using methyl acrylate, ethyl acrylate, and butyl acrylate ranged from 1.1 to 8.2 mg/l. The chronic MATC for acrylic acid with Daphnia magna was 27 mg/l based on length and young produced per adult reproduction day and for ethyl acrylate was 0.29 mg/l based on both the reproductive and growth endpoints. Overall these studies show that acrylic acid and the acrylic esters studied can rapidly biodegrade, have a low potential for persistence or bioaccumulation in the environment, and have low to moderate toxicity.

Cardiovascular disease and omega-3s: Prescription products and fish oil dietary supplements are not the same.

PubMed

Gutstein, Adina S; Copple, Tina

2017-12-01

Despite achievement of optimal low-density lipoprotein cholesterol (LDL-C) control with statin therapy, patients with elevated triglycerides (TGs) and residual cardiovascular risk are commonly encountered in clinical practice. We present information from completed and ongoing clinical trials examining Rx omega-3s for TG-lowering and omega-3 dietary supplements to highlight important differences affecting patient management for nurse practitioners. Rx omega-3s demonstrate robust reductions in TGs and may have a role in reducing residual cardiovascular risk. Products containing docosahexaenoic acid (DHA) may raise LDL-C and should not be substituted for Rx eicosapentaenoic acid (EPA)-only icosapent ethyl, which does not raise LDL-C. Omega-3 dietary supplements (e.g., fish oils containing EPA and DHA) may be used for general health promotion; however, they are not regulated as medications and concerns regarding quality, purity, safety, and variability of content exist. It is important to advise patients that omega-3 dietary supplements are not medications and should not be substituted for Rx omega-3s. Large-scale cardiovascular outcomes studies are underway for Rx omega-3s in statin-treated patients. Nurse practitioners can take an active role in reducing residual cardiovascular risk and educating patients about important differences between Rx omega-3s and fish oil supplements. ©2017 American Association of Nurse Practitioners.

Omega-3 free fatty acids for the treatment of severe hypertriglyceridemia: the EpanoVa fOr Lowering Very high triglyceridEs (EVOLVE) trial.

PubMed

Kastelein, John J P; Maki, Kevin C; Susekov, Andrey; Ezhov, Marat; Nordestgaard, Borge G; Machielse, Ben N; Kling, Douglas; Davidson, Michael H

2014-01-01

Omega-3 fatty acids in free fatty acid form have enhanced bioavailability, and plasma levels are less influenced by food than for ethyl ester forms. The aim was to evaluate the safety and lipid-altering efficacy in subjects with severe hypertriglyceridemia of an investigational pharmaceutical omega-3 free fatty acid (OM3-FFA) containing eicosapentaenoic acid and docosahexaenoic acid. This was a multinational, double-blind, randomized, out-patient study. Men and women with triglycerides (TGs) ≥ 500 mg/dL, but <2000 mg/dL, took control (olive oil [OO] 4 g/d; n = 99), OM3-FFA 2 g/d (plus OO 2 g/d; n = 100), OM3-FFA 3 g/d (plus OO 1 g/d; n = 101), or OM3-FFA 4 g/d (n = 99) capsules for 12 weeks in combination with the National Cholesterol Education Program Therapeutic Lifestyle Changes diet. Fasting serum TGs changed from baseline by -25.9% (P < .01 vs OO), -25.5% (P < .01 vs OO), and -30.9% (P < .001 vs OO) with 2, 3, and 4 g/d OM3-FFA, respectively, compared with -4.3% with OO. Non-high-density lipoprotein cholesterol (non-HDL-C), total cholesterol-to-HDL-C ratio, very low-density lipoprotein cholesterol, remnant-like particle cholesterol, apolipoprotein CIII, lipoprotein-associated phospholipase A2, and arachidonic acid were significantly lowered (P < .05 at each OM3-FFA dosage vs OO); and plasma eicosapentaenoic acid and docosahexaenoic acid were significantly elevated (P < .001 at each OM3-FFA dosage vs OO). With OM3-FFA 2 and 4 g/d (but not 3 g/d), low-density lipoprotein cholesterol was significantly increased compared with OO (P < .05 vs OO). High-sensitivity C-reactive protein responses with OM3-FFA did not differ significantly from the OO response at any dosage. Fewer subjects reported any adverse event with OO vs OM3-FFA, but frequencies across dosage groups were similar. Discontinuation due to adverse event, primarily gastrointestinal, ranged from 5% to 7% across OM3-FFA dosage groups vs 0% for OO. OM3-FFA achieved the primary end point for TG lowering and secondary end point of non-HDL-C lowering at 2, 3, and 4 g/d in persons with severe hypertriglyceridemia. This trial was registered at www.clinicaltrials.gov as NCT01242527. Copyright © 2014 National Lipid Association. Published by Elsevier Inc. All rights reserved.

Studies on performance evaluation of a green plasticizer made by enzymatic esterification of furfuryl alcohol and castor oil fatty acid.

PubMed

Mukherjee, Sohini; Ghosh, Mahua

2017-02-10

The esterification of furfuryl alcohol (FA) and castor oil fatty acid (COFA) at 3:1 molar ratio, by immobilized Candida antarctica Lipase B (NS 435 from Novozyme) in a solvent free system gave a maximum yield of 88.64% (%w/w) at 5h. Performance of the FA-COFA ester plasticized Ethyl Cellulose (EC) films were evaluated by surface morphologies, XRD analysis, mechanical properties,thermal properties, water vapor permeability and migration stability test. It was an effective plasticizer with better mechanical properties and thermal stability at the increasing concentration of FA-COFA ester (15-25%) containing EC film, than the traditional plasticizer, i.e; dibutyl phthalate (DBP) in producing good quality films. Chemical structure and the intermolecular interactions between FA-COFA ester and ethyl cellulose chains were the causative agents of these outstanding performances. Therefore, this FA-COFA ester, with significant plasticizing property, at a certain concentration, can be a substitute of DBP. Copyright © 2016 Elsevier Ltd. All rights reserved.

40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2â²-(1,2-diazenediyl)bis[2-methylbutanenitrile]- and 2,2â²-(1,2-diazenediyl)bis[2-methylpropanenitrile]-initiated. 721.10326...

40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2â²-(1,2-diazenediyl)bis[2-methylbutanenitrile]- and 2,2â²-(1,2-diazenediyl)bis[2-methylpropanenitrile]-initiated. 721.10326...

Orosensory-directed identification of astringent mouthfeel and bitter-tasting compounds in red wine.

PubMed

Hufnagel, Jan Carlos; Hofmann, Thomas

2008-02-27

Application of sequential solvent extraction, followed by HPLC combined with the taste dilution analysis, enabled the localization of the most intense velvety astringent, drying, and puckering astringent, as well as bitter-tasting, compounds in red wine, respectively. Isolation of the taste components involving gel adsorption chromatography, ultrafiltration, and synthesis revealed the identification of 26 sensory-active nonvolatiles, among which several hydroxybenzoic acids, hydroxycinnamic acids, flavon-3-ol glycosides, and dihydroflavon-3-ol rhamnosides as well as a structurally undefined polymeric fraction (>5 kDa) were identified as the key astringent components. In contradiction to literature suggestions, flavan-3-ols were found to be not of major importance for astringency and bitter taste, respectively. Surprisingly, a series of hydroxybenzoic acid ethyl esters and hydroxycinnamic acid ethyl esters were identified as bitter compounds in wine. Taste qualities and taste threshold concentrations of the individual wine components were determined by means of a three-alternative forced-choice test and the half-mouth test, respectively.

[Studies on chemical constituents of Valeriana officinalis].

PubMed

Jiang, Xia; Zhang, Jian-chao; Liu, Yan-wen; Fang, Yin

2007-11-01

From Valeriana officinalis L., 4 compounds were isolated and identified by various spectral analysis and chemical conversion, as valerenic acid, beta-sitosterol, ursolic acid, 4, 4', 8, 8'-tetrahydroxy-3, 3'-dimethoxyl-dibenzyl-ditetrahydrofuran and caryophyllene acide,valerane, naphthalene, linoleic acid, ethyl ester, myrtenyl acetate were identified by GC-MS. Ursolic acid and 4, 4', 8, 8'-tetrahydroxy-3, 3'-dimethoxyl-dibenzyl-ditetrahydrofuran were discovered in this plant for the first time.

Biologic plausibility, cellular effects, and molecular mechanisms of eicosapentaenoic acid (EPA) in atherosclerosis.

PubMed

Borow, Kenneth M; Nelson, John R; Mason, R Preston

2015-09-01

Residual cardiovascular (CV) risk remains in dyslipidemic patients despite intensive statin therapy, underscoring the need for additional intervention. Eicosapentaenoic acid (EPA), an omega-3 polyunsaturated fatty acid, is incorporated into membrane phospholipids and atherosclerotic plaques and exerts beneficial effects on the pathophysiologic cascade from onset of plaque formation through rupture. Specific salutary actions have been reported relating to endothelial function, oxidative stress, foam cell formation, inflammation, plaque formation/progression, platelet aggregation, thrombus formation, and plaque rupture. EPA also improves atherogenic dyslipidemia characterized by reduction of triglycerides without raising low-density lipoprotein cholesterol. Other beneficial effects of EPA include vasodilation, resulting in blood pressure reductions, as well as improved membrane fluidity. EPA's effects are at least additive to those of statins when given as adjunctive therapy. In this review, we present data supporting the biologic plausibility of EPA as an anti-atherosclerotic agent with potential clinical benefit for prevention of CV events, as well as its cellular effects and molecular mechanisms of action. REDUCE-IT is an ongoing, randomized, controlled study evaluating whether the high-purity ethyl ester of EPA (icosapent ethyl) at 4 g/day combined with statin therapy is superior to statin therapy alone for reducing CV events in high-risk patients with mixed dyslipidemia. The results from this study are expected to clarify the role of EPA as adjunctive therapy to a statin for reduction of residual CV risk. Copyright © 2015 The Authors. Published by Elsevier Ireland Ltd.. All rights reserved.

Impact of temperature on fatty acid composition and nutritional value in eight species of microalgae.

PubMed

Aussant, Justine; Guihéneuf, Freddy; Stengel, Dagmar B

2018-06-01

Microalgae are considered a sustainable source of high-value products with health benefits. Marine algae-derived omega-3 long-chain polyunsaturated fatty acids (LC-PUFA), such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), are considered dietary elements with effects on mental health, cognition enhancement, and cardiovascular protection. This study investigated the temperature effect on omega-3 LC-PUFA production in eight species of microalgae from various taxonomic groups, with a focus on achieving an optimal balance between omega-3 accumulation and efficient growth performance. Samples were batch-cultivated at four different temperatures, with constant light, and fatty acid methyl esters (FAME) were analyzed by gas chromatography. Several nutritional indices were calculated to assess the potential value of biomass produced for human consumption. Two promising candidates were identified suitable for batch cultivation and large-scale production: Nannochloropsis oculata for EPA and Isochrysis galbana for DHA production, with optimum productivities obtained between 14 and 20 °C, and nutritional indices falling within the range required for nutritional benefit.

Synthesis of structured lipid enriched with omega fatty acids and sn-2 palmitic acid by enzymatic esterification and its incorporation in powdered infant formula.

PubMed

Nagachinta, Supakana; Akoh, Casimir C

2013-05-08

Structured lipid (SL) enriched with arachidonic (ARA) and docosahexaenoic (DHA) acids was produced from tripalmitin using Lipozyme TL IM. The effects of acyl donors, that is, free fatty acids vs fatty acid ethyl esters, on the reactions were compared. The highest total incorporation of ARA and DHA was obtained when the reaction continued for 24 h, at a substrate mole ratio of 9, using free fatty acids as acyl donors (acidolysis). The SL prepared by a large-scale acidolysis reaction contained 17.69 ± 0.09% total ARA, 10.75 ± 0.15% total DHA, and 48.53 ± 1.40% sn-2 palmitic acid. SL thermograms exhibited multiple peaks indicating complexity of the triacylglycerol (TAG) distribution. RP-HPLC analysis of SL revealed nine of 26 TAG molecular species that were similar to those of human milk fat. Powdered infant formulas containing the SL were prepared by wet-mixing/spray-drying and dry-blending methods. Formula prepared with microencapsulated SL and the dry-blending method had better oxidative stability and color quality.

Reactive Distillation for Esterification of Bio-based Organic Acids

DOE Office of Scientific and Technical Information (OSTI.GOV)

Fields, Nathan; Miller, Dennis J.; Asthana, Navinchandra S.

2008-09-23

The following is the final report of the three year research program to convert organic acids to their ethyl esters using reactive distillation. This report details the complete technical activities of research completed at Michigan State University for the period of October 1, 2003 to September 30, 2006, covering both reactive distillation research and development and the underlying thermodynamic and kinetic data required for successful and rigorous design of reactive distillation esterification processes. Specifically, this project has led to the development of economical, technically viable processes for ethyl lactate, triethyl citrate and diethyl succinate production, and on a larger scalemore » has added to the overall body of knowledge on applying fermentation based organic acids as platform chemicals in the emerging biorefinery. Organic acid esters constitute an attractive class of biorenewable chemicals that are made from corn or other renewable biomass carbohydrate feedstocks and replace analogous petroleum-based compounds, thus lessening U.S. dependence on foreign petroleum and enhancing overall biorefinery viability through production of value-added chemicals in parallel with biofuels production. Further, many of these ester products are candidates for fuel (particularly biodiesel) components, and thus will serve dual roles as both industrial chemicals and fuel enhancers in the emerging bioeconomy. The technical report from MSU is organized around the ethyl esters of four important biorenewables-based acids: lactic acid, citric acid, succinic acid, and propionic acid. Literature background on esterification and reactive distillation has been provided in Section One. Work on lactic acid is covered in Sections Two through Five, citric acid esterification in Sections Six and Seven, succinic acid in Section Eight, and propionic acid in Section Nine. Section Ten covers modeling of ester and organic acid vapor pressure properties using the SPEAD (Step Potential Equilibrium and Dynamics) method.« less

Rapid screening of fatty acid alkyl esters in olive oils by time domain reflectometry.

PubMed

Berardinelli, Annachiara; Ragni, Luigi; Bendini, Alessandra; Valli, Enrico; Conte, Lanfranco; Guarnieri, Adriano; Toschi, Tullia Gallina

2013-11-20

The main aim of the present research is to assess the possibility of quickly screening fatty acid alkyl esters (FAAE) in olive oils using time domain reflectometry (TDR) and partial least-squares (PLS) multivariate statistical analysis. Eighteen virgin olive oil samples with fatty acid alkyl ester contents and fatty acid ethyl ester/methyl ester ratios (FAEE/FAME) ranging from 3 to 100 mg kg(-1) and from 0.3 to 2.6, respectively, were submitted to tests with time domain resolution of 1 ps. The results obtained in test set validation demonstrated that this new and fast analytical approach is able to predict FAME, FAEE, and FAME + FAEE contents with R(2) values of 0.905, 0.923, and 0.927, respectively. Further measurements on mixtures between olive oil and FAAE standards confirmed that the prediction is based on a direct influence of fatty acid alkyl esters on the TDR signal. The suggested technique appeared potentially suitable for monitoring one of the most important quality attribute of the olive oil in the extraction process.

Direct conversion of wet algae to crude biodiesel under supercritical ethanol conditions

DOE Office of Scientific and Technical Information (OSTI.GOV)

Reddy, Harvind K.; Muppaneni, Tapaswy; Patil, Prafulla D.

This paper presents a single-step, environmentally friendly approach for the direct conversion of wet algae to crude biodiesel under supercritical ethanol conditions. Ethanol was used for the simultaneous extraction and transesterification of lipids in algae to produce fatty acid ethyl esters at supercritical conditions. In this work the effects of process parameters dry algae to ethanol (wt./vol.) ratio (1:6-1:15), reaction temperature (245-270 C), and reaction time (2-30 min.) on the yield of fatty acid ethyl esters (FAEE) were studied. 67% conversion was achieved at 265 C and 20 min of reaction time. The calorific value of a purified biodiesel samplemore » produced at optimum conditions was measured to be 43 MJ/kg, which is higher than that of fatty acid methyl esters produced from the same biomass. The purified fatty acid ethyl esters were analyzed using GC-MS and FTIR. TGA analysis of algal biomass and purified FAEE was presented along with TEM images of the biomass captured before and after supercritical ethanol transesterification. This green conversion process has the potential to provide an energy-efficient and economical route for the production of renewable biodiesel production.« less

[Study on chemical constituents from ethyl acetate extract of Myricaria bracteata].

PubMed

Zhang, Ying; Yuan, Yi; Cui, Baosong; Li, Shuai

2011-04-01

To study the chemical constituents from the ethyl acetate extract of Myricaria bracteata. The chemical constituents were isolated and purified by chromatographic techniques, and their structures were identified by physical characters and spectroscopic analysis. Sixteen compounds were isolated from the ethyl acetate portion of the 95% ethanolic extract of Myricaria bracteata, and identified as myricarin (1), myricarin B (2), 3alpha-hydroxytaraxer-14-en-28-oic acid (3), myricadiol (4), trans-ferulic acid 22-hydroxydocosanoic acid ester (5), docosyl-3, 4-dihydroxy-trans-cinnamate (6), dillenetin (7), 3, 5, 4'-trihydroxy-7-methoxyflavone (8), 3, 5, 4'-trihydroxy-7, 3'-dimethoxyflavone (9), methyl 3, 5-dihydroxy-4-methoxybenzoate (10), 3-hydroxy-4-methoxy cinnamic acid (11), sinapaldehyde (12), vanillin (13), syringaldehyde (14), 3, 3', 4'-trimethoxyellagic acid (15), methyl p-hyroxybenzoate (16). Compounds 5, 6, 12-16 were isolated from the genus Myricaria for the fist time, all of the compounds were isolated from this plant for the fist time, except for 8 and 9.

Phenolic derivatives from soy flour ethanol extract are potent in vitro quinone reductase (QR) inducing agents.

PubMed

Bolling, Bradley W; Parkin, Kirk L

2008-11-26

The fractionation of soy flour directed by a cellular bioassay for induction of phase 2 detoxification enzymes was used to identify quinone reductase (QR) inducing agents. A phospholipid-depleted, 80% methanol-partitioned isolate from a crude ethanol extract of soy flour was resolved using normal phase medium-pressure liquid chromatography (MPLC). Early eluting fractions were found to be the most potent QR inducing agents among the separated fractions. Fraction 2 was the most potent, doubling QR at <2 mug/mL. Further fractionation of this isolate led to the identification of several constituents. Fatty acids and sn-1 and sn-2 monoacylglycerols were identified, but were not highly potent QR inducers. Benzofuran-3-carbaldehyde, 4-hydroxybenzaldeyde, 4-ethoxybenzoic acid, 4-ethoxycinnamic acid, benzofuran-2-carboxylic ethyl ester, and ferulic acid ethyl ester (FAEE) were also identified as QR inducing constituents of this fraction. FAEE was the most potent of the identified constituents, doubling QR specific activity at 3.2 muM in the cellular bioassay.

Cocrystallization out of the blue: DL-mandelic acid/ethyl-DL-mandelate cocrystal

NASA Astrophysics Data System (ADS)

Tumanova, Natalia; Payen, Ricky; Springuel, Géraldine; Norberg, Bernadette; Robeyns, Koen; Le Duff, Cécile; Wouters, Johan; Leyssens, Tom

2017-01-01

This work focuses on a peculiar behavior of racemic mandelic acid in ethanol solution. Dissolution of racemic mandelic acid in ethanol followed by evaporation to dryness results in a DL-mandelic acid/ethyl-DL-mandelate cocrystal. This behavior indicates that racemic mandelic acid tends not only to transform into an ester in ethanol, but also to cocrystallize with untransformed acid molecules. Cocrystal formation for mandelic acid in ethanol was found to be reproducible under various conditions. DL-tropic acid and DL-phenyllactic acid that contain similar functional groups and that were tested as well, on the other hand, showed no cocrystal formation: DL-phenyllactic acid partly converted into an ester, whereas DL-tropic acid mostly recrystallized.

Solid dispersions of the penta-ethyl ester prodrug of diethylenetriaminepentaacetic acid (DTPA): Formulation design and optimization studies

PubMed Central

Yang, Yu-Tsai; Di Pasqua, Anthony J.; Zhang, Yong; Sueda, Katsuhiko; Jay, Michael

2015-01-01

The penta-ethyl ester prodrug of diethylenetriaminepentaacetic acid (DTPA), which exists as an oily liquid, was incorporated into a solid dispersion for oral administration by the solvent evaporation method using blends of polyvinylpyrrolidone (PVP), Eudragit® RL PO and α-tocopherol. D-optimal mixture design was used to optimize the formulation. Formulations that had a high concentration of both Eudragit® RL PO and α-tocopherol exhibited low water absorption and enhanced stability of the DTPA prodrug. Physicochemical properties of the optimal formulation were evaluated using Fourier transform infrared (FTIR) spectroscopy and differential scanning calorimetry (DSC). In vitro release of the prodrug was evaluated using the USP Type II apparatus dissolution method. DSC studies indicated that the matrix had an amorphous structure, while FTIR spectrometry showed that DTPA penta-ethyl ester and excipients did not react with each other during formation of the solid dispersion.. Dissolution testing showed that the optimized solid dispersion exhibited a prolonged release profile, which could potentially result in a sustained delivery of DTPA penta-ethyl to enhance bioavailability. In conclusion, DTPA penta-ethyl ester was successfully incorporated into a solid matrix with high drug loading and improved stability compared to prodrug alone. PMID:24047113

TRO40303 Ameliorates Alcohol-Induced Pancreatitis Through Reduction of Fatty Acid Ethyl Ester–Induced Mitochondrial Injury and Necrotic Cell Death

PubMed Central

Javed, Muhammad Ahsan; Wen, Li; Awais, Muhammad; Latawiec, Diane; Huang, Wei; Chvanov, Michael; Schaller, Sophie; Bordet, Thierry; Michaud, Magali; Pruss, Rebecca; Tepikin, Alexei; Criddle, David; Sutton, Robert

2018-01-01

Objectives Mitochondrial permeability transition pore inhibition is a promising approach to treat acute pancreatitis (AP). We sought to determine (i) the effects of the mitochondrial permeability transition pore inhibitor 3,5-seco-4-nor-cholestan-5-one oxime-3-ol (TRO40303) on murine and human pancreatic acinar cell (PAC) injury induced by fatty acid ethyl esters (FAEEs) or taurolithocholic acid-3-sulfate and (ii) TRO40303 pharmacokinetics and efficacy in experimental alcoholic AP (FAEE-AP). Methods Changes in mitochondrial membrane potential (Δψm), cytosolic Ca2+ ([Ca2+]c), and cell fate were examined in freshly isolated murine or human PACs by confocal microscopy. TRO40303 pharmacokinetics were assessed in cerulein-induced AP and therapeutic efficacy in FAEE-AP induced with palmitoleic acid and ethanol. Severity of AP was assessed by standard biomarkers and blinded histopathology. Results TRO40303 prevented loss of Δψm and necrosis induced by 100 μM palmitoleic acid ethyl ester or 500 μM taurolithocholic acid-3-sulfate in murine and human PACs. Pharmacokinetic analysis found TRO40303 accumulated in the pancreas. A single dose of 3 mg/kg TRO40303 significantly reduced serum amylase (P = 0.043), pancreatic trypsin (P = 0.018), and histopathology scores (P = 0.0058) in FAEE-AP. Conclusions TRO40303 protects mitochondria and prevents necrotic cell death pathway activation in murine and human PACs, ameliorates the severity of FAEE-AP, and is a candidate drug for human AP. PMID:29200128

Assessment of chemical and sensory quality of sugarcane alcoholic fermented beverage.

PubMed

Resende Oliveira, Érica; Caliari, Márcio; Soares Soares Júnior, Manoel; Ribeiro Oliveira, Aryane; Cristina Marques Duarte, Renata; Valério de Barros Vilas Boas, Eduardo

2018-01-01

This study aimed to verify the technological feasibility, chemical quality and sensory acceptance of alcoholic fermented beverage obtained from sugarcane juice. A completely randomized design was applied. Sugar and alcohol content, phenolic (HPLC-MS) and volatile (GS-MS) compounds, pH, density, dry matter and acidity of the fermented beverage of sugarcane were quantified, as well as the acceptance of the product was carried out. The complete fermentation of sugarcane lasted 7 days, and it was obtained an alcohol content of 8.0% v/v. Titrable acidity of the beverage was of 67.31 meq L -1 , pH 4.03, soluble solids of 5 °Brix, reducing sugar of 0.07 g glucose 100 g -1 , density of 0.991 g cm -3 , reduced dry matter of 14.15 g L -1 , sulfates lower than 0.7 g K 2 SO 4  L -1 . Various phenolic compounds, among which, gallic acid (10.97%), catechin (1.73%), chlorogenic acid (3.52%), caffeic acid (1.49%), vanillic acid (0.28%), p -coumaric acid (0.24%), ferulic acid (6.63%), m -coumaric acid (0.36%), and o -coumaric acid (0.04%). Amongst aromatic compounds, were found mainly esters with fruity aromas (ethyl ester hexanoic acid and ethyl ester octanoic acid). The sugarcane juice can be commercialized as an alternative wine, as it presented adequate features to an alcoholic fermented beverage and was sensory accepted by consumers.

Omega-3 fatty acids promote fatty acid utilization and production of pro-resolving lipid mediators in alternatively activated adipose tissue macrophages.

PubMed

Rombaldova, Martina; Janovska, Petra; Kopecky, Jan; Kuda, Ondrej

2017-08-26

It is becoming increasingly apparent that mutual interactions between adipocytes and immune cells are key to the integrated control of adipose tissue inflammation and lipid metabolism in obesity, but little is known about the non-inflammatory functions of adipose tissue macrophages (ATMs) and how they might be impacted by neighboring adipocytes. In the current study we used metabolipidomic analysis to examine the adaptations to lipid overload of M1 or M2 polarized macrophages co-incubated with adipocytes and explored potential benefits of omega-3 polyunsaturated fatty acids (PUFA). Macrophages adjust their metabolism to process excess lipids and M2 macrophages in turn modulate lipolysis and fatty acids (FA) re-esterification of adipocytes. While M1 macrophages tend to store surplus FA as triacylglycerols and cholesteryl esters in lipid droplets, M2 macrophages channel FA toward re-esterification and β-oxidation. Dietary omega-3 PUFA enhance β-oxidation in both M1 and M2. Our data document that ATMs contribute to lipid trafficking in adipose tissue and that omega-3 PUFA could modulate FA metabolism of ATMs. Copyright © 2017 Elsevier Inc. All rights reserved.

Cytochrome c oxidase inhibition in the rice weevil Sitophilus oryzae (L.) by formate, the toxic metabolite of volatile alkyl formates.

PubMed

Haritos, V S; Dojchinov, G

2003-10-01

Volatile alkyl formates are potential replacements for the ozone-depleting fumigant, methyl bromide, as postharvest insecticides and here we have investigated their mode of insecticidal action. Firstly, a range of alkyl esters, ethanol and formic acid were tested in mortality bioassays with adults of the rice weevil, Sitophilus oryzae (L.) and the grain borer, Rhyzopertha dominica (F.) to determine whether the intact ester or one of its components was the toxic moiety. Volatile alkyl formates and formic acid caused similar levels of mortality (LC(50) 131-165 micromol l(-1)) to S. oryzae and were more potent than non-formate containing alkyl esters and ethanol (LC(50)>275 micromol l(-1)). The order of potency was the same in R. dominica. Ethyl formate was rapidly metabolised in vitro to formic acid when incubated with insect homogenates, presumably through the action of esterases. S. oryzae and R. dominica fumigated with a lethal dose of ethyl formate had eight and 17-fold higher concentrations of formic acid, respectively, in their bodies than untreated controls. When tested against isolated mitochondria from S. oryzae, alkyl esters, alcohols, acetate and propionate salts were not inhibitory towards cytochrome c oxidase (EC 1.9.3.1), but sodium cyanide and sodium formate were inhibitory with IC(50) values of 0.0015 mM and 59 mM, respectively. Volatile formate esters were more toxic than other alkyl esters, and this was found to be due, at least in part, to their hydrolysis to formic acid and its inhibition of cytochrome c oxidase.

Transition-Metal-Free Synthesis of 1,3-Butadiene-Containing π-Conjugated Polymers.

PubMed

Cai, Xuediao; Liu, Yating; Lu, Tian; Yang, Rui; Luo, Chuxin; Zhang, Qi; Chai, Yonghai

2016-12-01

This work describes the synthesis of π-conjugated polymers possessing arylene and 1,3-butadiene alternating units in the main chain by the reaction of α,β-unsaturated ester/nitrile containing γ-H with aromatic/heteroaromatic aldehyde compound. By using 4-(4-formylphenyl)-2-butylene acid ethyl ester as a model monomer, the different polymerization conditions, including catalyst, catalyst amount, and solvent, are optimized. The polymerization of 4-(4-formylphenyl)-2-butylene acid ethyl ester is carried out by refluxing in ethanol for 72 h with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst to give a 1,3-butadiene-containing π-conjugated polymer, poly(phenylene-1,3-butadiene), in 84.3% yield with M¯n and M¯w/M¯n (PDI) estimated as 6172 and 1.65, respectively. Based on this new methodology, a series of π-conjugated polymers containing 1,3-butadiene units with different substituents are obtained in high yields. A possible mechanism is proposed for the polymerization through a six-membered ring transition state and then a 1,5-H shift intermediate. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Do fatty acids help in overcoming reading difficulties? A double-blind, placebo-controlled study of the effects of eicosapentaenoic acid and carnosine supplementation on children with dyslexia.

PubMed

Kairaluoma, L; Närhi, V; Ahonen, T; Westerholm, J; Aro, M

2009-01-01

There are claims that dietary supplementation of unsaturated fatty acids could help children with dyslexia to overcome their reading problems. However, these claims have not yet been empirically tested. This study was designed to test whether dietary supplementation was superior to placebo in treating reading, spelling or other reading-related skills of children with dyslexia. The experimental group (eicosapentaenoic acid, EPA, n = 30) ate dietary supplements and the control group (placebo, n = 31) placebos during the 90-day treatment period. The supplements contained omega-3 fatty acid (ethyl-EPA, 500 mg/day) and carnosine (400 mg/day). The groups were matched for reading skills, grade, gender, attention problems, intelligence and amount of special education. The literacy-related skills of the two groups were assessed before and after the treatment period. No group differences were observed between EPA and placebo in measures of reading accuracy or speed, spelling, decoding fluency, arithmetical skills, reading-related language skills, attention or behavioural problems. The present findings do not support the hypothesis that omega-3 fatty acid (ethyl-EPA) or carnosine has a role in the treatment of reading and spelling problems in children with dyslexia.

Quantitative analysis of fatty-acid-based biofuels produced by wild-type and genetically engineered cyanobacteria by gas chromatography-mass spectrometry.

PubMed

Guan, Wenna; Zhao, Hui; Lu, Xuefeng; Wang, Cong; Yang, Menglong; Bai, Fali

2011-11-11

Simple and rapid quantitative determination of fatty-acid-based biofuels is greatly important for the study of genetic engineering progress for biofuels production by microalgae. Ideal biofuels produced from biological systems should be chemically similar to petroleum, like fatty-acid-based molecules including free fatty acids, fatty acid methyl esters, fatty acid ethyl esters, fatty alcohols and fatty alkanes. This study founded a gas chromatography-mass spectrometry (GC-MS) method for simultaneous quantification of seven free fatty acids, nine fatty acid methyl esters, five fatty acid ethyl esters, five fatty alcohols and three fatty alkanes produced by wild-type Synechocystis PCC 6803 and its genetically engineered strain. Data obtained from GC-MS analyses were quantified using internal standard peak area comparisons. The linearity, limit of detection (LOD) and precision (RSD) of the method were evaluated. The results demonstrated that fatty-acid-based biofuels can be directly determined by GC-MS without derivation. Therefore, rapid and reliable quantitative analysis of fatty-acid-based biofuels produced by wild-type and genetically engineered cyanobacteria can be achieved using the GC-MS method founded in this work. Copyright © 2011 Elsevier B.V. All rights reserved.

Polyphosphazene/Nano-Hydroxyapatite Composite Microsphere Scaffolds for Bone Tissue Engineering

PubMed Central

Nukavarapu, Syam P.; Kumbar, Sangamesh G.; Brown, Justin L.; Krogman, Nicholas R.; Weikel, Arlin L.; Hindenlang, Mark D.; Nair, Lakshmi S.; Allcock, Harry R; Laurencin, Cato T.

2009-01-01

The non-toxic, neutral degradation products of amino acid ester polyphosphazenes make them ideal candidates for in vivo orthopaedic applications. The quest for new osteocompatible materials for load bearing tissue engineering applications has led us to investigate mechanically competent amino acid ester substituted polyphosphazenes. In this study, we have synthesized three biodegradable polyphosphazenes substituted with side groups namely leucine, valine and phenylalanine ethyl esters. Of these polymers, the phenylalanine ethyl ester substituted polyphosphazene showed the highest glass transition temperature (41.6 °C) and hence was chosen as a candidate material for forming composite microspheres with 100 nm sized hydroxyapatite (nHAp). The fabricated composite microspheres were sintered into a three-dimensional (3-D) porous scaffold by adopting a dynamic solvent sintering approach. The composite microsphere scaffolds showed compressive moduli of 46–81 MPa with mean pore diameters in the range of 86–145 µm. The three-dimensional polyphosphazene-nHAp composite microsphere scaffolds showed good osteoblast cell adhesion, proliferation and alkaline phosphatase expression, and are potential suitors for bone tissue engineering applications. PMID:18517248

Catalyst-free ethyl biodiesel production from rice bran under subcritical condition

NASA Astrophysics Data System (ADS)

Zullaikah, Siti; Afifudin, Riza; Amalia, Rizky

2015-12-01

In-situ ethyl biodiesel production from rice bran under subcritical water and ethanol with no catalyst was employed. This process is environmentally friendly and is very flexible in term of feedstock utilization since it can handle relatively high moisture and free fatty acids (FFAs) contents. In addition, the alcohol, i.e. bioethanol, is a non-toxic, biodegradable, and green raw material when produced from non-edible biomass residues, leading to a 100% renewable biodiesel. The fatty acid ethyl esters (FAEEs, ethyl biodiesel) are better than fatty acid methyl esters (FAMEs, methyl biodiesel) in terms of fuel properties, including cetane number, oxidation stability and cold flow properties. The influences of the operating variables such as reaction time (1 - 10 h), ethanol concentration (12.5 - 87.5%), and pressurizing gas (N2 and CO2) on the ethyl biodiesel yield and purity have been investigated systematically while the temperature and pressure were kept constant at 200 °C and 40 bar. The optimum results were obtained at 5 h reaction time and 75% ethanol concentration using CO2 as compressing gas. Ethyl biodiesel yield and purity of 58.78% and 61.35%, respectively, were obtained using rice bran with initial FFAs content of 37.64%. FFAs level was reduced to 14.22% with crude ethyl biodiesel recovery of 95.98%. Increasing the reaction time up to 10 h only increased the yield and purity by only about 3%. Under N2 atmosphere and at the same operating conditions (5h and 75% ethanol), ethyl biodiesel yield and purity decreased to 54.63% and 58.07%, respectively, while FFAs level was increased to 17.93% and crude ethyl biodiesel recovery decreased to 87.32%.

Greening Wittig Reactions: Solvent-Free Synthesis of Ethyl Trans-Cinnamate and Trans-3-(9-Anthryl)-2-Propenoic Acid Ethyl Ester

ERIC Educational Resources Information Center

Nguyen, Kim Chi; Weizman, Haim

2007-01-01

Green procedure is used to create solvent-free alternatives for conventional Wittig reactions, which are widely used to install a double bond in a highly selective manner. Solvent-free reactions reduce health and environmental risks and provide a basis for an inquiry-based discussion of the stereochemistry of the Wittig reaction and the factors…

Semi-Preparative Separation of 10 Caffeoylquinic Acid Derivatives Using High Speed Counter-Current Chromatogaphy Combined with Semi-Preparative HPLC from the Roots of Burdock (Arctium lappa L.).

PubMed

Zheng, Zhenjia; Wang, Xiao; Liu, Pengli; Li, Meng; Dong, Hongjing; Qiao, Xuguang

2018-02-15

Burdock roots are healthy dietary supplements and a kind of famous traditional Chinese medicine, which contains large amounts of caffeoylquinic acid derivatives. However, little research has been reported on the preparative separation of these compounds from burdock roots. In the present study, a combinative method of HSCCC and semi-preparative HPLC was developed for the semi-preparative separation of caffeoylquinic acid derivatives from the burdock roots. The ethyl acetate extract of burdock roots was first fractionated by MCI macroporous resin chromatography and give three fractions (Fr. 1-3) from the elution of 40% methanol. Then, these three fractions (120 mg) were separately subjected to HSCCC for purification with the solvent system composed of petroleum ether-ethyl acetate-methanol-water at different volume ratios, and the mixtures were further purified by semi-preparative HPLC. As a result, a total of eight known caffeoylquinic acid derivatives including 3- O -caffeoylquinic acid (32.7 mg, 95.7%), 1,5- O - dicaffeoylquinic acid (4.3 mg, 97.2%), 3- O -caffeoylquinic acid methyl ester (12.1 mg, 93.2%), 1,3- O -dicaffeoylquinic acid (42.9 mg, 91.1%), 1,5- O -dicaffeoyl-3- O -(4-maloyl)-quinic acid (4.3 mg, 84.5%), 4,5- O -dicaffeoylquinic acid (5.3 mg, 95.5%), 1,5- O -dicaffeoyl-3- O -succinylquinic acid (8.7 mg, 93.4%), and 1,5- O -dicaffeoyl-4- O -succinylquinic acid (1.7 mg, 91.8%), and two new compounds were obtained. The new compounds were 1,4- O -dicaffeoyl-3-succinyl methyl ester quinic acid (14.6 mg, 96.1%) and 1,5- O -dicaffeoyl-3- O -succinyl methyl ester quinic acid (3.1 mg, 92.6%), respectively. The research indicated that the combination of HSCCC and semi-preparative HPLC is a highly efficient approach for preparative separation of the instability and bioactive caffeoylquinic acid derivatives from natural products.

S-Nitroso-N-acetyl-L-cysteine ethyl ester (SNACET) and N-acetyl-L-cysteine ethyl ester (NACET)-Cysteine-based drug candidates with unique pharmacological profiles for oral use as NO, H2S and GSH suppliers and as antioxidants: Results and overview.

PubMed

Tsikas, Dimitrios; Schwedhelm, Kathrin S; Surdacki, Andrzej; Giustarini, Daniela; Rossi, Ranieri; Kukoc-Modun, Lea; Kedia, George; Ückert, Stefan

2018-02-01

S -Nitrosothiols or thionitrites with the general formula RSNO are formally composed of the nitrosyl cation (NO + ) and a thiolate (RS - ), the base of the corresponding acids RSH. The smallest S -nitrosothiol is HSNO and derives from hydrogen sulfide (HSH, H 2 S). The most common physiological S -nitrosothiols are derived from the amino acid L-cysteine (CysSH). Thus, the simplest S -nitrosothiol is S -nitroso-L-cysteine (CysSNO). CysSNO is a spontaneous potent donor of nitric oxide (NO) which activates soluble guanylyl cyclase to form cyclic guanosine monophosphate (cGMP). This activation is associated with multiple biological actions that include relaxation of smooth muscle cells and inhibition of platelet aggregation. Like NO, CysSNO is a short-lived species and occurs physiologically at concentrations around 1 nM in human blood. CysSNO can be formed from CysSH and higher oxides of NO including nitrous acid (HONO) and its anhydride (N 2 O 3 ). The most characteristic feature of RSNO is the S-transnitrosation reaction by which the NO + group is reversibly transferred to another thiolate. By this way numerous RSNO can be formed such as the low-molecular-mass S -nitroso- N -acetyl-L-cysteine (SNAC) and S -nitroso-glutathione (GSNO), and the high-molecular-mass S -nitrosol-L-cysteine hemoglobin (HbCysSNO) present in erythrocytes and S -nitrosol-L-cysteine albumin (AlbCysSNO) present in plasma at concentrations of the order of 200 nM. All above mentioned RSNO exert NO-related biological activity, but they must be administered intravenously. This important drawback can be overcome by lipophilic charge-free RSNO. Thus, we prepared the ethyl ester of SNAC, the S -nitroso- N -acetyl-L-cysteine ethyl ester (SNACET), from synthetic N -acetyl-L-cysteine ethyl ester (NACET). Both NACET and SNACET have improved pharmacological features over N -acetyl-L-cysteine (NAC) and S -nitroso- N -acetyl-L-cysteine (SNAC), respectively, including higher oral bioavailability. SNACET exerts NO-related activities which can be utilized in the urogenital tract and in the cardiovascular system. NACET, with high oral bioavailability, is a strong antioxidant and abundant precursor of GSH, unlike its free acid N -acetyl-L-cysteine (NAC). Here, we review the chemical and pharmacological properties of SNACET and NACET as well as their analytical chemistry. We also report new results from the ingestion of S -[ 15 N]nitroso- N -acetyl-L-cysteine ethyl ester (S 15 NACET) demonstrating the favorable pharmacological profile of SNACET.

Rigid Dipeptide Mimics: Synthesis of Enantiopure 5- and 7-Benzyl and 5,7-Dibenzyl Indolizidinone Amino Acids via Enolization and Alkylation of delta-Oxo alpha,omega-Di-[N-(9-(9-phenylfluorenyl))amino]azelate Esters.

PubMed

Polyak, Felix; Lubell, William D.

1998-08-21

Azabicyclo[X.Y.0]alkane amino acids are tools for constructing mimics of peptide structure and templates for generating combinatorial libraries for drug discovery. Our methodology for synthesizing these conformationally rigid dipeptides has been elaborated such that alkyl groups can be appended onto the heterocycle to generate mimics of peptide backbone and side-chain structure. Inexpensive glutamic acid was employed as chiral educt in a Claisen condensation/ketone alkylation/reductive amination/lactam cyclization sequence that furnished alkyl-branched azabicyclo[4.3.0]alkane amino acid. Enantiopure 5-benzyl-, 7-benzyl-, and 5,7-dibenzylindolizidinone amino acids 2-4 were stereoselectively synthesized via efficient reaction sequences featuring the alkylation of di-tert-butyl alpha,omega-di-[N-(PhF)amino]azelate delta-ketone 5. A variety of alkyl halides were readily added to the enolate of ketone 5 to provide mono- and dialkylated ketones 6 and 7. Hydride additions to 6 and 7, methanesulfonations, and intramolecular S(N)2 displacements by the PhF amine gave 5-alkylprolines that were converted by lactam cyclizations into 7- and 5-benzyl-, as well as 5,7-dibenzyl-2-oxo-3-N-(BOC)amino-1-azabicyclo[4.3.0]nonane-9-carboxylate methyl esters 10, 11, and 14. Epimerization of the alkyl-branched stereocenter via an iminium-enaminium equilibrium proved effective for controlling diastereoselectivity in reductive aminations with 6 and 7 in order to furnish 5-alkylprolines that were similarly converted to 7- benzyl- and 5,7-dibenzylindolizidinone N-(BOC)amino esters 10 and 14. Ester hydrolysis with hydroxide ion and potassium trimethylsilanolate then gave enantiopure indolizidinone amino acids 2-4. Epimerization at C-9 of benzylindolizidinone amino esters was also used to provide alternative diastereomers of 10, 11, and 14. This practical methodology for introducing side-chain groups onto the heterocycle with regioselective and diastereoselective control is designed to enhance the use of alkyl-branched azabicycloalkane amino acids for the exploration of conformation-activity relationships of various biologically active peptides.

Chemical constituents from Tillandsia recurvata.

PubMed

de Queiroga, Marcos Aurélio; de Andrade, Lucimara Mariano; Florêncio, Karina Chagas; de Fátima Agra, Maria; da Silva, Marcelo Sobral; Barbosa-Filho, José Maria; da-Cunha, Emidio Vasconcelos Leitão

2004-06-01

The CHCl3 extract of Tillandsia recurvata yielded 5,3'-dihydroxy-6,7,8,4'-tetramethoxyflavanone (1), 1,3-di-O-cinnamoyl-glycerol (2) and ethyl ester of caffeic acid. Their structures were elucidated by means of spectroscopic methods such as mass spectroscopy and 1 and 2D-NMR. Copyright 2004 Elsevier B.V.

Adjunctive Nutraceuticals for Depression: A Systematic Review and Meta-Analyses.

PubMed

Sarris, Jerome; Murphy, Jenifer; Mischoulon, David; Papakostas, George I; Fava, Maurizio; Berk, Michael; Ng, Chee H

2016-06-01

There is burgeoning interest in augmentation strategies for improving inadequate response to antidepressants. The adjunctive use of standardized pharmaceutical-grade nutrients, known as nutraceuticals, has the potential to modulate several neurochemical pathways implicated in depression. While many studies have been conducted in this area, to date no specialized systematic review (or meta-analysis) has been conducted. A systematic search of PubMed, CINAHL, Cochrane Library, and Web of Science was conducted up to December 2015 for clinical trials using adjunctive nutrients for depression. Where sufficient data were available, a random-effects model analyzed the standard mean difference between treatment and placebo in the change from baseline to endpoint, combining the effect size data. Funnel plot and heterogeneity analyses were also performed. Primarily positive results were found for replicated studies testing S-adenosylmethionine (SAMe), methylfolate, omega-3 (primarily EPA or ethyl-EPA), and vitamin D, with positive isolated studies for creatine, folinic acid, and an amino acid combination. Mixed results were found for zinc, folic acid, vitamin C, and tryptophan, with nonsignificant results for inositol. No major adverse effects were noted in the studies (aside from minor digestive disturbance). A meta-analysis of adjunctive omega-3 versus placebo revealed a significant and moderate to strong effect in favor of omega-3. Conversely, a meta-analysis of folic acid revealed a nonsignificant difference from placebo. Marked study heterogeneity was found in a Higgins test for both omega-3 and folic acid studies; funnel plots also revealed asymmetry (reflecting potential study bias). Current evidence supports adjunctive use of SAMe, methylfolate, omega-3, and vitamin D with antidepressants to reduce depressive symptoms.

Metabolic pathway engineering for fatty acid ethyl ester production in Saccharomyces cerevisiae using stable chromosomal integration.

PubMed

de Jong, Bouke Wim; Shi, Shuobo; Valle-Rodríguez, Juan Octavio; Siewers, Verena; Nielsen, Jens

2015-03-01

Fatty acid ethyl esters are fatty acid derived molecules similar to first generation biodiesel (fatty acid methyl esters; FAMEs) which can be produced in a microbial cell factory. Saccharomyces cerevisiae is a suitable candidate for microbial large scale and long term cultivations, which is the typical industrial production setting for biofuels. It is crucial to conserve the metabolic design of the cell factory during industrial cultivation conditions that require extensive propagation. Genetic modifications therefore have to be introduced in a stable manner. Here, several metabolic engineering strategies for improved production of fatty acid ethyl esters in S. cerevisiae were combined and the genes were stably expressed from the organisms' chromosomes. A wax ester synthase (ws2) was expressed in different yeast strains with an engineered acetyl-CoA and fatty acid metabolism. Thus, we compared expression of ws2 with and without overexpression of alcohol dehydrogenase (ADH2), acetaldehyde dehydrogenase (ALD6) and acetyl-CoA synthetase (acs SE (L641P) ) and further evaluated additional overexpression of a mutant version of acetyl-CoA decarboxylase (ACC1 (S1157A,S659A) ) and the acyl-CoA binding protein (ACB1). The combined engineering efforts of the implementation of ws2, ADH2, ALD6 and acs SE (L641P) , ACC1 (S1157A,S659A) and ACB1 in a S. cerevisiae strain lacking storage lipid formation (are1Δ, are2Δ, dga1Δ and lro1Δ) and β-oxidation (pox1Δ) resulted in a 4.1-fold improvement compared with sole expression of ws2 in S. cerevisiae.

Studies of the acidic components of the Colorado Green River formation oil shale-Mass spectrometric identification of the methyl esters of extractable acids.

NASA Technical Reports Server (NTRS)

Haug, P.; Schnoes, H. K.; Burlingame, A. L.

1971-01-01

Study of solvent extractable acidic constituents of oil shale from the Colorado Green River Formation. Identification of individual components is based on gas chromatographic and mass spectrometric data obtained for their respective methyl esters. Normal acids, isoprenoidal acids, alpha, omega-dicarboxylic acids, mono-alpha-methyl dicarboxylic acids and methyl ketoacids were identified. In addition, the presence of monocyclic, benzoic, phenylalkanoic and naphthyl-carboxylic acids, as well as cycloaromatic acids, is demonstrated by partial identification.

Antioxidant efficacy of feruloyl glycerols in model membranes

USDA-ARS?s Scientific Manuscript database

Ferulic acid and its esters are known to be effective antioxidants. Ethyl ferulate was biocatalytically transesterified with triacylglycerols and long chain alcohols to form a series of lipid-based feruloyl esters: feruloylglycerol, diferuloylglycerol, feruloyldiacylglycerol, diferuloylacylglycerol...

Extraction and identification of bioactive components in Sida cordata (Burm.f.) using gas chromatography-mass spectrometry.

PubMed

Ganesh, Mani; Mohankumar, Murugan

2017-09-01

Sida cordata (Burm.f.) is a pineal tropical plant in the family Malvaceae that is found throughout India and used to treat various diseases and ailments in many complementary and alternative medicine systems. This study identified the bioactive components present in whole-plant ethanol extracts of S . cordata using gas chromatography-mass spectrometry (GC-MS). Based on their retention times (RT) and mass-to-charge ratios (m/z), 29 bioactive compounds were identified: nonanoic acid, vitamin D 3 , 3-trifluroacetoxypentadecane, α-d-glucopyranoside, O-α-d-glucopyranosyl-(1.fwdarw.3)-α-d-fructofuranosyl,3,7,11,15-tetramethyl-2-hexadecan-1-ol, octadecanoic acid, ethyl ester, phytol, 9,12-octadecadienoic acid, methyl ester (E,E), 9,12,15-octadecadienoic acid, methyl ester (Z,Z,Z), oleic acid, 1,2-15,16-diepoxyhexadecane, 3-hexadecyloxycarbonyl-5-(2-hydroxyethyl)-4-methylimidazolium ion, methoxyacetic acid, 4-tetradecyl ester, 1,2-benzenedicarboxylic acid, mono (2-ethylhexyl) ester, 1-iodo-2-methylundecane, dodecane, 2,6,10-trimethyl-, 2-piperidinone-N-[4-bromo-n-butyl]-, squalene, octadecane-1-(ethenyloxy)-, Z,Z-2,5-pentadecadien-1-ol, 1-hexadecanol, 2-methyl-, spiro[androst-5ene-17,1'-cyclobutan]-2'-one-3-hydroxy-, (3a,17a)-, diethylene glycol monododecyl ether, vitamin E, cholestan-3-ol, 2-methylene-, (3a,5a)-, 2H-pyran, 2-(7-heptadecynyloxy)tetrahydro-, and cis -Z-α-bisabolene epoxide. The presence of various bioactive compounds justifies the use of this plant for treating various ailments by traditional practitioners.

Experimental and theoretical studies of the molecular structure of 7-Methyl-3-[(3-methyl-3-mesityl-cyclobutyl]-5-phenyl-5H-thiazolo[3,2-α]pyrimidine-6-carboxylic acid ethyl ester

NASA Astrophysics Data System (ADS)

Acar, Betül; Yilmaz, Ibrahim; Çalışkan, Nezihe; Cukurovali, Alaaddin

2017-07-01

In this work, the title molecule, 7-Methyl-3-[(3-methyl-3-mesityl-cyclobutyl]-5-phenyl-5H-thiazolo[3,2-α]pyrimidine-6-carboxylic acid ethyl ester (C30H34N2O2S1), was synthesized and characterized by FT-IR spectroscopy and single crystal X-ray diffraction. The compound crystallizes in the triclinic space group P21/c. with Z = 4, a = 14.1988(6), b = 19.0893(5), c = 10.1325(4) Å, V = 2674.56(17) A3. The optimized structure parameters of the studied molecule was determined theoretically using HF/6-31G(d) and B3LYP/6-31G(d) methods for ground state, and compared with previously reported experimental findings. The calculated harmonic vibrational frequencies are scaled and they are compared with experimental frequencies obtained by FT-IR spectra. The electronic properties, such as HOMO and LUMO energies, and molecular electrostatic potential (MEP) are also performed.

A new, direct analytical method using LC-MS/MS for fatty acid esters of 3-chloro-1,2-propanediol (3-MCPD esters) in edible oils.

PubMed

Yamazaki, K; Ogiso, M; Isagawa, S; Urushiyama, T; Ukena, T; Kibune, N

2013-01-01

A new, direct analytical method for the determination of 3-chloro-1,2-propanediol fatty acid esters (3-MCPD esters) was developed. The targeted 3-MCPD esters included five types of monoester and 25 [corrected] types of diester. Samples (oils and fats) were dissolved in a mixture of tert-butyl methyl ether and ethyl acetate (4:1), purified using two solid-phase extraction (SPE) cartridges (C(18) and silica), then analysed by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Five monoesters and five diesters with the same fatty acid group could be separated and quantified. Pairs of 3-MCPD diesters carrying the same two different fatty acid groups, but at reversed positions (sn-1 and sn-2), could not be separated and so were expressed as a sum of both compounds. The limits of quantification (LOQs) were estimated to be between 0.02 to 0.08 mg kg(-1), depending on the types of 3-MCPD ester. Repeatability expressed as relative standard deviation (RSD(r)%) varied from 5.5% to 25.5%. The new method was shown to be applicable to various commercial edible oils and showed levels of 3-MCPD esters varying from 0.58 to 25.35 mg kg(-1). The levels of mono- and diesters ranged from 0.10 to 0.69 mg kg(-1) and from 0.06 to 16 mg kg(-1), respectively.

Gas-Phase Amidation of Carboxylic Acids with Woodward’s Reagent K Ions

PubMed Central

Peng, Zhou; Pilo, Alice L.; Luongo, Carl A.; McLuckey, Scott A.

2015-01-01

Gas-phase amidation of carboxylic acids in multiply-charged peptides is demonstrated via ion/ion reactions with Woodward’s reagent K (wrk) in both positive and negative mode. Woodward’s reagent K, N-ethyl-3-phenylisoxazolium-3′-sulfonate, is a commonly used reagent that activates carboxylates to form amide bonds with amines in solution. Here, we demonstrate that the analogous gas-phase chemistry occurs upon reaction of the wrk ions and doubly protonated (or doubly deprotonated) peptide ions containing the carboxylic acid functionality. The reaction involves the formation of the enol ester intermediate in the electrostatic complex. Upon collisional activation, the ethyl amine on the reagent is transferred to the activated carbonyl carbon on the peptide, resulting in the formation of an ethyl amide (addition of 27 Da to the peptide) with loss of a neutral ketene derivative. Further collision-induced dissociation (CID) of the products and comparison with solution-phase amidation product confirms the structure of the ethyl amide. PMID:26122523

Synthesis and molecular crystal of 3-Chloro-2-(1-chloro-1-methyl-ethyl)-2,3-dihydro-1H-naphtho[2,1-b]oxepin-4-one

NASA Astrophysics Data System (ADS)

Tittal, Ram Kumar

2018-03-01

CuCl/TMEDA-promoted halogen atom transfer radical cyclization (HATRC) of dichloroacetic acid 1-(3-methyl-but-2-enyl)-naphthalen-2-yl ester in refluxing DCE gave chlorine containing 7-member lactone 3-Chloro-2-(1-chloro-1-methyl-ethyl)-2,3-dihydro-1H-naphtho[2,1-b]oxepin-4-one via 7-exo trig radical cyclization reaction. The structure of the Lactone was confirmed by X-ray diffraction data.

[Dietary supplementation of obese children with 1000 mg alpha-linolenic acid per day: a placebo-controlled double blind study].

PubMed

Lohner, Szimonetta; Marosvölgyi, Tamás; Burus, István; Schmidt, János; Molnár, Dénes; Decsi, Tamás

2007-08-12

Enhanced dietary intake of omega-3 fatty acids may benefit persons with increased cardiovascular risk, among them obese subjects. Incorporation of omega-3 fatty acids into the plasma lipids is a prerequisite to achieve the favorable effects; however, only very few data are available on the dose of omega-3 fatty acid supplementation in children. The aim of our study was to examine the effects of the consumption of a diet supplemented with 1000 mg alpha-linolenic acid daily on plasma lipids in obese children. In this two times six-week-long, placebo-controlled, crossover study, 9 obese children (age: 13.1 [2.5] years, body mass index: 31.2 [6.2] kg/m 2 ), median [IQR]) incorporated into their diet one egg and one meatball (50 g) per day from hens fed diets containing flaxseed oil, i.e. supplementary dietary intake of 1000 mg alpha-linolenic acid per day was provided. The fatty acid composition of plasma lipids was determined by high-resolution gas-liquid chromatography. Tendencies of increase were observed in the alpha-linolenic acid content of plasma lipids in the phospholipid, triacyl-glycerine and sterol-ester fractions after the supplementation with alpha-linolenic acid. In the non-esterified fatty acid fraction, the values of alpha-linolenic acid were significantly higher after the supplementation (0.11 [0.08] versus 0.14 [0.20], % weight/weight, p < 0.05), indicating the beginning of the accumulation of alpha-linolenic acid in plasma lipids. In obese children a six-week-long supplementation of the diet with 1000 mg alpha-linolenic acid per day increased significantly the contribution of omega-3 fatty acids only to the non-esterified fatty acids of plasma lipids, but had no significant effect on the esterified fractions. Increase of the dose of supplementation may be needed to influence omega-3 fatty acid status in obese children.

Phenolic and Aroma Composition of White Wines Produced by Prolonged Maceration and Maturation in Wooden Barrels

PubMed Central

Jedrejčić, Nikolina; Ganić, Karin Kovačević; Staver, Mario; Peršurić, Đordano

2015-01-01

Summary To investigate the phenolic and aroma composition of Malvazija istarska (Vitis vinifera L.) white wines produced by an unconventional technology comprising prolonged maceration followed by maturation in wooden barrels, representative samples were subjected to analysis by UV/Vis spectrometry, high-performance liquid chromatography, and gas chromatography-mass spectrometry. When compared to standard wines, the investigated samples contained higher levels of dry extract, volatile acidity, lactic acid, phenols, colour intensity, antioxidant activity, majority of monoterpenes, C13-norisoprenoids, methanol, higher alcohols, ethyl acetate, branched-chain esters and esters of hydroxy and dicarboxylic acids, ethylphenols, furans, and acetals, as well as lower levels of malic acid, β-damascenone, straight-chain fatty acids, ethyl and acetate esters. It was estimated that maceration had a stronger influence on phenols, and maturation on volatile aromas. Despite different vintages and technological details, the investigated wines showed a relative homogeneity in the composition, representing a clear and distinctive type. PMID:27904375

Adsorption of acetanilide herbicides on soil and its components. II. Adsorption and catalytic hydrolysis of diethatyl-ethyl on saturated Na(+)-, K(+)-, Ca(2+)-, and Mg(2+)-montmorillonite.

PubMed

Liu, W P; Fang, Z; Liu, H J; Yang, W C

2001-04-01

Adsorption and catalytic hydrolysis of the herbicide diethatyl-ethyl [N-chloroacetyl-N-(2,6-diethylphenyl)glycine ethyl ester] on homoionic Na(+)-, K(+)-, Ca(2+)-, and Mg(2+)-montmorillonite clays were investigated in water solution. The Freundlich adsorption coefficient, Ki, got from isotherms on clay followed the order of Na+ approximately K+ > Mg2+ approximately Ca2+. Analysis of FT-IR spectra of diethatyl-ethyl adsorbed on clay suggests probable bonding at the carboxyl and amide carbonyl groups of the herbicide. The rate of herbicide hydrolysis in homoionic clay suspensions followed the same order as that for adsorption, indicating that adsorption may have preceded and thus caused hydrolysis. Preliminary product identification showed that hydrolysis occurred via nucleophilic substitution at the carboxyl carbon, causing the cleavage of the ester bond and formation of diethatyl and its dechlorinated derivative, and at the amide carbon, yielding an ethyl ester derivative and its acid. These pathways also suggest that hydrolysis of diethatyl-ethyl was catalyzed by adsorption on the clay surface.

Synthesis and biological evaluation of amino acid methyl ester conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid against the production of nitric oxide (NO).

PubMed

Onyango, Evans O; Fu, Liangfeng; Cao, Martine; Liby, Karen T; Sporn, Michael B; Gribble, Gordon W

2014-01-15

2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO, 2) was condensed with various amino acid methyl esters at the C-28 carboxylic acid. The new amide conjugates were evaluated for their inhibition of nitric oxide (NO) production in RAW264.7 cells stimulated with interferon-γ (IFNγ). Of these new compounds, CDDO conjugates with alanine, valine, and serine are nearly equipotent to CDDO-ethyl amide (4), a triterpenoid with promising biological activity in numerous disease models. Some of these conjugates also induce the in vitro expression of heme oxygenase-1, and inhibit the proliferation of Panc-1343 pancreatic cells. Copyright © 2013 Elsevier Ltd. All rights reserved.

Wax Ester Rich Oil From The Marine Crustacean, Calanus finmarchicus, is a Bioavailable Source of EPA and DHA for Human Consumption.

PubMed

Cook, Chad M; Larsen, Terje S; Derrig, Linda D; Kelly, Kathleen M; Tande, Kurt S

2016-10-01

Oil from the marine copepod, Calanus finmarchicus, which contains >86 % of fatty acids present as wax esters, is a novel source of n-3 fatty acids for human consumption. In a randomized, two-period crossover study, 18 healthy adults consumed 8 capsules providing 4 g of Calanus(®) Oil supplying a total of 260 mg EPA and 156 mg DHA primarily as wax esters, or 1 capsule of Lovaza(®) providing 465 mg EPA and 375 mg DHA as ethyl esters, each with an EPA- and DHA-free breakfast. Plasma EPA and DHA were measured over a 72 h period (t = 1, 2, 4, 6, 8, 10, 12, 24, 48, and 72 h). The positive incremental area under the curve over the 72 h test period (iAUC0-72 h) for both EPA and DHA was significantly different from zero (p < 0.0001) in both test conditions, with similar findings for the iAUC0-24 h and iAUC0-48 h, indicating the fatty acids were absorbed. There was no difference in the plasma iAUC0-72 h for EPA + DHA, or DHA individually, in response to Calanus Oil vs the ethyl ester condition; however, the iAUC0-48 h and iAUC0-72 h for plasma EPA in response to Calanus Oil were both significantly increased relative to the ethyl ester condition (iAUC0-48 h: 381 ± 31 vs 259 ± 39 μg*h/mL, p = 0.026; iAUC0-72 h: 514 ± 47 vs 313 ± 49 μg*h/mL, p = 0.009). These data demonstrate a novel wax ester rich marine oil is a suitable alternative source of EPA and DHA for human consumption.

Quantification of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in meconium for detection of alcohol abuse during pregnancy: Correlation study between both biomarkers.

PubMed

Cabarcos, Pamela; Tabernero, María Jesús; Otero, José Luís; Míguez, Martha; Bermejo, Ana María; Martello, Simona; De Giovanni, Nadia; Chiarotti, Marcello

2014-11-01

This article presents results from 47 meconium samples, which were analyzed for fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) for detection of gestational alcohol consumption. A validated microwave assisted extraction (MAE) method in combination with GC-MS developed in the Institute of Forensic Science (Santiago de Compostela) was used for FAEE and the cumulative concentration of ethyl myristate, ethyl palmitate and ethyl stearate with a cut-off of 600ng/g was applied for interpretation. A simple method for identification and quantification of EtG has been evaluated by ultrasonication followed solid phase extraction (SPE). Successful validation parameters were obtained for both biochemical markers of alcohol intake. FAEE and EtG concentrations in meconium ranged between values lower than LOD and 32,892ng/g or 218ng/g respectively. We have analyzed FAEE and EtG in the same meconium aliquot, enabling comparison of the efficiency of gestational ethanol exposure detection. Certain agreement between the two biomarkers was found as they are both a very specific alcohol markers, making it a useful analysis for confirmation. Copyright © 2014 Elsevier B.V. All rights reserved.

Lipase-Produced Hydroxytyrosyl Eicosapentaenoate is an Excellent Antioxidant for the Stabilization of Omega-3 Bulk Oils, Emulsions and Microcapsules.

PubMed

Akanbi, Taiwo Olusesan; Barrow, Colin James

2018-01-29

In this study, several lipophilic hydroxytyrosyl esters were prepared enzymatically using immobilized lipase from Candida antarctica B. Oxidation tests showed that these conjugates are excellent antioxidants in lipid-based matrices, with hydroxytyrosyl eicosapentaenoate showing the highest antioxidant activity. Hydroxytyrosyl eicosapentaenoate effectively stabilized bulk fish oil, fish-oil-in-water emulsions and microencapsulated fish oil. The stabilizing effect of this antioxidant may either be because it orients itself with the omega-3 fatty acids in the oil, thereby protecting them against oxidation, or because this unstable fatty acid can preferentially oxidise, thus providing an additional mechanism of antioxidant protection. Hydroxytyrosyl eicosapentaenoate itself was stable for one year when stored at -20 °C.

[Research of imidazo[1,2-a]benzimidazole derivatives. XXX. Synthesis and properties of (imidazo[1,2-a]benzimidazolyl-2)acetic acid derivatives].

PubMed

Anisimova, V A; Tolpygin, I E; Spasov, A A; Serdiuk, T S; Sukhov, A G

2011-01-01

Ethyl esters of (9-subtituted-imidazo[1,2-a]benzimidazolyl-2)acetic acids were synthesized. The chemical properties of these esters (hydrolysis, decarboxylation, hydrazinolysis) and biological activity (fungicidal, antimicrobial, antiarrhythmic activity, and also affects on the brain rhythmogenesis) of the prepared compounds were studied.

EFFECTS OF ANESTHESIA (MS222) ON LIVER BIOTRANSFORMATION IN RAINBOW TROUT (ONCORHYNCHUS MYKISS)

EPA Science Inventory

Tricaine methanesulfonate (3-aminobenzoic acid ethyl ester methanesulfonate; MS222) is a widely used fish anaesthetic. While there have been several studies addressing the impact of its use on subsequently measured biotransformation rates, the measured influence on normal functio...

Fatty acid ethyl esters (FAEE); comparative accumulation in human and guinea pig hair as a biomarker for prenatal alcohol exposure.

PubMed

Kulaga, Vivian; Caprara, Daniela; Iqbal, Umar; Kapur, Bhushan; Klein, Julia; Reynolds, James; Brien, James; Koren, Gideon

2006-01-01

To compare the incorporation rate (ICR) of fatty acid ethyl esters (FAEE) in hair between guinea pigs and humans, and to assess the relationship between ethanol exposure and FAEE concentrations in hair. Published data from pregnant guinea pigs, including maximum blood ethanol concentration (BEC), dosage regimen, and total hair FAEE concentration, were compared with published data from alcoholic patients, where dose of ethanol consumed and total hair FAEE concentration were reported. Mean values of ethanol Vmax for pregnant guinea pigs and humans were obtained from published data (26.2 and 24 mg/dl/h, respectively). Total and individual FAEE ICRs, defined as the ratio of hair FAEE to the area under the BEC-time curve (total systemic ethanol exposure), were found to be on average an order of magnitude lower in the guinea pig than in the human. The profiles of ester incorporation also differed slightly between species, with ethyl stearate being highly incorporated in guinea pig hair and less so in human hair. The results may reflect in the human greater FAEE production, greater FAEE deposition in hair, slower FAEE catabolism, differential sebum production and composition, or a combination thereof. Also, ethyl oleate was found to correlate with total systemic ethanol exposure for both guinea pigs and humans, correlation coefficients equalling 0.67 (P < 0.05) and 0.49 (P < 0.05), respectively. No other ethyl esters, nor total FAEE, were found to correlate with systemic ethanol exposure. When extrapolating FAEE concentrations in hair from guinea pigs to humans, an order of magnitude difference should be considered, with humans incorporating more FAEE per unit of ethanol exposure. Also, the results suggest caution should be taken when interpreting values of single esters because of their differential incorporation among species. Lastly, our findings suggest ethyl oleate may be of keen interest in FAEE hair analysis, particularly across species.

Effect of Hydrophobic Side Chains in the Induction of Immune Responses by Nanoparticle Adjuvants Consisting of Amphiphilic Poly(γ-glutamic acid).

PubMed

Shima, Fumiaki; Akagi, Takami; Akashi, Mitsuru

2015-05-20

The new generation vaccines are safe but poorly immunogenic, and thus they require the use of adjuvants. Adjuvants that can control the balance and induction level of cellular and humoral immunities are urgently required for the treatment of and/or protection from infectious diseases and cancers. However, there are no adjuvants which can achieve these requirements. In this study, amphiphilic poly(γ-glutamic acid) (γ-PGA) with various kinds of hydrophobic amino acid ethyl esters (AAE) was synthesized (γ-PGA-AAE) and used to prepare antigen-encapsulated nanoparticles (NPs). γ-PGA-graft-Leu (γ-PGA-Leu, where Leu = leucine ethyl ester), γ-PGA-graft-Phe (γ-PGA-Phe, where Phe = phenylalanine ethyl ester), and γ-PGA-graft-Trp (γ-PGA-Trp, where Trp = tryptophan ethyl ester) formed monodispersed NPs that encapsulated ovalbumin (OVA). The type and the induction level of the antigen-specific cellular and humoral immunities could be controlled by the kinds of hydrophobic segments and vaccine formulation (encapsulation or mixture) used. When OVA was encapsulated into NPs, the cellular immunity was dominantly induced, while humoral immunity was dominant when OVA was mixed with NPs. These results are a first report to demonstrate that the balance and induction level of cellular and humoral immunities could be controlled by modifying compositions of NPs and vaccine formulation. Our results suggest that γ-PGA-AAE NPs can provide safe and efficient nanoparticle-based vaccine adjuvants, and the results also provide guidelines in the rational design of amphiphilic polymers as vaccine adjuvants which can control the balance of immune responses.

Docosahexaenoic acid at the sn-2 position of structured triacylglycerols improved n-3 polyunsaturated fatty acid assimilation in tissues of hamsters.

PubMed

Bandarra, Narcisa M; Lopes, Paula A; Martins, Susana V; Ferreira, Júlia; Alfaia, Cristina M; Rolo, Eva A; Correia, Jorge J; Pinto, Rui M A; Ramos-Bueno, Rebeca P; Batista, Irineu; Prates, José A M; Guil-Guerrero, José L

2016-05-01

In this study, we hypothesized that the incorporation of docosahexaenoic acid (DHA) in tissues will be higher when it is ingested as triacylglycerols (TAG) structured at the sn-2 position, which enhances efficacy and health benefits of dietary DHA n-3 supplementation. Ten-week-old Golden Syrian male hamsters were randomly allocated into 4 dietary groups with 10 animals in each: linseed oil (LSO; control group), fish oil (FO), fish oil ethyl esters (FO-EE), and structured DHA at the sn-2 position of TAG (DHA-SL). After 12 weeks, there were no variations in the hamsters' body composition parameters across dietary groups. The DHA-SL diet had the lowest values of total cholesterol, low-density lipoprotein cholesterol, high-density lipoprotein cholesterol, total lipids, and aspartate aminotransferase activity, whereas the inverse was observed for the FO diet. Glucose was increased in the LSO diet without affecting insulin and insulin resistance markers. Whereas n-3 polyunsaturated fatty acid was increased in the brain of hamsters fed the DHA-SL diet, higher levels of n-6 polyunsaturated fatty acid were observed in the liver and erythrocytes of the LSO. The highest omega-3 index was obtained with the DHA-SL diet. The principal component analyses discriminated DHA from other metabolites and set apart 4 clusters matching the 4 diets. Similarly, liver, erythrocytes, and brain were separated from each other, pointing toward an individual signature on fatty acid deposition. The structured sn-2 position DHA-containing TAG ameliorated blood lipids and fatty acid incorporation, in particular eicosapentaenoic acid and DHA in liver, erythrocytes, and brain, relative to commercially FOs, thus improving the health benefits of DHA due to its higher bioavailability. Copyright © 2016 Elsevier Inc. All rights reserved.

Stereocontrolled reduction of alpha- and beta-keto esters with micro green algae, Chlorella strains.

PubMed

Ishihara, K; Yamaguchi, H; Adachi, N; Hamada, H; Nakajima, N

2000-10-01

The stereocontrolled reduction of alpha- and beta-keto esters using micro green algae was accomplished by a combination of the cultivation method and the introduction of an additive. The reduction of ethyl pyruvate and ethyl benzoylformate by the photoautotrophically cultivated Chlorella sorokiniana gave the corresponding alcohol in high e.e. (>99% e.e. (S) and >99% e.e. (R), respectively). In the presence of glucose as an additive, the reduction of ethyl 3-methyl-2-oxobutanoate by the heterotrophically cultivated C. sorokiniana afforded the corresponding (R)-alcohol. On the other hand, the reduction in the presence of ethyl propionate gave the (S)-alcohol. Ethyl 2-methyl-3-oxobutanoate was reduced in the presence of glycerol by the photoautotrophically cultivated C. sorokiniana or the heterotrophically cultivated C. sorokiniana to the corresponding syn-(2R,3S)-hydroxy ester with high diastereo- and enantiomeric excess (e.e.). Some additives altered the stereochemical course in the reduction of alpha- and beta-keto esters.

Protection of 2-(3-Thienyl)ethanol with 3-Thienylacetic Acid and Hard Cross- Linked Conducting Films by Electropolymerization of the Ester

NASA Technical Reports Server (NTRS)

Leventis, Nicholas; Dass, Amala; Mulik, Sudir; Sotiriou-Leventis, Chariklia

2005-01-01

The ester (compound 1) of 2-(3-thienyl)ethanol (T-etOH) with 3-thienylacetic acid was synthesized as a monomer whose two thiophene groups could be electropolymerized independently, becoming members of different polymer chains in a highly-crosslinked highly-insoluble polymer. Indeed, 1 was electropolymerized successfully alone and together with 3-methylthiophene (3MeT). Films of poly(1) are hard (3H, as opposed to less than 6B for poly(3MeT)), and the close proximity of the polymeric strands creates pi-stacking interactions. The behavior of 1 suggests that by: (a) limiting the potential used for the oxidation of monomeric esters of T-etOH at the foot of their oxidation waves (less than 1.8 V vs. Ag/AgCl); and, (b) compensating for the decrease in the electrogenerated radical concentration by increasing the monomer concentration, practically all esters of T-etOH should be electropolymerizable. This was confirmed by durable film formation from the archetypical ester of T-etOH, the 2-(3-thienyl)ethyl acetate (T-etOAc), whose homo-electropolymerization is reported for the first time.

Qualitative and quantitative prediction of volatile compounds from initial amino acid profiles in Korean rice wine (makgeolli) model.

PubMed

Kang, Bo-Sik; Lee, Jang-Eun; Park, Hyun-Jin

2014-06-01

In Korean rice wine (makgeolli) model, we tried to develop a prediction model capable of eliciting a quantitative relationship between initial amino acids in makgeolli mash and major aromatic compounds, such as fusel alcohols, their acetate esters, and ethyl esters of fatty acids, in makgeolli brewed. Mass-spectrometry-based electronic nose (MS-EN) was used to qualitatively discriminate between makgeollis made from makgeolli mashes with different amino acid compositions. Following this measurement, headspace solid-phase microextraction coupled to gas chromatography-mass spectrometry (GC-MS) combined with partial least-squares regression (PLSR) method was employed to quantitatively correlate amino acid composition of makgeolli mash with major aromatic compounds evolved during makgeolli fermentation. In qualitative prediction with MS-EN analysis, the makgeollis were well discriminated according to the volatile compounds derived from amino acids of makgeolli mash. Twenty-seven ion fragments with mass-to-charge ratio (m/z) of 55 to 98 amu were responsible for the discrimination. In GC-MS combined with PLSR method, a quantitative approach between the initial amino acids of makgeolli mash and the fusel compounds of makgeolli demonstrated that coefficient of determination (R(2)) of most of the fusel compounds ranged from 0.77 to 0.94 in good correlation, except for 2-phenylethanol (R(2) = 0.21), whereas R(2) for ethyl esters of MCFAs including ethyl caproate, ethyl caprylate, and ethyl caprate was 0.17 to 0.40 in poor correlation. The amino acids have been known to affect the aroma in alcoholic beverages. In this study, we demonstrated that an electronic nose qualitatively differentiated Korean rice wines (makgeollis) by their volatile compounds evolved from amino acids with rapidity and reproducibility and successively, a quantitative correlation with acceptable R2 between amino acids and fusel compounds could be established via HS-SPME GC-MS combined with partial least-squares regression. Our approach for predicting the quantities of volatile compounds in the finished product from initial condition of fermentation will give an insight to food researchers to modify and optimize the qualities of the corresponding products. © 2014 Institute of Food Technologists®

Gas chromatographic-mass spectrometric determination of alkylphosphonic acids from aqueous samples by ion-pair solid-phase extraction on activated charcoal and methylation.

PubMed

Vijaya Saradhi, U V R; Prabhakar, S; Jagadeshwar Reddy, T; Murty, M R V S

2007-07-20

In the present paper, we report an improved ion-pair solid-phase extraction (IP-SPE) method for the analysis of alkylphosphonic acids, namely, methyl, ethyl and propylphosphonic acids, present in the aqueous sample. The aqueous sample was mixed with an ion-pair reagent, phenyltrimethylammonium hydroxide (PTMAH) and passed through activated charcoal SPE cartridge. The retained chemicals in the cartridge were extracted with methanol and analysed by gas chromatography-mass spectrometry (GC-MS) under the electron impact ionization (EI) mode. The analytes were converted to their methyl esters by pyrolytic methylation in the hot GC injection port. The recoveries of alkylphosphonic acids were above 95% and the minimum detection limits were as low as 10 ng/mL. The recovery of the test chemicals was tested with solvents, dichloromethane, n-hexane, ethyl acetate, acetone, acetonitrile and methanol. The chemicals could be efficiently extracted by the hydrophilic solvents. The method did not work at the highly acidic pH (when acidified with dilute HCl) but worked well from pH 4.0 to 14.0. The present method was also tested with other tetra-(methyl, ethyl, propyl and n-butyl)ammonium hydroxides. The test chemicals were not converted to their methyl and ethyl esters with tetramethyl and tetraethylammonium hydroxides, whereas they were converted to their corresponding propyl and n-butyl esters with tetrapropyl and tetra(n-butyl)ammonium hydroxides. The method was also applied to two highly cross-linked polymeric sorbents DSC-6S and Oasis HLB. The recovery of the chemicals on these sorbents was observed to be poor. Methylation using phenyltrimethylammonium hydroxide is non-hazardous and advantageous over methylation using diazomethane. The method was applied to the analysis of aqueous samples given in one of the official proficiency tests conducted by the Organization for the Prohibition of Chemical Weapons and all the spiked chemicals were identified as methyl esters.

Fatty acid ethyl esters in hair: correlation with self-reported ethanol intake in 160 subjects and influence of estroprogestin therapy.

PubMed

Bertol, Elisabetta; Del Bravo, Ester; Vaiano, Fabio; Mari, Francesco; Favretto, Donata

2014-09-01

Fatty acid ethyl esters (FAEEs) are minor ethanol metabolites that can accumulate in hair. The performance of hair FAEEs as a biomarker that can discriminate null or moderate drinking from risky, excessive drinking was verified by evaluating the relationship between self-reported daily alcohol intake and FAEE concentration in hair. The study subjects were 160 healthy volunteers (52% female) that included teetotallers, moderate/social drinkers (< 60 g of ethanol per day), and heavy drinkers (≥ 60 g/day).The estimated daily alcohol intake (EDAI) was assessed by a specific written questionnaire aimed at estimating the measure and the frequency of alcohol drinking and at excluding confounding factors. FAEEs (ethyl myristate, ethyl palmitate, ethyl oleate, and ethyl stearate) were extracted from the hair matrix by overnight incubation in n-hexane/dimethylsulphoxide, purified by solid-phase extraction (SPE) and analyzed by gas chromatography-mass spectrometry (GC-MS) in selected ion monitoring and Electron ionization (EI) mode, using pentadeuterated internal standards. Hair samples exhibited FAEE concentrations (expressed as the sum of the four esters, CFAEE ) ranging from 0.01 to 10.78 ng/mg (average 1.16 and median 0.60 ng/mg). The EDAI was from 0 to 246 g of ethanol per day, average 28 g/day and median 15 g/day. A cut-off of 0.5 ng/mg in 3 cm of a proximal hair segment was adopted to discriminate social drinking from excessive ethanol consumption. False positive samples were identified in subjects using ethanol-containing hair lotions and women on estroprogestin therapy. Specificity of 87% was reached when the identified false positives were excluded from data elaboration. CFAEE in hair at a predetermined cut-off can be used to discriminate between moderate and excessive drinking only when confounding factors are meticulously removed. Copyright © 2014 John Wiley & Sons, Ltd.

Early impact of prescription Omega-3 fatty acids on platelet biomarkers in patients with coronary artery disease and hypertriglyceridemia.

PubMed

Serebruany, Victor L; Miller, Michael; Pokov, Alex N; Lynch, Donald; Jensen, Jesper K; Hallén, Jonas; Atar, Dan

2011-01-01

Prescription omega-3-acid ethyl esters (PO-3A) have been tested for outcome benefits in patients with coronary artery disease (CAD), arrhythmias and heart failure. Some evidence suggests that PO-3A may exert their benefit via inhibiting platelets. We tested the hypothesis that PO-3A may inhibit platelet activity in patients with documented stable CAD, beyond the antiplatelet properties of aspirin and statins. Thirty patients with documented CAD and triglycerides over 250 mg/dl treated with aspirin (70-160 mg/daily) and statins (simvastatin equivalence dose: 5-40 mg/daily) were randomized 1:1:1 to Omacor™ 1 g/day (DHA/EPA ratio 1.25:1.0), Omacor 2 g/day, or a placebo for 2 weeks. Platelet tests including aggregometry and flow cytometry and cartridge analyzer readings were performed at baseline and at 1 and 2 weeks following PO-3A therapy. ADP-induced platelet aggregation (p = 0.037), GP IIb/IIIa antigen (p = 0.031) and activity (p = 0.024), and P-selectin (p = 0.041) were significantly reduced after PO-3A, while platelet/endothelial cell adhesion molecule (p = 0.09), vitronectin receptor (p = 0.16), formation of platelet-monocyte microparticles (p = 0.19) and the VerifyNow IIb/IIIa test (p = 0.27) only exhibited nonsignificant trends suggestive of reduced platelet activity. Finally, collagen- and arachidonic acid-induced aggregation, closure time with the PFA-100 device and expression of thrombospondin (CD36), GP Ib (CD42b), LAMP-3 (CD63), LAMP-1 (CD107a), CD40-ligand (CD154), GP37 (CD165), and PAR-1 receptor intact (SPAN 12) and cleaved (WEDE-15) epitopes were not affected by 2 weeks of PO-3A. Independently of the dose and already at 1 week, short-term therapy with PO-3A provided a modest reduction of platelet activity biomarkers, despite concomitant aspirin and statin therapy, when compared to a placebo. The effect of PO-3A is unique, differs from other known antiplatelet agents and suggests potential pleiotropism. These preliminary randomized data call for confirmation in prospective studies. Copyright © 2011 S. Karger AG, Basel.

Fast and accurate preparation fatty acid methyl esters by microwave-assisted derivatization in the yeast Saccharomyces cerevisiae.

PubMed

Khoomrung, Sakda; Chumnanpuen, Pramote; Jansa-ard, Suwanee; Nookaew, Intawat; Nielsen, Jens

2012-06-01

We present a fast and accurate method for preparation of fatty acid methyl esters (FAMEs) using microwave-assisted derivatization of fatty acids present in yeast samples. The esterification of free/bound fatty acids to FAMEs was completed within 5 min, which is 24 times faster than with conventional heating methods. The developed method was validated in two ways: (1) through comparison with a conventional method (hot plate) and (2) through validation with the standard reference material (SRM) 3275-2 omega-3 and omega-6 fatty acids in fish oil (from the Nation Institute of Standards and Technology, USA). There were no significant differences (P>0.05) in yields of FAMEs with both validations. By performing a simple modification of closed-vessel microwave heating, it was possible to carry out the esterification in Pyrex glass tubes kept inside the closed vessel. Hereby, we are able to increase the number of sample preparations to several hundred samples per day as the time for preparation of reused vessels was eliminated. Pretreated cell disruption steps are not required, since the direct FAME preparation provides equally quantitative results. The new microwave-assisted derivatization method facilitates the preparation of FAMEs directly from yeast cells, but the method is likely to also be applicable for other biological samples.

Photosynthetic CO2 Conversion to Fatty Acid Ethyl Esters (FAEEs) Using Engineered Cyanobacteria.

PubMed

Lee, Hyun Jeong; Choi, Jaeyeon; Lee, Sun-Mi; Um, Youngsoon; Sim, Sang Jun; Kim, Yunje; Woo, Han Min

2017-02-15

Metabolic engineering of cyanobacteria has received attention as a sustainable strategy to convert carbon dioxide to fatty acid-derived chemicals that are widely used in the food and chemical industries. Herein, Synechococcus elongatus PCC 7942, a model cyanobacterium, was engineered for the first time to produce fatty acid ethyl esters (FAEEs) from CO 2 . Due to the lack of an endogenous ethanol production pathway and wax ester synthase (AftA) activity in the wild-type cyanobacterium, we metabolically engineered S. elongatus PCC 7942 by expressing heterologous AftA and introducing the ethanol pathway, resulting in detectable peaks of FAEEs. To enhance FAEE production, a heterologous phosphoketolase pathway was introduced in the FAEE-producing strain to supply acetyl-CoA. Subsequent optimization of the cyanobacterial culture with a hexadecane overlay resulted in engineered S. elongatus PCC 7942 that produced photosynthetic FAEEs (10.0 ± 0.7 mg/L/OD 730 ) from CO 2 . This paper is the first report of photosynthetic production of FAEEs from CO 2 in cyanobacteria.

De novo Biosynthesis of Biodiesel by Escherichia coli in Optimized Fed-Batch Cultivation

PubMed Central

Cai, Ke; Tan, Xiaoming; Lu, Xuefeng

2011-01-01

Biodiesel is a renewable alternative to petroleum diesel fuel that can contribute to carbon dioxide emission reduction and energy supply. Biodiesel is composed of fatty acid alkyl esters, including fatty acid methyl esters (FAMEs) and fatty acid ethyl esters (FAEEs), and is currently produced through the transesterification reaction of methanol (or ethanol) and triacylglycerols (TAGs). TAGs are mainly obtained from oilseed plants and microalgae. A sustainable supply of TAGs is a major bottleneck for current biodiesel production. Here we report the de novo biosynthesis of FAEEs from glucose, which can be derived from lignocellulosic biomass, in genetically engineered Escherichia coli by introduction of the ethanol-producing pathway from Zymomonas mobilis, genetic manipulation to increase the pool of fatty acyl-CoA, and heterologous expression of acyl-coenzyme A: diacylglycerol acyltransferase from Acinetobacter baylyi. An optimized fed-batch microbial fermentation of the modified E. coli strain yielded a titer of 922 mg L−1 FAEEs that consisted primarily of ethyl palmitate, -oleate, -myristate and -palmitoleate. PMID:21629774

Organic reactions catalyzed by methylrhenium trioxide: Reactions of ethyl diazoacetate and organic azides

DOE Office of Scientific and Technical Information (OSTI.GOV)

Zhu, Z.; Espenson, J.H.

1996-10-16

Methylrhenium trioxide (CH{sub 3}ReO{sub 3} or MTO) catalyzes several classes of reactions of ethyl diazoacetate, EDA. It is the first high valent oxo complex for carbene transfer. Under mild conditions and in the absence of other substrates, EDA was converted to a 9:1 mixture of diethyl maleate and diethyl fumarate. In the presence of alcohols, {alpha}-alkoxy ethyl acetates were obtained in good yield. The yields dropped for the larger and more branched alcohols, the balance of material being diethyl maleate and fumarate. An electron-donating group in the para position of phenols favors the formation of {alpha}-phenoxy ethyl acetates. The usemore » of EDA to form {alpha}-thio ethyl acetates and N-substituted glycine ethyl esters, on the other hand, is hardly affected by the size or structure of the parent thiol or amine, with all of these reactions proceeding in high yield. MTO-catalyzed cycloaddition reactions occur between EDA and aromatic imines, olefins, and carbonyl compounds. Three-membered ring products are formed: aziridines, cyclopropanes, and epoxides, respectively. The reactions favor the formation of trans products, and provide a convenient route for the preparation of aziridines. Intermediate carbenoid and nitrenoid species have been proposed. In the presence of an oxygen source such as an epoxide, ethyl diazoacetate and azibenzil are converted to an oxalic acid monoethyl ester and to benzil; at the same time the epoxide was converted to an olefin. 75 refs., 1 fig., 7 tabs.« less

A phytochemical study of the Cuphea glutinosa from Southern Brazil: Na+,K+-ATPase activity inhibition and antioxidant properties.

PubMed

Zago, Adriana M; Carvalho, Fabiano B; Gutierres, Jessié Martins; Bohnert, Crystiani; Fernandes, Marilda da Cruz; Morandini, Liziane M; Coelho, Helena S; Fogaça, Aline O; Andrade, Cinthia M; Mostardeiro, Marco A; Dalcol, Ionara I; Morel, Ademir F

2018-05-21

This study investigated the antioxidant activity of Cuphea glutinosa (CG) and its effect on Na + , K + -ATPase from cardiac muscle. The ethanolic extract showed higher antioxidant capacity compared to aqueous and ethyl acetate fraction. Ethyl acetate fraction showed β-sitosterol-3-O-β-glucoside, kaempferol, quercetin, isoquercetin, gallic acid methyl ester, and gallic acid. The ethanolic extract also reduced the Na + ,K + -ATPase activity. CG presented a promising antioxidant activity and inhibitory effect on the Na + , K + -ATPase activity, supporting biochemical evidences the popular use of this plant in the treatment of heart failure.

[Studies on the chemical constituents of the stems of Piper betle].

PubMed

Yin, Yan; Huang, Xiang-Zhong; Wang, Jiong; Dai, Jian-Hui; Liang, Hui; Dai, Yun

2009-06-01

To study the chemical constituents from the stems of Piper betle. Various chromatographic techniques were used to isolate and purify the constituents. The structures of these compounds were elucidated on the basis of spectral analysis. Nine compounds were isolated from the petroleum ester and ethyl acetate soluble fractions of the 70% acetone extract and their structures were identified as 6beta-hydroxystigmast-4-en-3-one (1), beta-sitosterol (2), stigmasterol (3), oleanolic acid (4), 23-hydroxyursan-12-en-28-oic acid (5), beta-sitosterol-3-O-beta-D-glucoside-6'-O-palmitate (6), beta-daucosterol (7), (2S) -4'-hydroxy- 2,3-dihydroflavonone-7-O-beta-D-glucoside (8) and alpha-ethyl glucoside (9). Among these compounds, 1, 3 -9 are isolated from this plant for the first time.

N-alpha-Cocoyl-L-arginine ethyl ester, DL-pyroglutamic acid salt, as an inactivator of hepatitis B surface antigen.

PubMed Central

Sugimoto, Y; Toyoshima, S

1979-01-01

N-alpha-Cocoyl-L-arginine ethyl ester, DL-pyroglutamic acid salt (CAE), exhibited a strong inactivating effect on hepatitis B surface antigen. Concentrations of CAE required for 50 and 100% inactivation of the antigen were 0.01 to 0.025% and 0.025 to 0.05% respectively. CAE completely inactivated hepatitis B surface antigen at the lowest concentration compared with various compounds including about 500 amino acid derivatives, sodium hypochlorite, 2,4,4'-trichloro-2'-hydroxydiphenyl ether, and some detergents. Furthermore, CAE inactivated vaccinia virus, herpes simplex virus, and influenza virus, whereas poliovirus was not inactivated at all. The results suggest that the inactivating effects of CAE are related to interaction with lipid-containing viral envelopes. PMID:228595

Screening of adjunct cultures and their application in ester formation in Camembert-type cheese.

PubMed

Hong, Q; Liu, X M; Hang, F; Zhao, J X; Zhang, H; Chen, W

2018-04-01

The ethanol content and esterase and alcohol acyltransferase activities are the limiting factors in the synthesis of ethyl esters in Camembert-type cheeses. This study aimed to investigate the effects of alcohol, esterase and alcohol acyltransferase activities on ethyl ester formation in Camembert-type cheeses. Five experimental cheeses were prepared with three adjunct cultures with different enzyme activities and two levels of ethanol content (400 or 800 μg/g). The cheeses were aged for 4 weeks and analysed weekly for basic physicochemical, textural, volatile and sensory properties. The results showed that both the enzyme activity and ethanol content were limiting factors in the synthesis of ethyl esters in the Camembert-type cheeses. Variation in the esterase synthesis activity was observed among lactic acid bacteria, and the starter culture Lactococcus lactis MA 14 LYO distinguished itself through its high acidifying and esterase hydrolysis abilities. The addition of CCFM 12, a lactic acid bacteria strain with high esterase and alcohol acyltransferase activity, along with 400 or 800 μg/g of ethanol, notably enhanced the generation of ethyl esters and the corresponding fruity flavour, without causing dramatic changes in the basic physicochemical indices and microbial profile. In addition, cohesiveness was influenced by the addition of 400 and 800 μg/g of ethanol, and more resilience with 800 μg/g of ethanol had been found. The results showed that the addition of CCFM12 with 400 and 800 μg/g of ethanol may be applied in the production of Camembert cheese to enhance its fruity flavour. Copyright © 2017 Elsevier Ltd. All rights reserved.

Multicomponent Synthesis of a N-Protected Alpha-Amino Ester: Ethyl 2-((4-Methoxyphenyl)Amino)-3-Phenylpropanoate

ERIC Educational Resources Information Center

Le Gall, Erwan; Pignon, Antoine

2012-01-01

This laboratory experiment describes the preparation of a N-protected phenylalanine ethyl ester by a zinc-mediated Mannich-like multicomponent reaction between benzyl bromide, "p"-anisidine, and ethyl glyoxylate. The one-step reaction involves the in situ metallation of benzyl bromide into a benzylzinc reagent and its addition onto imine (Barbier…

40 CFR 414.70 - Applicability; description of the bulk organic chemicals subcategory.

Code of Federal Regulations, 2012 CFR

2012-07-01

..., Calcium Salt Maleic Anhydride Methacrylic Acid *Methacrylic Acid Esters Methane Methyl Ethyl Ketone Methyl Methacrylate Methyl Tert-Butyl Ether Methylisobutyl Ketone *n-Alkanes n-Butyl Alcohol n-Butylacetate n... Acid Nylon Salt Oxalic Acid *Oxo Aldehydes—Alcohols Pentaerythritol Pentane *Pentenes *Petroleum...

40 CFR 414.70 - Applicability; description of the bulk organic chemicals subcategory.

Code of Federal Regulations, 2014 CFR

2014-07-01

..., Calcium Salt Maleic Anhydride Methacrylic Acid *Methacrylic Acid Esters Methane Methyl Ethyl Ketone Methyl Methacrylate Methyl Tert-Butyl Ether Methylisobutyl Ketone *n-Alkanes n-Butyl Alcohol n-Butylacetate n... Acid Nylon Salt Oxalic Acid *Oxo Aldehydes—Alcohols Pentaerythritol Pentane *Pentenes *Petroleum...

40 CFR 414.70 - Applicability; description of the bulk organic chemicals subcategory.

Code of Federal Regulations, 2011 CFR

2011-07-01

..., Calcium Salt Maleic Anhydride Methacrylic Acid *Methacrylic Acid Esters Methane Methyl Ethyl Ketone Methyl Methacrylate Methyl Tert-Butyl Ether Methylisobutyl Ketone *n-Alkanes n-Butyl Alcohol n-Butylacetate n... Acid Nylon Salt Oxalic Acid *Oxo Aldehydes—Alcohols Pentaerythritol Pentane *Pentenes *Petroleum...

40 CFR 414.70 - Applicability; description of the bulk organic chemicals subcategory.

Code of Federal Regulations, 2013 CFR

2013-07-01

..., Calcium Salt Maleic Anhydride Methacrylic Acid *Methacrylic Acid Esters Methane Methyl Ethyl Ketone Methyl Methacrylate Methyl Tert-Butyl Ether Methylisobutyl Ketone *n-Alkanes n-Butyl Alcohol n-Butylacetate n... Acid Nylon Salt Oxalic Acid *Oxo Aldehydes—Alcohols Pentaerythritol Pentane *Pentenes *Petroleum...

Icosapent ethyl: Eicosapentaenoic acid concentration and triglyceride-lowering effects across clinical studies.

PubMed

Bays, Harold E; Ballantyne, Christie M; Doyle, Ralph T; Juliano, Rebecca A; Philip, Sephy

2016-09-01

Icosapent ethyl is a high-purity prescription form of eicosapentaenoic acid (EPA) ethyl ester approved at a dose of 4g/day as an adjunct to diet to reduce triglyceride (TG) levels in adult patients with severe (≥500mg/dL) hypertriglyceridemia. This post-hoc exploratory analysis examined the relationship of icosapent ethyl dose with EPA concentrations in plasma and red blood cells (RBCs) across 3 clinical studies-a phase 1 pharmacokinetic study in healthy adult volunteers and 2 pivotal phase 3 studies (MARINE and ANCHOR) in adult patients with hypertriglyceridemia-and examined the relationship between EPA levels and TG-lowering effects in MARINE and ANCHOR. In all 3 studies, icosapent ethyl produced dose-dependent increases in the concentrations of EPA in plasma and RBCs. In both MARINE and ANCHOR, these dose-dependent EPA increases correlated with the degree of TG level lowering (all P<0.01). In patients with high TG levels (≥200mg/dL) and treated with icosapent ethyl 4g/day, the end-of-treatment plasma and RBC EPA concentrations were >170μg/mL and>70μg/mL, respectively. These studies support icosapent ethyl as producing predictable dose-dependent pharmacokinetics/pharmacodynamics, with TG level lowering dependent upon icosapent ethyl dose and EPA concentrations in plasma and RBCs. Copyright © 2016 The Authors. Published by Elsevier Inc. All rights reserved.

Prescription Omega-3 Fatty Acid Products and Dietary Supplements Are Not Interchangeable.

PubMed

Hilleman, Daniel; Smer, Aiman

2016-01-01

To provide an overview of prescription and dietary supplement omega-3 fatty acid (OM3-FA) products and considerations for clinical use. Narrative review. The PubMed database was searched for cardiovascular-related investigations focused on eicosapentaenoic acid (EPA) and/or docosahexaenoic acid (DHA) (limit: English-only articles). Additional regulatory information on prescription and dietary supplements was obtained from United States Food and Drug Administration online sources. Prescription QM3-FA products are supported by robust clinical development and safety monitoring programs, whereas dietary supplements are not required to demonstrate safety or efficacy prior to marketing. There are no over-the-counter OM3-FA products available in the United States. Investigations of OM3-FA dietary supplements show that quantities of EPA and DHA are highly variable within and between brands. Dietary supplements also may contain potentially harmful components, including oxidized OM3-FA, other lipids, cholesterol, and toxins. Prescription OM3-FA products may contain DHA and EPA or EPA alone. All prescription OM3-FA products have demonstrated statistically significant triglyceride reduction as monotherapy or in combination with statins in patients with hypertriglyceridemia. Differential effects between products containing EPA and DHA compared with a high-purity EPA product (icosapent ethyl) have clinical implications: Increases in low-density lipoprotein cholesterol associated with DHA have the potential to confound strategies for managing patients with dyslipidemia. Cardiovascular outcomes studies of prescription CM3-FA products are ongoing. OM3-FA dietary supplements should not be substituted for prescription products, and prescription OM3-FA products that contain DHA are not equivalent to or interchangeable with high-purity EPA (icosapent ethyl) and should not be substituted for it.

Critical aggregates concentration of fatty esters present in biodiesel determined by turbidity and fluorescence.

PubMed

Froehner, Sandro; Sánez, Juan; Dombroski, Luiz Fernando; Gracioto, Maria Paula

2017-09-01

Biodiesel for combustible engine is available as mixture of fossil diesel and fatty esters obtained by transesterification of vegetable oils. The use of biodiesel reduces the amount of SO x , mainly. However, it was already observed that biodiesel has a different behavior in environment in cases of accidental spill and groundwater contamination. It was noticed that the biodegradation of hydrocarbons (cyclic and aliphatic) in the presence of biodiesel are speeded, although the mechanism is still unclear. Considering the chemical structure of fatty esters, it was investigated the formation of aggregates in water solution by fatty esters present in commercial biodiesel. In Brazil, biodiesel is composed by 95% of fossil diesel and 5% of fatty esters mixture. In this work, fatty esters were treated as neutral surfactant, i.e., it was treated as a molecule with polar and non-polar part. Turbidity and fluorescence were used to determine the critical aggregates concentration (CAC). Water solutions containing fatty esters were examined exploiting changes in turbidity and fluorescence intensity of pyrene. Abrupt changes were attributed to aggregates formation, following the same behavior of traditional amphiphilic compounds. It was determined the CAC for ethyl palmitate, ethyl stearate, ethyl oleate, and ethyl linoleate. The values of CAC for fatty esters varied from 1.91 to 4.27 μmol/L, while CAC for the mixture of esters (biodiesel) was 2.01 for methyl esters and 1.19 for ethyl esters, both prepared using soybean oil. The aggregates formation was also determined by fluorescence measurements considering the changes in intensity of peaks I and III of pyrene. Pyrene senses the changes in environment polarity. The values found of CAC by fluorescence for individual ethyl esters varied from 1.85 to 3.21 μmol/L, while mixtures of ethyl esters was 2.23 and 2.07 μmol/L for mixture of methyl esters. The results clearly showed that fatty esters form aggregates and might be responsible for speed degradation of compounds by accommodation of them in inner part of aggregates.

Natural Docosahexaenoic Acid in the Triglyceride Form Attenuates In Vitro Microglial Activation and Ameliorates Autoimmune Encephalomyelitis in Mice.

PubMed

Mancera, Pilar; Wappenhans, Blanca; Cordobilla, Begoña; Virgili, Noemí; Pugliese, Marco; Rueda, Fèlix; Espinosa-Parrilla, Juan F; Domingo, Joan C

2017-06-30

Many neurodegenerative diseases are associated, at least in part, to an inflammatory process in which microglia plays a major role. The effect of the triglyceride form of the omega-3 polyunsaturated fatty acid docosahexaenoic acid (TG-DHA) was assayed in vitro and in vivo to assess the protective and anti-inflammatory activity of this compound. In the in vitro study, BV-2 microglia cells were previously treated with TG-DHA and then activated with Lipopolysaccharide (LPS) and Interferon-gamma (IFN-γ). TG-DHA treatment protected BV-2 microglia cells from oxidative stress toxicity attenuating NO production and suppressing the induction of inflammatory cytokines. When compared with DHA in the ethyl-ester form, a significant difference in the ability to inhibit NO production in favor of TG-DHA was observed. TG-DHA inhibited significantly splenocyte proliferation but isolated CD4+ lymphocyte proliferation was unaffected. In a mice model of autoimmune encephalomyelitis (EAE), 250 mg/kg/day oral TG-DHA treatment was associated with a significant amelioration of the course and severity of the disease as compared to untreated animals. TG-DHA-treated EAE mice showed a better weight profile, which is a symptom related to a better course of encephalomyelitis. TG-DHA may be a promising therapeutic agent in neuroinflammatory processes and merit to be more extensively studied in human neurodegenerative disorders.

Red Blood Cell Docosapentaenoic Acid (DPA n-3) is Inversely Associated with Triglycerides and C-reactive Protein (CRP) in Healthy Adults and Dose-Dependently Increases Following n-3 Fatty Acid Supplementation

PubMed Central

Skulas-Ray, Ann C.; Flock, Michael R.; Richter, Chesney K.; Harris, William S.; West, Sheila G.; Kris-Etherton, Penny M.

2015-01-01

The role of the long-chain omega-3 (n-3) fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in lipid metabolism and inflammation has been extensively studied; however, little is known about the relationship between docosapentaenoic acid (DPA, 22:5 n-3) and inflammation and triglycerides (TG). We evaluated whether n-3 DPA content of red blood cells (RBC) was associated with markers of inflammation (interleukin-6 (IL-6), tumor necrosis factor α (TNF-α), and C-reactive protein (CRP) and fasting TG prior to n-3 supplementation in two studies (Study 1: n = 115, aged 20–44 years, body mass index (BMI) 20–30 kg/m2, TG = 34–176 mg/dL; Study 2: n = 28, aged 22–65 years, BMI 24–37 kg/m2, TG = 141–339 mg/dL). We also characterized the dose-response effects of n-3 fatty acid supplementation on RBC n-3 DPA after five months of supplementation with fish oil (Study 1: 0, 300, 600, 900, and 1800 mg/day EPA + DHA) and eight weeks of prescription n-3 ethyl esters (Study 2: 0, 850, and 3400 mg/day EPA + DHA). In Study 1, RBC n-3 DPA was inversely correlated with CRP (R2 = 36%, p < 0.001) and with fasting TG (r = −0.30, p = 0.001). The latter finding was replicated in Study 2 (r = −0.33, p = 0.04). In both studies, n-3 supplementation significantly increased RBC n-3 DPA dose-dependently. Relative increases were greater for Study 1, with increases of 29%–61% vs. 14%–26% for Study 2. The associations between RBC n-3 DPA, CRP, and fasting TG may have important implications for the prevention of atherosclerosis and chronic inflammatory diseases and warrant further study. PMID:26247967

Psychotria viridis: Chemical constituents from leaves and biological properties.

PubMed

Soares, Débora B S; Duarte, Lucienir P; Cavalcanti, André D; Silva, Fernando C; Braga, Ariadne D; Lopes, Miriam T P; Takahashi, Jacqueline A; Vieira-Filho, Sidney A

2017-01-01

The phytochemical study of hexane, chloroform and methanol extracts from leaves of Psychotria viridis resulted in the identification of: the pentacyclic triterpenes, ursolic and oleanolic acid; the steroids, 24-methylene-cycloartanol, stigmasterol and β-sitosterol; the glycosylated steroids 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol; a polyunsaturated triterpene, squalene; the esters of glycerol, 1-palmitoylglycerol and triacylglycerol; a mixture of long chain hydrocarbons; the aldehyde nonacosanal; the long chain fat acids hentriacontanoic, hexadecanoic and heptadenoic acid; the ester methyl heptadecanoate; the 4-methyl-epi-quinate and two indole alkaloids, N,N-dimethyltryptamine (DMT) and N-methyltryptamine. The chemical structures were determined by means of spectroscopic (IR, 1H and 13C NMR, HSQC, HMBC and NOESY) and spectrometric (CG-MS and LCMS-ESI-ITTOF) methods. The study of biologic properties of P. viridis consisted in the evaluation of the acetylcholinesterase inhibition and cytotoxic activities. The hexane, chloroform, ethyl acetate and methanol extracts, the substances 24-methylene-cycloartanol, DMT and a mixture of 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol showed cholinesterase inhibiting activity. This activity induced by chloroform and ethyl acetate extracts was higher than 90%. The methanol and ethyl acetate extracts inhibit the growth and/or induce the death of the tumor cells strains B16F10 and 4T1, without damaging the integrity of the normal cells BHK and CHO. DMT also demonstrated a marked activity against tumor cell strains B16F10 and 4T1.

Advanced Biosensors for Amino Acid Detection. Phase 1

DTIC Science & Technology

1989-12-31

dissolved in CHCl 3 , where it was found effective for extracting phenylethylamine (C 6 H5 CH2 NH2 ) and dt-phenylglycine ethyl ester (C 6 H6 (NH2...promoted. Since resonance effects are important in aromatic amines and since p-nitroani- line is an extremely weak nucleophile, the lack of

Advanced Biosensors for Amino Acid Detection

DTIC Science & Technology

1990-04-18

when (II) was dissolved in CHCl 3 , and found effective for extracting phenylethylamine (C 6 H5CH2 CH2 NH)) and di-phenylglycine ethyl ester (C 6 H6...reaction was promoted. Since reson nce effects are important in aromatic amines and since p-nitroanilive is an extremely weak nucleophile, lack of

Apple Aminoacid Profile and Yeast Strains in the Formation of Fusel Alcohols and Esters in Cider Production.

PubMed

Eleutério Dos Santos, Caroline Mongruel; Pietrowski, Giovana de Arruda Moura; Braga, Cíntia Maia; Rossi, Márcio José; Ninow, Jorge; Machado Dos Santos, Tâmisa Pires; Wosiacki, Gilvan; Jorge, Regina Maria Matos; Nogueira, Alessandro

2015-06-01

The amino acid profile in dessert apple must and its effect on the synthesis of fusel alcohols and esters in cider were established by instrumental analysis. The amino acid profile was performed in nine apple musts. Two apple musts with high (>150 mg/L) and low (<75 mg/L) nitrogen content, and four enological yeast strains, were used in cider fermentation. The aspartic acid, asparagine and glutamic acid amino acids were the majority in all the apple juices, representing 57.10% to 81.95%. These three amino acids provided a high consumption (>90%) during fermentation in all the ciders. Principal component analysis (PCA) explained 81.42% of data variability and the separation of three groups for the analyzed samples was verified. The ciders manufactured with low nitrogen content showed sluggish fermentation and around 50% less content of volatile compounds (independent of the yeast strain used), which were mainly 3-methyl-1-butanol (isoamyl alcohol) and esters. However, in the presence of amino acids (asparagine, aspartic acid, glutamic acid and alanine) there was a greater differentiation between the yeasts in the production of fusel alcohols and ethyl esters. High contents of these aminoacids in dessert apple musts are essential for the production of fusel alcohols and most of esters by aromatic yeasts during cider fermentation. © 2015 Institute of Food Technologists®

[Chemical Constituents from Ethyl Acetate Extract of Psidium guajava Leaves (II)].

PubMed

Ouyang, Wen; Zhu, Xiao-ai; He, Cui-xia; Chen, Xue-xiang; Ye, Shu-min; Peng, Shan; Cao, Yong

2015-08-01

To study the chemical constituents from ethyl acetate extract of Psidium guajava leaves. The constituents were separated and purified by silica gel and Sephadex LH-20 column chromatography and their structures were identified on the basis of physicochemical properties and spectral data. Eleven compounds were isolated and identified as 6,10,14-trimethyl-2-pentadecanone (1), phytyl-acetate (2), cubenol (3), eucalyptin (4), n-docosanoic acid-p-hydroxy-phenethylol ester (5),8-methyl-5,7- dihydroxy-flavonone (6), 6-methyl-5,7-dihydroxy-flavonone (7), betulinic acid (8), carnosol (9), quercetin (10), and 2,4,6-tirhydroxy- 3,5-dimethyl-diphenylketone-4-O-(6'"-O-galloyl)-β-D-glucoside (11). Compounds 1-9 are isolated from this plant for the first time.

75 FR 17769 - In the Matter of Certain Products Advertised as Containing Creatine Ethyl Ester; Notice of...

Federal Register 2010, 2011, 2012, 2013, 2014

2010-04-07

... Advertised as Containing Creatine Ethyl Ester; Notice of Commission Issuance of a Limited Exclusion Order Against the Products Advertised as Containing Creatine Ethyl Ester of Respondents Found in Default... importation of certain products advertised as containing creatine ethyl ester by reason of false advertising...

Permeation enhancement via thiolation: in vitro and ex vivo evaluation of hyaluronic acid-cysteine ethyl ester.

PubMed

Laffleur, Flavia; Psenner, Julia; Suchaoin, Wongsakorn

2015-07-01

It was the aim of this study to evaluate the permeation-enhancing effect of synthesized thiolated hyaluronic acid (HA). HA, a naturally found polysaccharide, was chemically modified with l-cysteine ethyl ether (C) via amide bond formation. In vitro permeation enhancement was tested on Caco-2 cells with two compounds, sulforhodamine (SR) and fluorescein isothiocyanate-dextran (FD4). Cytotoxicity assays as lactate dehydrogenase and thiazolyl blue tetrazolium bromide (MTT) were performed on colon carcinoma cell line. Transepithelial electrical resistance (TEER) measurements were conducted. Ex vivo evaluation was accomplished on rat intestinal mucosa in order to predict the permeation enhancing effect with SR, sodium fluorescein (SF), and FD4, respectively. The MTT as well as lactate dehydrogenase revealed no toxicity over time periods of 3 and 12 h, respectively. The bioconjugate is biocompatible and safe to use. Furthermore, TEER measurements showed the integrity of tight junctions. The in vitro permeation studies on cell studies exhibit 1.28-fold enhancement for SR and 1.47-fold enhancement for FD4 with hyaluronic acid-cysteine ethyl ester (HAC) in comparison to unmodified one. The ex vivo transport studies exhibit 1.9-fold enhancement for SF, 1.31-fold enhancement for Rhodamine123, and 1.3-fold enhancement for FD4 with HAC in comparison to unmodified one, respectively. Thus, the promising results encourage further investigations and exploitation of this versatile polysaccharide. © 2015 Wiley Periodicals, Inc. and the American Pharmacists Association.

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

PubMed Central

Bruns, Hilke; Riclea, Ramona

2011-01-01

Summary The volatiles released by Micromonospora aurantiaca were collected by means of a closed-loop stripping apparatus (CLSA) and analysed by GC–MS. The headspace extracts contained more than 90 compounds from different classes. Fatty acid methyl esters (FAMEs) comprised the major compound class including saturated unbranched, monomethyl and dimethyl branched FAMEs in diverse structural variants: Unbranched, α-branched, γ-branched, (ω−1)-branched, (ω−2)-branched, α- and (ω−1)-branched, γ- and (ω−1)-branched, γ- and (ω−2)-branched, and γ- and (ω−3)-branched FAMEs. FAMEs of the last three types have not been described from natural sources before. The structures for all FAMEs have been suggested based on their mass spectra and on a retention index increment system and verified by the synthesis of key reference compounds. In addition, the structures of two FAMEs, methyl 4,8-dimethyldodecanoate and the ethyl-branched compound methyl 8-ethyl-4-methyldodecanoate were deduced from their mass spectra. Feeding experiments with isotopically labelled [2H10]leucine, [2H10]isoleucine, [2H8]valine, [2H5]sodium propionate, and [methyl-2H3]methionine demonstrated that the responsible fatty acid synthase (FAS) can use different branched and unbranched starter units and is able to incorporate methylmalonyl-CoA elongation units for internal methyl branches in various chain positions, while the methyl ester function is derived from S-adenosyl methionine (SAM). PMID:22238549

Effects of air exposure, temperature and additives on fermentation characteristics, yeast count, aerobic stability and volatile organic compounds in corn silage.

PubMed

Weiss, K; Kroschewski, B; Auerbach, H

2016-10-01

Ensiling conditions strongly influence fermentation characteristics, yeast count, and aerobic stability. Numerous volatile organic compounds including esters are produced, which may negatively affect feed intake and animal performance and air quality. In addition to a farm survey, 3 laboratory experiments were carried out to study the effects of air (by delayed sealing or by air infiltration during anaerobic storage), temperature (20 and 35°C), and various types of additives [blends of either sodium benzoate and sodium propionate (SBSP) or of sodium benzoate and potassium sorbate (SBPS); buffered mixture of formic and propionic acids (FAPA); homofermentative inoculant (LAB)]. After additive treatment, chopped whole corn plants were packed into 1.5-L glass jars and stored for several months. For treatments with air infiltration, glass jars with holes in the lid and body were used. The farm survey in 2009 revealed large variation in lactate, acetate, ethanol, n-propanol, and 1,2-propanediol concentrations. Whereas ethyl esters were detected in all silages, the mean ethyl lactate concentrations were higher than those for ethyl acetate (474 vs. 38mg/kg of dry matter). In the ensiling experiments, few unequivocal effects of the tested factors on the analyzed parameters were observed due to many interactions. Delayed ensiling without additives decreased lactic acid production but, in one trial, increased acetic acid and had no effect on ethanol. The effect of delayed sealing on yeast counts and aerobic stability differed widely among experiments. Air infiltration during fermentation tested in one trial did not alter lactic acid production, but resulted in more acetic acid in delayed and more ethanol than in promptly sealed untreated silages. Greater ethanol production was associated with increased yeast numbers. Storage at high temperature resulted in lower lactic acid and n-propanol, and a trend toward reduced ethanol production was observed. The additive FAPA consistently caused increased ethanol and reduced n-propanol levels with no effect on yeast counts and aerobic stability. When the additives SBSP and SBPS decreased n-propanol and ethanol, reduced yeast counts were also found. Ethyl ester formation was strongly correlated with those of ethanol and to a lesser degree with those of the respective acid. Copyright © 2016 American Dairy Science Association. Published by Elsevier Inc. All rights reserved.

Randomized controlled trial of ethyl-eicosapentaenoic acid in Huntington disease: the TREND-HD study.

PubMed

2008-12-01

To determine whether ethyl-eicosapentaenoic acid (ethyl-EPA), an omega-3 fatty acid, improves the motor features of Huntington disease. Six-month multicenter, randomized, double-blind, placebo-controlled trial followed by a 6-month open-label phase without disclosing initial treatment assignments. Forty-one research sites in the United States and Canada. Three hundred sixteen adults with Huntington disease, enriched for a population with shorter trinucleotide (cytosine-adenine-guanine) repeat length expansions. Random assignment to placebo or ethyl-EPA, 1 g twice a day, followed by open-label treatment with ethyl-EPA. Six-month change in the Total Motor Score 4 component of the Unified Huntington's Disease Rating Scale analyzed for all research participants and those with shorter cytosine-adenine-guanine repeat length expansions (<45). At 6 months, the Total Motor Score 4 point change for patients receiving ethyl-EPA did not differ from that for those receiving placebo. No differences were found in measures of function, cognition, or global impression. Before public disclosure of the 6-month placebo-controlled results, 192 individuals completed the open-label phase. The Total Motor Score 4 change did not worsen for those who received active treatment for 12 continuous months compared with those who received active treatment for only 6 months (2.0-point worsening; P=.02). Ethyl-EPA was not beneficial in patients with Huntington disease during 6 months of placebo-controlled evaluation. Clinical Trial Registry clinicaltrials.gov Identifier: NCT00146211.

Prescription n-3 fatty acids, but not eicosapentaenoic acid alone, improve reference memory-related learning ability by increasing brain-derived neurotrophic factor levels in SHR.Cg-Lepr(cp)/NDmcr rats, a metabolic syndrome model.

PubMed

Hashimoto, Michio; Inoue, Takayuki; Katakura, Masanori; Tanabe, Yoko; Hossain, Shahdat; Tsuchikura, Satoru; Shido, Osamu

2013-10-01

Metabolic syndrome is implicated in the decline of cognitive ability. We investigated whether the prescription n-3 fatty acid administration improves cognitive learning ability in SHR.Cg-Lepr(cp)/NDmcr (SHR-cp) rats, a metabolic syndrome model, in comparison with administration of eicosapentaenoic acid (EPA, C20:5, n-3) alone. Administration of TAK-085 [highly purified and concentrated n-3 fatty acid formulation containing EPA ethyl ester and docosahexaenoic acid (DHA, C22:6, n-3) ethyl ester] at 300 mg/kg body weight per day for 13 weeks reduced the number of reference memory-related errors in SHR-cp rats, but EPA alone had no effect, suggesting that long-term TAK-085 administration improves cognitive learning ability in a rat model of metabolic syndrome. However, the working memory-related errors were not affected in either of the rat groups. TAK-085 and EPA administration increased plasma EPA and DHA levels of SHR-cp rats, associating with an increase in EPA and DHA in the cerebral cortex. The TAK-085 administration decreased the lipid peroxide levels and reactive oxygen species in the cerebral cortex and hippocampus of SHR-cp rats, suggesting that TAK-085 increases antioxidative defenses. Its administration also increased the brain-derived neurotrophic factor levels in the cortical and hippocampal tissues of TAK-085-administered rats. The present study suggests that long-term TAK-085 administration is a possible therapeutic strategy for protecting against metabolic syndrome-induced learning decline.

Kinetic Study of the Aroxyl-Radical-Scavenging Activity of Five Fatty Acid Esters and Six Carotenoids in Toluene Solution: Structure-Activity Relationship for the Hydrogen Abstraction Reaction.

PubMed

Mukai, Kazuo; Yoshimoto, Maya; Ishikura, Masaharu; Nagaoka, Shin-Ichi

2017-08-17

A kinetic study of the reaction between an aroxyl radical (ArO • ) and fatty acid esters (LHs 1-5, ethyl stearate 1, ethyl oleate 2, ethyl linoleate 3, ethyl linolenate 4, and ethyl arachidonate 5) has been undertaken. The second-order rate constants (k s ) for the reaction of ArO • with LHs 1-5 in toluene at 25.0 °C have been determined spectrophotometrically. The k s values obtained increased in the order of LH 1 < 2 < 3 < 4 < 5, that is, with increasing the number of double bonds included in LHs 1-5. The k s value for LH 5 was 2.93 × 10 -3 M -1 s -1 . From the result, it has been clarified that the reaction of ArO • with LHs 1-5 was explained by an allylic hydrogen abstraction reaction. A similar kinetic study was performed for the reaction of ArO • with six carotenoids (Car-Hs 1-6, astaxanthin 1, β-carotene 2, lycopene 3, capsanthin 4, zeaxanthin 5, and lutein 6). The k s values obtained increased in the order of Car-H 1 < 2 < 3 < 4 < 5 < 6. The k s value for Car-H 6 was 8.4 × 10 -4 M -1 s -1 . The k s values obtained for Car-Hs 1-6 are in the same order as that of the values for LHs 1-5. The results of detailed analyses of the k s values for the above reaction indicated that the reaction was also explained by an allylic hydrogen abstraction reaction. Furthermore, the structure-activity relationship for the reaction was discussed by taking the result of density functional theory calculation reported by Martinez and Barbosa into account.

Volatile flavor compounds, total polyphenolic contents and antioxidant activities of a China gingko wine.

PubMed

Wang, Xu; Xie, Kelin; Zhuang, Haining; Ye, Ran; Fang, Zhongxiang; Feng, Tao

2015-09-01

The volatile compounds in gingko wine, a novel functional wine, were extracted by head-space solid phase micro-extraction (SPME) and analyzed by gas chromatography-mass spectrometry (GC-MS) coupled with odor activity value (OAV) and relative odor contribution (ROC) analyses. In addition, the total polyphenolic content of gingko wine was determined using the Folin-Ciocalteu reagent, and its antioxidant capacity was evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. Fifty-eight compounds were tentatively identified, including 13 esters, 10 alcohols, 11 acids, 12 carbonyl compounds, 2 lactones, 2 phenols, and 8 hydrocarbons. Ethyl hexanoate, ethyl pentanoate, nonanal, ethyl butyrate and ethyl heptanoate were the major contributors to the gingko wine aroma based on the results of OAV and ROC. The total phenols content of the gingko wine was 456 mg/L gallic acid equivalents, and its antioxidant capacity was higher than those of typical Chinese liquors analyzed in this paper. Copyright © 2015 Elsevier Ltd. All rights reserved.

Self-assembly modes of glycyrrhetinic acid esters in view of the crystal packing of related triterpene molecules.

PubMed

Langer, Dominik; Wicher, Barbara; Szczołko, Wojciech; Gdaniec, Maria; Tykarska, Ewa

2016-08-01

The crystal structures of three ester derivatives of glycyrrhetinic acid (GE) are reported. X-ray crystallography revealed that despite differences in the size of the ester substituents (ethyl, isopropyl and 2-morpholinoethyl) the scheme of molecular self-assembly is similar in all three cases but differs significantly from that observed in other known GE esters. According to our analysis, the two basic patterns of self-assembly of GE esters observed in their unsolvated crystals correspond to two distinct orientations of the ester groups relative to the triterpene backbone. Moreover, comparison of the self-assembly modes of GE esters in their unsolvated forms with the supramolecular organization of GE and carbenoxolone in their solvated crystals revealed that ester substituents replace solvent molecules hydrogen bonded to the COOH group at the triterpene skeleton, resulting in similar packing arrangements of these compounds.

Endophytic fungi producing of esterases: Evaluation in vitro of the enzymatic activity using pH indicator

PubMed Central

Lisboa, Helen Cristina Fávero; Biasetto, Carolina Rabal; de Medeiros, João Batista; Araújo, Ângela Regina; Silva, Dulce Helena Siqueira; Teles, Helder Lopes; Trevisan, Henrique Celso

2013-01-01

A sensitive and efficient colorimetric method was optimized for detection of esterase enzymes produced by endophytic fungi for development of High-Throughput Screening (HTS). The fungi were isolated and obtained previously from plant species of Cerrado and Atlantic Forest located in areas of environmental preservation in the State of Sao Paulo / Brazil, as part of the project “Chemical and biological prospecting endophytic fungi associated to plant species of Cerrado and Atlantic Forest”. The compounds ethyl butyrate, ethyl acetate and methyl propionate were used as standards esters which were hydrolyzed by extracellular enzyme from endophytic fungi (EC. 3.1.1.1 - carboxyl-esterases) for production of carboxylic acids. Thus, the reduction of the pH increases the protonated indicator concentration (bromothymol blue), changing the color of the reaction medium (from blue to yellow), that can be observed and measured by spectrophotometry at 616 nm. The methodology with acid-base indicator was performed on 13 microorganisms, aiming Periconia atropurpurea as a potential source of esterase for biotransformation of short chain esters. The results also evidenced that this methodology showed to be efficient, fast, cheap, having low consumption of reagents and easy development, and can be applied to screen carboxylic-ester hydrolases in a large number of microorganisms. PMID:24516461

Synthesis of biodiesel from pongamia oil using heterogeneous ion-exchange resin catalyst.

PubMed

Jaya, N; Selvan, B Karpanai; Vennison, S John

2015-11-01

Biodiesel is a clean-burning renewable substitute fuel for petroleum. Biodiesel could be effectively produced by transesterification reaction of triglycerides of vegetable oils with short-chain alcohols in the presence of homogeneous or heterogeneous catalysts. Conventionally, biodiesel manufacturing processes employ strong acids or bases as catalysts. But, separation of the catalyst and the by-product glycerol from the product ester is too expensive to justify the product use as an automobile fuel. Hence heterogeneous catalysts are preferred. In this study, transesterification of pongamia oil with ethanol was performed using a solid ion-exchange resin catalyst. It is a macro porous strongly basic anion exchange resin. The process parameters affecting the ethyl ester yield were investigated. The reaction conditions were optimized for the maximum yield of fatty acid ethyl ester (FAEE) of pongamia oil. The properties of FAEE were compared with accepted standards of biodiesel. Engine performance was also studied with pongamia oil diesel blend and engine emission characteristics were observed. Copyright © 2015 Elsevier Inc. All rights reserved.

40 CFR 180.1323 - Ethyl-2E,4Z-decadienoate (Pear Ester); exemption from the requirement of a tolerance.

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 24 2014-07-01 2014-07-01 false Ethyl-2E,4Z-decadienoate (Pear Ester... RESIDUES IN FOOD Exemptions From Tolerances § 180.1323 Ethyl-2E,4Z-decadienoate (Pear Ester); exemption... for residues of the biochemical pesticide, ethyl-2E,4Z-decadienoate (pear ester), in or on all food...

A Novel ω-3 Acid Ethyl Ester Formulation Incorporating Advanced Lipid TechnologiesTM (ALT®) Improves Docosahexaenoic Acid and Eicosapentaenoic Acid Bioavailability Compared with Lovaza®.

PubMed

Lopez-Toledano, Miguel A; Thorsteinsson, Thorsteinn; Daak, Ahmed; Maki, Kevin C; Johns, Colleen; Rabinowicz, Adrian L; Sancilio, Frederick D

2017-03-01

The US Food and Drug Administration has approved several highly purified ω-3 fatty acid prescription drugs for the treatment of severe hypertriglyceridemia. These differ in the amounts and forms of docosahexaenoic acid (DHA) and/or eicosapentaenoic acid (EPA). This study compared the bioavailability of SC401 (1530 mg EPA-ethyl esters [EEs] and DHA-EEs plus Advanced Lipid Technologies ⁎ [ALT † ], a proprietary lipid-delivery platform to improve absorption), with. Lovaza ‡ (3600 mg ω-3, primarily EPA-EEs and DHA-EEs) under low-fat feeding conditions. This was a Phase I, randomized, open-label, single-dose, 2-way crossover study in healthy participants housed from day -3 to day 2 in each treatment period. Blood samples for pharmacokinetic measurements were collected before and after dosing, and safety profile and tolerability were assessed. In unadjusted analyses, SC401 had 5% lower C max and approximately the same AUC 0-last of EPA + DHA total lipids compared with Lovaza. When adjusted for baseline, SC401 had ~6% higher C max and 18% higher AUC 0-last for EPA + DHA total lipids, and dose- and baseline-adjusted analyses found that SC401 had ~149% higher C max and 178% higher AUC 0-last than Lovaza for EPA + DHA total lipids. The T max was also substantially longer with Lovaza (~10 hours) than with SC401 (~6 hours). These results indicate that SC401, an ω-3 acid EE formulation containing ALT † achieved high bioavailability of EPA and DHA, at a lower dose (1530 mg) than Lovaza (3600 mg), under low-fat feeding conditions. Copyright © 2017 Elsevier HS Journals, Inc. All rights reserved.

Lipids and fatty acids in roasted chickens.

PubMed

Souza, S A; Visentainer, J V; Matsushita, M; Souza, N E

1999-09-01

Total lipids from meat portions of breast, thigh, wing, side and back with and without skin from 10 roasted chickens were extracted with chloroform and methanol and gravimetrically determined, and their fatty acids were analysed as methyl esters by gaseous chromatography, using a flame ionization detector and capillary column. The main fatty acids found were: C16:0, C18:1 omega 9, and C18:2 omega 6. The average ratio observed between PUFA/SFA was of 0.98, mainly due to the great concentration of the C18:2 omega 6 fatty acid, with an average of 26.75%. Regarding to the lipids content, the skinless breast showed the lowest content, 0.78 g/100 g, while the back with skin was the one with the highest content, 12.13 g/100 g except for the pure skin, with 26.54 grams of lipids by 100 grams.

ESR study of electron reactions with esters and triglycerides

DOE Office of Scientific and Technical Information (OSTI.GOV)

Sevilla, M.D.; Morehouse, K.M.; Swarts, S.

1981-04-02

Reactions which occurred after electron attachment at 77K to a number of small carboxylic acid esters and triglycerides in an aqueous glass are reported. Most ester anions are found to decay on warming to form alkyl radicals by ..beta.. scission: RC(O/sup -/)OR' ..-->.. RCO/sub 2//sup -/ + R'.. The alkyl radical (R'.) produced by annealing is found to abstract hydrogen from the parent ester at an ..cap alpha..-carbon site, R'.+ R''CH/sub 2/CO/sub 2/R' ..-->.. R''CHCO/sub 2/R', or in the case of ethyl formate from the formate hydrogen, CH/sub 3/CH/sub 2/.+ HCO/sub 2/C/sub 2/H/sub 5/ ..-->.. C/sub 2/H/sub 6/ +.CO/sub 2/C/submore » 2/H/sub 5/. Results found for the methyl formate anion suggest hydrogen abstraction by the anion itself may compete with alkyl radical formation. The anion of the triglyceride triacetin is found to undergo an analogous mechanism to the ester anions producing the propane diol diester radical, .CH/sub 2/CH(Ac)CH/sub 2/(Ac), Ac = acetate. This species subsequently abstracts hydrogen from the parent compound to produce the ..cap alpha..-carbon radical, .CH/sub 2/CO/sub 2/R. Results found after annealing the tripropionin radical anion give evidence for abstraction from the ..cap alpha.. carbon in the propionate side groups producing CH/sub 3/CHCO/sub 2/R. Studies of a ..gamma..-irradiated ester (ethyl myristate) and two triglycerides (tripalmitin and tristearin) yield results which suggest that the mechanism of ester anion decay found in aqueous glasses applies to ..gamma..-irradiated neat long-chain esters and triglycerides. Results found in this work are compared to the results of product analysis.« less

Quantitative analysis of anti-inflammatory and radical scavenging triterpenoid esters in evening primrose seeds.

PubMed

Zaugg, Janine; Potterat, Olivier; Plescher, Andreas; Honermeier, Bernd; Hamburger, Matthias

2006-09-06

Lipophilic triterpenoidal esters with radical scavenging and cyclooxygenase inhibitory properties were recently found in cold-pressed, nonraffinated evening primrose oil (EPO). A quantitative assay for the analysis of 3-O-trans-caffeoyl derivatives of betulinic, morolic, and oleanolic acid in evening primrose seeds was developed and validated. Extraction efficiency >99% was achieved by means of pressurized liquid extraction with two extraction cycles and 80% (v/v) ethanol at 120 degrees C. Analysis of esters was by normal-phase high-performance liquid chromatography on a Diol column and hexane/ethyl acetate (containing 0.1% formic acid) (65:35) as the eluent. The analytes were determined without further prepurification. Seeds from defined cultures of Oenothera biennis, Oenothera lamarckiana, and Oenothera ammophila, grown under identical conditions, were analyzed. The cultures originated from seeds from eight collections in the wild and from selections from five cultivars. The content of total triterpenoidal esters in seeds varied between 1.34 and 2.78 mg/g. Three types of qualitative patterns were observed for the triterpenoidal esters. The influence of different harvest times and plant treatments was studied with the cultivar Anothera. Variations between 1.5 and 2.3 mg/g were found.

Acidic electrolyzed water efficiently improves the flavour of persimmon (Diospyros kaki L. cv. Mopan) wine.

PubMed

Zhu, Wanqi; Zhu, Baoqing; Li, Yao; Zhang, Yanyan; Zhang, Bolin; Fan, Junfeng

2016-04-15

The ability of acidic (AcW) and alkaline electrolyzed waters (AlW) to improve the flavour of persimmon (Diospyros kaki L.) wine was evaluated. Wines made with AcW (WAcW) were significantly better than wines made with AlW or pure water (PW) in aroma, taste, and colour. Volatile analysis showed that WAcW has high alcohol and ester contents, including 2-phenylethanol, isopentanol, isobutanol, ethyl dodecanoate, phenethyl acetate, and butanedioic acid diethyl ester. The total amino acid content of persimmon slurry soaked with AcW reached 531.2 mg/l, which was much higher than those of the slurries soaked in AlW (381.3 mg/l) and PW (182.7 mg/l). The composition of major amino acids in the AcW-soaked slurry may contribute to the strong ester flavour of WAcW. This is the first report to suggest that electrolyzed functional water (EFW) can be used to improve wine flavour, leading to the possible use of EFW in food processing. Copyright © 2015 Elsevier Ltd. All rights reserved.

Amino Acid and Peptide Immobilization on Oxidized Nanocellulose: Spectroscopic Characterization

PubMed Central

Barazzouk, Saïd; Daneault, Claude

2012-01-01

In this work, oxidized nanocellulose (ONC) was synthesized and chemically coupled with amino acids and peptides using a two step coupling method at room temperature. First, ONC was activated by N-ethyl-N’-(3-dimethylaminopropyl) carbodiimide hydrochloride, forming a stable active ester in the presence of N-hydroxysuccinimide. Second, the active ester was reacted with the amino group of the amino acid or peptide, forming an amide bond between ONC and the grafted molecule. Using this method, the intermolecular interaction of amino acids and peptides was avoided and uniform coupling of these molecules on ONC was achieved. The coupling reaction was very fast in mild conditions and without alteration of the polysaccharide. The coupling products (ONC-amino acids and ONC-peptides) were characterized by transmission electron microscopy and by the absorption, emission, Fourier transform infrared spectroscopy (FTIR) and X-ray photoelectron spectroscopy (XPS) spectroscopic techniques. PMID:28348303

40 CFR 721.8450 - 2-Propenoic acid, 2-methyl-, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl ester.

Code of Federal Regulations, 2010 CFR

2010-07-01

..., and consumer activities. Requirements as specified in § 721.80 (l) and (q). (iv) Release to water...)(4), if the waste stream containing the PMN substance will be treated using biological treatment (activated sludge or equivalent) plus clarification, then the amount of PMN substance reasonably likely to be...

Synthesis, spectral characterization, thermal behaviour, antibacterial activity and DFT calculation on N‧-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide and N‧-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester

NASA Astrophysics Data System (ADS)

Bharty, M. K.; Dani, R. K.; Kushawaha, S. K.; Prakash, Om; Singh, Ranjan K.; Sharma, V. K.; Kharwar, R. N.; Singh, N. K.

2015-06-01

Two new compounds N‧-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide {Hbmshb (1)} and N‧-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester {H2mbhce (2)} have been synthesized and characterized with the aid of elemental analyses, IR, NMR and single crystal X-ray diffraction data. Compounds 1 and 2 crystallize in orthorhombic and monoclinic systems with space group Pna21 and P21/n, respectively. Inter and intra molecular hydrogen bonding link two molecules and provide linear chain structure. In addition to this, compound 2 is stabilized by CH⋯π and NH⋯π interactions. Molecular geometry from X-ray analysis, geometry optimization, charge distribution, bond analysis, frontier molecular orbital (FMO) analysis and non-linear optical (NLO) effects have been performed using the density functional theory (DFT) with the B3LYP functional. The bioefficacy of compounds has been examined against the growth of bacteria to evaluate their anti-microbial potential. Compounds 1 and 2 are thermally stable and show NLO behaviour better than the urea crystal.

Deuterium Exchange in Ethyl Acetoacetate: An Undergraduate GC-MS [Gas Chromatography-Mass Spectroscopy] Experiment

ERIC Educational Resources Information Center

Heinson, C. D.; Williams, J. M.; Tinnerman, W. N.; Malloy, T. B.

2005-01-01

The role of ethanol O-d in nullifying the deuterolysis may be demonstrated by determining that transesterification of methyl acetoacetate of the ethyl ester occurs as well as deuterium exchange of the five acetoacetate hydrogens. The significant acidity of the methylene protons in the acetoacetate group, the efficacy of base catalysis, the role of…

Plasma Phosphatidylethanolamine and Triacylglycerol Fatty Acid Concentrations are Altered in Major Depressive Disorder Patients with Seasonal Pattern.

PubMed

Otoki, Yurika; Hennebelle, Marie; Levitt, Anthony J; Nakagawa, Kiyotaka; Swardfager, Walter; Taha, Ameer Y

2017-06-01

Disturbances in peripheral and brain lipid metabolism, including the omega-3 fatty acid docosahexaenoic acid (DHA), have been reported in major depressive disorder (MDD). However, these changes have yet to be confirmed in MDD with seasonal pattern (MDD-s), a subtype of recurrent MDD. The present exploratory study quantified plasma plasmalogen and diacyl-phospholipid species, and fatty acids within total phospholipids, cholesteryl esters, triacylglycerols and free fatty acids in non-medicated MDD-s participants (n = 9) during euthymia in summer or fall, and during depression in winter in order to screen for potential high sensitivity lipid biomarkers. Triacylglycerol alpha-linolenic acid concentration was significantly decreased, and myristoleic acid concentration was significantly increased, during winter depression compared to summer-fall euthymia. 1-stearyl-2-docosahexaenoyl-sn-glycero-3-phosphoethanolamine, a diacyl-phospholipid containing stearic acid and DHA, was significantly decreased in winter depression. Concentrations of cholesteryl ester oleic acid and several polyunsaturated fatty acids between summer/fall and winter increased in proportion to the increase in depressive symptoms. The observed changes in lipid metabolic pathways in winter-type MDD-s offer new promise for lipid biomarker development.

Fermentative behavior of Saccharomyces strains during microvinification of raspberry juice (Rubus idaeus L.).

PubMed

Duarte, Whasley F; Dragone, Giuliano; Dias, Disney R; Oliveira, José M; Teixeira, José A; Silva, João B Almeida E; Schwan, Rosane F

2010-10-15

Sixteen different strains of Saccharomyces cerevisiae and Saccharomyces bayanus were evaluated in the production of raspberry fruit wine. Raspberry juice sugar concentrations were adjusted to 16° Brix with a sucrose solution, and batch fermentations were performed at 22 °C. Various kinetic parameters, such as the conversion factors of the substrates into ethanol (Y(p/s)), biomass (Y(x/s)), glycerol (Y(g/s)) and acetic acid (Y(ac/s)), the volumetric productivity of ethanol (Q(p)), the biomass productivity (P(x)), and the fermentation efficiency (E(f)) were calculated. Volatile compounds (alcohols, ethyl esters, acetates of higher alcohols and volatile fatty acids) were determined by gas chromatography (GC-FID). The highest values for the E(f), Y(p/s), Y(g/s), and Y(x/s) parameters were obtained when strains commonly used in the fuel ethanol industry (S. cerevisiae PE-2, BG, SA, CAT-1, and VR-1) were used to ferment raspberry juice. S. cerevisiae strain UFLA FW 15, isolated from fruit, displayed similar results. Twenty-one volatile compounds were identified in raspberry wines. The highest concentrations of total volatile compounds were found in wines produced with S. cerevisiae strains UFLA FW 15 (87,435 μg/L), CAT-1 (80,317.01 μg/L), VR-1 (67,573.99 μg/L) and S. bayanus CBS 1505 (71,660.32 μg/L). The highest concentrations of ethyl esters were 454.33 μg/L, 440.33 μg/L and 438 μg/L for S. cerevisiae strains UFLA FW 15, VR-1 and BG, respectively. Similar to concentrations of ethyl esters, the highest concentrations of acetates (1927.67 μg/L) and higher alcohols (83,996.33 μg/L) were produced in raspberry wine from S. cerevisiae UFLA FW 15. The maximum concentration of volatile fatty acids was found in raspberry wine produced by S. cerevisiae strain VR-1. We conclude that S. cerevisiae strain UFLA FW 15 fermented raspberry juice and produced a fruit wine with low concentrations of acids and high concentrations of acetates, higher alcohols and ethyl esters. Copyright © 2010 Elsevier B.V. All rights reserved.

40 CFR 721.10243 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, bis(2-chloroethyl) ester.

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Phosphonic acid, P-[2-[bis(2... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10243 Phosphonic acid, P-[2-[bis(2... to reporting. (1) The chemical substance identified as phosphonic acid, P-[2-[bis(2-hydroxyethyl...

40 CFR 721.10243 - Phosphonic acid, P-[2-[bis(2-hydroxyethyl)amino]ethyl]-, bis(2-chloroethyl) ester.

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Phosphonic acid, P-[2-[bis(2... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10243 Phosphonic acid, P-[2-[bis(2... to reporting. (1) The chemical substance identified as phosphonic acid, P-[2-[bis(2-hydroxyethyl...

3- and 4-pyridylalkyl adamantanecarboxylates: inhibitors of human cytochrome P450(17 alpha) (17 alpha-hydroxylase/C17,20-lyase). Potential nonsteroidal agents for the treatment of prostatic cancer.

PubMed

Chan, F C; Potter, G A; Barrie, S E; Haynes, B P; Rowlands, M G; Houghton, J; Jarman, M

1996-08-16

Various 3- and 4-pyridylalkyl 1-adamantanecarboxylates have been synthesized and tested for inhibitory activity toward the 17 alpha-hydroxylase and C17,20-lyase activities of human testicular cytochrome P450(17 alpha). The 4-pyridylalkyl esters were much more inhibitory than their 3-pyridylalkyl counterparts. The most potent was (S)-1-(4-pyridyl)ethyl 1-adamantanecarboxylate (3b; IC50 for lyase, 1.8 nM), whereas the (R)-enantiomer 3a was much less inhibitory (IC50 74 nM). Nearly as potent as 3b was the dimethylated counterpart, the 2-(4-pyridylpropan-2-yl) ester 5 (IC50 2.7 nM), which was also more resistant to degradation by esterases. In contrast to their 4-pyridyl analogs, the enantiomers of the 1-(3-pyridyl)ethyl ester were similarly inhibitory (IC50 for lyase; (R)-isomer 8a 150 nM, (S)-isomer 8b 230 nM). Amides corresponding to the 4-pyridylmethyl ester 1 and the (S)-1-(4-pyridyl)ethyl ester 3b, respectively 11 and 15b, were much less inhibitory than their ester counterparts. On the basis of a combination of inhibitory potency and resistance to esterases, the ester 5 was the best candidate for further development as a potential nonsteroidal inhibitor of cytochrome P450(17 alpha) for the treatment of prostate cancer.

Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6-[{sup 18}F]fluoro-1-dopa

DOE Office of Scientific and Technical Information (OSTI.GOV)

Satyamurthy, N.; Barrio, J.R.; Bishop, A.J.

A process is revealed for forming a 6-fluoro derivative of compounds in the L-Dopa family comprising the steps of protecting the groups attached to the benzene ring in the compound followed by serially reacting the protected compound with (a) iodine and silver trifluoroacetic acid; (b) Bb{sub 3}; (c) dit-butyldicarbonate; (d) hexamethyltin; (e) a fluoro compound; (f) hydrobromic acid; and (g) raising the pH to {<=}7. 1 fig.

Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6-[{sup 18}F]fluoro-1-dopa

DOEpatents

Satyamurthy, N.; Barrio, J.R.; Bishop, A.J.; Namavari, M.; Bida, G.T.

1996-04-23

A process is revealed for forming a 6-fluoro derivative of compounds in the L-Dopa family comprising the steps of protecting the groups attached to the benzene ring in the compound followed by serially reacting the protected compound with (a) iodine and silver trifluoroacetic acid; (b) Bb{sub 3}; (c) dit-butyldicarbonate; (d) hexamethyltin; (e) a fluoro compound; (f) hydrobromic acid; and (g) raising the pH to {<=}7. 1 fig.

Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6-(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6- .sup.18 F!fluoro-1-dopa

DOEpatents

Satyamurthy, Nagichettiar; Barrio, Jorge R.; Bishop, Allyson J.; Namavari, Mohammad; Bida, Gerald T.

1996-01-01

A process for forming a 6-fluoro derivative of compounds in the L-Dopa family comprising the steps of protecting the groups attached to the benzene ring in the compound followed by serially reacting the protected compound with (a) iodine and silver trifluoroacetic acid; (b) Bb.sub.3 ; (c) dit-butyldicarbonate; (d) hexamethyltin; (e) a fluoro compound; (f) hydrobromic acid; and (g) raising the pH to .ltoreq.7.

[Studies on chemical constituents from seeds of Euryale ferox].

PubMed

Sun, Hai-lin; Zhang, Ya-qiong; Xie, Xiao-yan; Che, Yan-yun

2014-11-01

To study the chemical constituents from the seeds of Euryale ferox. The chemical constituents were isolated by silica gel column, Sephadex LH-20 and their structures were identified by physico-chemical and spectral analysis. Seven compounds were purified from the 95% ethanol extract. These constituents were elucidated as protocatechuic acid (1), gallic acid (2), gallic acid ethyl ester(3),5 ,7-dihydroxychromone(4), β-sitosterol(5), daucosterol(6), and 5,7-dihydroxy-6,4'-dimethoxyflavone(7), respectively. All compounds are isolated from this plant for the first time.

Characterization of Shrimp Oil from Pandalus borealis by High Performance Liquid Chromatography and High Resolution Mass Spectrometry.

PubMed

Jiao, Guangling; Hui, Joseph P M; Burton, Ian W; Thibault, Marie-Hélène; Pelletier, Claude; Boudreau, Josée; Tchoukanova, Nadia; Subramanian, Balaji; Djaoued, Yahia; Ewart, Stephen; Gagnon, Jacques; Ewart, Kathryn Vanya; Zhang, Junzeng

2015-06-18

Northern shrimp (Pandalus borealis) oil, which is rich in omega-3 fatty acids, was recovered from the cooking water of shrimp processing facilities. The oil contains significant amounts of omega-3 fatty acids in triglyceride form, along with substantial long-chain monounsaturated fatty acids (MUFAs). It also features natural isomeric forms of astaxanthin, a nutritional carotenoid, which gives the oil a brilliant red color. As part of our efforts in developing value added products from waste streams of the seafood processing industry, we present in this paper a comprehensive characterization of the triacylglycerols (TAGs) and astaxanthin esters that predominate in the shrimp oil by using HPLC-HRMS and MS/MS, as well as 13C-NMR. This approach, in combination with FAME analysis, offers direct characterization of fatty acid molecules in their intact forms, including the distribution of regioisomers in TAGs. The information is important for the standardization and quality control, as well as for differentiation of composition features of shrimp oil, which could be sold as an ingredient in health supplements and functional foods.

Characterization of Shrimp Oil from Pandalus borealis by High Performance Liquid Chromatography and High Resolution Mass Spectrometry

PubMed Central

Jiao, Guangling; Hui, Joseph P. M.; Burton, Ian W.; Thibault, Marie-Hélène; Pelletier, Claude; Boudreau, Josée; Tchoukanova, Nadia; Subramanian, Balaji; Djaoued, Yahia; Ewart, Stephen; Gagnon, Jacques; Ewart, Kathryn Vanya; Zhang, Junzeng

2015-01-01

Northern shrimp (Pandalus borealis) oil, which is rich in omega-3 fatty acids, was recovered from the cooking water of shrimp processing facilities. The oil contains significant amounts of omega-3 fatty acids in triglyceride form, along with substantial long-chain monounsaturated fatty acids (MUFAs). It also features natural isomeric forms of astaxanthin, a nutritional carotenoid, which gives the oil a brilliant red color. As part of our efforts in developing value added products from waste streams of the seafood processing industry, we present in this paper a comprehensive characterization of the triacylglycerols (TAGs) and astaxanthin esters that predominate in the shrimp oil by using HPLC-HRMS and MS/MS, as well as 13C-NMR. This approach, in combination with FAME analysis, offers direct characterization of fatty acid molecules in their intact forms, including the distribution of regioisomers in TAGs. The information is important for the standardization and quality control, as well as for differentiation of composition features of shrimp oil, which could be sold as an ingredient in health supplements and functional foods. PMID:26096274

Fatty acid ethyl ester concentrations in hair and self-reported alcohol consumption in 644 cases from different origin.

PubMed

Süsse, Silke; Selavka, Carl M; Mieczkowski, Tom; Pragst, Fritz

2010-03-20

For diagnosis of chronic alcohol abuse, fatty acid ethyl esters (FAEE) were determined in hair samples from 644 individuals, mainly parents from child protection cases. The analysis for ethyl myristate, ethyl palmitate, ethyl oleate and ethyl stearate was performed according to a validated procedure consisting of external degreasing by two times washing with n-heptane, extraction with a mixture of dimethylsulfoxide and n-heptane, separation and evaporation of the n-heptane layer, headspace solid phase microextraction of the residue after addition of phosphate buffer pH 7.6 and gas chromatography-mass spectrometry using deuterated internal standards. For interpretation, the sum of the concentrations of the four esters C(FAEE) was used with the cut-off's 0.5 ng/mg for the proximal scalp hair segment 0-3 cm or less and 1.0 ng/mg for scalp hair samples with a length between 3 and 6 cm and for body hair. C(FAEE) ranged from 0.11 to 31 ng/mg (mean 1.77 ng/mg, median 0.82 ng/mg). The mean concentration ratio between the 4 esters was 8:45:38:9. 298 cases had C(FAEE) above the cut-off's. Self-reported drinking data were obtained in 553 of the cases in the categories abstinent (156 cases), moderate drinking (252 cases) and excessive drinking (145 cases). Median and box-plot data clearly demonstrate differentiation of these ingestor sub-populations by C(FAEE). However, in the abstinent and moderate groups the consumption was frequently underreported (37 and 110 cases positive) whereas in the group self-reported excessive drinking 32 cases were negative. Comparison of C(FAEE) with carbohydrate-deficient transferrin (CDT) in 139 cases and gamma-glutamyltransferase (GGT) in 136 cases showed a good agreement in CDT- and GGT positive cases (27/28 and 32/41) but a large portion of the negative CDT- and GGT-results with positive hair test (44/100 and 48/95) which is explained mainly by the much shorter time window of CDT and GGT. No significant correlation was found between persons weight and C(FAEE) showing that the test is not biased against physical fitness or obesity. Furthermore, there was no statistically significant difference between scalp hair (541 samples) and hair from other body sites (84 samples). In conclusion, FAEE in hair appeared to be suitable markers for the detection of excessive drinking. However, as there is no proportionality between drinking amount and C(FAEE), the additional use of other markers can increase the reliability of the interpretation. Copyright 2009 Elsevier Ireland Ltd. All rights reserved.

Optimization of one-step in situ transesterification method for accurate quantification of EPA in Nannochloropsis gaditana

DOE PAGES

Tang, Yuting; Zhang, Yue; Rosenberg, Julian N.; ...

2016-11-08

Microalgae are a valuable source of lipid feedstocks for biodiesel and valuable omega-3 fatty acids. Nannochloropsis gaditana has emerged as a promising producer of eicosapentaenoic acid (EPA) due to its fast growth rate and high EPA content. In the present study, the fatty acid profile of Nannochloropsis gaditana was found to be naturally high in EPA and devoid of docosahexaenoic acid (DHA), thereby providing an opportunity to maximize the efficacy of EPA production. Using an optimized one-step in situ transesterification method (methanol:biomass = 90 mL/g; HCl 5% by vol.; 70 °C; 1.5 h), the maximum fatty acid methyl ester (FAME)more » yield of Nannochloropsis gaditana cultivated under rich condition was quantified as 10.04% ± 0.08% by weight with EPA-yields as high as 4.02% ± 0.17% based on dry biomass. The total FAME and EPA yields were 1.58- and 1.23-fold higher separately than that obtained using conventional two-step method (solvent system: methanol and chloroform). Furthermore, this one-step in situ method provides a fast and simple method to measure fatty acid methyl ester (FAME) yields and could serve as a promising method to generate eicosapentaenoic acid methyl ester from microalgae.« less

Optimization of one-step in situ transesterification method for accurate quantification of EPA in Nannochloropsis gaditana

DOE Office of Scientific and Technical Information (OSTI.GOV)

Tang, Yuting; Zhang, Yue; Rosenberg, Julian N.

Microalgae are a valuable source of lipid feedstocks for biodiesel and valuable omega-3 fatty acids. Nannochloropsis gaditana has emerged as a promising producer of eicosapentaenoic acid (EPA) due to its fast growth rate and high EPA content. In the present study, the fatty acid profile of Nannochloropsis gaditana was found to be naturally high in EPA and devoid of docosahexaenoic acid (DHA), thereby providing an opportunity to maximize the efficacy of EPA production. Using an optimized one-step in situ transesterification method (methanol:biomass = 90 mL/g; HCl 5% by vol.; 70 °C; 1.5 h), the maximum fatty acid methyl ester (FAME)more » yield of Nannochloropsis gaditana cultivated under rich condition was quantified as 10.04% ± 0.08% by weight with EPA-yields as high as 4.02% ± 0.17% based on dry biomass. The total FAME and EPA yields were 1.58- and 1.23-fold higher separately than that obtained using conventional two-step method (solvent system: methanol and chloroform). Furthermore, this one-step in situ method provides a fast and simple method to measure fatty acid methyl ester (FAME) yields and could serve as a promising method to generate eicosapentaenoic acid methyl ester from microalgae.« less

In-tube extraction and GC-MS analysis of volatile components from wild and cultivated sea buckthorn (Hippophae rhamnoides L. ssp. Carpatica) berry varieties and juice.

PubMed

Socaci, Sonia A; Socaciu, Carmen; Tofană, Maria; Raţi, Ioan V; Pintea, Adela

2013-01-01

The health benefits of sea buckthorn (Hippophae rhamnoides L.) are well documented due to its rich content in bioactive phytochemicals (pigments, phenolics and vitamins) as well as volatiles responsible for specific flavours and bacteriostatic action. The volatile compounds are good biomarkers of berry freshness, quality and authenticity. To develop a fast and efficient GC-MS method including a minimal sample preparation technique (in-tube extraction, ITEX) for the discrimination of sea buckthorn varieties based on their chromatographic volatile fingerprint. Twelve sea buckthorn varieties (wild and cultivated) were collected from forestry departments and experimental fields, respectively. The extraction of volatile compounds was performed using the ITEX technique whereas separation and identification was performed using a GC-MS QP-2010. Principal component analysis (PCA) was applied to discriminate the differences among sample composition. Using GC-MS analysis, from the headspace of sea buckthorn samples, 46 volatile compounds were separated with 43 being identified. The most abundant derivatives were ethyl esters of 2-methylbutanoic acid, 3-methylbutanoic acid, hexanoic acid, octanoic acid and butanoic acid, as well as 3-methylbutyl 3-methylbutanoate, 3-methylbutyl 2-methylbutanoate and benzoic acid ethyl ester (over 80% of all volatile compounds). Principal component analysis showed that the first two components explain 79% of data variance, demonstrating a good discrimination between samples. A reliable, fast and eco-friendly ITEX/GC-MS method was applied to fingerprint the volatile profile and to discriminate between wild and cultivated sea buckthorn berries originating from the Carpathians, with relevance to food science and technology. Copyright © 2013 John Wiley & Sons, Ltd.

Corrosion-Related Consequences of Biodiesel in Contact with Natural Seawater

DTIC Science & Technology

2010-03-01

petroleum diesel, biodiesel contains no sulfur. In the U.S. the term “biodiesel” is standardized as fatty acid methyl ester ( FAME ). Biodiesel content is...Form 298 (Rev. 8-98) Prescribed by ANSI Std Z39-18 to methyl (or ethyl) esters with a process known as transesterification.4 The transesterification...biodegradation of the vegetable methyl esters in agitated San Francisco Bay water was less than 4 days at 17 °C.4,22 The highest corrosion rates

Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran.

PubMed

Wang, Wei; Guo, Jia; Zhang, Junnan; Peng, Jie; Liu, Tianxing; Xin, Zhihong

2015-03-15

The bound phenolic compounds in rice bran were released and extracted with ethyl acetate based on alkaline digestion. An investigation of the chemical constituents of EtOAc extract has led to the isolation of a new compound, para-hydroxy methyl benzoate glucoside (8), together with nine known compounds, cycloeucalenol cis-ferulate (1), cycloeucalenol trans-ferulate (2), trans-ferulic acid (3), trans-ferulic acid methyl ester (4), cis-ferulic acid (5), cis-ferulic acid methyl ester (6), methyl caffeate (7), vanillic aldehyde (9) and para-hydroxy benzaldehyde (10). The structures of these compounds were determined using a combination of spectroscopic methods and chemical analysis. Among the compounds isolated, compound 3, 5 and 7 exhibited strong DPPH and ABTS(+) radical scavenging activities, followed by compounds 4 and 6. Compound 1 and 2 showed potent DPPH and ABTS(+) radical scavenging activities, compound 8 displayed moderate antioxidant activity against ABTS(+) radical, whereas compound 9 and 10 showed weak antioxidant activity. Copyright © 2014 Elsevier Ltd. All rights reserved.

Protective effects of prescription n-3 fatty acids against impairment of spatial cognitive learning ability in amyloid β-infused rats.

PubMed

Hashimoto, Michio; Tozawa, Ryuichi; Katakura, Masanori; Shahdat, Hossain; Haque, Abdul Md; Tanabe, Yoko; Gamoh, Shuji; Shido, Osamu

2011-07-01

Deposition of amyloid β peptide (Aβ) into the brain causes cognitive impairment. We investigated whether prescription pre-administration of n-3 fatty acids improves cognitive learning ability in young rats and whether it protects against learning ability impairments in an animal model of Alzheimer's disease that was prepared by infusion of Aβ(1-40) into the cerebral ventricles of rats. Pre-administration of TAK-085 (highly purified and concentrated n-3 fatty acids containing eicosapentaenoic acid ethyl ester and docosahexaenoic acid ethyl ester) at 300 mg kg(-1) day(-1) for 12 weeks significantly reduced the number of reference memory errors in an 8-arm radial maze, suggesting that long-term administration of TAK-085 improves cognitive leaning ability in rats. After pre-administration, the control group was divided into the vehicle and Aβ-infused groups, whereas the TAK-085 pre-administration group was divided into the TAK-085 and TAK-085 + Aβ groups (TAK-085-pre-administered Aβ-infused rats). Aβ(1-40) or vehicle was infused into the cerebral ventricle using a mini osmotic pump. Pre-administration of TAK-085 to the Aβ-infused rats significantly suppressed the number of reference and working memory errors and decreased the levels of lipid peroxide and reactive oxygen species in the cerebral cortex and hippocampus of Aβ-infused rats, suggesting that TAK-085 increases antioxidative defenses. The present study suggests that long-term administration of TAK-085 is a possible therapeutic agent for protecting against Alzheimer's disease-induced learning deficiencies. This journal is © The Royal Society of Chemistry 2011

Keloids in rural black South Africans. Part 2: dietary fatty acid intake and total phospholipid fatty acid profile in the blood of keloid patients.

PubMed

Louw, L; Dannhauser, A

2000-11-01

In the second part of this study, emphasis is placed on nutritional intakes (fatty acids and micronutrients) and fatty acid intake and metabolism in the blood, respectively, according to a combined 24 h recall and standardized food frequency questionnaire analyses of keloid prone patients (n=10), compared with normal black South Africans (n=80), and total phospholipid blood (plasma and red blood cell ) analyses of keloid patients (n=20), compared with normal individuals (n=20). Lipid extraction and fractionation by standard procedures, total phospholipid (TPL) separation with thin layer chromatography, and fatty acid methyl ester analyses with gas liquid chromatography techniques were used. Since nutrition may play a role in several disease disorders, the purpose of this study was to confirm or refute a role for essential fatty acids (EFAs) in the hypothesis of keloid formations stated in part 1 of this study. (1)According to the Canadian recommendation (1991), we observed that in keloid patients linoleic acid (LA) and arachidonic acid (AA) dietary intakes, as EFAs of the omega-6-series, are higher than the recommended 7-11 g/d. However, the a-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) dietary intakes, as EFAs of the omega-3 series, are lower than the recommendation of 1.1-1.5 g/d. This was also the case in the control group, where a higher dietary intake of the omega-6 fatty acids and a slightly lower dietary intake of the omega-3 fatty acids occurred. Thus, we confirm a high dietary intake of LA (as a product of organ meats, diary products and many vegetable oils) and AA (as a product of meats and egg yolks), as well as lower dietary intakes of ALA (as a product of grains, green leafy vegetables, soy oil, rapeseed oil and linseed), and EPA and DHA (as products of marine oils). Lower micronutrient intakes than the recommended dietary allowances were observed in the keloid group that may influence EFA metabolism and/or collagen synthesis. Of cardinal importance may be the lower intake of calcium in the keloid patients that may contribute to abnormal cell signal transduction in fibroblasts and consequent collagen overproduction, and the lower copper intake that may influence the immune system, or perhaps even the high magnesium intake that stimulates metabolic activity. Micronutrient deficiencies also occurred in the diets of the normal black South Africans that served as a control group. In the case of plasma TPLs, deficiency of the omega-3 EFA series (ALA, EPA and DHA) occurred, and this is in accordance with the apparent lower omega-3 EFA intake in the diets of these patients. In the case of the red blood cell TPLs, as a true and reliable source of dietary fatty acid intake and metabolism, sufficient EFAs of the omega-6 series (LA and AA) and the omega-3 series (ALA, EPA and DHA) occurred. For this study group a relative deficiency of nutritional omega-3 EFA intake apparently did occur, but was probably compensated for by blood fatty acid metabolism. Copyright 2000 Harcourt Publishers Ltd.

Impact of biodiesel source material and chemical structure on emissions of criteria pollutants from a heavy-duty engine.

PubMed

McCormick, R L; Graboski, M S; Alleman, T L; Herring, A M; Tyson, K S

2001-05-01

Biodiesel is an oxygenated diesel fuel made from vegetable oils and animal fats by conversion of the triglyceride fats to esters via transesterification. In this study we examined biodiesels produced from a variety of real-world feedstocks as well as pure (technical grade) fatty acid methyl and ethyl esters for emissions performance in a heavy-duty truck engine. The objective was to understand the impact of biodiesel chemical structure, specifically fatty acid chain length and number of double bonds, on emissions of NOx and particulate matter (PM). A group of seven biodiesels produced from real-world feedstocks and 14 produced from pure fatty acids were tested in a heavy-duty truck engine using the U.S. heavy-duty federal test procedure (transient test). It was found that the molecular structure of biodiesel can have a substantial impact on emissions. The properties of density, cetane number, and iodine number were found to be highly correlated with one another. For neat biodiesels, PM emissions were essentially constant at about 0.07 g/bhp-h for all biodiesels as long as density was less than 0.89 g/cm3 or cetane number was greater than about 45. NOx emissions increased with increasing fuel density or decreasing fuel cetane number. Increasing the number of double bonds, quantified as iodine number, correlated with increasing emissions of NOx. Thus the increased NOx observed for some fuels cannot be explained by the NOx/PM tradeoff and is therefore not driven by thermal NO formation. For fully saturated fatty acid chains the NOx emission increased with decreasing chain length for tests using 18, 16, and 12 carbon chain molecules. Additionally, there was no significant difference in NOx or PM emissions for the methyl and ethyl esters of identical fatty acids.

Selective Enrichment of Omega-3 Fatty Acids in Oils by Phospholipase A1

PubMed Central

Puri, Munish; Barrow, Colin; Rao, Nalam Madhusudhana

2016-01-01

Omega fatty acids are recognized as key nutrients for healthier ageing. Lipases are used to release ω-3 fatty acids from oils for preparing enriched ω-3 fatty acid supplements. However, use of lipases in enrichment of ω-3 fatty acids is limited due to their insufficient specificity for ω-3 fatty acids. In this study use of phospholipase A1 (PLA1), which possesses both sn-1 specific activity on phospholipids and lipase activity, was explored for hydrolysis of ω-3 fatty acids from anchovy oil. Substrate specificity of PLA1 from Thermomyces lenuginosus was initially tested with synthetic p-nitrophenyl esters along with a lipase from Bacillus subtilis (BSL), as a lipase control. Gas chromatographic characterization of the hydrolysate obtained upon treatment of anchovy oil with these enzymes indicated a selective retention of ω-3 fatty acids in the triglyceride fraction by PLA1 and not by BSL. 13C NMR spectroscopy based position analysis of fatty acids in enzyme treated and untreated samples indicated that PLA1 preferably retained ω-3 fatty acids in oil, while saturated fatty acids were hydrolysed irrespective of their position. Hydrolysis of structured triglyceride,1,3-dioleoyl-2-palmitoylglycerol, suggested that both the enzymes hydrolyse the fatty acids at both the positions. The observed discrimination against ω-3 fatty acids by PLA1 appears to be due to its fatty acid selectivity rather than positional specificity. These studies suggest that PLA1 could be used as a potential enzyme for selective concentrationof ω-3 fatty acids. PMID:26978518

Selective Enrichment of Omega-3 Fatty Acids in Oils by Phospholipase A1.

PubMed

Ranjan Moharana, Tushar; Byreddy, Avinesh R; Puri, Munish; Barrow, Colin; Rao, Nalam Madhusudhana

2016-01-01

Omega fatty acids are recognized as key nutrients for healthier ageing. Lipases are used to release ω-3 fatty acids from oils for preparing enriched ω-3 fatty acid supplements. However, use of lipases in enrichment of ω-3 fatty acids is limited due to their insufficient specificity for ω-3 fatty acids. In this study use of phospholipase A1 (PLA1), which possesses both sn-1 specific activity on phospholipids and lipase activity, was explored for hydrolysis of ω-3 fatty acids from anchovy oil. Substrate specificity of PLA1 from Thermomyces lenuginosus was initially tested with synthetic p-nitrophenyl esters along with a lipase from Bacillus subtilis (BSL), as a lipase control. Gas chromatographic characterization of the hydrolysate obtained upon treatment of anchovy oil with these enzymes indicated a selective retention of ω-3 fatty acids in the triglyceride fraction by PLA1 and not by BSL. 13C NMR spectroscopy based position analysis of fatty acids in enzyme treated and untreated samples indicated that PLA1 preferably retained ω-3 fatty acids in oil, while saturated fatty acids were hydrolysed irrespective of their position. Hydrolysis of structured triglyceride,1,3-dioleoyl-2-palmitoylglycerol, suggested that both the enzymes hydrolyse the fatty acids at both the positions. The observed discrimination against ω-3 fatty acids by PLA1 appears to be due to its fatty acid selectivity rather than positional specificity. These studies suggest that PLA1 could be used as a potential enzyme for selective concentrationof ω-3 fatty acids.

Semipurified Ethyl Acetate Partition of Methanolic Extract of Melastoma malabathricum Leaves Exerts Gastroprotective Activity Partly via Its Antioxidant-Antisecretory-Anti-Inflammatory Action and Synergistic Action of Several Flavonoid-Based Compounds

PubMed Central

Ismail Suhaimy, Noor Wahida; Noor Azmi, Ahmad Khusairi; Mohtarrudin, Norhafizah; Cheema, Manraj Singh

2017-01-01

Recent study has demonstrated the gastroprotective activity of crude methanolic extract of M. malabathricum leaves. The present study evaluated the gastroprotective potential of semipurified extracts (partitions): petroleum ether, ethyl acetate (EAMM), and aqueous obtained from the methanolic extract followed by the elucidation of the gastroprotective mechanisms of the most effective partition. Using the ethanol-induced gastric ulcer assay, all partitions exerted significant gastroprotection, with EAMM being the most effective partition. EAMM significantly (i) reduced the volume and acidity (free and total) while increasing the pH of gastric juice and enhanced the gastric wall mucus secretion when assessed using the pylorus ligation assay, (ii) increased the enzymatic and nonenzymatic antioxidant activity of the stomach tissue, (iii) lost its gastroprotective activity following pretreatment with N-omega-nitro-L-arginine methyl ester (L-NAME; NO blocker) or carbenoxolone (CBXN; NP-SH blocker), (iv) exerted antioxidant activity against various in vitro oxidation assays, and (v) showed moderate in vitro anti-inflammatory activity via the LOX-modulated pathway. In conclusion, EAMM exerts a remarkable NO/NP-SH-dependent gastroprotective effect that is attributed to its antisecretory and antioxidant activities, ability to stimulate the gastric mucus production and endogenous antioxidant system, and synergistic action of several gastroprotective-induced flavonoids. PMID:28168011

40 CFR 721.4250 - Hexanoic acid, 2-ethyl-, ethenyl ester.

Code of Federal Regulations, 2012 CFR

2012-07-01

... end of each work shift.), (a)(2)(ii) (With the exception of laboratory activities, full body chemical... by the proportion of each substance present in the total daily amount released. (b) Specific...

40 CFR 721.4250 - Hexanoic acid, 2-ethyl-, ethenyl ester.

Code of Federal Regulations, 2014 CFR

2014-07-01

... end of each work shift.), (a)(2)(ii) (With the exception of laboratory activities, full body chemical... by the proportion of each substance present in the total daily amount released. (b) Specific...

40 CFR 721.4250 - Hexanoic acid, 2-ethyl-, ethenyl ester.

Code of Federal Regulations, 2013 CFR

2013-07-01

... end of each work shift.), (a)(2)(ii) (With the exception of laboratory activities, full body chemical... by the proportion of each substance present in the total daily amount released. (b) Specific...

40 CFR 721.4250 - Hexanoic acid, 2-ethyl-, ethenyl ester.

Code of Federal Regulations, 2010 CFR

2010-07-01

... accordance with the most current version of the American Society for Testing and Materials (ASTM) F739... control technology does not apply. Instead, if the waste stream containing the substance will be treated...

40 CFR 721.4250 - Hexanoic acid, 2-ethyl-, ethenyl ester.

Code of Federal Regulations, 2011 CFR

2011-07-01

... accordance with the most current version of the American Society for Testing and Materials (ASTM) F739... control technology does not apply. Instead, if the waste stream containing the substance will be treated...

A highly bioavailable omega-3 free fatty acid formulation improves the cardiovascular risk profile in high-risk, statin-treated patients with residual hypertriglyceridemia (the ESPRIT trial).

PubMed

Maki, Kevin C; Orloff, David G; Nicholls, Stephen J; Dunbar, Richard L; Roth, Eli M; Curcio, Danielle; Johnson, Judith; Kling, Douglas; Davidson, Michael H

2013-09-01

A novel omega-3 formulation in free fatty acid form (OM3-FFA) has as much as 4-fold greater bioavailability than ethyl ester forms and reduces triglyceride (TG) levels in patients with severe hypertriglyceridemia. This study was designed to evaluate the efficacy of adding OM3-FFA (2 or 4 g/d) to statin therapy for lowering non-HDL-C and TG levels in subjects with persistent hypertriglyceridemia and at high risk for cardiovascular disease. In this double-blind, parallel-group study, 647 diet-stable patients with fasting TG levels ≥ 200 mg/dL and <500 mg/dL (treated with a maximally tolerated dose of statin or statin with ezetimibe) and at high risk for cardiovascular disease were randomized to 6 weeks of treatment with capsules of control (olive oil [OO]) 4 g/d, OM3-FFA 2 g/d (plus 2 g/d OO), or OM3-FFA 4 g/d. Assessments included fasting serum levels of lipids and apolipoproteins (apo); plasma concentrations of eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, and arachidonic acid; and laboratory safety values and adverse events. In the 627 subjects in the intention to treat sample, non-HDL-C levels were reduced with OM3-FFA 2 g/d and OM3-FFA 4 g/d (-3.9% and -6.9%, respectively) compared with OO (-0.9%) (both, P < 0.05), as were TG levels (-14.6% and -20.6%, respectively, vs -5.9%; both, P < 0.001). LDL-C levels increased with OM3-FFA 2 g/d (4.6%) compared with OO (1.1%) (P = 0.025) but not with OM3-FFA 4 g/d (1.3%). Total cholesterol and VLDL-C concentrations were reduced compared with OO with both OM3-FFA dosages, and the total cholesterol/HDL-C ratio and apo AI and apo B levels were significantly lowered with OM3-FFA 4 g/d only (all at least P < 0.05). Percent changes from baseline in HDL-C did not differ between OO and either OM3-FFA group. Plasma concentrations of docosahexaenoic acid, eicosapentaenoic acid, and docosapentaenoic acid were significantly increased and arachidonic acid was significantly reduced in both OM3-FFA treatment groups compared with the OO responses (all, P < 0.001). Withdrawals related to treatment-emergent adverse events ranged from 0.9% with OO to 3.2% with OM3-FFA 4 g/d. OM3-FFA was well tolerated and lowered non-HDL-C and TG levels at both 2- and 4-g/d dosages in patients with persistent hypertriglyceridemia taking a statin, with the 4-g/d dosage providing incremental improvements compared with 2 g/d. © 2013 Elsevier HS Journals, Inc. All rights reserved.

Influence of Production Method on the Chemical Composition, Foaming Properties, and Quality of Australian Carbonated and Sparkling White Wines.

PubMed

Culbert, Julie A; McRae, Jacqui M; Condé, Bruna C; Schmidtke, Leigh M; Nicholson, Emily L; Smith, Paul A; Howell, Kate S; Boss, Paul K; Wilkinson, Kerry L

2017-02-22

The chemical composition (protein, polysaccharide, amino acid, and fatty acid/ethyl ester content), foaming properties, and quality of 50 Australian sparkling white wines, representing the four key production methods, that is, Méthode Traditionelle (n = 20), transfer (n = 10), Charmat (n = 10), and carbonation (n = 10), were studied. Méthode Traditionelle wines were typically rated highest in quality and were higher in alcohol and protein contents, but lower in residual sugar and total phenolics, than other sparkling wines. They also exhibited higher foam volume and stability, which might be attributable to higher protein concentrations. Bottle-fermented Méthode Traditionelle and transfer wines contained greater proportions of yeast-derived mannoproteins, whereas Charmat and carbonated wines were higher in grape-derived rhamnogalacturonans; however, total polysaccharide concentrations were not significantly different between sparkling wine styles. Free amino acids were most abundant in carbonated wines, which likely reflects production via primary fermentation only and/or the inclusion of nontraditional grape varieties. Fatty acids and their esters were not correlated with foaming properties, but octanoic and decanoic acids and their ethyl esters were present in Charmat and carbonated wines at significantly higher concentrations than in bottle-fermented wines and were negatively correlated with quality ratings. Research findings provide industry with a better understanding of the compositional factors driving the style and quality of sparkling white wine.

Magnetoliposomes Loaded with Poly-Unsaturated Fatty Acids as Novel Theranostic Anti-Inflammatory Formulations

PubMed Central

Calle, Daniel; Negri, Viviana; Ballesteros, Paloma; Cerdán, Sebastián

2015-01-01

We describe the preparation, physico-chemical characterization and anti-inflammatory properties of liposomes containing the superparamagnetic nanoparticle Nanotex, the fluorescent dye Rhodamine-100 and omega-3 polyunsaturated fatty acid ethyl ester (ω-3 PUFA-EE), as theranostic anti-inflammatory agents. Liposomes were prepared after drying chloroform suspensions of egg phosphatidylcholine, hydration of the lipid film with aqueous phases containing or not Nanotex, Rhodamine-100 dye or ω-3 PUFA-EE, and eleven extrusion steps through nanometric membrane filters. This resulted in uniform preparations of liposomes of approximately 200 nm diameter. Extraliposomal contents were removed from the preparation by gel filtration chromatography. High Resolution Magic Angle Spinning 1H NMR Spectroscopy of the liposomal preparations containing ω-3 PUFA-EE revealed well resolved 1H resonances from highly mobile ω-3 PUFA-EE, suggesting the formation of very small (ca. 10 nm) ω-3 PUFA-EE nanogoticules, tumbling fast in the NMR timescale. Chloroform extraction of the liposomal preparations revealed additionally the incorporation of ω-3 PUFA-EE within the membrane domain. Water diffusion weighted spectra, indicated that the goticules of ω-3 PUFA-EE or its insertion in the membrane did not affect the average translational diffusion coefficient of water, suggesting an intraliposomal localization, that was confirmed by ultrafiltration. The therapeutic efficacy of these preparations was tested in two different models of inflammatory disease as inflammatory colitis or the inflammatory component associated to glioma development. Results indicate that the magnetoliposomes loaded with ω-3 PUFA-EE allowed MRI visualization in vivo and improved the outcome of inflammatory disease in both animal models, decreasing significantly colonic inflammation and delaying, or even reversing, glioma development. Together, our results indicate that magnetoliposomes loaded with ω-3 PUFA-EE may become useful anti-inflammatory agents for image guided drug delivery. PMID:25767616

Using Caenorhabditis elegans to Uncover Conserved Functions of Omega-3 and Omega-6 Fatty Acids

PubMed Central

Watts, Jennifer L.

2016-01-01

The nematode Caenorhabditis elegans is a powerful model organism to study functions of polyunsaturated fatty acids. The ability to alter fatty acid composition with genetic manipulation and dietary supplementation permits the dissection of the roles of omega-3 and omega-6 fatty acids in many biological process including reproduction, aging and neurobiology. Studies in C. elegans to date have mostly identified overlapping functions of 20-carbon omega-6 and omega-3 fatty acids in reproduction and in neurons, however, specific roles for either omega-3 or omega-6 fatty acids are beginning to emerge. Recent findings with importance to human health include the identification of a conserved Cox-independent prostaglandin synthesis pathway, critical functions for cytochrome P450 derivatives of polyunsaturated fatty acids, the requirements for omega-6 and omega-3 fatty acids in sensory neurons, and the importance of fatty acid desaturation for long lifespan. Furthermore, the ability of C. elegans to interconvert omega-6 to omega-3 fatty acids using the FAT-1 omega-3 desaturase has been exploited in mammalian studies and biotechnology approaches to generate mammals capable of exogenous generation of omega-3 fatty acids. PMID:26848697

Identification and biosynthesis of novel male specific esters in the wings of the tropical butterfly, Bicyclus martius sanaos.

PubMed

Wang, Hong-Lei; Brattström, Oskar; Brakefield, Paul M; Francke, Wittko; Löfstedt, Christer

2014-06-01

Representatives of the highly speciose tropical butterfly genus Bicyclus (Lepidoptera: Nymphalidae) are characterized by morphological differences in the male androconia, a set of scales and hair pencils located on the surface of the wings. These androconia are assumed to be associated with the release of courtship pheromones. In the present study, we report the identification and biosynthetic pathways of several novel esters from the wings of male B. martius sanaos. We found that the volatile compounds in this male butterfly were similar to female-produced moth sex pheromones. Components associated with the male wing androconial areas were identified as ethyl, isobutyl and 2-phenylethyl hexadecanoates and (11Z)-11-hexadecenoates, among which the latter are novel natural products. By topical application of deuterium-labelled fatty acid and amino acid precursors, we found these pheromone candidates to be produced in patches located on the forewings of the males. Deuterium labels from hexadecanoic acid were incorporated into (11Z)-11-hexadecenoic acid, providing experimental evidence of a Δ11-desaturase being active in butterflies. This unusual desaturase was found previously to be involved in the biosynthesis of female-produced sex pheromones of moths. In the male butterflies, both hexadecanoic acid and (11Z)-11-hexadecenoic acid were then enzymatically esterified to form the ethyl, isobutyl and 2-phenylethyl esters, incorporating ethanol, isobutanol, and 2-phenylethanol, derived from the corresponding amino acids L-alanine, L-valine, and L-phenylalanine.

Volatile profile of Madeira wines submitted to traditional accelerated ageing.

PubMed

Pereira, Vanda; Cacho, Juan; Marques, José C

2014-11-01

The evolution of monovarietal fortified Madeira wines forced-aged by traditional thermal processing (estufagem) were studied in terms of volatiles. SPE extracts were analysed by GC-MS before and after heating at 45 °C for 3 months (standard) and at 70 °C for 1 month (overheating). One hundred and ninety volatile compounds were identified, 53 of which were only encountered in baked wines. Most chemical families increased after standard heating, especially furans and esters, up to 61 and 3-fold, respectively. On the contrary, alcohols, acetates and fatty acids decreased after heating. Varietal aromas, such as Malvasia's monoterpenic alcohols were not detected after baking. The accelerated ageing favoured the development of some volatiles previously reported as typical aromas of finest Madeira wines, particularly phenylacetaldeyde, β-damascenone and 5-ethoxymethylfurfural. Additionally, ethyl butyrate, ethyl 2-methylbutyrate, ethyl caproate, ethyl isovalerate, guaiacol, 5-hydroxymethylfurfural and γ-decalactone were also found as potential contributors to the global aroma of baked wines. Copyright © 2014 Elsevier Ltd. All rights reserved.

Use of Torulaspora delbrueckii Co-fermentation With Two Saccharomyces cerevisiae Strains With Different Aromatic Characteristic to Improve the Diversity of Red Wine Aroma Profile

PubMed Central

Zhang, Bo-Qin; Luan, Yu; Duan, Chang-Qing; Yan, Guo-Liang

2018-01-01

The use of selected Saccharomyces and non-Saccharomyces strains as mixed starters has advantages over pure fermentation due to achieving wine products with distinctive and diversified aroma expected by consumers. To obtain a way to improve the aroma diversity and increase the differentiation of wine product, in this study, the aromatic effect of multi-culture of indigenous Torulaspora delbrueckii (TD12), simultaneous and sequential inoculation with two Saccharomyces strains (indigenous icewine yeast SC45 and commercial yeast BDX) with different enological characteristics were investigated in laboratory-scale 20 L fermenter, respectively. The results showed that T. delbrueckii co-fermented with different S. cerevisiae strain could generate diversified physicochemical and aromatic quality of wine as evidenced by PCA. Mixed fermentation of SC45/TD12 produced higher contents of higher alcohol (3-methyl-1-pentanol and phenylethyl alcohol), ethyl esters (ethyl decanoate and ethyl butanoate), terpenes and phenylacetaldehyde with less fatty acids (hexanoic acid, octanoic acid) and acetic acid, while BDX/TD12 generated more C6 alcohol (1-hexanol) and acetate esters (ethyl acetate and isoamyl acetate). Compared to simultaneous inoculation, sequential inoculation could achieve higher aroma diversity, and generate higher intensity of fruity, flowery and sweet attributes of wine as assessed by calculating the odor activity values. The different S. cerevisiae strain and inoculation method in alcoholic fermentation could further influence the formations of aromatic compounds in malolactic fermentation. Our results highlighted the importance of S. cerevisiae strain in shaping the aromatic quality of wine in mixed fermentation, and also suggested that using different S. cerevisiae strains with distinct aromatic characteristics co-fermentation with specific non-Saccharomyces strain is a potential way to increase the aromatic diversity and quality of wine product, which could provide an alternative way to meet the requirement of wine consumers for diversified aromatic quality. PMID:29674999

Intraperitoneal administration of docosahexaenoic acid for 14days increases serum unesterified DHA and seizure latency in the maximal pentylenetetrazol model.

PubMed

Trépanier, Marc-Olivier; Lim, Joonbum; Lai, Terence K Y; Cho, Hye Jin; Domenichiello, Anthony F; Chen, Chuck T; Taha, Ameer Y; Bazinet, Richard P; Burnham, W M

2014-04-01

Docosahexaenoic acid (DHA) is an omega-3 polyunsaturated fatty acid (n-3 PUFA) which has been shown to raise seizure thresholds following acute administration in rats. The aims of the present experiment were the following: 1) to test whether subchronic DHA administration raises seizure threshold in the maximal pentylenetetrazol (PTZ) model 24h following the last injection and 2) to determine whether the increase in seizure threshold is correlated with an increase in serum and/or brain DHA. Animals received daily intraperitoneal (i.p.) injections of 50mg/kg of DHA, DHA ethyl ester (DHA EE), or volume-matched vehicle (albumin/saline) for 14days. On day 15, one subset of animals was seizure tested in the maximal PTZ model (Experiment 1). In a separate (non-seizure tested) subset of animals, blood was collected, and brains were excised following high-energy, head-focused microwave fixation. Lipid analysis was performed on serum and brain (Experiment 2). For data analysis, the DHA and DHA EE groups were combined since they did not differ significantly from each other. In the maximal PTZ model, DHA significantly increased seizure latency by approximately 3-fold as compared to vehicle-injected animals. This increase in seizure latency was associated with an increase in serum unesterified DHA. Total brain DHA and brain unesterified DHA concentrations, however, did not differ significantly in the treatment and control groups. An increase in serum unesterified DHA concentration reflecting increased flux of DHA to the brain appears to explain changes in seizure threshold, independent of changes in brain DHA concentrations. Copyright © 2014 Elsevier Inc. All rights reserved.

[Synthesis and monolayer behaviors of 4-methyl-5-hydroxy-ethyl isothiazole stearic ester].

PubMed

Shen, Yu-hua; Kong, Lin; Yang, Jia-xiang; Xie, An-jian; Qian, Jia-sheng; Ouyang, Jian-ming; Xia, Bing

2002-12-01

4-methyl-5-hydroxy-ethyl isothiazole stearic ester (HISE) was synthesized and characterized by FTIR spectroscopy, 1H NMR and MS. The monolayer-forming ability of HISE was studied in subphases with different pH values using isotherms of surface pressure-area per molecule (pi-A). It was observed that the collapse pressure and the film-forming ability of the monolayers of HISE increased gradually as pH values ascended. Research of differentiated pi-A curves (d pi(/dA-A) indicated that there were one or two phase change points during the compressing process, and the incompressibility and the stability of HISE monolayers on alkalescent subphases were better than on acid subphases.

Chemical Composition and Vasorelaxant and Antispasmodic Effects of Essential Oil from Rosa indica L. Petals

PubMed Central

Rasheed, Hafiz Majid; Khan, Taous; Wahid, Fazli; Khan, Rasool; Shah, Abdul Jabbar

2015-01-01

Rosa indica L. belongs to the family Rosaceae and is locally known as gulaab. It has different traditional uses in cardiovascular and gastrointestinal disorders but there is no scientific data available in this regard. Therefore, the basic aim of this study was to explore the chemical composition and gastrointestinal and cardiovascular effects of the essential oil obtained from R. indica. The chemical composition of the essential oil was investigated using gas chromatography-mass spectrometry (GC-MS) technique. The cardiovascular and gastrointestinal effects were investigated using electrophysiological measurements. The GC-MS analysis of the essential oil showed various chemical components including acetic acid, mercaptohexyl ester, butanoic acid, 2-methyl-5-oxo-1-cyclopentene-1-yl ester, artemiseole, methyl santonilate, isosteviol, caryophyllene oxide, pentyl phenyl acetate, dihydromyrcene, 1,5-octadecadien, octadecanoic acid, ethyl ester, palmitic acid (2-phenyl-1,3-dioxolan-4-yl methyl ester), santolina epoxide, and 9-farnesene. The electrophysiological measurements revealed that essential oil was more potent against K+ (80 mM) than phenylephrine precontractions using isolated rabbit aorta preparations. In isolated rabbit jejunum preparations, it showed more potency against high K+ induced contractions than spontaneous contractions. Considering these evidences, it can be concluded that R. indica essential oil may work as a complementary and alternative medicine in gastrointestinal and cardiovascular diseases. PMID:26357519

Enantioseparation and optical rotation of flavor-relevant 4-alkyl-branched fatty acids.

PubMed

Eibler, Dorothee; Vetter, Walter

2017-07-07

Short chain 4-alkyl-branched fatty acids are character impact compounds of the flavor of sheep and goat milk and meat. Due to their methyl or ethyl branches these volatile fatty acids are chiral, and both enantiomers are characterized by different aroma intensities. Recently, it was found that 4-methyloctanoic acid (4-Me-8:0), 4-ethyloctanoic acid (4-Et-8:0), and 4-methylnonanoic acid (4-Me-9:0) are enantiopure in goat and sheep samples, if present. Here we generated enantiopure or enantioenriched standards from racemates by means of (R)-selective esterification with lipase B and verified that 4-Me-8:0, 4-Et-8:0 and 4-Me-9:0 were (R)-enantiopure in these tissues. Determination of the optical rotation and [α] D value was carried out to show that (R)-4-Et-8:0 is dextrorotary and to verify the literature values of (R)-4-methyl-branched fatty acids. The elution order of free acids and the methyl and ethyl esters of 4-Me-8:0, 4-Et-8:0, 4-Me-9:0 and 4-methylhexanoic acid (4-Me-6:0) enantiomers was investigated on different chiral columns as well as the (-)-menthyl ester by indirect enantiomer separation on an ionic liquid phase. Different chiral recognition processes were suggested for free acid and esters of 4-Me-8:0 and 4-Me-9:0 on the one hand (decisive: 4-alkyl branch) compared to 4-Me-6:0 on the other hand (decisive: branch on antepenultimate carbon). Copyright © 2017 Elsevier B.V. All rights reserved.

Identification of Active Compounds in the Root of Merung (Coptosapelta tomentosa Valeton K. Heyne)

NASA Astrophysics Data System (ADS)

Fitriyana

2018-04-01

The roots of Merung (Coptosapelta tomentosa Valeton K. Heyne) are a group of shrubs usually found on the margins of secondary dryland forest. Empirically, local people have been using the roots of Merung for medical treatment. However, some researches show that the plant extract is used as a poisonous material applied on the tip of the arrow (dart). Based on the online literature study, there are less than 5 articles that provide information about the active compound of this root extract. This study aimed to give additional information more deeply about the content of active compound of Merung root extract in three fractions, n-hexane (nonpolar), ethyl acetate (semi polar) and methanol (polar). The extract was then analysed using Gas Chromatography-Mass Spectrometry (GC-MS). GC-MS analysis of root extract in n-hexane showed there were 56 compounds, with the main compound being decanoic acid, methyl ester (peak 5, 10.13%), 11-Octadecenoic acid, methyl ester (peak 15, 10.43%) and 1H-Pyrazole, 3- (4-chlorophenyl) -4, 5-dihydro-1-phenyl (peak 43, 11.25%). Extracts in ethyl acetate fraction obtained 81 compounds. The largest component is Benzoic acid (peak 19, 22.40%), whereas in methanol there are 38 compounds, of which the main component is 2-Furancarboxaldehyde, 5-(hydroxyl methyl) (peak 29, 30.46%).

Characterization of oilseed lipids from "DHA-producing Camelina sativa": a new transformed land plant containing long-chain omega-3 oils.

PubMed

Mansour, Maged P; Shrestha, Pushkar; Belide, Srinivas; Petrie, James R; Nichols, Peter D; Singh, Surinder P

2014-02-21

New and sustainable sources of long-chain (LC, ≥C₂₀) omega-3 oils containing DHA (docosahexaenoic acid, 22:6ω3) are required to meet increasing demands. The lipid content of the oilseed of a novel transgenic, DHA-producing land plant, Camelina sativa, containing microalgal genes able to produce LC omega-3 oils, contained 36% lipid by weight with triacylglycerols (TAG) as the major lipid class in hexane extracts (96% of total lipid). Subsequent chloroform-methanol (CM) extraction recovered further lipid (~50% polar lipid, comprising glycolipids and phospholipids) and residual TAG. The main phospholipid species were phosphatidyl choline and phosphatidyl ethanolamine. The % DHA was: 6.8% (of total fatty acids) in the TAG-rich hexane extract and 4.2% in the polar lipid-rich CM extract. The relative level of ALA (α-linolenic acid, 18:3ω3) in DHA-camelina seed was higher than the control. Major sterols in both DHA- and control camelina seeds were: sitosterol, campesterol, cholesterol, brassicasterol and isofucosterol. C₁₆-C₂₂ fatty alcohols, including iso-branched and odd-chain alcohols were present, including high levels of iso-17:0, 17:0 and 19:0. Other alcohols present were: 16:0, iso-18:0, 18:0 and 18:1 and the proportions varied between the hexane and CM extracts. These iso-branched odd-chain fatty alcohols, to our knowledge, have not been previously reported. These components may be derived from wax esters, or free fatty alcohols.

An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.

PubMed

Smith, Amos B; Dong, Shuzhi

2009-03-05

An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A (1), in conjunction with an effective, stereocontrolled protocol to arrive at the requisite (Z,Z,E)-triene acid system has been developed. Highlights of the core construction entail a three-component union, a KHMDS-promoted epoxide ring formation-ring opening cascade, a Takai olefination, and a chemoselective Sharpless dihydroxylation. Assembly of the triene acid system was then achieved via Stille cross-coupling with the ethyl ester of (Z,Z)-5-tributylstannyl-2,4-pentadienoic acid, followed by mild hydrolysis preserving the triene configuration.

Orally administered DTPA penta-ethyl ester for the decorporation of inhaled 241Am

PubMed Central

Sueda, Katsuhiko; Sadgrove, Matthew P.; Huckle, James E.; Leed, Marina G. D.; Weber, Waylon M.; Doyle-Eisele, Melanie; Guilmette, Raymond A.; Jay, Michael

2014-01-01

Diethylenetriaminepentaacetic acid (DTPA) is an effective decorporation agent to facilitate the elimination of radionuclides from the body, but its permeability-limited oral bioavailability limits its utility in mass-casualty emergencies. To overcome this limitation, a prodrug strategy using the penta-ethyl ester form of DTPA is under investigation. Pharmacokinetic and biodistribution studies were conducted in rats by orally administering [14C]DTPA penta-ethyl ester, and this prodrug and its hydrolysis products were analyzed as a single entity. Compared to a previous reporting of intravenously administered DTPA, the oral administration of this prodrug resulted in a sustained plasma concentration profile with higher plasma exposure and lower clearance. An assessment of the urine composition revealed that the bioactivation was extensive but incomplete, with no detectable levels of the penta- or tetra-ester forms. Tissue distribution at 12 h was limited, with approximately 73% of the administered dose being associated with the gastrointestinal tract. In the efficacy study, rats were exposed to aerosols of 241Am nitrate before receiving a single oral treatment of the prodrug. The urinary excretion of 241Am was found to be 19% higher than with the control. Consistent with prior reports of DTPA, the prodrug was most effective when the treatment delays were minimized. PMID:24619514

Triphenyltin derivatives of sulfanylcarboxylic esters.

PubMed

Casas, José S; Couce, María D; Sánchez, Agustín; Seoane, Rafael; Sordo, José; Perez-Estévez, Antonio; Vázquez-López, Ezequiel

2018-03-01

The reaction of 3-(aryl)-2-sulfanylpropenoic acids [H 2 xspa; x: p=3-phenyl-, f=3-(2-furyl)-, t=3-(2-thienyl)-] with methanol or ethanol gave the corresponding methyl (Hxspme) or ethyl (Hxspee) esters. The reaction of these esters (HL) with triphenyltin(IV) hydroxide gave compounds of the type [SnPh 3 L], which were isolated and characterized as solids by elemental analysis, IR spectroscopy and mass spectrometry and in solution by multinuclear ( 1 H, 13 C and 119 Sn) NMR spectroscopy. The structures of [SnPh 3 (pspme)], [SnPh 3 (fspme)] and [SnPh 3 (fspee)] were determined by X-ray diffractometry and the antimicrobial activity against E. coli, S. aureus, B. subtilis, P. aeruginosa, Resistant P. aeruginosa (a strain resistant to 'carbapenem'), and C. albicans was tested and the in vitro cytotoxic activity against the HeLa-229, A2780 and A2780cis cell lines was determined for all compounds. Copyright © 2017 Elsevier Inc. All rights reserved.

The influence of yeast on chemical composition and sensory properties of dry white wines.

PubMed

Puertas, B; Jimenez-Hierro, M J; Cantos-Villar, E; Marrufo-Curtido, A; Carbú, M; Cuevas, F J; Moreno-Rojas, J M; González-Rodríguez, V E; Cantoral, J M; Ruiz-Moreno, M J

2018-07-01

This study evaluates the impact on two varietal white wines from 'Chardonnay' and 'Verdejo' cultivars of different fermentative strategies: inoculation with Saccharomyces cerevisiae yeast (CT), sequential inoculation (Torulaspora delbrueckii/Saccharomyces cerevisiae) (SI), and spontaneous fermentation (SP). The wines' chemical composition was characterized by oenological parameters, organic acids, metals, major volatile compounds, ester compounds and sensory analyses. The fermentative strategy (CT, SI and SP) was found to be a key factor for assessing different styles of white wines. SI wines showed enhanced 'mature fruit' nuances and a chemical profile characterized by higher content of ethyl propanoate, ethyl isobutyrate and ethyl dihydrocinnamate. Meanwhile, the SP wines presented enhanced "stone fruit" nuances possible related to the higher contents of 2-phenyl acetate and isobutyl acetate. After a chemometric approach the above esters were identified as the markers of each fermentative strategy, independently of the variety. Copyright © 2018 Elsevier Ltd. All rights reserved.

40 CFR 721.10020 - Benzoic acid, 5-amino-2-chloro-, 1,1-dimethyl-2-oxo-2-(2-propenyloxy) ethyl ester.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Benzoic acid, 5-amino-2-chloro-, 1,1... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10020 Benzoic acid, 5-amino-2-chloro... subject to reporting. (1) The chemical substance identified as benzoic acid, 5-amino-2-chloro-, 1,1...

40 CFR 721.10020 - Benzoic acid, 5-amino-2-chloro-, 1,1-dimethyl-2-oxo-2-(2-propenyloxy) ethyl ester.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Benzoic acid, 5-amino-2-chloro-, 1,1... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10020 Benzoic acid, 5-amino-2-chloro... subject to reporting. (1) The chemical substance identified as benzoic acid, 5-amino-2-chloro-, 1,1...

Cell Communication during Aggregation and Development of the Cellular Slime Mould Distyostelium discoideum.

DTIC Science & Technology

1985-01-01

of actin protein xg relative centrifugal force glorin N-propionyl- Y -L-glutawyl-L-ornithine- S- lactam ethyl ester [3 H]FA [7,9,3’,5 ’-3H]folic acid...solubilize the pellet and radioactivity was measured on a LKB Rack Beta scintillation counter. cAMP Binding to Whole Cells. This assay followed the well...inserts, pre-filled with 4ml of Unisolve I scintillant, and radioactivity measured on a LKB Rack Beta scintillation counter. Controls included: a) no

21 CFR 175.210 - Acrylate ester copolymer coating.

Code of Federal Regulations, 2010 CFR

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Acrylate ester copolymer coating. 175.210 Section... COATINGS Substances for Use as Components of Coatings § 175.210 Acrylate ester copolymer coating. Acrylate...) The acrylate ester copolymer is a fully polymerized copolymer of ethyl acrylate, methyl methacrylate...

Preactivated thiolated nanoparticles: A novel mucoadhesive dosage form.

PubMed

Menzel, Claudia; Bonengel, Sonja; Pereira de Sousa, Irene; Laffleur, Flavia; Prüfert, Felix; Bernkop-Schnürch, Andreas

2016-01-30

Within this study a novel form of mucoadhesive nanoparticles (NPs) exhibiting a prolonged residence time on mucosal tissues was developed. In order to achieve this goal a new thiomer was synthesized by the covalent attachment of the amino acid l-cysteine ethyl ester to poly(acrylic acid) (100 kDa). The free thiol groups were in the following preactivated with the aromatic thiol bearing ligand 2-mercaptonicotinic acid (2-MNA) and the amount of coupled l-cysteine ethyl ester as well as the amount of attached 2-MNA was determined. Based on this, preactivated thiomer NPs were prepared by ionic gelation with polyethylenimine (PEI). The resulting NPs were characterized regarding size and zeta potential. Furthermore their mucoadhesive properties were investigated via rheological measurements with porcine intestinal mucus and via determination of the particles' mucosal residence time. Results showed that 1666.74 μmol l-cysteine ethyl ester and 603.07 μmol 2-MNA could be attached per gram polymer. NPs were in a size range of 112.67-252.84 nm exhibiting a zeta potential of -29 mV. Thiolated NPs only led to a 2-fold increase in mucus viscosity whereas preactivated NPs showed a 6-fold higher mucus viscosity than unmodified NPs. The mucosal residence time of thiolated NPs was 1.6-fold prolonged and that of preactivated NPs even 4.4-fold higher compared to unmodified particles. Accordingly, preactivated thiolated NPs providing a prolonged residence time on mucosal membranes could be a promising dosage form for various applications. Copyright © 2015 Elsevier B.V. All rights reserved.

Rapid molecular assessment of the bioturbation extent in sandy soil horizons under pine using ester-bound lipids by on-line thermally assisted hydrolysis and methylation-gas chromatography/mass spectrometry.

PubMed

Nierop, Klaas G J; Verstraten, Jacobus M

2004-01-01

Each plant species has a unique chemical composition, and also within a given plant the various tissues differ from one another in their chemistry. These different compositions can be traced back after decay of the plant parts when they are transformed into soil organic matter (SOM). As a result, the composition of SOM reflects not only the plant origin, but also the various tissues, and the composition consequently provides an estimate of the contribution of above-ground vs. below-ground litter. From the latter distribution the extent of bioturbation (mixing of above-ground litter with the mineral soil) can be assessed. Application of thermally assisted hydrolysis and methylation (THM) using tetramethylammonium hydroxide (TMAH) and subsequent analysis by gas chromatography/mass spectrometry (GC/MS) releases all typical cutin- and suberin-derived aliphatic monomers (mono-, di- and trihydroxyalkanoic acids, alpha,omega-alkanedioic acids) as their methyl esters and/or ethers in a rapid manner. Using the distribution of omega-hydroxyalkanoic acids that are present in pine needle cutin (C(12) and C(14)) and not in root suberin, and those that are present in roots but not in needles (C(20) and C(22)), the extent of bioturbation (mixing of above-ground plant litter with the mineral soil) can be assessed. Similarly, the (9,16-dihydroxyhexadecanoic acid+9,10,18-trihydroxyoctadecanoic acid)/(C(20) + C(22) alpha,omega-alkanedioic acids) ratio reflects the degree of bioturbation. Three mineral soil profiles under Corsican pine with an A horizon that exhibited extensive bioturbation phenomena, and underlying C horizons with hardly any or no bioturbation, were investigated in order to examine the applicability of such an approach. It appeared that the A horizons contained all four mentioned omega-hydroxyalkanoic acids, while the C horizons contained virtually only the C(20) and C(22) members. The results not only suggest that bioturbation occurs in the A horizons, but also that possible illuviation or other transport mechanisms of omega-hydroxyalkanoic acids seem hardly ever or never to occur, which is a prerequisite for applying this biomarker approach in assessing degrees of bioturbation. Copyright 2004 John Wiley & Sons, Ltd.

Characterization of aroma compounds in apple cider using solvent-assisted flavor evaporation and headspace solid-phase microextraction.

PubMed

Xu, Yan; Fan, Wenlai; Qian, Michael C

2007-04-18

The aroma-active compounds in two apple ciders were identified using gas chromatography-olfactometry (GC-O) and GC-mass spectrometry (MS) techniques. The volatile compounds were extracted using solvent-assisted flavor evaporation (SAFE) and headspace solid-phase microextraction (HS-SPME). On the basis of odor intensity, the most important aroma compounds in the two apple cider samples were 2-phenylethanol, butanoic acid, octanoic acid, 2-methylbutanoic acid, 2-phenylethyl acetate, ethyl 2-methylbutanoate, ethyl butanoate, ethyl hexanoate, 4-ethylguaiacol, eugenol, and 4-vinylphenol. Sulfur-containing compounds, terpene derivatives, and lactones were also detected in ciders. Although most of the aroma compounds were common in both ciders, the aroma intensities were different. Comparison of extraction techniques showed that the SAFE technique had a higher recovery for acids and hydroxy-containing compounds, whereas the HS-SPME technique had a higher recovery for esters and highly volatile compounds.

Non-enzymatic cyclization of creatine ethyl ester to creatinine.

PubMed

Giese, Matthew W; Lecher, Carl S

2009-10-16

Creatine ethyl ester was incubated at 37 degrees C in both water and phosphate-buffered saline and the diagnostic methylene resonances in the (1)H NMR spectrum were used to identify the resultant products. It was found that mild aqueous conditions result in the cyclization of creatine ethyl ester to provide inactive creatinine as the exclusive product, and this transformation becomes nearly instantaneous as the pH approaches 7.4. This study demonstrates that mild non-enzymatic conditions are sufficient for the cyclization of creatine ethyl ester into creatinine, and together with previous results obtained under enzymatic conditions suggests that there are no physiological conditions that would result in the production of creatine. It is concluded that creatine ethyl ester is a pronutrient for creatinine rather than creatine under all physiological conditions encountered during transit through the various tissues, thus no ergogenic effect is to be expected from supplementation.

Characterization of volatile compounds responsible for the aroma in naturally fermented sausages by gas chromatography-olfactometry.

PubMed

Olivares, Alicia; Navarro, José Luis; Flores, Mónica

2015-03-01

The objective of this study was to characterize naturally fermented dry sausages produced without the use of microbial starters and to determine which odour-active compounds are responsible for their aroma. The traditional manufacture was responsible for different chemical characteristics and consumer's acceptance. The volatile compounds detected in the headspace comprised a complex mixture of volatile compounds derived from bacterial metabolism (mainly esterase activity of Staphyloccoci), spices and lipid auto-oxidation. The odour-active volatile compounds were identified using gas chromatography coupled to olfactometry (GC-O) using the detection frequency method. The aroma profile was characterized by the presence of several compounds such as acetic acid, ethyl butanoate, hexanal, methional, 1-octen-3-ol, benzeneacetaldehyde and 4-methyl-phenol. However, naturally fermented sausages were also characterized by numerous esters, both ethyl and methyl esters, which impart a wide variety of fruity notes. © The Author(s) 2013 Reprints and permissions: sagepub.co.uk/journalsPermissions.nav.

Linkage and Branch Analysis of High-Mannose Oligosaccharides Using Closed-Ring Labeling of 8-Aminopyrene-1,3,6-Trisulfonate and P-Aminobenzoic Ethyl Ester and Negative Ion Trap Mass Spectrometry

NASA Astrophysics Data System (ADS)

Chen, Shu-Ting; Her, Guor-Rong

2012-08-01

A strategy based on negative ion electrospray ionization tandem mass spectrometry and closed-ring labeling with both 8-aminopyrene-1,3,6-trisulfonate (APTS) and p-aminobenzoic acid ethyl ester (ABEE) was developed for linkage and branch determination of high-mannose oligosaccharides. X-type cross-ring fragment ions obtained from APTS-labeled oligosaccharides by charge remote fragmentation provided information on linkages near the non-reducing terminus. In contrast, A-type cross-ring fragment ions observed from ABEE-labeled oligosaccharides yielded information on linkages near the reducing terminus. This complementary information provided by APTS- and ABEE-labeled oligosaccharides was utilized to delineate the structures of the high-mannose oligosaccharides. As a demonstration of this approach, the linkages and branches of high-mannose oligosaccharides Man5GlcNAc2, Man6GlcNAc2, Man8GlcNAc2, and Man9GlcNAc2 cleaved from the ribonuclease B were assigned from MS2 spectra of ABEE- and APTS-labeled derivatives.

Effects of dietary omega-3 and -6 supplementations on phospholipid fatty acid composition in mice uterus during window of pre-implantation.

PubMed

Fattahi, Amir; Darabi, Masoud; Farzadi, Laya; Salmassi, Ali; Latifi, Zeinab; Mehdizadeh, Amir; Shaaker, Maghsood; Ghasemnejad, Tohid; Roshangar, Leila; Nouri, Mohammad

2018-03-01

Since fatty acid composition of uterus phospholipids is likely to influence embryo implantation, this study was conducted to investigate the effects of dietary omega-3 and -6 fatty acids on implantation rate as well as uterine phospholipid fatty acids composition during mice pre-implantation period. Sixty female mice were randomly distributed into:1) control (standard pellet), 2) omega-3 (standard pellet + 10% w/w of omega-3 fatty acids) and 3) omega-6 (standard pellet + 10% w/w of omega-6 fatty acids). Uterine phospholipid fatty acid composition during the pre-implantation window (days 1-5 of pregnancy) was analyzed using gas-chromatography. The implantation rate on the fifth day of pregnancy was also determined. Our results showed that on days 1, 2 and 3 of pregnancy, the levels of arachidonic acid (ARA) as well as total omega-6 fatty acids were significantly higher and the levels of linolenic acid and total omega-3 fatty acids were statistically lower in the omega-6 group compared to the omega-3 group (p < 0.05). On the fourth day of pregnancy, only the ARA, total omega-6 fatty acids, and poly-unsaturated fatty acids levels were significantly different between the two dietary supplemented groups (p < 0.05). There were positive correlations between the levels of omega-6 fatty acids, especially ARA, with the implantation rate. The present study showed that diets rich in omega-3 and -6 fatty acids could differently modify uterine phospholipid fatty acid composition and uterine levels of phospholipid ARA, and that the total omega-6 fatty acids had a positive association with the implantation rate. Copyright © 2017 Elsevier Inc. All rights reserved.

Identification of 3-hydroxy-3-methylglutaric acid (HMG) as a hypoglycemic principle of Spanish moss (Tillandsia usneoides).

PubMed

Witherup, K M; McLaughlin, J L; Judd, R L; Ziegler, M H; Medon, P J; Keller, W J

1995-08-01

Bioactivity-directed fractionation, using brine shrimp lethality and murine hypoglycemia, of an ethanol extract prepared from Tillandsia usneoides, led to the isolation of four apparently bioactive compounds from the water-soluble fraction. The compounds were identified as citric acid, succinic acid, 3-hydroxy-3-methylglutaric acid (HMG), and 3,6,3',5'-tetramethoxy-5,7,4'-trihydroxyflavone-7-O-beta-D-g lucoside. The brine shrimp lethality of the acids was simply due to acidity; however, HMG elicited significant hypoglycemic responses in fasting normal mice. Ethyl and methyl esters of citric acid were prepared and tested in the murine hypoglycemic assay. Five of the predominant sugars were identified by tlc. Free thymidine was also isolated. Further evaluation of HMG and other potential inhibitors of HMG CoA lyase, in the treatment of symptoms of diabetes mellitus, is suggested.

An Increase in the Omega-6/Omega-3 Fatty Acid Ratio Increases the Risk for Obesity.

PubMed

Simopoulos, Artemis P

2016-03-02

In the past three decades, total fat and saturated fat intake as a percentage of total calories has continuously decreased in Western diets, while the intake of omega-6 fatty acid increased and the omega-3 fatty acid decreased, resulting in a large increase in the omega-6/omega-3 ratio from 1:1 during evolution to 20:1 today or even higher. This change in the composition of fatty acids parallels a significant increase in the prevalence of overweight and obesity. Experimental studies have suggested that omega-6 and omega-3 fatty acids elicit divergent effects on body fat gain through mechanisms of adipogenesis, browning of adipose tissue, lipid homeostasis, brain-gut-adipose tissue axis, and most importantly systemic inflammation. Prospective studies clearly show an increase in the risk of obesity as the level of omega-6 fatty acids and the omega-6/omega-3 ratio increase in red blood cell (RBC) membrane phospholipids, whereas high omega-3 RBC membrane phospholipids decrease the risk of obesity. Recent studies in humans show that in addition to absolute amounts of omega-6 and omega-3 fatty acid intake, the omega-6/omega-3 ratio plays an important role in increasing the development of obesity via both AA eicosanoid metabolites and hyperactivity of the cannabinoid system, which can be reversed with increased intake of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). A balanced omega-6/omega-3 ratio is important for health and in the prevention and management of obesity.

An Increase in the Omega-6/Omega-3 Fatty Acid Ratio Increases the Risk for Obesity

PubMed Central

Simopoulos, Artemis P.

2016-01-01

In the past three decades, total fat and saturated fat intake as a percentage of total calories has continuously decreased in Western diets, while the intake of omega-6 fatty acid increased and the omega-3 fatty acid decreased, resulting in a large increase in the omega-6/omega-3 ratio from 1:1 during evolution to 20:1 today or even higher. This change in the composition of fatty acids parallels a significant increase in the prevalence of overweight and obesity. Experimental studies have suggested that omega-6 and omega-3 fatty acids elicit divergent effects on body fat gain through mechanisms of adipogenesis, browning of adipose tissue, lipid homeostasis, brain-gut-adipose tissue axis, and most importantly systemic inflammation. Prospective studies clearly show an increase in the risk of obesity as the level of omega-6 fatty acids and the omega-6/omega-3 ratio increase in red blood cell (RBC) membrane phospholipids, whereas high omega-3 RBC membrane phospholipids decrease the risk of obesity. Recent studies in humans show that in addition to absolute amounts of omega-6 and omega-3 fatty acid intake, the omega-6/omega-3 ratio plays an important role in increasing the development of obesity via both AA eicosanoid metabolites and hyperactivity of the cannabinoid system, which can be reversed with increased intake of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). A balanced omega-6/omega-3 ratio is important for health and in the prevention and management of obesity. PMID:26950145

Microbial Transformation of Esters of Chlorinated Carboxylic Acids

PubMed Central

Paris, D. F.; Wolfe, N. L.; Steen, W. C.

1984-01-01

Two groups of compounds were selected for microbial transformation studies. In the first group were carboxylic acid esters having a fixed aromatic moiety and an increasing length of the alkyl component. Ethyl esters of chlorine-substituted carboxylic acids were in the second group. Microorganisms from environmental waters and a pure culture of Pseudomonas putida U were used. The bacterial populations were monitored by plate counts, and disappearance of the parent compound was followed by gas-liquid chromatography as a function of time. The products of microbial hydrolysis were the respective carboxylic acids. Octanol-water partition coefficients (Kow) for the compounds were measured. These values spanned three orders of magnitude, whereas microbial transformation rate constants (kb) varied only 50-fold. The microbial rate constants of the carboxylic acid esters with a fixed aromatic moiety increased with an increasing length of alkyl substituents. The regression coefficient for the linear relationships between log kb and log Kow was high for group 1 compounds, indicating that these parameters correlated well. The regression coefficient for the linear relationships for group 2 compounds, however, was low, indicating that these parameters correlated poorly. PMID:16346459

The electron transport mechanism in ester and its influence on bioactivity in the anticancer drug N-(6-ferrocenyl-2-naphthoyl)-L-alanine-glycine ethyl ester(FNLAGEE)

NASA Astrophysics Data System (ADS)

Sudhi, Geethu; Rajina, S. R.; Praveen, S. G.; Xavier, T. S.; Kenny, Peter T. M.; Binoy, J.

2018-05-01

The reactivity of ester group plays key role in inducing bioactivity of many ferrocenyl biconjugated compounds. The ester reactivity can be explained, based on electron transport mechanism using vibrational spectroscopy, aided by DFT simulation. The FT IR and FT Raman spectral measurements have been carried out for N-(6-ferrocenyl-2-naphthoyl)-L-alanine-glycine ethyl ester (FNLAGEE) and the optimized geometry and vibrational spectra have been computed using DFT method, at B3LYP/LANL2DZ level of theory. The cis conformation of ester and electron transport mechanism, thus analyzed, has been correlated to the geometry and the spectral characteristics of ester. To investigate the bioactivity and binding interactions of the molecule, molecular docking simulations and UV-Vis absorption studies of FNLAGEE with BSA and DNA has been performed.

Diet-induced changes in n-3- and n-6-derived endocannabinoids and reductions in headache pain and psychological distress.

PubMed

Ramsden, Christopher E; Zamora, Daisy; Makriyannis, Alexandros; Wood, JodiAnne T; Mann, J Douglas; Faurot, Keturah R; MacIntosh, Beth A; Majchrzak-Hong, Sharon F; Gross, Jacklyn R; Courville, Amber B; Davis, John M; Hibbeln, Joseph R

2015-08-01

Omega-3 and omega-6 fatty acids are biosynthetic precursors of endocannabinoids with antinociceptive, anxiolytic, and neurogenic properties. We recently reported that targeted dietary manipulation-increasing omega-3 fatty acids while reducing omega-6 linoleic acid (the H3-L6 intervention)-reduced headache pain and psychological distress among chronic headache patients. It is not yet known whether these clinical improvements were due to changes in endocannabinoids and related mediators derived from omega-3 and omega-6 fatty acids. We therefore used data from this trial (N = 55) to investigate 1) whether the H3-L6 intervention altered omega-3- and omega-6-derived endocannabinoids in plasma and 2) whether diet-induced changes in these bioactive lipids were associated with clinical improvements. The H3-L6 intervention significantly increased the omega-3 docosahexaenoic acid derivatives 2-docosahexaenoylglycerol (+65%, P < .001) and docosahexaenoylethanolamine (+99%, P < .001) and reduced the omega-6 arachidonic acid derivative 2-arachidonoylglycerol (-25%, P = .001). Diet-induced changes in these endocannabinoid derivatives of omega-3 docosahexaenoic acid, but not omega-6 arachidonic acid, correlated with reductions in physical pain and psychological distress. These findings demonstrate that targeted dietary manipulation can alter endocannabinoids derived from omega-3 and omega-6 fatty acids in humans and suggest that 2-docosahexaenoylglycerol and docosahexaenoylethanolamine could have physical and/or psychological pain modulating properties. ClinicalTrials.gov (NCT01157208) PERSPECTIVE: This article demonstrates that targeted dietary manipulation can alter endocannabinoids derived from omega-3 and omega-6 fatty acids and that these changes are related to reductions in headache pain and psychological distress. These findings suggest that dietary interventions could provide an effective, complementary approach for managing chronic pain and related conditions. Published by Elsevier Inc.

The ferroin-catalyzed Belousov-Zhabotinskii system with a "clock" behaviour

NASA Astrophysics Data System (ADS)

Melicherčík, Milan; Treindl, L̆udovít

1991-07-01

The ferroin-catalyzed Belousov-Zhabotinskii oscillatory system with methyl-, ethyl-, or isopropyl-ester of 3-oxobutanoic acid exhibits a "clock" behaviour and subsequent two-frequency oscillations. The influence of oxygen on the "clock" behaviour is assumed to be caused by an interaction of oxygen as a scavenger with intermediary radicals. A mechanism of the "clock" behaviour together with two-frequency oscillations of the Belousov-Zhabotinskii type will be developed later.

Compendium of the FY1990 and FY1992 Research Reviews for the Research Methods Branch

DTIC Science & Technology

1994-09-01

the perfusion technique, the perfusion was not done in situ. Trout were anesthetized with MS-222 (3-aminobenzoic acid ethyl ester, Sigma Chemical...by a trypan blue exclusion test. Medaka Medaka were anesthetized with MS-222, transferred to a dissecting tray, and incised from the urogenital pore...Histology General histology was compared at intervals of 20 days. Fish were anesthetized , fixed, and processed for paraffin embedment, and sections

Extraction and Liquid Chromatography-Tandem Mass Spectrometry Detection of 3-Monochloropropanediol Esters and Glycidyl Esters in Infant Formula.

PubMed

Leigh, Jessica K; MacMahon, Shaun

2016-12-14

A method was developed for the extraction of fatty acid esters of 3-chloro-1,2-propanediol (3-MCPD) and glycidol from infant formula, followed by quantitative analysis of the extracts using liquid chromatography-tandem mass spectrometry (LC-MS/MS). These process-induced chemical contaminants are found in refined vegetable oils, and studies have shown that they are potentially carcinogenic and/or genotoxic, making their presence in edible oils (and processed foods containing these oils) a potential health risk. The extraction procedure involves a liquid-liquid extraction, where powdered infant formula is dissolved in water and extracted with ethyl acetate. Following shaking, centrifugation, and drying of the organic phase, the resulting fat extract is cleaned-up using solid-phase extraction and analyzed by LC-MS/MS. Method performance was confirmed by verifying the percent recovery of each 3-MCPD and glycidyl ester in a homemade powdered infant formula reference material. Average ester recoveries in the reference material ranged from 84.9 to 109.0% (0.6-9.5% RSD). The method was also validated by fortifying three varieties of commercial infant formulas with a 3-MCPD and glycidyl ester solution. Average recoveries of the esters across all concentrations and varieties of infant formula ranged from 88.7 to 107.5% (1.0-9.5% RSD). Based on the validation results, this method is suitable for producing 3-MCPD and glycidyl ester occurrence data in all commercially available varieties of infant formula.

Icosapent ethyl (eicosapentaenoic acid ethyl ester): Effects on remnant-like particle cholesterol from the MARINE and ANCHOR studies.

PubMed

Ballantyne, Christie M; Bays, Harold E; Philip, Sephy; Doyle, Ralph T; Braeckman, Rene A; Stirtan, William G; Soni, Paresh N; Juliano, Rebecca A

2016-10-01

Remnant-like particle cholesterol (RLP-C) is atherogenic and may increase atherosclerotic cardiovascular disease risk. Icosapent ethyl is a high-purity prescription eicosapentaenoic acid ethyl ester (approved as an adjunct to diet to reduce triglyceride [TG] levels in adult patients with TGs ≥500 mg/dL [≥5.65 mmol/L] at 4 g/day). In the MARINE and ANCHOR studies, icosapent ethyl reduced TG and other atherogenic lipid parameter levels without increasing low-density lipoprotein cholesterol (LDL-C) levels. This exploratory analysis evaluated the effects of icosapent ethyl on calculated and directly measured RLP-C. MARINE (TGs ≥500 and ≤2000 mg/dL [≥5.65 mmol/L and ≤22.6 mmol/L]) and ANCHOR (TGs ≥200 and <500 mg/dL [≥2.26 and <5.65 mmol/L] despite statin-controlled LDL-C) were phase 3, 12-week, double-blind studies that randomized adult patients to icosapent ethyl 4 g/day, 2 g/day, or placebo. This analysis assessed median percent change from baseline to study end in directly measured (immunoseparation assay) RLP-C levels (MARINE, n = 218; ANCHOR, n = 252) and calculated RLP-C levels in the full populations. Icosapent ethyl 4 g/day significantly reduced directly measured RLP-C levels -29.8% (p = 0.004) in MARINE and -25.8% (p = 0.0001) in ANCHOR versus placebo, and also reduced directly measured RLP-C levels to a greater extent in subgroups with higher versus lower baseline TG levels, in patients receiving statins versus no statins (MARINE), and in patients receiving medium/higher-intensity versus lower-intensity statins (ANCHOR). Strong correlations were found between calculated and directly measured RLP-C for baseline, end-of-treatment, and percent change values in ANCHOR and MARINE (0.73-0.92; p < 0.0001 for all). Icosapent ethyl 4 g/day significantly reduced calculated and directly measured RLP-C levels versus placebo in patients with elevated TG levels from the MARINE and ANCHOR studies. Copyright © 2016 The Authors. Published by Elsevier Ireland Ltd.. All rights reserved.

A new irreversible enzyme-aided esterification method in organic solvents.

PubMed

Jeromin, Günter E; Zoor, Annegreth

2008-05-01

A new irreversible esterification method for carboxylic acids catalyzed by a lipase from Candida antarctica (Novozyme 435) in organic solvents has been developed. The water produced during the process is chemically destroyed by a corresponding ester of acetoacetate, which acts as a sacrificial substrate in this reaction. The flavour esters isobutyl acetate, methyl butyrate, ethyl butyrate and benzyl butyrate were synthesized either in small scale (0.05 mol) or large scale (1 mol). The yields range from 82 to 92% within 24 h at 52 degrees C. Optimal molar ratios of reactants were 1:1:1 (carboxylic acid:alcohol:acetoacetate).

Synthesis of acid addition salt of delta-aminolevulinic acid from 5-bromo levulinic acid esters

DOEpatents

Moens, Luc

2003-06-24

A process of preparing an acid addition salt of delta-aminolevulinc acid comprising: a) dissolving a lower alkyl 5-bromolevulinate and hexamethylenetetramine in a solvent selected from the group consisting of water, ethyl acetate, chloroform, acetone, ethanol, tetrahydrofuran and acetonitrile, to form a quaternary ammonium salt of the lower alkyl 5-bromolevulinate; and b) hydrolyzing the quaternary ammonium salt with an inorganic acid to form an acid addition salt of delta-aminolevulinic acid.

Original Research: Effect of various dietary fats on fatty acid profile in duck liver: Efficient conversion of short-chain to long-chain omega-3 fatty acids

PubMed Central

Chen, Xi; Du, Xue; Shen, Jianliang; Wang, Weiqun

2016-01-01

Omega-3 fatty acids, especially long-chain omega-3 fatty acids, have been associated with potential health benefits for chronic disease prevention. Our previous studies found that dietary omega-3 fatty acids could accumulate in the meat and eggs in a duck model. This study was to reveal the effects of various dietary fats on fatty acid profile and conversion of omega-3 fatty acids in duck liver. Female Shan Partridge Ducks were randomly assigned to five dietary treatments, each consisting of 6 replicates of 30 birds. The experimental diets substituted the basal diet by 2% of flaxseed oil, rapeseed oil, beef tallow, or fish oil, respectively. In addition, a dose response study was further conducted for flaxseed and fish oil diets at 0.5%, 1%, and 2%, respectively. At the end of the five-week treatment, fatty acids were extracted from the liver samples and analyzed by GC-FID. As expected, the total omega-3 fatty acids and the ratio of total omega-3/omega-6 significantly increased in both flaxseed and fish oil groups when compared with the control diet. No significant change of total saturated fatty acids or omega-3 fatty acids was found in both rapeseed and beef tallow groups. The dose response study further indicated that 59–81% of the short-chain omega-3 ALA in flaxseed oil-fed group was efficiently converted to long-chain DHA in the duck liver, whereas 1% of dietary flaxseed oil could produce an equivalent level of DHA as 0.5% of dietary fish oil. The more omega-3 fatty acids, the less omega-6 fatty acids in the duck liver. Taken together, this study showed the fatty acid profiling in the duck liver after various dietary fat consumption, provided insight into a dose response change of omega-3 fatty acids, indicated an efficient conversion of short- to long-chain omega-3 fatty acid, and suggested alternative long-chain omega-3 fatty acid-enriched duck products for human health benefits. PMID:27510581

Original Research: Effect of various dietary fats on fatty acid profile in duck liver: Efficient conversion of short-chain to long-chain omega-3 fatty acids.

PubMed

Chen, Xi; Du, Xue; Shen, Jianliang; Lu, Lizhi; Wang, Weiqun

2017-01-01

Omega-3 fatty acids, especially long-chain omega-3 fatty acids, have been associated with potential health benefits for chronic disease prevention. Our previous studies found that dietary omega-3 fatty acids could accumulate in the meat and eggs in a duck model. This study was to reveal the effects of various dietary fats on fatty acid profile and conversion of omega-3 fatty acids in duck liver. Female Shan Partridge Ducks were randomly assigned to five dietary treatments, each consisting of 6 replicates of 30 birds. The experimental diets substituted the basal diet by 2% of flaxseed oil, rapeseed oil, beef tallow, or fish oil, respectively. In addition, a dose response study was further conducted for flaxseed and fish oil diets at 0.5%, 1%, and 2%, respectively. At the end of the five-week treatment, fatty acids were extracted from the liver samples and analyzed by GC-FID. As expected, the total omega-3 fatty acids and the ratio of total omega-3/omega-6 significantly increased in both flaxseed and fish oil groups when compared with the control diet. No significant change of total saturated fatty acids or omega-3 fatty acids was found in both rapeseed and beef tallow groups. The dose response study further indicated that 59-81% of the short-chain omega-3 ALA in flaxseed oil-fed group was efficiently converted to long-chain DHA in the duck liver, whereas 1% of dietary flaxseed oil could produce an equivalent level of DHA as 0.5% of dietary fish oil. The more omega-3 fatty acids, the less omega-6 fatty acids in the duck liver. Taken together, this study showed the fatty acid profiling in the duck liver after various dietary fat consumption, provided insight into a dose response change of omega-3 fatty acids, indicated an efficient conversion of short- to long-chain omega-3 fatty acid, and suggested alternative long-chain omega-3 fatty acid-enriched duck products for human health benefits. © 2016 by the Society for Experimental Biology and Medicine.

Efficacy and safety of eicosapentaenoic acid ethyl ester (AMR101) therapy in statin-treated patients with persistent high triglycerides (from the ANCHOR study).

PubMed

Ballantyne, Christie M; Bays, Harold E; Kastelein, John J; Stein, Evan; Isaacsohn, Jonathan L; Braeckman, Rene A; Soni, Paresh N

2012-10-01

AMR101 is an ω-3 fatty acid agent containing ≥96% pure icosapent-ethyl, the ethyl ester of eicosapentaenoic acid. The efficacy and safety of AMR101 were evaluated in this phase 3, multicenter, placebo-controlled, randomized, double-blinded, 12-week clinical trial (ANCHOR) in high-risk statin-treated patients with residually high triglyceride (TG) levels (≥200 and <500 mg/dl) despite low-density lipoprotein (LDL) cholesterol control (≥40 and <100 mg/dl). Patients (n = 702) on a stable diet were randomized to AMR101 4 or 2 g/day or placebo. The primary end point was median percent change in TG levels from baseline versus placebo at 12 weeks. AMR101 4 and 2 g/day significantly decreased TG levels by 21.5% (p <0.0001) and 10.1% (p = 0.0005), respectively, and non-high-density lipoprotein (non-HDL) cholesterol by 13.6% (p <0.0001) and 5.5% (p = 0.0054), respectively. AMR101 4 g/day produced greater TG and non-HDL cholesterol decreases in patients with higher-efficacy statin regimens and greater TG decreases in patients with higher baseline TG levels. AMR101 4 g/day decreased LDL cholesterol by 6.2% (p = 0.0067) and decreased apolipoprotein B (9.3%), total cholesterol (12.0%), very-low-density lipoprotein cholesterol (24.4%), lipoprotein-associated phospholipase A(2) (19.0%), and high-sensitivity C-reactive protein (22.0%) versus placebo (p <0.001 for all comparisons). AMR101 was generally well tolerated, with safety profiles similar to placebo. In conclusion, AMR101 4 g/day significantly decreased median placebo-adjusted TG, non-HDL cholesterol, LDL cholesterol, apolipoprotein B, total cholesterol, very-low-density lipoprotein cholesterol, lipoprotein-associated phospholipase A(2), and high-sensitivity C-reactive protein in statin-treated patients with residual TG elevations. Copyright © 2012 Elsevier Inc. All rights reserved.

Safety of docosahexaenoic acid (DHA) administered as DHA ethyl ester in a 9-month toxicity study in dogs.

PubMed

Dahms, Irina; Beilstein, Paul; Bonnette, Kimberly; Salem, Norman

2016-06-01

DHA Ethyl Ester (DHA-EE) is a 90% concentrated ethyl ester of docosahexaenoic acid manufactured from the microalgal oil. The objective of the 9-month study was to evaluate safety of DHA-EE administered to beagle dogs at dose levels 150, 1000 and 2000 mg/kg bw/day by oral gavage and to determine reversibility of any findings after a 2-month recovery period. DHA-EE was well tolerated at all doses. There were observations of dry flaky skin with occasional reddened areas at doses ≥1000 mg/kg bw/day. These findings lacked any microscopic correlate and were no longer present after the recovery period. There were no toxicologically relevant findings in body weights, body weight gains, food consumption, ophthalmological examinations, and ECG measurements. Test article-related changes in hematology parameters were limited to decreases in reticulocyte count in the high-dose males and considered non-adverse. In clinical chemistry parameters, dose-related decreases in cholesterol and triglycerides levels were observed at all doses in males and females and attributed to the known lipid-lowering effects of DHA. There were no effects on other clinical chemistry, urinalysis or coagulation parameters. There were no abnormal histopathology findings attributed to test article. The No-Observable-Adverse-Effect Level of DHA-EE was established at 2000 mg/kg bw/day for both genders. Copyright © 2016 Elsevier Ltd. All rights reserved.

Furo-fused BINOL based crown as a fluorescent chiral sensor for enantioselective recognition of phenylethylamine and ethyl ester of valine.

PubMed

Upadhyay, Sunil P; Pissurlenkar, Raghuvir R S; Coutinho, Evans C; Karnik, Anil V

2007-07-20

A furo-fused BINOL based chiral crown was developed as an enantioselective chiral sensor for phenylethylamine and ethyl ester of valine. Fusion of furan to BINOL has resulted in a highly stereo-discriminating backbone for the chiral crown developed. This chiral crown exhibited a fluorescence enhancement difference of 2.97 times between two enantiomers of phenylethylamine and 2.55 times between two enantiomers of ethyl ester of valine. The ratio of association constants for two diastereomeric complexes of two enantiomers of phenylethylamine was found to be 11.30, and the ratio for two enantiomers of ethyl ester of valine was 7.02.

Characterization of Oilseed Lipids from “DHA-Producing Camelina sativa”: A New Transformed Land Plant Containing Long-Chain Omega-3 Oils

PubMed Central

Mansour, Maged P.; Shrestha, Pushkar; Belide, Srinivas; Petrie, James R.; Nichols, Peter D.; Singh, Surinder P.

2014-01-01

New and sustainable sources of long-chain (LC, ≥C20) omega-3 oils containing DHA (docosahexaenoic acid, 22:6ω3) are required to meet increasing demands. The lipid content of the oilseed of a novel transgenic, DHA-producing land plant, Camelina sativa, containing microalgal genes able to produce LC omega-3 oils, contained 36% lipid by weight with triacylglycerols (TAG) as the major lipid class in hexane extracts (96% of total lipid). Subsequent chloroform-methanol (CM) extraction recovered further lipid (~50% polar lipid, comprising glycolipids and phospholipids) and residual TAG. The main phospholipid species were phosphatidyl choline and phosphatidyl ethanolamine. The % DHA was: 6.8% (of total fatty acids) in the TAG-rich hexane extract and 4.2% in the polar lipid-rich CM extract. The relative level of ALA (α-linolenic acid, 18:3ω3) in DHA-camelina seed was higher than the control. Major sterols in both DHA- and control camelina seeds were: sitosterol, campesterol, cholesterol, brassicasterol and isofucosterol. C16–C22 fatty alcohols, including iso-branched and odd-chain alcohols were present, including high levels of iso-17:0, 17:0 and 19:0. Other alcohols present were: 16:0, iso-18:0, 18:0 and 18:1 and the proportions varied between the hexane and CM extracts. These iso-branched odd-chain fatty alcohols, to our knowledge, have not been previously reported. These components may be derived from wax esters, or free fatty alcohols. PMID:24566436

Ultrasonic Removal of Mucilage for Pressurized Liquid Extraction of Omega-3 Rich Oil from Chia Seeds (Salvia hispanica L.).

PubMed

Castejón, Natalia; Luna, Pilar; Señoráns, Francisco J

2017-03-29

Chia (Salvia hispanica L.) seeds contain an important amount of edible oil rich in omega-3 fatty acids. Fast and alternative extraction techniques based on polar solvents, such as ethanol or water, have become relevant for oil extraction in recent years. However, chia seeds also contain a large amount of soluble fiber or mucilage, which makes difficult an oil extraction process with polar solvents. For that reason, the aim of this study was to develop a gentle extraction method for mucilage in order to extract chia oil with polar solvents using pressurized liquids and compare with organic solvent extraction. The proposed mucilage extraction method, using an ultrasonic probe and only water, was optimized at mild conditions (50 °C and sonication 3 min) to guarantee the omega-3 oil quality. Chia oil extraction was performed using pressurized liquid extraction (PLE) with different solvents and their mixtures at five different extraction temperatures (60, 90, 120, 150, and 200 °C). Optimal PLE conditions were achieved with ethyl acetate or hexane at 90 °C in only 10 min of static extraction time (chia oil yield up to 30.93%). In addition, chia oils extracted with nonpolar and polar solvents by PLE were analyzed by gas chromatography-mass spectrometry (GC-MS) to evaluate fatty acid composition at different extraction conditions. Chia oil contained ∼65% of α-linolenic acid regardless of mucilage extraction method, solvent, or temperature used. Furthermore, tocopherols and tocotrienols were also analyzed by HPLC in the extracted chia oils. The mucilage removal allowed the subsequent extraction of the chia oil with polar or nonpolar solvents by PLE producing chia oil with the same fatty acid and tocopherol composition as traditional extraction.

Assessment of essential fatty acid and omega3-fatty acid status by measurement of erythrocyte 20:3omega9 (Mead acid), 22:5omega6/20:4omega6 and 22:5omega6/22:6omega3.

PubMed

Fokkema, M R; Smit, E N; Martini, I A; Woltil, H A; Boersma, E R; Muskiet, F A J

2002-11-01

Early suspicion of essential fatty acid deficiency (EFAD) or omega3-deficiency may rather focus on polyunsaturated fatty acid (PUFA) or long-chain PUFA (LCP) analyses than clinical symptoms. We determined cut-off values for biochemical EFAD, omega3-and omega3/22:6omega3 [docosahexaenoic acid (DHA)]-deficiency by measurement of erythrocyte 20:3omega9 (Mead acid), 22:5omega6/20:4omega6 and 22:5omega6/22:6omega3, respectively. Cut-off values, based on 97.5 percentiles, derived from an apparently healthy omnivorous group (six Dominica breast-fed newborns, 32 breast-fed and 27 formula+LCP-fed Dutch low-birth-weight infants, 31 Jerusalem infants, 33 Dutch 3.5-year-old infants, 69 omnivorous Dutch adults and seven Dominica mothers) and an apparently healthy group with low dietary LCP intake (81 formula-fed Dutch low-birth-weight infants, 12 Dutch vegans). Cut-off values were evaluated by their application in an EFAD suspected group of 108, mostly malnourished, Pakistani children, three pediatric patients with chronic fat-malabsorption (abetal-ipoproteinemia, congenital jejunal and biliary atresia) and one patient with a peroxisomal beta-oxidation disorder. Erythrocyte 20:3omega9, 22:5omega6/20:4omega6 and 22:5omega6/22:6omega3 proved age-dependent up to 0.2 years. Cut-off values for ages above 0.2 years were: 0.46mol% 20:3omega9 for EFAD, 0.068mol/mol 22:5omega6/20:4omega6 for omega3-deficiency, 0.22mol/mol 22:5omega6/22:6omega3 for omega3/DHA-marginality and 0.48mol/mol 22:5omega6/22:6omega3 for omega3/DHA-deficiency. Use of RBC 20:3omega9 and 22:5omega6/20:4omega6 cut-off values identified 20.4% of the Pakistani subjects as EFAD+omega3-deficient, 12.9% as EFAD+omega3-sufficient, 38.9% as EFA-sufficient+omega3-deficient and 27.8% as EFA-sufficient+omega3-sufficient. The patient with the peroxisomal disorder was classified as EFA-sufficient, omega3-sufficient (based on RBC 22:5omega6/20:4omega6) and omega3/DHA-deficient (based on RBC 22:5omega6/22:6omega3). The three other pediatric patients were classified as EFAD, omega3-deficient and omega3/DHA-deficient. Use of the combination of the present cut-off values for EFA, omega3 and omega3/DHA status assessment, as based on 97.5 percentiles, may serve for PUFA supplement intervention until better concepts have emerged.

Determination of red blood cell fatty acid profiles: Rapid and high-confident analysis by chemical ionization-gas chromatography-tandem mass spectrometry.

PubMed

Schober, Yvonne; Wahl, Hans Günther; Renz, Harald; Nockher, Wolfgang Andreas

2017-01-01

Cellular fatty acid (FA) profiles have been acknowledged as biomarkers in various human diseases. Nevertheless, common FA analysis by gas chromatography mass spectrometry (GC-MS) requires long analysis time. Hence, there is a need for feasible methods for high throughput analysis in clinical studies. FA was extracted from red blood cells (RBC) and derivatized to fatty acid methyl esters (FAME). A method using gas chromatography tandem mass spectrometry (GC-MS/MS) with ammonia-induced chemical ionization (CI) was developed for the analysis of FA profiles in human RBC. We compared this method with classical single GC-MS using electron impact ionization (EI). The FA profiles of 703 RBC samples were determined by GC-MS/MS. In contrast to EI ammonia-induced CI resulted in adequate amounts of molecular ions for further fragmentation of FAME. Specific fragments for confident quantification and fragmentation were determined for 45 FA. The GC-MS/MS method has a total run time of 9min compared to typical analysis times of up to 60min in conventional GC-MS. Intra and inter assay variations were <10% for all FA analyzed. Analysis of RBC FA composition revealed an age-dependent increase of the omega-3 eicosapentaenoic and docosahexaenoic acid, and a decline of the omega-6 linoleic acid with a corresponding rise of the omega-3 index. The combination of ammonia-induced CI and tandem mass spectrometry after GC separation allows for high-throughput, robust and confident analysis of FA profiles in the clinical laboratory. Copyright © 2016. Published by Elsevier B.V.

Heat capacities and thermal diffusivities of n-alkane acid ethyl esters—biodiesel fuel components

NASA Astrophysics Data System (ADS)

Bogatishcheva, N. S.; Faizullin, M. Z.; Nikitin, E. D.

2017-09-01

The heat capacities and thermal diffusivities of ethyl esters of liquid n-alkane acids C n H2 n-1O2C2H5 with the number of carbon atoms in the parent acid n = 10, 11, 12, 14, and 16 are measured. The heat capacities are measured using a DSC 204 F1 Phoenix heat flux differential scanning calorimeter (Netzsch, Germany) in the temperature range of 305-375 K. Thermal diffusivities are measured by means of laser flash method on an LFA-457 instrument (Netzsch, Germany) at temperatures of 305-400 K. An equation is derived for the dependence of the molar heat capacities of the investigated esters on temperature. It is shown that the dependence of molar heat capacity C p,m (298.15 K) on n ( n = 1-6) is close to linear. The dependence of thermal diffusivity on temperature in the investigated temperature range is described by a first-degree polynomial, but thermal diffusivity a (298.15 K) as a function of n has a minimum at n = 5.

Neurocognitive effects of an omega-3 fatty acid and vitamins E+C in schizophrenia: A randomised controlled trial.

PubMed

Bentsen, H; Landrø, N I

2017-10-16

There is need for more efficient treatment of neurocognitive deficits in schizophrenia. In this 16 weeks randomised, placebo-controlled trial, we examined neurocognitive effects of adding ethyl-eicosapentaenoate 2g/day and/or vitamins E 364mg/day + C 1000mg/day to antipsychotics in 53 patients aged 18-39 years with acute schizophrenia. For the sake of validating neurocognitive tests, healthy subjects, not taking trial drugs, were also included in the study. Ethyl-EPA given alone to patients with low baseline RBC polyunsaturated fatty acids (PUFA), and Vitamins E+C given alone to high PUFA patients, impaired sustained attention (Continuous Performance Test, CPT-IP d prime score), standardised effect sizes d = 0.78 and d = 0.69, respectively. These adverse effects were paralleled by excessive increases in long-chain PUFA and serum alpha-tocopherol, respectively. They were counteracted by combining ethyl-EPA and vitamins, d = 0.80 and d = 0.74 in low and high PUFA patients, respectively. No other neurocognitive tests yielded significant results. Plausible mechanisms of harmful effects are oxidative stress and lipid raft disruption. Copyright © 2017. Published by Elsevier Ltd.

Characterization of volatile compounds of Mezcal, an ethnic alcoholic beverage obtained from Agave salmiana.

PubMed

De León-Rodríguez, Antonio; González-Hernández, Lidia; Barba de la Rosa, Ana P; Escalante-Minakata, Pilar; López, Mercedes G

2006-02-22

Commercial mezcals (white, white with worm, rested, rested with worm, and aged) produced from Agave salmiana were analyzed by solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS). Thirty-seven compounds were identified, and nine of them were classified as major compounds of mezcal (MCM). Saturated alcohols, ethyl acetate, ethyl 2-hydroxypropanoate, and acetic acid form the MCM group. Minor compounds of mezcal group include other alcohols, aldehydes, ketones, large chain ethyl esters, organic acids, furans, terpenes, alkenes, and alkynes. Most of the compounds found in mezcals in this study are similar to those present in tequilas and other alcoholic beverages. However, mezcals contain unique compounds such as limonene and pentyl butanoate, which can be used as markers for the authenticity of mezcal produced from A. salmiana.

Shewanella halifaxensis sp. nov., a novel obligately respiratory and denitrifying psychrophile.

PubMed

Zhao, Jian-Shen; Manno, Dominic; Leggiadro, Cindy; O'Neil, David; Hawari, Jalal

2006-01-01

Indigenous bacteria found in the sediment of the Emerald Basin (depth of 215 m, Atlantic Ocean) located offshore of Halifax Harbour (Nova Scotia, Canada) were previously found to be able to degrade the explosive compound hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX). In the present study, a novel obligately respiratory, denitrifying and RDX-mineralizing bacterium, designated strain HAW-EB4(T), was isolated from the marine sediment. This bacterium utilized peptone, yeast extract, Casamino acids, esters (Tweens 20, 40 and 80), sugars (N-acetyl-D-glucosamine, ribose), several C2 and C3 acids (acetate, pyruvate, lactate, propionate) and amino acids (serine, proline) as sole carbon and energy sources. Aerobically grown cells (in marine broth 2216 at 10 degrees C) contained C(14 : 0) (6 %), iso-C(15 : 0) (12 %), C(16 : 0) (20 %), C(16 : 1)omega7 (37 %), C(18 : 1)omega7 (7 %) and C(20 : 5)omega3 (7 %) as major membrane fatty acids, and Q7 (28.1 %) and MK-7 (60.9 %) as dominant respiratory quinones, consistent with deep-sea species of Shewanella. The novel bacterium had a DNA G+C content of 45 mol% and showed similarity to Shewanella species in terms of 16S rRNA and gyrB gene sequences (93-99 and 67.3-88.4 % similarity, respectively), with Shewanella pealeana being the most closely related species. Genomic DNA-DNA hybridization between strain HAW-EB4T and S. pealeana revealed a level of relatedness of 17.9 %, lower than the 70 % species cut-off value, indicating that strain HAW-EB4T (= NCIMB 14093T = DSM 17350T) is the type strain of a novel species of Shewanella, for which the name Shewanella halifaxensis sp. nov. is proposed.

Fatty acid ethyl ester synthase inhibition ameliorates ethanol-induced Ca2+-dependent mitochondrial dysfunction and acute pancreatitis

PubMed Central

Huang, Wei; Booth, David M; Cane, Matthew C; Chvanov, Michael; Javed, Muhammad A; Elliott, Victoria L; Armstrong, Jane A; Dingsdale, Hayley; Cash, Nicole; Li, Yan; Greenhalf, William; Mukherjee, Rajarshi; Kaphalia, Bhupendra S; Jaffar, Mohammed; Petersen, Ole H; Tepikin, Alexei V; Sutton, Robert; Criddle, David N

2014-01-01

Objective Non-oxidative metabolism of ethanol (NOME) produces fatty acid ethyl esters (FAEEs) via carboxylester lipase (CEL) and other enzyme action implicated in mitochondrial injury and acute pancreatitis (AP). This study investigated the relative importance of oxidative and non-oxidative pathways in mitochondrial dysfunction, pancreatic damage and development of alcoholic AP, and whether deleterious effects of NOME are preventable. Design Intracellular calcium ([Ca2+]C), NAD(P)H, mitochondrial membrane potential and activation of apoptotic and necrotic cell death pathways were examined in isolated pancreatic acinar cells in response to ethanol and/or palmitoleic acid (POA) in the presence or absence of 4-methylpyrazole (4-MP) to inhibit oxidative metabolism. A novel in vivo model of alcoholic AP induced by intraperitoneal administration of ethanol and POA was developed to assess the effects of manipulating alcohol metabolism. Results Inhibition of OME with 4-MP converted predominantly transient [Ca2+]C rises induced by low ethanol/POA combination to sustained elevations, with concurrent mitochondrial depolarisation, fall of NAD(P)H and cellular necrosis in vitro. All effects were prevented by 3-benzyl-6-chloro-2-pyrone (3-BCP), a CEL inhibitor. 3-BCP also significantly inhibited rises of pancreatic FAEE in vivo and ameliorated acute pancreatic damage and inflammation induced by administration of ethanol and POA to mice. Conclusions A combination of low ethanol and fatty acid that did not exert deleterious effects per se became toxic when oxidative metabolism was inhibited. The in vitro and in vivo damage was markedly inhibited by blockade of CEL, indicating the potential for development of specific therapy for treatment of alcoholic AP via inhibition of FAEE generation. PMID:24162590

Effects of Light and Temperature on Fatty Acid Production in Nannochloropsis Salina

DOE Office of Scientific and Technical Information (OSTI.GOV)

Van Wagenen, Jonathan M.; Miller, Tyler W.; Hobbs, Samuel J.

2012-03-12

Accurate prediction of algal biofuel yield will require empirical determination of physiological responses to the climate, particularly light and temperature. One strain of interest, Nannochloropsis salina, was subjected to ranges of light intensity (5-850 {mu}mol m{sup -2} s{sup -1}) and temperature (13-40 C); exponential growth rate, total fatty acids (TFA) and fatty acid composition were measured. The maximum acclimated growth rate was 1.3 day{sup -1} at 23 C and 250 {mu}mol m{sup -2} s{sup -1}. Fatty acids were detected by gas chromatography with flame ionization detection (GC-FID) after transesterification to corresponding fatty acid methyl esters (FAME). A sharp increase inmore » TFA containing elevated palmitic acid (C16:0) and palmitoleic acid (C16:1) during exponential growth at high light was observed, indicating likely triacylglycerol accumulation due to photo-oxidative stress. Lower light resulted in increases in the relative abundance of unsaturated fatty acids; in thin cultures, increases were observed in palmitoleic and eicosapentaenoeic acids (C20:5{omega}3). As cultures aged and the effective light intensity per cell converged to very low levels, fatty acid profiles became more similar and there was a notable increase of oleic acid (C18:1{omega}9). The amount of unsaturated fatty acids was inversely proportional to temperature, demonstrating physiological adaptations to increase membrane fluidity. This data will improve prediction of fatty acid characteristics and yields relevant to biofuel production.« less

7 Things to Know about Omega-3 Fatty Acids

MedlinePlus

... X Y Z 7 Things To Know About Omega-3 Fatty Acids Share: Omega-3 fatty acids are a group of polyunsaturated fatty ... a number of functions in the body. The omega-3 fatty acids EPA and DHA are found in ...

Breast milk docosahexaenoic acid (DHA) correlates with DHA status of malnourished infants.

PubMed

Smit, E N; Oelen, E A; Seerat, E; Muskiet, F A; Boersma, E R

2000-06-01

To investigate whether low docosahexaenoic acid (22:6omega3; DHA) status of malnourished, mostly breast fed infants is a result of low omega3 fatty acid intake via breast milk. Fatty acid composition of breast milk of eight Pakistani mothers, and of the erythrocytes of their malnourished children was analysed. The milk of the Pakistani mothers contained low percentages of all omega3 and most omega6 fatty acids, compared with milk of Dutch mothers. Breast milk DHA was positively correlated with infant erythrocyte DHA and arachidonic acid (20:4omega6). DHA status of these malnourished children is strongly dependent on the omega3 fatty acid intake from breast milk. Augmentation of the infants' omega3 long chain polyunsaturated fatty acid status, or the omega3 and omega6 fatty acid status in general, by supplementation is indicated in deprived circumstances where access to fresh fish is difficult. However, in terms of prevention, maternal supplementation of these long chain polyunsaturated fatty acids, preferably from early pregnancy onwards, may be a better option.

Structural and Epimeric Isomers of HPPH [3-Devinyl 3-{1-(1-hexyloxy) ethyl}pyropheophorbide-a]: Effects on Uptake and Photodynamic Therapy of Cancer.

PubMed

Saenz, Courtney; Cheruku, Ravindra R; Ohulchanskyy, Tymish Y; Joshi, Penny; Tabaczynski, Walter A; Missert, Joseph R; Chen, Yihui; Pera, Paula; Tracy, Erin; Marko, Aimee; Rohrbach, Daniel; Sunar, Ulas; Baumann, Heinz; Pandey, Ravindra K

2017-04-21

The tetrapyrrole structure of porphyrins used as photosentizing agents is thought to determine uptake and retention by malignant epithelial cancer cells. To assess the contribution of the oxidized state of individual rings to these cellular processes, bacteriochlorophyll a was converted into the ring "D" reduced 3-devinyl-3-[1-(1-hexyloxy)ethyl]pyropheophorbide-a (HPPH) and the corresponding ring "B" reduced isomer (iso-HPPH). The carboxylic acid analogs of both ring "B" and ring "D" reduced isomers showed several-fold higher accumulation into the mitochondria and endoplasmic reticulum by primary culture of human lung and head and neck cancer cells than the corresponding methyl ester analogs that localize primarily to granular vesicles and to a lesser extent to mitochondria. However, long-term cellular retention of these compounds exhibited an inverse relationship with tumor cells generally retaining better the methyl-ester derivatives. In vivo distribution and tumor uptake was evaluated in the isogenic model of BALB/c mice bearing Colon26 tumors using the respective 14 C-labeled analogs. Both carboxylic acid derivatives demonstrated similar intracellular localization and long-term tumor cure with no significant skin phototoxicity. PDT-mediated tumor action involved vascular damage, which was confirmed by a reduction in blood flow and immunohistochemical assessment of damage to the vascular endothelium. The HPPH stereoisomers (epimers) showed identical uptake (in vitro & in vivo), intracellular retention and photoreaction.

Rational selection of non-Saccharomyces wine yeasts for mixed starters based on ester formation and enological traits.

PubMed

Viana, Fernando; Gil, José V; Genovés, Salvador; Vallés, Salvador; Manzanares, Paloma

2008-09-01

Thirty-eight yeast strains belonging to the genera Candida, Hanseniaspora, Pichia, Torulaspora and Zygosaccharomyces were screened for ester formation on synthetic microbiological medium. The genera Hanseniaspora and Pichia stood out as the best acetate ester producers. Based on the ester profile Hanseniaspora guilliermondii 11027 and 11102, Hanseniaspora osmophila 1471 and Pichia membranifaciens 10113 and 10550 were selected for further characterization of enological traits. When growing on must H. osmophila 1471, which displayed a glucophilic nature and was able to consume more than 90% of initial must sugars, produced levels of acetic acid, medium chain fatty acids and ethyl acetate, within the ranges described for wine. On the other hand, it was found to be a strong producer of 2-phenylethyl acetate. Our data suggest that H. osmophila 1471 is a good candidate for mixed starters, although the possible interactions with S. cerevisiae deserve further research.

High enantiomeric excess of the flavor relevant 4-alkyl-branched Fatty acids in milk fat and subcutaneous adipose tissue of sheep and goat.

PubMed

Kaffarnik, Stefanie; Heid, Carolina; Kayademir, Yasemin; Eibler, Dorothee; Vetter, Walter

2015-01-21

Volatile 4-alkyl-branched fatty acids are characteristic flavor compounds of sheep and goat. Due to the methyl branch, the carbon C-4 represents a stereogenic center with the possible presence of one or both enantiomers in the respective samples. In this study, we used enantioselective gas chromatography to study the enantiomeric composition of 4-methyloctanoic acid (4-Me-8:0) and 4-ethyloctanoic acid (4-Et-8:0) in milk and dairy products from sheep and goat as well as in goat subcutaneous tissue. Different columns coated with modified cyclodextrins were tested to resolve racemic 4-alkyl-branched fatty acid methyl ester standards. The best enantiomer resolution was obtained on 25% octakis(2,3,6-tri-O-ethyl)-γ-cyclodextrin (γ-TECD) diluted in OV-1701. For analysis of the food samples, the lipids were extracted and fatty acids in the extracts were converted into fatty acid methyl esters. Non-aqueous reversed-phase high-performance liquid chromatography was used to fractionate the samples in order to gain one solution enriched in 4-Me-8:0 methyl ester and one solution enriched with 4-Et-8:0 methyl ester. Subsequent analysis by enantioselective gas chromatography with mass spectrometry allowed only the detection of one enantiomer of 4-Me-8:0 and 4-Et-8:0 in the samples. By means of a non-racemic standard of 4-Me-8:0, it was found that the predominant enantiomer was (R)-4-Me-8:0.

21 CFR 175.210 - Acrylate ester copolymer coating.

Code of Federal Regulations, 2014 CFR

2014-04-01

... polymerized copolymer of ethyl acrylate, methyl methacrylate, and methacrylic acid applied in emulsion form to... of the polymer and in the preparation and application of the emulsion may include substances named in... amount required as a preservative in emulsion defoamer. Disodium hydrogen phosphate Do. Formaldehyde...

Spectroscopy reveals that ethyl esters interact with proteins in wine.

PubMed

Di Gaspero, Mattia; Ruzza, Paolo; Hussain, Rohanah; Vincenzi, Simone; Biondi, Barbara; Gazzola, Diana; Siligardi, Giuliano; Curioni, Andrea

2017-02-15

Impairment of wine aroma after vinification is frequently associated to bentonite treatments and this can be the result of protein removal, as recently demonstrated for ethyl esters. To evaluate the existence of an interaction between wine proteins and ethyl esters, the effects induced by these fermentative aroma compounds on the secondary structure and stability of VVTL1, a Thaumatin-like protein purified from wine, was analyzed by Synchrotron Radiation Circular Dichroism (SRCD) spectroscopy. The secondary structure of wine VVTL1 was not strongly affected by the presence of selected ethyl esters. In contrast, VVTL1 stability was slightly increased by the addition of ethyl-octanoate, -decanoate and -dodecanoate, but decreased by ethyl-hexanoate. This indicates the existence of an interaction between VVTL1 and at least some aroma compounds produced during fermentation. The data suggest that proteins removal from wine by bentonite can result in indirect removal of at least some aroma compounds associated with them. Copyright © 2016 Elsevier Ltd. All rights reserved.

Effect of Vertical Shoot-Positioned, Scott-Henry, Geneva Double-Curtain, Arch-Cane, and Parral Training Systems on the Volatile Composition of Albariño Wines.

PubMed

Vilanova, Mar; Genisheva, Zlatina; Tubio, Miguel; Álvarez, Katia; Lissarrague, Jose Ramón; Oliveira, José Maria

2017-09-08

Viticultural practices influence both grape and wine quality. The influence of training systems on volatile composition was investigated for Albariño wine from Rías Baixas AOC in Northwest Spain. The odoriferous contribution of the compounds to the wine aroma was also studied. Volatile compounds belonging to ten groups (alcohols, C₆-compounds, ethyl esters, acetates, terpenols, C 13 -norisoprenoids, volatile phenols, volatile fatty acids, lactones and carbonyl compounds) were determined in Albariño wines from different training systems, Vertical Shoot-Positioned (VSP), Scott-Henry (SH), Geneva Double-Curtain (GDC), Arch-Cane (AC), and Parral (P) during 2010 and 2011 vintages. Wines from GDC showed the highest total volatile composition with the highest concentrations of alcohols, ethyl esters, fatty acids, and lactones families. However, the highest levels of terpenes and C 13 -norisoprenoids were quantified in the SH system. A fruitier aroma was observed in Albariño wines from GDC when odor activity values were calculated.

Nonaqueous gel for the transdermal delivery of a DTPA penta-ethyl ester prodrug.

PubMed

Zhang, Yong; Sadgrove, Matthew P; Sueda, Katsuhiko; Yang, Yu-Tsai; Pacyniak, Erik K; Kagel, John R; Braun, Brenda A; Zamboni, William C; Mumper, Russell J; Jay, Michael

2013-04-01

Diethylenetriamine pentaacetic acid penta-ethyl ester, designated as C2E5, was successfully incorporated into a nonaqueous gel for transdermal delivery. The thermal and rheological properties of a formulation containing 40% C2E5, 20% ethyl cellulose, and 40% Miglyol 840® prepared using the solvent evaporation method demonstrated that the gel had acceptable content uniformity and flow properties. In vitro studies showed that C2E5 was steadily released from the gel at a rate suitable for transdermal delivery. Topical application of the gel at a 200 mg C2E5/kg dose level in rats achieved significantly higher plasma exposures of several active metabolites compared with neat C2E5 oil at the same dose level. The results suggest that transdermal delivery of a chelator prodrug is an effective radionuclide decorporation strategy by delivering chelators to the circulation with a pharmacokinetic profile that is more consistent with the biokinetic profile of transuranic elements in contaminated individuals.

A computational search for lipases that can preferentially hydrolyze long-chain omega-3 fatty acids from fish oil triacylglycerols.

PubMed

Kamal, Md Zahid; Barrow, Colin J; Rao, Nalam Madhusudhana

2015-04-15

Consumption of long-chain omega-3 fatty acids is known to decrease the risk of major cardiovascular events. Lipases, a class of triacylglycerol hydrolases, have been extensively tested to concentrate omega-3 fatty acids from fish oils, under mild enzymatic conditions. However, no lipases with preference for omega-3 fatty acids selectivity have yet been discovered or developed. In this study we performed an exhaustive computational study of substrate-lipase interactions by docking, both covalent and non-covalent, for 38 lipases with a large number of structured triacylglycerols containing omega-3 fatty acids. We identified some lipases that have potential to preferentially hydrolyze omega-3 fatty acids from structured triacylglycerols. However omega-3 fatty acid preferences were found to be modest. Our study provides an explanation for absence of reports of lipases with omega-3 fatty acid hydrolyzing ability and suggests methods for developing these selective lipases. Copyright © 2014 Elsevier Ltd. All rights reserved.

A host-microbiome interaction mediates the opposing effects of omega-6 and omega-3 fatty acids on metabolic endotoxemia

PubMed Central

Kaliannan, Kanakaraju; Wang, Bin; Li, Xiang-Yong; Kim, Kui-Jin; Kang, Jing X.

2015-01-01

Metabolic endotoxemia, commonly derived from gut dysbiosis, is a primary cause of chronic low grade inflammation that underlies many chronic diseases. Here we show that mice fed a diet high in omega-6 fatty acids exhibit higher levels of metabolic endotoxemia and systemic low-grade inflammation, while transgenic conversion of tissue omega-6 to omega-3 fatty acids dramatically reduces endotoxemic and inflammatory status. These opposing effects of tissue omega-6 and omega-3 fatty acids can be eliminated by antibiotic treatment and animal co-housing, suggesting the involvement of the gut microbiota. Analysis of gut microbiota and fecal transfer revealed that elevated tissue omega-3 fatty acids enhance intestinal production and secretion of intestinal alkaline phosphatase (IAP), which induces changes in the gut bacteria composition resulting in decreased lipopolysaccharide production and gut permeability, and ultimately, reduced metabolic endotoxemia and inflammation. Our findings uncover an interaction between host tissue fatty acid composition and gut microbiota as a novel mechanism for the anti-inflammatory effect of omega-3 fatty acids. Given the excess of omega-6 and deficiency of omega-3 in the modern Western diet, the differential effects of tissue omega-6 and omega-3 fatty acids on gut microbiota and metabolic endotoxemia provide insight into the etiology and management of today’s health epidemics. PMID:26062993

A host-microbiome interaction mediates the opposing effects of omega-6 and omega-3 fatty acids on metabolic endotoxemia.

PubMed

Kaliannan, Kanakaraju; Wang, Bin; Li, Xiang-Yong; Kim, Kui-Jin; Kang, Jing X

2015-06-11

Metabolic endotoxemia, commonly derived from gut dysbiosis, is a primary cause of chronic low grade inflammation that underlies many chronic diseases. Here we show that mice fed a diet high in omega-6 fatty acids exhibit higher levels of metabolic endotoxemia and systemic low-grade inflammation, while transgenic conversion of tissue omega-6 to omega-3 fatty acids dramatically reduces endotoxemic and inflammatory status. These opposing effects of tissue omega-6 and omega-3 fatty acids can be eliminated by antibiotic treatment and animal co-housing, suggesting the involvement of the gut microbiota. Analysis of gut microbiota and fecal transfer revealed that elevated tissue omega-3 fatty acids enhance intestinal production and secretion of intestinal alkaline phosphatase (IAP), which induces changes in the gut bacteria composition resulting in decreased lipopolysaccharide production and gut permeability, and ultimately, reduced metabolic endotoxemia and inflammation. Our findings uncover an interaction between host tissue fatty acid composition and gut microbiota as a novel mechanism for the anti-inflammatory effect of omega-3 fatty acids. Given the excess of omega-6 and deficiency of omega-3 in the modern Western diet, the differential effects of tissue omega-6 and omega-3 fatty acids on gut microbiota and metabolic endotoxemia provide insight into the etiology and management of today's health epidemics.

Dietary supplementation of finishing pigs with the docosahexaenoic acid-rich microalgae, Aurantiochytrium limacinum: effects on performance, carcass characteristics and tissue fatty acid profile

PubMed Central

2018-01-01

Objective The aim of this experiment was to evaluate the effect of dietary supplementation with the docosahexaenoic acid (DHA)-rich microalgae, Aurantiochytrium limacinum (AURA) on pig performance, carcass traits, and the fatty acid composition of pork Longissimus lumborum (LL) and backfat. Methods A total of 144 Pig Improvement Company (PIC)×Goland finishing pigs (72 females and 72 castrated males) of mean weight 117.1 (±13.1) kg were blocked by sex and body weight and provided with 0% or 1% AURA in isonutritive and isocaloric diets. A total of 24 pens provided 12 replicates per treatment. Animals were weighed on day 0 and 28 with feed and water intake recorded per pen. After 31 days supplementation (28 days of study and 3 days until the slaughtering date) three animals per pen (n = 72) were slaughtered and the LL and backfat thickness, lean meat content and dressing percentage were recorded for the carcasses. The fatty acid (FA) profile of the LL and backfat was established by direct FA methyl ester synthesis. Results No differences were observed for any performance parameters or carcass traits. Supplementation with AURA resulted in significant changes to the FA profiles of both the LL and backfat with male and female pigs responding differently to supplementation in terms of particular FAs. Overall, pork LL samples had significantly higher eicosapentaenoic acid (p<0.001) and DHA concentrations (p<0.001), and higher omega-3 (n-3) FAs (p<0.001), as well as an increased omega3:omega6 (n-3:n-6) ratio (p = 0.001). For backfat, supplementation resulted in significantly higher amounts of DHA (p<0.001) and n-3 FAs (p<0.001). Conclusion These results indicate that dietary supplementation with 1% AURA over a 31 day period can increase the FA composition of pork LL and backfat, specifically the DHA, with no major impact on growth performance and carcass traits. PMID:29381901

Dietary supplementation of finishing pigs with the docosahexaenoic acid-rich microalgae, Aurantiochytrium limacinum: effects on performance, carcass characteristics and tissue fatty acid profile.

PubMed

Moran, Colm A; Morlacchini, Mauro; Keegan, Jason D; Fusconi, Giorgio

2018-05-01

The aim of this experiment was to evaluate the effect of dietary supplementation with the docosahexaenoic acid (DHA)-rich microalgae, Aurantiochytrium limacinum (AURA) on pig performance, carcass traits, and the fatty acid composition of pork Longissimus lumborum (LL) and backfat. A total of 144 Pig Improvement Company (PIC)×Goland finishing pigs (72 females and 72 castrated males) of mean weight 117.1 (±13.1) kg were blocked by sex and body weight and provided with 0% or 1% AURA in isonutritive and isocaloric diets. A total of 24 pens provided 12 replicates per treatment. Animals were weighed on day 0 and 28 with feed and water intake recorded per pen. After 31 days supplementation (28 days of study and 3 days until the slaughtering date) three animals per pen (n = 72) were slaughtered and the LL and backfat thickness, lean meat content and dressing percentage were recorded for the carcasses. The fatty acid (FA) profile of the LL and backfat was established by direct FA methyl ester synthesis. No differences were observed for any performance parameters or carcass traits. Supplementation with AURA resulted in significant changes to the FA profiles of both the LL and backfat with male and female pigs responding differently to supplementation in terms of particular FAs. Overall, pork LL samples had significantly higher eicosapentaenoic acid (p<0.001) and DHA concentrations (p<0.001), and higher omega-3 (n-3) FAs (p<0.001), as well as an increased omega3:omega6 (n-3:n-6) ratio (p = 0.001). For backfat, supplementation resulted in significantly higher amounts of DHA (p<0.001) and n-3 FAs (p<0.001). These results indicate that dietary supplementation with 1% AURA over a 31 day period can increase the FA composition of pork LL and backfat, specifically the DHA, with no major impact on growth performance and carcass traits.

An efficient synthesis of the constrained peptidomimetic 2-oxo-3-(N-9-fluorenyloxycarbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid from pyroglutamic acid.

PubMed

Mandal, Pijus Kumar; Kaluarachchi, Kumar K; Ogrin, Douglas; Bott, Simon G; McMurray, John S

2005-11-25

[reaction: see text] Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo[4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.

Omega-3 and omega-6 Fatty acids in blood and breast tissue of high-risk women and association with atypical cytomorphology.

PubMed

Hidaka, Brandon H; Li, Shengqi; Harvey, Katherine E; Carlson, Susan E; Sullivan, Debra K; Kimler, Bruce F; Zalles, Carola M; Fabian, Carol J

2015-05-01

The ratio of omega-3 to omega-6 fatty acids, especially the long-chain eicosapentaenoic acid (EPA) + docosahexaenoic acid (DHA) to arachidonic acid (AA) ratio, is inversely associated with breast cancer risk. We measured the association between cytologic atypia, a biomarker for short-term risk of breast cancer development, and omega-3 and omega-6 fatty acid intake and levels in blood and breast tissue. Blood and benign breast tissue, sampled by random periareolar fine-needle aspiration (RPFNA), was obtained from 70 women at elevated risk for breast cancer. Self-reported dietary intake was assessed by the NCI's Food Frequency Questionnaire. The fatty acid composition of five lipid compartments, red blood cell, plasma and breast phospholipids, and plasma and breast triaclyglycerides (TAG), was analyzed by gas chromatography as weight percent. Median daily intakes of EPA+DHA and total omega-3 fatty acids were 80 mg and 1.1 g, respectively. The median total omega-3:6 intake ratio was 1:10. Compared with women without atypia, those with cytologic atypia had lower total omega-3 fatty acids in red blood cell and plasma phospholipids and lower omega-3:6 ratios in plasma TAGs and breast TAGs (P < 0.05). The EPA+DHA:AA ratio in plasma TAGs was also lower among women with atypia. This is the first report of associations between tissue levels of omega-3 and omega-6 fatty acids and a reversible tissue biomarker of breast cancer risk. RPFNA cytomorphology could serve as a surrogate endpoint for breast cancer prevention trials of omega-3 fatty acid supplementation. ©2015 American Association for Cancer Research.

Evaluating the Intoxicating Degree of Liquor Products with Combinations of Fusel Alcohols, Acids, and Esters.

PubMed

Xie, Jia; Tian, Xiao-Fei; He, Song-Gui; Wei, Yun-Lu; Peng, Bin; Wu, Zhen-Qiang

2018-05-23

To investigate the effects of fusel alcohols on the intoxicating degree of liquor products, formulated liquors (FLs) were prepared by blending 1-propanol, isobutanol, and isoamyl alcohol with ethanol, organic acids, and corresponding ethyl esters to simulate the formula of traditional Chinese liquors. The prepared FLs were submitted for evaluation of their intoxicating degree (ID). The results showed that the fusel alcohols had a biphasic effect on the IDs of the FLs, depending on the comprehensive coordination of the characteristic minor components. The importance of the suitable ratio of alcohols/acids/esters (RAAE) on the IDs was also revealed. Under an optimal ratio level, the fusel alcohols exhibited negligible effects on the IDs of the FLs. Moreover, the ratio of isoamyl alcohol to isobutanol (IA/IB) showed a strong positive correlation to the IDs of the FLs. This study lays a foundation for the potential application in producing low-ID liquor.

Volatile compounds and odor traits of dry-cured ham (Prosciutto crudo) irradiated by electron beam and gamma rays

NASA Astrophysics Data System (ADS)

Kong, Qiulian; Yan, Weiqiang; Yue, Ling; Chen, Zhijun; Wang, Haihong; Qi, Wenyuan; He, Xiaohua

2017-01-01

Prosciutto crudo samples were irradiated at 0, 3 and 6 kGy by gamma rays (GR) and electron beam (EB), respectively. The odor scores and volatile compounds were examined after 7 days storage at 4 °C. Volatile compounds from samples without and with irradiation at 6 kGy were analyzed by GC-MS. Fifty-nine compounds were identified, including terpenes, aldehydes, alcohols, ketones, alkanes, esters, aromatic hydrocarbons and acids. Both GR and EB irradiation resulted in formation of (Z)-7-Hexadecenal, cis-9-hexadecenal, tetradecane, E-9-tetradecen-1-ol formate, and losing of hexadecamethyl-heptasiloxane and decanoic acid-ethyl ester in hams. However, GR irradiation caused additional changes, such as formation of undecane and phthalic acid-2-cyclohexylethyl butyl ester, significantly higher level of 1-pentadecene, and losing of (E, E)-2,4-decadienal and octadecane. EB was shown to be better in maintaining ham's original odor than GR. Our results suggest that EB irradiation is a promising method for treatment of ready to eat hams as it exerts much less negative effect on the flavor of hams compared to GR irradiation.

Composition and antimicrobial activity of the essential oil from the branches of Jacaranda cuspidifolia Mart. growing in Sichuan, China.

PubMed

Yuan, Juanjuan; Gan, Tian; Liu, Yingtian; Gao, Hui; Xu, Weifeng; Zhang, Tao; Tan, Rui; Cai, Zhenghong; Jiang, Hezhong

2018-06-01

This study represents the first report on the chemical composition and antimicrobial activity of the essential oil from the branches of Jacaranda cuspidifolia Mart. Thirty-three compounds were identified by Gas Chromatography-Mass Spectrometry (GC-MS) and the major constituents of the essential oil were Palmitic acid (31.36%), (Z) - 9,17-Octadecadienal (12.06%), Ethyl palmitate (3.81%), Perhydrofarnesyl acetone (2.07%), γ-Maaliene (1.88%), and Cedro (1.42%) and 9,12-Octadecadienoic acid ethyl ester (1.42%). The in vitro antimicrobial activities of the essential oil were evaluated by the disc diffusion method, and the inhibition zones against Escherichia coli, Staphylococcus aureus and Candida albicans were 7.10, 8.20 and 7.25 mm, respectively. The oil showed moderate activities against E. coli, S. aureus and C. albicans with minimum inhibition concentration (MIC) values of 17.3 mg/mL, 12.9 mg/mL and 16.0 mg/mL, respectively.

Evaluation of mosquito larvicidal activity of fruit extracts of Acacia auriculiformis against the Japanese encephalitis vector Culex vishnui.

PubMed

Barik, Mousumi; Rawani, Anjali; Laskar, Subrata; Chandra, Goutam

2018-02-19

The larvicidal potentiality of crude and ethyl acetate extracts of fruits of Acacia auriculiformis was investigated against all the larval instars of JE vector Culex vishnui. The crude extracts showed good results against all the larval instars with highest mortality at 0.09%. Highest mortality was found at 300 ppm of ethyl acetate extract. Lowest LC 50 value was obtained at 72 h for third instar larvae. Non target organisms tested, showed no to very less mortality to ethyl acetate solvent extract. Presence of N-H stretching, a C=O stretching, C=C and C-N stretching vibrations of secondary amide or amine group were confirmed from IR analysis. GC-MS analysis revealed the presence of three compounds namely Ethane 2-chloro-1,1-dimethoxy, Acetic acid, 1-methyl ether ester and [4-[1-[3,5-Dimethyl-4[(trimethylsilyl)oxy)phenyl]-1,3-dimethylbutyl)-2,6dimethylphenoxy)(trimethyl) silane, responsible for mosquito larval death.

EDC-mediated DNA attachment to nanocrystalline CVD diamond films.

PubMed

Christiaens, P; Vermeeren, V; Wenmackers, S; Daenen, M; Haenen, K; Nesládek, M; vandeVen, M; Ameloot, M; Michiels, L; Wagner, P

2006-08-15

Chemical vapour deposited (CVD) diamond is a very promising material for biosensor fabrication owing both to its chemical inertness and the ability to make it electrical semiconducting that allows for connection with integrated circuits. For biosensor construction, a biochemical method to immobilize nucleic acids to a diamond surface has been developed. Nanocrystalline diamond is grown using microwave plasma-enhanced chemical vapour deposition (MPECVD). After hydrogenation of the surface, 10-undecenoic acid, an omega-unsaturated fatty acid, is tethered by 254 nm photochemical attachment. This is followed by 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide (EDC)-mediated attachment of amino (NH(2))-modified dsDNA. The functionality of the covalently bound dsDNA molecules is confirmed by fluorescence measurements, PCR and gel electrophoresis during 35 denaturation and rehybridisation steps. The linking method after the fatty acid attachment can easily be applied to other biomolecules like antibodies and enzymes.

Omega-3 fatty acids (image)

MedlinePlus

Omega-3 fatty acids are a form of polyunsaturated fat that the body derives from food. Omega-3s (and omega-6s) are known as essential fatty acids (EFAs) because they are important for good health. ...

Mechanism of alpha-amino acids decomposition in the gas phase. experimental and theoretical study of the elimination kinetics of N-benzyl glycine ethyl ester.

PubMed

Tosta, Maria; Oliveros, Jhenny C; Mora, Jose R; Córdova, Tania; Chuchani, Gabriel

2010-02-25

The gas-phase elimination kinetics of N-benzylglycine ethyl ester was examined in a static system, seasoned with allyl bromide, and in the presence of the free chain radical suppressor toluene. The working temperature and pressure range were 386.4-426.7 degrees C and 16.7-40.0 torr, respectively. The reaction showed to be homogeneous, unimolecular, and obeys a first-order rate law. The elimination products are benzylglycine and ethylene. However, the intermediate benzylglycine is unstable under the reaction conditions decomposing into benzyl methylamine and CO(2) gas. The variation of the rate coefficients with temperature is expressed by the following Arrhenius equation: log k(1) (s(-1)) = (11.83 +/- 0.52) - (190.3 +/- 6.9) kJ mol(-1) (2.303RT)(-1). The theoretical calculation of the kinetic parameters and mechanism of elimination of this ester were performed at B3LYP/6-31G*, B3LYP/6-31+G**, MPW1PW91/6-31G*, and MPW1PW91/6-31+G** levels of theory. The calculation results suggest a molecular mechanism of a concerted nonsynchronous six-membered cyclic transition state process. The analysis of bond order and natural bond orbital charges implies that the bond polarization of C(=O)O-C, in the sense of C(=O)O(delta-)...C(delta+), is rate determining. The experimental and theoretical parameters have been found to be in reasonable agreement.

Solid-phase microextraction may catalize hydrogenation when using hydrogen as carrier in gas chromatography.

PubMed

Fiorini, D; Boarelli, M C

2016-07-01

When hydrogen is used as carrier gas, carbon-carbon double bonds may be hydrogenated in the hot gas chromatograph (GC) injector if introduced by solid-phase microextraction (SPME). SPME fibers coated with polydimethylsiloxane (PDMS)/carboxen/divinylbenzene (DVB), PDMS/carboxen, polyacrylate, PDMS/DVB and PDMS on fused silica, stableflex or metal alloy core have been tested with fatty acid methyl esters (FAMEs) from olive oil. Using coatings containing DVB, hydrogenation took place with high conversion rates (82.0-92.9%) independently of the core material. With all fibers having a metal core, hydrogenation was observed to a certain extent (27.4-85.3%). PDMS, PDMS/carboxen and polyacrylate coated fibers with a fused silica or stableflex core resulted in negligible hydrogenation (0.2-2.5%). The occurrence of hydrogenation was confirmed also with other substances containing carbon-carbon double bonds (n-alkenes, alkenoic acids, mono- and polyunsaturated fatty acid methyl and ethyl esters). Copyright © 2016 Elsevier B.V. All rights reserved.

Gene-diet interaction of a common FADS1 variant with marine polyunsaturated fatty acids for fatty acid composition in plasma and erythrocytes among men.

PubMed

Takkunen, Markus J; de Mello, Vanessa D; Schwab, Ursula S; Kuusisto, Johanna; Vaittinen, Maija; Ågren, Jyrki J; Laakso, Markku; Pihlajamäki, Jussi; Uusitupa, Matti I J

2016-02-01

Limited information exists on how the relationship between dietary intake of fat and fatty acids in erythrocytes and plasma is modulated by polymorphisms in the FADS gene cluster. We examined gene-diet interaction of total marine PUFA intake with a known gene encoding Δ-5 desaturase enzyme (FADS1) variant (rs174550) for fatty acids in erythrocyte membranes and plasma phospholipids (PL), cholesteryl esters (CE), and triglycerides (TG). In this cross-sectional study, fatty acid compositions were measured using GC, and total intake of polyunsaturated fat from fish and fish oil was estimated using a food frequency questionnaire in a subsample (n = 962) of the Metabolic Syndrome in Men Study. We found nominally significant gene-diet interactions for eicosapentaenoic acid (EPA, 20:5n-3) in erythrocytes (pinteraction = 0.032) and for EPA in plasma PL (pinteraction = 0.062), CE (pinteraction = 0.035), and TG (pinteraction = 0.035), as well as for docosapentaenoic acid (22:5n-3) in PL (pinteraction = 0.007). After excluding omega-3 supplement users, we found a significant gene-diet interaction for EPA in erythrocytes (pinteraction < 0.003). In a separate cohort of the Kuopio Obesity Surgery Study, the same locus was strongly associated with hepatic mRNA expression of FADS1 (p = 1.5 × 10(-10) ). FADS1 variants may modulate the relationship between marine fatty acid intake and circulating levels of long-chain omega-3 fatty acids. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Experimental investigation of the auto-ignition characteristics of oxygenated reference fuel compounds

NASA Astrophysics Data System (ADS)

Walton, Stephen Michael

The increased use of biofuels presents an opportunity to improve combustion performance while simultaneously reducing greenhouse gases and pollutant emissions. This work focused on improving the fundamental understanding of the auto-ignition chemistry of oxygenated reference fuel compounds. A systematic study of the effects of ester structure on ignition chemistry was performed using the University of Michigan Rapid Compression Facility. The ignition properties of the ester compounds were investigated over a broad range of pressures (P=5-20 atm) and temperatures (T=850-1150 K) which are directly relevant to advanced combustion engine strategies. Ignition delay times for five esters were determined using the RCF. The esters were selected to systematically consider the chemical structure of the compounds. Three esters were saturated: methyl butanoate, butyl methanoate, and ethyl propanoate; and two were unsaturated: methyl crotonate and methyl trans-3-hexenoate. The unsaturated esters were more reactive than their saturated counterparts, with the largest unsaturated ester, methyl trans-3-hexenoate having the highest reactivity. Two isomers of the saturated esters, butyl methanoate and ethyl propanoate, were more reactive than the isomer methyl butanoate. The results are explained if we assume that butyl methanoate and ethyl propanoate form intermediate ring structures which decompose more rapidly than esters such as methyl butanoate, which do not form ring structures. Modeling studies of the reaction chemistry were conducted for methyl butanoate and ethyl propanoate, for which detailed mechanisms were available in the literature. The new experimental data indicated that literature rate coefficients for some of the methyl butanoate/HO2 reactions were too fast. Modifying these within the theoretical uncertainties for the reaction rates, led to excellent agreement between the model predictions and the experimental data. Comparison of the modeling results with the intermediates measured during methyl butanoate ignition indicated that pathways leading to the formation of small hydrocarbons are relatively well represented in the reaction mechanism. The results of this work provide archival benchmark data for improved understanding of the dominant reaction pathways and species controlling the auto-ignition of oxygenated reference fuel compounds. These data also provide a path for continued development of chemical kinetic models to optimize practical combustion systems.

Gallic acid-based alkyl esters synthesis in a water-free system by celite-bound lipase of Bacillus licheniformis SCD11501.

PubMed

Sharma, Shivika; Kanwar, Shamsher S; Dogra, Priyanka; Chauhan, Ghanshyam S

2015-01-01

Gallic acid (3, 4, 5- trihydroxybenzoic acid) is an important antioxidant, anti-inflammatory, and radical scavenging agent. In the present study, a purified thermo-tolerant extra-cellular lipase of Bacillus licheniformis SCD11501 was successfully immobilized by adsorption on Celite 545 gel matrix followed by treatment with a cross-linking agent, glutaraldehyde. The celite-bound lipase treated with glutaraldehyde showed 94.8% binding/retention of enzyme activity (36 U/g; specific activity 16.8 U/g matrix; relative increase in enzyme activity 64.7%) while untreated matrix resulted in 88.1% binding/retention (28.0 U/g matrix; specific activity 8.5 U/g matrix) of lipase. The celite-bound lipase was successfully used to synthesis methyl gallate (58.2%), ethyl gallate (66.9%), n-propyl gallate (72.1%), and n-butyl gallate (63.8%) at 55(o) C in 10 h under shaking (150 g) in a water-free system by sequentially optimizing various reaction parameters. The low conversion of more polar alcohols such as methanol and ethanol into their respective gallate esters might be due to the ability of these alcohols to severely remove water from the protein hydration shell, leading to enzyme inactivation. Molecular sieves added to the reaction mixture resulted in enhanced yield of the alkyl ester(s). The characterization of synthesised esters was done through fourier transform infrared (FTIR) spectroscopy and (1) H NMR spectrum analysis. © 2015 American Institute of Chemical Engineers.

An ab initio density functional study of the optical functions of 9-Methyl-3-Thiophen-2-YI-Thieno [3,2e] [1,2,4] Thriazolo [4,3c] Pyrimidine-8-Carboxylic Acid Ethyl Ester crystals.

PubMed

Reshak, Ali H; Kityk, I V; Khenata, R; Al-Douri, Y; Auluck, S

2012-09-01

An ab initio investigation of the optical constants of 9-Methyl-3-Thiophen-2-YI-Thieno [3,2e] [1,2,4] Thriazolo [4,3c] Pyrimidine-8-Carboxylic Acid Ethyl Ester crystal is performed within a framework of local density approximation (LDA), and the Engel-Vosko generalized gradient approximation (EV-GGA) exchange correlation potentials. It is established that there are two independent molecules (A and B) exhibiting different intra-molecular interactions: C-H⋯O (A) and C-H⋯N (B). These intra-molecular interactions favor stabilization of the crystal structure for molecules A and B. It should be emphasized that there exist remarkable π-π interactions between the pyrimidine rings of the two neighbors B molecules giving extra strengths and stabilizations to the superamolecular structure. These different intra-molecular interactions C-H⋯O (A) and C-H⋯N (B) and the π-π interaction between the pyrimidine rings of the two neighbors B molecules give principal contribution to dispersion of optical properties. With a view to seek deeper insight into the electronic structure, the optical properties were investigated. Our calculations show that the optical constants are very anisotropic. The EVGGA calculation shows a blue spectral shift of around 0.024 eV with significant changes in the spectra compared to the LDA calculation. The observed spectral shifts are in agreement with the calculated band structure and corresponding electron density of states. Copyright © 2012 Elsevier B.V. All rights reserved.

Oxygen-induced excitability of the belousov-zhabotinskii oscillatory system

NASA Astrophysics Data System (ADS)

Treindl, Ľudovit; Mrákavová, Marta

1985-12-01

The modified Belousov-Zhabotinskii ferroin-catalyzed oscillatory system with the ethyl ester of 3-oxobutanoic acid is described. After an induction period of about 120 s its oscillatory state consisting of four or five oscillations of absorbancy at a wavenumber of 22×10 3 cm -1 can be revived three or four times, if the solution is shaken for 25 s after the oscillatory state has finished. This apparently "mechanical" excitability, which can be observed spectrophotometrically and also polarographically using a rotating platinum disc electrode, proved to be oxygen-induced.

Nuts and Your Heart: Eating Nuts for Heart Health

MedlinePlus

... monounsaturated and polyunsaturated fats — lower bad cholesterol levels. Omega-3 fatty acids. Omega-3 fatty acids are found in many kinds of fish, but many nuts are also rich in omega-3 fatty acids. Omega-3s are a healthy form ...

Influence of Omega-3 Fatty Acid Status on the Way Rats Adapt to Chronic Restraint Stress

PubMed Central

Hennebelle, Marie; Balasse, Laure; Latour, Alizée; Champeil-Potokar, Gaelle; Denis, Stéphanie; Lavialle, Monique; Gisquet-Verrier, Pascale; Denis, Isabelle; Vancassel, Sylvie

2012-01-01

Omega-3 fatty acids are important for several neuronal and cognitive functions. Altered omega-3 fatty acid status has been implicated in reduced resistance to stress and mood disorders. We therefore evaluated the effects of repeated restraint stress (6 h/day for 21 days) on adult rats fed omega-3 deficient, control or omega-3 enriched diets from conception. We measured body weight, plasma corticosterone and hippocampus glucocorticoid receptors and correlated these data with emotional and depression-like behaviour assessed by their open-field (OF) activity, anxiety in the elevated-plus maze (EPM), the sucrose preference test and the startle response. We also determined their plasma and brain membrane lipid profiles by gas chromatography. Repeated restraint stress caused rats fed a control diet to lose weight. Their plasma corticosterone increased and they showed moderate behavioural changes, with increases only in grooming (OF test) and entries into the open arms (EPM). Rats fed the omega-3 enriched diet had a lower stress-induced weight loss and plasma corticosterone peak, and reduced grooming. Rats chronically lacking omega-3 fatty acid exhibited an increased startle response, a stress-induced decrease in locomotor activity and exaggerated grooming. The brain omega-3 fatty acids increased as the dietary omega-3 fatty acids increased; diets containing preformed long-chain omega-3 fatty acid were better than diets containing the precursor alpha-linolenic acid. However, the restraint stress reduced the amounts of omega-3 incorporated. These data showed that the response to chronic restraint stress was modulated by the omega-3 fatty acid supply, a dietary deficiency was deleterious while enrichment protecting against stress. PMID:22860066

How 'ground-picked' olive fruits affect virgin olive oil ethanol content, ethyl esters and quality.

PubMed

Beltran, Gabriel; Sánchez, Raquel; Sánchez-Ortiz, Araceli; Aguilera, Maria P; Bejaoui, Mohamed A; Jimenez, Antonio

2016-08-01

Olives dropped on the ground naturally sometimes are not separated from those fresh and healthy collected from the tree for harvest and processing. In this work we compared the quality, ethanol content and bioactive components of virgin olive oils from ground-picked olives, tree-picked fruits and their mixture. Ground-picked olives produced 'Lampante' virgin olive oils; these are of a lower quality category, because of important alterations in chemical and sensory characteristics. Ethyl esters showed the highest values, although under the regulated limit. The mixture of ground and tree-picked olives gave oils classified as 'virgin' because of sensory defects, although the quality parameters did not exceed the limits for the 'extra' category. Ethanol content showed a significant increase in the oils from ground- picked olives and their mixture with respect to those from tree-picked fruits. Furthermore, bioactive compounds showed a significant decrease as fruit quality was poorer. Ground-picked olives must be harvested and processed separately since they produce low-quality virgin olive oils with sensory defects and lower concentrations of bioactive compounds. The higher acidity and ethanol concentration observed in oils from ground-picked fruits or their mixture may help ethyl ester synthesis during storage. © 2015 Society of Chemical Industry. © 2015 Society of Chemical Industry.

Enzymatic synthesis of ethyl esters from waste oil using mixtures of lipases in a plug-flow packed-bed continuous reactor.

PubMed

Kathiele Poppe, Jakeline; Matte, Carla Roberta; Olave de Freitas, Vitória; Fernandez-Lafuente, Roberto; Rodrigues, Rafael C; Záchia Ayub, Marco Antônio

2018-04-30

This work describes the continuous synthesis of ethyl esters via enzymatic catalysis on a packed-bed continuous reactor, using mixtures of immobilized lipases (combi-lipases) of Candida antarctica (CALB), Thermomyces lanuginosus (TLL), and Rhizomucor miehei (RML). The influence of the addition of glass beads to the reactor bed, evaluation of the use of different solvents, and flow rate on reaction conditions were studied. All experiments were conducted using the best combination of lipases according to the fatty acid composition of the waste oil (combi-lipase composition: 40% of TLL, 35% of CALB, and 25% of RML), and soybean oil (combi-lipase composition: 22.5% of TLL, 50% of CALB, and 27.5% of RML). The best general reaction conditions were found to be using tert-butanol as solvent, and the flow rate of 0.08 mL min -1 . The combi-lipase reactors operating at steady state for over 30 days (720 h), kept conversion yields of approximately 50%, with average productivity of 1.94 g ethyl esters g substrate -1 h -1 , regardless of the type of oil in use. This article is protected by copyright. All rights reserved. © 2018 American Institute of Chemical Engineers.

Predictors of Memory in Healthy Aging: Polyunsaturated Fatty Acid Balance and Fornix White Matter Integrity.

PubMed

Zamroziewicz, Marta K; Paul, Erick J; Zwilling, Chris E; Barbey, Aron K

2017-07-01

Recent evidence demonstrates that age and disease-related decline in cognition depends not only upon degeneration in brain structure and function, but also on dietary intake and nutritional status. Memory, a potential preclinical marker of Alzheimer's disease, is supported by white matter integrity in the brain and dietary patterns high in omega-3 and omega-6 polyunsaturated fatty acids. However, the extent to which memory is supported by specific omega-3 and omega-6 polyunsaturated fatty acids, and the degree to which this relationship is reliant upon microstructure of particular white matter regions is not known. This study therefore examined the cross-sectional relationship between empirically-derived patterns of omega-3 and omega-6 polyunsaturated fatty acids (represented by nutrient biomarker patterns), memory, and regional white matter microstructure in healthy, older adults. We measured thirteen plasma phospholipid omega-3 and omega-6 polyunsaturated fatty acids, memory, and regional white matter microstructure in 94 cognitively intact older adults (65 to 75 years old). A three-step mediation analysis was implemented using multivariate linear regressions, adjusted for age, gender, education, income, depression status, and body mass index. The mediation analysis revealed that a mixture of plasma phospholipid omega-3 and omega-6 polyunsaturated fatty acids is linked to memory and that white matter microstructure of the fornix fully mediates the relationship between this pattern of plasma phospholipid polyunsaturated fatty acids and memory. These results suggest that memory may be optimally supported by a balance of plasma phospholipid omega-3 and omega-6 polyunsaturated fatty acids through the preservation of fornix white matter microstructure in cognitively intact older adults. This report provides novel evidence for the benefits of plasma phospholipid omega-3 and omega-6 polyunsaturated fatty acid balance on memory and underlying white matter microstructure.

Eco-friendly methodology for efficient synthesis and scale-up of 2-ethylhexyl-p-methoxycinnamate using Rhizopus oryzae lipase and its biological evaluation.

PubMed

Kumar, Vinod; Jahan, Firdaus; Kameswaran, Karthikeya; Mahajan, Richi V; Saxena, Rajendra Kumar

2014-06-01

Lipase-mediated synthesis of phenolic acid esters is a green and economical alternative to current chemical methods. Octyl methoxycinnamate, an important UVB-absorbing compound, was synthesized by the esterification of p-methoxycinnamic acid with 2-ethyl hexanol using Rhizopus oryzae lipase. A molar ratio of 1:2 of p-methoxycinnamic acid and 2-ethyl hexanol was found to give an optimum yield using cyclo-octane (50 ml) as reaction solvent, at a temperature of 45 °C, and 750 U of lipase, resulting in a yield of 91.3 % in 96 h. This reaction was successfully scaled up to 400-ml reaction size where 88.6 %bioconversion was achieved. The synthesized compound was found to have superior antioxidant activity as compared to ascorbic acid. The synthesized compound also exhibited good antimicrobial activity against Escherichia coli, Klebsiella pneumonia, Salmonella typhi, Staphylococcus aures, Candida albicans (yeast), Aspergillus niger, Alternaria solani, and Fussarium oxysporum by well diffusion method in terms of zone of inhibitions (in mm).

In chronic fatigue syndrome, the decreased levels of omega-3 poly-unsaturated fatty acids are related to lowered serum zinc and defects in T cell activation.

PubMed

Maes, Michael; Mihaylova, Ivana; Leunis, Jean-Claude

2005-12-01

There is now evidence that major depression is accompanied by decreased levels of omega3 poly-unsaturated fatty acids (PUFA), such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). There is a strong comorbidity between major depression and chronic fatigue syndrome (CFS). The present study has been carried out in order to examine PUFA levels in CFS. In twenty-two CFS patients and 12 normal controls we measured serum PUFA levels using gas chromatography and mass spectrometry. We found that CFS was accompanied by increased levels of omega6 PUFAs, i.e. linoleic acid and arachidonic acid (AA), and mono-unsaturated fatty acids (MUFAs), i.e. oleic acid. The EPA/AA and total omega3/omega6 ratios were significantly lower in CFS patients than in normal controls. The omega3/omega6 ratio was significantly and negatively correlated to the severity of illness and some items of the FibroFatigue scale, i.e. aches and pain, fatigue and failing memory. The severity of illness was significantly and positively correlated to linoleic and arachidonic acid, oleic acid, omega9 fatty acids and one of the saturated fatty acids, i.e. palmitic acid. In CFS subjects, we found significant positive correlations between the omega3/omega6 ratio and lowered serum zinc levels and the lowered mitogen-stimulated CD69 expression on CD3+, CD3+ CD4+, and CD3+ CD8+ T cells, which indicate defects in early T cell activation. The results of this study show that a decreased availability of omega3 PUFAs plays a role in the pathophysiology of CFS and is related to the immune pathophysiology of CFS. The results suggest that patients with CFS should respond favourably to treatment with--amongst other things--omega3 PUFAs, such as EPA and DHA.

Proteins involved in wine aroma compounds metabolism by a Saccharomyces cerevisiae flor-velum yeast strain grown in two conditions.

PubMed

Moreno-García, Jaime; García-Martínez, Teresa; Millán, M Carmen; Mauricio, Juan Carlos; Moreno, Juan

2015-10-01

A proteomic and exometabolomic study was conducted on Saccharomyces cerevisiae flor yeast strain growing under biofilm formation condition (BFC) with ethanol and glycerol as carbon sources and results were compared with those obtained under no biofilm formation condition (NBFC) containing glucose as carbon source. By using modern techniques, OFFGEL fractionator and LTQ-Orbitrap for proteome and SBSE-TD-GC-MS for metabolite analysis, we quantified 84 proteins including 33 directly involved in the metabolism of glycerol, ethanol and 17 aroma compounds. Contents in acetaldehyde, acetic acid, decanoic acid, 1,1-diethoxyethane, benzaldehyde and 2-phenethyl acetate, changed above their odor thresholds under BFC, and those of decanoic acid, ethyl octanoate, ethyl decanoate and isoamyl acetate under NBFC. Of the twenty proteins involved in the metabolism of ethanol, acetaldehyde, acetoin, 2,3-butanediol, 1,1-diethoxyethane, benzaldehyde, organic acids and ethyl esters, only Adh2p, Ald4p, Cys4p, Fas3p, Met2p and Plb1p were detected under BFC and as many Acs2p, Ald3p, Cem1p, Ilv2p, Ilv6p and Pox1p, only under NBFC. Of the eight proteins involved in glycerol metabolism, Gut2p was detected only under BFC while Pgs1p and Rhr2p were under NBFC. Finally, of the five proteins involved in the metabolism of higher alcohols, Thi3p was present under BFC, and Aro8p and Bat2p were under NBFC. Copyright © 2015 Elsevier Ltd. All rights reserved.

pH-dependent stability of creatine ethyl ester: relevance to oral absorption.

PubMed

Gufford, Brandon T; Ezell, Edward L; Robinson, Dennis H; Miller, Donald W; Miller, Nicholas J; Gu, Xiaochen; Vennerstrom, Jonathan L

2013-09-01

Creatine ethyl ester hydrochloride (CEE) was synthesized as a prodrug of creatine (CRT) to improve aqueous solubility, gastrointestinal permeability, and ultimately the pharmacodynamics of CRT. We used high-performance liquid chromatography (HPLC) and proton nuclear magnetic resonance (NMR) to characterize the pH-dependent stability of CEE in aqueous solution and compared the permeability of CEE to CRT and creatinine (CRN) across Caco-2 human epithelial cell monolayers and transdermal permeability across porcine skin. CEE was most stable in a strongly acidic condition (half-life = 570 hours at pH 1.0) where it undergoes ester hydrolysis to CRT and ethanol. At pH ≥ 1.0, CEE cyclizes to CRN with the logarithm of the first order rate constant increasing linearly with pH. Above pH 8.0 (half-life = 23 sec) the rate of degradation was too rapid to be determined. The rate of degradation of CEE in cell culture media and simulated intestinal fluid (SIF) was a function of pH and correlated well with the stability in aqueous buffered solutions. The permeability of CEE across Caco-2 monolayers and porcine skin was significantly greater than that of CRT or CRN. The stability of CEE in acidic media together with its improved permeability suggests that CEE has potential for improved oral absorption compared to CRT.

Identification of triterpene hydroxycinnamates with in vitro antitumor activity from whole cranberry fruit (Vaccinium macrocarpon).

PubMed

Murphy, Brian T; MacKinnon, Shawna L; Yan, Xiaojun; Hammond, Gerald B; Vaisberg, Abraham J; Neto, Catherine C

2003-06-04

Bioactivity-guided fractionation of cranberry fruit was used to determine the identity of triterpenoid esters from Vaccinium macrocarpon, which inhibit tumor cell growth and may play a role in cancer prevention. In our previous study, a fraction from whole fruit exhibited tumor cell growth inhibition in vitro. The major components of this fraction were isolated by chromatographic separation of ethyl acetate extracts, purified by semipreparative HPLC, and identified by NMR as cis- (1) and trans- (2) isomers of 3-O-p-hydroxycinnamoyl ursolic acid. These triterpenoid esters have not been previously reported in Vaccinium fruit. Bioassay of the purified triterpene cinnamates in tumor cell lines in vitro showed slightly greater activity of compound 1 in most cell lines, with GI(50) values of approximately 20 microM in MCF-7 breast, ME180 cervical and PC3 prostate tumor cell lines. Quercetin was slightly less active than 1, while cyanidin-3-galactoside exhibited much lower cytotoxicity, with GI(50) greater than 250 microM in all cell lines. Phenylboronic acid (3) was also isolated from the fruit but showed insignificant antitumor activity.

Production of Structured Triacylglycerols Containing Palmitic Acids at sn-2 Position and Docosahexaenoic Acids at sn-1, 3 Positions.

PubMed

Liu, Yanjun; Guo, Yongli; Sun, Zhaomin; Jie, Xu; Li, Zhaojie; Wang, Jingfeng; Wang, Yuming; Xue, Changhu

2015-01-01

Docosahexaenoic acid supplementation has been shown well-established health benefits that justify their use as functional ingredients in healthy foods and nutraceutical products. Structured triacylglycerols rich in 1,3-docosahexenoyl-2-palmitoyl-sn-glycerol were produced from algal oil (Schizochytrium sp) which was prepared by a two-step process. Novozym 435 lipase was used to produce tripalmitin. Tripalmitin was then used to produce the final structured triacylglycerol (STAG) through interesterification reactions using Lipozyme RM IM. The optimum conditions for the enzymatic reaction were a mole ratio of tripalmitin/fatty acid ethyl esters 1:9, 60°C, 10% enzyme load (wt % of substrates), 10 h; the enzymatic product contained 51.6% palmitic acid (PA), 30.13% docosahexaenoic acid (DHA, C22:6 n-3) and 5.33% docosapentanoic acid (DPA, C22:5 n-3), 12.15% oleic acid (OLA). This STAG can be used as a functional ingredient in dietary supplementation to provide the benefits of DHA.

Effect of the omega-3 fatty acid plus vitamin E supplementation on subjective global assessment score, glucose metabolism, and lipid concentrations in chronic hemodialysis patients.

PubMed

Asemi, Zatollah; Soleimani, Alireza; Bahmani, Fereshteh; Shakeri, Hossein; Mazroii, Navid; Abedi, Fatemeh; Fallah, Melika; Mohammadi, Ali Akbar; Esmaillzadeh, Ahmad

2016-02-01

This study was conducted to determine the effects of omega-3 fatty acid plus vitamin E supplementation on subjective global assessment (SGA) score and metabolic profiles in chronic hemodialysis (HD) patients. This randomized double-blind placebo-controlled clinical trial was conducted among 120 chronic HD patients. Participants were randomly divided into four groups to receive: (i) 1250 mg/day omega-3 fatty acid containing 600 mg eicosapentaenoic acid and 300 mg docosahexaenoic acid + vitamin E placebo (n = 30), (ii) 400 IU/day vitamin E + omega-3 fatty acids placebo (n = 30), (iii) 1250 mg omega-3 fatty acids/day + 400 IU/day vitamin E (n = 30), and (iv) omega-3 fatty acids placebo + vitamin E placebo (n = 30) for 12 wk. Fasting blood samples were taken at baseline and after 12-wk intervention to measure metabolic profiles. Patients who received combined omega-3 fatty acids and vitamin E supplements compared with vitamin E, omega-3 fatty acids, and placebo had significantly decreased SGA score (p < 0.001), fasting plasma glucose (p = 0.01), serum insulin levels (p = 0.001), homeostasis model of assessment insulin resistance (p = 0.002), and improved quantitative insulin sensitivity check index (p = 0.006). Omega-3 fatty acids plus vitamin E supplementation for 12 wk among HD patients had beneficial effects on SGA score and metabolic profiles. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Fluoxetine potentiation of omega-3 fatty acid antidepressant effect: evaluating pharmacokinetic and brain fatty acid-related aspects in rodents.

PubMed

Laino, Carlos Horacio; Garcia, Pilar; Podestá, María Fernanda; Höcht, Christian; Slobodianik, Nora; Reinés, Analía

2014-10-01

We previously reported that combined fluoxetine administration at antidepressant doses renders additive antidepressant effects, whereas non-antidepressant doses potentiate the omega-3 fatty acid antidepressant effect. In the present study, we aimed to evaluate putative pharmacokinetic and brain omega-3 fatty acid-related aspects for fluoxetine potentiation of omega-3 fatty acid antidepressant effect in rats. Coadministration of omega-3 fatty acids with a non-antidepressant dose of fluoxetine (1 mg/kg day) failed to affect both brain fluoxetine concentration and norfluoxetine plasma concentration profile. Fluoxetine plasma concentrations remained below the sensitivity limit of the detection method. Either antidepressant (10 mg/kg day) or non-antidepressant (1 mg/kg day) doses of fluoxetine in combination with omega-3 fatty acids increased hippocampal docosapentaenoic acid (DPA, 22:5 omega-3) levels. Although individual treatments had no effects on DPA concentration, DPA increase was higher when omega-3 were combined with the non-antidepressant dose of fluoxetine. Chronic DPA administration exerted antidepressant-like effects in the forced swimming test while increasing hippocampal docosahexaenoic (22:6 omega-3) and DPA levels. Our results suggest no pharmacokinetic interaction and reveal specific hippocampal DPA changes after fluoxetine and omega-3 combined treatments in our experimental conditions. The DPA role in the synergistic effect of fluoxetine and omega-3 combined treatments will be for sure the focus of future studies. © 2014 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 103:3316-3325, 2014. © 2014 Wiley Periodicals, Inc. and the American Pharmacists Association.

Development of food-grade nanoemulsions and emulsions for delivery of omega-3 fatty acids: opportunities and obstacles in the food industry.

PubMed

Walker, Rebecca; Decker, Eric A; McClements, David Julian

2015-01-01

Consumption of biologically active amounts of omega-3 fatty acids is linked to improved human health, which has partly been attributed to their important role in brain development and cardiovascular health. Western diets are relatively low in omega-3 fatty acids and many consumers turn to supplements or functional foods to increase their intake of these healthy lipids. Fish oil is one of the most widely used sources of omega-3 fatty acid for supplementation and has greater health benefits than plant sources because of its higher concentration of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). The incorporation of omega-3 fatty acids into foods and beverages is often challenging due to their low water-solubility, poor oxidative stability, and variable bioavailability. Nanoemulsions offer a promising way to incorporate omega-3 fatty acids into liquid food systems like beverages, dressing, sauces, and dips. Nanoemulsions are colloidal dispersions that contain small oil droplets (r<100 nm) that may be able to overcome many of the challenges of fortifying foods and beverages with omega-3 fatty acids. The composition and fabrication of nanoemulsions can be optimized to increase the chemical and physical stability of oil droplets, as well as to increase the bioavailability of omega-3 fatty acids.

Omega-3 polyunsaturated fatty acids for cardiovascular diseases: present, past and future.

PubMed

Watanabe, Yasuhiro; Tatsuno, Ichiro

2017-08-01

Large-scale epidemiological studies on Greenlandic, Canadian and Alaskan Eskimos have examined the health benefits of omega-3 fatty acids consumed as part of the diet, and found statistically significant relative reduction in cardiovascular risk in people consuming omega-3 fatty acids. Areas covered: This article reviews studies on omega-3 fatty acids during the last 50 years, and identifies issues relevant to future studies on cardiovascular (CV) risk. Expert commentary: Although a meta-analysis of large-scale prospective cohort studies and randomized studies reported that fish and fish oil consumption reduced coronary heart disease-related mortality and sudden cardiac death, omega-3 fatty acids have not yet been shown to be effective in secondary prevention trials on patients with multiple cardiovascular disease (CVD) risk factors. The ongoing long-term CV interventional outcome studies investigate high-dose, prescription-strength omega-3 fatty acids. The results are expected to clarify the potential role of omega-3 fatty acids in reducing CV risk. The anti-inflammatory properties of omega-3 fatty acids are also important. Future clinical trials should also focus on the role of these anti-inflammatory mediators in human arteriosclerotic diseases as well as inflammatory diseases.

Renal-protective and ameliorating impacts of omega-3 fatty acids against aspartame damaged MDCK cells.

PubMed

Pandurangan, Muthuraman; Enkhtaivan, Gansukh; Veerappan, Muthuviveganandavel; Mistry, Bhupendra; Patel, Rahul; Moon, So Hyun; Nagajyothi, Patnamsetty Chidanandha; Kim, Doo Hwan

2017-11-01

Aspartame is widely used artificial sweeteners as food additives. Several researchers have pointed that the controversial report on the use of aspartame over more than decades. Omega-3 fatty acids are essential and unsaturated fatty acids, and it plays a remarkable role in vision, intelligence, neural development, and metabolism of neurotransmitters. Therefore, the present study was aimed to investigate the effect of omega-3 fatty acids on aspartame treated renal cells. Experimental groups were divided into three such as sham control, aspartame treated, and aspartame with omega-3 fatty acids. Cell viability was determined by sulforhodamine-b assay and flow cytometric analysis. The experimental results showed that the aspartame induced altered cell viability were reduced following treatment of aspartame with omega-3 fatty acids. Altered cell morphology was recovered by omega-3 fatty acids. DNA damage appeared in the highest concentration of aspartame used in this study. DNA damage characteristics such as comet tail and tiny head sections did not appear in the omega-3 fatty acids treated cells. Several microvilli and vesicular structures were found in aspartame treated cells. Altered morphology such as rounding, microvilli, and formation of dome-like structures did not appear in the omega-3 fatty acids with aspartame treated cells. Caspase-3 mRNA and protein expression were increased in aspartame treated cells, and these levels were reduced following omega-3 fatty acids treatment. Taking all these data together, it is suggested that the omega-3 fatty acids may be a therapeutic agent to reduce the aspartame induced biochemical and morphological alterations in normal renal cells. © 2017 BioFactors, 43(6):847-857, 2017. © 2017 International Union of Biochemistry and Molecular Biology.

Blood docosahexaenoic acid and eicosapentaenoic acid in vegans: Associations with age and gender and effects of an algal-derived omega-3 fatty acid supplement.

PubMed

Sarter, Barbara; Kelsey, Kristine S; Schwartz, Todd A; Harris, William S

2015-04-01

Several studies have demonstrated that vegetarians and vegans have much lower plasma concentrations of omega-3 fatty acids (i.e., docosahexaenoic and eicosapentaenoic acids) when compared to those who eat fish. The purposes of this study were 1) to define the age and/or sex-specific docosahexaenoic plus eicosapentaenoic acids levels in red blood cell membranes (expressed as a percent of total fatty acids; hereafter the omega-3 index) in long-term vegans, and 2) to determine the effects of a vegetarian omega-3 supplement (254 mg docosahexaenoic plus eicosapentaenoic acids/day for 4 months) on the omega-3 index. A sample (n = 165) of vegans was recruited, and their omega-3 index was determined using a dried blood spot methodology. A subset of 46 subjects with a baseline omega-3 index of <4% was given a vegetarian omega-3 supplement for 4 months and then retested. The mean ± SD omega-3 index was 3.7 ± 1.0% which was similar to that of a cohort of omnivores (deployed US soldiers) from a recently-reported study. Among the vegan cohort, the index was significantly higher in females than males (3.9 ± 1.0% vs. 3.5 ± 1.0%; p = 0.026) and was directly related to age (p for trend = 0.009). The omega-3 index increased from 3.1 ± 0.6% to 4.8 ± 0.8% (p = 0.009) in the supplementation study. We conclude that vegans have low baseline omega-3 levels, but not lower than omnivores who also consume very little docosahexaenoic and eicosapentaenoic acids. The vegans responded robustly to a relatively low dose of a vegetarian omega-3 supplement. Copyright © 2014 The Authors. Published by Elsevier Ltd.. All rights reserved.

Microalgal biofactories: a promising approach towards sustainable omega-3 fatty acid production

PubMed Central

2012-01-01

Omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) provide significant health benefits and this has led to an increased consumption as dietary supplements. Omega-3 fatty acids EPA and DHA are found in animals, transgenic plants, fungi and many microorganisms but are typically extracted from fatty fish, putting additional pressures on global fish stocks. As primary producers, many marine microalgae are rich in EPA (C20:5) and DHA (C22:6) and present a promising source of omega-3 fatty acids. Several heterotrophic microalgae have been used as biofactories for omega-3 fatty acids commercially, but a strong interest in autotrophic microalgae has emerged in recent years as microalgae are being developed as biofuel crops. This paper provides an overview of microalgal biotechnology and production platforms for the development of omega-3 fatty acids EPA and DHA. It refers to implications in current biotechnological uses of microalgae as aquaculture feed and future biofuel crops and explores potential applications of metabolic engineering and selective breeding to accumulate large amounts of omega-3 fatty acids in autotrophic microalgae. PMID:22830315

A general strategy for stereoselective glycosylations.

PubMed

Kim, Jin-Hwan; Yang, Hai; Park, Jin; Boons, Geert-Jan

2005-08-31

The principal challenge that the synthesis of oligosaccharides of biological importance presents is the development of a general approach for the stereoselective introduction of a glycosidic linkage. It is shown here that a (1S)-phenyl-2-(phenylsulfanyl)ethyl moiety at C-2 of a glycosyl donor can perform neighboring group participation to give a quasi-stable anomeric sulfonium ion. Due to steric and electronic factors, the sulfonium ion is formed as a trans-decalin ring system. Displacement of the sulfonium ion by a hydroxyl leads to the stereoselective formation of alpha-glycosides. NMR experiments were employed to show convincingly the presence of the beta-linked sulfonium ion intermediate. The (1S)-phenyl-2-(phenylsulfanyl)ethyl moiety could be introduced by reaction of a sugar alcohol with acetic acid (1S)-phenyl-2-(phenylsulfanyl)ethyl ester in the presence of BF(3)-OEt(2). Furthermore, it could be removed by conversion into acetate by treatment with BF(3)-OEt(2) in acetic anhydride. The introduction as well as the cleavage reaction proceeds through the formation of an intermediate episulfonium ion. The use of the new methodology in combination with traditional neighboring group participation by esters to introduce beta-glycosides makes it possible, for the first time, to synthesize a wide variety of oligosaccharides by routine procedures. The latter was demonstrated by the synthesis of the Galili trisaccharide, which has been identified as an epitope that can trigger acute rejections in xeno-transplantations, by the one-pot two-step glycosylation sequence.

Characterisation of aroma profiles of commercial soy sauce by odour activity value and omission test.

PubMed

Feng, Yunzi; Su, Guowan; Zhao, Haifeng; Cai, Yu; Cui, Chun; Sun-Waterhouse, Dongxiao; Zhao, Mouming

2015-01-15

Twenty-seven commercial soy sauces produced through three different fermentation processes (high-salt liquid-state fermentation soy sauce, HLFSS; low-salt solid-state fermentation soy sauce, LSFSS; Koikuchi soy sauce, KSS) were examined to identify the aroma compounds and the effect of fermentation process on the flavour of the soy sauce was investigated. Results showed that 129 volatiles were identified, of which 41 aroma-active components were quantified. The types of odorants occurring in the three soy sauce groups were similar, although their intensities significantly differed. Many esters and phenols were found at relatively high intensities in KSS, whereas some volatile acids only occurred in LSFSS. Furthermore, 23 aroma compounds had average OAVs>1, among which 3-methylbutanal, ethyl acetate, 4-hydroxy-2-ethyl-5-methyl-3(2H)-furanone, 2-methylbutanal and 3-(methylthio)propanal exhibited the highest average OAVs (>100). In addition, omission tests verified the important contribution of the products resulting from amino acid catabolism to the characteristic aroma of soy sauce. Copyright © 2014. Published by Elsevier Ltd.

Antioxidant and quinone reductase-inducing constituents of black chokeberry (Aronia melanocarpa) fruits.

PubMed

Li, Jie; Deng, Ye; Yuan, Chunhua; Pan, Li; Chai, Heebyung; Keller, William J; Kinghorn, A Douglas

2012-11-21

Using in vitro hydroxyl radical-scavenging and quinone reductase-inducing assays, bioactivity-guided fractionation of an ethyl acetate-soluble extract of the fruits of the botanical dietary supplement, black chokeberry (Aronia melanocarpa), led to the isolation of 27 compounds, including a new depside, ethyl 2-[(3,4-dihydroxybenzoyloxy)-4,6-dihydroxyphenyl] acetate (1), along with 26 known compounds (2-27). The structures of the isolated compounds were identified by analysis of their physical and spectroscopic data ([α](D), NMR, IR, UV, and MS). Altogether, 17 compounds (1-4, 9, 15-17, and 19-27) showed significant antioxidant activity in the hydroxyl radical-scavenging assay, with hyperin (24, ED(50) = 0.17 μM) being the most potent. The new compound (1, ED(50) = 0.44 μM) also exhibited potent antioxidant activity in this assay. Three constituents of black chokeberry fruits doubled quinone reductase activity at concentrations <20 μM, namely, protocatechuic acid [9, concentration required to double quinone reductase activity (CD) = 4.3 μM], neochlorogenic acid methyl ester (22, CD = 6.7 μM), and quercetin (23, CD = 3.1 μM).

Therapeutic Effects of Omega-3 Fatty Acids on Chronic Kidney Disease-Associated Pruritus: a Literature Review

PubMed Central

Panahi, Yunes; Dashti-Khavidaki, Simin; Farnood, Farahnoosh; Noshad, Hamid; Lotfi, Mahsa; Gharekhani, Afshin

2016-01-01

Uremic pruritus remains one of the most tormenting, frequent and potentially disabling problem in chronic kidney disease (CKD) patients. However, an area of substantial etiological interest with relation to uremic pruritus is the essential fatty acids deficiency. So we performed a literature review to elucidate the efficacy of omega-3 fatty acids on uremic pruritus. This review evaluated all of the studies published in English language, focusing on the clinical effects of omega-3 fatty acids on uremic pruritus. The literature review was conducted in December 2015 and carried out by searching Scopus, Medline, Cochrane central register of controlled trials, and Cochrane database of systematic reviews. The search terms were "kidney injury", "kidney failure", "chronic kidney disease", "end-stage renal disease", "dialysis", "hemodialysis", "peritoneal dialysis", "pruritus", "itch", "skin problems", "fish oil", "omega 3", "n-3 fatty acids", "polyunsaturated fatty acids", "docosahexaenoic acid", and "eicosapentaenoic acid". Four small studies investigating potential benefits of omega-3 fatty acids on symptoms of uremic pruritus were found. Among them, three small randomized controlled trials have shown a significant improvement in pruritus symptoms (evaluated by a standard questionnaire) in CKD patients who took omega-3 supplement compared to omega-6, omega-9, and placebo supplementation. Despite numerous limitations of the studies, it is worth noting that even minor reduction in itching symptoms may be clinically significant for CKD patients. Therefore, and considering multiple health benefits of omega-3 fatty acids in advanced CKD and negligible risk profile, omega-3 intake can wisely be applied to CKD patients with uremic pruritus. PMID:28101457

Evaluation of certain food additives.

PubMed

2009-01-01

This report represents the conclusions of a Joint FAO/WHO Expert Committee convened to evaluate the safety of various food additives, including flavouring agents, with a view to recommending acceptable daily intakes (ADIs) and to preparing specifications for identity and purity. The first part of the report contains a general discussion of the principles governing the toxicological evaluation and assessment of intake of food additives (in particular, flavouring agents). A summary follows of the Committee's evaluations of technical, toxicological and intake data for certain food additives (asparaginase from Aspergillus niger expressed in A. niger, calcium lignosulfonate (40-65), ethyl lauroyl arginate, paprika extract, phospholipase C expressed in Pichia pastoris, phytosterols, phytostanols and their esters, polydimethylsiloxane, steviol glycosides and sulfites [assessment of dietary exposure]) and 10 groups of related flavouring agents (aliphatic branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters; aliphatic linear alpha,beta-unsaturated aldehydes, acids and related alcohols, acetals and esters; aliphatic secondary alcohols, ketones and related esters; alkoxy-substituted allylbenzenes present in foods and essential oils and used as flavouring agents; esters of aliphatic acyclic primary alcohols with aliphatic linear saturated carboxylic acids; furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers; miscellaneous nitrogen-containing substances; monocyclic and bicyclic secondary alcohols, ketones and related esters; hydroxy- and alkoxy-substituted benzyl derivatives; and substances structurally related to menthol). Specifications for the following food additives were revised: canthaxanthin; carob bean gum and carob bean gum (clarified); chlorophyllin copper complexes, sodium and potassium salts; Fast Green FCF; guar gum and guar gum (clarified); iron oxides; isomalt; monomagnesium phosphate; Patent Blue V; Sunset Yellow FCF; and trisodium diphosphate. Re-evaluation of flavouring agents for which estimated intake was based on anticipated poundage data was carried out for 2-isopropyl- N,2,3-trimethylbutyramide (No. 1595) and L-monomenthyl glutarate (No. 1414). Annexed to the report are tables summarizing the Committee's recommendations for intakes and toxicological evaluations of the food additives considered.

Glycidyl fatty acid esters in food by LC-MS/MS: method development.

PubMed

Becalski, A; Feng, S Y; Lau, B P-Y; Zhao, T

2012-07-01

An improved method based on liquid chromatography-tandem mass spectrometry (LC-MS/MS) for the analysis of glycidyl fatty acid esters in oils was developed. The method incorporates stable isotope dilution analysis (SIDA) for quantifying the five target analytes: glycidyl esters of palmitic (C16:0), stearic (C18:0), oleic (C18:1), linoleic (C18:2) and linolenic acid (C18:3). For the analysis, 10 mg sample of edible oil or fat is dissolved in acetone, spiked with deuterium labelled analogs of glycidyl esters and purified by a two-step chromatography on C18 and normal silica solid phase extraction (SPE) cartridges using methanol and 5% ethyl acetate in hexane, respectively. If the concentration of analytes is expected to be below 0.5 mg/kg, 0.5 g sample of oil is pre-concentrated first using a silica column. The dried final extract is re-dissolved in 250 μL of a mixture of methanol/isopropanol (1:1, v/v), 15 μL is injected on the analytical C18 LC column and analytes are eluted with 100% methanol. Detection of target glycidyl fatty acid esters is accomplished by LC-MS/MS using positive ion atmospheric pressure chemical ionization operating in Multiple Reaction Monitoring mode monitoring 2 ion transitions for each analyte. The method was tested on replicates of a virgin olive oil which was free of glycidyl esters. The method detection limit was calculated to be in the range of 70-150 μg/kg for each analyte using 10 mg sample and 1-3 μg/kg using 0.5 g sample of oil. Average recoveries of 5 glycidyl esters spiked at 10, 1 and 0.1 mg/kg were in the range 84% to 108%. The major advantage of our method is use of SIDA for all analytes using commercially available internal standards and detection limits that are lower by a factor of 5-10 from published methods when 0.5 g sample of oil is used. Additionally, MS/MS mass chromatograms offer greater specificity than liquid chromatography-mass spectrometry operated in selected ion monitoring mode. The method will be applied to the survey of glycidyl fatty acid esters in food products on the Canadian market.

High levels of omega-3 fatty acids in milk from omega-3 fatty acid-supplemented mothers are related to less immunoglobulin E-associated disease in infancy.

PubMed

Warstedt, Kristina; Furuhjelm, Catrin; Fälth-Magnusson, Karin; Fagerås, Malin; Duchén, Karel

2016-11-01

We previously reported a protective effect of maternal omega-3 fatty acid supplements on the development of immunoglobulin E (IgE)-associated disease in infancy. This study assessed omega-3 long-chain polyunsaturated fatty acids (LCPUFA) in maternal milk in relation to omega-3 LCPUFA supplementation and the development of allergic disease in their infants. This study randomised 95 pregnant women at risk of having an allergic infant, to daily supplements of 2.6 g omega-3 LCPUFA or a placebo of 2.7 g soya bean oil from gestational week 25 until 3 months of lactation. Breast milk samples were collected as colostrum, at one and 3 months. Milk fatty acids were related to allergic outcome in the infants at 24 months. Omega-3 milk fatty acids were higher in women who received omega-3 supplements than the placebo group (p < 0.01). Higher proportions of milk eicosapentaenoic acid and docosahexaenoic acid and a lower arachidonic/eicosapentaenoic acid ratio were associated with an absence of IgE-associated disease in the infants. None of the children developed IgE-associated atopic eczema above a level of 0.83 mol% eicosapentaenoic acid in colostrum. [Correction added on 7 July 2016, after online publication: In the preceding sentence, the correct word should be "above" instead of "below" and this has been amended in this current version.] CONCLUSION: High omega-3 LCPUFA milk levels in mothers who received omega-3 LCPUFA supplements were related to fewer allergies in their children. ©2016 Foundation Acta Paediatrica. Published by John Wiley & Sons Ltd.

Omega-3 Polyunsaturated Fatty Acids and Their Health Benefits.

PubMed

Shahidi, Fereidoon; Ambigaipalan, Priyatharini

2018-03-25

Omega-3 polyunsaturated fatty acids (PUFAs) include α-linolenic acid (ALA; 18:3 ω-3), stearidonic acid (SDA; 18:4 ω-3), eicosapentaenoic acid (EPA; 20:5 ω-3), docosapentaenoic acid (DPA; 22:5 ω-3), and docosahexaenoic acid (DHA; 22:6 ω-3). In the past few decades, many epidemiological studies have been conducted on the myriad health benefits of omega-3 PUFAs. In this review, we summarized the structural features, properties, dietary sources, metabolism, and bioavailability of omega-3 PUFAs and their effects on cardiovascular disease, diabetes, cancer, Alzheimer's disease, dementia, depression, visual and neurological development, and maternal and child health. Even though many health benefits of omega-3 PUFAs have been reported in the literature, there are also some controversies about their efficacy and certain benefits to human health.

Omega 3 but not omega 6 fatty acids inhibit AP-1 activity and cell transformation in JB6 cells.

PubMed

Liu, G; Bibus, D M; Bode, A M; Ma, W Y; Holman, R T; Dong, Z

2001-06-19

Epidemiological and animal-based investigations have indicated that the development of skin cancer is in part associated with poor dietary practices. Lipid content and subsequently the derived fatty acid composition of the diet are believed to play a major role in the development of tumorigenesis. Omega 3 (omega3) fatty acids, including docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA), can effectively reduce the risk of skin cancer whereas omega 6 (omega6) fatty acids such as arachidonic acid (AA) reportedly promote risk. To investigate the effects of fatty acids on tumorigenesis, we performed experiments to examine the effects of the omega3 fatty acids EPA and DHA and of the omega6 fatty acid AA on phorbol 12-tetradecanoate 13-acetate (TPA)-induced or epidermal growth factor (EGF)-induced transcription activator protein 1 (AP-1) transactivation and on the subsequent cellular transformation in a mouse epidermal JB6 cell model. DHA treatment resulted in marked inhibition of TPA- and EGF-induced cell transformation by inhibiting AP-1 transactivation. EPA treatment also inhibited TPA-induced AP-1 transactivation and cell transformation but had no effect on EGF-induced transformation. AA treatment had no effect on either TPA- or EGF-induced AP-1 transactivation or transformation, but did abrogate the inhibitory effects of DHA on TPA- or EGF-induced AP-1 transactivation and cell transformation in a dose-dependent manner. The results of this study demonstrate that the inhibitory effects of omega3 fatty acids on tumorigenesis are more significant for DHA than for EPA and are related to an inhibition of AP-1. Similarly, because AA abrogates the beneficial effects of DHA, the dietary ratio of omega6 to omega3 fatty acids may be a significant factor in mediating tumor development.

Ferulic acid ethyl ester diminished Complete Freund's Adjuvant-induced incapacitation through antioxidant and anti-inflammatory activity.

PubMed

Cunha, Francisco Valmor Macedo; Gomes, Bruno de Sousa; Neto, Benedito de Sousa; Ferreira, Alana Rodrigues; de Sousa, Damião Pergentino; de Carvalho e Martins, Maria do Carmo; Oliveira, Francisco de Assis

2016-01-01

Ferulic acid ethyl ester (FAEE) is a derivate from ferulic acid which reportedly has antioxidant effect; however, its role on inflammation was unknown. In this study, we investigated the orally administered FAEE anti-inflammatory activity on experimental inflammation models and Complete Freund's Adjuvant (CFA)-induced arthritis in rats. CFA-induced arthritis has been evaluated by incapacitation model and radiographic knee joint records at different observation time. FAEE (po) reduced carrageenan-induced paw edema (p < 0.001) within the 1st to 5th hours at 50 and 100 mg/kg doses. FAEE 50 and 100 mg/kg, po inhibited leukocyte migration into air pouch model (p < 0.001), and myeloperoxidase, superoxide dismutase, and catalase activities (p < 0.001) increased total thiol concentration and decreased the TNF-α and IL-1β concentrations, NO, and thiobarbituric acid reactive species. In the CFA-induced arthritis, FAEE 50 and 100 mg/kg significantly reduced the edema and the elevation paw time, a joint disability parameter, since second hour after arthritis induction (p < 0.001). FAEE presented rat joint protective activity in radiographic records (p < 0.001). The data suggest that the FAEE exerts anti-inflammatory activity by inhibiting leukocyte migration, oxidative stress reduction, and pro-inflammatory cytokines.

Omega-3 fatty acids have antidepressant activity in forced swimming test in Wistar rats.

PubMed

Lakhwani, Lalit; Tongia, Sudheer K; Pal, Veerendra S; Agrawal, Rajendra P; Nyati, Prem; Phadnis, Pradeep

2007-01-01

Forced swimming test is used to induce a characteristic behavior of immobility in rats, which resembles depression in humans to some extent. We evaluated the effect of omega-3 fatty acids alone as well as compared it with the standard antidepressant therapy with fluoxetine in both acute and chronic studies. In both the studies, rats were divided into 4 groups and subjected to the following drug interventions - Group 1- control: Group 2- fluoxetine in dose of 10 mg/kg subcutaneously 23.5, 5 and 1 h before the test: Group 3- omega-3 fatty acids in dose of 500 mg/kg orally; Group 4- fluoxetine plus omega-3 fatty acids both. In acute study, omega-3 fatty acids were given in single dose 2 h prior to the test while in chronic study omega-3 fatty acids were given daily for a period of 28 days. All animals were subjected to a 15-min pretest followed 24 h later by a 5-min test. A time sampling method was used to score the behavioral activity in each group. The results revealed that in acute study, omega-3 fatty acids do not have any significant effect in forced swimming test. However, in chronic study, omega-3 fatty acids affect the immobility and swimming behavior significantly when compared with control (p < 0.01) without any significant effect on climbing behavior and the efficacy of combination of omega-3 fatty acids and fluoxetine is significantly more than that of fluoxetine alone in changing the behavioral activity of rats in forced swimming test. It leads to the conclusion that omega-3 fatty acids have antidepressant activity per se, and the combination of fluoxetine and omega-3 fatty acids has more antidepressant efficacy than fluoxetine alone in forced swimming test in Wistar rats.

Omega-3 fatty acids: new insights into the pharmacology and biology of docosahexaenoic acid, docosapentaenoic acid, and eicosapentaenoic acid.

PubMed

Davidson, Michael H

2013-12-01

Fish oil contains a complex mixture of omega-3 fatty acids, which are predominantly eicosapentaenoic acid (EPA), docosapentaenoic acid, and docosahexaenoic acid (DHA). Each of these omega-3 fatty acids has distinct biological effects that may have variable clinical effects. In addition, plasma levels of omega-3 fatty acids are affected not only by dietary intake, but also by the polymorphisms of coding genes fatty acid desaturase 1-3 for the desaturase enzymes that convert short-chain polyunsaturated fatty acids to long-chain polyunsaturated fatty acids. The clinical significance of this new understanding regarding the complexity of omega-3 fatty acid biology is the purpose of this review. FADS polymorphisms that result in either lower levels of long-chain omega-3 fatty acids or higher levels of long-chain omega-6 polyunsaturated fatty acids, such as arachidonic acid, are associated with dyslipidemia and other cardiovascular risk factors. EPA and DHA have differences in their effects on lipoprotein metabolism, in which EPA, with a more potent peroxisome proliferator-activated receptor-alpha effect, decreases hepatic lipogenesis, whereas DHA not only enhances VLDL lipolysis, resulting in greater conversion to LDL, but also increases HDL cholesterol and larger, more buoyant LDL particles. Overall, these results emphasize that blood concentrations of individual long-chain polyunsaturated fatty acids, which reflect both dietary intake and metabolic influences, may have independent, but also complementary- biological effects and reinforce the need to potentially provide a complex mixture of omega-3 fatty acids to maximize cardiovascular risk reduction.

Insight into the contribution of isoprostanoids to the health effects of omega 3 PUFAs.

PubMed

Joumard-Cubizolles, Laurie; Lee, Jetty Chung-Yung; Vigor, Claire; Leung, Ho Hang; Bertrand-Michel, Justine; Galano, Jean-Marie; Mazur, André; Durand, Thierry; Gladine, Cecile

2017-11-01

Omega 3 polyunsaturated fatty acids have been reported to confer beneficial health effects notably in the field of cardiovascular and inflammatory diseases. The current knowledge suggests a significant portion of the effects of omega 3 polyunsaturated fatty acids are mediated by their oxygenated metabolites. This review attempts to cover the current literature about the contribution of specific omega 3 oxygenated metabolites, namely omega 3 isoprostanoids, which are produced through free-radical mediated oxidation. A special emphasis has been given to the most biologically relevant omega 3 polyunsaturated fatty acids namely the α-linolenic, eicosapentaenoic and docosahexaenoic acids. The review includes a comprehensive description of the biosynthetic pathways, a summary of studies related to the biological significance of omega 3 isoprostanoids as well as a critical description of analytical development in the field of omega 3 isoprostanoids profiling in biological samples. Copyright © 2017 Elsevier Inc. All rights reserved.

Omega-3 fatty acids upregulate adult neurogenesis

PubMed Central

Beltz, Barbara S.; Tlusty, Michael F.; Benton, Jeannie L.; Sandeman, David C.

2007-01-01

Omega-3 fatty acids play crucial roles in the development and function of the central nervous system. These components, which must be obtained from dietary sources, have been implicated in a variety of neurodevelopmental and psychiatric disorders. Furthermore, the presence of omega-6 fatty acids may interfere with omega-3 fatty acid metabolism. The present study investigated whether changes in dietary ratios of omega-3:omega-6 fatty acids influence neurogenesis in the lobster (Homarus americanus) brain where, as in many vertebrate species, neurogenesis persists throughout life. The factors that regulate adult neurogenesis are highly conserved among species, and the crustacean brain has been successfully utilized as a model for investigating this process. In this study, lobsters were fed one of three diets that differed in fatty acid content. These animals were subsequently incubated in 5-bromo-2′-deoxyuridine (BrdU) to detect cells in S-phase of the cell cycle. A quantitative analysis of the resulting BrdU-labeled cells in the projection neuron cluster in the brain shows that short-term augmentation of dietary omega-3 relative to omega-6 fatty acids results in significant increases in the numbers of S-phase cells, and that the circadian pattern of neurogenesis is also altered. It is proposed that the ratio of omega-3:omega-6 fatty acids may alter neurogenesis via modulatory influences on membrane proteins, cytokines and/or neurotrophins. PMID:17240063

Role of Omega-3 Fatty Acids on Lipid Profile in Diabetic Dyslipidaemia: Single Blind, Randomised Clinical Trial.

PubMed

Chauhan, Shaylika; Kodali, Hanish; Noor, Jawad; Ramteke, Karuna; Gawai, Vidisha

2017-03-01

Diabetic dyslipidaemia is characterised by hypertriglyceridaemia, low High Density Lipoprotein (HDL), postprandial lipimea, small and dense LDL particles is considered to be a major predisposing factor for various macrovascular complications. Omega-3 fatty acids are fish oil derivative introduced in the market for dyslipidaemia associated with increased triglyceride level. To study the effect of omega-3 fatty acids on lipid profile in Type II diabetes patients. This study was prospective, single blind, randomized comparative trial. Hundred patients were randomized into three groups. Group I received metformin 500 mg twice daily and placebo, Group II received metformin 500 mg twice daily and omega-3 fatty acids (1 gram) once daily and the Group III received metformin 500 mg twice daily and omega-3 fatty acids (1 gram) twice daily. ANOVA test was applied for analysis. Group II was effective in reducing the triglyceride level from 144.59±14.18 mg/dl to 101±13.31 mg/dl which was significant as compared to Group I from 147.67±18.57 mg/dl to 145.8±19.86 mg/dl respectively. Group III containing 1 g of omega-3 fatty acids twice daily showed decrease from 144.83±22.17 mg/dl to 86±17.46 mg/dl and was more effective in reducing triglyceride levels than Group II containing 1 gram of omega-3 fatty acids once daily. Omega-3 fatty acids can be given in conjunction with metformin to reduce triglyceride levels in diabetic dyslipidaemia without any adverse drug reactions or any drug interaction. Omega-3 fatty acids were effective in reducing the triglyceride level significantly as compared to placebo. Two grams of omega-3 fatty acids were more effective than 1 gram of omega-3 fatty acids in reducing triglyceride levels.

Microwave spectroscopy and curious molecular dynamics of ethyl trifluoroacetate

NASA Astrophysics Data System (ADS)

Bohn, Robert K.; Montgomery, John A.; Harvey Michels, H.; Acharte, Christian

2017-05-01

The first ethyl ester whose structure was determined by microwave spectroscopy is ethyl formate. It exists in two conformations. In the 1970s, that study was used as a model to determine the structures of other ethyl esters, ethyl cyanoformate, chloroformate, and trifluoroacetate. They display the same conformations as ethyl formate. But under the experimental conditions used, Stark modulation with a maximum electric field, static low pressure gas, rapid sweeping, and long detector time constants, each of those esters displays bands of an additional third species. A careful, high resolution study of ethyl cyanoformate only observed two conformers. A model has been proposed that the third species derives from a dense array of torsionally excited states with broadened transitions due to short lifetimes. The present study of ethyl trifluoroacetate in a pulsed jet Fourier Transform spectrometer is intended to clarify the earlier results. Two conformers are observed including all their monosubstituted 13C and 18O isotopologs. In a pulsed jet Fourier Transform spectrometer using argon as the carrier gas, only one conformer is observed. Switching to helium as the carrier gas, another, higher energy conformer is also observed.

Mediating chemical reactions using polysaccharides

NASA Astrophysics Data System (ADS)

Tyler, Lauren E.

We have studied the NaBH4-mediated hydrogenation of select alkenes catalyzed by polysaccharide-stabilized nanoparticles. We compared the catalytic properties of Ni-based nanoparticles or Au/Co-based nanoparticles on the hydrogenation of cinnamic acid, cinnamide, cinnamyl alcohol, and ethyl cinnamate. We evaluated the possibility that the type of stabilizing polysaccharide surrounding the nanoparticle may affect the selectivity towards the alkene compounds that undergo the hydrogenation reaction. We found that the hydrogenation of cinnamide or ethyl cinnamate proceeded readily to 100% completion independent of the type of polysaccharide stabilizing the nanoparticle. However, the extent of the hydrogenation of cinnamyl alcohol and cinnamic acid varied greatly depending on the type of polysaccharide stabilizing the nanoparticle. In the course of these studies, we observed that some polysaccharides by themselves promoted the hydrolysis of ethyl cinnamate. Thus, we have raised the hypothesis that some polysaccharides may act as "esterases" and explored the interaction between select polysaccharides and a variety of ester compounds.

21 CFR 175.320 - Resinous and polymeric coatings for polyolefin films.

Code of Federal Regulations, 2014 CFR

2014-04-01

... film over one or both sides of a base film produced from one or more of the basic olefin polymers complying with § 177.1520 of this chapter. The base polyolefin film may contain optional adjuvant substances... Limitations (i) Resins and polymers: Acrylic acid polymer and its ethyl or methyl esters Acrylamide...

SOLVENT EXTRACTION PROCESS FOR PROTACTINIUM

DOEpatents

Hyde, E.K.; Katzin, L.I.; Wolf, M.J.

1961-04-01

A process is described for separating protactinium from thorium present together as the nitrates in a 0.1 to 10 N nitric acid solution. The separation is carried out by extraction with an aliphatic alcohol, ketone, and/or ester having at least six carbon atoms, such as n-amyl acetate, 2-ethyl hexanol, and diisopropyl ketone.

Omega-3 Fatty Acids

MedlinePlus

Omega-3 fatty acids are used together with lifestyle changes (diet, weight-loss, exercise) to reduce the amount ... the blood in people with very high triglycerides. Omega-3 fatty acids are in a class of medications ...

Intake of total omega-3 fatty acids, eicosapentaenoic acid and docosahexaenoic acid and risk of coronary heart disease in the Spanish EPIC cohort study.

PubMed

Amiano, P; Machón, M; Dorronsoro, M; Chirlaque, M Dolores; Barricarte, A; Sánchez, M-J; Navarro, C; Huerta, J M; Molina-Montes, E; Sánchez-Cantalejo, E; Urtizberea, M; Arriola, L; Larrañaga, N; Ardanaz, E; Quirós, J R; Moreno-Iribas, C; González, C A

2014-03-01

The evidence about the benefits of omega-3 fatty acid intake on coronary heart disease (CHD) is not consistent. We thus aimed to assess the relation between dietary intake of total omega-3 fatty acids (from plant and marine foods) and marine polyunsaturated fatty acids (PUFAs), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), on the risk of CHD in the Spanish cohort of the European Prospective Investigation into Cancer and Nutrition (EPIC). The analysis included 41,091 men and women aged 20-69 years, recruited from 1992 to 1996 and followed-up until December 2004. Omega-3 fatty acid intake was estimated from a validated dietary questionnaire. Only participants with definite incident CHD event were considered as cases. Cox regression models were used to assess the association between the intake of total omega-3 fatty acids, EPA or DHA and CHD. A total of 609 participants (79% men) had a definite CHD event. Mean intakes of total omega-3 fatty acids, EPA and DHA were very similar in the cases and in the cohort, both in men and women. In the multivariate adjusted model, omega-3 fatty acids, EPA and DHA were not related to incident CHD in either men or women. The hazard ratios (HR) for omega-3 were 1.23 in men (95% CI 0.94-15.9, p = 0.20); and 0.77 in women (95% CI 0.46-1.30, p = 0.76). In the Spanish EPIC cohort, with a relatively high intake of fish, no association was found between EPA, DHA and total omega-3 fatty acid intake and risk of CHD. Copyright © 2013 Elsevier B.V. All rights reserved.

Synthesis of α-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles.

PubMed

Vasconcelos, Stanley N S; Fornari, Evelin; Caracelli, Ignez; Stefani, Hélio A

2017-11-01

The Ugi multicomponent reaction has been used as an important synthetic route to obtain compounds with potential biological activity. We present the rapid and efficient synthesis of [Formula: see text]-amino-1,3-dicarbonyl compounds in moderate to good yields via Ugi flow chemistry reactions performed with a continuous flow reactor. Such [Formula: see text]-amino-1,3-dicarbonyl compounds can act as precursors for the production of [Formula: see text]-amino acids via hydrolysis of the ethyl ester group as well as building blocks for the synthesis of novel compounds with the 1,2,3-triazole ring. The [Formula: see text]-amino acid derivatives of the Ugi flow chemistry reaction products were then used for dipeptide synthesis.

Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease.

PubMed

Yanovsky, Inessa; Finkin-Groner, Efrat; Zaikin, Andrey; Lerman, Lena; Shalom, Hila; Zeeli, Shani; Weill, Tehilla; Ginsburg, Isaac; Nudelman, Abraham; Weinstock, Marta

2012-12-13

The cascade of events that occurs in Alzheimer's disease involving oxidative stress and the reduction in cholinergic transmission can be better addressed by multifunctional drugs than cholinesterase inhibitors alone. For this purpose, we prepared a large number of derivatives of indoline-3-propionic acids and esters. They showed scavenging activity against different radicals in solution and significant protection against cytotoxicity in cardiomyocytes and primary cultures of neuronal cells exposed to H2O2 species and serum deprivation at concentrations ranging from 1 nM to 10 μM depending on the compound. For most of the indoline-3-propionic acid derivatives, introduction of N-methyl-N-ethyl or N-methyl-N-(4-methoxyphenyl) carbamate moieties at positions 4, 6, or 7 conferred both acetyl (AChE) and butyryl (BuChE) cholinesterase inhibitory activities at similar concentrations to those that showed antioxidant activity. The most potent AChE inhibitors were 120 (3-(2-aminoethyl) indolin-4-yl ethyl(methyl)carbamate dihydrochloride) and 94 (3-(3-methoxy-3-oxopropyl)-4-(((4-methoxyphenyl)(methyl) carbamoyl)oxy)indolin-1-ium hydrochloride) with IC50s of 0.4 and 1.2 μM, respectively.

Effect of omega-3 fatty acids on canine atopic dermatitis.

PubMed

Mueller, R S; Fieseler, K V; Fettman, M J; Zabel, S; Rosychuk, R A W; Ogilvie, G K; Greenwalt, T L

2004-06-01

Twenty-nine dogs were included in a double-blinded, placebo-controlled, randomised trial and were orally supplemented for 10 weeks with either flax oil (200 mg/kg/day), eicosapentaenoic acid (50 mg/kg/day) and docosahexaenoic acid (35 mg/kg/day) in a commercial preparation, or mineral oil as a placebo. For each dog, clinical scores were determined based on a scoring system developed prior to the trial. Total omega-6 and omega-3 intake and the ratio of omega-6:omega-3 (omega-6:3) were calculated before and after the trial. The dogs' clinical scores improved in those supplemented with flax oil and the commercial preparation, but not in the placebo group. No correlation was identified between total fatty acid intake or omega-6:3 ratio and clinical scores. Based on the results of this study, the total intake of fatty acids or the omega-6:3 ratio do not seem to be the main factors in determining the clinical response.

Occurrence of fatty acid short-chain-alkyl esters in fruits of Celastraceae plants.

PubMed

Sidorov, Roman A; Zhukov, Anatoly V; Pchelkin, Vasily P; Vereshchagin, Andrei G; Tsydendambaev, Vladimir D

2013-06-01

Small amounts of a mixture of fatty acid short-chain-alkyl esters (FASCAEs) were obtained from the fruits of twelve plant species of Celastraceae family, and in five of them the FASCAEs were present not only in the arils but also in the seeds. These mixtures contained 32 individual FASCAE species, which formed four separate fractions, viz. FA methyl, ethyl, isopropyl, and butyl esters (FAMEs, FAEEs, FAIPEs, and FABEs, resp.). The FASCAE acyl components included the residues of 16 individual C₁₄-C₂₄ saturated, mono-, di-, and trienoic FAs. Linoleic, oleic, and palmitic acids, and, in some cases, also α-linolenic acid predominated in FAMEs and FAEEs, while myristic acid was predominant in FAIPEs. It can be suggested that, in the fruit arils of some plant species, FAMEs and FAEEs were formed at the expense of a same FA pool characteristic of a given species and were strongly different from FAIPEs and FABEs esters regarding the mechanism of their biosynthesis. However, as a whole, the qualitative and quantitative composition of various FASCAE fractions, as well as their FA composition, varied considerably depending on various factors. Therefore, separate FASCAE fractions seem to be synthesized from different FA pools other than those used for triacylglycerol formation. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.

Evaluation of certain food additives. Seventy-first report of the Joint FAO/WHO Expert Committee on Food Additives.

PubMed

2010-01-01

This report represents the conclusions of a Joint FAO/WHO Expert Committee convened to evaluate the safety of various food additives, with a view to recommending acceptable daily intakes (ADIs) and to preparing specifications for identity and purity. The first part of the report contains a general discussion of the principles governing the toxicological evaluation and assessment of intake of food additives. A summary follows of the Committee's evaluations of technical, toxicological and intake data for certain food additives: branching glycosyltransferase from Rhodothermus obamensis expressed in Bacillus subtilis, cassia gum, cyclamic acid and its salts (dietary exposure assessment), cyclotetraglucose and cyclotetraglucose syrup, ferrous ammonium phosphate, glycerol ester of gum rosin, glycerol ester of tall oil rosin, lycopene from all sources, lycopene extract from tomato, mineral oil (low and medium viscosity) class II and class III, octenyl succinic acid modified gum arabic, sodium hydrogen sulfate and sucrose oligoesters type I and type II. Specifications for the following food additives were revised: diacetyltartaric acid and fatty acid esters of glycerol, ethyl lauroyl arginate, glycerol ester of wood rosin, nisin preparation, nitrous oxide, pectins, starch sodium octenyl succinate, tannic acid, titanium dioxide and triethyl citrate. Annexed to the report are tables summarizing the Committee's recommendations for intakes and toxicological evaluations of the food additives considered.

Lipase-Catalyzed Production of 6-O-cinnamoyl-sorbitol from D-sorbitol and Cinnamic Acid Esters.

PubMed

Kim, Jung-Ho; Bhatia, Shashi Kant; Yoo, Dongwon; Seo, Hyung Min; Yi, Da-Hye; Kim, Hyun Joong; Lee, Ju Hee; Choi, Kwon-Young; Kim, Kwang Jin; Lee, Yoo Kyung; Yang, Yung-Hun

2015-05-01

To overcome the poor properties of solubility and stability of cinnamic acid, cinnamate derivatives with sugar alcohols were produced using the immobilized Candida antarctica lipase with vinyl cinnamate and D-sorbitol as substrate at 45 °C. Immobilized C. antarctica lipase was found to synthesize 6-O-cinnamoyl-sorbitol and confirmed by HPLC and (1)H-NMR and had a preference for vinyl cinnamate over other esters such as allyl-, ethyl-, and isobutyl cinnamate as co-substrate with D-sorbitol. Contrary to D-sorbitol, vinyl cinnamate, and cinnamic acid, the final product 6-O-cinnamoyl-sorbitol was found to have radical scavenging activity. This would be the first report on the biosynthesis of 6-O-cinnamoyl-sorbitol with immobilized enzyme from C. antarctica.

Investigations of vibrational spectra and bioactivity of novel anticancer drug N-(6-ferrocenyl-2-naphthoyl)-gamma-amino butyric acid ethyl ester

NASA Astrophysics Data System (ADS)

Sudhi, Geethu; Rajina, S. R.; Praveen, S. G.; Xavier, T. S.; Kenny, Peter T. M.; Jaiswal-Nagar, D.; Binoy, J.

2017-10-01

The bioactivity of compounds is mainly dependent on molecular structure and the present work aims to explore the bonding features responsible for biological activity of novel anticancer drug N-(6-ferrocenyl-2-naphthoyl)-gamma-amino butyric acid ethyl ester (FNGABEE). In the present study, we investigate the molecular structural properties of newly synthesized title compound through experimental and quantum chemical studies. The detailed vibrational analysis has been performed using FT IR and FT Raman spectrum, aided by DFT computed geometry, vibrational spectrum, Eigen vector distribution and PED, at B3LYP/6-311 ++G(d,p) level. The resonance structure of naphthalene, different from that of benzene, revealed by molecular structure has been investigated using Csbnd C and Cdbnd C stretching modes. The proton transfer in amide has been analyzed to obtain spectral distinction between different carbonyl and Csbnd N groups which point to the reactive sites responsible for binding with DNA and bovine serum albumin (BSA). The spectral distinction between eclipsed and staggered form of ferrocene has been analyzed. The molecular docking of FNGABEE with BSA and DNA has been performed to find the strength of binding and the moieties responsible for the interactions. The experimental binding studies of FNGABEE with BSA and DNA has been performed using UV absorption spectroscopy and fluorometric assay, to find the nature and strength of binding.

Determination of fatty acid ethyl esters (FAEE) and ethyl glucuronide (EtG) in hair: a promising way for retrospective detection of alcohol abuse during pregnancy?

PubMed

Pragst, Fritz; Yegles, Michel

2008-04-01

The retrospective detection of alcohol consumption during pregnancy is an important part of the diagnosis of the fetal alcohol syndrome. A promising way to solve this problem can be the determination of fatty acid ethyl esters (FAEE) or/and ethyl glucuronide (EtG) in hair of the mothers. In this article, the present state in analytical determination and interpretation of FAEE and EtG concentrations in hair are reviewed. Both FAEE and EtG are minor metabolites of ethanol and as direct alcohol markers very specific for alcohol. They are durably deposited in hair, which enables taking advantage of the long diagnostic time window of this sample material. In the last years, specific and sensitive methods for determination of both alcohol markers in hair were developed. Headspace solid phase microextraction in combination with gas chromatography-mass spectroscopy after hair extraction with an n-heptane/dimethylsulfoxide mixture proved to be a favorable technique for determination of four characteristic FAEE (ethyl myristate, ethyl palmitate, ethyl oleate, and ethyl stearate). EtG is extracted from hair by water and analyzed either by gas chromatography-mass spectroscopy with negative chemical ionization after cleanup with solid phase extraction and derivatization with pentafluoropropionic anhydride or by liquid chromatography-mass spectroscopy-mass spectroscopy. The detection limits of the single FAEE as well as of EtG are in the range of 1 to 10 pg/mg. FAEE as well as EtG were determined in a larger number of hair samples of teetotalers, social drinkers, patients in alcohol withdrawal treatment, and death cases with previous known heavy drinking. From the results, the following criteria were derived: strict abstinence is excluded or improbable at C FAEE >0.2 ng/mg or C EtG >7 pg/mg. Moderate social drinkers should have C FAEE <0.5 ng/mg and C EtG <25 pg/mg; above these values, alcohol abuse is probable. Until now, there has been no evaluation in context of FAS diagnosis; however, a successful application for this purpose can be expected from the good experience in driving ability examination.

Efficacy and Safety of Omega-3/6 Fatty Acids, Methylphenidate, and a Combined Treatment in Children With ADHD.

PubMed

Barragán, Eduardo; Breuer, Dieter; Döpfner, Manfred

2017-03-01

To compare efficacy of Omega-3/6 fatty acids (Equazen eye q™) with methylphenidate (MPH) and combined MPH + Omega-3/6 in children with ADHD. Participants ( N = 90) were randomized to Omega-3/6, long-acting MPH, or combination for 12 months. ADHD symptoms were assessed using the ADHD Rating Scale and Clinical Global Impressions-Severity (CGI-S) scale. ADHD symptoms decreased in all treatment arms. Although significant differences favoring Omega + MPH over Omega-3/6 alone were found for ADHD Total and Hyperactivity-Impulsivity subscales, results on the Inattention subscale were similar. CGI-S scores decreased slowly and consistently with Omega-3/6, compared with a rapid decrease and subsequent slight increase in the MPH-containing arms. Adverse events were numerically less frequent with Omega-3/6 or MPH + Omega-3/6 than MPH alone. The tested combination of Omega-3/6 fatty acids had similar effects to MPH, whereas the MPH + Omega combination appeared to have some tolerability benefits over MPH.

Effect of omega-3 fatty acids on the modification of erythrocyte membrane fatty acid content including oleic acid in peritoneal dialysis patients.

PubMed

An, W S; Lee, S M; Son, Y K; Kim, S E; Kim, K H; Han, J Y; Bae, H R; Park, Y

2012-01-01

Erythrocyte membrane fatty acids (FA), such as oleic acid, are related to acute coronary syndrome. There is no report about the effect of omega-3 FA on oleic acid in peritoneal dialysis (PD) patients. We hypothesized that omega-3 FA can modify erythrocyte membrane FA, including oleic acid, in PD patients. In a double-blind, randomized, placebo-controlled study, 18 patients who were treated with PD for at least 6 months were randomized to treatment for 12 weeks with omega-3 FA or placebo. Erythrocyte membrane FA content was measured by gas chromatography at baseline and after 12 weeks. The erythrocyte membrane content of eicosapentaenoic acid and docosahexaenoic acid was significantly increased and saturated FA and oleic acid were significantly decreased in the omega-3 FA supplementation group after 12 weeks compared to baseline. In conclusion, erythrocyte membrane FA content, including oleic acid, was significantly modified by omega-3 FA supplementation for 12 weeks in PD patients. Copyright © 2011 Elsevier Ltd. All rights reserved.

40 CFR 721.10690 - Benzenedicarboxylic acid, polymer with substituted alkanediol, dodecanedioic acid, 1,2-ethanediol...

Code of Federal Regulations, 2014 CFR

2014-07-01

..., alkanediol,.alpha.-hydro-.omega.-hydroxypoly[oxyalkanediyl], 1,3-isobenzofurandione, methylene diphenyl...-ethanediol, alkanedioic acid, alkanediol,.alpha.-hydro-.omega.-hydroxypoly[oxyalkanediyl], 1,3... substituted alkanediol, dodecanedioic acid, 1,2-ethanediol, alkanedioic acid, alkanediol,.alpha.-hydro-.omega...

Combined effects of nutrients and temperature on the production of fermentative aromas by Saccharomyces cerevisiae during wine fermentation.

PubMed

Rollero, Stéphanie; Bloem, Audrey; Camarasa, Carole; Sanchez, Isabelle; Ortiz-Julien, Anne; Sablayrolles, Jean-Marie; Dequin, Sylvie; Mouret, Jean-Roch

2015-03-01

Volatile compounds produced by yeast during fermentation greatly influence the organoleptic qualities of wine. We developed a model to predict the combined effects of initial nitrogen and phytosterol content and fermentation temperature on the production of volatile compounds. We used a Box-Behnken design and response surface modeling to study the response of Lalvin EC1118® to these environmental conditions. Initial nitrogen content had the greatest influence on most compounds; however, there were differences in the value of fermentation parameters required for the maximal production of the various compounds. Fermentation parameters affected differently the production of isobutanol and isoamyl alcohol, although their synthesis involve the same enzymes and intermediate. We found differences in regulation of the synthesis of acetates of higher alcohols and ethyl esters, suggesting that fatty acid availability is the main factor influencing the synthesis of ethyl esters whereas the production of acetates depends on the activity of alcohol acetyltransferases. We also evaluated the effect of temperature on the total production of three esters by determining gas-liquid balances. Evaporation largely accounted for the effect of temperature on the accumulation of esters in liquid. Nonetheless, the metabolism of isoamyl acetate and ethyl octanoate was significantly affected by this parameter. We extended this study to other strains. Environmental parameters had a similar effect on aroma production in most strains. Nevertheless, the regulation of the synthesis of fermentative aromas was atypical in two strains: Lalvin K1M® and Affinity™ ECA5, which produces a high amount of aromatic compounds and was obtained by experimental evolution.

Effect of Increased Yeast Alcohol Acetyltransferase Activity on Flavor Profiles of Wine and Distillates

PubMed Central

Lilly, M.; Lambrechts, M. G.; Pretorius, I. S.

2000-01-01

The distinctive flavor of wine, brandy, and other grape-derived alcoholic beverages is affected by many compounds, including esters produced during alcoholic fermentation. The characteristic fruity odors of the fermentation bouquet are primarily due to a mixture of hexyl acetate, ethyl caproate (apple-like aroma), iso-amyl acetate (banana-like aroma), ethyl caprylate (apple-like aroma), and 2-phenylethyl acetate (fruity, flowery flavor with a honey note). The objective of this study was to investigate the feasibility of improving the aroma of wine and distillates by overexpressing one of the endogenous yeast genes that controls acetate ester production during fermentation. The synthesis of acetate esters by the wine yeast Saccharomyces cerevisiae during fermentation is ascribed to at least three acetyltransferase activities, namely, alcohol acetyltransferase (AAT), ethanol acetyltransferase, and iso-amyl AAT. To investigate the effect of increased AAT activity on the sensory quality of Chenin blanc wines and distillates from Colombar base wines, we have overexpressed the alcohol acetyltransferase gene (ATF1) of S. cerevisiae. The ATF1 gene, located on chromosome XV, was cloned from a widely used commercial wine yeast strain of S. cerevisiae, VIN13, and placed under the control of the constitutive yeast phosphoglycerate kinase gene (PGK1) promoter and terminator. Chromoblot analysis confirmed the integration of the modified copy of ATF1 into the genome of three commercial wine yeast strains (VIN7, VIN13, and WE228). Northern blot analysis indicated constitutive expression of ATF1 at high levels in these yeast transformants. The levels of ethyl acetate, iso-amyl acetate, and 2-phenylethyl acetate increased 3- to 10-fold, 3.8- to 12-fold, and 2- to 10-fold, respectively, depending on the fermentation temperature, cultivar, and yeast strain used. The concentrations of ethyl caprate, ethyl caprylate, and hexyl acetate only showed minor changes, whereas the acetic acid concentration decreased by more than half. These changes in the wine and distillate composition had a pronounced effect on the solvent or chemical aroma (associated with ethyl acetate and iso-amyl acetate) and the herbaceous and heads-associated aromas of the final distillate and the solvent or chemical and fruity or flowery characters of the Chenin blanc wines. This study establishes the concept that the overexpression of acetyltransferase genes such as ATF1 could profoundly affect the flavor profiles of wines and distillates deficient in aroma, thereby paving the way for the production of products maintaining a fruitier character for longer periods after bottling. PMID:10653746

A randomised trial of the effect of omega-3 polyunsaturated fatty acid supplements on the human intestinal microbiota.

PubMed

Watson, Henry; Mitra, Suparna; Croden, Fiona C; Taylor, Morag; Wood, Henry M; Perry, Sarah L; Spencer, Jade A; Quirke, Phil; Toogood, Giles J; Lawton, Clare L; Dye, Louise; Loadman, Paul M; Hull, Mark A

2017-09-26

Omega-3 polyunsaturated fatty acids (PUFAs) have anticolorectal cancer (CRC) activity. The intestinal microbiota has been implicated in colorectal carcinogenesis. Dietary omega-3 PUFAs alter the mouse intestinal microbiome compatible with antineoplastic activity. Therefore, we investigated the effect of omega-3 PUFA supplements on the faecal microbiome in middle-aged, healthy volunteers (n=22). A randomised, open-label, cross-over trial of 8 weeks' treatment with 4 g mixed eicosapentaenoic acid/docosahexaenoic acid in two formulations (soft-gel capsules and Smartfish drinks), separated by a 12-week 'washout' period. Faecal samples were collected at five time-points for microbiome analysis by 16S ribosomal RNA PCR and Illumina MiSeq sequencing. Red blood cell (RBC) fatty acid analysis was performed by liquid chromatography tandem mass spectrometry. Both omega-3 PUFA formulations induced similar changes in RBC fatty acid content, except that drinks were associated with a larger, and more prolonged, decrease in omega-6 PUFA arachidonic acid than the capsule intervention (p=0.02). There were no significant changes in α or β diversity, or phyla composition, associated with omega-3 PUFA supplementation. However, a reversible increased abundance of several genera, including Bifidobacterium , Roseburia and Lactobacillus was observed with one or both omega-3 PUFA interventions. Microbiome changes did not correlate with RBC omega-3 PUFA incorporation or development of omega-3 PUFA-induced diarrhoea. There were no treatment order effects. Omega-3 PUFA supplementation induces a reversible increase in several short-chain fatty acid-producing bacteria, independently of the method of administration. There is no simple relationship between the intestinal microbiome and systemic omega-3 PUFA exposure. ISRCTN18662143. © Article author(s) (or their employer(s) unless otherwise stated in the text of the article) 2017. All rights reserved. No commercial use is permitted unless otherwise expressly granted.

Monitoring of BHT-quinone and BHT-CHO in the gas of capsules of Asclepias physocarpa.

PubMed

Ma, Bing-Ji; Peng, Hua; Liu, Ji-Kai

2006-01-01

Three volatile components, namely benzoic acid ethyl ester (1), 2,6-di-tert-butyl-p-benzoquinone (BHT-quinone) (2), and 3,5-di-tert-butyl-4-hydroxybenzaldehyde (BHT-CHO) (3), were detected from the gas in the capsules of Asclepias physocarpa by means of GC/MS analysis. BHT-quinone and BHT-CHO as organic pollutants are the degradation products of the antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT). Ground water, lake water and/or rain water are a source of BHT metabolites in the plant Asclepias physocarpa.

Foraging behavior of the dead leaf butterfly, Kallima inachus.

PubMed

Tang, Yuchong; Zhou, Chengli; Chen, Xiaoming; Zheng, Hua

2013-01-01

The behavioral responses of foraging adults of Kallima inachus (Boisduval) (Lepidoptera: Nymphalidae) to four colors and to six different fermented fruit juices were observed in order to determine the cues used by foraging adults. According to the results, adults did not show a behavioral response to red, yellow, purple, or white artificial flowers without food odors, but flowers with the fermented pear juice strongly attracted them, and they showed a behavioral response to fermented juices of the six fruits (pear, apple, banana, watermelon, orange, and persimmon) with no statistically significant preference. The fruit volatiles were collected using dynamic headspace adsorption, and the volatile components were analyzed by auto thermal-desorption gas chromatography-mass spectrometry to assess which volatiles existed in the fruits. Only alcohols, esters, and ketones were common in the volatiles of all six fermenting fruits. The five volatile components found in the six fruits, as well as two others found to be in other fermented foods by previous studies, were selected to test the behavioral and electroantennogram (EAG) responses of naive adults to estimate behavioral preference and antennal perception. In field behavioral tests, alcohols were the most attractive, followed by esters, while α-pinene, butanone, and acetic acid were much less attractive. Relative to other volatile combinations and ethanol alone, the mixture of ethyl acetate and ethanol attracted the most feeding adults. The number of adults attracted was significantly positively correlated with the concentration of both ethanol and ethyl acetate. The EAG responses of naive adults showed that the EAG responses to 3-methyl-1-butanol, isoamyl acetate, ethyl acetate, α-pinene, butanone, and acetic acid were all higher than those to ethanol (100%) at doses of either 5 µl/mL or 50 µl/mL. Sexual differences only existed in 3-methyl-1-butanol and acetic acid at particular concentrations. Sexual differences in response to chemical mixtures were not significant at 50 µl/mL. In addition, the EAG responses in the within-sex trials were not correlated to the dosage (0.01, 0.1, 1, 5, 10, and µl/mL) of either ethanol or ethyl acetate. The results showed that olfactory cues played a crucial role in the foraging of adult K. inachus, and that foraging adults can use a variety of chemical signals derived from food; however, the feeding preference to volatiles was not necessary correlated with the EAG responses.

Effect of drug lipophilicity on in vitro release rate from oil vehicles using nicotinic acid esters as model prodrug derivatives.

PubMed

Weng Larsen, S; Engelbrecht Thomsen, A E; Rinvar, E; Friis, G J; Larsen, C

2001-03-23

The rate constants for transfer of a homologous series of nicotinic acid esters from oil vehicles to aqueous buffer phases were determined using a rotating dialysis cell. The chemical stability of butyl nicotinate has been investigated at 60 degrees C over pH range 0.5--10. Maximum stability occurs at pH 4--5 and an inflection point was seen around the pK(a). For the nicotinic acid esters, a linear correlation was established between the first-order rate constant related to attainment of equilibrium, k(obs) and the apparent partition coefficient, P(app): log k(obs)=-0.83log P(app)+0.26 (k(obs) in h(-1), n=9). For hexyl nicotinate with a true partition coefficient of 4 it was possible to determine k(obs) by decreasing pH in the aqueous release medium to 2.05. Thus, under the latter experimental conditions estimation of the relative release rates for the esters were performed. The ratio between the specific rate constant k(ow), related to the transport from oil vehicle to aqueous phase, for ethyl and hexyl nicotinate was 139. The hydrophobic substituent constant for a methylene group, pi(CH(2)), was determined for nicotinic acid esters in different oil/buffer partitioning systems to 0.54--0.58. Addition of hydroxypropyl-beta-cyclodextrin to the aqueous release medium did not enhance the transport rate of the esters from the oil phase.

Plasma eicosapentaenoic acid is negatively associated with all-cause mortality among men and women in a population-based prospective study.

PubMed

Miura, Kyoko; Hughes, Maria Celia B; Ungerer, Jacobus Pj; Green, Adèle C

2016-11-01

Omega-3 polyunsaturated fatty acids (PUFAs) have anti-inflammatory properties, whereas omega-6 PUFAs appear to have proinflammatory properties. We aimed to assess plasma omega-3 and omega-6 PUFA status in relation to all-cause mortality in an Australian community-based study. We hypothesized that omega-3 PUFA would be inversely associated, and omega-6 PUFA positively associated with all-cause mortality. Plasma phospholipid omega-3 (eicosapentaenoic acid [EPA], docosapentaenoic acid [DPA], docosahexaenoic acid, α-linolenic acid, and total) and omega-6 PUFAs (linoleic acid, arachidonic acid, and total) were measured among 1008 adults (44% men) in 1996. Plasma PUFA composition was quantified using gas chromatography. During 17-year follow-up, 98 men and 81 women died. After adjustment for potential confounding factors, plasma EPA was inversely associated with all-cause mortality overall (adjusted hazard ratio [HR] per 1-SD increase, 0.81; 95% confidence interval [CI], 0.68-0.95), in men (HR, 0.78; 95% CI, 0.62-0.98), and in women (HR, 0.78; 95% CI, 0.65-0.94), separately. Inverse associations with mortality among men were also seen for DPA (HR, 0.76; 95% CI, 0.60-0.97) and α-linolenic acid (HR, 0.73; 95% CI, 0.57-0.94). No omega-6 PUFAs were significantly associated with mortality. Our findings of reduced all-cause mortality in men and women who have high EPA in plasma, and in men with high plasma DPA and α-linolenic acid, partially support our hypothesis that omega-3 PUFAs help reduce mortality but provide no evidence that omega-6 PUFAs may increase mortality. Copyright © 2016 Elsevier Inc. All rights reserved.

Bioengineered Plants Can Be a Useful Source of Omega-3 Fatty Acids

PubMed Central

Lyu, Shan-Wu

2017-01-01

Omega-3 fatty acids have proven to be very essential for human health due to their multiple health benefits. These essential fatty acids (EFAs) need to be uptaken through diet because they are unable to be produced by the human body. These are important for skin and hair growth as well as for proper visual, neural, and reproductive functions of the body. These fatty acids are proven to be extremely vital for normal tissue development during pregnancy and infancy. Omega-3 fatty acids can be obtained mainly from two dietary sources: marine and plant oils. Eicosapentaenoic acid (EPA; C20:5 n-3) and docosahexaenoic acid (DHA; C22:6 n-3) are the primary marine-derived omega-3 fatty acids. Marine fishes are high in omega-3 fatty acids, yet high consumption of those fishes will cause a shortage of fish stocks existing naturally in the oceans. An alternative source to achieve the recommended daily intake of EFAs is the demand of today. In this review article, an attempt has, therefore, been made to discuss the importance of omega-3 fatty acids and the recent developments in order to produce these fatty acids by the genetic modifications of the plants. PMID:28316988

Bioengineered Plants Can Be a Useful Source of Omega-3 Fatty Acids.

PubMed

Amjad Khan, Waleed; Chun-Mei, Hu; Khan, Nadeem; Iqbal, Amjad; Lyu, Shan-Wu; Shah, Farooq

2017-01-01

Omega-3 fatty acids have proven to be very essential for human health due to their multiple health benefits. These essential fatty acids (EFAs) need to be uptaken through diet because they are unable to be produced by the human body. These are important for skin and hair growth as well as for proper visual, neural, and reproductive functions of the body. These fatty acids are proven to be extremely vital for normal tissue development during pregnancy and infancy. Omega-3 fatty acids can be obtained mainly from two dietary sources: marine and plant oils. Eicosapentaenoic acid (EPA; C20:5 n-3) and docosahexaenoic acid (DHA; C22:6 n-3) are the primary marine-derived omega-3 fatty acids. Marine fishes are high in omega-3 fatty acids, yet high consumption of those fishes will cause a shortage of fish stocks existing naturally in the oceans. An alternative source to achieve the recommended daily intake of EFAs is the demand of today. In this review article, an attempt has, therefore, been made to discuss the importance of omega-3 fatty acids and the recent developments in order to produce these fatty acids by the genetic modifications of the plants.

Anti-inflammatory effects of omega 3 and omega 6 polyunsaturated fatty acids in cardiovascular disease and metabolic syndrome.

PubMed

Tortosa-Caparrós, Esther; Navas-Carrillo, Diana; Marín, Francisco; Orenes-Piñero, Esteban

2017-11-02

A lipid excess produces a systemic inflammation process due to tumor necrosis factor-α, interleukin-6 and C-reactive protein synthesis. Simultaneously, this fat excess promotes the appearance of insulin resistance. All this contributes to the development of atherosclerosis and increases the risk of cardiovascular diseases (CVDs). On the other hand, polyunsaturated fatty acids (PUFAs), especially eicosapentaenoic acid and docosahexaenoic acid (omega 3), and arachidonic acid (omega 6) have shown anti-inflammatory properties. Lately, an inverse relationship between omega-3 fatty acids, inflammation, obesity and CVDs has been demonstrated. To check fatty acids effect, the levels of some inflammation biomarkers have been analyzed. Leptin, adiponectin and resistin represent a group of hormones associated with the development of CVDs, obesity, type 2 diabetes mellitus and insulin resistance and are modified in obese/overweight people comparing to normal weight people. Omega-3 PUFAs have been shown to decrease the production of inflammatory mediators, having a positive effect in obesity and diabetes mellitus type-2. Moreover, they significantly decrease the appearance of CVD risk factors. Regarding omega-6 PUFA, there is controversy whether their effects are pro- or anti-inflammatory. The aim of this manuscript is to provide a comprehensive overview about the role of omega-3 and omega-6 PUFAs in CVDs and metabolic syndrome.

Potential adverse effects of omega-3 Fatty acids in dogs and cats.

PubMed

Lenox, C E; Bauer, J E

2013-01-01

Fish oil omega-3 fatty acids, mainly eicosapentaenoic acid and docosahexaenoic acid, are used in the management of several diseases in companion animal medicine, many of which are inflammatory in nature. This review describes metabolic differences among omega-3 fatty acids and outlines potential adverse effects that may occur with their supplementation in dogs and cats with a special focus on omega-3 fatty acids from fish oil. Important potential adverse effects of omega-3 fatty acid supplementation include altered platelet function, gastrointestinal adverse effects, detrimental effects on wound healing, lipid peroxidation, potential for nutrient excess and toxin exposure, weight gain, altered immune function, effects on glycemic control and insulin sensitivity, and nutrient-drug interactions. Copyright © 2013 by the American College of Veterinary Internal Medicine.

Fish oil and postoperative atrial fibrillation: the Omega-3 Fatty Acids for Prevention of Post-operative Atrial Fibrillation (OPERA) randomized trial.

PubMed

Mozaffarian, Dariush; Marchioli, Roberto; Macchia, Alejandro; Silletta, Maria G; Ferrazzi, Paolo; Gardner, Timothy J; Latini, Roberto; Libby, Peter; Lombardi, Federico; O'Gara, Patrick T; Page, Richard L; Tavazzi, Luigi; Tognoni, Gianni

2012-11-21

Postoperative atrial fibrillation or flutter (AF) is one of the most common complications of cardiac surgery and significantly increases morbidity and health care utilization. A few small trials have evaluated whether long-chain n-3-polyunsaturated fatty acids (PUFAs) reduce postoperative AF, with mixed results. To determine whether perioperative n-3-PUFA supplementation reduces postoperative AF. The Omega-3 Fatty Acids for Prevention of Post-operative Atrial Fibrillation (OPERA) double-blind, placebo-controlled, randomized clinical trial. A total of 1516 patients scheduled for cardiac surgery in 28 centers in the United States, Italy, and Argentina were enrolled between August 2010 and June 2012. Inclusion criteria were broad; the main exclusions were regular use of fish oil or absence of sinus rhythm at enrollment. Patients were randomized to receive fish oil (1-g capsules containing ≥840 mg n-3-PUFAs as ethyl esters) or placebo, with preoperative loading of 10 g over 3 to 5 days (or 8 g over 2 days) followed postoperatively by 2 g/d until hospital discharge or postoperative day 10, whichever came first. Occurrence of postoperative AF lasting longer than 30 seconds. Secondary end points were postoperative AF lasting longer than 1 hour, resulting in symptoms, or treated with cardioversion; postoperative AF excluding atrial flutter; time to first postoperative AF; number of AF episodes per patient; hospital utilization; and major adverse cardiovascular events, 30-day mortality, bleeding, and other adverse events. At enrollment, mean age was 64 (SD, 13) years; 72.2% of patients were men, and 51.8% had planned valvular surgery. The primary end point occurred in 233 (30.7%) patients assigned to placebo and 227 (30.0%) assigned to n-3-PUFAs (odds ratio, 0.96 [95% CI, 0.77-1.20]; P = .74). None of the secondary end points were significantly different between the placebo and fish oil groups, including postoperative AF that was sustained, symptomatic, or treated (231 [30.5%] vs 224 [29.6%], P = .70) or number of postoperative AF episodes per patient (1 episode: 156 [20.6%] vs 157 [20.7%]; 2 episodes: 59 [7.8%] vs 49 [6.5%]; ≥3 episodes: 18 [2.4%] vs 21 [2.8%]) (P = .73). Supplementation with n-3-PUFAs was generally well tolerated, with no evidence for increased risk of bleeding or serious adverse events. In this large multinational trial among patients undergoing cardiac surgery, perioperative supplementation with n-3-PUFAs, compared with placebo, did not reduce the risk of postoperative AF. TRIAL REGISTRATION clinicaltrials.gov Identifier: NCT00970489.

Effect of ω-3 fatty acid ethyl esters on apolipoprotein B-48 kinetics in obese subjects on a weight-loss diet: a new tracer kinetic study in the postprandial state.

PubMed

Wong, Annette T Y; Chan, Dick C; Barrett, P Hugh R; Adams, Leon A; Watts, Gerald F

2014-08-01

Dysregulated chylomicron metabolism may account for hypertriglyceridemia and increased risk of cardiovascular disease in obese subjects. Supplementation with ω-3 fatty acid ethyl ester (FAEE) decreases plasma triglyceride. However, its effect on postprandial chylomicron metabolism in obese subjects on a weight-loss diet has not yet been investigated. We aimed to examine the effect of ω-3 FAEE supplementation on apolipoprotein (apo) B-48 kinetics in obese subjects on a weight-loss diet. We carried out a 12-week, randomized trial of a hypocaloric diet plus 4 g/d ω-3 FAEE supplementation (46% eicosapentaenoic acid and 38% docosahexaenoic acid) (n = 13) compared with a hypocaloric diet alone (n = 12) on postprandial apoB-48 kinetics in obese subjects after ingestion of an oral load. The apoB-48 kinetics were determined using stable isotope tracer kinetics and multicompartmental modeling. We evaluated plasma total and incremental apoB-48 0- to 10-hour area under the curves (AUCs) as well as apoB-48 secretion and fractional catabolic rate. Weight loss with or without ω-3 FAEE supplementation significantly reduced body weight, total fat mass, homeostasis model assessment score, fasting triglyceride concentration, postprandial triglyceride AUC, and increased plasma high-density lipoprotein cholesterol concentration (P < .05 in all). Compared with weight loss alone, weight loss plus ω-3 FAEE significantly (all P < .05) decreased fasting triglyceride (-11%), apoB-48 (-36%) concentrations, postprandial triglyceride (-21%), and apoB-48 (-22%) total AUCs, as well as incremental postprandial triglyceride AUCs (-32%). The ω-3 FAEE also significantly decreased apoB-48 secretion in the basal state, without a significant effect during the postprandial period (3-6 hours). The fractional catabolic rate of apoB-48 increased with both interventions with no significant independent effect of ω-3 FAEE supplementation. Addition of ω-3 FAEE supplementation to a moderate weight-loss diet in obese subjects can significantly improve chylomicron metabolism by independently decreasing the secretion of apoB-48.

pH-Dependent Stability of Creatine Ethyl Ester: Relevance to Oral Absorption

PubMed Central

Gufford, Brandon T.; Ezell, Edward L.; Robinson, Dennis H.; Miller, Donald W.; Miller, Nicholas J.; Gu, Xiaochen; Vennerstrom, Jonathan L.

2015-01-01

Creatine ethyl ester hydrochloride (CEE) was synthesized as a prodrug of creatine (CRT) to improve aqueous solubility, gastrointestinal permeability, and ultimately the pharmacodynamics of CRT. We used high-performance liquid chromatography (HPLC) and proton nuclear magnetic resonance (NMR) to characterize the pH-dependent stability of CEE in aqueous solution and compared the permeability of CEE to CRT and creatinine (CRN) across Caco-2 human epithelial cell monolayers and transdermal permeability across porcine skin. CEE was most stable in a strongly acidic condition (half-life = 570 hours at pH 1.0) where it undergoes ester hydrolysis to CRT and ethanol. At pH ≥ 1.0, CEE cyclizes to CRN with the logarithm of the first order rate constant increasing linearly with pH. Above pH 8.0 (half-life = 23 sec) the rate of degradation was too rapid to be determined. The rate of degradation of CEE in cell culture media and simulated intestinal fluid (SIF) was a function of pH and correlated well with the stability in aqueous buffered solutions. The permeability of CEE across Caco-2 monolayers and porcine skin was significantly greater than that of CRT or CRN. The stability of CEE in acidic media together with its improved permeability suggests that CEE has potential for improved oral absorption compared to CRT. PMID:23957855

Design, synthesis and biological evaluation of novel quinazoline-2,4-diones conjugated with different amino acids as potential chitin synthase inhibitors.

PubMed

Noureldin, Nada A; Kothayer, Hend; Lashine, El-Sayed M; Baraka, Mohamed M; Huang, Yanrong; Li, Bing; Ji, Qinggang

2018-05-25

A series of (2-(1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl) acetamido) acids) (6 a-m), (7) has been designed to inhibit the action of fungus chitin synthase enzyme (CHS). The synthesis of the designed compounds was carried out in four steps starting from the reaction between 1-methylquinazoline-2,4(1H,3H)-dione and ethyl chloroacetate to yield the ethyl acetate derivative. This ester was hydrolyzed to the corresponding carboxylic acid derivative that was then utilized to couple several amino acids getting the final designed compounds. The synthesized compounds were tested for their inhibition against CHS. Compound 7 showed the highest potency among others with minimum inhibitory concentration (IC 50 ) of 0.166 mmol/L, while polyoxin B (the positive control) had IC 50 of 0.17 mmol/L. The synthesized compounds were also evaluated for their in vitro antifungal activity using Aspergillus fumigates, Aspergillus flavus, Crytococcus neoformans and Candida albicans. Unfortunately, the 14 synthesized compounds showed lower in vitro activity compared to the used active controls. However, compound 6m and fluconazole have synergistic effect on Aspergillus flavus; Compounds 7 and fluconazole have synergistic effects on Aspergillus fumigates. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Omega-3 fatty acids: cardiovascular benefits, sources and sustainability.

PubMed

Lee, John H; O'Keefe, James H; Lavie, Carl J; Harris, William S

2009-12-01

The evidence for the cardioprotective nature of omega-3 fatty acids is abundant, and currently available data indicate that patients with known coronary heart disease should consume at least 1 g daily of long-chain omega-3 fatty acids from either oily fish or fish-oil supplements, and that individuals without disease should consume at least 250-500 mg daily. However, this area of research poses two questions. Firstly, which is the best source of omega-3 fatty acids-fish or fish-oil supplements? Secondly, are recommendations for omega-3 supplementation warranted in view of the rapid depletion of world fish stocks? The argument that eating fish is better than taking fish-oil supplements stems from the fact that several important nutrients, such as vitamin D, selenium, and antioxidants, are missing from the supplements. However, three major prevention trials have clearly indicated that omega-3 fatty acid capsules confer cardiovascular benefits and, therefore, that both are cardioprotective. Sustainable sources of omega-3 fatty acids will need to be identified if long-term cardiovascular risk reduction is to be achieved at the population level.

Fishy business: effect of omega-3 fatty acids on zinc transporters and free zinc availability in human neuronal cells.

PubMed

De Mel, Damitha; Suphioglu, Cenk

2014-08-15

Omega-3 (ω-3) fatty acids are one of the two main families of long chain polyunsaturated fatty acids (PUFA). The main omega-3 fatty acids in the mammalian body are α-linolenic acid (ALA), docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). Central nervous tissues of vertebrates are characterized by a high concentration of omega-3 fatty acids. Moreover, in the human brain, DHA is considered as the main structural omega-3 fatty acid, which comprises about 40% of the PUFAs in total. DHA deficiency may be the cause of many disorders such as depression, inability to concentrate, excessive mood swings, anxiety, cardiovascular disease, type 2 diabetes, dry skin and so on. On the other hand, zinc is the most abundant trace metal in the human brain. There are many scientific studies linking zinc, especially excess amounts of free zinc, to cellular death. Neurodegenerative diseases, such as Alzheimer's disease, are characterized by altered zinc metabolism. Both animal model studies and human cell culture studies have shown a possible link between omega-3 fatty acids, zinc transporter levels and free zinc availability at cellular levels. Many other studies have also suggested a possible omega-3 and zinc effect on neurodegeneration and cellular death. Therefore, in this review, we will examine the effect of omega-3 fatty acids on zinc transporters and the importance of free zinc for human neuronal cells. Moreover, we will evaluate the collective understanding of mechanism(s) for the interaction of these elements in neuronal research and their significance for the diagnosis and treatment of neurodegeneration.

Remarkable magnitude of the self-disproportionation of enantiomers (SDE) via achiral chromatography: application to the practical-scale enantiopurification of β-amino acid esters.

PubMed

Wzorek, Alicja; Sato, Azusa; Drabowicz, Józef; Soloshonok, Vadim A; Klika, Karel D

2016-02-01

We report the best performance yet for the self-disproportionation of enantiomers (SDE) via achiral chromatography as typically used in laboratories for the isolated yield of the excess enantiomer using N-acetyl β-amino acid ethyl esters. The results are the most convincing ever demonstration of the capability of the SDE for practical-scale enantiopurification as comparable, or even superior for some systems, to that of recrystallization. For example, from a sample of 94.4 % ee, a yield of 71 % of enantiopure material was isolated in a single chromatographic run. Moreover, the lack of an esoteric structural entity, e.g. strongly polarizing groups, such as, for instance CF3, highlights the fact that the phenomenon is not dependent on the presence of such and thus the process is relevant to any usual-type structure. In contrast to recrystallization, the procedure is predictable, general, and dependable, boding well for its widespread application in routine laboratory settings.

Effects of Different Lipophilized Ferulate Esters in Fish Oil-Enriched Milk: Partitioning, Interaction, Protein, and Lipid Oxidation.

PubMed

Qiu, Xujian; Jacobsen, Charlotte; Villeneuve, Pierre; Durand, Erwann; Sørensen, Ann-Dorit Moltke

2017-11-01

Antioxidant effects of ferulic acid and lipophilized ferulate esters were investigated in fish oil-enriched milk. Methyl ferulate (C1) and ethyl ferulate (C2) more efficiently prevented lipid oxidation than dodecyl ferulate (C12) did, followed by ferulic acid (C0). The combination of C1 or C2 with C12 could have a "synergistic" effect indicated by peroxide value, hexanal, and 1-penten-3-ol analysis results. These antioxidants also showed protein oxidation inhibition effects. The most effective antioxidants (C1 and C2) had the highest concentration in the precipitate phase but the lowest concentration in the aqueous phase, which was the opposite of the partitioning of C0. C12 had the highest concentration in the oil and emulsion phase. In particular, the interaction between ferulates esterified with short and medium alkyl chain lengths could lead to their "synergistic" effects in fish oil-enriched milk, which could be caused by the change in their partitioning or localization at the interface.

Diet fat alters synaptosomal phosphatidylethanolaminemethyl-transferase activity and phosphatidylcholine synthesis in brain

DOE Office of Scientific and Technical Information (OSTI.GOV)

Hargreaves, K.M.; Clandinin, M.T.

1986-03-05

Phosphatidylcholine (PC) can be synthesized via three routes, each having potentially different metabolic fates. One route for PC synthesis is methylation of phosphatidylethanolamine (PE). To examine if dietary fat affects membrane PE composition and phosphatidylethanolaminemethyltransferase (PEMT) activity, male weanling rats were fed semi-purified diets containing 20% (w/w) fat of differing fatty acid composition for 24 days. Microsomal and synaptic plasma membranes were isolated and phospholipid composition analyzed. PEMT activity was measured by incorporation of the methyl group from /sup 3/H-S-adenosylmethionine into PE. Polyunsaturated diets high in omega 6 fatty acids produce a high ratio of omega 6/omega 3 fatty acidsmore » in synaptic plasma membranes. Dietary omega 3 and omega 6 fatty acid levels are reflected in membrane phospholipid content of 22:6(3), 20:4(6), 22:4(6) and 22:5(6). Diet-induced increase in these longer chain homologues of omega 6 and omega 3 fatty acids and a high ratio of omega 6/omega 3 fatty acids in PE are both associated with increased PEMT activity. These results suggest that diet-fat induced change in fatty acid composition of membrane PE results in transition in PEMT activity and synthesis of PC in brain, by providing preferred species of PE for methylation.« less

Determination of Odor Release in Hydrocolloid Model Systems Containing Original or Carboxylated Cellulose at Different pH Values Using Static Headspace Gas Chromatographic (SHS-GC) Analysis

PubMed Central

Lee, Sang Mi; Shin, Gil-Ok; Park, Kyung Min; Chang, Pahn-Shick; Kim, Young-Suk

2013-01-01

Static headspace gas chromatographic (SHS-GC) analysis was performed to determine the release of 13 odorants in hydrocolloid model systems containing original or regio-selectively carboxylated cellulose at different pH values. The release of most odor compounds was decreased in the hydrocolloid solutions compared to control, with the amounts of 2-propanol, 3-methyl-1-butanol, and 2,3-butanedione released into the headspace being less than those of any other odor compound in the hydrocolloid model systems. However, there was no considerable difference between original cellulose-containing and carboxylated-cellulose containing systems in the release of most compounds, except for relatively long-chain esters such as ethyl caprylate and ethyl nonanoate. The release from the original and carboxylated cellulose solutions controlled to pH 10 was significantly higher than that from solutions adjusted to pH 4 and 7 in the case of some esters (ethyl acetate, methyl propionate, ethyl propionate, ethyl butyrate, butyl propionate, ethyl caproate) and alcohols (2-propanol, 3-methyl-1-butanol), in particular, ethyl butyrate and 3-methyl-1-butanol. In contrast, the release of 2,3-butanedione from both the original and carboxylated cellulose solutions was increased at pH 4 and 7 compared to that at pH 10 by about 70% and 130%, respectively. Our study demonstrated that the release of some odorants could be changed significantly by addition of both original and carboxylated cellulose in hydrocolloid model systems, but only minor effect was observed in pH of the solution. PMID:23447013

Alternative oil extraction methods from Echium plantagineum L. seeds using advanced techniques and green solvents.

PubMed

Castejón, Natalia; Luna, Pilar; Señoráns, Francisco J

2018-04-01

The edible oil processing industry involves large losses of organic solvent into the atmosphere and long extraction times. In this work, fast and environmentally friendly alternatives for the production of echium oil using green solvents are proposed. Advanced extraction techniques such as Pressurized Liquid Extraction (PLE), Microwave Assisted Extraction (MAE) and Ultrasound Assisted Extraction (UAE) were evaluated to efficiently extract omega-3 rich oil from Echium plantagineum seeds. Extractions were performed with ethyl acetate, ethanol, water and ethanol:water to develop a hexane-free processing method. Optimal PLE conditions with ethanol at 150 °C during 10 min produced a very similar oil yield (31.2%) to Soxhlet using hexane for 8 h (31.3%). UAE optimized method with ethanol at mild conditions (55 °C) produced a high oil yield (29.1%). Consequently, advanced extraction techniques showed good lipid yields and furthermore, the produced echium oil had the same omega-3 fatty acid composition than traditionally extracted oil. Copyright © 2017 Elsevier Ltd. All rights reserved.

21 CFR 74.2705 - FD&C Yellow No. 5.

Code of Federal Regulations, 2014 CFR

2014-04-01

... 21 Food and Drugs 1 2014-04-01 2014-04-01 false FD&C Yellow No. 5. 74.2705 Section 74.2705 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF... ethyl ester, or a salt of this carboxylic acid. The resulting dye is purified and isolated as the sodium...

21 CFR 74.2705 - FD&C Yellow No. 5.

Code of Federal Regulations, 2012 CFR

2012-04-01

... 21 Food and Drugs 1 2012-04-01 2012-04-01 false FD&C Yellow No. 5. 74.2705 Section 74.2705 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF... ethyl ester, or a salt of this carboxylic acid. The resulting dye is purified and isolated as the sodium...

21 CFR 74.2705 - FD&C Yellow No. 5.

Code of Federal Regulations, 2011 CFR

2011-04-01

... 21 Food and Drugs 1 2011-04-01 2011-04-01 false FD&C Yellow No. 5. 74.2705 Section 74.2705 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF... ethyl ester, or a salt of this carboxylic acid. The resulting dye is purified and isolated as the sodium...

21 CFR 74.2705 - FD&C Yellow No. 5.

Code of Federal Regulations, 2013 CFR

2013-04-01

... 21 Food and Drugs 1 2013-04-01 2013-04-01 false FD&C Yellow No. 5. 74.2705 Section 74.2705 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES GENERAL LISTING OF... ethyl ester, or a salt of this carboxylic acid. The resulting dye is purified and isolated as the sodium...

Omega-3 and Omega-6 Fatty Acids Act as Inhibitors of the Matrix Metalloproteinase-2 and Matrix Metalloproteinase-9 Activity.

PubMed

Nicolai, Eleonora; Sinibaldi, Federica; Sannino, Gianpaolo; Laganà, Giuseppina; Basoli, Francesco; Licoccia, Silvia; Cozza, Paola; Santucci, Roberto; Piro, Maria Cristina

2017-08-01

Polyunsaturated fatty acids have been reported to play a protective role in a wide range of diseases characterized by an increased metalloproteinases (MMPs) activity. The recent finding that omega-3 and omega-6 fatty acids exert an anti-inflammatory effect in periodontal diseases has stimulated the present study, designed to determine whether such properties derive from a direct inhibitory action of these compounds on the activity of MMPs. To this issue, we investigated the effect exerted by omega-3 and omega-6 fatty acids on the activity of MMP-2 and MMP-9, two enzymes that actively participate to the destruction of the organic matrix of dentin following demineralization operated by bacteria acids. Data obtained (both in vitro and on ex-vivo teeth) reveal that omega-3 and omega-6 fatty acids inhibit the proteolytic activity of MMP-2 and MMP-9, two enzymes present in dentin. This observation is of interest since it assigns to these compounds a key role as MMPs inhibitors, and stimulates further study to better define their therapeutic potentialities in carious decay.

Qualitative in vitro NMR analysis of creatine ethyl ester pronutrient in human plasma.

PubMed

Giese, M W; Lecher, C S

2009-10-01

There are a number of forms of creatine available that attempt to improve the solubility and permeability, with the anticipation this will result in an improved pharmacokinetic profile and ultimately an enhanced ergogenic response. Previous research has shown that the different salt forms can improve solubility resulting in slightly altered pharmacokinetic profiles, however specific data exploring the conversion of esterified derivatives to creatine is lacking. The purpose of this study was to examine the assertion that creatine ethyl ester undergoes enzymatic conversion to creatine in human tissues. The IN VITRO response of creatine ethyl ester to incubation in human plasma was examined by H-NMR analysis. Lyophilized human plasma was reconstituted in D2O and phosphate-buffered saline and 1.5 mg of the analyte was added. Following incubation at 37 degrees C for 4 h and subsequent protein precipitation, the supernatant was analyzed by NMR, utilizing the diagnostic chemical shift of the methylene signal to determine the species present in solution, I.E. creatine ethyl ester, creatine, or creatinine. Both creatine and creatinine were run in parallel as control experiments and each assay was run in triplicate. As expected both creatine and creatinine remained unchanged. However, conversion of creatine ethyl ester to creatine by the esterases in human plasma was not observed to any detectable extent and the only species detected after the incubation period was creatinine. While not a definitive characterization of the IN VIVO behavior, these results strongly warrant a complete IN VIVO pharmacokinetic analysis of creatine ethyl ester since it appears these "pronutrients" may actually provide large exogenous sources of pharmacologically inactive creatinine rather than ergogenic creatine.

Increase of fruity aroma during mixed T. delbrueckii/S. cerevisiae wine fermentation is linked to specific esters enhancement.

PubMed

Renault, Philippe; Coulon, Joana; de Revel, Gilles; Barbe, Jean-Christophe; Bely, Marina

2015-08-17

The aim of this work was to study ester formation and the aromatic impact of Torulaspora delbrueckii when used in association with Saccharomyces cerevisiae during the alcoholic fermentation of must. In order to evaluate the influence of the inoculation procedure, sequential and simultaneous mixed cultures were carried out and compared to pure cultures of T. delbrueckii and S. cerevisiae. Our results showed that mixed inoculations allowed the increase, in comparison to S. cerevisiae pure culture, of some esters specifically produced by T. delbrueckii and significantly correlated to the maximal T. delbrueckii population reached in mixed cultures. Thus, ethyl propanoate, ethyl isobutanoate and ethyl dihydrocinnamate were considered as activity markers of T. delbrueckii. On the other hand, isobutyl acetate and isoamyl acetate concentrations were systematically increased during mixed inoculations although not correlated with the development of either species but were rather due to positive interactions between these species. Favoring T. delbrueckii development when performing sequential inoculation enhanced the concentration of esters linked to T. delbrueckii activity. On the contrary, simultaneous inoculation restricted the growth of T. delbrueckii, limiting the production of its activity markers, but involved a very important production of numerous esters due to more important positive interactions between species. These results suggest that the ester concentrations enhancement via interactions during mixed modalities was due to S. cerevisiae production in response to the presence of T. delbrueckii. Finally, sensory analyses showed that mixed inoculations between T. delbrueckii and S. cerevisiae allowed to enhance the complexity and fruity notes of wine in comparison to S. cerevisiae pure culture. Furthermore, the higher levels of ethyl propanoate, ethyl isobutanoate, ethyl dihydrocinnamate and isobutyl acetate in mixed wines were found responsible for the increase of fruitiness and complexity. Copyright © 2015 Elsevier B.V. All rights reserved.

[Plasma fatty acids profile and lipids in Tunisian male elite athletes].

PubMed

Omar, Souheil; Sethom, Mohamed M; Feki-Mhiri, Sondes; Hadj-Taeib, Sameh; Ben Ayed, Ikram; Feki, Moncef; Kaabachi, Naziha

2010-05-01

Growing interest is accorded to polyunsaturated fatty acids (PUFAs) omega3, which are considered beneficial for health. to investigate the effect of sports on plasma lipids and fatty acids (FAs), especially omega6 and omega3 PUFAs and the omega6/omega3 ratio. The study included 75 Tunisian male elite athletes, practicing team sport and 70 sedentary healthy men as controls. Plasma FAs profile was analyzed by gas chromatography. Comparison between groups was performed using a univariate GLM analysis, with adjustment on age, body mass and energy intake. Athletes showed lower triglycerides and saturated FAs (27.64% +/- 2.17% vs. 30.41% +/- 4.35%) and increased HDL cholesterol and monounsaturated FAs (21.19% +/- 2 44% vs. 19.12% +/- 3.03%). However, there was no significant difference in total PUFAs, omega6 and omega3 families and omega6/omega3 ratio (10.15% +/- 3.24% vs. 10.20% +/- 3.37%) between athletes and sedentary. Sport favorably modifies the profile of plasma FAs by increasing monounsaturated FAs at the expense of saturated FAs, but has no effect on total PUFAs, and omega6 and omega3 families. A diet rich in omega3 PUFAs would lower the omega6/omega3 ratio, in order to improve the health and probably the performance of athletes.

Effect of dietary selenium and omega-3 fatty acids on muscle composition and quality in broilers

PubMed Central

Haug, Anna; Eich-Greatorex, Susanne; Bernhoft, Aksel; Wold, Jens P; Hetland, Harald; Christophersen, Olav A; Sogn, Trine

2007-01-01

Background Human health may be improved if dietary intakes of selenium and omega-3 fatty acids are increased. Consumption of broiler meat is increasing, and the meat content of selenium and omega-3 fatty acids are affected by the composition of broiler feed. A two-way analyses of variance was used to study the effect of feed containing omega-3 rich plant oils and selenium enriched yeast on broiler meat composition, antioxidation- and sensory parameters. Four different wheat-based dietary treatments supplemented with 5% rapeseed oil or 4% rapeseed oil plus 1% linseed oil, and either 0.50 mg selenium or 0.84 mg selenium (organic form) per kg diet was fed to newly hatched broilers for 22 days. Results The different dietary treatments gave distinct different concentrations of selenium and fatty acids in thigh muscle; one percent linseed oil in the diet increased the concentration of the omega-3 fatty acids 18:3, 20:5 and 22:5, and 0.84 mg selenium per kg diet gave muscle selenium concentration at the same level as is in fish muscle (0.39 mg/kg muscle). The high selenium intake also resulted in increased concentration of the long-chain omega-3 fatty acids EPA (20:5), DPA (22:5) and DHA (22:6), thus it may be speculated if high dietary selenium might have a role in increasing the concentration of EPA, DPA and DHA in tissues after intake of plant oils contning omega-3 fatty acids. Conclusion Moderate modifications of broiler feed may give a healthier broiler meat, having increased content of selenium and omega-3 fatty acids. High intakes of selenium (organic form) may increase the concentration of very long-chain omega-3 fatty acids in muscle. PMID:17967172

Time to Talk: Five Things to Know about Omega-3s for Heart Disease

MedlinePlus

... X Y Z 5 Things To Know About Omega-3s for Heart Disease Share: Omega-3 fatty acids are a group of polyunsaturated fatty ... supplements. While experts agree that fish rich in omega-3 fatty acids should be included in a heart- ...

Comparison of gene expression and fatty acid profiles in concentrate and forage finished beef.

PubMed

Buchanan, J W; Garmyn, A J; Hilton, G G; VanOverbeke, D L; Duan, Q; Beitz, D C; Mateescu, R G

2013-01-01

Fatty acid profiles and intramuscular expression of genes involved in fatty acid metabolism were characterized in concentrate- (CO) and forage- (FO) based finishing systems. Intramuscular samples from the adductor were taken at slaughter from 99 heifers finished on a CO diet and 58 heifers finished on a FO diet. Strip loins were obtained at fabrication to evaluate fatty acid profiles of LM muscle for all 157 heifers by using gas chromatography fatty acid methyl ester analysis. Composition was analyzed for differences by using the General Linear Model (GLM) procedure in SAS. Differences in fatty acid profile included a greater atherogenic index, greater percentage total MUFA, decreased omega-3 to omega-6 ratio, decreased percentage total PUFA, and decreased percentage omega-3 fatty acids in CO- compared with FO-finished heifers (P<0.05). Fatty acid profiles from intramuscular samples were ranked by the atherogenic index, and 20 heifers with either a high (HAI; n=10) or low (LAI; n=10) atherogenic index were selected for gene expression analysis using real-time PCR (RT-PCR). Gene expression data for the 20 individuals were analyzed as a 2 by 2 factorial arrangement of treatments using the GLM procedure in SAS. There was no significant diet × atherogenic index interaction identified for any gene (P>0.05). Upregulation was observed for PPARγ, fatty acid synthase (FASN), and fatty acid binding protein 4 (FABP4) in FO-finished compared with CO-finished heifers in both atherogenic index categories (P<0.05). Upregulation of diglyceride acyl transferase 2 (DGAT2) was observed in FO-finished heifers with a HAI (P<0.05). Expression of steroyl Co-A desaturase (SCD) was upregulated in CO-finished heifers with a LAI, and downregulated in FO-finished heifers with a HAI (P<0.05). Expression of adiponectin (ADIPOQ) was significantly downregulated in CO-finished heifers with a HAI compared with all other categories (P<0.05). The genes identified in this study which exhibit differential regulation in response to diet or in animals with extreme fatty acid profiles may provide genetic markers for selecting desirable fatty acid profiles in future selection programs.

Chronic administration of docosahexaenoic acid or eicosapentaenoic acid, but not arachidonic acid, alone or in combination with uridine, increases brain phosphatide and synaptic protein levels in gerbils.

PubMed

Cansev, M; Wurtman, R J

2007-08-24

Synthesis of phosphatidylcholine, the most abundant brain membrane phosphatide, requires three circulating precursors: choline; a pyrimidine (e.g. uridine); and a polyunsaturated fatty acid. Supplementing a choline-containing diet with the uridine source uridine-5'-monophosphate (UMP) or, especially, with UMP plus the omega-3 fatty acid docosahexaenoic acid (given by gavage), produces substantial increases in membrane phosphatide and synaptic protein levels within gerbil brain. We now compare the effects of various polyunsaturated fatty acids, given alone or with UMP, on these synaptic membrane constituents. Gerbils received, daily for 4 weeks, a diet containing choline chloride with or without UMP and/or, by gavage, an omega-3 (docosahexaenoic or eicosapentaenoic acid) or omega-6 (arachidonic acid) fatty acid. Both of the omega-3 fatty acids elevated major brain phosphatide levels (by 18-28%, and 21-27%) and giving UMP along with them enhanced their effects significantly. Arachidonic acid, given alone or with UMP, was without effect. After UMP plus docosahexaenoic acid treatment, total brain phospholipid levels and those of each individual phosphatide increased significantly in all brain regions examined (cortex, striatum, hippocampus, brain stem, and cerebellum). The increases in brain phosphatides in gerbils receiving an omega-3 (but not omega-6) fatty acid, with or without UMP, were accompanied by parallel elevations in levels of pre- and post-synaptic proteins (syntaxin-3, PSD-95 and synapsin-1) but not in those of a ubiquitous structural protein, beta-tubulin. Hence administering omega-3 polyunsaturated fatty acids can enhance synaptic membrane levels in gerbils, and may do so in patients with neurodegenerative diseases, especially when given with a uridine source, while the omega-6 polyunsaturated fatty acid arachidonic acid is ineffective.

Chronic administration of docosahexaenoic acid or eicosapentaenoic acid, but not arachidonic acid, alone or in combination with uridine, increases brain phosphatide and synaptic protein levels in gerbils

PubMed Central

Cansev, M.; Wurtman, R. J.

2007-01-01

Synthesis of phosphatidylcholine, the most abundant brain membrane phosphatide, requires three circulating precursors: choline; a pyrimidine (e.g., uridine); and a polyunsaturated fatty acid. Supplementing a choline-containing diet with the uridine source uridine-5′-monophosphate (UMP) or, especially, with UMP plus the omega-3 fatty acid docosahexaenoic acid (given by gavage), produces substantial increases in membrane phosphatide and synaptic protein levels within gerbil brain. We now compare the effects of various polyunsaturated fatty acids, given alone or with UMP, on these synaptic membrane constituents. Gerbils received, daily for 4 weeks, a diet containing choline chloride with or without UMP and/or, by gavage, an omega-3 (docosahexaenoic or eicosapentaenoic acid) or omega-6 (arachidonic acid) fatty acid. Both of the omega-3 fatty acids elevated major brain phosphatide levels (by 18-28%, and 21-27%) and giving UMP along with them enhanced their effects significantly. Arachidonic acid, given alone or with UMP, was without effect. After UMP plus docosahexaenoic acid treatment, total brain phospholipids levels and those of each individual phosphatide increased significantly in all brain regions examined (cortex, striatum, hippocampus, brain stem, and cerebellum). The increases in brain phosphatides in gerbils receiving an omega-3 (but not omega-6) fatty acid, with or without UMP, were accompanied by parallel elevations in levels of pre- and post-synaptic proteins (syntaxin-3, PSD-95 and Synapsin-1) but not in those of a ubiquitous structural protein, β-tubulin. Hence administering omega-3 polyunsaturated fatty acids can enhance synaptic membrane levels in gerbils, and may do so in patients with neurodegenerative diseases, especially when given with a uridine source, while the omega-6 polyunsaturated fatty acid arachidonic acid is ineffective. PMID:17683870

Omega-3 polyunsaturated fatty acid and ursodeoxycholic acid have an additive effect in attenuating diet-induced nonalcoholic steatohepatitis in mice

PubMed Central

Kim, Ja Kyung; Lee, Kwan Sik; Lee, Dong Ki; Lee, Su Yeon; Chang, Hye Young; Choi, Junjeong; Lee, Jung Il

2014-01-01

Nonalcoholic steatohepatitis (NASH) can progress into liver cirrhosis; however, no definite treatment is available. Omega-3 polyunsaturated fatty acid (omega-3) has been reported to alleviate experimental NASH, although its beneficial effect was not evident when tested clinically. Thus, this study aimed to investigate the additive effect of omega-3 and ursodeoxycholic acid (UDCA) on diet-induced NASH in mice. C57BL/6 mice were given a high-fat diet (HFD) for 24 weeks, at which point the mice were divided into three groups and fed HFD alone, HFD with omega-3 or HFD with omega-3 in combination with UDCA for another 24 weeks. Feeding mice an HFD and administering omega-3 improved histologically assessed liver fibrosis, and UDCA in combination with omega-3 further attenuated this disease. The assessment of collagen α1(I) expression agreed with the histological evaluation. Omega-3 in combination with UDCA resulted in a significant attenuation of inflammation whereas administering omega-3 alone failed to improve histologically assessed liver inflammation. Quantitative analysis of tumor necrosis factor α showed an additive effect of omega-3 and UDCA on liver inflammation. HFD-induced hepatic triglyceride accumulation was attenuated by omega-3 and adding UDCA accentuated this effect. In accordance with this result, the expression of sterol regulatory binding protein-1c decreased after omega-3 administration and adding UDCA further diminished SREBP-1c expression. The expression of inducible nitric oxide synthase (iNOS), which may reflect oxidative stress-induced tissue damage, was suppressed by omega-3 administration and adding UDCA further attenuated iNOS expression. These results demonstrated an additive effect of omega-3 and UDCA for alleviating fibrosis, inflammation and steatosis in diet-induced NASH. PMID:25523099

Omega-3 polyunsaturated fatty acid and ursodeoxycholic acid have an additive effect in attenuating diet-induced nonalcoholic steatohepatitis in mice.

PubMed

Kim, Ja Kyung; Lee, Kwan Sik; Lee, Dong Ki; Lee, Su Yeon; Chang, Hye Young; Choi, Junjeong; Lee, Jung Il

2014-12-19

Nonalcoholic steatohepatitis (NASH) can progress into liver cirrhosis; however, no definite treatment is available. Omega-3 polyunsaturated fatty acid (omega-3) has been reported to alleviate experimental NASH, although its beneficial effect was not evident when tested clinically. Thus, this study aimed to investigate the additive effect of omega-3 and ursodeoxycholic acid (UDCA) on diet-induced NASH in mice. C57BL/6 mice were given a high-fat diet (HFD) for 24 weeks, at which point the mice were divided into three groups and fed HFD alone, HFD with omega-3 or HFD with omega-3 in combination with UDCA for another 24 weeks. Feeding mice an HFD and administering omega-3 improved histologically assessed liver fibrosis, and UDCA in combination with omega-3 further attenuated this disease. The assessment of collagen α1(I) expression agreed with the histological evaluation. Omega-3 in combination with UDCA resulted in a significant attenuation of inflammation whereas administering omega-3 alone failed to improve histologically assessed liver inflammation. Quantitative analysis of tumor necrosis factor α showed an additive effect of omega-3 and UDCA on liver inflammation. HFD-induced hepatic triglyceride accumulation was attenuated by omega-3 and adding UDCA accentuated this effect. In accordance with this result, the expression of sterol regulatory binding protein-1c decreased after omega-3 administration and adding UDCA further diminished SREBP-1c expression. The expression of inducible nitric oxide synthase (iNOS), which may reflect oxidative stress-induced tissue damage, was suppressed by omega-3 administration and adding UDCA further attenuated iNOS expression. These results demonstrated an additive effect of omega-3 and UDCA for alleviating fibrosis, inflammation and steatosis in diet-induced NASH.

Effects of Diets High in Unsaturated Fatty Acids on Socially Induced Stress Responses in Guinea Pigs

PubMed Central

Nemeth, Matthias; Millesi, Eva; Wagner, Karl-Heinz; Wallner, Bernard

2014-01-01

Unsaturated fatty acids (UFAs), such as omega-3 and omega-6 poly- and omega-9 monounsaturated fatty acids are important nutrients and major components of neuronal cell membranes. They play a major role in modulating brain functions and physiology and may therefore diminish behavioral and physiological stress reactions in corroboration with decreased cortisol concentrations. Functionally, cortisol itself can modulate several behaviors and also the fatty acid metabolism in the long term. But only little is known about the behavioral and physiological influences of dietary UFAs in a social group, where individuals are regularly exposed to stressful situations. Therefore, the aim of this study was to determine the effects of dietary UFAs on saliva cortisol concentrations and behavioral responses in socially confronted guinea pigs. Three groups of animals were additionally supplemented with 500 mg chia seeds (high in omega-3), walnuts (high in omega-6), or peanuts (high in omega-9) per kg bodyweight each day and compared to a control group. During social confrontation saliva cortisol concentrations significantly increased in all groups, which was accompanied by a loss in bodyweight. However, cortisol levels remained lower in the chia and walnut groups compared to controls. Additionally, the walnut group displayed significantly increased locomotion, while no differences between groups were detected in socio-positive, sexual, or aggressive behaviors. Total plasma omega-3, omega-6, and omega-9 fatty acids were significantly increased in the corresponding groups, due to the dietary supplementations. However, a significant decrease in plasma omega-3 and an increase in plasma n-6 fatty acids were detected in the chia group when comparing the measurements before and after social confrontation. We conclude that both omega-3 and omega-6 polyunsaturated fatty acids can diminish behavioral and physiological stress responses to the social environment, enabling individuals to cope with social stressors, but at the expense of plasma derived omega-3 fatty acids. PMID:25551380

Meat-based functional foods for dietary equilibrium omega-6/omega-3.

PubMed

Reglero, Guillermo; Frial, Paloma; Cifuentes, Alejandro; García-Risco, Mónica R; Jaime, Laura; Marin, Francisco R; Palanca, Vicente; Ruiz-Rodríguez, Alejandro; Santoyo, Susana; Señoráns, Francisco J; Soler-Rivas, Cristina; Torres, Carlos; Ibañez, Elena

2008-10-01

Nutritionists encourage improving the diet by combining meat products with fish or other sea-related foods, in order to equilibrate the omega-6/omega-3 ratio. Strong scientific evidence supports the beneficial health effects of a balanced omega-6/omega-3 PUFA (poly unsaturated fatty acids) diets. In the present work, the scientific bases of new functional meat products with both a balanced omega-6/omega-3 ratio and a synergic combination of antioxidants are discussed. The aim is to contribute to the dietary equilibrium omega-6/omega-3 and to increase the antioxidant intake. Conventional meat products supplemented with a specific fatty acids and antioxidants combination led to functional foods with healthier nutritional parameters.

Designing of a fluoride selective receptor through molecular orbital engineering

NASA Astrophysics Data System (ADS)

Mishra, Rakesh K.; Kumar, Virendra; Diwan, Uzra; Upadhyay, K. K.; Roy Chowdhury, P. K.

2012-11-01

The stepwise substitution of appropriate groups over the 3-[(2,4-dinitro-phenyl)-hydrazono]-butyric acid ethyl ester (R3) lead receptor R1 which showed selectivity towards fluoride in DMSO. The UV-vis and 1H NMR titration studies revealed the details of the binding between receptor R1 and fluoride. The receptor R1 also recognized fluoride in a toothpaste solution to as low as 50 ppm. The theoretical simulations of recognition event at Density Functional Theory (DFT) level using B3LYP/6-31G** basis set and polarizable continuum model (PCM) approach lead a semi-quantitative match with the experimental results.

Omega-3 fatty acids in health and disease and in growth and development.

PubMed

Simopoulos, A P

1991-09-01

Several sources of information suggest that man evolved on a diet with a ratio of omega 6 to omega 3 fatty acids of approximately 1 whereas today this ratio is approximately 10:1 to 20-25:1, indicating that Western diets are deficient in omega 3 fatty acids compared with the diet on which humans evolved and their genetic patterns were established. Omega-3 fatty acids increase bleeding time; decrease platelet aggregation, blood viscosity, and fibrinogen; and increase erythrocyte deformability, thus decreasing the tendency to thrombus formation. In no clinical trial, including coronary artery graft surgery, has there been any evidence of increased blood loss due to ingestion of omega 3 fatty acids. Many studies show that the effects of omega 3 fatty acids on serum lipids depend on the type of patient and whether the amount of saturated fatty acids in the diet is held constant. In patients with hyperlipidemia, omega 3 fatty acids decrease low-density-lipoprotein (LDL) cholesterol if the saturated fatty acid content is decreased, otherwise there is a slight increase, but at high doses (32 g) they lower LDL cholesterol; furthermore, they consistently lower serum triglycerides in normal subjects and in patients with hypertriglyceridemia whereas the effect on high-density lipoprotein (HDL) varies from no effect to slight increases. The discrepancies between animal and human studies most likely are due to differences between animal and human metabolism. In clinical trials eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in the form of fish oils along with antirheumatic drugs improve joint pain in patients with rheumatoid arthritis; have a beneficial effect in patients with ulcerative colitis; and in combination with drugs, improve the skin lesions, lower the hyperlipidemia from etretinates, and decrease the toxicity of cyclosporin in patients with psoriasis. In various animal models omega 3 fatty acids decrease the number and size of tumors and increase the time elapsed before appearance of tumors. Studies with nonhuman primates and human newborns indicate that DHA is essential for the normal functional development of the retina and brain, particularly in premature infants. Because omega 3 fatty acids are essential in growth and development throughout the life cycle, they should be included in the diets of all humans. Omega-3 and omega 6 fatty acids are not interconvertible in the human body and are important components of practically all cell membranes. Whereas cellular proteins are genetically determined, the polyunsaturated fatty acid (PUFA) composition of cell membranes is to a great extent dependent on the dietary intake.(ABSTRACT TRUNCATED AT 400 WORDS)

Dietary sources of omega 3 fatty acids: public health risks and benefits.

PubMed

Tur, J A; Bibiloni, M M; Sureda, A; Pons, A

2012-06-01

Omega 3 fatty acids can be obtained from several sources, and should be added to the daily diet to enjoy a good health and to prevent many diseases. Worldwide, general population use omega-3 fatty acid supplements and enriched foods to get and maintain adequate amounts of these fatty acids. The aim of this paper was to review main scientific evidence regarding the public health risks and benefits of the dietary sources of omega-3 fatty acids. A systematic literature search was performed, and one hundred and forty-five articles were included in the results for their methodological quality. The literature described benefits and risks of algal, fish oil, plant, enriched dairy products, animal-derived food, krill oil, and seal oil omega-3 fatty acids.

Comparative study on the radiolytic degradation of 4-hydroxybenzoate and 4-hydroxybenzoic ethyl ester

NASA Astrophysics Data System (ADS)

Swoboda, F.; Solar, S.

1999-09-01

The radiolytic degradation of 4-hydroxybenzoic acid ethyl ester (4-HBAEE) and 4-hydroxybenzoate (4-HBA) and the subsequent product formation in N 2O-saturated and aerated solutions has been studied as a function of dose. The rate constants of OH • radicals with the substrates are k(OH •+4-HBAEE)=7.5×10 9 dm 3 mol -1 s -1 and k(OH • +4-HBA)=6.7×10 9 dm 3 mol -1 s -1. Irradiation of 5×10 -4 mol dm -3 aqueous solutions (N 2O, pH 6.0) of 4-HBA leads to the products 3,4-dihydroxybenzoic acid (3,4-DHBA) and hydroquinone (HQ). In the case of 4-HBAEE neither hydroxylation nor decarboxylation products are observable. The predominating reaction pathway with 4-HBAEE is water elimination from the primarily formed dihydroxycyclohexadienyl radicals. By pulse radiolysis a protonation equilibrium of these transients with pK=8.0 could be determined. The protonated OH •-adducts (λ max=385 nm, ɛ=300 m 2 mol -1) decay with k=7×10 4 s -1, the radical anions (λ max=425 nm, ɛ=240 m 2 mol -1) with k=4×10 5 s -1, yielding phenoxyl radicals λ max 405 nm, ɛ=160 m 2 mol -1 and 425 nm, ɛ=175 m 2 mol -1, 2 k=3.6×10 8 dm 3 mol -1 s -1, which do not form phenolic compounds. With 4-HBA OH •-adducts water splitting at pH 6 is very slow, k=4×10 3 s -1, therefore second order decay reactions can compete. At pH 10, where base catalysed water elimination takes place, no hydroxylation products are observable either. In aerated solutions dihydroxy-compounds are formed with both substrates, due to the fast addition of oxygen to the OH •-adducts. In the case of 4-HBA 68% of the OH • radicals result in 3,4-dihydroxyderivatives; for 4-HBAEE these are only 25%. The decarboxylation product hydroquinone is generated only from 4-HBA, its yield corresponds to 18% of the OH • radicals. Comparison of the initial degradation yields demonstrates 4-HBAEE to be 1.6 times more stable towards radiation, for a 50% decomposition of the ester a 2.3 times higher dose as for 4-HBA is required. The low rate of hydroxylation, the lack of decarboxylation products and the remarkable resistance to radiation of the ester of 4-hydroxybenzoic acid is of importance in respect to chemical changes in irradiated fruits and vegetables.

Omega-3 supplementation during the first 5 years of life and later academic performance: a randomised controlled trial.

PubMed

Brew, B K; Toelle, B G; Webb, K L; Almqvist, C; Marks, G B

2015-04-01

Consumption of oily fish more than once per week has been shown to improve cognitive outcomes in children. However, it is unknown whether similar benefits can be achieved by long-term omega-3 fatty acid supplementation. The objective was to investigate the effect of omega-3 fatty acid supplementation during the first 5 years of life on subsequent academic performance in children by conducting a secondary analysis of the CAPS (Childhood Asthma Prevention Study). A total of 616 infants with a family history of asthma were randomised to receive tuna fish oil (high in long-chain omega-3 fatty acids, active) or Sunola oil (low in omega-3 fatty acids, control) from the time breastfeeding ceased or at the age of 6 months until the age of 5 years. Academic performance was measured by a nationally standardised assessment of literacy and numeracy (National Assessment Program Literacy and Numeracy (NAPLAN)) in school years 3, 5, 7 and 9. Plasma omega-3 fatty acid levels were measured at regular intervals until 8 years of age. Between-group differences in test scores, adjusted for maternal age, birth weight and maternal education, were estimated using mixed-model regression. Among 239 children, there were no significant differences in NAPLAN scores between active and control groups. However, at 8 years, the proportion of omega-3 fatty acid in plasma was positively associated with the NAPLAN score (0.13 s.d. unit increase in score per 1% absolute increase in plasma omega-3 fatty acid (95% CI 0.03, 0.23)). Our findings do not support the practice of supplementing omega-3 fatty acids in the diet of young children to improve academic outcomes. Further exploration is needed to understand the association between plasma omega-3 fatty acid levels at 8 years and academic performance.

The Role of Omega-3 Fatty Acids in Diets.

PubMed

Gomez-Candela, C; Roldan Puchalt, M C; Palma Milla, S; Lopez Plaza, B; Bermejo, L

2015-01-01

The article is a summary of Dra. Carmen Gómez Candela's presentation at the Science in Nutrition 3rd International Congress in Milan, March 2014. The article covers omega-3 fatty acids use in different medical areas and several institutions' opinions in relation to the topic. Omega-3 acids are essential fatty acids. A certain amount of omega-3 is needed in our daily diet; however, the usual consumption is generally less than the recommended amount. Changes in dietary patterns in the course of history have led to deficit levels of omega-3 in the human body. Currently, there is increasing evidence of the benefits of omega-3 in different medical specialities. There are still some gaps regarding its role in illnesses such as dementia, psychiatric disorders, and inflammatory diseases. Nevertheless, stronger evidence is being proved in cardiovascular diseases and cancer. This article provides a reflection on possible ways to increase omega-3 daily consumption and the constraints associated with food with high contents of heavy metals, which, in turn, are also rich in omega-3s.

Encapsulation of vegetable oils as source of omega-3 fatty acids for enriched functional foods.

PubMed

Ruiz Ruiz, Jorge Carlos; Ortiz Vazquez, Elizabeth De La Luz; Segura Campos, Maira Rubi

2017-05-03

Polyunsaturated omega-3 fatty acids (PUFAs), a functional component present in vegetable oils, are generally recognized as being beneficial to health. Omega-3 PUFAs are rich in double bonds and unsaturated in nature; this attribute makes them highly susceptible to lipid oxidation and unfit for incorporation into long shelf life foods. The microencapsulation of oils in a polymeric matrix (mainly polysaccharides) offers the possibility of controlled release of the lipophilic functional ingredient and can be useful for the supplementation of foods with PUFAs. The present paper provides a literature review of different vegetable sources of omega-3 fatty acids, the functional effects of omega-3 fatty acids, different microencapsulation methods that can possibly be used for the encapsulation of oils, the properties of vegetable oil microcapsules, the effect of encapsulation on oxidation stability and fatty acid composition of vegetable oils, and the incorporation of long-chain omega-3 polyunsaturated fatty acids in foods.

Metabolism of benoxinate in humans.

PubMed

Kasuya, F; Igarashi, K; Fukui, M

1987-04-01

The metabolism of benoxinate hydrochloride [2-(diethylamino)ethyl 4-amino-3-butoxybenzoate monohydrochloride; oxybuprocaine] was examined in humans after administration of a single oral dose. The drug was almost completely absorbed and was rapidly excreted in the urine (92.1% of dose in 9 h). Nine metabolites and unchanged drug were isolated from the urine and identified by comparison of TLC, GC, and GC-MS with authentic compounds. Any metabolites reflecting initial loss of the butyl side chain of benoxinate could not be detected. This suggests that the ester portion is metabolized more rapidly than the O-butyl side chain. 3-Butoxy-4-aminobenzoic acid, the hydrolyzed product of benoxinate, was primarily excreted (70-90% of dose) as the glucuronide together with a trace of the glycine conjugate (0.35% of dose). In addition, 3-butoxy-4-acetylaminobenzoic acid, 3-hydroxy-4-aminobenzoic acid, and 3-hydroxy-4-acetylaminobenzoic acid were identified, the latter two being detected partly as the glucuronides (1.20 and 1.43% of dose, respectively).

Effect of antioxidant protection of must on volatile compounds and aroma shelf life of Falanghina (Vitis vinifera L.) wine.

PubMed

Moio, Luigi; Ugliano, Maurizio; Genovese, Alessandro; Gambuti, Angelita; Pessina, Rita; Piombino, Paola

2004-02-25

Two vinification methods involving different degrees of antioxidant protection of Falanghina must during prefermentative steps, and referred as HAMP (high antioxidant must protection) and LAMP (low antioxidant must protection), were compared in terms of fermentation performances of four different yeast strains, composition of the volatile fraction of wines at the end of alcoholic fermentation, and shelf life of wines during storage. The use of HAMP technology resulted in wines with lower volatile acidity and higher concentrations of medium-chain fatty acid ethyl esters, acetates, and volatile fatty acids. For two of the four strains a lower concentration of isoamyl alcohol was also observed. HAMP wines also revealed increased shelf life because of the higher concentration of odor active esters at the end of storage and better preservation of varietal aromas.

Tissue Fatty Acid Profile is Differently Modulated from Olive Oil and Omega-3 Polyunsaturated Fatty Acids in ApcMin/+ Mice.

PubMed

Tutino, Valeria; Caruso, Maria G; De Leonardis, Giampiero; De Nunzio, Valentina; Notarnicola, Maria

2017-11-16

Fatty acid profile can be considered an appropriate biomarker for investigating the relations between the patterns of fatty acid metabolism and specific diseases, as cancer, cardiovascular and degenerative diseases. Aim of this study was to test the effects of diets enriched with olive oil and omega-3 Polyunsaturated Fatty Acids (PUFAs) on fatty acid profile in intestinal tissue of ApcMin/+ mice. Three groups of animals were considered: control group, receiving a standard diet; olive oilgroup, receiving a standard diet enriched with olive oil; omega-3 group, receiving a standard diet enriched with salmon fish. Tissue fatty acid profile was evaluated by gas chromatography method. Olive oil and omega-3 PUFAs in the diet differently affect the tissue fatty acid profile. Compared to control group, the levels of Saturated Fatty Acids (SFAs) were lower in olive oil group, while an increase of SFAs was found in omega-3 group. Monounsaturated Fatty Acids (MUFAs) levels were enhanced after olive oil treatment, and in particular, a significant increase of oleic acid levels was detected; MUFAs levels were instead reduced in omega-3 group in line with the decrease of oleic acid levels. The total PUFAs levels were lower in olive oil respect to control group. Moreover, a significant induction of Saturation Index (SI) levels was observed after omega-3 PUFAs treatment, while its levels were reduced in mice fed with olive oil. Our data demonstrated a different effect of olive oil and omega-3 PUFAs on tissue lipid profile in APCMin/+ mice. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Supplementation with Omega-3 Fatty Acids in Psychiatric Disorders: A Review of Literature Data

PubMed Central

Bozzatello, Paola; Brignolo, Elena; De Grandi, Elisa; Bellino, Silvio

2016-01-01

A new application for omega-3 fatty acids has recently emerged, concerning the treatment of several mental disorders. This indication is supported by data of neurobiological research, as highly unsaturated fatty acids (HUFAs) are highly concentrated in neural phospholipids and are important components of the neuronal cell membrane. They modulate the mechanisms of brain cell signaling, including the dopaminergic and serotonergic pathways. The aim of this review is to provide a complete and updated account of the empirical evidence of the efficacy and safety that are currently available for omega-3 fatty acids in the treatment of psychiatric disorders. The main evidence for the effectiveness of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) has been obtained in mood disorders, in particular in the treatment of depressive symptoms in unipolar and bipolar depression. There is some evidence to support the use of omega-3 fatty acids in the treatment of conditions characterized by a high level of impulsivity and aggression and borderline personality disorders. In patients with attention deficit hyperactivity disorder, small-to-modest effects of omega-3 HUFAs have been found. The most promising results have been reported by studies using high doses of EPA or the association of omega-3 and omega-6 fatty acids. In schizophrenia, current data are not conclusive and do not allow us either to refuse or support the indication of omega-3 fatty acids. For the remaining psychiatric disturbances, including autism spectrum disorders, anxiety disorders, obsessive-compulsive disorder, eating disorders and substance use disorder, the data are too scarce to draw any conclusion. Concerning tolerability, several studies concluded that omega-3 can be considered safe and well tolerated at doses up to 5 g/day. PMID:27472373

Selective reduction of excitatory hippocampal sharp waves by docosahexaenoic acid and its methyl ester analog ex-vivo.

PubMed

Taha, Ameer Y; Zahid, Tariq; Epps, Tina; Trepanier, Marc-Olivier; Burnham, W M; Bazinet, Richard P; Zhang, Liang

2013-11-06

Excitatory sharp waves (SPWs) originating from the hippocampus are considered to model the interictal "spikes" that occur in people with temporal lobe epilepsy. Docosahexaenoic acid (DHA) is an omega-3 polyunsaturated fatty acid that has been reported to reduce neuronal excitability in vitro. The effect of DHA on hippocampal SPWs, however, is not known. Our goal was to determine whether DHA suppresses SPWs in thick mouse hippocampal slices, and to compare its effects with those of oleic acid (OA, control) and the standard anticonvulsant carbamazepine (CBZ). Also tested, were DHA's structural PUFA analogs n-3 docosapentaenoic acid (n-3 DPA), n-6 docosapentaenoic acid (n-6 DPA) and DHA-methyl ester (DHA-Me). The possible involvement of GABAergic activity was also examined using GABA receptor blockers. Extracellular recordings from CA1 and CA3 regions in hippocampal slices revealed that DHA reduced the incidence of SPWs. CBZ also reduced the incidence of SPWs and was 5 time more potent than DHA. DHA's effects on SPWs was abolished in the presence of GABA-receptor blockers, suggesting involvement of the GABA system in reducing excitatory SPWs. (14)C-DHA application to the slices confirmed the incorporation of DHA into membrane phospholipids. N-3 DPA and n-6 DPA, however, which also incorporate into phospholipids, had no effect on SPWs, while DHA-Me, a DHA analog that does not incorporate into membrane phospholipids, was effective at reducing them. We conclude that DHA, but not its n-3 and n-6 analogs, reduces network excitability of the recurrent CA3 circuitry in the mouse hippocampus. This reduction may be mediated by DHA in its unesterified form, and is likely related to a modulatory effect of DHA on GABAergic activity. © 2013 Published by Elsevier B.V.

Omega-3/Omega-6 Fatty Acids for Attention Deficit Hyperactivity Disorder: A Randomized Placebo-Controlled Trial in Children and Adolescents

ERIC Educational Resources Information Center

Johnson, Mats; Ostlund, Sven; Fransson, Gunnar; Kadesjo, Bjorn; Gillberg, Christopher

2009-01-01

Objective: The aim of the study was to assess omega 3/6 fatty acids (eye q) in attention deficit hyperactivity disorder (ADHD). Method: The study included a randomized, 3-month, omega 3/6 placebo-controlled, one-way crossover trial with 75 children and adolescents (8-18 years), followed by 3 months with omega 3/6 for all. Investigator-rated ADHD…

A new precursor for the preparation of 6-[18F]-fluoro-L-m-tyrosine (FMT): Efficient synthesis and comparison of radiolabeling

DOE Office of Scientific and Technical Information (OSTI.GOV)

VanBrocklin, Henry F.; Blagoev, Milan; Hoepping, Alexander

For the electrophilic preparation of 6-[18F]-Fluoro-L-m-tyrosine (FMT), a PET tracer for measuring changes in dopaminergic function in movement disorders, a novel precursor, N-(tert-butoxycarbonyl)-3-(tert-butoxycarbonyloxy)-6-trimethylstannnyl-L-phenylalanine ethyl ester, was synthesized in four steps and 26 percent yield starting from L-m-tyrosine. FMT produced by two methods at two institutions was comparable in decay corrected yield, 25-26 percent, and quality (chemical, enantiomeric, and radiochemical purity and specific activity) as that obtained with the original N-trifluoroacetyl-3-acetyl-6-trimethylstannyl-L-m-tyrosine ethyl ester FMT precursor.

Fishy Business: Effect of Omega-3 Fatty Acids on Zinc Transporters and Free Zinc Availability in Human Neuronal Cells

PubMed Central

De Mel, Damitha; Suphioglu, Cenk

2014-01-01

Omega-3 (ω-3) fatty acids are one of the two main families of long chain polyunsaturated fatty acids (PUFA). The main omega-3 fatty acids in the mammalian body are α-linolenic acid (ALA), docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). Central nervous tissues of vertebrates are characterized by a high concentration of omega-3 fatty acids. Moreover, in the human brain, DHA is considered as the main structural omega-3 fatty acid, which comprises about 40% of the PUFAs in total. DHA deficiency may be the cause of many disorders such as depression, inability to concentrate, excessive mood swings, anxiety, cardiovascular disease, type 2 diabetes, dry skin and so on. On the other hand, zinc is the most abundant trace metal in the human brain. There are many scientific studies linking zinc, especially excess amounts of free zinc, to cellular death. Neurodegenerative diseases, such as Alzheimer’s disease, are characterized by altered zinc metabolism. Both animal model studies and human cell culture studies have shown a possible link between omega-3 fatty acids, zinc transporter levels and free zinc availability at cellular levels. Many other studies have also suggested a possible omega-3 and zinc effect on neurodegeneration and cellular death. Therefore, in this review, we will examine the effect of omega-3 fatty acids on zinc transporters and the importance of free zinc for human neuronal cells. Moreover, we will evaluate the collective understanding of mechanism(s) for the interaction of these elements in neuronal research and their significance for the diagnosis and treatment of neurodegeneration. PMID:25195602

Influence of omega-3 fatty acids from the flaxseed (Linum usitatissimum) on the brain development of newborn rats.

PubMed

Lenzi Almeida, K C; Teles Boaventura, G; Guzmán Silva, M A

2011-01-01

The importance of essential fatty acids, in particular the omega-3 family, in the central nervous system development of newborns is well documented. The flaxseed (Linum usitatissimum) is considered one of the best vegetable sources of omega-3 fatty acids. The influence of omega-3 fatty acids from flaxseed on the brain development of newborn rats was evaluated. Pups of the F1 generation were obtained from 18 female Wistar rats divided in 3 groups (n=6), FG: fed with diet based on Flaxseed added with casein, CG: Casein, and MCG: Modified Casein supplemented with fibers and soybean oil. Newborn pups were weighted and submitted to euthanasia; brains were collected for evaluation of weight and lipid profile through gaseous chromatography. Significant increase in brain weight (39%) and relative brain weight (37%) was verified in pups from mothers fed with flaxseed diet. The omega-3 (n-3) fatty acids from the flaxseed were found in abundance in the diet made with this oleaginous and also significant increase in docosahexaenoic acid (DHA) (38%), as well as in total of omega-3 (n-3) fatty acids (62%). Maternal diet of flaxseed during pregnancy influences the incorporation of omega-3 fatty acid in the composition of brain tissue, assuring a good development of this organ in newborn rats.

Proper balance of omega-3 and omega-6 fatty acid supplements with topical cyclosporine attenuated contact lens-related dry eye syndrome.

PubMed

Wang, Ling; Chen, Xi; Hao, Jingfang; Yang, Lu

2016-12-01

Essential fatty acids had been applied in the treatment of dry eye syndrome (DES), but the effects of different combinations of fatty acids have not been investigated. 360 long-term contact lens wearers were included in this double-blinded study. Omega-3 and omega-6 fatty acids were combined in different ratios and supplied to the participants that were randomly divided into six groups, and the effects of different essential fatty acids mixture on DES with or without topical cyclosporine were investigated. More than half of long-term contact lens wearers suffered from DES, which were found to be attenuated by oral supplement of properly balanced O3FA and O6FA fatty acid. The topical cyclosporine treatment considerably inhibited the production of cytokines compared to the cyclosporine negative groups, which further relieved DES. Proper balance of omega-3 and omega-6 fatty acid combination significantly alleviated contact lens-related DES.

Omega-3 fatty acids prevent early-life antibiotic exposure-induced gut microbiota dysbiosis and later-life obesity.

PubMed

Kaliannan, K; Wang, B; Li, X-Y; Bhan, A K; Kang, J X

2016-06-01

Early-life antibiotic exposure can disrupt the founding intestinal microbial community and lead to obesity later in life. Recent studies show that omega-3 fatty acids can reduce body weight gain and chronic inflammation through modulation of the gut microbiota. We hypothesize that increased tissue levels of omega-3 fatty acids may prevent antibiotic-induced alteration of gut microbiota and obesity later in life. Here, we utilize the fat-1 transgenic mouse model, which can endogenously produce omega-3 fatty acids and thereby eliminates confounding factors of diet, to show that elevated tissue levels of omega-3 fatty acids significantly reduce body weight gain and the severity of insulin resistance, fatty liver and dyslipidemia resulting from early-life exposure to azithromycin. These effects were associated with a reversal of antibiotic-induced dysbiosis of gut microbiota in fat-1 mice. These results demonstrate the beneficial effects of omega-3 fatty acids on antibiotic-induced gut dysbiosis and obesity, and suggest the potential utility of omega-3 supplementation as a safe and effective means for the prevention of obesity in children who are exposed to antibiotics.

Effects of omega-3 fatty acid plus alpha-tocopherol supplementation on malnutrition-inflammation score, biomarkers of inflammation and oxidative stress in chronic hemodialysis patients.

PubMed

Asemi, Zatollah; Soleimani, Alireza; Shakeri, Hossein; Mazroii, Navid; Esmaillzadeh, Ahmad

2016-11-01

The current study was carried out to assess the effects of omega-3 fatty acid and alpha-tocopherol co-supplementation on malnutrition-inflammation score (MIS), biomarkers of inflammation and oxidative stress in chronic hemodialysis (HD) patients. In a randomized double-blind placebo-controlled clinical trial, 120 patients with chronic HD were included. Patients were randomly allocated into four groups to receive: (1) 1250 mg/day omega-3 fatty acid containing 600 mg EPA and 300 mg DHA + alpha-tocopherol placebo (n = 30); (2) 400 IU/day alpha-tocopherol + omega-3 fatty acids placebo (n = 30); (3) 1250 mg omega-3 fatty acids/day + 400 IU/day alpha-tocopherol (n = 30); and (4) omega-3 fatty acids placebo + alpha-tocopherol placebo (n = 30) for 12 weeks. After 12 weeks of intervention, all three groups of alpha-tocopherol only, individual omega-3 fatty acids, and combined omega-3 fatty acids and alpha-tocopherol experienced a significant improvements in MIS compared with the placebo group; however, improvements were much greater in the individual omega-3 fats (-1.4 ± 1.4) and combined omega-3 fats and alpha-tocopherol (-1.1 ± 2.3) groups compared with alpha-tocopherol group alone (-0.5 ± 1.7, P = 0.004). Furthermore, both individual and combined intervention with omega-3 fats and alpha-tocopherol led to a significant increase in plasma nitric oxide (NO) (combined group: +17.6 ± 29.3; alpha-tocopherol: +43.1 ± 36.3; omega-3 fats: +31.0 ± 40.0; and placebo: -0.5 ± 18.5 µmol/L, respectively, P < 0.001) and total antioxidant capacity (TAC) (+64.9 ± 113.6, +53.0 ± 144.6, +57.6 ± 157.8 and -69.9 ± 215.1 mmol/L, respectively, P = 0.004) levels. Overall, omega-3 fatty acids and alpha-tocopherol co-supplementation for 12 weeks among HD patients improved MIS, plasma NO and TAC levels. Future studies with longer duration of the intervention are needed to confirm the validity of our findings. CLINICAL REGISTRATION: www.irct.ir as IRCT201410245623N28.

Omega-6/omega-3 fatty acid intake of children and older adults in the U.S.: dietary intake in comparison to current dietary recommendations and the Healthy Eating Index.

PubMed

Sheppard, Kelly W; Cheatham, Carol L

2018-03-09

Omega-6 and omega-3 fatty acids (FAs) and their ratio have been shown to affect cognitive function in children and older adults. With these analyses, we aimed to describe omega-6 and omega-3 FA intake among children and older adults in light of FA intake recommendations and with consideration of overall diet. Data were merged from two cross-sectional studies with 219 children 7 to 12 years old and one longitudinal study with 133 adults 65 to 79 years old. Demographic data, anthropometric data, and Healthy Eating Index scores were used to study relations among the omega-6 to omega-3 FA ratio and age, education, body mass index, and diet quality. FA intake, demographic, and anthropometric data were examined using partial correlations, t-tests, and analysis of variance. Most children and adults consumed at least the recommended amount of alpha-linolenic acid (LNA; omega-3) for their age and gender without consuming high amounts of linoleic acid (LA; omega-6), but did not consume sufficient eicosapentaenoic acid (EPA; omega-) and docosahexaenoic acid (DHA; omega-3). The average omega-6 to omega-3 ratios in both groups were lower than previously reported. Eating lower ratios was associated with healthier diets and consuming adequate amounts of several other nutrients. No demographic or anthropometric variables were related to FA intake in children. Adults with a college degree had significantly lower ratios than those without a college degree. American children and older adults are able to consume more balanced omega-6 to omega-3 ratios than has been indicated by commodity data. However, very few American children met even the lowest recommendations for EPA and DHA intake. Research is needed to clarify recommendations for the optimal ratio across development, which may aid in increasing EPA and DHA intake and improving health outcomes in the United States. ClinicalTrials.gov NCT02199808 13 July 2014, NCT01823419 (retrospectively registered) 20 March 2013, and NCT01515098 18 January 2012.

Beneficial effects of omega-3 fatty acids and vitamin B12 supplementation on brain docosahexaenoic acid, brain derived neurotrophic factor, and cognitive performance in the second-generation Wistar rats.

PubMed

Rathod, Richa S; Khaire, Amrita A; Kale, Anvita A; Joshi, Sadhana R

2015-01-01

In vegetarian population, vitamin B12 deficiency coexists with suboptimal levels of omega-3 fatty acids. Studies indicate a need for supplementation/fortification of vitamin B12 and omega-3 fatty acids to reduce the risk of brain disorders. We have described the effects of vitamin B12 and omega-3 fatty acid supplementation on brain development in F1 generation animals. The current study investigates the effects of vitamin B12 and omega-3 fatty acids supplementation on brain function and cognition. Pregnant Wistar rats were assigned the following groups: control, vitamin B12 deficient (BD), vitamin B12 deficient + omega-3 fatty acid (BDO), vitamin B12 supplemented (BS), vitamin B12 supplemented + omega-3 fatty acid (BSO). The same diets were continued for two generations. BDO group showed higher (P < 0.05) levels of BDNF (brain derived neurotrophic factor) and DHA (docosahexaenoic acid) in the cortex and hippocampus as compared with the BD group. The cognitive performance was also normalized in this group. BS showed comparable levels of DHA, BDNF (protein and mRNA), and CREB mRNA (cAMP response element-binding protein) to that of control group while Tropomyosin receptor kinase mRNA levels were higher. The combined vitamin B12 and omega-3 fatty acid supplementation further enhanced the levels of DHA (P < 0.05) and BDNF (P < 0.05) in the hippocampus and CREB mRNA (P < 0.01) in the cortex as compared with BS group. The cognitive performance of these animals was higher (P < 0.05) as compared with BS group. Our data indicates the beneficial effects of vitamin B12 and omega-3 fatty acid supplementation across two generations on brain development and function. © 2015 International Union of Biochemistry and Molecular Biology.

Synthetic Polymers as Gasoline Thickening Agents

DTIC Science & Technology

1944-10-02

Polyvinyl Ethers —---- 71 2. Vistanex and Synthetic Rubbers — 73 3. Ethyl Cellulose 7* a. Solubility Studies 75 b. Gel Preparation — 75 c...Surveillance Tests —- 77 d. Static Firing Tests 78 e. Ethyl Cellulose as a Methacrylate Extender 78 f. Modification of Ethyl Cellulose 78 4...Miscellaneous Polymers 79 5. Emulsions 81 6. Pactices 81 B. Preparation of Polymers not nov in Commercial Production— ---——--— 81 1. Cellulose Esters

Omega-3 Index of Canadian adults.

PubMed

Langlois, Kellie; Ratnayake, Walisundera M N

2015-11-01

Cardioprotective properties have been associated with two fatty acids-eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). The Omega-3 Index indicates the percentage of EPA+DHA in red blood cell fatty acids. Omega-3 Index levels of the Canadian population have not been directly measured. Data for respondents aged 20 to 79 from cycle 3 (2012/2013) of the Canadian Health Measures Survey were used to calculate means and the prevalence of Omega-3 Index coronary heart disease (CHD) risk cut-offs-high (4% or less), moderate (more than 4% to less than 8%), and low (8% or more)-by sociodemographic and lifestyle characteristics, including fish consumption and use of omega-3 supplements. Associations between the Omega-3 Index and CHD-related factors including biomarkers, risk factors, and previous CHD events, were examined in multivariate regression models. The mean Omega-3 Index level of Canadians aged 20 to 79 was 4.5%. Levels were higher for women, older adults, Asians and other non-white Canadians, omega-3 supplement users, and fish consumers; levels were lower for smokers and people who were obese. Fewer than 3% of adults had levels associated with low CHD risk; 43% had levels associated with high risk. No CHD-related factor was associated with the Omega-3 Index when control variables were taken into account. Omega-3 Index levels among Canadian adults were strongly related to age, race, supplement use, fish consumption, smoking status and obesity. Fewer than 3% of adults had Omega-3 Index levels associated with low risk for CHD.

A novel omega3-fatty acid desaturase involved in the biosynthesis of eicosapentaenoic acid.

PubMed Central

Pereira, Suzette L; Huang, Yung-Sheng; Bobik, Emil G; Kinney, Anthony J; Stecca, Kevin L; Packer, Jeremy C L; Mukerji, Pradip

2004-01-01

Long-chain n-3 PUFAs (polyunsaturated fatty acids) such as EPA (eicosapentaenoic acid; 20:5 n-3) have important therapeutic and nutritional benefits in humans. In plants, cyanobacteria and nematodes, omega3-desaturases catalyse the formation of these n-3 fatty acids from n-6 fatty acid precursors. Here we describe the isolation and characterization of a gene ( sdd17 ) derived from an EPA-rich fungus, Saprolegnia diclina, that encodes a novel omega3-desaturase. This gene was isolated by PCR amplification of an S. diclina cDNA library using oligonucleotide primers corresponding to conserved regions of known omega3-desaturases. Expression of this gene in Saccharomyces cerevisiae, in the presence of various fatty acid substrates, revealed that the recombinant protein could exclusively desaturate 20-carbon n-6 fatty acid substrates with a distinct preference for ARA (arachidonic acid; 20:4 n-6), converting it into EPA. This activity differs from that of the known omega3-desaturases from any organism. Plant and cyanobacterial omega3-desaturases exclusively desaturate 18-carbon n-6 PUFAs, and a Caenorhabditis elegans omega3-desaturase preferentially desaturated 18-carbon PUFAs over 20-carbon substrates, and could not convert ARA into EPA when expressed in yeast. The sdd17 -encoded desaturase was also functional in transgenic somatic soya bean embryos, resulting in the production of EPA from exogenously supplied ARA, thus demonstrating its potential for use in the production of EPA in transgenic oilseed crops. PMID:14651475

Oleic Acid: Natural variation and potential enhancement in oilseed crops.

USDA-ARS?s Scientific Manuscript database

Oleic acid is a monounsaturated omega 9 fatty acid (MUFA, C18:1) which can be found in various plant lipids and animal fats. Unlike omega 3 (a-linolenic acid, C18:3) and omega 6 (linoleic acid, C18:2) fatty acids which are essential because they cannot be synthesized by humans and must be obtained f...

Analytical method for the trace determination of esterified 3- and 2-monochloropropanediol and glycidyl fatty acid esters in various food matrices.

PubMed

Samaras, Vasilios G; Giri, Anupam; Zelinkova, Zuzana; Karasek, Lubomir; Buttinger, Gerhard; Wenzl, Thomas

2016-09-30

Fatty acid esters of 3-monochloro-1,2-propanediol (3-MCPDEs), of 2-monochloro-1,3-propanediol (2-MCPDEs) and of 2,3-epoxy-1-propanol or glycidol (GEs), which are considered to be deleterious to human health, may occur in a broad variety of food samples. A proper risk assessment of those substances requires the availability of robust occurrence data; in this respect concerns have been raised regarding the reliability of results obtained with the currently available methods to determine those substances in processed food. This article presents an indirect analytical procedure for the simultaneous determination of 3-MCPDEs, 2-MCPDEs and GEs in a wide variety of food products after extraction by pressurised liquid extraction (PLE) and determination by gas chromatography mass-spectrometry (GC-MS). For the differentiation of MCPDEs and GEs, the latter were first converted to monobromopropanediol esters (MBPDEs) in acid aqueous solution of sodium bromide. MCPDEs and MBPDEs were then hydrolysed under acidic conditions followed by derivatisation of the released free (non-esterified) form in ethyl acetate with phenyl boronic acid (PBA). Quantification of the analytes was carried out using the isotopic labelled analogues of both MCPDEs and GEs. Limits of detection (LODs) and limits of quantitation (LOQs) were in the range of 7-17mgkg(-1) and 13-31mgkg(-1) respectively, while the working range of the method was between LOQ and 1850mgkg(-1) expressed on fat basis. The developed method was successfully applied for the analysis of the target compounds in more than 650 different food samples covering the following commodities: bread and rolls, fine bakery wares, smoked fish products, fried and roasted meat, potato based snacks and fried potato products, cereal-based snacks and margarines. Copyright © 2016 The Authors. Published by Elsevier B.V. All rights reserved.

Transesterification process to manufacture ethyl ester of rape oil

DOE Office of Scientific and Technical Information (OSTI.GOV)

Korus, R.A.; Hoffman, D.S.; Bam, N.

1993-12-31

A process for the production of the ethyl ester of winter rape [EEWR] for use as a biodiesel fuel has been studied. The essential part of the process is the transesterification of rape oil with ethanol, in the presence of a catalyst, to yield the ethyl ester of rape oil as a product and glycerin as a by-product. Experiments have been performed to determine the optimum conditions for the preparation of EEWR. The process variables were: (1) temperature, (2) catalyst, (3) rate of agitation, (4) water content of the alcohol used, and (5) the amount of excess alcohol used. Themore » optimum conditions were: (1) room temperature, (2) 0.5% sodium methoxide or 1% potassium hydroxide catalyst by weight of rapeseed oil, (3) extremely vigorous agitation with some splashing during the initial phase of the reaction and agitation was not necessary after the reaction mixture became homogeneous, (4) absolute ethanol was necessary for high conversion, and (5) 50% excess ethanol with NaOCH{sub 3} or 100% excess with KOH gave a maximum conversion. Viscosity, cloud point and pour point of the EEWR were measured. A preliminary break-even cost for the commercial production of EEWR was found to be $0.55/liter [$2.08/US gallon].« less

Combined effects of fermentation temperature and pH on kinetic changes of chemical constituents of durian wine fermented with Saccharomyces cerevisiae.

PubMed

Lu, Yuyun; Voon, Marilyn Kai Wen; Huang, Dejian; Lee, Pin-Rou; Liu, Shao-Quan

2017-04-01

This study investigated the effects of temperature (20 and 30 °C) and pH (pH 3.1, 3.9) on kinetic changes of chemical constituents of the durian wine fermented with Saccharomyces cerevisiae. Temperature significantly affected growth of S. cerevisiae EC-1118 regardless of pH with a higher temperature leading to a faster cell death. The pH had a more significant effect on ethanol production than temperature with higher production at 20 °C (5.95%, v/v) and 30 °C (5.56%, v/v) at pH 3.9, relative to that at pH 3.1 (5.25 and 5.01%, v/v). However, relatively higher levels of isobutyl alcohol and isoamyl alcohol up to 64.52 ± 6.39 and 56.27 ± 3.00 mg/L, respectively, were produced at pH 3.1 than at pH 3.9 regardless of temperature. In contrast, production of esters was more affected by temperature than pH, where levels of ethyl esters (ethyl esters of octanoate, nonanoate, and decanoate) and acetate esters (ethyl acetate and isoamyl acetate) were significantly higher up to 2.13 ± 0.23 and 4.61 ± 0.22 mg/L, respectively, at 20 °C than at 30 °C. On the other hand, higher temperature improved the reduction of volatile sulfur compounds. This study illustrated that temperature control would be a more effective tool than pH in modulating the resulting aroma compound profile of durian wine.

Odor-Active Compounds in the Special Flavor Hops Huell Melon and Polaris.

PubMed

Neiens, Silva D; Steinhaus, Martin

2018-02-14

The volatiles isolated from samples of the special flavor hop varieties, Huell Melon and Polaris, and from the aroma hop variety, Hallertau Tradition, by solvent extraction and solvent-assisted flavor evaporation (SAFE) were subjected to a comparative aroma extract dilution analysis (cAEDA), which resulted in 46 odor-active compounds in the flavor dilution (FD) factor range of 16 to 2048. On the basis of high FD factors, myrcene, (3R)-linalool, and 2- and 3-methylbutanoic acid were confirmed as important variety-independent hop odorants. (1R,4S)-Calamenene was identified for the first time as an odor-active compound in hops. Clear differences in the FD factors and their subsequent objectification by stable isotope dilution quantitation suggested that high concentrations of the esters ethyl 2-methylbutanoate, ethyl 2-methylpropanoate, and propyl 2-methylbutanoate cause the characteristic fruity, cantaloupe-like odor note in Huell Melon hops, whereas the fruity and minty odor notes in Polaris are associated with high amounts of 3-methylbutyl acetate and 1,8-cineole.

Two-Stage Enzymatic Preparation of Eicosapentaenoic Acid (EPA) And Docosahexaenoic Acid (DHA) Enriched Fish Oil Triacylglycerols.

PubMed

Zhang, Zhen; Liu, Fang; Ma, Xiang; Huang, Huihua; Wang, Yong

2018-01-10

Fish oil products in the form of triacylglycerols generally have relatively low contents of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and so it is of potential research and industrial interest to enrich the related contents in commercial products. Thereby an economical and efficient two-stage preparation of EPA and DHA enriched fish oil triacylglycerols is proposed in this study. The first stage was the partial hydrolysis of fish oil by only 0.2 wt.‰ AY "Amano" 400SD which led to increases of EPA and DHA contents in acylglycerols from 19.30 and 13.09 wt % to 25.95 and 22.06 wt %, respectively. Subsequently, products of the first stage were subjected to transesterification with EPA and DHA enriched fatty acid ethyl esters (EDEE) as the second stage to afford EPA and DHA enriched fish oil triacylglycerols by using as low as 2 wt % Novozyme 435. EDEEs prepared from fish oil ethyl ester, and recycled DHA and EPA, respectively, were applied in this stage. Final products prepared with two different sources of EDEEs were composed of 97.62 and 95.92 wt % of triacylglycerols, respectively, with EPA and DHA contents of 28.20 and 21.41 wt % for the former and 25.61 and 17.40 wt % for the latter. Results not only demonstrate this two-stage process's capability and industrial value for enriching EPA and DHA in fish oil products, but also offer new opportunities for the development of fortified fish oil products.

Development and validation of a Partial Least Squares-Discriminant Analysis (PLS-DA) model based on the determination of ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs) in hair for the diagnosis of chronic alcohol abuse.

PubMed

Alladio, E; Giacomelli, L; Biosa, G; Corcia, D Di; Gerace, E; Salomone, A; Vincenti, M

2018-01-01

The chronic intake of an excessive amount of alcohol is currently ascertained by determining the concentration of direct alcohol metabolites in the hair samples of the alleged abusers, including ethyl glucuronide (EtG) and, less frequently, fatty acid ethyl esters (FAEEs). Indirect blood biomarkers of alcohol abuse are still determined to support hair EtG results and diagnose a consequent liver impairment. In the present study, the supporting role of hair FAEEs is compared with indirect blood biomarkers with respect to the contexts in which hair EtG interpretation is uncertain. Receiver Operating Characteristics (ROC) curves and multivariate Principal Component Analysis (PCA) demonstrated much stronger correlation of EtG results with FAEEs than with any single indirect biomarker or their combinations. Partial Least Squares Discriminant Analysis (PLS-DA) models based on hair EtG and FAEEs were developed to maximize the biomarkers information content on a multivariate background. The final PLS-DA model yielded 100% correct classification on a training/evaluation dataset of 155 subjects, including both chronic alcohol abusers and social drinkers. Then, the PLS-DA model was validated on an external dataset of 81 individual providing optimal discrimination ability between chronic alcohol abusers and social drinkers, in terms of specificity and sensitivity. The PLS-DA scores obtained for each subject, with respect to the PLS-DA model threshold that separates the probabilistic distributions for the two classes, furnished a likelihood ratio value, which in turn conveys the strength of the experimental data support to the classification decision, within a Bayesian logic. Typical boundary real cases from daily work are discussed, too. Copyright © 2017 Elsevier B.V. All rights reserved.

Cardiovascular benefits of omega-3 fatty acids.

PubMed

von Schacky, Clemens; Harris, William S

2007-01-15

Cardiac societies recommend the intake of 1 g/day of the two omega-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) for cardiovascular disease prevention, treatment after a myocardial infarction, prevention of sudden death, and secondary prevention of cardiovascular disease. These recommendations are based on a body of scientific evidence that encompasses literally thousands of publications. Of four large scale intervention studies three also support the recommendations of these cardiac societies. One methodologically questionable study with a negative result led a Cochrane meta-analysis to a null conclusion. This null conclusion, however, has not swayed the recommendations of the cardiac societies mentioned, and has been refuted with good reason by scientific societies. Based on the scientific evidence just mentioned, we propose a new risk factor to be considered for sudden cardiac death, the omega-3 index. It is measured in red blood cells, and is expressed as a percentage of EPA + DHA of total fatty acids. An omega-3 index of >8% is associated with 90% less risk for sudden cardiac death, as compared to an omega-3 index of <4%. The omega-3 index as a risk factor for sudden cardiac death has striking similarities to LDL as a risk factor for coronary artery disease. Moreover, the omega-3 index reflects the omega-3 fatty acid status of a given individual (analogous to HbA1c reflecting glucose homeostasis). The omega-3 index can therefore be used as a goal for treatment with EPA and DHA. As is the case now for LDL, in the future, the cardiac societies might very well recommend treatment with EPA and DHA to become goal oriented (e.g. an omega-3 index>8%).

The time course of erythrocyte membrane fatty acid concentrations during and after treatment of non-human primates with increasing doses of an omega-3 rich phospholipid preparation derived from krill-oil.

PubMed

Hals, Petter-Arnt; Wang, Xiaoli; Piscitelli, Fabiana; Di Marzo, Vincenzo; Xiao, Yong-Fu

2017-01-21

A commonly used measure to reflect the intake of the long-chain omega-3 fatty acids EPA and DHA is the omega-3 index, defined as the sum of EPA + DHA as % of total fatty acids in erythrocyte membrane. When the omega-3 index changes it follows that the relative fractions of other fatty acids in the membrane are also changed. In the present study, increasing doses of a preparation of omega-3 rich phospholipids extracted from krill oil were administered orally to non-human primates for 12 weeks and the time course of EPA, DHA and 22 other fatty acids in erythrocytes was determined bi-weekly during treatment and for 8 weeks after cessation of treatment. Plasma concentrations of six endocannabinoid-type mediators being downstream metabolites of some fatty acids analyzed in erythrocytes were also determined. Six diabetic, dyslipidemic non-human primates were included, three in a vehicle control group and three being treated with the omega-3 rich phospholipid preparation. The vehicle control and test items were given daily by gavage and the test item doses were 50, 150 and 450 mg phospholipids/kg/day. Each dose level was given for four weeks. Blood was sampled at baseline and thereafter bi-weekly. Fatty acids were determined in erythrocytes by methylation followed by gas-chromatography. Endocannabinoids and endocannabinoid-like mediators were analyzed in plasma by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. The treatment resulted in a dose-related increase in the fraction of EPA and DHA in erythrocyte membranes and a dose-related decrease of other poly-unsaturated fatty acids, in particular omega-6 polyunsaturated fatty acids. Erythrocyte concentrations of saturated fatty acids remained unchanged throughout the experiment. Plasma concentrations of endocannabinoids and endocannabinoid-like mediators changed accordingly as those being downstream arachidonic acid decreased, downstream of the saturated palmitic and oleic acids remained unchanged while a downstream EPA metabolite increased. Increasing the omega-3 index by administering an omega-3 rich phospholipid extracted from krill oil did not alter the ratio of unsaturated vs. saturated fatty acids in the erythrocyte membranes but only the relative concentrations of unsaturated fatty acids, in particular unsaturated omega-6 fatty acids. Concentrations of saturated fatty acids remained unchanged.

N-3 Polyunsaturated Fatty Acids through the Lifespan: Implication for Psychopathology

PubMed Central

Pusceddu, Matteo M.; Kelly, Philip; Stanton, Catherine; Cryan, John F.

2016-01-01

Objective: The impact of lifetime dietary habits and their role in physical, mental, and social well-being has been the focus of considerable recent research. Omega-3 polyunsaturated fatty acids as a dietary constituent have been under the spotlight for decades. Omega-3 polyunsaturated fatty acids constitute key regulating factors of neurotransmission, neurogenesis, and neuroinflammation and are thereby fundamental for development, functioning, and aging of the CNS. Of note is the fact that these processes are altered in various psychiatric disorders, including attention deficit hyperactivity disorder, depression, and Alzheimer’s disease. Design: Relevant literature was identified through a search of MEDLINE via PubMed using the following words, “n-3 PUFAs,” “EPA,” and “DHA” in combination with “stress,” “cognition,” “ADHD,” “anxiety,” “depression,” “bipolar disorder,” “schizophrenia,” and “Alzheimer.” The principal focus was on the role of omega-3 polyunsaturated fatty acids throughout the lifespan and their implication for psychopathologies. Recommendations for future investigation on the potential clinical value of omega-3 polyunsaturated fatty acids were examined. Results: The inconsistent and inconclusive results from randomized clinical trials limits the usage of omega-3 polyunsaturated fatty acids in clinical practice. However, a body of literature demonstrates an inverse correlation between omega-3 polyunsaturated fatty acid levels and quality of life/ psychiatric diseases. Specifically, older healthy adults showing low habitual intake of omega-3 polyunsaturated fatty acids benefit most from consuming them, showing improved age-related cognitive decline. Conclusions: Although further studies are required, there is an exciting and growing body of research suggesting that omega-3 polyunsaturated fatty acids may have a potential clinical value in the prevention and treatment of psychopathologies. PMID:27608809

[Inhibition effect on Microcystis aeruginosa PCC7806 as well as separation and identification of algicidal substances isolated from Salvinia natans (L.) All].

PubMed

Zhang, Shengjuan; Xia, Wentong; Yang, Xiaohui; Zhang, Tingting

2016-05-01

To study the inhibition effect of Salvinia natans ( L. ) All. on harmful algae. With Microcystis aeruginosa as the subjects, deionized water, ethanol, acetone, ethyl acetate as solvent, four kinds of crude extracts from Salvinia natans (L.) All. were prepared, and their alga-inhibiting actions were verified, respectively. The crude extracts of Salvinia natans (L.) All. with better inhibition effect were selected. The components of algal inhibiting material through macroporous resin purification were obtained, and determined by gas chromatography-mass spectrometry (GC-MS). The algicidal effect as follows: ethyl acetate extract > acetone crude extract > ethanol crude extract > water crude extract. Meanwhile, the inhibitory substances of Salvinia natans (L.) All. may be: diacetone alcohol, methyl isobutenyl ketone, 5-methyl-2-(1-methylethyl)-1-hexanol, pentadecanal, 14-heptadecenal, cumene, butyl acetate, ascorbyl dipalmitate, 1, 2-benzenedicarboxylic acid, mono (2- ethylhexyl) ester, dibutyl phthalate and phthalic acid, butyl undecane ester. The algal inhibiting effect research of Salvinia natans (L.) All., as well as its separation and identification of allelochemicals supplys theoretical basis and practical evidence not only for algae control, but also exploitation of algal inhibiting agent.

Encapsulation of ferulic acid ethyl ester in caseinate to suppress off-flavor formation in UHT milk.

PubMed

Guan, Yongguang; Zhong, Qixin

2017-12-15

Phenolic compounds can principally suppress the off-flavor development in ultrahigh temperature (UHT) treated milk, but little has been studied for lipophilic phenolic compounds that are to be encapsulated for even distribution in milk. The objective of this work was to study physicochemical properties of ferulic acid ethyl ester (FAEE) encapsulated in sodium caseinate and the inhibition of volatile formation after UHT processing. The capsules had an average hydrodynamic diameter of 246.2±10.9nm, a polydispersity index of 0.26±0.01, and a zeta-potential of -31.72±0.74mV. The capsules and the encapsulated FAEE were stable after heating at 138°C for 16min and UV radiation at 365nm for 32h. The encapsulated FAEE at a level of 0.18-1.42mg/mL suppressed the formation of 2-acetyl-2-thiazoline in model UHT milk by 32.8-63.2% after 30-day storage at 30°C. Therefore, FAEE encapsulated in caseinate can be potentially used to improve the quality of UHT milk. Copyright © 2017 Elsevier Ltd. All rights reserved.

[Study on extracting and separating curcuminoids from Curcuma longa rhizome using ultrasound strengthen by microemulsion].

PubMed

Yue, Chun-Hua; Zheng, Li-Tao; Guo, Qi-Ming; Li, Kun-Ping

2014-05-01

To establish a new method for the extraction and separation of curcuminoids from Curcuma longa rhizome by cloud-point preconcentration using microemulsions as solvent. The spectrophotometry was used to detect the solubility of curcumin in different oil phase, emulsifier and auxiliary emulsifier, and the microemulsion prescription was used for false three-phase figure optimization. The extraction process was optimized by uniform experiment design. The curcuminoids were separated from microemulsion extract by cloud-point preconcentration. Oil phase was oleic acid ethyl ester; Emulsifier was OP emulsifier; Auxiliary emulsifier was polyethylene glycol(peg) 400; The quantity of emulsifier to auxiliary emulsifier was the ratio of 5: 1; Microemulsion prescription was water-oleic acid ethyl ester-mixed emulsifier (0.45:0.1:0.45). The optimum extraction process was: time for 12.5 min, temperature of 52 degrees C, power of 360 W, frequency of 400 kHz, and the liquid-solid ratio of 40:1. The extraction rate of curcuminoids was 92.17% and 86.85% in microemulsion and oil phase, respectively. Curcuminoids is soluble in this microemulsion prescription with good extraction rate. This method is simple and suitable for curcuminoids extraction from Curcuma longa rhizome.

sal Genes Determining the Catabolism of Salicylate Esters Are Part of a Supraoperonic Cluster of Catabolic Genes in Acinetobacter sp. Strain ADP1

PubMed Central

Jones, Rheinallt M.; Pagmantidis, Vassilis; Williams, Peter A.

2000-01-01

A 5-kbp region upstream of the are-ben-cat genes was cloned from Acinetobacter sp. strain ADP1, extending the supraoperonic cluster of catabolic genes to 30 kbp. Four open reading frames, salA, salR, salE, and salD, were identified from the nucleotide sequence. Reverse transcription-PCR studies suggested that these open reading frames are organized into two convergent transcription units, salAR and salDE. The salE gene, encoding a protein of 239 residues, was ligated into expression vector pET5a. Its product, SalE, was shown to have esterase activity against short-chain alkyl esters of 4-nitrophenol but was also able to hydrolyze ethyl salicylate to ethanol and salicylic acid. A mutant of ADP1 with a Kmr cassette introduced into salE had lost the ability to utilize only ethyl and methyl salicylates of the esters tested as sole carbon sources, and no esterase activity against ethyl salicylate could be detected in cell extracts. SalE was induced during growth on ethyl salicylate but not during growth on salicylate itself. salD encoded a protein of undetermined function with homologies to the Escherichia coli FadL membrane protein, which is involved in facilitating fatty acid transport, and a number of other proteins detected during aromatic catabolism, which may also function in hydrocarbon transport or uptake processes. A Kmr cassette insertion in salD deleteriously affected cell growth and viability. The salA and salR gene products closely resemble two Pseudomonas proteins, NahG and NahR, respectively encoding salicylate hydroxylase and the LysR family regulator of both salicylate and naphthalene catabolism. salA was cloned into pUC18 together with salR and salE, and its gene product showed salicylate-inducible hydroxylase activity against a range of substituted salicylates, with the same relative specific activities as found in wild-type ADP1 grown on salicylate. Mutations involving insertion of Kmr cassettes into salA and salR eliminated expression of salicylate hydroxylase activity and the ability to grow on either salicylate or ethyl salicylate. Studies of mutants with disruptions of genes of the β-ketoadipate pathway with or without an additional salE mutation confirmed that ethyl salicylate and salicylate were channeled into the β-ketoadipate pathway at the level of catechol and thence dissimilated by the cat gene products. SalR appeared to regulate expression of salA but not salE. PMID:10715011

Inhibitory effects of omega-3 fatty acids on early brain injury after subarachnoid hemorrhage in rats: Possible involvement of G protein-coupled receptor 120/β-arrestin2/TGF-β activated kinase-1 binding protein-1 signaling pathway.

PubMed

Yin, Jia; Li, Haiying; Meng, Chengjie; Chen, Dongdong; Chen, Zhouqing; Wang, Yibin; Wang, Zhong; Chen, Gang

2016-06-01

Omega-3 fatty acids have been reported to improve neuron functions during aging and in patients affected by mild cognitive impairment, and mediate potent anti-inflammatory via G protein-coupled receptor 120 (GPR120) signal pathway. Neuron dysfunction and inflammatory response also contributed to the progression of subarachnoid hemorrhage (SAH)-induced early brain injury (EBI). This study was to examine the effects of omega-3 fatty acids on SAH-induced EBI. Two weeks before SAH, 30% Omega-3 fatty acids was administered by oral gavage at 1g/kg body weight once every 24h. Specific siRNA for GPR120 was exploited. Terminal deoxynucleotidyl transferase dUTP nick end labeling, fluoro-Jade B staining, and neurobehavioral scores and brain water content test showed that omega-3 fatty acids effectively suppressed SAH-induced brain cell apoptosis and neuronal degradation, behavioral impairment, and brain edema. Western blot, immunoprecipitation, and electrophoretic mobility shift assays results showed that omega-3 fatty acids effectively suppressed SAH-induced elevation of inflammatory factors, including cyclooxygenase-2, monocyte chemoattractant protein-1, and inducible nitric oxide synthase. In addition, omega-3 fatty acids could inhibit phosphorylation of transforming growth factor β activated kinase-1 (TAK1), MEK4, c-Jun N-terminal kinase, and IkappaB kinase as well as activation of nuclear factor kappa B through regulating GPR120/β-arrestin2/TAK1 binding protein-1 pathway. Furthermore, siRNA-induced GPR120 silencing blocked the protective effects of omega-3 fatty acids. Here, we show that stimulation of GPR120 with omega-3 fatty acids pretreatment causes anti-apoptosis and anti-inflammatory effects via β-arrestin2/TAK1 binding protein-1/TAK1 pathway in the brains of SAH rats. Fish omega-3 fatty acids as part of a daily diet may reduce EBI in an experimental rat model of SAH. Copyright © 2016 Elsevier Ltd. All rights reserved.

Associations Between Whole Blood and Dietary Omega-3 Polyunsaturated Fatty Acid Levels in Collegiate Athletes.

PubMed

Wilson, Patrick B; Madrigal, Leilani A

2016-12-01

Omega-3 polyunsaturated fatty acids (PUFAs) have important physiological functions and may offer select benefits for athletic performance and recovery. The purpose of this investigation was to assess dietary and whole blood omega-3 PUFAs among collegiate athletes. In addition, a brief questionnaire was evaluated as a valid tool for quantifying omega-3 PUFA intake. Fifty-eight athletes (9 males, 49 females) completed a 21-item questionnaire developed to assess omega-3 PUFA intake and provided dried whole blood samples to quantify α-linolenic acid (ALA), eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), and the HS-Omega-3 Index. Geometric means (95% confidence intervals) for the HS-Omega-3 Index were 4.79% (4.37-5.25%) and 4.75% (4.50-5.01%) for males and females, respectively. Median dietary intakes of ALA, EPA, and DHA were all below 100 mg. Among females, several dietary omega-3 PUFA variables were positively associated with whole blood EPA, with total EPA (rho = 0.67, p < .001) and total DHA (rho = 0.69, p < .001) intakes showing the strongest correlations. Whole blood DHA among females showed positive associations with dietary intakes, with total EPA (rho = 0.62, p < .001) and total DHA (rho = 0.64, p < .001) intakes demonstrating the strongest correlations. The HS-Omega-3 Index in females was positively correlated with all dietary variables except ALA. Among males, the only significant correlation was between food and whole blood EPA (rho = 0.83, p < .01). Collegiate athletes had relatively low intakes of omega-3 PUFAs. A 21-item questionnaire may be useful for screening female athletes for poor omega-3 PUFA status.

Replication of a Gene-Diet Interaction at CD36, NOS3 and PPARG in Response to Omega-3 Fatty Acid Supplements on Blood Lipids: A Double-Blind Randomized Controlled Trial.

PubMed

Zheng, Ju-Sheng; Chen, Jiewen; Wang, Ling; Yang, Hong; Fang, Ling; Yu, Ying; Yuan, Liping; Feng, Jueping; Li, Kelei; Tang, Jun; Lin, Mei; Lai, Chao-Qiang; Li, Duo

2018-05-01

Modulation of genetic variants on the effect of omega-3 fatty acid supplements on blood lipids is still unclear. In a double-blind randomized controlled trial, 150 patients with type 2 diabetes (T2D) were randomized into omega-3 fatty acid group (n = 56 for fish oil and 44 for flaxseed oil) and control group (n = 50) for 180 days. All patients were genotyped for genetic variants at CD36 (rs1527483), NOS3 (rs1799983) and PPARG (rs1801282). Linear regression was used to examine the interaction between omega-3 fatty acid intervention and CD36, NOS3 or PPARG variants for blood lipids. Significant interaction with omega-3 fatty acid supplements was observed for CD36 on triglycerides (p-interaction = 0.042) and PPAGR on low-density lipoprotein-cholesterol (p-interaction = 0.02). We also found a significant interaction between change in erythrocyte phospholipid omega-3 fatty acid composition and NOS3 genotype on triglycerides (p-interaction = 0.042), total cholesterol (p-interaction = 0.013) and ratio of total cholesterol to high-density lipoprotein cholesterol (p-interaction = 0.015). The T2D patients of CD36-G allele, PPARG-G allele and NOS3-A allele tended to respond better to omega-3 fatty acids in improving lipid profiles. The interaction results of the omega-3 fatty acid group were mainly attributed to the fish oil supplements. This study suggests that T2D patients with different genotypes at CD36, NOS3 and PPARG respond differentially to intervention of omega-3 supplements in blood lipid profiles. Copyright © 2018 The Authors. Published by Elsevier B.V. All rights reserved.

Hexadecenoic Fatty Acid Isomers in Human Blood Lipids and Their Relevance for the Interpretation of Lipidomic Profiles

PubMed Central

Sansone, Anna; Tolika, Evanthia; Louka, Maria; Sunda, Valentina; Deplano, Simone; Melchiorre, Michele; Anagnostopoulos, Dimitrios; Chatgilialoglu, Chryssostomos; Formisano, Cesare; Di Micco, Rosa; Faraone Mennella, Maria Rosaria; Ferreri, Carla

2016-01-01

Monounsaturated fatty acids (MUFA) are emerging health biomarkers, and in particular the ratio between palmitoleic acid (9cis-16:1) and palmitic acid (16:0) affords the delta-9 desaturase index that is increased in obesity. Recently, other positional and geometrical MUFA isomers belonging to the hexadecenoic family (C16 MUFA) were found in circulating lipids, such as sapienic acid (6cis-16:1), palmitelaidic acid (9trans-16:1) and 6trans-16:1. In this work we report: i) the identification of sapienic acid as component of human erythrocyte membrane phospholipids with significant increase in morbidly obese patients (n = 50) compared with age-matched lean controls (n = 50); and ii) the first comparison of erythrocyte membrane phospholipids (PL) and plasma cholesteryl esters (CE) in morbidly obese patients highlighting that some of their fatty acid levels have opposite trends: increases of both palmitic and sapienic acids with the decrease of linoleic acid (9cis,12cis-18:2, omega-6) in red blood cell (RBC) membrane PL were reversed in plasma CE, whereas the increase of palmitoleic acid was similar in both lipid species. Consequentially, desaturase enzymatic indexes gave different results, depending on the lipid class used for the fatty acid content. The fatty acid profile of morbidly obese subjects also showed significant increases of stearic acid (C18:0) and C20 omega-6, as well as decreases of oleic acid (9cis-18:1) and docosahexaenoic acid (C22:6 omega-3) as compared with lean healthy controls. Trans monounsaturated and polyunsaturated fatty acids were also measured and found significantly increased in both lipid classes of morbidly obese subjects. These results highlight the C16 MUFA isomers as emerging metabolic marker provided that the assignment of the double bond position and geometry is correctly performed, thus identifying the corresponding lipidomic pathway. Since RBC membrane PL and plasma CE have different fatty acid trends, caution must also be used in the choice of lipid species for the interpretation of lipidomic profiles. PMID:27045677

Hexadecenoic Fatty Acid Isomers in Human Blood Lipids and Their Relevance for the Interpretation of Lipidomic Profiles.

PubMed

Sansone, Anna; Tolika, Evanthia; Louka, Maria; Sunda, Valentina; Deplano, Simone; Melchiorre, Michele; Anagnostopoulos, Dimitrios; Chatgilialoglu, Chryssostomos; Formisano, Cesare; Di Micco, Rosa; Faraone Mennella, Maria Rosaria; Ferreri, Carla

2016-01-01

Monounsaturated fatty acids (MUFA) are emerging health biomarkers, and in particular the ratio between palmitoleic acid (9cis-16:1) and palmitic acid (16:0) affords the delta-9 desaturase index that is increased in obesity. Recently, other positional and geometrical MUFA isomers belonging to the hexadecenoic family (C16 MUFA) were found in circulating lipids, such as sapienic acid (6cis-16:1), palmitelaidic acid (9trans-16:1) and 6trans-16:1. In this work we report: i) the identification of sapienic acid as component of human erythrocyte membrane phospholipids with significant increase in morbidly obese patients (n = 50) compared with age-matched lean controls (n = 50); and ii) the first comparison of erythrocyte membrane phospholipids (PL) and plasma cholesteryl esters (CE) in morbidly obese patients highlighting that some of their fatty acid levels have opposite trends: increases of both palmitic and sapienic acids with the decrease of linoleic acid (9cis,12cis-18:2, omega-6) in red blood cell (RBC) membrane PL were reversed in plasma CE, whereas the increase of palmitoleic acid was similar in both lipid species. Consequentially, desaturase enzymatic indexes gave different results, depending on the lipid class used for the fatty acid content. The fatty acid profile of morbidly obese subjects also showed significant increases of stearic acid (C18:0) and C20 omega-6, as well as decreases of oleic acid (9cis-18:1) and docosahexaenoic acid (C22:6 omega-3) as compared with lean healthy controls. Trans monounsaturated and polyunsaturated fatty acids were also measured and found significantly increased in both lipid classes of morbidly obese subjects. These results highlight the C16 MUFA isomers as emerging metabolic marker provided that the assignment of the double bond position and geometry is correctly performed, thus identifying the corresponding lipidomic pathway. Since RBC membrane PL and plasma CE have different fatty acid trends, caution must also be used in the choice of lipid species for the interpretation of lipidomic profiles.

Absolute versus relative measures of plasma fatty acids and health outcomes: example of phospholipid omega-3 and omega-6 fatty acids and all-cause mortality in women.

PubMed

Miura, Kyoko; Hughes, Maria Celia B; Ungerer, Jacobus P J; Smith, David D; Green, Adèle C

2018-03-01

In a well-characterised community-based prospective study, we aimed to systematically assess the differences in associations of plasma omega-3 and omega-6 fatty acid (FA) status with all-cause mortality when plasma FA status is expressed in absolute concentrations versus relative levels. In a community sample of 564 women aged 25-75 years in Queensland, Australia, baseline plasma phospholipid FA levels were measured using gas chromatography. Specific FAs analysed were eicosapentaenoic acid, docosapentaenoic acid, docosahexaenoic acid, total long-chain omega-3 FAs, linoleic acid, arachidonic acid, and total omega-6 FAs. Levels of each FA were expressed in absolute amounts (µg/mL) and relative levels (% of total FAs) and divided into thirds. Deaths were monitored for 17 years and hazard ratios and 95% confidence intervals calculated to assess risk of death according to absolute versus relative plasma FA levels. In total 81 (14%) women died during follow-up. Agreement between absolute and relative measures of plasma FAs was higher in omega-3 than omega-6 FAs. The results of multivariate analyses for risk of all-cause mortality were generally similar with risk tending to inverse associations with plasma phospholipid omega-3 FAs and no association with omega-6 FAs. Sensitivity analyses examining effects of age and presence of serious medical conditions on risk of mortality did not alter findings. The directions and magnitude of associations with mortality of absolute versus relative FA levels were comparable. However, plasma FA expressed as absolute concentrations may be preferred for ease of comparison and since relative units can be deduced from absolute units.

Vitamin E supplementation modulates the biological effects of omega-3 fatty acids in naturally aged rats.

PubMed

Narayanankutty, Arunaksharan; Kottekkat, Anagha; Mathew, Shaji E; Illam, Soorya P; Suseela, Indu M; Raghavamenon, Achuthan C

2017-03-01

Omega-3 fatty acids are well-known class of nutraceuticals with established health benefits. Recently, the oxidation products of these fatty acids are gaining attention, as they are likely to disturb body redox balance. Therefore, the efficacy of omega-3 fats under conditions of diminished antioxidant status, such as aging, is always a concern. Present study assessed the effects of omega-3 fats (DHA and EPA) together with or without vitamin-E in naturally aged rats. It was found that in omega-3 fats alone consumed rats the lipid profile was improved, while in omega-3 fat with vitamin-E-consumed group (OMVE), the hepato protective and antioxidant properties were pronounced, especially the redox status of brain tissue. It is possible that vitamin-E might have reduced the peroxidation of omega-3 fats, thereby allowing their synergistic effects. Hence, the use of vitamin-E along with omega-3 fat may be beneficial under aged conditions.

Marine omega-3 fatty acids and mood disorders--linking the sea and the soul. 'Food for Thought' I.

PubMed

Hegarty, B D; Parker, G B

2011-07-01

While there has long been interest in any nutritional contribution to the onset and treatment of mood disorders, there has been increasing scientific evaluation of several candidate nutritional and dietary factors in recent years. In this inaugural study of our 'Food for Thought' series, we will overview the evidence for any role of omega-3 fatty acids (FA) in regulating mood. Relevant literature was identified through online database searches and cross-referencing. Plausible mechanisms exist by which omega-3 FA may influence neuronal function and mood. Cross-sectional studies demonstrate an association between omega-3 fatty acid deficiency and both depressive and bipolar disorders. Studies investigating the efficacy of omega-3 fatty acid supplementation for mood disorders have however provided inconsistent results. The proportion of treatment studies showing a significant advantage of omega-3 supplementation has dropped over the last 5 years. However, the vast heterogeneity of the trials in terms of constituent omega-3 FAs, dose and length of treatment makes comparisons of these studies difficult. More research is required before omega-3 supplementation can be firmly recommended as an effective treatment for mood disorders. Whereas increased omega-3 FA intake may alleviate depressive symptoms, there is little evidence of any benefit for mania. © 2011 John Wiley & Sons A/S.

Synthesis, biological activity and dyeing performance of some novel azo disperse dyes incorporating pyrazolo[1,5-a]pyrimidines for dyeing of polyester fabrics

NASA Astrophysics Data System (ADS)

Sayed, Ahmed Z.; Aboul-Fetouh, Mahmoud S.; Nassar, Hesham S.

2012-02-01

Several novel pyrazolopyrimidine azo compounds were achieved from diazotization of 4-aminoacetanilide and coupling with malononitrile and then refluxed with hydrazine hydrate to furnish 3,5-diamino-4-(4-acetamidophenylazo)-1H-pyrazole. The later compound was diazotized and coupled with substituted α-cyanocinnamate, α-cyanocinnamonitrile, 2-cyano-3-ethoxyacrylic acid ethyl ester, chalcones and ethylacetoacetate to produce novel dyestuffs. Structures of the dyes were fully characterized by using FT-IR, 1H NMR, mass spectroscopy and elemental analysis. The dyes were applied to polyester fiber, affording satisfactory results and showed biological activity towards various microorganisms.

Omega-3 Index and Anti-Arrhythmic Potential of Omega-3 PUFAs.

PubMed

Tribulova, Narcis; Szeiffova Bacova, Barbara; Egan Benova, Tamara; Knezl, Vladimir; Barancik, Miroslav; Slezak, Jan

2017-10-30

Omega-3 polyunsaturated fatty acids (PUFAs), namely eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are permanent subjects of interest in relation to the protection of cardiovascular health and the prevention of the incidence of both ventricular and atrial arrhythmias. The purpose of this updated review is to focus on the novel cellular and molecular effects of omega-3 PUFAs, in the context of the mechanisms and factors involved in the development of cardiac arrhythmias; to provide results of the most recent studies on the omega-3 PUFA anti-arrhythmic efficacy and to discuss the lack of the benefit in relation to omega-3 PUFA status. The evidence is in the favor of omega-3 PUFA acute and long-term treatment, perhaps with mitochondria-targeted antioxidants. However, for a more objective evaluation of the anti-arrhythmic potential of omega-3 PUFAs in clinical trials, it is necessary to monitor the basal pre-interventional omega-3 status of individuals, i.e., red blood cell content, omega-3 index and free plasma levels. In the view of evidence-based medicine, it seems to be crucial to aim to establish new approaches in the prevention of cardiac arrhythmias and associated morbidity and mortality that comes with these conditions.

Omega-3 fatty acid supplementation in perinatal settings.

PubMed

Blanchard, Dawn S

2006-01-01

The purpose of this article is (a) to explain the role of omega-3 fatty acids in human health, specifically in fetal/neonatal development, (b) to summarize the recent research behind the innovations in infant formula manufacturing and advertisement of omega-3 fatty acid supplementation for pregnant and lactating mothers, and (c) to relate the research findings to clinical practice. Omega-3 fatty acid supplementation in perinatal settings is discussed here from three vantage points: (a) supplementation of the third-trimester pregnant woman to enhance fetal development, (b) supplementation of the lactating mother to enhance development of the breastfeeding infant, and (c) supplementation of infant formulas to enhance development of the bottle-feeding infant. Supplementation can occur by increasing one's intake of foods high in omega-3 fatty acids or by ingesting fatty acid nutritional supplements. The challenge of supplementation for vegan and vegetarian women is also addressed.

The Effect of Omega-3 Fatty Acid Supplementation on the Inflammatory Response to eccentric strength exercise.

PubMed

Jouris, Kelly B; McDaniel, Jennifer L; Weiss, Edward P

2011-01-01

Omega-3 fatty acids (omega-3) have anti-inflammatory properties. However, it is not known if omega-3 supplementation attenuates exercise-induced inflammation. We tested the hypothesis that omega-3 supplementation reduces inflammation that is induced by eccentric arm curl exercise. Healthy adult men and women (n=11; 35 ± 10 y) performed eccentric biceps curls on two occasions, once after 14d of dietary omega-3 restriction (control trial) and again after 7d of 3,000 mg/d omega-3 supplementation (omega-3 trial). Before and 48 h after eccentric exercise, signs of inflammation was assessed by measuring soreness ratings, swelling (arm circumference and arm volume), and temperature (infrared skin sensor). Arm soreness increased (p < 0.0001) in response to eccentric exercise; the magnitude of increase in soreness was 15% less in the omega-3 trial (p = 0.004). Arm circumference increased after eccentric exercise in the control trial (p = 0.01) but not in the omega-3 trial (p = 0.15). However, there was no difference between trials (p = 0.45). Arm volume and skin temperature did not change in response to eccentric exercise in either trial. These findings suggest that omega-3 supplementation decreases soreness, as a marker of inflammation, after eccentric exercise. Based on these findings, omega-3 supplementation could provide benefits by minimizing post-exercise soreness and thereby facilitate exercise training in individuals ranging from athletes undergoing heavy conditioning to sedentary subjects or patients who are starting exercise programs or medical treatments such as physical therapy or cardiac rehabilitation. Key pointsDietary supplementation with omega-3 fatty acids has been shown to reduce inflammation in numerous inflammatory diseases such as rheumatoid arthritis, inflammatory bowel disease, and Chrohn's disease.Although strenuous exercise is known to cause acute increases in inflammation, it is not clear if omega-3 fatty acid supplementation attenuates this adverse response to exercise.Our research demonstrates that 3000 mg·d-1 omega-3 fatty acid supplementation minimizes the severe, delayed-onset muscle soreness that results from strenuous eccentric strength exercise.This information, along with a plethora of information showing that omega-3 fatty acid supplementation has other health benefits, demonstrates that a readily available over the counter nutritional supplement (i.e. omega-3 fatty acids) reduces delayed-onset soreness caused by strenuous strength exercise.This information has obvious relevance to athletic populations but also to other groups such as physical therapy patients and newly admitted cardiac rehabilitation patients, as muscle soreness, if left unchecked, can slow the progress in adapting to a new exercise program.Furthermore, as inflammation is known to be involved in the pathogenesis if numerous diseases, including heart disease, cancer, and diabetes, it is likely prudent for individuals to use inflammation-attenuating interventions, such as omega-3 supplementation, to keep inflammatory responses to physical activity at a minimum.

Omega-3 Fatty Acids and Skeletal Muscle Health

PubMed Central

Jeromson, Stewart; Gallagher, Iain J.; Galloway, Stuart D. R.; Hamilton, D. Lee

2015-01-01

Skeletal muscle is a plastic tissue capable of adapting and mal-adapting to physical activity and diet. The response of skeletal muscle to adaptive stimuli, such as exercise, can be modified by the prior nutritional status of the muscle. The influence of nutrition on skeletal muscle has the potential to substantially impact physical function and whole body metabolism. Animal and cell based models show that omega-3 fatty acids, in particular those of marine origin, can influence skeletal muscle metabolism. Furthermore, recent human studies demonstrate that omega-3 fatty acids of marine origin can influence the exercise and nutritional response of skeletal muscle. These studies show that the prior omega-3 status influences not only the metabolic response of muscle to nutrition, but also the functional response to a period of exercise training. Omega-3 fatty acids of marine origin therefore have the potential to alter the trajectory of a number of human diseases including the physical decline associated with aging. We explore the potential molecular mechanisms by which omega-3 fatty acids may act in skeletal muscle, considering the n-3/n-6 ratio, inflammation and lipidomic remodelling as possible mechanisms of action. Finally, we suggest some avenues for further research to clarify how omega-3 fatty acids may be exerting their biological action in skeletal muscle. PMID:26610527

Potentiation of omega-3 fatty acid antidepressant-like effects with low non-antidepressant doses of fluoxetine and mirtazapine.

PubMed

Laino, Carlos Horacio; Fonseca, Cristina; Sterin-Speziale, Norma; Slobodianik, Nora; Reinés, Analía

2010-12-01

Despite the advances in psychopharmacology, the treatment of depressive disorders is still not satisfactory. Side effects and resistance to antidepressant drugs are the greatest complications during treatment. Based on recent evidence, omega-3 fatty acids may influence vulnerability and outcome in depressive disorders. The aim of this study was to further characterize the omega-3 antidepressant-like effect in rats in terms of its behavioral features in the depression model forced swimming test either alone or in combination with antidepressants fluoxetine or mirtazapine. Ultimately, we prompted to determine the lowest dose at which omega-3 fatty acids and antidepressant drugs may still represent a pharmacological advantage when employed in combined treatments. Chronic diet supplementation with omega-3 fatty acids produced concentration-dependent antidepressant-like effects in the forced swimming test displaying a behavioral profile similar to fluoxetine but different from mirtazapine. Fluoxetine or mirtazapine at antidepressant doses (10 and 20 mg/kg/day, respectively) rendered additive effects in combination with omega-3 fatty acid supplementation (720 mg/kg/day). Beneficial effects of combined treatment were also observed at sub-effective doses (1 mg/kg/day) of fluoxetine or mirtazapine, since in combination with omega-3 fatty acids (720 mg/kg/day), antidepressants potentiated omega-3 antidepressant-like effects. The antidepressant-like effects occurred in the absence of changes in brain phospholipid classes. The therapeutic approach of combining omega-3 fatty acids with low ineffective doses of antidepressants might represent benefits in the treatment of depression, especially in patients with depression resistant to conventional treatments and even may contribute to patient compliance by decreasing the magnitude of some antidepressant dose-dependent side effects. Copyright © 2010 Elsevier B.V. All rights reserved.

Omega-3 fatty acids for cystic fibrosis.

PubMed

Oliver, Colleen; Watson, Helen

2016-01-05

Studies suggest that a diet rich in omega-3 essential fatty acids may have beneficial anti-inflammatory effects for chronic conditions such as cystic fibrosis. This is an updated version of a previously published review. To determine whether there is evidence that omega-3 polyunsaturated fatty acid supplementation reduces morbidity and mortality and to identify any adverse events associated with supplementation. We searched the Cochrane Cystic Fibrosis and Genetic Disorders Group's Trials Register comprising references identified from comprehensive electronic database searches and handsearches of relevant journals and abstract books of conference proceedings. Authors and persons interested in the subject of the review were contacted.Date of last search: 13 August 2013. Randomised controlled trials in people with cystic fibrosis comparing omega-3 fatty acid supplements with placebo. Two authors independently selected studies for inclusion, extracted data and assessed the risk of bias of the studies. The searches identified 15 studies; four studies with 91 participants (children and adults) were included; duration of studies ranged from six weeks to six months. Two studies were judged to be at low risk of bias based on adequate randomisation but this was unclear in the other two studies. Three of the studies adequately blinded patients, however, the risk of bias was unclear in all studies with regards to allocation concealment and selective reporting.Two studies compared omega-3 fatty acids to olive oil for six weeks. One study compared a liquid dietary supplement containing omega-3 fatty acids to one without for six months. One study compared omega-3 fatty acids and omega-6 fatty acids to a control (capsules with customised fatty acid blends) for three months. Only one short-term study (19 participants) comparing omega-3 to placebo reported a significant improvement in lung function and Shwachman score and a reduction in sputum volume in the omega-3 group. Another study (43 participants) demonstrated a significant increase in serum phospholipid essential fatty acid content and a significant drop in the n-6/n-3 fatty acid ratio following omega-3 fatty acid supplementation compared to control. The longer-term study (17 participants) demonstrated a significant increase in essential fatty acid content in neutrophil membranes and a significant decrease in the leukotriene B4 to leukotriene B5 ratio in participants taking omega-3 supplements compared to placebo. This review found that regular omega-3 supplements may provide some benefits for people with cystic fibrosis with relatively few adverse effects, although evidence is insufficient to draw firm conclusions or recommend routine use of these supplements in people with cystic fibrosis. This review has highlighted the lack of data for many outcomes meaningful to people with or making treatment decisions about cystic fibrosis. A large, long-term, multicentre, randomised controlled study is needed to determine any significant therapeutic effect and to assess the influence of disease severity, dosage and duration of treatment. Future researchers should note the need for additional pancreatic enzymes.

76 FR 6487 - National Center for Complementary and Alternative Medicine; Announcement of Workshop on...

Federal Register 2010, 2011, 2012, 2013, 2014

2011-02-04

... Mechanistic and Translational Research on Omega-3 Fatty Acids and Their Metabolites ACTION: Notice. SUMMARY... Research on Omega-3 Fatty Acids and their Metabolites. The purpose of this workshop is to bring together... the underlying mechanisms of Omega-3 fatty acids and their metabolites. The goal is to identify...

Omega-3 Fatty Acid Biomarkers and Subsequent Depressive Symptoms

PubMed Central

Persons, Jane E.; Robinson, Jennifer G.; Ammann, Eric M.; Coryell, William H.; Espeland, Mark A.; Harris, William S.; Manson, JoAnn E.; Fiedorowicz, Jess G.

2014-01-01

Objective We sought to determine the relationship between the omega-3 fatty acid content of red blood cell membranes (RBC), in particular docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA), and baseline and new-onset depressive symptoms in postmenopausal women. We secondarily sought to characterize the association between dietary omega-3 fatty acid intake and depressive symptomatology. Methods Study participants included 7,086 members of the Women's Health Initiative Memory Study (aged 63–81) who had an assessment of RBC omega-3 fatty acid concentrations at the baseline screening visit. Depressive symptoms at baseline and follow-up were characterized using the Burnam 8-item scale for depressive disorders (CES-D/DIS short form), and secondarily additionally inferred by antidepressant medication use. Results In multivariable-adjusted models, our primary exposure, RBC DHA+EPA, was not related to depressive symptoms by any measure at baseline or follow-up, nor were RBC total omega-3, DHA, or EPA (all p>0.2). In contrast, dietary intake of omega-3 was positively associated with depressive symptoms at baseline (adjusted OR 1.082, 95% C.I. 1.004–1.166; p=0.04 for dietary DHA+EPA and Burnam Score ≥ 0.06), although this generally did not persist at follow-up. Conclusion No relationship between RBC omega-3 levels and subsequent depressive symptoms was evident, and associations between dietary omega-3 and depressive symptoms were variable. Biomarkers of omega-3 status do not appear to be related to risk of new depression in post-menopausal women. PMID:24338726

Omega-3 fatty acids (from fish oils) for cystic fibrosis.

PubMed

McKarney, C; Everard, M; N'Diaye, T

2007-10-17

Epidemiological and other studies suggest that a diet rich in omega-3 essential fatty acids (derived from fish oil) may have beneficial anti-inflammatory effects for chronic conditions such as cystic fibrosis (CF). To determine whether there is evidence that omega-3 polyunsaturated fatty acid supplementation reduces morbidity and mortality. To identify any adverse events associated with omega-3 polyunsaturated fatty acid supplementation. We searched the Cochrane Cystic Fibrosis and Genetic Disorders Group's Trials Register comprising references identified from comprehensive electronic database searches and handsearches of relevant journals and abstract books of conference proceedings. Authors and persons interested in the subject of the review were contacted. Most recent search: April 2007 Randomised controlled trials in people with CF comparing omega-3 fatty acid supplements with placebo. Two authors independently selected the studies for inclusion in the review, independently extracted data and assessed the methodological quality of the studies. Searches identified seven studies; three of which, involving 48 participants, were eligible for inclusion in the review. Two studies compared omega-3 fatty acids to olive oil controls for a six-week treatment period. One study compared omega-3 fatty acids in the form of a liquid dietary supplement containing polyunsaturated fatty acids to a liquid dietary supplement control for six months. One short-term study (19 participants) comparing omega-3 to placebo reported a significant improvement in forced expiratory volume in one second, forced vital capacity and Shwachman score and a reduction in sputum volume in the omega-3 group. The longer-term study (17 participants) demonstrated a significant increase in essential fatty acid content in neutrophil membranes in study participants taking omega-3 supplements compared to placebo, weighted mean difference 0.90 (95% confidence interval 0.46 to 1.34). This review found that regular omega-3 supplements may provide some benefits for people with CF with relatively few adverse effects, although the evidence is insufficient to draw firm conclusions or to recommend routine use of supplements of omega-3 fatty acids in people with CF. This review has highlighted the lack of data for many of the outcomes likely to be meaningful to people with or making treatment decisions about CF. A large, long-term, multicentre, randomised controlled study is needed in order to determine if there is a significant therapeutic effect and to assess the influence of disease severity, dosage and duration of treatment. Future researchers should note the need for additional pancreatic enzymes.

The effects of vitamin D and omega-3 fatty acids co-supplementation on biomarkers of inflammation, oxidative stress and pregnancy outcomes in patients with gestational diabetes.

PubMed

Razavi, Maryamalsadat; Jamilian, Mehri; Samimi, Mansooreh; Afshar Ebrahimi, Faraneh; Taghizadeh, Mohsen; Bekhradi, Reza; Seyed Hosseini, Elahe; Haddad Kashani, Hamed; Karamali, Maryam; Asemi, Zatollah

2017-01-01

This study was carried out to determine the effects of vitamin D and omega-3 fatty acids co- supplementation on biomarkers of inflammation, oxidative stress and pregnancy outcomes in gestational diabetes (GDM) patients. This randomized, double-blind, placebo-controlled trial was conducted among 120 GDM women. Participants were randomly divided into four groups to receive: 1) 1000 mg omega-3 fatty acids containing 180 mg eicosapentaenoic acid (EPA) and 120 mg docosahexaenoic acid (DHA) twice a day + vitamin D placebo ( n  = 30); 2) 50,000 IU vitamin D every 2 weeks + omega-3 fatty acids placebo (n = 30); 3) 50,000 IU vitamin D every 2 weeks + 1000 mg omega-3 fatty acids twice a day (n = 30) and 4) vitamin D placebo + omega-3 fatty acids placebo (n = 30) for 6 weeks. Subjects who received vitamin D plus omega-3 fatty acids supplements compared with vitamin D, omega-3 fatty acids and placebo had significantly decreased high-sensitivity C-reactive protein (-2.0 ± 3.3 vs. -0.8 ± 4.4, -1.3 ± 2.4 and +0.9 ± 2.7 mg/L, respectively, P  = 0.008), malondialdehyde (-0.5 ± 0.5 vs. -0.2 ± 0.5, -0.3 ± 0.9 and +0.5 ± 1.4 μmol/L, respectively, P  < 0.001), and increased total antioxidant capacity (+92.1 ± 70.1 vs. +55.1 ± 123.6, +88.4 ± 95.2 and +1.0 ± 90.8 mmol/L, respectively, P  = 0.001) and glutathione (+95.7 ± 86.7 vs. +23.0 ± 62.3, +30.0 ± 66.5 and -7.8 ± 126.5 μmol/L, respectively, P = 0.001). In addition, vitamin D and omega-3 fatty acids co-supplementation, compared with vitamin D, omega-3 fatty acids and placebo, resulted in lower incidences of newborns' hyperbilirubinemiain ( P  = 0.037) and newborns' hospitalization ( P  = 0.037). Overall, vitamin D and omega-3 fatty acids co-supplementation for 6 weeks among GDM women had beneficial effects on some biomarkers of inflammation, oxidative stress and pregnancy outcomes.

The Effects of Omega-3 Fatty Acids Supplementation on Gene Expression Involved in the Insulin and Lipid Signaling Pathway in Patients with Polycystic Ovary Syndrome.

PubMed

Nasri, Khadijeh; Hantoushzadeh, Sedigheh; Aghadavod, Esmat; Taghizadeh, Mohsen; Asemi, Zatollah

2017-06-01

Limited data are available evaluating the effects of omega-3 fatty acids supplementation on gene expression involved in the insulin and lipid-signaling pathway in women with polycystic ovary syndrome (PCOS). This study was conducted to evaluate the effects of omega-3 fatty acids supplementation on gene expression involved in the insulin and lipid signaling pathway in women with PCOS. This randomized double blind, placebo-controlled trial was done among 60 women aged 18-40 years old and diagnosed with PCOS according to the Rotterdam criteria. Participants were randomly assigned into 2 groups to receive either 1 000 mg omega-3 fatty acids from flaxseed oil containing 400 mg α-linolenic acid (n=30) or placebo (n=30) twice a day for 12 weeks. Gene expressions involved in the insulin and lipid-signaling pathway were quantified in blood samples of PCOS women with RT-PCR method. Quantitative results of RT-PCR demonstrated that compared with the placebo, omega-3 fatty acids supplementation upregulated peroxisome proliferator-activated receptor gamma (PPAR-γ) mRNA (p=0.005) in peripheral blood mononuclear cells of women with PCOS. In addition, compared to the placebo, omega-3 fatty acids supplementation downregulated expressed levels of oxidized low-density lipoprotein receptor (LDLR) mRNA (p=0.002) in peripheral blood mononuclear cells of women with PCOS. We did not observe any significant effect of omega-3 fatty acids supplementation on expressed levels of glucose transporter 1 (GLUT-1) and lipoprotein(a) [Lp(a)] genes in peripheral blood mononuclear cells. Overall, omega-3 fatty acids supplementation for 12 weeks in PCOS women significantly improved gene expression of PPAR-γ and LDLR. © Georg Thieme Verlag KG Stuttgart · New York.

Activation of Two Different Resistance Mechanisms in Saccharomyces cerevisiae upon Exposure to Octanoic and Decanoic Acids▿ †

PubMed Central

Legras, J. L.; Erny, C.; Le Jeune, C.; Lollier, M.; Adolphe, Y.; Demuyter, C.; Delobel, P.; Blondin, B.; Karst, F.

2010-01-01

Medium-chain fatty acids (octanoic and decanoic acids) are well known as fermentation inhibitors. During must fermentation, the toxicity of these fatty acids is enhanced by ethanol and low pH, which favors their entrance in the cell, resulting in a decrease of internal pH. We present here the characterization of the mechanisms involved in the establishment of the resistance to these fatty acids. The analysis of the transcriptome response to the exposure to octanoic and decanoic acids revealed that two partially overlapping mechanisms are activated; both responses share many genes with an oxidative stress response, but some key genes were activated differentially. The transcriptome response to octanoic acid stress can be described mainly as a weak acid response, and it involves Pdr12p as the main transporter. The phenotypic analysis of knocked-out strains confirmed the role of the Pdr12p transporter under the control of WAR1 but also revealed the involvement of the Tpo1p major facilitator superfamily proteins (MFS) transporter in octanoic acid expulsion. In contrast, the resistance to decanoic acid is composite. It also involves the transporter Tpo1p and includes the activation of several genes of the beta-oxidation pathway and ethyl ester synthesis. Indeed, the induction of FAA1 and EEB1, coding for a long-chain fatty acyl coenzyme A synthetase and an alcohol acyltransferase, respectively, suggests a detoxification pathway through the production of decanoate ethyl ester. These results are confirmed by the sensitivity of strains bearing deletions for the transcription factors encoded by PDR1, STB5, OAF1, and PIP2 genes. PMID:20851956

Sex Differences in Omega-3 and -6 Fatty Acids and Health Status Among Young Adults With Acute Myocardial Infarction: Results From the VIRGO Study.

PubMed

Lu, Yuan; Ding, Qinglan; Xu, Xiao; Spatz, Erica S; Dreyer, Rachel P; D'Onofrio, Gail; Caulfield, Michael; Nasir, Khurram; Spertus, John A; Krumholz, Harlan M

2018-05-30

Young women (aged ≤55 years) with acute myocardial infarction (AMI) have poorer health status outcomes than similarly aged men. Low omega-3 fatty acids (FAs) have been implicated as risk factors for cardiovascular outcomes in AMI patients, but it is not clear whether young women have similar or different post-AMI omega-3 FA profiles compared with young men. We assessed the sex differences in post-AMI omega-3 FAs and the associations of these biomarkers with patient-reported outcomes (symptom, functioning status, and quality of life) at 12-month follow-up, using data from 2985 US adults with AMI aged 18 to 55 years enrolled in the VIRGO (Variation in Recovery: Role of Gender on Outcomes of Young Acute Myocardial Infarction Patients) study. Biomarkers including eicosapentaenoic acid, docosahexaenoic acid, arachidonic acid (AA), eicosapentaenoic acid/AA ratio, omega-3/omega-6 ratio, and omega-3 index were measured 1 month after AMI. Overall, the omega-3 FAs and AA were similar in young men and women with AMI. In both unadjusted and adjusted analysis (controlling for age, sex, race, smoking, hypertension, diabetes mellitus, body mass index, and health status score at 1 month), omega-3 FAs and AA were not significantly associated with 12-month health status scores using the Bonferroni corrected statistical threshold. We found no evidence of sex differences in omega-3 FAs and AA in young men and women 1 month after AMI. Omega-3 FAs and AA at 1-month after AMI were generally not associated with 12-month patient-reported health status after adjusting for patient demographic, clinical characteristics, and the corresponding 1-month health status score. © 2018 The Authors and Quest Diagnostics Inc. Published on behalf of the American Heart Association, Inc., by Wiley.

Cod Liver Oil

MedlinePlus

Cod liver oil contains certain "fatty acids" that prevent the blood from clotting easily. These fatty acids also reduce pain and swelling. ... Morue, Huile de Poisson, Liver Oil, N-3 Fatty Acids, Omega 3, Oméga 3, Omega 3 Fatty Acids, ...

Production of biodiesel from bioethanol and Brassica carinata oil: oxidation stability study.

PubMed

Bouaid, Abderrahim; Martinez, Mercedes; Aracil, Jose

2009-04-01

In the present work the synthesis from bioethanol and Brassica carinata, as alternative vegetable oil, using KOH as catalyst, has been developed and optimized by application of the factorial design and response surface methodology (RSM). Temperature and catalyst concentration were found to have significant influence on conversion. A second-order model was obtained to predict conversions as a function of temperature and catalyst concentration. The maximum yield of ester (98.04%) was obtained working with an initial concentration of catalyst (1.5%) and an operation temperature of (35 degrees C). Results show that the acid value, peroxide value, and viscosity, increased while the iodine value decreased with increasing storage time of the biodiesel sample. Fatty acid ethyl esters (biodiesel) from B. carinata oil were very stable because they did not demonstrate rapid increase in peroxide value, acid value, and viscosity with increasing storage time to a period of 12 months.

Quantitative analysis of fragrance and odorants released from fresh and decaying strawberries.

PubMed

Kim, Yong-Hyun; Kim, Ki-Hyun; Szulejko, Jan E; Parker, David

2013-06-20

The classes and concentrations of volatile organic compounds (VOC) released from fresh and decaying strawberries were investigated and compared. In this study, a total of 147 strawberry volatiles were quantified before and after nine days of storage to explore differences in the aroma profile between fresh strawberries (storage days (SRD) of 0, 1, and 3) and those that had started to decay (SRD = 6 and 9). In terms of concentration, seven compounds dominated the aroma profile of fresh strawberries (relative composition (RC) up to 97.4% by mass, sum concentration): (1) ethyl acetate = 518 mg∙m⁻³, (2) methyl acetate = 239 mg∙m⁻³, (3) ethyl butyrate = 13.5 mg∙m⁻³, (4) methyl butyrate = 11.1 mg∙m⁻³, (5) acetaldehyde = 24.9 mg∙m⁻³, (6) acetic acid = 15.2 mg∙m⁻³, and (7) acetone = 13.9 mg∙m⁻³. In contrast, two alcohols dominated the aroma profile of decayed samples (RC up to 98.6%): (1) ethyl alcohol = 94.2 mg∙m⁻³ and (2) isobutyl alcohol = 289 mg∙m⁻³. Alternatively; if the aroma profiles are re-evaluated by summing odor activity values (ΣOAV); four ester compounds ((1) ethyl butyrate (6,160); (2) ethyl hexanoate (3,608); (3) ethyl isovalerate (1,592); and (4) ethyl 2-methylbutyrate (942)) were identified as the key constituents of fresh strawberry aroma (SRD-0). As the strawberries began to decay; isobutyl alcohol recorded the maximum OAV of 114 (relative proportion (RP) (SRD = 6) = 58.3%). However, as the decay process continued, the total OAV dropped further by 3 to 4 orders of magnitude--decreasing to 196 on SRD = 6 to 7.37 on SRD = 9. The overall results of this study confirm dramatic changes in the aroma profile of strawberries over time, especially with the onset of decay.

Omega-6 and omega-3 polyunsaturated fatty acid levels are reduced in whole blood of Italian patients with a recent myocardial infarction: the AGE-IM study.

PubMed

Marangoni, Franca; Novo, Giuseppina; Perna, Giampiero; Perrone Filardi, Pasquale; Pirelli, Salvatore; Ceroti, Marco; Querci, Andrea; Poli, Andrea

2014-02-01

The relationship between whole blood fatty acids and myocardial infarction (MI) risk has not been analyzed in detail, especially in Mediterranean countries. The AGE-IM (Acidi Grassi Essenziali e Infarto Miocardico) study was planned to examine the relationships between MI, whole blood fatty acids and the diet in an Italian cohort. 119 Patients with a recent MI and 103 control subjects were enrolled in the study. The whole blood fatty acid composition was determined; information on anthropometrics, biochemical parameters and blood pressure values were also obtained. Diet composition was assessed using a validated food frequency questionnaire from 86 cases and 72 controls. Total PUFA, omega-6 and omega-3 PUFA (as percentage of whole blood fatty acids) were significantly lower in MI patients than in matched controls, whereas saturated and monounsaturated fatty acids were higher in cases. MI infarction risk significantly and steadily decreased with increasing levels of total PUFA (OR: 0.14) and of total omega-6 and omega-3 (OR: 0.15 and 0.37, respectively). No correlation was identified between dietary fats and MI risk or between whole blood fatty acid levels and dietary nutrients and fats. Percentage levels of total PUFA, total omega-3 PUFA and total omega-6 PUFA are lower in MI patients than in matched control subjects in the AGE-IM cohort. These data support a favorable association not only of whole blood percentage levels of total omega-3, but also of total omega-6, with cardiovascular risk. Copyright © 2013 Elsevier Ireland Ltd. All rights reserved.

A randomized clinical trial of high eicosapentaenoic acid omega-3 fatty acids and inositol as monotherapy and in combination in the treatment of pediatric bipolar spectrum disorders: a pilot study.

PubMed

Wozniak, Janet; Faraone, Stephen V; Chan, James; Tarko, Laura; Hernandez, Mariely; Davis, Jacqueline; Woodworth, K Yvonne; Biederman, Joseph

2015-11-01

We conducted a 12-week, randomized, double-blind, controlled clinical trial to evaluate the effectiveness and tolerability of high eicosapentaenoic acid (EPA)/docosahexaenoic acid (DHA) omega-3 fatty acids and inositol as monotherapy and in combination in children with bipolar spectrum disorders. Participants were children 5-12 years of age meeting DSM-IV diagnostic criteria for bipolar spectrum disorders (bipolar I or II disorder or bipolar disorder not otherwise specified [NOS]) and displaying mixed, manic, or hypomanic symptoms. Subjects with severe illness were excluded. Subjects were randomized to 1 of 3 treatment arms: inositol plus placebo, omega-3 fatty acids plus placebo, and the combined active treatment of omega-3 fatty acids plus inositol. Data were collected from February 2012 to November 2013. Twenty-four subjects were exposed to treatment (≥ 1 week of study completed) (inositol [n = 7], omega-3 fatty acids [n = 7], and omega-3 fatty acids plus inositol [n =10]). Fifty-four percent of the subjects completed the study. Subjects randomized to the omega-3 fatty acids plus inositol arm had the largest score decrease comparing improvement from baseline to end point with respect to the Young Mania Rating Scale (P < .05). Similar results were found for the Children's Depression Rating Scale (P < .05) and the Brief Psychiatric Rating Scale (P <.05). Results of this pilot randomized, double-blind, controlled trial suggest that the combined treatment of omega-3 fatty acids plus inositol reduced symptoms of mania and depression in prepubertal children with mild to moderate bipolar spectrum disorders. Results should be interpreted in light of limitations, which include exclusion of severely ill subjects, 54% completion rate, and small sample size. ClinicalTrials.gov identifier: NCT01396486. © Copyright 2015 Physicians Postgraduate Press, Inc.

Association of Omega-3 Fatty Acid and Epileptic Seizure in Epileptic Patients: A Systematic Review.

PubMed

Pourmasoumi, Makan; Vosoughi, Nooshin; Derakhshandeh-Rishehri, Seyedeh-Masoumeh; Assarroudi, Mostafa; Heidari-Beni, Motahar

2018-01-01

The evidence on the association between omega-3 consumption and epileptic seizure is inconsistent. Therefore, we have conducted this systematic review to clarify the possible relationship. Original articles were searched in electronic databases (PubMed, Scopus, Google Scholar, Cochrane, and Ovid) and by reviewing the reference lists of retrieved articles. The main evaluated outcome was the epileptic seizures. We included the English language studies that reported the original data on the effect of omega-3 on epileptic human patients. We included the nine articles with 230 patients in the present systematic review. The mean ± standard deviation age of them was about 31.01 ± 14.99 years. The average of study duration was 22 ± 15.27 weeks. Omega-3 fatty acid supplements were defined as the sum of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) (1100 mg/d); as the sum of EPA, DHA, and alpha-linolenic acid (5 g/d); and as the sum of EPA alone (565 mg/d) in different studies. Among the nine studies, four studies reported a significant positive association between omega-3 fatty acids and epileptic seizures. However, power and quality of these studies are low, and we cannot consider the beneficial effect of omega-3 on seizures. In addition, five studies did not reveal any significant effect. Majority of the included studies did not show a significant association between omega-3 and epileptic seizure in epileptic patients, but further studies are necessary. It is controversial whether omega-3 fatty acids can produce positive effects on epileptic patients or not.

Omega-3 Fatty Acids for Autistic Spectrum Disorder: A Systematic Review

ERIC Educational Resources Information Center

Bent, Stephen; Bertoglio, Kiah; Hendren, Robert L.

2009-01-01

We conducted a systematic review to determine the safety and efficacy of omega-3 fatty acids for autistic spectrum disorder (ASD). Articles were identified by a search of MEDLINE, EMBASE, and the Cochrane Database using the terms autism or autistic and omega-3 fatty acids. The search identified 143 potential articles and six satisfied all…

Effects of omega-3 fatty acids on arterial stiffness in patients with hypertension: a randomized pilot study.

PubMed

Krantz, Mori J; Havranek, Edward P; Pereira, Rocio I; Beaty, Brenda; Mehler, Philip S; Long, Carlin S

2015-12-02

Omega-3 fatty acids prevent cardiovascular disease (CVD) events in patients with myocardial infarction or heart failure. Benefits in patients without overt CVD have not been demonstrated, though most studies did not use treatment doses (3.36 g) of omega-3 fatty acids. Arterial stiffness measured by pulse wave velocity (PWV) predicts CVD events independent of standard risk factors. However, no therapy has been shown to reduce PWV in a blood pressure-independent manner. We assessed the effects of esterified omega-3 fatty acids on PWV and serum markers of inflammation among patients with hypertension. We performed a prospective, randomized; double-blinded pilot study of omega-3 fatty acids among 62 patients in an urban, safety net hospital. Patients received 3.36 g of omega-3 fatty acids vs. matched placebo daily for 3-months. The principal outcome measure was change in brachial-ankle PWV. Serum inflammatory markers associated with CVD risk were also assessed. The majority (71 %) were of Latino ethnicity. After 3-months, mean change in arterial PWV among omega-3 and placebo groups was -97 cm/s vs. -33 cm/s respectively (p = 0.36 for difference, after multivariate adjustment for baseline age, systolic blood pressure, and serum adiponectin). Non-significant reductions in lipoprotein-associated phospholipase A2 (LpPLA2) mass and high sensitivity C-reactive protein (hsCRP) relative to placebo were also observed (p = 0.08, and 0.21, respectively). High-dose omega-3 fatty acids did not reduce arterial PWV or markers of inflammation among patients within a Latino-predominant population with hypertension. NCT00935766 , registered July 8 2009.

Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification.

PubMed

Metzger, J O; Bornscheuer, U

2006-06-01

Oils and fats are the most important renewable raw materials of the chemical industry. They make available fatty acids in such purity that they may be used for chemical conversions and for the synthesis of chemically pure compounds. Oleic acid (1) from "new sunflower," linoleic acid (2) from soybean, linolenic acid (3) from linseed, erucic acid (4) from rape seed, and ricinoleic acid (5) from castor oil are most important for chemical transformations offering in addition to the carboxy group one or more C-C-double bonds. New plant oils containing fatty acids with new and interesting functionalities such as petroselinic acid (6) from Coriandrum sativum, calendic acid (7) from Calendula officinalis, alpha-eleostearic acid (8) from tung oil, santalbic acid (9) from Santalum album (Linn.), and vernolic acid (10) from Vernonia galamensis are becoming industrially available. The basic oleochemicals are free fatty acids, methyl esters, fatty alcohols, and fatty amines as well as glycerol as a by-product. Their interesting new industrial applications are the usage as environmentally friendly industrial fluids and lubricants, insulating fluid for electric utilities such as transformers and additive to asphalt. Modern methods of synthetic organic chemistry including enzymatic and microbial transformations were applied extensively to fatty compounds for the selective functionalization of the alkyl chain. Syntheses of long-chain diacids, omega-hydroxy fatty acids, and omega-unsaturated fatty acids as base chemicals derived from vegetable oils were developed. Interesting applications were opened by the epoxidation of C-C-double bonds giving the possibility of photochemically initiated cationic curing and access to polyetherpolyols. Enantiomerically pure fatty acids as part of the chiral pool of nature can be used for the synthesis of nonracemic building blocks.

The Role of Electrolyte Upon the SEI Formation Characteristics and Low Temperature Performance of Lithium-Ion Cells With Graphite Anodes

NASA Technical Reports Server (NTRS)

Smart, M. C.; Ratnakumar, B. V.; Greenbaum, S.; Surampudi, S.

2000-01-01

Quarternary lithium-ion battery electrolyte solutions containing ester co-solvents in mixtures of carbonates have been demonstrated to have high conductivity at low temperatures (< -20C). However, in some cases the presence of such co-solvents does not directly translate into improved low temperature cell performance, presumably due to the formation of ionically resistive surface films on carbonaceous anodes. In order to understand this behavior, a number of lithium-graphite cells have been studied containing electrolytes with various ester co-solvents, including methyl acetate (MA), ethyl acetate (EA), ethyl propionate (EP), and ethyl butyrate (EB). The charge/discharge characterization of these cells indicates that the higher molecular weight esters result in electrolytes which possess superior low temperature performance in contrast to the lower molecular weight ester-containing solutions, even though these solutions display lower conductivity values.

Direct hydrogenation of biomass-derived butyric acid to n-butanol over a ruthenium-tin bimetallic catalyst.

PubMed

Lee, Jong-Min; Upare, Pravin P; Chang, Jong-San; Hwang, Young Kyu; Lee, Jeong Ho; Hwang, Dong Won; Hong, Do-Young; Lee, Seung Hwan; Jeong, Myung-Geun; Kim, Young Dok; Kwon, Young-Uk

2014-11-01

Catalytic hydrogenation of organic carboxylic acids and their esters, for example, cellulosic ethanol from fermentation of acetic acid and hydrogenation of ethyl acetate is a promising possibility for future biorefinery concepts. A hybrid conversion process based on selective hydrogenation of butyric acid combined with fermentation of glucose has been developed for producing biobutanol. ZnO-supported Ru-Sn bimetallic catalysts exhibits unprecedentedly superior performance in the vapor-phase hydrogenation of biomass-derived butyric acid to n-butanol (>98% yield) for 3500 h without deactivation. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Mapping QTL for Omega-3 Content in Hybrid Saline Tilapia.

PubMed

Lin, Grace; Wang, Le; Ngoh, Si Te; Ji, Lianghui; Orbán, Laszlo; Yue, Gen Hua

2018-02-01

Tilapia is one of most important foodfish species. The low omega-3 to omega-6 fatty acid ratio in freshwater tilapia meat is disadvantageous for human health. Increasing omega-3 content is an important task in breeding to increase the nutritional value of tilapia. However, conventional breeding to increase omega-3 content is difficult and slow. To accelerate the increase of omega-3 through marker-assisted selection (MAS), we conducted QTL mapping for fatty acid contents and profiles in a F 2 family of saline tilapia generated by crossing red tilapia and Mozambique tilapia. The total omega-3 content in F 2 hybrid tilapia was 2.5 ± 1.0 mg/g, higher than that (2.00 mg/g) in freshwater tilapia. Genotyping by sequencing (GBS) technology was used to discover and genotype SNP markers, and microsatellites were also genotyped. We constructed a linkage map with 784 markers (151 microsatellites and 633 SNPs). The linkage map was 2076.7 cM long and consisted of 22 linkage groups. Significant and suggestive QTL for total lipid content were mapped on six linkage groups (LG3, -4, -6, -8, -13, and -15) and explained 5.8-8.3% of the phenotypic variance. QTL for omega-3 fatty acids were located on four LGs (LG11, -18, -19, and -20) and explained 5.0 to 7.5% of the phenotypic variance. Our data suggest that the total lipid and omega-3 fatty acid content were determined by multiple genes in tilapia. The markers flanking the QTL for omega-3 fatty acids can be used in MAS to accelerate the genetic improvements of these traits in salt-tolerant tilapia.

Influence of alcohol containing and alcohol free cosmetics on FAEE concentrations in hair. A performance evaluation of ethyl palmitate as sole marker, versus the sum of four FAEEs.

PubMed

Dumitrascu, C; Paul, R; Kingston, R; Williams, Rachel

2018-02-01

Fatty acid ethyl esters (FAEE) are direct metabolites of ethanol and have been shown to be suitable markers for the evaluation of alcohol consumption. Previous research has suggested that the regular use of alcohol containing cosmetic products can influence the concentration of FAEE detected in hair. In this study we investigated the influence of alcohol containing and alcohol free hair cosmetics (hairspray and waxes) on the FAEE concentrations in hair. The effect of cosmetic treatment was measured against the impact on ethyl palmitate in isolation as compared to the sum of four esters. 10 volunteers treated part of their scalp with cosmetic products every day during a 2 month period (alcohol free hairspray n=2, hairspray containing alcohol (42% by volume) n=3, alcohol free wax n=2, wax containing alcohol (11% by volume) n=3). After the 2 month period of cosmetic application hair samples from volunteers were collected from both sides of the scalp. Hair samples were washed with n-heptane, and then cut finely into small pieces. All samples were subjected to clean-up by HS-SPME and then GC PCI-MS/MS for analysis of FAEEs. Comparison of FAEE concentrations between treated and untreated hair showed in some instances that application of hair spray or wax products caused an increase in FAEE levels. Products containing alcohol caused a more substantial increase in alcohol metabolite concentrations in hair when compared to alcohol free products. Three volunteers using an alcohol based hairspray in the study experienced a significant increase in FAEE levels (+27.4%, +205.5%, and +1287.5%), with one of the volunteers showing levels below the cut off for 'abstinence' in the untreated scalp portion, and levels above the cut off for 'chronic excessive consumption' in the treated scalp portion. Performance evaluation of ethyl palmitate as sole marker, compared to the sum of four esters approach suggested that the two quantification approaches react in a very similar manner to the application of hair sprays and waxes. We would suggest that the interpretative value of FAEE hair measurements from people reporting the use of alcohol based hairsprays are treated with caution. Copyright © 2018 Elsevier B.V. All rights reserved.

A meta-analysis of placebo-controlled trials of omega-3 fatty acid augmentation in schizophrenia: Possible stage-specific effects.

PubMed

Chen, Alexander T; Chibnall, John T; Nasrallah, Henry A

2015-11-01

Omega-3 fatty acids have shown promise as an adjunctive treatment for schizophrenia. However, efficacy across studies has been inconsistent. We conducted a meta-analysis of published controlled studies with the goal of detecting different efficacy profiles at various stages of schizophrenia. An online search was conducted for randomized, double-blind, placebo-controlled clinical trials, and a meta-analysis was conducted. Ten studies met the criteria for inclusion. Among patients in the prodromal phase of schizophrenia, omega-3 supplementation reduced psychotic symptom severity and lowered conversion rates to first-episode psychosis. In patients with first-episode schizophrenia, omega-3 decreased nonpsychotic symptoms, required lower antipsychotic medication dosages, and improved early treatment response rates. Omega-3 had mixed results in patients with stable chronic schizophrenia, with only some patients experiencing significant benefits. Among patients with chronic schizophrenia, use of omega-3 fatty acids both by those experiencing acute exacerbations and those who had discontinued antipsychotic medications resulted in worsening of psychotic symptoms. The data suggest that omega-3 fatty acids may be efficacious in reducing clinical symptoms for patients in the earlier stages of schizophrenia (prodrome and first episode), while producing mixed results for patients in the chronic stages. Based on these results, omega-3 fatty acids would not be recommended for acute exacerbations in patients with chronic schizophrenia nor for relapse prevention after discontinuation of antipsychotics.

Tuning Chocolate Flavor through Development of Thermotolerant Saccharomyces cerevisiae Starter Cultures with Increased Acetate Ester Production

PubMed Central

Meersman, Esther; Steensels, Jan; Struyf, Nore; Paulus, Tinneke; Saels, Veerle; Mathawan, Melissa; Allegaert, Leen; Vrancken, Gino

2015-01-01

Microbial starter cultures have extensively been used to enhance the consistency and efficiency of industrial fermentations. Despite the advantages of such controlled fermentations, the fermentation involved in the production of chocolate is still a spontaneous process that relies on the natural microbiota at cocoa farms. However, recent studies indicate that certain thermotolerant Saccharomyces cerevisiae cultures can be used as starter cultures for cocoa pulp fermentation. In this study, we investigate the potential of specifically developed starter cultures to modulate chocolate aroma. Specifically, we developed several new S. cerevisiae hybrids that combine thermotolerance and efficient cocoa pulp fermentation with a high production of volatile flavor-active esters. In addition, we investigated the potential of two strains of two non-Saccharomyces species that produce very large amounts of fruity esters (Pichia kluyveri and Cyberlindnera fabianii) to modulate chocolate aroma. Gas chromatography-mass spectrometry (GC-MS) analysis of the cocoa liquor revealed an increased concentration of various flavor-active esters and a decrease in spoilage-related off-flavors in batches inoculated with S. cerevisiae starter cultures and, to a lesser extent, in batches inoculated with P. kluyveri and Cyb. fabianii. Additionally, GC-MS analysis of chocolate samples revealed that while most short-chain esters evaporated during conching, longer and more-fat-soluble ethyl and acetate esters, such as ethyl octanoate, phenylethyl acetate, ethyl phenylacetate, ethyl decanoate, and ethyl dodecanoate, remained almost unaffected. Sensory analysis by an expert panel confirmed significant differences in the aromas of chocolates produced with different starter cultures. Together, these results show that the selection of different yeast cultures opens novel avenues for modulating chocolate flavor. PMID:26590272

Tuning Chocolate Flavor through Development of Thermotolerant Saccharomyces cerevisiae Starter Cultures with Increased Acetate Ester Production.

PubMed

Meersman, Esther; Steensels, Jan; Struyf, Nore; Paulus, Tinneke; Saels, Veerle; Mathawan, Melissa; Allegaert, Leen; Vrancken, Gino; Verstrepen, Kevin J

2016-01-15

Microbial starter cultures have extensively been used to enhance the consistency and efficiency of industrial fermentations. Despite the advantages of such controlled fermentations, the fermentation involved in the production of chocolate is still a spontaneous process that relies on the natural microbiota at cocoa farms. However, recent studies indicate that certain thermotolerant Saccharomyces cerevisiae cultures can be used as starter cultures for cocoa pulp fermentation. In this study, we investigate the potential of specifically developed starter cultures to modulate chocolate aroma. Specifically, we developed several new S. cerevisiae hybrids that combine thermotolerance and efficient cocoa pulp fermentation with a high production of volatile flavor-active esters. In addition, we investigated the potential of two strains of two non-Saccharomyces species that produce very large amounts of fruity esters (Pichia kluyveri and Cyberlindnera fabianii) to modulate chocolate aroma. Gas chromatography-mass spectrometry (GC-MS) analysis of the cocoa liquor revealed an increased concentration of various flavor-active esters and a decrease in spoilage-related off-flavors in batches inoculated with S. cerevisiae starter cultures and, to a lesser extent, in batches inoculated with P. kluyveri and Cyb. fabianii. Additionally, GC-MS analysis of chocolate samples revealed that while most short-chain esters evaporated during conching, longer and more-fat-soluble ethyl and acetate esters, such as ethyl octanoate, phenylethyl acetate, ethyl phenylacetate, ethyl decanoate, and ethyl dodecanoate, remained almost unaffected. Sensory analysis by an expert panel confirmed significant differences in the aromas of chocolates produced with different starter cultures. Together, these results show that the selection of different yeast cultures opens novel avenues for modulating chocolate flavor. Copyright © 2016, American Society for Microbiology. All Rights Reserved.

Enzyme inhibitory metabolites from endophytic Penicillium citrinum isolated from Boswellia sacra.

PubMed

Ali, Sajid; Khan, Abdul Latif; Ali, Liaqat; Rizvi, Tania Shamim; Khan, Sumera Afzal; Hussain, Javid; Hamayun, Muhammad; Al-Harrasi, Ahmed

2017-07-01

Fungal endophytes establish an important niche within the host plant through the secretion of chemical constituents. Isolation of bioactive metabolites could be a vital source for inhibiting the function of enzymes such as α-glucosidase and urease. The present study aimed to elucidate the potential of endophytes associated with Boswellia sacra through bioassay-guided isolation and identification of secondary metabolites with enzyme inhibitory ability. Endophytic fungal strains viz. Penicillium citrinum, P. spinulosum, Fusarium oxysporum, Alternaria alternata and Aspergillus caespitosus were identified through genomic DNA extraction, PCR amplification, sequencing and phylogenetic analysis. The enzymes inhibition analysis of the ethyl acetate extract from pure cultures suggested that P. citrinum possess significantly higher enzyme inhibitory activities compared to other strains. The active strain was subjected to chromatographic isolation and nuclear magnetic resonance methods to identify bioactive compounds. The bioactive extracts resulted in the isolation of 11-oxoursonic acid benzyl ester (1), n-nonane (2), 3-decene-1-ol (3), 2-Hydroxyphenyl acetic acid (4), and Glochidacuminosides A (5). Among pure compound, 11-oxoursonic acid benzyl ester (1) showed significantly higher enzyme inhibition activity compared to other metabolites. Our results suggest that the endophytic microorganism associated with the arid-land tree can offer a rich source of biologically active chemical constituents that could help discover lead drugs for enzyme inhibition.

Omega-3 fatty acids and non-alcoholic fatty liver disease: Evidence of efficacy and mechanism of action.

PubMed

Scorletti, Eleonora; Byrne, Christopher D

2018-03-22

For many years it has been known that high doses of long chain omega-3 fatty acids are beneficial in the treatment of hypertriglyceridaemia. Over the last three decades, there has also been a wealth of in vitro and in vivo data that has accumulated to suggest that long chain omega-3 fatty acid treatment might be beneficial to decrease liver triacylglycerol. Several biological mechanisms have been identified that support this hypothesis; notably, it has been shown that long chain omega-3 fatty acids have a beneficial effect: a) on bioactive metabolites involved in inflammatory pathways, and b) on alteration of nuclear transcription factor activities such as peroxisome proliferator-activated receptors (PPARs), sterol regulatory element-binding protein 1c (SREBP-1c) and carbohydrate-responsive element-binding protein (ChREBP), involved in inflammatory pathways and liver lipid metabolism. Since the pathogenesis of non alcoholic fatty liver disease (NAFLD) begins with the accumulation of liver lipid and progresses with inflammation and then several years later with development of fibrosis; it has been thought in patients with NAFLD omega-3 fatty acid treatment would be beneficial in treating liver lipid and possibly also in ameliorating inflammation. Meta-analyses (of predominantly dietary studies and small trials) have tended to support the assertion that omega-3 fatty acids are beneficial in decreasing liver lipid, but recent randomised controlled trials have produced conflicting data. These trials have suggested that omega-3 fatty acid might be beneficial in decreasing liver triglyceride (docosahexanoic acid also possibly being more effective than eicosapentanoic acid) but not in decreasing other features of steatohepatitis (or liver fibrosis). The purpose of this review is to discuss recent evidence regarding biological mechanisms by which long chain omega-3 fatty acids might act to ameliorate liver disease in NAFLD; to consider the recent evidence from randomised trials in both adults and children with NAFLD; and finally to discuss key 'known unknowns' that need to be considered, before planning future studies that are focussed on testing the effects of omega-3 fatty acid treatment in patients with NAFLD. Crown Copyright © 2018. Published by Elsevier Ltd. All rights reserved.

Attractants from Bartlett pear for codling moth, Cydia pomonella (L.), larvae

NASA Astrophysics Data System (ADS)

Knight, Alan L.; Light, Douglas M.

2001-08-01

The alkyl ethyl and methyl esters of (2 E,4 Z)-2,4-decadienoic acid found in head-space samples of ripe Bartlett pear ( Pyrus communis L.) stimulated a response from neonate larvae of the codling moth (CM), Cydia pomonella (L.), in both static-air Petri-plate and in upwind Y-tube and straight-tube olfactometer bioassays. In comparison with the known CM neonate attractant, ( E,E)-α-farnesene, ethyl (2 E,4 Z)-2,4-decadienoate was attractive at 10-fold and 1,000-fold lower threshold dosages in the Petri-plate and in the Y-tube bioassays, respectively. Methyl (2 E,4 Z)-2,4-decadienoate was attractive to CM neonates in these bioassays at much higher doses than ethyl (2 E,4 Z)-2,4-decadienoate. Other principal head-space volatiles from ripe pear fruit and pear leaves, including butyl acetate, hexyl acetate, ( Z)-3-hexenyl acetate, and ( E)-β-ocimene, were not attractive to CM neonates. The potential uses of these pear kairomones for monitoring and control of CM in walnuts and apple are discussed.

Internet-Based, Randomized Controlled Trial of Omega-3 Fatty Acids for Hyperactivity in Autism

PubMed Central

Bent, Stephen; Hendren, Robert L.; Zandi, Tara; Law, Kiely; Choi, Jae-Eun; Widjaja, Felicia; Kalb, Luther; Nestle, Jay; Law, Paul

2014-01-01

Objective Preliminary evidence suggests that omega-3 fatty acids may reduce hyperactivity in children with autism spectrum disorder (ASD). We sought to examine the feasibility of a novel, internet-based clinical trial design to evaluate the efficacy of this supplement. Method E-mail invitations were sent to parents of children aged 5-8 enrolled in the Interactive Autism Network. All study procedures, including screening, informed consent, and collection of outcome measures took place over the internet. The primary outcome measures were parent- and teacher-rated changes in hyperactivity on the Aberrant Behavior Checklist. Results During the 6-week recruitment period, 57 children from 28 states satisfied all eligibility criteria and were randomly assigned to 1.3 grams of omega-3 fatty acids or an identical placebo daily for 6 weeks. Outcome assessments were obtained from all 57 participants and 57 teachers, and the study was completed in 3 months. Children in the omega-3 fatty acid group had a greater reduction in hyperactivity (-5.3 points) compared to the placebo group (-2.6 points), but the difference was not statistically significant (1.9 point greater improvement in the omega-3 group, 95% CI -2.2 to 5.2). Side effects were rare and not associated with omega-3 fatty acids. Participant feedback was positive. Conclusion Internet-based randomized controlled trials of therapies in children with ASD are feasible and may lead to marked reductions in the time and cost of completing trials. A larger sample size is required to definitively determine the efficacy of omega-3 fatty acids. Clinical trial registration information—Omega-3 Fatty Acids for Hyperactivity Treatment in Autism Spectrum Disorder; http://clinicaltrials.gov; NCT01694667. PMID:24839884

Dietary omega-3 PUFA and health: stearidonic acid-containing seed oils as effective and sustainable alternatives to traditional marine oils.

PubMed

Surette, Marc E

2013-05-01

The daily consumption of dietary omega-3 PUFA is recommended by governmental agencies in several countries and by a number of health organizations. The molecular mechanisms by which these dietary PUFA affect health involve the enrichment of cellular membranes with long-chain 20- and 22-carbon omega-3 PUFA that impacts tissues by altering membrane protein functions, cell signaling, and gene expression profiles. These changes are recognized to have health benefits in humans, especially relating to cardiovascular outcomes. Cellular membrane enrichment and health benefits are associated with the consumption of long-chain omega-3 PUFA found in marine oils, but are not generally linked with the consumption of alpha-linolenic acid, the 18-carbon omega-3 PUFA found in plant seed oils. However, the supply of omega-3 PUFA from marine sources is limited and may not be sustainable. New plant-derived sources of omega-3 PUFA like stearidonic acid-soy oil from genetically modified soybeans and Ahiflower oil from Buglossoides arvensis seeds that are enriched in the 18-carbon omega-3 PUFA stearidonic acid are being developed and show promise to become effective as well as sustainable sources of omega-3 PUFA. An example of changes in tissue lipid profiles associated with the consumption of Ahiflower oil is presented in a mouse feeding study. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Antioxidant properties of ferulic acid and its related compounds.

PubMed

Kikuzaki, Hiroe; Hisamoto, Masashi; Hirose, Kanae; Akiyama, Kayo; Taniguchi, Hisaji

2002-03-27

Antioxidant activity of 24 ferulic acid related compounds together with 6 gallic acid related compounds was evaluated using several different physical systems as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) decreased in the order caffeic acid > sinapic acid > ferulic acid > ferulic acid esters > p-coumaric acid. In bulk methyl linoleate, test hydroxycinnamic acids and ferulic acid esters showed antioxidant activity in parallel with their radical scavenging activity. In an ethanol-buffer solution of linoleic acid, the activity of test compounds was not always associated with their radical scavenging activity. Ferulic acid was most effective among the tested phenolic acids. Esterification of ferulic acid resulted in increasing activity. The activity of alkyl ferulates was somewhat influenced by the chain length of alcohol moiety. When the inhibitory effects of alkyl ferulates against oxidation of liposome induced by AAPH were tested, hexyl, octyl, and 2-ethyl-1-hexyl ferulates were more active than the other alkyl ferulates. Furthermore, lauryl gallate is most effective among the tested alkyl gallates. These results indicated that not only the radical scavenging activity of antioxidants, but also their affinity with lipid substrates, might be important factors in their activity.

[Electricity generation and contaminants degradation performances of a microbial fuel cell fed with Dioscorea zingiberensis wastewater].

PubMed

Li, Hui; Zhu, Xiu-Ping; Xu, Nan; Ni, Jin-Ren

2011-01-01

The electricity generation performance of a microbial fuel cell (MFC) utilizing Dioscorea zingiberensis wastewater was studied with an H-shape reactor. Indexes including pH, conductivity, oxidation peak potential and chemical oxygen demand (COD) of the anolyte were monitored to investigate the contaminants degradation performance of the MFC during the electricity generation process, besides, contaminant ingredients in anodic influent and effluent were analyzed by GC-MS and IR spectra as well. The maximum power density of the MFC could achieve 118.1 mW/m2 and the internal resistance was about 480 omega. Connected with a 1 000 omega external resistance, the output potential was about 0.4 V. Fed with 5 mL Dioscorea zingiberensis wastewater, the electricity generation lasted about 133 h and the coulombic efficiency was about 3.93%. At the end of electricity generation cycle, COD decreased by 90.1% while NH4(+) -N decreased by 66.8%. Furfural compounds, phenols and some other complicated organics could be decomposed and utilized in the electricity generation process, and the residual contaminants in effluent included some long-chain fatty acids, esters, ethers, and esters with benzene ring, cycloalkanes, cycloolefins, etc. The results indicate that MFC, which can degrade and utilize the organic contaminants in Dioscorea zingiberensis wastewater simultaneously, provides a new approach for resource recovery treatment of Dioscorea zingiberensis wastewater.