OZONOLYSIS OF UNSATURATED FATTY ACIDS: I. OZONOLYSIS OF OLEIC ACID

1961 ◽  
Vol 39 (10) ◽  
pp. 1956-1963 ◽  
Author(s):  
R. G. Ackman ◽  
M. E. Retson ◽  
L. R. Gallay ◽  
F. A. Vandenheuvel
Keyword(s):  
Hydrogen Peroxide ◽  
Fatty Acids ◽  
Oleic Acid ◽  
Formic Acid ◽  
Unsaturated Fatty Acids ◽  
Fission Products ◽  
Dicarboxylic Acids ◽  
Total Recovery ◽  
Subsequent Decomposition ◽  
By Products

Ozonolysis of oleic acid in methanol, a reacting solvent, with subsequent decomposition of the ozonide products by hydrogen peroxide in formic acid, gives yields of principal dicarboxylic acid fission products exceeding 95% with a minimum of secondary acidic products. The method is highly reproducible and offers unique advantages in the total recovery of the dicarboxylic acids and the elimination of peroxidic materials. The principal non-acidic by-products were tentatively identified as the Cs alcohols and their formyl esters.

scholarly journals Inhibition of steroid 5α-reductase by specific aliphatic unsaturated fatty acids

1992 ◽  
Vol 285 (2) ◽  
pp. 557-562 ◽  
Author(s):  
T Liang ◽  
S Liao
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Unsaturated Fatty Acids ◽  
Binding Assay ◽  
Reductase Activity ◽  
Undecylenic Acid ◽  
Gamma Linolenic Acid ◽  
Enzymic Assay

Human or rat microsomal 5 alpha-reductase activity, as measured by enzymic conversion of testosterone into 5 alpha-dihydrotestosterone or by binding of a competitive inhibitor, [3H]17 beta-NN-diethulcarbamoyl-4-methyl-4-aza-5 alpha-androstan-3-one ([3H]4-MA) to the reductase, is inhibited by low concentrations (less than 10 microM) of certain polyunsaturated fatty acids. The relative inhibitory potencies of unsaturated fatty acids are, in decreasing order: gamma-linolenic acid greater than cis-4,7,10,13,16,19-docosahexaenoic acid = cis-6,9,12,15-octatetraenoic acid = arachidonic acid = alpha-linolenic acid greater than linoleic acid greater than palmitoleic acid greater than oleic acid greater than myristoleic acid. Other unsaturated fatty acids such as undecylenic acid, erucic acid and nervonic acid, are inactive. The methyl esters and alcohol analogues of these compounds, glycerols, phospholipids, saturated fatty acids, retinoids and carotenes were inactive even at 0.2 mM. The results of the binding assay and the enzymic assay correlated well except for elaidic acid and linolelaidic acid, the trans isomers of oleic acid and linoleic acid respectively, which were much less active than their cis isomers in the binding assay but were as potent in the enzymic assay. gamma-Linolenic acid had no effect on the activities of two other rat liver microsomal enzymes: NADH:menadione reductase and glucuronosyl transferase. gamma-Linolenic acid, the most potent inhibitor tested, decreased the Vmax. and increased Km values of substrates, NADPH and testosterone, and promoted dissociation of [3H]4-MA from the microsomal reductase. gamma-Linolenic acid, but not the corresponding saturated fatty acid (stearic acid), inhibited the 5 alpha-reductase activity, but not the 17 beta-dehydrogenase activity, of human prostate cancer cells in culture. These results suggest that unsaturated fatty acids may play an important role in regulating androgen action in target cells.

scholarly journals Antioxidant and fatty acid profile of gabiroba seed (Campomanesisa Xanthocarpa Berg)

2012 ◽  
Vol 32 (2) ◽  
pp. 234-238 ◽  
Author(s):  
Marli da Silva Santos ◽  
Obdulio Gomes Miguel ◽  
Carmen Lúcia Oliveira Petkowicz ◽  
Lys Mary Bileski Cândido
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Fatty Acid Profile ◽  
Unsaturated Fatty Acids ◽  
Ethanol Extract ◽  
Solvent Polarity ◽  
Antioxidant Potential ◽  
Total Phenolic ◽  
Total Phenolic Compounds

This study aimed to evaluate the antioxidant potential and fatty acid profile of gabiroba (Campomanesia xanthocarpa Berg) seeds. In order to obtain the extract, the seeds were dried, crushed, and subjected to sequential extraction by maceration and percolation in a modified soxhlet extractor using solvent polarity gradient composed of hexane, chloroform, ethyl acetate, and alcohol, respectively. The extraction time was six hours. The ethanol extract showed the highest antioxidant potential, given by the EC50 value and the amount of total phenolic compounds. High amounts of unsaturated fatty acids were found in the oil studied, especially the oleic acid.

scholarly journals Bioprocessing of Shrimp Waste Using Novel Industrial By-Products: Effects on Nutrients and Lipophilic Antioxidants

Fermentation ◽  
2021 ◽  
Vol 7 (4) ◽  
pp. 312
Author(s):  
Luis Angel Cabanillas-Bojórquez ◽  
Erick Paul Gutiérrez-Grijalva ◽  
Ramón Ignacio Castillo-López ◽  
Laura Aracely Contreras-Angulo ◽  
Miguel Angel Angulo-Escalante ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
Rich Source ◽  
Added Value ◽  
The Novel ◽  
Shrimp Waste ◽  
Acid Fermentation ◽  
Trolox Equivalent ◽  
By Products

The production of marine foods is on the rise, and shrimp is one of the most widely consumed. As a result, a considerable amount of shrimp waste is generated, becoming a hazardous problem. Shrimp waste is a rich source of added-value components such as proteins, lipids, chitin, minerals, and carotenoids; however, new bioprocesses are needed to obtain these components. This work aimed to characterize the chemical and nutraceutical constituents from the liquor of shrimp waste recovered during a lactic acid fermentation process using the novel substrate sources whey and molasses. Our results showed that the lyophilized liquor is a rich source of proteins (25.40 ± 0.67%), carbohydrates (38.92 ± 0.19%), minerals (calcium and potassium), saturated fatty acids (palmitic, stearic, myristic and lauric acids), unsaturated fatty acids (oleic acid, linoleic, and palmitoleic acids), and astaxanthin (0.50 ± 0.02 µg astaxanthin/g). Moreover, fermentation is a bioprocess that allowed us to obtain antioxidants such as carotenoids with an antioxidant capacity of 154.43 ± 4.73 µM Trolox equivalent/g evaluated by the ABTS method. Our study showed that liquor from shrimp waste fermentation could be a source of nutraceutical constituents with pharmaceutical applications. However, further studies are needed to separate these added-value components from the liquor matrix.

scholarly journals Effect of nitrogen and potassium fertilization on the production and quality of oil in Jatropha curcas L. under the dry and warm climate conditions of Colombia

2014 ◽  
Vol 32 (2) ◽  
pp. 255-265 ◽  
Author(s):  
Omar Montenegro R. ◽  
Stanislav Magnitskiy ◽  
Martha C. Henao T.
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Jatropha Curcas ◽  
Oil Content ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
Fruit Production ◽  
Biodiesel Production ◽  
Oil Composition

This study was conducted to assess fruit and seed yield, oil content and oil composition of Jatropha curcas fertilized with different doses of nitrogen and potassium in Espinal (Tolima, Colombia). The yields ranged from 4,570 to 8,800 kg ha-1 of fruits and from 2,430 to 4,746 kg ha-1 of seeds. These yields showed that the fertilizer dose of 150 kg ha-1 N + 120 kg ha-1K increased fruit production by 92% and seed production by 95%, which represents an increase of about 100% in oil production, which increased from 947 to 1,900 kg ha-1. The total oil content in the seeds ranged from 38.7 to 40.1% (w/w) with a high content of the unsaturated fatty acids oleic (> 47%) and linoleic acid (> 29%). The highest content of oleic acid in the seed oil was from the unfertilized control plants and plants with an application of 100 kg ha-1 of N and 60 kg ha-1 of K, with an average of 48%. The lowest content of oleic acid was registered when a low dose of nitrogen and a high level of potassium were applied at a ratio of 1:2.4 and doses of 50 kg ha-1 N + 120 kg ha-1 K, respectively. Low contents of the saturated fatty acids palmitic (13.4%) and stearic (7.26%) were obtained, making this oil suitable for biodiesel production. The nitrogen was a more important nutrient for the production and quality of oil in J. curcas than potassium under the studied conditions of soil and climate.

scholarly journals Antagonism Between Saturated and Unsaturated Fatty Acids in ROS Mediated Lipotoxicity in Rat Insulin-Producing Cells

2015 ◽  
Vol 36 (3) ◽  
pp. 852-865 ◽  
Author(s):  
Wiebke Gehrmann ◽  
Wiebke Würdemann ◽  
Thomas Plötz ◽  
Anne Jörns ◽  
Sigurd Lenzen ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Palmitic Acid ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
H2o2 Production ◽  
Β Cell ◽  
Specific Expression ◽  
Insulin Producing Cells ◽  
H2o2 Formation

Background/Aims: Elevated levels of non-esterified fatty acids (NEFAs) are under suspicion to mediate β-cell dysfunction and β-cell loss in type 2 diabetes, a phenomenon known as lipotoxicity. Whereas saturated fatty acids show a strong cytotoxic effect upon insulin-producing cells, unsaturated fatty acids are not toxic and can even prevent toxicity. Experimental evidence suggests that oxidative stress mediates lipotoxicity and there is evidence that the subcellular site of ROS formation is the peroxisome. However, the interaction between unsaturated and saturated NEFAs in this process is unclear. Methods: Toxicity of rat insulin-producing cells after NEFA incubation was measured by MTT and caspase assays. NEFA induced H2O2 formation was quantified by organelle specific expression of the H2O2 specific fluorescence sensor protein HyPer. Results: The saturated NEFA palmitic acid had a significant toxic effect on the viability of rat insulin-producing cells. Unsaturated NEFAs with carbon chain lengths >14 showed, irrespective of the number of double bonds, a pronounced protection against palmitic acid induced toxicity. Palmitic acid induced H2O2 formation in the peroxisomes of insulin-producing cells. Oleic acid incubation led to lipid droplet formation, but in contrast to palmitic acid induced neither an ER stress response nor peroxisomal H2O2 generation. Furthermore, oleic acid prevented palmitic acid induced H2O2 production in the peroxisomes. Conclusion: Thus unsaturated NEFAs prevent deleterious hydrogen peroxide generation during peroxisomal β-oxidation of long-chain saturated NEFAs in rat insulin-producing cells.

ERUCIC ACID AND CHOLESTEROL EXCRETION IN THE RAT

1956 ◽  
Vol 34 (1) ◽  
pp. 981-991 ◽  
Author(s):  
K. K. Carroll ◽  
R. L. Noble
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Erucic Acid ◽  
Unsaturated Fatty Acids ◽  
Fatty Acid Fraction ◽  
Cholesterol Concentration ◽  
Acid Fraction ◽  
Cholesterol Excretion ◽  
Fecal Cholesterol

Erucic acid has been found to increase the excretion of endogenously produced cholesterol in the rat with little change in the cholesterol concentration in the carcass except for increased concentrations in the adrenals and liver. The fecal cholesterol was identified by melting point and infrared spectrum after isolation by chromatography on alumina. It does not appear to originate in the liver since no increase was observed in the biliary excretion of cholesterol. Other homologues of oleic acid, namely eicosenoic and nervonic acid, produced similar changes in fecal cholesterol excretion, although oleic acid itself had little effect. A series of saturated fatty acids from butyric (C4) to behenic (C22) were tested and the longer chain members found to cause some increase in cholesterol excretion. Ester cholesterol accounted for much of the observed increases but varied greatly in the experiments with unsaturated fatty acids. A preparation of cerebrosides from beef spinal cord also increased the amount of cholesterol excreted in the feces. The fatty acid fraction from this preparation gave a similar result, although the cerebrosides gave rise mainly to free cholesterol and the fatty acid fraction to ester cholesterol.

scholarly journals S-acylation modulates the function of the apical sodium-dependent bile acid transporter in human cells

2020 ◽  
Vol 295 (14) ◽  
pp. 4488-4497 ◽  
Author(s):  
Alexander L. Ticho ◽  
Pooja Malhotra ◽  
Christopher R. Manzella ◽  
Pradeep K. Dudeja ◽  
Seema Saksena ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Bile Acid ◽  
Palmitic Acid ◽  
Unsaturated Fatty Acids ◽  
Hek293 Cells ◽  
Metabolic Labeling ◽  
Sodium Dependent ◽  
Bile Acid Transporter ◽  
Acid Transporter

The ileal apical sodium-dependent bile acid transporter (ASBT) is crucial for the enterohepatic circulation of bile acids. ASBT function is rapidly regulated by several posttranslational modifications. One reversible posttranslational modification is S-acylation, involving the covalent attachment of fatty acids to cysteine residues in proteins. However, whether S-acylation affects ASBT function and membrane expression has not been determined. Using the acyl resin-assisted capture method, we found that the majority of ASBT (∼80%) was S-acylated in ileal brush border membrane vesicles from human organ donors, as well as in HEK293 cells stably transfected with ASBT (2BT cells). Metabolic labeling with alkyne–palmitic acid (100 μm for 15 h) also showed that ASBT is S-acylated in 2BT cells. Incubation with the acyltransferase inhibitor 2-bromopalmitate (25 μm for 15 h) significantly reduced ASBT S-acylation, function, and levels on the plasma membrane. Treatment of 2BT cells with saturated palmitic acid (100 μm for 15 h) increased ASBT function, whereas treatment with unsaturated oleic acid significantly reduced ASBT function. Metabolic labeling with alkyne–oleic acid (100 μm for 15 h) revealed that oleic acid attaches to ASBT, suggesting that unsaturated fatty acids may decrease ASBT's function via a direct covalent interaction with ASBT. We also identified Cys-314 as a potential S-acylation site. In conclusion, these results provide evidence that S-acylation is involved in the modulation of ASBT function. These findings underscore the potential for unsaturated fatty acids to reduce ASBT function, which may be useful in disorders in which bile acid toxicity is implicated.

Potential Use of Tuna (Thunnus albacares) by-product: Production of Antioxidant Peptides and Recovery of Unsaturated Fatty Acids from Tuna Head

2017 ◽  
Vol 13 (7) ◽  
Author(s):  
Dayse Oliveira ◽  
Daniela Bernardi ◽  
Fernanda Drummond ◽  
Fabiana Dieterich ◽  
Wilson Boscolo ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Antioxidant Capacity ◽  
Unsaturated Fatty Acids ◽  
Protein Hydrolysate ◽  
Trolox Equivalent Antioxidant Capacity ◽  
Total Amino Acid ◽  
Degree Of Hydrolysis ◽  
Antioxidant Peptides ◽  
Antioxidant Power ◽  
By Products

AbstractTuna by-products were subjected to enzymatic hydrolysis with Alcalase (enzyme to substrate ratio 1 : 200 w/w; 60 °C; pH 6.5, 120 min) rendering a tuna protein hydrolysate (TPH) with 9.24 % degree of hydrolysis (DH). The antioxidant capacity of TPH determined by the methods of ferric reducing antioxidant power (FRAP) and Trolox equivalent antioxidant capacity (TEAC) were similar and 10 times lower than the result obtained by oxygen radical absorbance capacity (ORAC). The total amino acid profile indicated that 42.15 % are composed of hydrophobic amino acids and 7.7 % of aromatics, with leucine being found in the highest quantity (17.85 %). The fatty acid profile of the oil recovered by centrifugation of the TPH – as determined by a gas chromatograph – was characterized by a high percentage of polyunsaturated fatty acids (PUFAs) (39.06 %), mainly represented by the fatty acids ω3, docosahexaenoic acid (27.15 %) and eicosapentaenoic acid (6.05 %). The simultaneous recovery of unsaturated fatty acids and antioxidant peptides can add value to tuna by-products, assisting in the efficient management of fishing industry waste.

Identification of acrolein from the ozone oxidation of unsaturated fatty acids

1999 ◽  
Vol 18 (11) ◽  
pp. 677-682 ◽  
Author(s):  
R Medina-Navarro ◽  
E Mercado-Pichardo ◽  
O Herńndez-Pérez ◽  
J J Hicks
Keyword(s):  
Fatty Acids ◽  
Unsaturated Fatty Acids ◽  
Biological Systems ◽  
Thiobarbituric Acid ◽  
Environmental Pollutant ◽  
Fused Silica ◽  
Erythrocyte Membranes ◽  
Human Erythrocyte Membranes ◽  
Dependent Form ◽  
By Products

By-products of lipoperoxidation reactions may be associated with the genesis or the progression of several diseases as arteriosclerosis, diabetes and cancer, among many others. Acrolein, at first a widely distributed environmental pollutant, is currently known as a compound capable of being generated as a result of metabolic reactions within biological systems, highly toxic and the most electrophilic of the a, b-unsaturated aldehydes formed during lipoperoxidation. In the present study: 1 The separation of acrolein and malondialdehyde was achieved at alkaline pH with the use of high voltage capillary electrophoresis in uncoated fused-silica capillaries. 2 It was demonstrated how the oxidation of fatty acids (arachidonic/linoleic) with ozone generates, in dose-dependent form, acrolein as one of the by-products of the lipoperoxidation process. The oxidation of open human erythrocyte membranes with ozone also generated acrolein. 3 After aldolic condensation, aldol-acrolein derivative has a positive reaction with 2-thiobarbituric acid (TBA) and shows a maximum absorption at 498 nm. This novel characteristic is used in its identification after the separation of the by-products. 4 It is possible to suggest that in the classic reaction of the denominated thiobarbituric acid reactive substances (TBARS), when used as an indicator of the degree of peroxidation in biological systems, a portion of acrolein could be present but dwarfed by the TBAMDA adduct.

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