scholarly journals Regioselective and Stereoselective Epoxidation of n-3 and n-6 Fatty Acids by Fungal Peroxygenases

Antioxidants ◽  
2021 ◽  
Vol 10 (12) ◽  
pp. 1888
Author(s):  
Alejandro González-Benjumea ◽  
Dolores Linde ◽  
Juan Carro ◽  
René Ullrich ◽  
Martin Hofrichter ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Double Bond ◽  
Chemical Synthesis ◽  
Polyunsaturated Fatty Acids ◽  
Chiral Hplc ◽  
Pharmacological Activities ◽  
Racemic Mixtures ◽  
Synthetic Utility ◽  
Stereoselective Epoxidation

Epoxide metabolites from n-3 and n-6 polyunsaturated fatty acids arouse interest thanks to their physiological and pharmacological activities. Their chemical synthesis has significant drawbacks, and enzymes emerge as an alternative with potentially higher selectivity and greener nature. Conversion of eleven eicosanoid, docosanoid, and other n-3/n-6 fatty acids into mono-epoxides by fungal unspecific peroxygenases (UPOs) is investigated, with emphasis on the Agrocybe aegerita (AaeUPO) and Collariella virescens (rCviUPO) enzymes. GC-MS revealed the strict regioselectivity of the n-3 and n-6 reactions with AaeUPO and rCviUPO, respectively, yielding 91%-quantitative conversion into mono-epoxides at the last double bond. Then, six of these mono-epoxides were obtained at mg-scale, purified and further structurally characterized by 1H, 13C and HMBC NMR. Moreover, chiral HPLC showed that the n-3 epoxides were also formed (by AaeUPO) with total S/R enantioselectivity (ee > 99%) while the n-6 epoxides (from rCviUPO reactions) were formed in nearly racemic mixtures. The high regio- and enantioselectivity of several of these reactions unveils the synthetic utility of fungal peroxygenases in fatty acid epoxidation.

scholarly journals Stereoselective epoxidation of the last double bond of polyunsaturated fatty acids by human cytochromes P450

2009 ◽  
Vol 51 (5) ◽  
pp. 1125-1133 ◽  
Author(s):  
Danièle Lucas ◽  
Sophie Goulitquer ◽  
Jan Marienhagen ◽  
Maude Fer ◽  
Yvonne Dreano ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Double Bond ◽  
Polyunsaturated Fatty Acids ◽  
Cytochromes P450 ◽  
Stereoselective Epoxidation

scholarly journals Fatty acid profiles of muscle, liver, heart and kidney of Australian prime lambs fed different polyunsaturated fatty acids enriched pellets in a feedlot system

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Hung Van Le ◽  
Don Viet Nguyen ◽  
Quang Vu Nguyen ◽  
Bunmi Sherifat Malau-Aduli ◽  
Peter David Nichols ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Fatty Acid Profiles

Growth and carcass characteristics of three lamb genotypes finished on the same level of feeding

2000 ◽  
Vol 70 (1) ◽  
pp. 51-61 ◽  
Author(s):  
L. O. W. McClintont ◽  
A. F. Carson
Keyword(s):  
Fatty Acids ◽  
Body Weight ◽  
Fatty Acid ◽  
Weight Gain ◽  
Polyunsaturated Fatty Acids ◽  
Body Weight Gain ◽  
Saturated Fatty Acids ◽  
Carcass Characteristics ◽  
Live Weight ◽  
Ash Content

AbstractThis study investigated the efficiency of growth and the carcass characteristics of 24 Greyface (Border Leicester × Scottish Blackface), 24 Texel (12 purebred and 12 Texel × Texel-Greyface) and 24 Rouge (12 purebred and 12 Rouge × Rouge-Greyface) lambs finished on the same level of feeding. The efficiency of live-weight gain (kg/MJ) was higher in Greyface compared with Texel lambs (P< 0·01). The efficiency of empty body-weight gain (kg/MJ) was higher in Greyface (P< 0·01) and Rouge (P< 0·05) compared with Texel lambs. The efficiency of carcass gains (kg/MJ) tended to be higher in Greyface and Rouge compared with Texel lambs (P= 0·07). The efficiency of non-carcass component gains (kg/MJ) was also higher in Greyface compared with Texel lambs (P0·05). Carcass water, protein, lipid and ash gains did not vary significantly between the genotypes, however carcass energy gain tended to be higher in Greyface and Rouge compared with Texel lambs (P= 0·08). The relative proportions of water, protein, lipid and ash in carcass gains did not vary significantly between the genotypes. At the end of the experiment carcass water content was higher in Texel compared with Greyface lambs (P< 0·05) and carcass ash content was lower in Texel compared with Greyface (P< 0·01) and Rouge (P< 0·05) lambs. The concentration of saturated fatty acids was higher in Greyface compared with Rouge lambs (P< 0·001) and higher in Rouge compared with Texel lambs (P< 0·05). Monounsaturated fatty acid concentrations were higher in Rouge compared with Greyface lambs (P< 0·05) and higher in Texel compared with Rouge lambs (P< 0·001). Polyunsaturated fatty acid concentrations were higher in Rouge and Texel compared with Greyface lambs (P< 0·01). The ratio of n-6:n-3 fatty acids was lower in Rouge compared with Greyface lambs (P< 0·05).The efficiency of empty body gain was higher in male compared with female lambs (P< 0·05). Carcass water (P< 0·01) and protein (P< 0·05) gains were higher in male lambs. At the end of the experiment male carcasses contained a higher content of water (P< 0·05), protein (P< 0·01) and ash (P= 0·07), and a lower lipid (P< 0·05) and energy (P< 0·001) content. Carcass lipids from male lambs contained a higher concentration of polyunsaturated fatty acids (P< 0·001) and tended to contain a lower concentration of saturated fatty acids (P = 0·06).

Long-chain n-3 polyunsaturated fatty acids contained in liver and muscle tissues of Okinawan long-spine porcupinefish (Diodon holocanthus Linnaeus 1758)

2021 ◽  
Vol ahead-of-print (ahead-of-print) ◽  
Author(s):  
Yutaka Tashiro
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Ryukyu Islands ◽  
Okinawa Island ◽  
Content Type ◽  
Muscle Tissues ◽  
The Ryukyu Islands ◽  
Total Fatty Acids ◽  
Long Chain

Purpose This study aimed to analyze the lipid content and fatty acid composition in the liver and muscle of a porcupinefish species inhabiting waters around the Ryukyu Islands to investigate their potential as a source of long-chain n-3 polyunsaturated fatty acids (LC-PUFAs). Design/methodology/approach Porcupinefish were collected along the Okinawa Island coast. The composition of fatty acids and cholesterol in both liver and muscle were analyzed using a gas chromatograph mass spectrometer. Findings The liver of Okinawan long-spine porcupinefish was rich in lipids whose content correlated to the proportion of liver/body weight. Fatty acid compositions in their liver and muscles were similar to each other. LC-PUFAs occupied 44% of total fatty acids, with docosahexaenoic acid (DHA) being the dominant (42%), whereas eicosapentaenoic acid occupied 2.4%. The liver contained 1,690 mg of cholesterol and 14.8 g of DHA per 100 g, whose proportion decreased in summer compared to other seasons (p = 0.036). Originality/value The liver of Okinawan long-spine porcupinefish, which has not yet been commercially used although its non-toxicity is claimed, can be an excellent source of LC-PUFAs, especially DHA, accentuating its potential in food supplements’ production.

Maternal polyunsaturated fatty acids and risk for autism spectrum disorder in the MARBLES high-risk study

Autism ◽  
2020 ◽  
Vol 24 (5) ◽  
pp. 1191-1200 ◽  
Author(s):  
Yunru Huang ◽  
Ana-Maria Iosif ◽  
Robin L Hansen ◽  
Rebecca J Schmidt
Keyword(s):  
Autism Spectrum Disorder ◽  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Polyunsaturated Fatty Acid ◽  
Autism Spectrum ◽  
Spectrum Disorder ◽  
Fatty Acid Intake ◽  
Third Trimester ◽  
Acid Intake

Prior research studies suggest that maternal polyunsaturated fatty acids could have protective effects on neurodevelopmental outcomes. The objective of this study was to examine associations between maternal polyunsaturated fatty acid intake during pregnancy and risk for autism spectrum disorder and other non-typical development in a prospective cohort. Eligible women already had a child with autism spectrum disorder and were planning a pregnancy or were pregnant with another child. Children were clinically assessed longitudinally and diagnosed at 36 months. Maternal polyunsaturated fatty acid intake during pregnancy was estimated using food frequency questionnaires. Maternal third-trimester plasma polyunsaturated fatty acid concentration was measured by gas chromatography. In all, 258 mother–child pairs were included. Mothers consuming more total omega-3 in the second half of pregnancy were 40% less likely to have children with autism spectrum disorder (relative risk = 0.6, 95% confidence interval: 0.3–0.98). No significant associations were observed between maternal third-trimester plasma polyunsaturated fatty acid subtype concentrations and risk of autism spectrum disorder. However, higher plasma eicosapentaenoic acid and docosahexaenoic acid concentrations were associated with lower non-typical development risk (relative risk ranging from 0.47 to 0.88). This study provides suggestive evidence of associations between risk of autism spectrum disorder in the children and maternal omega-3 intake in late pregnancy but not with third-trimester plasma polyunsaturated fatty acids. Further research is needed to evaluate these potential relationships. Lay abstract Prior studies suggest that maternal polyunsaturated fatty acids intake during pregnancy may have protective effects on autism spectrum disorder in their children. However, they did not examine detailed timing of maternal polyunsaturated fatty acid intake during pregnancy, nor did they evaluate plasma concentrations. This study investigates whether maternal polyunsaturated fatty acids in defined time windows of pregnancy, assessed by both questionnaires and biomarkers, are associated with risk of autism spectrum disorder and other non-typical development in the children. Food frequency questionnaires were used to estimate maternal polyunsaturated fatty acid intake during the first and second half of pregnancy. Gas chromatography measured maternal plasma polyunsaturated fatty acid concentrations in the third trimester. In all, 258 mother–child pairs from a prospective cohort were included. All mothers already had a child with autism spectrum disorder and were planning a pregnancy or pregnant with another child. Children were clinically assessed longitudinally and diagnosed at 36 months. For polyunsaturated fatty acid intake from questionnaires, we only found mothers consuming more omega-3 in the second half of pregnancy were 40% less likely to have children with autism spectrum disorder. For polyunsaturated fatty acid concentrations in the third-trimester plasma, we did not observe any statistical significance in relation to the risk of autism spectrum disorder. However, our study confirmed associations from previous studies between higher maternal docosahexaenoic acid and eicosapentaenoic acid plasma concentrations in the late pregnancy and reduced risk for non-typical development. This study markedly advanced understandings of whether and when maternal polyunsaturated fatty acid intake influences risk for autism spectrum disorder and sets the stage for prevention at the behavioral and educational level.

scholarly journals Effect of storage on fatty acid profile of butter from cows fed whole or ground flaxseed with or without monensin

2010 ◽  
Vol 39 (10) ◽  
pp. 2297-2303 ◽  
Author(s):  
Daniele Cristina da Silva-Kazama ◽  
Geraldo Tadeu dos Santos ◽  
Paula Toshimi Matumoto Pintro ◽  
Jesuí Vergílio Visentainer ◽  
Ricardo Kazama ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acids ◽  
Fatty Acid Profile ◽  
Saturated Fatty Acids ◽  
Relative Percentage ◽  
Medium Chain ◽  
Medium Chain Fatty Acids ◽  
Ground Flaxseed ◽  
Chain Fatty Acids

Eight Holstein cows with body weight 570 ± 43 kg and 60 ± 20 lactation days were distributed in a double Latin square design with four 21-day periods to determine the effects of feeding ground or whole flaxseed with or without monensin supplementation (0.02% on a dry matter basis) on fatty acid profile of butter stored for 15 and 45 days. Ground flaxseed supply, in comparison to whole flaxseed, reduced relative percentages of 16:0, cis7-16:1, 17:0, and cis10-17:1 but it increased those of cis9,trans11-18:2, cis3-18:3, and omega 3 fatty acids in butter fat, reducing relative percentage of medium-chain fatty acids and increasing the content of polyunsaturated fatty acids. Supplementation with monensin increased relative percentages of cis9,trans11-18:2 and tended to increase relative percentage of 17:0 and decrease that of saturated fatty acids in butter. Butter from cows fed diet with monensin presented lower relative percentages of cis 6-20:4. Relative percentages of cis 9-16:1, cis10-17:1, 18:0, trans11-18:1, cis9-18:1, cis3-18:3, cis6-20:4 in butter stored for 15 days were higher than those stored for 45 days and the relative percentages of cis3-20:5 tended to decrease with the increase of storage period. As a result, relative percentages of saturated fatty acids and medium-chain fatty acids increased with storage time, while those of monounsaturated and long-chain fatty acids decreased. Butter enriched with polyunsaturated fatty acids may have a shorter shelf life due to the negative effect of storage on fatty acid profile which may cause oxidation and rancidity.

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