scholarly journals Bis(monoacylglycerol) phosphate in rat uterine stromal cells: structural characterization and specific esterification of docosahexaenoic acid

2000 ◽  
Vol 351 (3) ◽  
pp. 795-804 ◽  
Author(s):  
Céline LUQUAIN ◽  
René DOLMAZON ◽  
Jean-Marie ENDERLIN ◽  
Christian LAUGIER ◽  
Michel LAGARDE ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Stromal Cells ◽  
Total Phospholipid ◽  
Acyl Chain ◽  
Primary Alcohol ◽  
High Specificity ◽  
Acyl Chains ◽  
Two Peaks

In rat uterine stromal cells (UIII cells), docosahexaenoic acid (DHA) was esterified extensively in alkenylacyl-glycerophosphoethanolamine and in an unknown phospholipid accounting for only 0.7% of the total phospholipid. The latter was identified as a bis(monoacylglycerol) phosphate (BMP) using MS. Incorporation studies using C18:3n-3 and C20:5n-3 demonstrated that BMP had a high specificity to incorporate DHA and C22 polyunsaturated fatty acids of the (n-3) series. By contrast, polyunsaturated fatty acids of the (n-6) series were never incorporated into BMP. Incubation of UIII cells with 5µM DHA for 24h increased the DHA content of BMP from 36 to 71% of the total acyl chains. [3H]DHA-labelled BMP purified as a single TLC spot was resolved into three peaks using HPLC. These peaks were also observed when cells were labelled with [3H]phosphatidylglycerol, an exogenous BMP precursor, and with [33P]Pi. Electrospray MS of BMP from control cells showed that the first two peaks contained the same molecular species (mainly C22:6n-3/C22:6n-3 and C18:1n-9/C22:6n-3) while the third peak mainly contained the C18:1n-9/C18:1n-9 species. The stereoconfiguration analysis of the compounds revealed an sn-glycero-3-phospho-1′-sn-glycerol configuration for the first peak and sn-glycero-1-phospho-1′-sn-glycerol configurations for the other two. BMP from rat testis was used to establish the positions of the acyl groups. More than 70% of its acyl chains were C22:5n-6. It was separated on HPLC into three peaks that co-migrated with the three peaks of BMP from UIII cells. Lipase activity and NMR analysis of the second peak showed that fatty acids esterified the primary alcohol group on each glycerol moiety. We conclude that the three peaks are stereoisomeric compounds with different acyl-chain locations and may be the result of different metabolic fates depending on subcellular localization.

DHA-enriched phospholipids from large yellow croaker roe regulate lipid metabolic disorders and gut microbiota imbalance on SD rats with a high-fat diet

2021 ◽  
Author(s):  
Xiaodan Lu ◽  
Rongbin Zhong ◽  
Ling Hu ◽  
Luyao Huang ◽  
Lijiao Chen ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Gut Microbiota ◽  
Polyunsaturated Fatty Acids ◽  
High Fat Diet ◽  
Nutritional Value ◽  
Metabolic Disorders ◽  
Large Yellow Croaker ◽  
High Fat ◽  
Sd Rats

Abstract Large yellow croaker roe phospholipids (LYCRPLs) has great nutritional value because of containing rich docosahexaenoic acid (DHA), which is a kind of n-3 polyunsaturated fatty acids (n-3 PUFAs). In...

scholarly journals Microalgae n-3 PUFAs Production and Use in Food and Feed Industries

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 113
Author(s):  
Marine Remize ◽  
Yves Brunel ◽  
Joana L. Silva ◽  
Jean-Yves Berthon ◽  
Edith Filaire
Keyword(s):  
Fatty Acids ◽  
Global Warming ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Eicosapentaenoic Acid ◽  
Human Health ◽  
Current Knowledge ◽  
Epa And Dha ◽  
Anti Cancer ◽  
Food And Feed

N-3 polyunsaturated fatty acids (n-3 PUFAs), and especially eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), are essential compounds for human health. They have been proven to act positively on a panel of diseases and have interesting anti-oxidative, anti-inflammatory or anti-cancer properties. For these reasons, they are receiving more and more attention in recent years, especially future food or feed development. EPA and DHA come mainly from marine sources like fish or seaweed. Unfortunately, due to global warming, these compounds are becoming scarce for humans because of overfishing and stock reduction. Although increasing in recent years, aquaculture appears insufficient to meet the increasing requirements of these healthy molecules for humans. One alternative resides in the cultivation of microalgae, the initial producers of EPA and DHA. They are also rich in biochemicals with interesting properties. After defining macro and microalgae, this review synthesizes the current knowledge on n-3 PUFAs regarding health benefits and the challenges surrounding their supply within the environmental context. Microalgae n-3 PUFA production is examined and its synthesis pathways are discussed. Finally, the use of EPA and DHA in food and feed is investigated. This work aims to define better the issues surrounding n-3 PUFA production and supply and the potential of microalgae as a sustainable source of compounds to enhance the food and feed of the future.

Lipase-catalyzed esterification of glycerol with n-3 polyunsaturated fatty acids from winterized fish oil Esterificación catalítica de glicerol con ácidos grasos 3-n poliinsaturados de aceite de pescado

1998 ◽  
Vol 4 (6) ◽  
pp. 401-405 ◽  
Author(s):  
V.J. Robles ◽  
H.S. García ◽  
J.A. Monroy ◽  
O. Angulo
Keyword(s):  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Eicosapentaenoic Acid ◽  
Phosphate Buffer ◽  
Esterification Reaction ◽  
Pseudomonas Sp ◽  
Menhaden Oil ◽  
Glyceride Synthesis ◽  
Esterified Fatty Acids

Menhaden oil was hydrolyzed using a lipase from Pseudomonas sp. The hydrolysate was cold frac tionated at-72°C. Glyceride synthesis was performed using the same lipase under different reaction environments. The best conditions for the esterification reaction were 39 °C for 18 h in a reaction mixture containing anhydrous glycerol, n-3 polyunsaturated fatty acids (PUFA) enriched solution (2% lipids in hexane), hexane, and phosphate buffer-lipase solution (1% w/v). Product composition was 81.33% triacylglycerides and 18.67% of free fatty acids (w/w). Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) accounted for 36.18% of the esterified fatty acids, of which 58% was EPA and 42% was DHA. This method offers an alternative to produce glycerides rich in n-3 PUFA.

Total Synthesis of DHA and DPAn-3 non-enzymatic oxylipins

Synthesis ◽  
2021 ◽  
Author(s):  
alexandre guy ◽  
Jérémy Merad ◽  
Thomas Degrange ◽  
Guillaume Reversat ◽  
Valérie Bultel-Poncé ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Total Synthesis ◽  
Biological Properties ◽  
Chemical Structures ◽  
Structural Variety ◽  
Synthetic Strategy

Oxylipins are formed in-vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentanes, tetrahydrofurans, hydroxylated-PUFA etc.). All structures of oxylipins are of great biological interests. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies and more especially, they were found to have their own biological properties. Produced in-vivo as a non-separable mixture of isomers, total synthesis is a keystone to answer biological questions. In this work, we described the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) using a unique and convergent synthetic strategy.

Uptake and interconversion of plasma unesterified n-3 polyunsaturated fatty acids by the GI tract of rats

1995 ◽  
Vol 268 (5) ◽  
pp. G732-G738
Author(s):  
A. Nilsson ◽  
W. Becker
Keyword(s):  
Fatty Acids ◽  
Small Intestine ◽  
Gastrointestinal Tract ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Gi Tract ◽  
Tissue Lipids ◽  
Blood Albumin

The origin of the linoleic [18:2(n-6)], arachidonic [20:4(n-6)], and docosahexaenoic acid [22:6(n-3)] of the mucosal phospholipids in the gastrointestinal (GI) tract is not known. This study examines whether stomach, small intestine, and colon take up and desaturate-elongate unesterified polyunsaturated fatty acids (PUFA) from blood. Albumin-bound unesterified alpha-[14C]linolenate [18:3(n-3)] and [3H]eicosapentaenoate [20:5(n-3)] were injected intravenously. After 10 min, 1 h, and 18 h, radioactivity of tissue lipids and the degree of interconversion of the 3H-labeled and 14C-labeled fatty acids were determined. After 10 min, the lipids of the gastrointestinal tract contained 3.6% of the 14C (0.5% in stomach, 2.7% in small intestine, and 0.4% in colon) and 4.9% of the 3H (0.6% in stomach, 3.6% in small intestine, and 0.7% in colon). Both fatty acids were acylated mainly into phospholipids, both in liver and gastrointestinal tract. Although the proportions of radioactivity found in desaturation-elongation products increased with time, 15% of the 14C in the liver, 6% in the stomach, 8% in the small intestine, and 11% in the colon were in 20:5 already after 10 min. A rapid interconversion of 18:3 thus occurred both in the liver and in the gastrointestinal tract. In all tissues examined, interconversion of [3H]20:5 to [3H]22:5 also occurred. Interconversion of unesterified PUFA taken up from blood may be an important source of eicosanoid precursors in the gastrointestinal tract.

scholarly journals Rapeseeds a Rich Source of Polyunsaturated Fatty Acids

Proceedings ◽  
2019 ◽  
Vol 29 (1) ◽  
pp. 115
Author(s):  
Cristina Emanuela Enăşcuţă ◽  
Elena Emilia Oprescu ◽  
Adrian Radu ◽  
Elena Radu ◽  
Marian Deaconu ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Docosahexaenoic Acid ◽  
Polyunsaturated Fatty Acids ◽  
Eicosapentaenoic Acid ◽  
Stroke Prevention ◽  
Essential Role ◽  
Omega 3 Fatty Acids ◽  
Omega 3 ◽  
Human Diet ◽  
Brain Functions

In human diet, polyunsaturated fatty acids (PUFA), have an essential role in optimal brain functions and stroke prevention, specially, omega-3 fatty acids, e.g., 9,12,15-linolenic acid (ALA, 18:3), 5,8,11,14,17-eicosapentaenoic acid (EPA, 20:5), and 4,7,10,13,16,19-docosahexaenoic acid (DHA, 22:6). [...]

Sign in / Sign up

Export Citation Format

Share Document