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.

scholarly journals History of Chemical Routes towards Cyclic Non-Enzymatic Oxygenated Metabolites of Polyunsaturated Fatty Acids

Synthesis ◽  
2018 ◽  
Vol 50 (17) ◽  
pp. 3257-3280 ◽  
Author(s):  
Camille Oger ◽  
Claire Cuyamendous ◽  
Aurélien de la Torre ◽  
Mathieu Candy ◽  
Alexandre Guy ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Free Radical ◽  
Polyunsaturated Fatty Acids ◽  
Total Synthesis ◽  
Scientific Community ◽  
Biological Properties ◽  
Biological Processes ◽  
Total Syntheses ◽  
History Of

Enzymatically formed oxygenated metabolites of polyunsaturated fatty acids (PUFA) are of great interest for the scientific community being mediators and biomarkers in the physiological and pathological regulation of many key biological processes. More recently; metabolites of PUFA formed through a non-enzymatic free radical pathway have gained interest in diseases linked with oxidative stress. Thus, synthetic strategies leading to the total synthesis of such metabolites are an essential field of research, and this review will cover a structural presentation, will discuss their biological interests, and present total syntheses reported between 2008 and 2017.1 Introduction2 Non-Enzymatic Metabolites of PUFAs2.1 Where Do They Come From?2.2 Why Are They Interesting Metabolites?2.3 A Huge Family of Natural Compounds2.3.1 Presentation of All Families2.3.1.1 Isoprostanoids2.3.1.2 Isofuranoids2.3.1.3 Isoketals2.3.2 Nomenclature of These Metabolites2.3.2.1 Isoprostanoids2.3.2.2 Isofuranoids2.3.2.3 Isoketals3 Total Synthesis Strategies3.1 Isoprostanoids3.2 Isofuranoids3.3 Isoketals4 The Discoveries Behind the Synthesis4.1 Recent Identification and Biomarkers Roles of Isoprostanes and Isofuranes4.2 Biological Properties4.2.1 Phytoprostanes, Isoprostanes, and Neuroprostanes4.2.2 Epoxy-isoprostanes5 Conclusion

Protective Effect of Supplementation of Fish Oil with Highn−3 Polyunsaturated Fatty Acids against Oxidative Stress-Induced DNA Damage of Rat Liver in Vivo

2003 ◽  
Vol 51 (20) ◽  
pp. 6073-6079 ◽  
Author(s):  
Kiyomi Kikugawa ◽  
Yoshinobu Yasuhara ◽  
Ken Ando ◽  
Keiko Koyama ◽  
Kazuyuki Hiramoto ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Fatty Acids ◽  
Dna Damage ◽  
Polyunsaturated Fatty Acids ◽  
Protective Effect ◽  
Fish Oil ◽  
Rat Liver

scholarly journals Relationships between Atherosclerosis and Plasma Antioxidant Micronutrients or Red Blood Cell Polyunsaturated Fatty Acids in People Living with HIV

Nutrients ◽  
2019 ◽  
Vol 11 (6) ◽  
pp. 1292 ◽  
Author(s):  
Katherine J. P. Schwenger ◽  
Bianca M. Arendt ◽  
Marek Smieja ◽  
David W. L. Ma ◽  
Fiona Smaill ◽  
...  
Keyword(s):  
Oxidative Stress ◽  
Blood Pressure ◽  
Fatty Acids ◽  
Multivariate Analysis ◽  
Docosahexaenoic Acid ◽  
Blood Cell ◽  
Polyunsaturated Fatty Acids ◽  
Red Blood Cell ◽  
Gamma Tocopherol ◽  
Plasma Antioxidant

Background: People living with human immunodeficiency virus infection and acquired immune deficiency syndrome (HIV/AIDS) (PLWH) are at an increased risk of cardiovascular disease. Diet-related factors may contribute. The aim of this pilot study was to determine, in PLWH, the relationship between atherosclerosis assessed by carotid intima-media thickness (CIMT) and (A) plasma antioxidant micronutrients and oxidative stress or (B) red blood cell polyunsaturated fatty acids (RBC PUFA), particularly long chain omega-3 polyunsaturated fatty acids (n-3 PUFA). Methods: (A) In a cross-sectional study, subjects had CIMT evaluated by high resolution carotid artery ultrasound. Plasma was collected for vitamin C, measured by spectrophotometry; and alpha- and gamma-tocopherol, retinol, and malondialdehyde—a marker of oxidative stress—using high pressure liquid chromatography and fluorescence spectrophotometry. (B) In a prospective cohort study, other subjects had RBC PUFA measured at baseline, using gas chromatography, and CIMT assessed at baseline and repeated after 2 years. Clinical data was also collected. Results: (A) 91 PLWH participated. Only alpha- and gamma-tocopherol levels were positively correlated with CIMT. In a multivariate analysis, age and systolic blood pressure were significantly associated with CIMT with gamma-tocopherol near significance (p = 0.053). (B) 69 PLWH participated. At baseline, docosahexaenoic acid (n-3 PUFA) and the ratio of docosahexaenoic acid to arachidonic acid (n-6 PUFA) were significantly and negatively correlated with CIMT. However, a multivariate analysis failed to detect a significant relationship either at baseline or 2 years after. Conclusion: In addition to age and systolic blood pressure, atherosclerosis assessed by CIMT might be associated with higher serum gamma-tocopherol levels. There was a non-significant association between CIMT and RBC n-3 PUFA or the ratio of n-3 to n-6 PUFA.

scholarly journals Polyunsaturated ω-3 fatty acids inhibit ACE2-controlled SARS-CoV-2 binding and cellular entry

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Anna Goc ◽  
Aleksandra Niedzwiecki ◽  
Matthias Rath
Keyword(s):  
Fatty Acids ◽  
Polyunsaturated Fatty Acids ◽  
Eicosapentaenoic Acid ◽  
Linolenic Acid ◽  
Cathepsin L ◽  
Saturated Fatty Acids ◽  
Monounsaturated Fatty Acids ◽  
In Vivo Experiments ◽  
Lipid Compounds

AbstractThe strain SARS-CoV-2, newly emerged in late 2019, has been identified as the cause of COVID-19 and the pandemic declared by WHO in early 2020. Although lipids have been shown to possess antiviral efficacy, little is currently known about lipid compounds with anti-SARS-CoV-2 binding and entry properties. To address this issue, we screened, overall, 17 polyunsaturated fatty acids, monounsaturated fatty acids and saturated fatty acids, as wells as lipid-soluble vitamins. In performing target-based ligand screening utilizing the RBD-SARS-CoV-2 sequence, we observed that polyunsaturated fatty acids most effectively interfere with binding to hACE2, the receptor for SARS-CoV-2. Using a spike protein pseudo-virus, we also found that linolenic acid and eicosapentaenoic acid significantly block the entry of SARS-CoV-2. In addition, eicosapentaenoic acid showed higher efficacy than linolenic acid in reducing activity of TMPRSS2 and cathepsin L proteases, but neither of the fatty acids affected their expression at the protein level. Also, neither reduction of hACE2 activity nor binding to the hACE2 receptor upon treatment with these two fatty acids was observed. Although further in vivo experiments are warranted to validate the current findings, our study provides a new insight into the role of lipids as antiviral compounds against the SARS-CoV-2 strain.

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.

Sign in / Sign up

Export Citation Format

Share Document