scholarly journals Developments in Fatty Acid-Derived Insect Pheromone Production Using Engineered Yeasts

2021 ◽  
Vol 12 ◽  
Author(s):  
Xiaoling Zhang ◽  
Qin Miao ◽  
Xia Xu ◽  
Boyang Ji ◽  
Lingbo Qu ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Pest Control ◽  
Metabolic Flux ◽  
Control Method ◽  
Low Cost ◽  
Insect Pheromones ◽  
Pheromone Production ◽  
Fatty Acid Derivatives ◽  
Insect Sex Pheromones

The use of traditional chemical insecticides for pest control often leads to environmental pollution and a decrease in biodiversity. Recently, insect sex pheromones were applied for sustainable biocontrol of pests in fields, due to their limited adverse impacts on biodiversity and food safety compared to that of other conventional insecticides. However, the structures of insect pheromones are complex, and their chemical synthesis is not commercially feasible. As yeasts have been widely used for fatty acid-derived pheromone production in the past few years, using engineered yeasts may be promising and sustainable for the low-cost production of fatty acid-derived pheromones. The primary fatty acids produced by Saccharomyces cerevisiae and other yeasts are C16 and C18, and it is also possible to rewire/reprogram the metabolic flux for other fatty acids or fatty acid derivatives. This review summarizes the fatty acid biosynthetic pathway in S. cerevisiae and recent progress in yeast engineering in terms of metabolic engineering and synthetic biology strategies to produce insect pheromones. In the future, insect pheromones produced by yeasts might provide an eco-friendly pest control method in agricultural fields.

scholarly journals Investigation of the Membrane Fluidity Regulation of Fatty Acid Intracellular Distribution by Fluorescence Lifetime Imaging of Novel Polarity Sensitive Fluorescent Derivatives

2021 ◽  
Vol 22 (6) ◽  
pp. 3106
Author(s):  
Giada Bianchetti ◽  
Salome Azoulay-Ginsburg ◽  
Nimrod Yosef Keshet-Levy ◽  
Aviv Malka ◽  
Sofia Zilber ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Free Fatty Acids ◽  
Membrane Fluidity ◽  
Fluorescence Lifetime ◽  
Intracellular Distribution ◽  
Fluorescence Lifetime Imaging ◽  
Lifetime Imaging ◽  
Fatty Acid Derivatives ◽  
Polarity Sensitive

Free fatty acids are essential structural components of the cell, and their intracellular distribution and effects on membrane organelles have crucial roles in regulating the metabolism, development, and cell cycle of most cell types. Here we engineered novel fluorescent, polarity-sensitive fatty acid derivatives, with the fatty acid aliphatic chain of increasing length (from 12 to 18 carbons). As in the laurdan probe, the lipophilic acyl tail is connected to the environmentally sensitive dimethylaminonaphthalene moiety. The fluorescence lifetime imaging analysis allowed us to monitor the intracellular distribution of the free fatty acids within the cell, and to simultaneously examine how the fluidity and the microviscosity of the membrane environment influence their localization. Each of these probes can thus be used to investigate the membrane fluidity regulation of the correspondent fatty acid intracellular distribution. We observed that, in PC-12 cells, fluorescent sensitive fatty acid derivatives with increased chain length compartmentalize more preferentially in the fluid regions, characterized by a low microviscosity. Moreover, fatty acid derivatives with the longest chain compartmentalize in lipid droplets and lysosomes with characteristic lifetimes, thus making these probes a promising tool for monitoring lipophagy and related events.

scholarly journals Separation and Purification of ω-6 Linoleic Acid from Crude Tall Oil

Separations ◽  
2020 ◽  
Vol 7 (1) ◽  
pp. 9 ◽  
Author(s):  
Md Shariful Islam ◽  
Lew P. Christopher ◽  
Md Nur Alam
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Low Cost ◽  
Value Added ◽  
Resin Acids ◽  
Separation And Purification ◽  
Tall Oil ◽  
Paper Mills ◽  
Tall Oil Fatty Acids

Crude tall oil (CTO) is the third largest by-product at kraft pulp and paper mills. Due the large presence of value-added fatty and resin acids, CTO has a huge valorization potential as a biobased, readily available, non-food, and low-cost biorefinery feedstock. The objective of this work was to present a method for the isolation of high-value linoleic acid (LA), an omega (ω)-6 essential fatty acid, from CTO using a combination of pretreatment, fractionation, and purification techniques. Following the distillation of CTO to separate the tall oil fatty acids (TOFAs) from CTO, LA was isolated and purified from TOFAs by urea complexation (UC) and low-temperature crystallization (LTC) in the temperature range between −7 and −15 °C. The crystallization yield of LA from CTO in that range was 7.8 w/w at 95.2% purity, with 3.8% w/w of ω-6 γ-linolenic acid (GLA) and 1.0% w/w of ω-3 α-linolenic (ALA) present as contaminants. This is the first report on the isolation of LA from CTO. The approach presented here can be applied to recover other valuable fatty acids. Furthermore, once the targeted fatty acid(s) are isolated, the rest of the TOFAs can be utilized for the production of biodiesel, biobased surfactants, or other valuable bioproducts.

scholarly journals Synthesis and Characterization of an Iron-Containing Fatty Acid-Based Ionomer

2019 ◽  
Vol 2019 ◽  
pp. 1-9
Author(s):  
David A. Stone ◽  
Atanu Biswas ◽  
Zengshe Liu ◽  
Veera Boddu ◽  
H. N. Cheng
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Raw Materials ◽  
Low Cost ◽  
Paper Industry ◽  
Alder Reaction ◽  
Size Exclusion ◽  
Molecular Weights ◽  
Exclusion Chromatography ◽  
Solid Film

One of the desirable research goals today is to convert agro-based raw materials into low-cost functional polymers. Among the readily available natural raw materials are the fatty acids that can be obtained from the hydrolysis of plant oils or from the paper industry as byproducts. In this work, a novel iron-containing ionomer has been prepared through the reaction of fatty acids with steel dust or iron powder in the presence of carbon dioxide and water. Characterization has been achieved via 1H and 13C NMR, FT-IR, and size exclusion chromatography. The product has been shown to have an ionomeric structure, consisting of oligomers of fatty acid carboxylates (derived from Diels-Alder reaction) coupled with iron(II) and iron(III) ions (from the oxidation of iron). Because the fatty acid oligomers have low molecular weights, the ionomer easily dissolves in a solvent and can be made into different physical forms, such as liquid, solid, film, or foam.

D-optimal Design Optimization for the Separation of Oleic Acid from Malaysian High Free Fatty Acid Crude Palm Oil Fatty Acids Mixture Using Urea Complex Fractionation

2021 ◽  
Vol 14 (2) ◽  
Author(s):  
Murad Bahadi ◽  
Nadia Salih ◽  
Jumat Salimon
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Free Fatty Acid ◽  
Vegetable Oils ◽  
Palm Oil ◽  
Low Cost ◽  
High Free Fatty Acid ◽  
Urea Complex ◽  
Crude Palm Oil

Oleic acid (OA) rich vegetable oils is important for the daily essential dietary oils intake but restrict to particular oil such as olive oil. However OA enrichment to other vegetable oil such as palm oil is always possible. OA can be obtained from cheap resources such as high free fatty acid crude palm oil (HFFA-CPO). OA concentrate from HFFA-CPO fatty acids mixture requires efficient and low cost technique. Urea complex crystallization fractionation is a classic method for fractionating saturated and monounsaturated fatty acids from polyunsaturated fatty acids of many vegetable oils. In this work, the separation and purification of oleic acid (OA) from unsaturated fatty acids mixture fraction (USFA) of HFFA-CPO fatty acids mixture by urea complex fractionation (UCF) was studied. The crystallization reaction conditions of urea inclusion for the non-urea complex fraction (NUCF) were optimized using the response surface methodology (RSM) and the optimal model was developed. The results showed high content of OA (88%) in urea complex fraction (UCF) with 86% yield at optimal conditions of urea-to-USFAs ratio of 4.62 : 1 (w/w), crystallization temperature at –10°C and crystallization time of 24 h. The results have demonstrated that urea complex crystallization fractionation method is a very effective with low cost, stable, obtainable, and comparatively ease to recover of OA from polyunsaturated fatty acids (PUFA) of an oil fatty acids mixture. Pure OA is plausible to be used back for the OA enrichment modification into palm oil for new dietary oil.

Probing the effect of straight chain fatty acids on the properties of lead-containing plexiglass

2021 ◽  
Author(s):  
Yujuan Zhang ◽  
Chunhong Wang ◽  
Defeng Wu ◽  
Xintao Guo ◽  
Lei Yu ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Optical Properties ◽  
Fatty Acid ◽  
Methyl Methacrylate ◽  
Low Cost ◽  
Reaction System ◽  
Chain Fatty Acid ◽  
Polymerization Reaction ◽  
Straight Chain ◽  
Straight Chain Fatty Acid

It was found that, just by adding easily accessible and low-cost straight chain fatty acid additives into the co-polymerization reaction system of lead methacrylate with methyl methacrylate, the optical properties...

scholarly journals In contrast with docosahexaenoic acid, eicosapentaenoic acid and hypolipidaemic derivatives decrease hepatic synthesis and secretion of triacylglycerol by decreased diacylglycerol acyltransferase activity and stimulation of fatty acid oxidation

1999 ◽  
Vol 343 (1) ◽  
pp. 191-197 ◽  
Author(s):  
Rolf K. BERGE ◽  
Lise MADSEN ◽  
Hege VAAGENES ◽  
Karl Johan TRONSTAD ◽  
Martin GÖTTLICHER ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Docosahexaenoic Acid ◽  
Eicosapentaenoic Acid ◽  
Palmitic Acid ◽  
Diacylglycerol Acyltransferase ◽  
Acid Oxidation ◽  
Fatty Acid Derivatives ◽  
Triacylglycerol Synthesis

Hypolipidaemic fatty acid derivatives and polyunsaturated fatty acids decrease concentrations of plasma triacylglycerol by mechanisms that are not fully understood. Because poor susceptibility to β- and/or ω-oxidation is apparently a determinant of the peroxisome proliferating and hypolipidaemic capacity of fatty acids and derivatives, the relative importance of activation of the peroxisome-proliferator-activated receptor α (PPARα), fatty acid oxidation and triacylglycerol synthesis were examined. We have compared the effects of differentially β-oxidizable fatty acids on these parameters in primary cultures of rat hepatocytes. Tetradecylthioacetic acid (TTA), 2-methyleicosapentaenoic acid and 3-thia-octadecatetraenoic acid, which are non-β-oxidizable fatty acid derivatives, were potent activators of a glucocorticoid receptor (GR)-PPARα chimaera. This activation was paradoxically reflected in an substantially increased oxidation of [1-14C]palmitic acid and/or oleic acid. The incorporation of [1-14C]palmitic acid and/or oleic acid into cell-associated and secreted triacylglycerol was decreased by 15-20% and 30% respectively with these non-β-oxidizable fatty acid derivatives. The CoA ester of TTA inhibited the esterification of 1,2-diacylglycerol in rat liver microsomes. Both eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) activated GR-PPARα. EPA increased the oxidation of [1-14C]palmitic acid but DHA had no effect. The CoA ester of EPA inhibited the esterification of 1,2-diacylglycerol, whereas DHA-CoA had no effect. The ratio between synthesized triacylglycerol and diacylglycerol was lower in hepatocytes cultured with EPA in the medium compared with DHA or oleic acid, indicating a decreased conversion of diacylglycerol to triacylglycerol. Indeed, the incorporation of [1-14C]oleic acid into secreted triacylglycerol was decreased by 20% in the presence of EPA. In conclusion, a decreased availability of fatty acids for triacylglycerol synthesis by increased mitochondrial β-oxidation and decreased triacylglycerol formation caused by inhibition of diacylglycerol acyltransferase might explain the hypolipidaemic effect of TTA and EPA.

scholarly journals Continuous photoproduction of hydrocarbon drop-in fuel by microbial cell factories

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Solène Moulin ◽  
Bertrand Légeret ◽  
Stéphanie Blangy ◽  
Damien Sorigué ◽  
Adrien Burlacot ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Gas Phase ◽  
Low Cost ◽  
Continuous Production ◽  
Production Costs ◽  
Cell Factory ◽  
Medium Chain ◽  
Continuous Release ◽  
Cell Factories

Abstract Use of microbes to produce liquid transportation fuels is not yet economically viable. A key point to reduce production costs is the design a cell factory that combines the continuous production of drop-in fuel molecules with the ability to recover products from the cell culture at low cost. Medium-chain hydrocarbons seem ideal targets because they can be produced from abundant fatty acids and, due to their volatility, can be easily collected in gas phase. However, pathways used to produce hydrocarbons from fatty acids require two steps, low efficient enzymes and/or complex electron donors. Recently, a new hydrocarbon-forming route involving a single enzyme called fatty acid photodecarboxylase (FAP) was discovered in microalgae. Here, we show that in illuminated E. coli cultures coexpression of FAP and a medium-chain fatty acid thioesterase results in continuous release of volatile hydrocarbons. Maximum hydrocarbon productivity was reached under low/medium light while higher irradiance resulted in decreased amounts of FAP. It was also found that the production rate of hydrocarbons was constant for at least 5 days and that 30% of total hydrocarbons could be collected in the gas phase of the culture. This work thus demonstrates that the photochemistry of the FAP can be harnessed to design a simple cell factory that continuously produces hydrocarbons easy to recover and in pure form.

scholarly journals The Fatty-Acid Hydratase Activity of the Most Common Probiotic Microorganisms

Catalysts ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 154 ◽  
Author(s):  
Stefano Serra ◽  
Davide De Simeis ◽  
Antonio Castagna ◽  
Mattia Valentino
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
Lactobacillus Rhamnosus ◽  
Hydration Reaction ◽  
Fatty Acid Derivatives ◽  
Hydratase Activity ◽  
Whole Cell Biotransformation ◽  
Octadecadienoic Acids ◽  
Very High

In this work, we studied the biotechnological potential of thirteen probiotic microorganisms currently used to improve human health. We discovered that the majority of the investigated bacteria are able to catalyze the hydration reaction of the unsaturated fatty acids (UFAs). We evaluated their biocatalytic activity toward the three most common vegetable UFAs, namely oleic, linoleic, and linolenic acids. The whole-cell biotransformation experiments were performed using a fatty acid concentration of 3 g/L in anaerobic conditions. Through these means, we assessed that the main part of the investigated strains catalyzed the hydration reaction of UFAs with very high regio- and stereoselectivity. Our biotransformation reactions afforded almost exclusively 10-hydroxy fatty acid derivatives with the single exception of Lactobacillus acidophilus ATCC SD5212, which converted linoleic acid in a mixture of 13-hydroxy and 10-hydroxy derivatives. Oleic, linoleic, and linolenic acids were transformed into (R)-10-hydroxystearic acid, (S)-(12Z)-10-hydroxy-octadecenoic, and (S)-(12Z,15Z)-10-hydroxy-octadecadienoic acids, respectively, usually with very high enantiomeric purity (ee > 95%). It is worth noting that the biocatalytic capabilities of the thirteen investigated strains may change considerably from each other, both in terms of activity, stereoselectivity, and transformation yields. Lactobacillus rhamnosus ATCC 53103 and Lactobacillus plantarum 299 V proved to be the most versatile, being able to efficiently and selectively hydrate all three investigated fatty acids.

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