Number Of Double Bonds Research Articles

Can differential fatty acid composition help migrating birds to limit oxidative lipid damage?

During migratory endurance flights, which are energetically very demanding, migrants have to deal with prolonged elevated generation of reactive oxygen species (ROS). To limit the damaging actions that ROS have on lipids and proteins, migrating birds are known to upregulate their antioxidant defence system. However, there may be additional ways to limit oxidative damage incurred from flying. Migratory endurance flights are fuelled mainly with fatty acids (FAs), and the risk of their peroxidation (resulting in oxidative lipid damage) increases with the number of double bonds in a FA, with polyunsaturated FAs (2 or more double bonds, PUFAs) being most peroxidation-prone. By fuelling their flights with relatively few PUFAs, migratory birds could thus limit oxidative lipid damage. Within migratory birds, there is considerable variation in the length of their flights, with nocturnal migrants making lengthier flight bouts, thus more likely to experience lengthier periods of elevated ROS production, than diurnal migrants. However, whether migrants making lengthier flights incur more oxidative lipid damage is unknown. Neither is it known whether flight length and FA composition are associated. Therefore, we determined plasmatic malondialdehyde level, a marker of oxidative lipid damage, and FA composition of three nocturnal and two diurnal migrant species caught at an autumn stopover site. We found little inter-specific variation in malondialdehyde level, indicating that the amount of oxidative lipid damage was comparable across the species. In contrast, the species strongly differed in their plasmatic FA composition. The nocturnal migrants had significantly lower relative PUFA levels than both diurnal migrants, an effect mainly attributable to linoleic acid, an essential (strictly dietary) FA. Consequently, the susceptibility of plasmatic FAs to lipid peroxidation was significantly lower in the nocturnal than diurnal migrants. Because in birds, energy expenditure during flight decreases with the degree of FA unsaturation, we interpret our observation of lower PUFA levels in nocturnal migrants as support for the idea that utilizing PUFA-poor fuel can help migrating birds to curb oxidative lipid damage.

Comprehensive profiling of conjugated fatty acid isomers and their lipid oxidation products by two-dimensional chiral RP×RP liquid chromatography hyphenated to UV- and SWATH-MS-detection

This research reports on the development of a comprehensive two-dimensional liquid chromatography (2D-LC) method hyphenated to inline DAD-UV and ESI-QTOF-MS/MS-detection for the separation of conjugated polyunsaturated fatty acid isomers and structurally related (saturated, unconjugated, oxidized) compounds. In pharmaceutical lipid formulations conjugated fatty acids can be found as impurities, generated by oxidation of polyunsaturated fatty acids. Due to the structural complexity of resultant multi-component samples one dimensional liquid chromatography may be suboptimal for quality control and impurity profiling. The screened reversed-phase columns showed a lack of selectivity for the conjugated fatty acid isomers but the resolutions improved with the shape selectivity of the stationary phases (C18- < C30- < cholesteryl-ether-bonded). Further enhanced selectivity for the non-chiral conjugated FAs could be achieved with amylose/cellulose-based chiral stationary phases (CSPs) which harbor cavities for selective inclusion depending on E/Z configurations of the double bonds of the analytes. Amylose-based CSPs showed higher selectivity for conjugated fatty acids than the cellulose-based polysaccharide CSPs. Hyphenating the chiral and reversed-phase columns in a comprehensive 2D-LC-setup was favorable since they showed orthogonality and good compatibility, because both were operated under RP-conditions. The chiral dimension (1D) mainly separated the different isomers, while the reversed-phase dimension (2D) separated according to number of double bonds and degree of oxidation. Using this setup, advanced structural annotation of unknowns was possible based on UV-, MS1- and MS2-spectra. Data-independent acquisition (by SWATH) enabled differentiation of positional isomers of oxidized lipids by characteristic MS2-fragments and elucidation of co-eluted compounds by selective extracted ion chromatograms of fragment ions (MS2 EICs).

Triglyceride profiles are associated with subacute exposure to bisphenol A in healthy young adults

Conflicted results from previous epidemiological studies call for mechanistic evidence to associate exposure to bisphenol A (BPA) with cardiometabolic diseases. In this natural experiment among healthy travelers from Los Angeles (LA) to Beijing, we collected paired urine and blood samples before their departure, 6–8 weeks after their arrival to Beijing, and 4–7 weeks after their return to LA for the assessment of urinary BPA and lipidome in the serum fraction of blood, to study the effects of drastically changed BPA exposure on the lipid metabolism in relation to the development of cardiometabolic disorders. We used linear mixed-effects models with random intercepts for participant and phase to examine the associations between urinary BPA and serum lipidome. Among 744 lipid species from seven classes, triglyceride (TGs) species showed the strongest associations with BPA exposure. The elevation in BPA exposure was associated with increases in TGs with short carbon chains or few double bonds, and decreases in TGs with long carbon chains or many double bonds. A significant linear relationship was observed between BPA-associated TG changes and the number of carbons and double-bonds in the acyl chain. No modification effects of gender but of body mass index (BMI) were observed on the associations between BPA exposure and TGs. This interdisciplinary environmental research substantiated the cardiometabolic effects of BPA according to the perturbations of TG profiling.

Rationale for different formulations of omega-3 fatty acids leading to differences in residual cardiovascular risk reduction

Rationale for different formulations of omega-3 fatty acids leading to differences in residual cardiovascular risk reduction

Comprehensive Analysis of Lipid Composition in Human Foremilk and Hindmilk.

Precision nutrition, also referred to as personalized nutrition, focuses on the individual to determine the individual's most effective eating plan to prevent or treat disease. A precision nutrition for infants requires the determination of the profile of human milk. We compared the lipid profiles of the foremilk (i.e., the initial milk of a breastfeed) and hindmilk (the last milk) of six Japanese subjects and evaluated whether a human milk lipid profile is useful for precision nutrition even though the fat concentration fluctuates during lactation. We detected and quantified 527 species with a lipidome analysis by liquid chromatography-tandem mass spectrometry. The fat concentration in hindmilk (120.6 ± 66.7 μmol/mL) was significantly higher than that in foremilk (68.6 ± 33.3 μmol/mL). While the total carbon number of fatty acids in triglyceride (TG) was highest in C52 for all subjects, the second or third number differed among the subjects. Both the distribution of total carbon number of fatty acids included in TG and the distribution of fatty acids in TG classified by the number of double bonds were almost the same in the foremilk and hindmilk in each subject. The lipids levels containing docosahexaenoic acid and arachidonic acid in total lipids of the foremilk and the hindmilk were almost the same in each subject. Among the sphingolipids and glycerophospholipids, the level of sphingomyelin was the highest in four subjects' milk, and phosphatidylcholine was the highest in the other two subjects' milk. The order of their major species was the same in each foremilk and hindmilk. A clustering heatmap revealed the differences between foremilk and hindmilk in the same subject were smaller than the differences among individuals. Our analyses indicate that a human-milk lipid profile reflects individual characteristics and is a worthwhile focus for precision nutrition.

Unraveling the Gordian knot of insulin resistance in type 2 diabetes mellitus

&lt;abstract&gt; &lt;p&gt;β-cells play an important role in unraveling the Gordian knot of insulin resistance in type 2 diabetes. Firstly, a key feature of the etiology of type 2 diabetes, which appears in the prediabetic phase, is a reduction in the unsaturation index (number of cis carbon-carbon double bonds per 100 acyl chains of membrane phospholipids) compared to healthy controls, which leads to a lower rate of transmembrane glucose transport, and consequently causes reduced glucose effectiveness. Thus, the amount of glucose entering the β-cell via glucose transporter-2 reduces insulin production, leading to reduced insulin sensitivity. Secondly, after synthesis of monomer insulin, six monomer insulin molecules can join together in the presence of zinc ions. The mature hexamers are packed inside mature intracellular vesicles that are transported to the β-cell plasma membrane. Fusion of the intracellular vesicle membrane with the β-cell plasma membrane creates a fusion pore that allows expulsion of monomer insulin molecules into the blood circulation. The large dimensions of the monomer insulin molecule (30 Å wide and 35 Å high) require substantial flexibility of the vesicle membrane and the β-cell plasma membrane. Reduction in the unsaturation indexes leads to a lower rate of insulin transport into the blood circulation, which results in a further decrease in insulin sensitivity.&lt;/p&gt; &lt;p&gt;That brings us to a crucial point. The conceit behind the term “insulin resistance” is wrong. It suggests that cells do not respond well to insulin, but the fact is that this term ignores the essential reduction, compared to the plasma glucose concentration, in the amount of glucose entering the β-cell via glucose transporter-2, resulting in reduced insulin production. We now know that an increase in glucose effectiveness, powered by an increased unsaturation index, reframes fundamentally the mechanisms that participate in the glucose homeostasis during type 2 diabetes mellitus.&lt;/p&gt; &lt;/abstract&gt;

Serum Biochemical and Meat Fatty Acid Profiles of Different Chicken Genotypes

Serum biochemical and meat fatty acid profile of different chickens were studied. A total of 144 mixed sex matured chickens of Cosmopolitan (C), Improved Horro (H), Cosmopolitan♂*Improved Horro♀(CH), Improved Horro♂*Cosmopolitan♀ (HC), Indigenous (L) and Koekkoek (KK) were used to determine serum biochemical, of which 36 chickens were also used for fatty acid profile study. Completely randomized design in 6 × 2 factorial arrangements was set up. Serum biochemical and fatty acid profiles were determined by Roche/Hitachi cobas c 501 and gas liquid chromatography (GC) procedures, respectively. There were significant differences (P ≤ 0.001) in Total cholesterol (TC), Triglyceride (TG), Low-density lipoprotein (LDL) and High-density lipoprotein (HDL) among genotypes and between sexes. HDL was inversely related with TC, TG and LDL. Male had significantly higher (P ≤ 0.001) TC, TG, LDL but lower HDL than female. SFA, (Myristic, Pentadecanoic and Palmitic acids) had significantly (P α-linolenic acid significantly (P ≤ 0.01) varied between sexes. The serum biochemical differed across genotypes and between sexes. The difference in the number of carbons, double bond and position of the double bond could affect fatty acid profile among genotypes and between sexes. Chicken products with higher level TC, TG, LDL and SFA might affect human health problems. It could also be interesting topic for future studies.

Triglyceride Saturation in Patients at Risk of NASH and NAFLD: A Cross-Sectional Study

Chemical shift magnetic resonance imaging (MRI) is commonly used to estimate the amount of fat in tissues, namely the proton density fat fraction (PDFF). In addition to PDFF, the type of fat can be inferred and characterized in terms of the number of double bonds (NDB), number of methylene-interrupted double bonds (NMIDB) and the chain length (CL) of the fatty acid chains. The saturation index is potentially a marker for metabolic disorders. This study assesses the feasibility of estimating these parameters independently or in a constrained manner. Correlations with spectroscopy were measured in 109 subjects’ subcutaneous and visceral fat depots (p = 2 × 10−28), and with the NAFLD Activity Score (NAS) from histological evaluation of biopsies. The findings indicate that imaging estimates are comparable to spectroscopy (p = 0.0002), but there is no significant association of NDB with NAS (p = 0.1).

Comparative Analysis of Triglycerides From Different Regions and Mature Lactation Periods in Chinese Human Milk Project (CHMP) Study.

The kinds and proportions of triglycerides of human mature milk play an independent role in the growth of infants. In this study, the human milk samples obtained from eight different Chinese cities (Chengdu, Weihai, Lanzhou, Jinhua, Beijing, Guangzhou, Zhengzhou, and Harbin) and six sequential mature lactation times (30, 60, 90, 120, 150, and 180 days) were detected for the triglycerides. The result demonstrated that total 66 triglycerides were detected in mature human milk, with acyl carbon number (ACN) numbers were locating in the range of 34–54 and double bond (DB) numbers were locating in the range of 0–6. In addition, the percentage of OPO, OPL, and OOO was relatively higher than others, accounted for more than 4% of total triglycerides in all the lactation areas and times, and the percentage of U2S and LLL triglycerides was also richest in mature milk. Furthermore, it was obvious that lactation regions had more significant effect on the triglycerides compared with lactation time and the triacylglycerols (TAGs) of human milk in Guangzhou were clearly different from that in other regions. Therefore, the results of this study will provide data reference for the design of infant formula suitable for Chinese babies.

Profiling of Unsaturated Lipids by Raman Spectroscopy Directly on Solid-Phase Microextraction Probes.

Lipids play a critical role in cellular signaling, energy storage, and the construction of cellular membranes. In this paper, we propose a novel on-site approach for detecting and differentiating enriched unsaturated lipids based on the direct coupling of SPME probes with Raman spectroscopy. To this end, different SPME particles, namely, hydrophilic-lipophilic balanced (HLB), mixed-mode (C8-SCX), and C18, were embedded in polyacrylonitrile (PAN) and tested for their efficacy as biocompatible coatings. The C18/PAN coating showed less background interference compared to the other sorbent materials during the analysis of unsaturated lipids. In addition, different SPME parameters that influence extraction efficiency, such as extraction temperature, extraction time, and washing solvent, were also investigated. Our results indicate a clear dependence between the Raman band intensity related to the number of double bonds in fatty acids mixture and the number of double bonds in a fatty acid. Our findings further show that Raman spectroscopy is especially useful for the analysis of lipid unsaturation, which is calculated as the ratio of n(C═C)/n(CH2) using the intensities of the Raman bands at 1655/1445 cm-1. Furthermore, the developed protocol reveals great SPME activity and high detection ability for several unsaturated lipids in different complex matrixes, such as cod liver oil. Finally, the applicability of this technology was demonstrated via the characterization of cod liver oil and other vegetable oils. Thus, the proposed SPME-Raman spectroscopy approach has a great future potential in food, environmental, clinical, and biological applications.

Role of fatty acids in inflammation, atherosclerosis, metabolic disorders and gout

Fatty acids (FA) are present in all types of organisms and play an important role in energy metabolism. The length and number of double bonds in the FA of membrane phospholipids determine the viscosity, the activity of transport systems and enzymes, and also the susceptibility to lipid peroxidation. The review discusses the influence of free unsaturated FAs with short and long chains on various inflammatory mechanisms, including atherosclerosis. It has been shown that FAs can reduce endothelial activation and affect the metabolism of eicosanoids. A new model of fundamental factors determining the variability of the timing, degree and duration of acute inflammatory reactions in the deposition of urate crystals in tissues, in which FAs play an important role is considered, using gout as an example. In the future, the study of FAs will expand the understanding of the pathophysiology of chronic inflammation in various diseases, metabolic disorders and atherosclerosis and enable the development of new treatment strategies.

Gasoline like fuel from plastic waste pyrolysis and hydrotreatment

Recycling of plastic waste is desirable to lower environmental pollution and fulfil the requirements of circular economy. Energetic utilization is another possibility, however, municipal solid waste containing plastics is usually combusted to generate heat and electricity. An attractive way of dealing with plastic waste is pyrolysis, which has the potential of producing liquid hydrocarbons suitable as a transportation fuel. The pyrolysis results of three plastics produced in the largest amount globally, namely polyethylene, polypropylene and polystyrene as well as their mixtures are presented. The experiments were performed in a laboratory scale batch reactor. The pyrolysis oils were further processed by distillation to provide gasoline and diesel like (distillation cuts at 210 and 350 °C) hydrocarbons. The gasoline fractions were analysed by GC-MS and the composition was compared with the EU gasoline standard. It was found that the oils from PE, PP and PS contain compounds present in standard gasoline. Mixing PS with PE and PP before the pyrolysis, or the oils afterward produces much closer results to standard requirements as PS pyrolysis generates mostly aromatic content. As standard maximizes the olefin content of gasoline to 18 Vol%, hydrogenation was also performed using Pd based catalyst. The hydrogenation process significantly reduced the number of double bonds resulting in low olefin content. Results show that the pyrolysis of plastic waste mixtures containing PE, PP and PS is a viable method to produce pyrolysis oil suitable for gasoline-like fuel extraction and further hydrogenation of the product can provide gasoline fuels with low olefin content.

Formation of melanoidins – Aldol reactions of heterocyclic and short-chain Maillard intermediates

In the course of the Maillard reaction, reducing sugars and amino compounds are converted to colorants, whose chemical structures are still mostly unknown. Active methylene compounds like norfuraneol that can initiate aldol condensation reactions are considered as key intermediates in this reaction. The aim of the present study was to characterize color formation of norfuraneol with different carbonyl compounds and to identify the underlying mechanisms of the reaction. Norfuraneol was incubated with methylglyoxal or diacetyl at elevated temperatures and the resulting reaction mixtures were analyzed by means of high-resolution mass spectrometry. It was demonstrated that aldol reactions lead to the formation of heterogeneous carbohydrate-based oligomers, which are likely to contribute to the elevated browning observed in the reaction mixtures. Furthermore, redox reactions were identified as another important part of the reaction, resulting in an increasing number of double bonds in the detected reaction products.

Investigation of the physical and chemical structure of NSC from sucrose

Carbon materials have been extensively used in scientific research and industrial production. Thereby, a kind of nanospheres of carbon (NSC) was prepared from sucrose, focusing on its physical and chemical structures, getting results that: (1) the yield of NSC is in average of 30.68% of the mass of sucrose, corresponding to 61.97% of carbon conversion. (2) The diameter of NSC is in the range of 150–200 nm, containing 1351.41 m2/g of surface area, which is contributed by the pores in average of diagram of 3.32 nm. (3) The apparent molecule formula (AMF) of NSC can be expressed as C11H2O with unsaturated degree of 11, which is the sum of the numbers of double bonds and rings. (4) It contains the groups of C = C, C-C, C-O-C and C-H; especially, the ratio between the double carbon bonds and single carbon bonds is 1.0. Therefore, this research successfully prepares a kind of special carbon materials by bio-resource, and does benefit to the theory for chemical structure analysis of carbon materials.

Anchoring of Amyloid-β onto Polyunsaturated Phospholipid Membranes

The interaction between the toxic amyloid-β and phospholipid membranes in the early stage of Alzheimer’s disease is complicated and depends on many factors. It was found that polyunsaturated fatty acids affect the incidence of Alzheimer’s disease. The number of double bonds in the phospholipid layer may play an important role in the molecular dynamic behavior of amyloid-β on cell membranes. In the present paper, the interactions between Aβ(25-35) and each of four phospholipids, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine (SAPC), 1-stearoyl-2-docosahexaenooyl-sn-glycero-3-phosphocholine (SDPC), and 1,2-diarachidonoyl-sn-glycero-3-phosphocholine (DAPC), are investigated by using all-atom molecular dynamics simulation. It is interesting that, as the number of double bonds in the membrane increases, the peptide fragment prefers to stay in the surface region of the membrane rather than penetrates deeply into the membrane. With the increasing number of double bonds, the interaction between Aβ(25-35) and the membrane surface becomes stronger, especially for the interaction between the residue 28 (LYS28) in Aβ(25-35) and the phospholipids, anchoring Aβ(25-35) onto the membrane. The double bonds in phospholipid determine not only the adsorption of the peptide fragment Aβ(25-35) but also its conformation, which will influence further aggregation of Aβ in later stages. Communicated by Ramaswamy H. Sarma

Human skin triglycerides prevent bed bug (Cimex lectularius L.) arrestment

Bed bugs (Cimex lectularius) have proliferated globally and have become one of the most challenging pests to control indoors. They are nocturnal and use multiple sensory cues to detect and orient towards their human hosts. After feeding, usually on a sleeping human, they return to a shelter on or around the sleeping surface, but not directly on the host. We hypothesized that although human skin odors attract hungry bed bugs, human skin compounds may also prevent arrestment on hosts. We used arrestment assays to test human skin swabs, extracts from human skin swabs, and pure compounds identified from human skin swabs. When given a choice, bed bugs preferred to arrest on substrates not previously conditioned by humans. These responses were consistent among laboratory-reared and apartment-collected bed bugs. The compounds responsible for this behavior were found to be extractable in hexane, and bed bugs responded to such extracts in a dose-dependent manner. Bioassay-guided fractionation paired with thin-layer chromatography, GC–MS, and LC–MS analyses suggested that triglycerides (TAGs), common compounds found on human skin, were preventing arrestment on shelters. Bed bugs universally avoided sheltering in TAG-treated shelters, which was independent of the number of carbons or the number of double bonds in the TAG. These results provide strong evidence that the complex of human skin compounds serve as multifunctional semiochemicals for bed bugs, with some odorants attracting host-seeking stages, and others (TAGs and possibly other compounds) preventing bed bug arrestment. Host chemistry, environmental conditions and the physiological state of bed bugs likely influence the dual nature behavioral responses of bed bugs to human skin compounds.

Characterisation and Assessment of Physicochemical Properties of Grapeseed Methyl Ester Using Predictive Correlations and ASTM Standards For CI Engine Application

In the present work, a detailed investigation of the physio-chemical characteristics of grapeseed methyl ester (GSME) obtained from winery biomass waste has been carried out to evaluate its suitability as an energy alternate, for CI engines. GSME was subjected to Gas chromatography and mass spectrometry analysis from which fatty acids compositions were determined followed by other interpretations such as carbon number, number of double bonds, etc. Two different predictive correlations were identified from the literature for predicting the properties that are considered important, for using GSME as a fuel. The predicted properties of GSME are compared with the experimental results obtained through standard ASTM procedures, for diesel, neat grapeseed oil (GSO) and GSME, respectively. Further, the influence of the structural and compositional characteristics of GSME on the physicochemical properties like density, kinematic viscosity, lower calorific value, etc. has been evaluated and found to be closer to diesel.

Omnivory in predatory lady beetles is widespread and driven by an appetite for sterols

Abstract Animals maintain physiological and behavioural systems that allow them to detect and consume specific macro‐ and micronutrients to maximize their fitness. One common physiological system is the nutrient‐state‐dependent or demand‐driven appetite. These systems are well described for macronutrient regulation, but not for micronutrients. Sterols are essential micronutrients that all animals need to survive. They are the backbone of many hormones, important in cell signalling and an integral component of cell membranes. Lady beetles are globally distributed predators of insect herbivores. Adult sevenspotted lady beetles maintain a state‐dependent sterol appetite and consume plant tissues to obtain sterols, which improves their fitness. Additionally, sevenspotted lady beetles can detect sterols pre‐ingestion. We used lady beetle species distributed across the three clades of the Coccinellini to determine (a) whether other beetle species maintain a state‐dependent sterol appetite, (b) if sterol structure affects beetles' state‐dependent sterol appetite and (c) whether lady beetles consume foliage in a sterol‐state dependent manner. Additionally, we determined (a) what sensory organ beetles use to detect sterols, (b) their limit of detection and (c) when during development their appetite manifests. All six beetle species we tested maintained a state‐dependent appetite for sterols. Sterol structure affected beetles' propensity to feed on sterol‐treated disks, indicating that the number and position of double bonds in sterol molecules affects beetles' ability to detect or desire to feed on them. Only beetles in clade III fed on plant foliage in response to sterol limitation. Few beetles in any clade that were supplemented with sterols consumed plant tissue. Beetles' appetite for sterols first appeared during the second larval stadium, and the rate of sterol consumption increased with age. Ablations of sensory organs revealed that beetles use their labial palps to detect sterols, and that they detect them at concentrations as low as 1ppm. These data demonstrate that lady beetles across the Coccinellini maintain a state‐dependent appetite for an essential class of micronutrients. They also provide very strong evidence that lady beetles can taste sterols, raising the possibility that they maintain novel as‐yet undescribed gustatory receptors for an essential class of lipids. A free Plain Language Summary can be found within the Supporting Information of this article.

Evaluation and improvement of the oxidative stability of leather fatliquors

Fatliquor oxidation may give leather unpleasant odor, and excessive amounts of Cr(VI) and volatile organic compounds. The accurate evaluation and improvement of the oxidative stability of fatliquors are of great significance to high-quality leather manufacturing. We proposed a set of practical methods for evaluating the oxidative stability of fatliquors on the basis of oxidation induction time, change in iodine value (∆ IV), and change in acid value (∆ AV) under accelerated oxidation conditions (at 100 °C with 10 L/h of air). Oxidation induction time is a highly sensitive marker for quantifying the oxidative stability of fatliquors, and ∆ IV and ∆ AV that are low cost and easy to operate are useful in evaluating the oxidative stability of fatliquors when the oxidation induction time is less than 22 h. The number of double bonds in fatliquors is an important factor affecting oxidative stability. The sulfation modification of fatliquors that greatly reduces double bonds and the addition of antioxidants, especially butylated hydroxyanisole and butylated hydroxytoluene, markedly improve oxidative stability of fatliquors.

Lipid phase transitions in cat oocytes supplemented with deuterated fatty acids

Cryopreservation of oocytes has already been used to preserve genetic resources, but this technology faces limitations when applied to the species whose oocytes contain large amounts of cytoplasmic lipid droplets. Although cryoinjuries in such oocytes are usually associated with the lipid phase transition in lipid droplets, this phenomenon is still poorly understood. We applied Raman spectroscopy of deuterium-labeled lipids to investigate the freezing of lipid droplets inside cat oocytes. Lipid phase separation was detected in oocytes cryopreserved by slow-freezing protocol. For oocytes supplemented with stearic acid, we found that saturated lipids form the ordered phase being distributed at the periphery of lipid droplets. When an oocyte is warmed to physiological temperatures after cooling, a fraction of saturated lipids may remain in the ordered conformational state. The fractions of monounsaturated and polyunsaturated lipids redistribute to the core of lipid droplets. Monounsaturated lipids undergo the transition to the ordered conformational state below −10°C. Using deuterated fatty acids with a different number of double bonds, we reveal how different lipid fractions are involved in the lipid phase transition of a cytoplasmic lipid droplet and how they can affect cell survival. Raman spectroscopy of deuterated lipids has proven to be a promising tool for studying the lipid phase transitions and lipid redistributions inside single organelles within living cells.