Apocynaceae Seed Lipids: Characterization and Occurrence of Isoricinoleic Acid and Triacylglycerol Estolides

Isoricinoleic acid (9‐hydroxy‐cis‐12‐octadecenoic acid; IR) is a potential renewable feedstock for the oleochemical industry, a precursor for the synthesis of antimicrobial compounds and a component of the seed oil of certain plants in the Apocynaceae. For a more detailed survey of this plant family, seeds of 18 species representing different subfamilies were obtained and acyl composition and oil content was determined. IR was observed only in species of the tribes Wrightieae and Nerieae in the Apocynoideae subfamily and is reported for the first time in the seed oil of the desert rose Adenium obesum in which it is present at a level of around 26 %. In contrast to previous reports, IR was not found in oil from Holarrhena species, H. antidysenterica and H. pubescens, nor in oil from Annona squamosa. To examine the oil structure, samples were analyzed using MALDI‐TOF mass spectrometry. This technique proved to be a simple method to demonstrate the occurrence of the estolide 9‐acetoxy‐cis‐12‐octadecenoic acid in oil from Nerium oleander and gave further insight into the distribution of estolides within the oil, revealing the presence of tetra‐ and penta‐acyl‐TAG molecules, and molecules containing IR esterified to all three position of glycerol. For other species in which IR was observed, the HFA was found to be a component of seed TAG, but no secondary acylation of the hydroxyl groups was observed.     

Identification and Distribution of Oxygenated Fatty Acids in Plantago Seed Lipids

Plant oils rich in oxygenated fatty acids (FAs) are of interest as renewable raw materials for industry. Previous studies reported unusual oxygenated FAs in the seed lipids of Plantago major and P. ovata. To determine if oxygenated FAs are a common component of Plantago seed oils, seed fatty acyl quality and quantity were determined for 23 Plantago species. Fatty acyl content, as a percentage of dry weight, ranged from 4.9 % in P. sempervirens to 18.8 % in P. coronopus. Oxygenated FAs were a frequent, but not ubiquitous component of Plantago seed lipids, reaching a level of almost 15 % in the seeds of P. nivalis. The oxygenated FAs were identified as isoricinoleic acid (9-hydroxy-cis-12-octadecenoic acid, IR) and 9-oxo-cis-12-octadecenoic acid (OX). When present, most species contained both IR and OX. FAs containing oxo groups have not been reported as components of the seed oil of other plant species that synthesize IR or ricinoleic acid (12-hydroxy-cis-9-octadecenoic acid), suggesting unique aspects to the pathway of oxygenated FA biosynthesis in Plantago. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) demonstrated that IR and OX are components of triacylglycerol, and triacylglycerol estolides are a minor component of the seed oil of P. lanceolata with secondary acylation by oxygenated FAs.     

Synthesis of Sodium (+)-(12S,13R)-Epoxy-cis-9-octadecenyl Sulfonate from Vernonia Oil

A water-soluble, foaming epoxyalkene sulfonate, sodium (+)-(12S,13R)-epoxy-cis-9-octadecenyl sulfonate, was synthesized from vernonia oil (VO) by a series of simple reactions that include transesterification, metal hydride reduction, tosylation, and S_N2 reactions. Conversion of VO into vernonia oil methyl esters (VOME) using sodium methoxide was quantitative. Subsequent reduction of VOME with lithium aluminum hydride yielded (+)-(12S,13R)-epoxy-cis-9-octadecenol (94%), along with minor amounts of hexadecenol, octadecenol, cis-9-octadecenol, and cis-9,12-octadecandienol. The (+)-(12S,13R)-epoxy-cis-9-octadecenol, was tosylated with p-toluenesulfonyl chloride to give (+)-(12S,13R)-epoxy-cis-9-octadecenyl tosylate at 96% yield. Iodination of the tosylate with sodium iodide and subsequent S_N2 reaction with sodium sulfite afforded (+)-(12S,13R)-epoxy-cis-9-octadecenyl sulfonate (63% yield). This study demonstrates the ability to produce an epoxyalkenyl sulfonate, belonging to a class of anionic surfactants, from VO without destroying the epoxy functionality in the (+)-(12S,13R)-epoxy-cis-9-octadecenyl moiety of VO. The critical micelle concentration of the synthesized sulfonate was also determined.     

Mono‐Estolide Synthesis from trans‐8‐Hydroxy‐Fatty Acids by Lipases in Solvent‐Free Media and Their Physical Properties

Pseudomonas aeruginosa 42A2 is known to produce two hydroxy‐fatty acids, 10(S)‐hydroxy‐8(E)‐octadecenoic and 7,10(S,S)‐dihydroxy‐8(E)‐octadecenoic acids, when cultivated in a mineral medium using oleic acid as a single carbon source. These compounds were purified, 91 and 96 % respectively, to produce two new families of estolides: trans‐8‐estolides and saturated estolides from the monohydroxylated monomer. trans‐8‐estolides were produced by three different lipases (Novozym 435, Lipozyme RM IM and Lipozyme TL IM) with reaction yields between 68.4 ± 2.1 and 94.7 ± 2.4 % in a solvent‐free medium at 80 °C in 168 h under vacuum. Novozym 435 was found to be the most efficient biocatalyst for both hydroxy‐fatty acids with reaction yields of 71.7 ± 2.3 and 94.7 ± 2.4 %, respectively. Moreover, saturated estolides were also produced from a saturated 10(S)‐hydroxy‐8(E)‐octadecenoic. These estolides were chemically and enzymatically synthesized with Novozym 435, under the previous described reaction conditions with yields of 60.7 ± 2.1 and 71.2 ± 2.3 % respectively. Finally, viscosity, glass transition temperature, decomposition temperatures and enthalpies were determined to characterize both types of estolides. Thermal applications for both types of polyesters were improved since glass transition temperatures were lowered and decomposition temperatures were increased, with respect to their corresponding substrates.     

Isolation and Characterization of Chicken Yolk Vitelline Membrane Lipids Using Eggs Enriched With Conjugated Linoleic Acid

The vitelline membrane (VM) encloses the chicken egg yolk, separating it from albumen. The VM weakens during storage, and dietary lipid modification significantly affects its strength. However, no studies have characterize the fatty acyl residue (FA) composition of the VM, and reports of VM isolation and quantified lipid content are inconsistent. Therefore, the objectives of this study were: (1) to develop a washing and isolation method that removes residual yolk from VM without damage; (2) to determine the FA and lipid composition of CLA‐rich egg yolk VM, relative to controls; (3) to determine the effect of 20 days of refrigeration on VM FA and lipid composition. To determine VM FA and lipid composition, 36 hens received either a corn‐soybean meal‐based control diet (“Control”), or the Control supplemented with either 10 % soy oil (“Soy control”), or 10 % CLA‐rich soy oil (“CLA”) for 30 days. VM were analyzed the day of collection (“fresh”), or after 20 days of refrigeration (“refrigerated”). There were no differences in FA compositions of fresh and refrigerated membranes within a treatment. CLA‐rich yolk VM contains CLA, greater SFA, and significantly greater DHA relative to controls. Direct MALDI‐TOF–MS identified 15 phosphatidylcholines, three phosphatidylethanolamines, one sphingomyelin, and 15 triacylglycerols in VM. Lipid species that showed significant differences among egg types included nine phosphatidylcholines and six triacylglycerols. MALDI analysis indicated significant differences in nine lipid classes on the VM inner layer. After refrigeration, five lipid classes on the inner layer and seven lipid classes on the outer layer had statistically significant differences among VM types.     

Identification of n‐6 Monounsaturated Fatty Acids in Acer Seed Oils

Seed oils from Acer species are a potential source of the nutraceutical fatty acids, nervonic acid (cis‐15‐tetracosenoic acid, NA), and γ‐linolenic acid (cis‐6,9,12‐octadecatrienoic acid, GLA). To further characterize the genus, seed fatty acid content and composition were determined for 20 species of Acer. Fatty acid content ranged from 8.2% for Acer macrophyllum to over 36% for A. mono and A. negundo. The presence of very‐long‐chain fatty acids (VLCFA), with chain length of 20‐carbons or greater, and GLA were characteristic features of the seed oils. In all species, erucic acid (cis‐13‐docosenoic acid, EA) was the predominant VLCFA with the highest level of NA being only 8.6% in A. olivianum. Regioselective lipase digestion demonstrated that VLCFA are largely absent from the sn‐2 position of seed triacylglycerol, whereas GLA is primarily located at this position. Five Acer species contained low levels (<2%) of cis‐12‐octadecenoic acid and cis‐14‐eicosenoic acid, uncommon n‐6 fatty acids not previously reported from Acer.     

Characterization and antioxidative properties of condensed tannins from the mangrove plant Aegiceras corniculatum

Freeze‐dried leaf, stem bark, and root bark powders of Aegiceras corniculatum were extracted with three different types of polar solvents: methanol, ethyl acetate, and water. The methanol extracts had the highest concentrations in total phenolics and extractable condensed tannins, followed by water and ethyl acetate extracts. Analysis by matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOF MS) suggested that condensed tannins from leaf, stem bark, and root bark contained prodelphinidins and procyanidins, with the predominance of prodelphinidins and high level of galloylation. Acid‐catalyzed degradation in the presence of benzyl mercaptan indicated that gallocatechin, epigallocatechin, epigallocatechin‐3‐O‐gallate, and epicatechin‐3‐O‐gallate occurred as the terminal units and (epi)gallocatechin, (epi)gallocatechin‐3‐O‐gallate, (epi)catechin, and (epi)catechin‐3‐O‐gallate occurred as the extension units. The mean degrees of polymerization (mDP) of condensed tannins from leaf, stem bark, and root bark were 13.5, 7.4, and 12.3, respectively. The condensed tannins from leaf and stem bark exhibited a higher DPPH radical scavenging activity and ferric reducing/antioxidant power compared to that of synthetic antioxidant butylated hydroxyanisole (BHA). © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Heart-Cut Two-Dimensional Countercurrent Chromatography for the Isolation of a Furan Fatty Acid Triacylglycerol from Latex Gloves and Identification of Further Lipid Compounds

Hevea brasiliensis latex from specific genotypes such as RRIM501 or PB235 is one of the richest natural sources of furan fatty acid 9-(3-methyl-5-pentylfuran-2-yl)-nonanoic acid (9M5), which is mainly present in the form of triacylglycerols. In this study, we successfully isolated a triacylglycerol esterified with three 9M5 molecules (tri-9M5) with a purity of 97% from the lipid extract of latex gloves by means of countercurrent chromatography (CCC). The gas chromatography with a mass spectrometry (GC/MS) spectrum of tri-9M5 not only featured the diagnostic fragment ion [M-RCOO]⁺ of triacylglycerols but also a fragment ion shifted by 16 Da to higher mass which corresponded with [M-RCO]⁺. [M-RCO]⁺ was only detected in triacylglycerols substituted with at least one furan fatty acid. Additionally, five γ-tocotrienyl fatty acid esters (γ-T₃-FA esters), namely, γ-T₃-16:0, γ-T₃-18:0, γ-T₃-18:1n-9, γ-T₃-18:2n-6 and γ-T₃-20:0, were detected in the sample. Contributions of γ-T₃-FA esters with 18:1n-9 and 18:2n-6 which co-eluted in GC/MS could be calculated after mathematical correction for contributions of the ¹³C₂ isotope peak of γ-T₃-18:2n-6 to γ-T₃-18:1n-9. This was necessary for quantitation of these two γ-T₃-FA esters. Improved separation of the γ-T₃-FA esters could be achieved by the novel heart-cut recycling CCC mode (four cycles). Sterols detected in disposable latex gloves were β-sitosterol, Δ⁵-avenasterol, and stigmasterol along with small quantities of 24-methylene-cycloartenol and Δ⁵-citrostadienol.     

Dragon Fruit (Hylocereus spp.) Seed Oils: Their Characterization and Stability Under Storage Conditions

Oil was extracted from the seeds of white-flesh and red-flesh dragon fruits (Hylocereus spp.) using a cold extraction process with petroleum ether. The seeds contained significant amounts of oil (32–34 %). The main fatty acids were linoleic acid (C18:2, 45–55 %), oleic acid (C18:1, 19–24 %), palmitic acid (C16:0, 15–18 %) and stearic acid (C18:0, 7–8 %). The seed oils are interesting from a nutritional point of view as they contain a large amount of essential fatty acids, amounting to up to 56 %. In both dragon fruit seed oils, tri-unsaturated triacylglycerol (TAG) was mainly found while their TAG composition and relative percentage however varied considerably. Therefore, they showed a different melting profile. A significant amount of total tocopherols was observed (407–657 mg/kg) in which the α-tocopherol was the most abundant (~72 % of total tocopherol content). The impact of storage conditions, cold and room temperatures, on the oxidative stability and behavior of tocopherols was monitored over a 3-month storage period. During storage, the oxidative profile changed with a favorably low oxidation rate (~1 mequiv O₂/week) whilst tocopherols decreased the most at room temperature. After 12 weeks, the total tocopherol content, however, still remained high (65–84 % compared to the initial oils). Hereto, the dragon fruit seed oils can be considered as a potential source of essential fatty acids and tocopherols, with a good oxidative resistance.     

Profiling of the Beneficial and Potentially Harmful Components of Trichodesma indicum Seed and Seed Oil Obtained by Ultrasound-Assisted Extraction

The beneficial and potentially harmful bioactive components in the seeds and seed oil of Trichodesma indicum L. (Boraginaceae) were investigated in the present study. The T. indicum seeds were rich in oil (29.0%), phenolic compounds (PC, 1881.2 mg per 100 g), and pyrrolizidine alkaloids (PA, 2,702,338 ng g⁻¹). Seven PC were identified in T. indicum seeds by liquid chromatography-quadrupole-time-of-flight mass spectrometry system (LC-Q-TOF-MS). Rosmarinic acid (67%) and isomers of salvianolic acid B/E/L (26%) were the main phenolics, while melitric acid A and sebestenoid C/D constituted 6% and 1%, respectively. Only a minor part of the total PC and PA was transferred from the seeds into the oil fraction during the extraction procedure (<0.03%). The T. indicum seed oil was predominated by the following polyunsaturated fatty acids (PUFA):linoleic (23.2%), γ-linolenic (6.0%), α-linolenic (26.8%), and stearidonic (5.9%). High levels were also observed for oleic (26.7%) and palmitic (7.4%) acids. Additionally, notable amounts of γ-tocopherol (92% of total tocochromanols) and β-sitosterol (53% of total sterols) were found in T. indicum seed oil. The total content of tocochromanols, sterols, and carotenoids in T. indicum seed oil was 102.7, 236.0, and 0.6 mg per 100 g oil, respectively. Among 10 detected hepatotoxic PA in T. indicum seeds, intermedine/lycopsamine/indicine (90.9%), intermedine N-oxide (4.9%), and lycopsamine N-oxide (4.1%) consisted 99.9% of the total PA concentration. The T. indicum seeds should be used carefully due to the presence of PA.     

Physicochemical Properties of <Emphasis Type="Italic">Acer truncatum</Emphasis> Seed Oil Extracted Using Supercritical Carbon Dioxide

Acer truncatum seed oil rich in nervonic acid was extracted using supercritical carbon dioxide. GC (Gas Chromatography) analysis revealed that the oil contained approximately 6.22% nervonic acid. The sn‐2 compositions were also determined using lipase hydrolysis. A total of 52 triacylglycerides (TAG) were tentatively identified in the oil using an ultra‐performance convergence chromatography (UPC²) coupled with quadrupole time‐of‐flight mass spectrometry (Q‐TOF‐MS) for the first time. In addition, the contents of phytosterols (1961.9–2402.8 μmol/kg) and β‐carotene (2.09–2.35 μmol/kg) were also quantified for the first time, along with tocopherols (2352.0–2654.3 μmol/kg). The γ‐tocopherol (1296.9‐1442.3 μmol/kg) was the primary tocopherol, while β‐sitosterol (1355.2–1631.3 μmol/kg) was the dominant phytosterol. The physicochemical properties of the oil were also investigated. This study indicated that A. truncatum seed oil is rich in nervonic acid and other nutraceutical constituents. It has a high potential in functional foods for improving human health.     

Structure Identification of Triacylglycerols in the Seed Oil of Momordica Charantia L. Var. Abbreviata Ser.

Triacylglycerols (TGs) in the seed oil of Momordica charantia L. var. abbreviata Ser. (MCV) were separated by non-aqueous reversed-phase (NARP)-HPLC. Many of the TGs contain two different fatty acyl chains, such as palmitic (P), stearic (S), oleic (O), linoleic (L), and conjugated linolenic acid (CLn). Seven pairs of AAB/ABA-type TGs might present in the seed oil of MCV, namely CLnCLnP/CLnPCLn, CLnCLnS/CLnSCLn, CLnCLnO/CLnOCLn, CLnCLnL/CLnLCLn, SSCLn/SCLnS, OOCLn/OCLnO and LLCLn/LCLnL. The positional isomers of a AAB/ABA-type TGs pair yielded mass spectra showing a significant difference in relative abundance ratios of the fragment ions [AA]⁺ to [AB]⁺, which were produced by preferred losses of the fatty acid from the 1/3-position compared to the 2-position of the glycerol backbone. The precise stereospecific structures of the predominant regioisomers of TGs in AAB/ABA pairs were identified by atmospheric pressure chemical ionization mass spectrometry (APCI-MS) according to the special relative abundance ratios of the fragment ions [AA]⁺ to [AB]⁺. TGs with CLn occupying the sn-2 position in seven pairs of AAB/ABA might be major constituents of the oil, such as CLnCLnS, LCLnL, CLnCLnP, and so on. Some of the TGs which were isolated and collected as fractions from the seed oil of MCV by NARP-HPLC were further analyzed by ¹³C-NMR. ¹³C-NMR data of type-AAA TGs containing α-eleostearic acyl have been complemented.     

Characterization of Volatile Compounds of Virgin Olive Oil Originating from the USA

The volatile profiles of virgin olive oils originating from the USA were first studied: 71 volatile compounds were identified in 21 monovarietal virgin olive oils using solid‐phase microextraction–gas chromatography/mass spectrometry, representing 100 % of the headspace composition. Principal component analysis (PCA) allowed for the grouping of olive oils based on geographical origin, and also the distinguishing of olive oil varieties by their relative positions in the group; 17 distinguishable volatile compounds that significantly contributed to the olive oil classification were found to be distributed on a PCA plot according to their sensory attributes. Moreover, the major volatile components were compared among varieties and origins to clarify the genetic and geographic influences. Our results indicate the significant effects of both origin and cultivar on the volatile composition of olive oil as well as the dominant role of the geographic effect compared to the genetic effect on applied samples.     

Extraction and Characterization of Seed Oil from Naturally Grown Chinese Tallow Trees

Seeds were collected from locally and naturally grown Chinese tallow trees (CTT) and characterized for general physical and chemical properties and fatty acid composition of the lipids. The effects of four different solvents (petroleum ether, hexane, diethyl ether, and 95 % ethanol) and two extraction methods (supercritical carbon dioxide (SC-CO₂) and conventional Soxhlet) on the properties of the CTT seed oil, including Chinese vegetable tallow (CVT) and stillingia oil (SO), were also investigated. In general, the yields of CVT and SO did not vary based on solvent for Soxhlet extraction and solvent-free SC-CO₂ extraction, except that the yield of CVT from SC-CO₂ extraction was substantially lower. Nevertheless, the CTT seed oil, extracted by SC-CO₂ displayed better quality than those extracted by Soxhlet extraction in terms of color, residual precipitation, and acid value of the oils. The pretreatment of CTT seed by 3 % aqueous sodium bicarbonate solution likely promoted the hydrolysis of triglyceride and caused the high acid value in the CVT samples. The iodine value at around 180 indicated that the SO is a highly unsaturated drying oil. Palmitic (76 %) and oleic (23 %) are two dominant fatty acids in CVT while linolenic (43 %), linoleic (31 %), and oleic (13 %) are the dominant fatty acids in SO.     

Characterization and Benzo[a]pyrene Content Analysis of Camellia Seed Oil Extracted by a Novel Subcritical Fluid Extraction

A novel continuous subcritical n‐butane extraction technique for Camellia seed oil was explored. The fatty acid composition, physicochemical properties, and benzo[a]pyrene content of Camellia seed oil extracted using this subcritical technique were analyzed. Orthogonal experiment design (L₉(3⁴)) was adopted to optimize extraction conditions. At a temperature of 45 °C, a pressure of 0.5 MPa, a time of 50 min and a bulk density of 0.7 kg/L, an extraction yield of 99.12 ± 0.20 % was obtained. The major components of Camellia seed oil are oleic acid (73.12 ± 0.40 %), palmitic acid (10.38 ± 0.05 %), and linoleic acid (9.15 ± 0.03 %). Unsaturated fatty acids represent 83.78 ± 0.03 % of the total fatty acids present. Eight physicochemical indexes were assayed, namely, iodine value (83.00 ± 0.21 g I/100 g), saponification value (154.81 ± 2.00 mg KOH/g), freezing‐point (?8.00 ± 0.10 °C), unsaponifiable matter (5.00 ± 0.40 g/kg), smoke point (215.00 ± 1.00 °C), acid value (1.24 ± 0.03 mg KOH/g), refrigeration test (transparent, at 0 °C for 5.5 h), and refractive index (1.46 ± 0.06, at 25 °C). Benzo[a]pyrene was not detected in Camellia seed oil extracted by continuous subcritical n‐butane extraction. In comparison, the benzo[a]pyrene levels of crude Camellia seed oil extracted by hot press extraction and refined Camellia seed oil were measured at 26.55 ± 0.70 and 5.69 ± 0.04 μg/kg respectively.     

Enzymatic Interesterification Between Pine Seed Oil and a Hydrogenated Fat to Prepare Semi-Solid Fats Rich in Pinolenic Acid and Other Polyunsaturated Fatty Acids

Enzyme catalyzed interesterification (EIE) of pine seed oil (PSO) and a fully hydrogenated soybean oil (FHSBO) were studied in batch reactors in solvent-free media to prepare different semisolid fats rich in polyunsaturated fatty acids (PUFA). Optimal operation conditions found were: 10 % (w/w) enzyme loading, 75 °C and magnetic agitation at 300 rpm. Quasi-equilibrium conditions were reached after 2, 3 and 6 h, when immobilized lipases from Thermomyces lanuginosus (Lipozyme^® TL IM), Candida antarctica B. (Novozym^® 435) and Rhizomucor miehei (Lipozyme^® RM IM) from Novozymes A/S (Bagsvaerd, Denmark) were employed, respectively. Similar distributions of unsaturated to saturated fatty acid (UFA/SFA) residues along the glycerol backbone of the fat products were obtained with both non-selective and sn-1(3) regioselective lipases due to significant spontaneous acyl migration during the reaction. The products had higher UFA/SFA ratios at the sn-2 position (2.4–2.5, 1.4–1.7, and 0.5–0.8 for the trials involving 20, 40 and 70 % FHSBO, w/w, respectively) than the corresponding physical blends (0.8, 0.4 and 0.5, respectively). Fat products containing 3.1–11.6 % (w/w) pinolenic acid (Pn) and 16.1–35.7 % (w/w) linoleic acid (L) at the sn-2 position were prepared. The free acid contents of EIE products prepared with Lipozyme^® TL IM and Novozym^® 435 were 6.1–6.4 and 2.5–2.6, respectively. Residual activities of Lipozyme^® TL IM and Novozym^® 435 diminish by ca. 20 % after 9 reaction cycles.     

Evaluation of the Triglyceride Composition of Pomegranate Seed Oil by RP‐HPLC Followed by GC‐MS

Triglyceride composition and fatty acid profiles of pomegranate seed oil were evaluated by newly developed methods in reverse‐phase‐high performance liquid chromatography (RP‐HPLC) and gas chromatography (GC), respectively. Different compositions of the mobile phase (acetone and acetonitrile) and flow rates for the HPLC system were used to obtain better separation for accurate quantitative analysis. Triglycerides with conjugated fatty acids (CLnAs) were eluted in order of the polarity of their geometrical isomers (c, t, c < t, t, c < t, t, t). The dominant triglyceride was found to be PuPuPu (32.99 %) in pomegranate seed oil, followed by PuPuCa and PuCaCa containing punicic acid and catalpic acid with total triglyceridelevels of 27.72 and 10.11 %, respectively. For fatty acid composition analysis, triglyceride fractions were derivatized into their respective methylesters which were injected into gas chromatography‐mass spectrometry (GC‐MS) to identify and gas chromatography‐flame ionization detector (GC‐FID) to quantify the conjugated fatty acids of each fraction of triglycerides. Punicic acid was found to be dominant (76.57 %) followed by catalpic acid (6.47 %) and β‐eleotearic acid (1.45 %). Pomegranate seed contained greater amounts of conjugated linolenic acids. These results showed that the present study provides more information about the composition of the triglyceride and fatty acid profiles of pomegranate seed oil compared to the reported studies. Therefore, the developed methods in this study can be used for the identification of the triglyceride and fatty acid composition for pomegranate seed oils and some such specials edible oils including CLnA isomers.     

Dynamic Features of the Rumen Metabolism of Linoleic Acid,Linolenic Acid and Linseed Oil Measured in Vitro

The lipid quality of ruminant products is largely determined by the extent of rumen microbial biohydrogenation (BH) of polyunsaturated fatty acids (FAs) and the substances formed thereby. In vitro batch incubations with mixed rumen bacteria were tracked over 24 h to characterize the profiles and kinetics of the BH products from three lipid sources: pure linoleic acid (c9,c12–18:2), pure linolenic acid (c9,c12,c15–18:3) and linseed oil (mainly c9,c12,c15–18:3 in triacylglycerols). After 24 h of incubation biohydrogenation was more complete for c9,c12–18:2, which gave mainly stearic acid (18:0), than for c9,c12,c15–18:3, which yielded mainly trans-18:1 FAs. This suggests inhibition of the final BH step (18:1 to 18:0). Incubations of c9,c12–18:2 resulted in high levels of carbon 10- and 12-desaturated 18:1, t10,c12- and c9,t11-CLAs. Incubations of c9,c12,c15–18:3 resulted in high levels of t11–18:1, carbon 13- and 15-desaturated 18:1 as well as t11,c15–18:2 and 11,13-CLAs. A comparative study of linolenic acid and linseed oil kinetics revealed that the BH process was not significantly slowed by the esterification of polyunsaturated FAs, but may have been limited by the isomerization step in which the cis12 double bond goes to the trans11 position. The disappearance rates of c9,c12–18:2 and c9,c12,c15–18:3 ranged from 23.6 to 44.6%/h. The wide variety of BH intermediates found here underlines the large number of possible BH pathways. These data help provide a basis for dynamic approaches to BH processes.     

Preparation and Characterization of Oil Rich in Odd Chain Fatty Acids from Rhodococcus opacus PD630

Odd-chain fatty acids (OCFA) are widely used in pharmaceutical and food industries, as well as the chemical industry. In this study, oil rich in OCFA was produced by Rhodococcus opacus PD630, and 1-propanol in combination with glucose was used as the carbon and energy source. Oil was extracted by the subcritical extraction system. Gas chromatography (GC), ultra-performance liquid chromatography-mass spectrometry (UPLC-MS), and differential scanning calorimetry (DSC) were used to evaluate the fatty acids composition, triacylglycerol (TAG) molecular species, and thermal properties, respectively. It was found that the content of OCFA reached 68.15%, where pentadecanoic acid (7.74%), heptadecanoic acid (18.20%), and heptadecenoic acid (42.71%) were the dominant OCFA. The most abundant TAG were HePaHa (15.82%), HePHa (11.42%), HePaHe (9.68%), HeHaHa (9.62%), HePaO (8.26%), and HePPa (8.00%). In terms of thermal profiles, recrystallization was detected in the oil rich in OCFA. Above all, these findings greatly extend the utilization of the microbial oil rich in OCFA, and they may have a significant impact on the future development of the microbial oil industry.