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The present article studies the transformations and fractionation of the reserve lipids of Ricinodendron heudelotii. The native triglycerides of this oil are composed mainly of conjugated polyunsaturated fatty acids, in particular α-eleostearic acid C18:3 n– 5 (9c, 11t, 13t) at 60%. This particular fatty acid of CLnA family exerts many activities potentially beneficial for health: anti-inflammatory, anti-leukemic, anti-microbial, anti-tumor, anti-ulcer and anti-diabetic. A process for transforming this acid into its isomers β-eleostearic acid and catalpic acid was explored with the aim of obtaining fractions enriched in β-eleostearic acid C18:3 n– 5 (9t, 11t, 13t). The β-eleostearic acid is a fatty acid of great interest because it is even more reactive and more efficient as antioxidant than α-eleostearic acid due to its higher trans content. Isomerization reaction of α-eleostearic acid in oil was carried out using artificial solar radiation treatment. The enrichment of concentrates in β-eleostearic acid was therefore tested using an eco-fractionation process. This process was carried out in two stages. The first step was the Candida rugosa lipase-catalyzed hydrolysis of triglycerides from native or isomerized Ricinodendron heudelotii oil. The second step was fractionation of the reaction medium obtained after hydrolysis. Triglyceride hydrolysis was complete, with a yield of free fatty acids of over 95% after 2 h of reaction. Treatment of the reaction media yielded 3 lipid concentrates with new chemical compositions of polyunsaturated fatty acids: a first concentrate, derived from hydrolysis of the native oil, composed of 60% α-eleostearic acid and 22% linoleic acid, and two other concentrates derived from fractionation of the hydrolysate of the oil isomerized by radiation. One was composed of 34% linoleic acid, 21% β-eleostearic acid, 11% α-eleostearic acid and 6% catalpic acid, and the last concentrate was composed of over 80% β-eleostearic acid. In addition to offering nutritional benefits similar to those of α-eleostearic acid, β-eleostearic acid also offers an interesting physical property: a very high melting point of 72 °C. Such a polyunsaturated fatty acid, which is solid at room temperature, could prove to be a raw material of choice, particularly in the world of food formulation, where manufacturers are looking for replacements with physical properties close to those of palm oil (the melting point of palmitic acid is 62 °C). Ricinodendron heudelotii oil has thus demonstrated its major role as a source of the triptych of α-eleostearic, β-eleostearic and linoleic fatty acids. [ABSTRACT FROM AUTHOR]

以超临界CO2萃取的苦瓜籽油为原料，经皂化酸解法制得混合脂肪酸，再采用尿素包合法富集其中的α-桐酸。在单因素试验的基础上，采用正交试验对富集工艺条件进行优化。结果表明，α-桐酸的最佳富集工艺条件为：采用95%乙醇作为尿素溶剂，混合脂肪酸与尿素质量比1∶ 3，尿素与95%乙醇质量比1∶ 5，包合温度4 ℃，包合时间24 h。在最佳工艺条件下，α-桐酸纯度从苦瓜籽油中的28.83%提高至60.03%，产物中共轭亚麻酸相对含量达到71.28%。Using bitter gourd seed oil extracted by supercritical CO2 as raw material, the mixed fatty acid was obtained by saponification and acid hydrolysis, and then the α-eleostearic acid was enriched by urea adduction fractionation. Based on single factor experiment, the enrichment conditions were optimized by orthogonal experiment. The results showed that the optimal process for enriching α- eleostearic acid from bitter gourd seed oil were obtained as follows: with 95% ethanol as urea solvent, mass ratio of mixed fatty acid to urea 1∶ 3, mass ratio of urea to 95% ethanol 1∶ 5, adduction temperature 4 ℃ and adduction time 24 h. Under these conditions, the purity of α- eleostearic acid increased from 2883% (in bitter gourd seed oil ) to 60.03%, the total relative content of conjugated linolenic acid in the product reached 71.28%.

Abstract The tung tree (Vernicia fordii) is a non-edible oil plant native to southern China and was introduced in Japan in the nineteenth century. The tree produces tung oil, which is composed of approximately 80% α-eleostearic acid (9c, 11t, 13t-octadecatrienoic acid), 7% linoleic acid, and 6% oleic acid. Tung oil may be a non-edible source of biodiesel fuel (BDF) production. The iodine value (IV) is one of parameters to guarantee BDF quality, and the most common method for the determination of IV is the Wijs method. The IV can be calculated from the average molecular weight and the number of double bonds from the GC–MS data. In this study, the IVs of olive, castor, soybean, linseed, and perilla BDF using the Wijs method were found to be almost the same as the calculated IV. On the other hand, the IV of tung BDF by the Wijs method indicated a significantly lower value than that of the calculated value. To determine the cause of this discrepancy, the samples before and after halogenation using the Wijs method, were analyzed by 1H NMR. The conjugated double bond signals did not disappear, and a broad double bond signal remained in the tung BDF spectrum after halogenation. These results demonstrated that iodine, with a large atomic radius, could not react completely with the three conjugated double bonds in α-eleostearic acid. Therefore, the IV of tung BDF was significantly lower than the calculated value.

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Parinaric and α-eleostearic acids are unusual conjugated fatty acids. Unusual fatty acids, in general, are known to have roles in defense response; however, the role of parinaric acid in I. balsamina is not known, nor is it known whether it occurs in different species of Impatiens or its closest monotypic relative, Hydrocera triflora (L.) Wight & Arn. The aim of the study was to (a) characterize the fatty acid composition of 21 species of Impatiens and H. triflora and (b) determine whether parinaric and α-eleostearic acids are present in these taxa and, if so, (c) whether there is interspecific and intraspecific variation in parinaric acid content. Fatty acid profiling was done using gas chromatography and mass spectrometry (GC–MS). To uncover taxonomic patterns of variation in fatty acids, principal component analysis and hierarchical cluster analysis were performed. The major fatty acids in Impatiens were found to be palmitic (5.57–20.85%), stearic (2.86–21.61%), oleic (2.79–28.99%), linoleic (C18:2Δ9,12, 2.04–26.64%), α-linolenic (C18:3∆9,12,15; 11.07–53.99%), and four forms of parinaric acid (5.93–70.21%). Genus Impatiens contains two unusual conjugated fatty acids- parinaric and α-eleostearic, however these are absent in closely related H. triflora. This study reports the presence of four different forms of parinaric acid in Impatiens for the first time. Some species (I. mengtszeana, I. racemulosa and I. oppositifolia) were found to contain very high levels (> 50%) of parinaric acid and they might be useful for various biomedical and industrial applications. Apparently, the presence of parinaric acid is a characteristic of Impatiens. Significant variations were found in the amount and forms of parinaric acid. We propose the potential application of parinaric acid and α-eleostearic acid as chemotaxonomic markers for Impatiens. [ABSTRACT FROM AUTHOR]

The tung tree (Vernicia fordii) is a non-edible oil plant native to southern China and was introduced in Japan in the nineteenth century. The tree produces tung oil, which is composed of approximately 80% α-eleostearic acid (9c, 11t, 13t-octadecatrienoic acid), 7% linoleic acid, and 6% oleic acid. Tung oil may be a non-edible source of biodiesel fuel (BDF) production. The iodine value (IV) is one of parameters to guarantee BDF quality, and the most common method for the determination of IV is the Wijs method. The IV can be calculated from the average molecular weight and the number of double bonds from the GC–MS data. In this study, the IVs of olive, castor, soybean, linseed, and perilla BDF using the Wijs method were found to be almost the same as the calculated IV. On the other hand, the IV of tung BDF by the Wijs method indicated a significantly lower value than that of the calculated value. To determine the cause of this discrepancy, the samples before and after halogenation using the Wijs method, were analyzed by 1H NMR. The conjugated double bond signals did not disappear, and a broad double bond signal remained in the tung BDF spectrum after halogenation. These results demonstrated that iodine, with a large atomic radius, could not react completely with the three conjugated double bonds in α-eleostearic acid. Therefore, the IV of tung BDF was significantly lower than the calculated value. [ABSTRACT FROM AUTHOR]

Prunus serotine oil, was extracted from the seeds without shells, resulting in an oil yield of 23.41 ± 3.62%. Through GC it was shown that 52.38% of the total fatty acids present in the oil were polyunsaturated fatty acids. The fatty acids profile presented in the P. serotine oil were oleic (41.42%), linoleic (26.97%) and α-eleostearic acid (25.33%). It had a high concentration of total phenols (221 ± 15.85 mg as gallic acid equivalents/kg oil) and flavonoids (0.77 ± 0.01 mg catechin equivalents/kg oil). The antiradical activity was 31.52 ± 2.71% and 12.94 ± 0.67% of radical inhibition for colorimetric methods using ABTS [2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid)] and DPPH (2,2-diphenyl-1-picrylhydrazyl), respectively. The activity inhibition was 2.3 (ABTS) and 1.8 (DPPH) times higher, respectively, than the ones of Prunus dulcis oil. Lipid oxidation showed that at day nine, P. serotine oil has it maximum hydroperoxide production through two methods (hydroperoxide and MDA). Three oregano fractions were added (code: 642, 655 and A01) as natural antioxidants at four different concentrations (3000, 300, 30 and 3 ppm) each one, to extend its shelf life. Fraction 642 managed to extend its shelf life until day 30 (30 °C ± 2 °C), in both methodologies. The fraction 642 at 3 ppm, controls the production of hydroperoxide formation. Resulting in values of 3.65 µM equivalents of cumene hydroperoxide/kg of oil and 10.29 µM equivalents of 1,1,3,3-Tetraethoxypropane/kg of oil, decreasing by 3.2 times the peroxide formation with respect to P. serotine oil without leaving a Poliomintha longiflora fraction. [ABSTRACT FROM AUTHOR]

Copyright of China Journal of Oral & Maxillofacial Surgery is the property of Shanghai Jiao Tong University, College of Stomatology and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

In this study, seed oils of Thladiantha nudiflora and Thladiantha dubia were found to contain 55.5 and 44.4% mole of conjugated octadecatrienoic fatty acids, respectively. The presence of moieties of conjugated fatty acids was confirmed by a series from physical methods: UV, IR, 1H and 13C NMR. The triacylglycerols (TAGs) isolated of the seed oils were studied by RP-HPLC with diode array and mass spectrometric detections. It was shown that all 15 TAGs of Thladiantha dubia contain moieties of conjugated fatty acids -- punicic, (9Z,11E,13Z)-octadeca-9,11,13-trienoic acid (35.6% mole) and 8.9% mole α-eleostearic, (9Z,11E,13E)-octadeca-9,11,13-trienoic acid. Meanwhile, 24 TAGs of Thladiantha nudiflora seed oil contain both acids in approximately equal proportions (27.4:28.2 % mole). The enrichment for polyunsaturated fatty acids of the hydrolysis product of the seed oils due to urea inclusion complex formation was discussed. [ABSTRACT FROM AUTHOR]

With the significant attention paid to α‐eleostearic acid (α‐ESA) in a variety of biologically beneficial effects, the demand for high‐concentration products is increasing. A method of cryogenic separation to predict the mass variation of α‐ESA from tung oil was established in this study. The results showed that the best α‐ESA crystallization condition was −20 °C in ethanol, which implied a low energy consumption when compared with the common crystallization temperature of −60 °C. The α‐ESA concentration in the liquid phase was reduced by 90.4% compared to tung oil, and most of the α‐ESA in the solution was recovered by mass transfer. On the other hand, a mathematical model based on the diffusion reaction theory is used in mass variation prediction. The effects of temperature and time on the mass variation in α‐ESA in solution crystallization were examined. The results showed that the proposed model could estimate the composition and total mass of winterized tung oil at R2=0.974. The model was validated by experiments with an error of ±10%. [ABSTRACT FROM AUTHOR]

A new spectrophotometric assay was developed to measure, continuously and specifically, phospholipase A1 (PLA1) or phospholipase A2 (PLA2) activities using synthetic glycerophosphatidylcholines (PCs) containing α-eleostearic acid, either at the sn-1 position [1-α-eleostearoyl-2-octadecyl-rac-glycero-3-phosphocholine (EOPC)] or at the sn-2 position [1-octadecyl-2-α-eleostearoyl-rac-glycero-3-phosphocholine (OEPC)]. The substrates were coated onto the wells of microtiter plates. A nonhydrolyzable ether bond, with a non-UV-absorbing alkyl chain, was introduced at the other sn position to prevent acyl chain migration during lipolysis. Upon enzyme action, α-eleostearic acid is liberated and then solubilized into the micellar phase. The PLA1 or PLA2 activity was measured by the increase in absorbance at 272 nm due to the transition of α-eleostearic acid from the adsorbed to the soluble state. EOPC and OEPC differentiate, with excellent accuracy, between PLA1 and PLA2 activity. Lecitase®, guinea pig pancreatic lipase-related protein 2 (known to be a PLA1 enzyme), bee venom PLA2, and porcine pancreatic PLA2 were all used to validate the assay. Compared with current assays used for continuously measuring PLA1 or PLA2 activities and/or their inhibitors, the development of this sensitive enzymatic method, using coated PC substrate analogs to natural lipids and based on the UV spectroscopic properties of α-eleostearic acid, is a significant improvement.

An approach specific for triacylglycerides (TAGs) is proposed for chromatographic separation of compounds with different chromophores using spectrophotometric detection instead of preliminary calibration of the detector using unavailable (or difficultly accessible) reference standards. A wavelength similar to an isosbestic point (278 nm) is found for this approach for TAGs containing radicals of three isomeric conjugated octadecatrienoic acids (COAs) and can be used to determine the ratio of the amounts of TAGs with isomeric radicals without introducing correction factors for the sensitivity of each compound. A mathematical procedure for processing UV spectra of TAGs containing COA radicals is proposed for finding these points. The specifics of the TAG composition allow the isolation and use of highly labile pure compounds to be avoided. The method is developed using seed oils of red valerian (Centranthus DC.), TAGs of which are formed from two isomeric COAs (α- and β-eleosteric), and pomegranate (Punica granatum L.) with radicals of another pair of COAs (punicic and α-eleostearic) as examples. [ABSTRACT FROM AUTHOR]

Copyright of Alexandria Journal of Food Science & Technology is the property of Egyptian National Agricultural Library (ENAL) and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

In this study, α-eleostearic acid-loaded (α-ESA-loaded) dimyristoylphosphatidylcholine (DMPC) liposomes had their physicochemical properties characterized by horizontal attenuated total reflectance Fourier transform infrared (HATR-FTIR) spectroscopy, nuclear magnetic resonance (NMR) and differential scanning calorimetry (DSC). In vitro thiobarbituric acid reactive substance (TBARS) assays were performed to obtain preliminary information on the oxidative potential of the system. An α-ESA-promoted ordering effect in the lipid phosphate region was observed. It was associated with a rotation restriction due to an increase in the amount of lipid group hydrogen bonds. The fatty acid was responsible for the reduction in the degree of hydration of carbonyl groups located in the interfacial region of lipids. α-ESA disordered the DMPC methylene acyl chains by trans - gauche isomerization and increased its rotation rate. TBARS results showed pro-oxidant behavior on liposomes, induced by α-ESA. The discussion about the responses considered the degree of saturation of phosphatidylcholines and suggested that the α-ESA oxidative effects may be modulated by the liposome lipid composition. The versatility of liposomal carriers may be promising for the development of efficacious α-ESA-based drug delivery systems. Results described in this study contribute to the selection of adequate material to produce them. [ABSTRACT FROM AUTHOR]

Lipases are essentially described as sn -1 and sn -3 regio-selective. Actually few methods are available to measure this lipase regio-selectivity, moreover they require chiral chromatography analysis or specific derivations which are discontinuous and time consuming. In this study we describe a new, convenient, sensitive and continuous spectrophotometric method to screen lipases regio-selectivity using synthetic triglycerides (TG) containing α-eleostearic acid (9 Z , 11 E , 13 E -octadecatrienoic acid) either at the sn -1 position [1-α-eleostearoyl-2,3-octadecyl- sn- glycerol ( sn -EOO)] or at the sn -3 position [1,2-octadecyl-3-α-eleostearoyl- sn -glycerol ( sn -OOE)] and coated onto the wells of microtiter plates. A non-hydrolysable ether bond, with a non UV-absorbing alkyl chain, was introduced at the other sn positions to prevent acyl chain migration during TG synthesis or lipolysis. The synthesis of TG containing α-eleostearic acid was performed from S -glycidol in six steps to obtain sn -EOO and in five steps to sn -OOE. The α-eleostearic acid conjugated triene constitutes an intrinsic chromophore and, consequently, confers the strong UV absorption properties of this free fatty acid as well as of the TG harboring it. The lipase activity on coated sn -EOO or sn -OOE was measured by the increase in the absorbance at 272 nm due to the transition of α-eleostearic acid from the adsorbed to the soluble state. Human and porcine pancreatic lipases, guinea pig pancreatic lipase related protein 2, Thermomyces lanuginosus lipase, Candida antarctica lipase A and Candida antarctica lipase B were all used to validate the assay. This continuous high-throughput screening method could determine directly without any processes after lipolysis the regio-selectivity of various lipases. [ABSTRACT FROM AUTHOR]

In our previous report, an 80% ethanol bitter gourd seed extract (BGSE) was found to suppress proliferation of adult T-cell leukemia (ATL) cell lines. The present study aimed to identify the bioactive compounds from BGSE specific against ATL. From the result of an HPLC-MS analysis, α-eleostearic acid (α-ESA) was present in BGSE at 0.68% ± 0.0022% (±SD, n = 5). In the cell proliferation test, α-ESA potently suppressed proliferation of two ATL cell lines (ED and Su9T01; IC50 = 8.9 and 29.3 µM, respectively) more than several other octadecanoic acids. However, α-ESA moderately inhibited phytohemagglutinin-activated human peripheral blood mononuclear cells (PBMC; IC50 = 31.0 µM). These results suggest that BGSE-derived α-ESA has potential as a functional food constituent because of its activity against ATL, particularly against ED cells. Moreover, α-ESA might be effective for the prevention of moderate adverse effects of ATL on normal T cells.

We previously reported that bitter melon seed oil (BMSO) was an effective anti-steatosis and antiobesity agent. Since the major fatty acid α-eleostearic acid (α-ESA) in BMSO is a peroxisome proliferator-activated receptor α (PPARα) activator, the objective was to investigate the role of PPARα in BMSO-modulated lipid disorders and α-ESA metabolism. C57BL/6J wild (WD) and PPARα knockout (KO) mice were fed a high-fat diet containing BMSO (15% soybean oil + 15% BMSO, HB) or not (30% soybean oil, HS) for 5 weeks. The HB diet significantly reduced hepatic triglyceride concentrations and increased acyl-CoA oxidase activity in WD, but not in KO mice. However, regardless of genotype, body fat percentage was lowered along with upregulated protein levels of uncoupling protein 1 (UCP1) and tyrosine hydroxylase, as well as signaling pathway of cAMP-dependent protein kinase and AMP-activated protein kinase in the white adipose tissue of HB-treated groups compared to HS cohorts. In WD-HB and KO-HB groups, white adipose tissue had autophagy, apoptosis, inflammation, and browning characteristics. Without PPARα, in vivo reduction of α-ESA into rumenic acid was slightly but significantly lowered, along with remarkable reduction of hepatic retinol saturase (RetSat) expression. We concluded that BMSO-mediated anti-steatosis depended on PPARα, whereas the anti-adiposity effect was PPARα-independent. In addition, PPARα-dependent enzymes may participate in α-ESA conversion, but only have a minor role. [ABSTRACT FROM AUTHOR]

α-Eleostearic acid (α-ESA), or the cis-9, trans-11, trans-13 isomer of conjugated linolenic acid, is a special fatty acid present at high levels in bitter melon seed oil. The aim of this study was to examine the effect of α-ESA on hepatic lipid metabolism. Using H4IIEC3 hepatoma cell line, we showed that α-ESA significantly lowered intracellular triglyceride accumulation compared to α-linolenic acid (LN), used as a fatty acid control, in a dose- and time-dependent manner. The effects of α-ESA on enzyme activities and mRNA profiles in H4IIEC3 cells suggested that enhanced fatty acid oxidation and lowered lipogenesis were involved in α-ESA-mediated triglyceride lowering effects. In addition, α-ESA triggered AMP-activated protein kinase (AMPK) activation without altering sirtuin 1 (SIRT1) protein levels. When cells were treated with vehicle control (VC), LN alone (LN; 100μmol/L) or in combination with α-ESA (LN+α-ESA; 75+25μmol/L) for 24h, acetylation of forkhead box protein O1 was decreased, while the NAD(+)/NADH ratio, mRNA levels of NAMPT and PTGR1 and enzyme activity of nicotinamide phosphoribosyltransferase were increased by LN+α-ESA treatment compared to treatment with LN alone, suggesting that α-ESA activates SIRT1 by increasing NAD(+) synthesis and NAD(P)H consumption. The antisteatosis effect of α-ESA was confirmed in mice treated with a high-sucrose diet supplemented with 1% α-ESA for 5weeks. We conclude that α-ESA favorably affects hepatic lipid metabolism by increasing cellular NAD(+)/NADH ratio and activating PPARα, AMPK and SIRT1 signaling pathways. [ABSTRACT FROM AUTHOR]

The native crude oil of Ricinodendron heudelotii mainly consists of triglycerides formed typically with polyunsaturated fatty acids (84%). Fatty acids with three conjugated double bonds (Conjugated Linolenic Acids, CLnA) contain more than 60% of α-eleostearic acid (C18:3 9c, 11 t, 13 t). The heat-treating process using the traditional hulling method of seeds for kernel consumption results in the isomerization of α-eleostearic acid into β-eleostearic and catalpic acid. In order to gather information about the transformation of these conjugated polyunsaturated fatty acids, a study to investigate the effects of solar radiation on the native oil was conducted. Changes in the chemical composition of fatty acids in the oil, especially conjugated polyunsaturated fatty acids, were monitored by GC (Gas Chromatography). Analysis of fatty acid profiles of treated and untreated oils showed the isomerization of α-eleostearic acid under the effect of solar radiation, whether natural or artificial. This isomerization involves the conversion of α-eleostearic acid into its isomers β-eleostearic acid (C18:3 9 t, 11 t, 13 t) and catalpic acid (C18:3 9 t, 11 t, 13c) with a ratio of 5:1 in the triglycerides of the oil. Our findings highlight the significant influence of solar radiation on composition and isomerization of the fatty acids of Ricinodendron heudelotii oil, and emphasize as well as its potential use in the industrial production of some CLnA isomers. [Display omitted] • CLnA isomerization in Ricinodendron heudelotii oil under natural or artificial solar radiations. • Isomerization of α-eleostearic acid into β-eleostearic acid and catalpic acid. • The ratio of β-eleostearic acid to catalpic acid formed is about 5:1. [ABSTRACT FROM AUTHOR]

The objective of the present study was to fabricate and monitor real-time, impact of a stable conjugated linolenic acid, α-eleostearic acid (ESA) rich nanoemulsion (NE) formulation ( d < 200 nm) vis-à-vis ESA conventional emulsion (CE) system in ex vivo systems against both endogenous and exogenous reactive oxygen species (ROS). Accordingly, stable nanoemulsion formulation of ESA was engineered with the aid of bitter melon seed oil and non-toxic excipients. Morphology and particle size of the emulsion formulations were studied to validate stability. The real-time rapid uptake of the ESA NE and its increased prophylactic efficacy against induced endogenous and exogenous ROS in terms of cell viability and membrane integrity was evaluated flow-cytometrically and with fluorescence microscopic analysis of different primary cells. It was found that the fabricated non-toxic ESA NE had stable parameters (hydrodynamic mean diameter, particle size distribution and zeta potential) for over 12 weeks. Further, ESA NE at a concentration of ∼70 μM exhibited maximum efficacy in protecting cells from oxidative damage against both endogenous and exogenous ROS in lymphocytes and hepatocytes as compared to its corresponding presence in the CE formulation. This study provides a real-time empirical evidence on the influence of nano formulation in enhancing bioavailability and antioxidative properties of ESA. [ABSTRACT FROM AUTHOR]

Seed oils with high polyunsaturated fatty acid content are used in various industries including the food and pharmaceutical industries. White mahlab ( Prunus mahaleb L.) seed was found to contain 31% oil. The oil was highly polyunsaturated and abundant in α-eleostearic (38.32%), oleic (31.29%), and linoleic (22.96%) acids, which together comprised 93.91% of the total fatty acids. The α-eleostearic acid was identified and characterized based on 1H-NMR, UV, and FTIR spectroscopy. The oil was characterized by a relatively high quantity of tocopherols with γ-tocopherol as the major tocopherol isomer. The physicochemical characteristics of the white mahlab seed and seed oil were also determined. The thermogravimetric analysis indicated that the oil was thermally stable up to 350 °C and began to decompose at 520 °C. This study demonstrated that these seeds may be reused and their oil incorporated into other food products, a beneficial practice considering that the compounds present in the seeds and oils have positive effects on human health. Practical Application In this study, mahlab seed oil was found to have potentials to become a new edible oil source as it contained a high level of polyunsaturated fatty acids especially, α-eleostearic acid, which is a conjugated fatty acid rarely found in vegetable oils and has a beneficial effects on human health. [ABSTRACT FROM AUTHOR]

Highlights: [•] α-Eleostearic acid antioxidant effect was correlated to changes in lipid dynamics. [•] α-Eleostearic acid orders lipid polar/interfacial groups, as shown by FTIR and NMR. [•] α-Eleostearic acid may restrict the OH diffusion toward polar/interfacial region of the membrane. [•] α-Eleostearic acid disorders the lipid non-polar region, as shown by FTIR and DSC. [•] The lipid disorder may facilitate α-eleostearic acid and free radical interactions. [Copyright &y& Elsevier]

An increment approach and the control of the position of convergence points is proposed for the determination of the fatty acid composition of triacylglycerides ( TAGs) from seed oil of pomegranate. reversed-phase HPLC under conditions ensuring the absence of artifacts is shown to distinguish TAGs formed by isomer-conjugated octadecatrienic acids. [ABSTRACT FROM AUTHOR]

Dietary oils containing large amounts of conjugated linolenic acids (CLnA) may be regarded as a source of conjugated linoleic acids (CLA), which have been suspected to bear health-promoting properties. Indeed, CLnA can be converted into CLA in mammals. The objective of the present study was to investigate the uptake of CLnA and their metabolism into CLA in Caco-2 cells, as a validated in vitro model of the intestinal barrier. Caco-2 cells were incubated for 24 h in the presence of either α-eleostearic, β-eleostearic, catalpic or punicic acid. We first observed that Caco-2 cells take these CLnA up at different rates and then convert them but with varying efficiency depending on the structure of the Δ13 double bond. Finally, the distribution of CLnA between neutral lipids (NL) and phospholipids appeared to be linked to their number of trans double bonds: the higher the number, the higher the accumulation in the NL fraction. [ABSTRACT FROM PUBLISHER]

Abstract: The present study was undertaken to evaluate under in vivo condition the effects of α-linolenic acid and α-eleostearic acid against methyl mercury (MeHg) induced oxidative stress. Male albino rats were divided into six groups. Group 1 was under normal control and Group 2 was treated with methyl mercury chloride (MeHgCl; 5mg/kgBW/day). Groups 3, 4, 5 and 6 were orally treated with different doses of the two fatty acids (0.5% and 1.0% of total lipid given for each kind of linolenic acid isomer) along with MeHgCl (5mg/kgBW). Comet assay of blood lymphocytes showed that administration of α-linolenic acid reduced DNA damage significantly (P <0.05). Results also showed that activity of antioxidant enzymes of plasma and brain tissue and total antioxidant capacity in plasma decreased significantly due to oxidative stress generated by MeHgCl. Administration in higher dose of both kind of linolenic acid restored all the activities of the antioxidant enzymes and also reduced lipid peroxidation and increased total antioxidant capacity in plasma. Both kinds of linolenic acid successfully maintained the RBC membrane integrity which was totally disrupted and became flat due to MeHgCl stress. α-Linolenic acid was more efficient antioxidant than α-eleostearic acid against oxidative DNA damage. [Copyright &y& Elsevier]

Aim of study: The purpose of the study was to evaluate hypolipidemic and hypocholesterolemic activities of conjugated linolenic acid (CLnA) isomers, present in bitter gourd and snake gourd seed, in terms of amelioration of plasma lipid profile, lipoprotein oxidation and erythrocyte membrane fluidity after oral administration. Methods: Male albino rats were divided into six groups. Group 1 was control, and others were induced with oxidative stress by oral gavage of sodium arsenite (Sa). Group 2 was kept as treated control, and groups 3-6 were further treated with different oral doses of seed oils to maintaining definite concentration of CLnA isomers (0.5 and 1.0% of total lipid for each CLnA isomer). Results: CLnA isomers normalized cholesterol, LDL-cholesterol, HDL-cholesterol and triglyceride contents in plasma and body weight of experimental rats and decreased cholesterol synthesis by reducing hepatic HMG-CoA reductase activity. Administration of Sa caused alteration in erythrocyte membrane fluidity due to increase in cholesterol and decrease in phospholipid content. Tissue cholesterol and lipid contents were also increased by Sa administration. These altered parameters were reversed by experimental oil administration. Protective effect of CLnA isomers on erythrocyte morphology was observed by atomic force microscopy (AFM). Fatty acid composition of erythrocyte membrane showed decrease in polyunsaturated fatty acid (PUFA) and increase in arachidonic acid content after Sa administration, which was normalized with the treatment of these oils. Supplementation of CLnA isomers restored erythrocyte membrane (EM) lipid peroxidation and lipoprotein oxidation. Conclusion: CLnA isomers, present in vegetable oils, showed potent hypolipidemic and hypocholesterolemic activities against biochemical perturbations. [ABSTRACT FROM AUTHOR]

Abstract: The present study was undertaken to evaluate the effect of α-linolenic acid and α-eleostearic acid, two isomers of linolenic acid, against oxidative stress induced by organic mercury in kidney and liver cells of rat. Male albino rats were divided into six groups. Groups 1, 2 were normal control and methyl mercury chloride (MeHgCl) treated (5mg/kg BW/day) control, respectively. Groups 3, 4, 5 and 6 were orally treated with different doses of two fatty acids (0.5% and 1.0% of total lipid given for each isomer) along with MeHgCl (5mg/kg BW). Results showed that activity of antioxidant enzymes viz. catalase (CAT), superoxide dismutase (SOD), glutathione peroxidase (GPx), reduced glutathione (GSH) in liver and kidney decreased significantly due to oxidative stress generated by MeHg. Administration of the linolenic acid isomers almost restored all the altered parameters and also reduced lipid peroxidation and leakage of trans-aminase enzymes from liver to blood due to liver injury when administrated in higher doses. Histopathology of liver and kidney cells showed that administration of α-linolenic acid significantly reduced the damage generated by MeHg. Thus, α-linolenic acid and α-eleostearic acid could serve as cost-effective and natural phytochemical preparation to protect against the adverse effects caused by organic mercury in human. [Copyright &y& Elsevier]

Abstract: The purpose of the present study was to examine the antioxidant activity of two typical oils obtained from two vegetables, bitter gourd seed and snake gourd seed, containing two different isomers of conjugated linolenic acid (CLnA) against oxidative stress induced by sodium arsenite in relation to tissue lipid peroxidation and inflammation. Male albino rats were taken as subject and divided into six groups: Group 1 was control and Group 2 was treated with sodium arsenite (Sa; 10mg/Kg BW); Groups 3–6 were orally treated with different doses of seed oils maintaining definite concentration of CLnA isomers (0.5% and 1.0% of total lipid for each CLnA isomer) along with sodium arsenite. There was significant increase in lipid peroxidation, pro-oxidant enzyme activity and decrease in antioxidant enzyme activity in brain due to Sa administration. Decrease in total protein content was also observed in plasma, liver and brain of Sa treated group. Significant decrease in phospholipid content and increase in total lipid content and cholesterol content were observed in arsenite treated group. There was significant increase in relative organ weight of liver due to Sa administration. Fatty acid profile of liver and brain lipid shows significant (P <0.05) reduction in most of the polyunsaturated fatty acids and increase in arachidonic acid (20:4n-6) (75.23%) due to inflammation after arsenite treatment. Administration of experimental oils made almost complete restoration of those altered parameters. Overall, these two oils were effective in protecting tissue lipid profiles which were altered due to oxidative stress. [Copyright &y& Elsevier]

Abstract: The present study was undertaken to evaluate the ameliorative role of α-eleostearic acid and punicic acid, isomers of conjugated linolenic (CLnA) acid, against oxidative stress induced DNA damage. Male albino rats were divided into six groups. Group 1 and 2 were normal control and sodium arsenite treated (Sa; 10mg/kgBW) control respectively. Group 3–6 were orally treated with different doses of two fatty acids (0.5% and 1.0% of total lipid given for each isomer) along with sodium arsenite (Sa; 10mg/kgBW). Comet assay of blood leukocytes showed that administration of CLnA reduced DNA damage significantly (P <0.05) which was determined by tail DNA percent and olive tail moment. Results showed that activity of antioxidant enzymes viz. catalase, superoxide dismutase (SOD), glutathione peroxidase (GPx) and reduced glutathione (GSH) in plasma, liver and erythrocyte lysate decreased and activity of nitric oxide synthase in plasma and liver increased significantly due to oxidative stress generated by sodium arsenite. Administration of CLnA isomers restored all the altered parameters and also reduced lipid peroxidation and leakage of transaminase enzymes from liver to blood due to liver injury. α-Eleostearic acid was more efficient antioxidant than punicic acid against oxidative DNA damage. [ABSTRACT FROM AUTHOR]

Abstract: The present study was undertaken to evaluate the antioxidant efficacy of α-eleostearic acid and punicic acid, two isomers of conjugated linolenic acid, in terms of normalization of altered biochemical parameters of oxidative stress following sodium arsenite treatment in rats. Animals were divided into four groups. The first group used as control. While, group 2, 3 and 4 were orally treated with α-eleostearic acid (0.5% of total lipid given) plus sodium arsenite (Sa; 10mg/kgBW), punicic acid (0.5% of total lipid given) plus sodium arsenite (Sa; 10mg/kgBW) and sodium arsenite (Sa; 10mg/kgBW), respectively. Results showed that activities of antioxidant enzymes decreased significantly due to oxidative stress generated by sodium arsenite. Lipid peroxidation also increased due to sodium arsenite administration. α-Eleostearic acid and punicic acid acted as antioxidant and caused mostly all the altered parameters restored to normal level. Results also showed that antioxidant activity of α-eleostearic acid was more predominant than that of punicic acid. [Copyright &y& Elsevier]

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. [ABSTRACT FROM AUTHOR]

Abstract: Conjugated linolenic acids (CLN) refer to a group of octadecatrienoic acids with three conjugated double bonds. Minor positional and geometrical differences among CLN isomers make their separation and identification difficult. We have used GC–MS and NMR to study three common CLN isomers namely α-eleostearic acid, β-eleostearic acid and punicic acid, finding that some signals of olefinic carbon atoms in NMR spectra were mistakenly assigned in the literature. The present study was therefore undertaken to re-characterize the location of Cbonds and assign the chemical signals of proton and carbon atoms using 1H NMR, 13C NMR, 1H–1H two-dimensional correlation spectra (1H–1H COSY) and 13C–1H two-dimensional correlation spectra (13C–1H COSY). The geometrical structure of double bonds in these three CLN isomers was identified using homonuclear decoupling technique. [Copyright &y& Elsevier]

Abstract: Expression of Δ12-oleic acid desaturase-related fatty acid conjugases from Calendula officinalis, Momordica charantia, and Vernicia fordii in seeds of soybean (Glycine max) or an Arabidopsis thaliana fad3/fae1 mutant was accompanied by the accumulation of the conjugated fatty acids calendic acid or α-eleostearic acid to amounts as high as 20% of the total fatty acids. Conjugated fatty acids, which are synthesized from phosphatidylcholine (PC)-linked substrates, accumulated in PC and phosphatidylethanolamine, and relative amounts of these fatty acids were higher in PC than in triacylglycerol (TAG) in the transgenic seeds. The highest relative amounts of conjugated fatty acids were detected in PC from seeds of soybean and A. thaliana that expressed the C. officinalis and M. charantia conjugases, where they accounted for nearly 25% of the fatty acids of this lipid class. In these seeds, >85% of the conjugated fatty acids in PC were detected in the sn-2 position, and these fatty acids were also enriched in the sn-2 position of TAG. In marked contrast to the transgenic seeds, conjugated fatty acids composed <1.5% of the fatty acids in PC from seeds of five unrelated species that naturally synthesize a variety of conjugated fatty acid isomers, including seeds that accumulate conjugated fatty acids to >80% of the total fatty acids. These results suggest that soybean and A. thaliana seeds are deficient in their metabolic capacity to selectively catalyze the flux of conjugated fatty acids from their site of synthesis on PC to storage in TAG. [Copyright &y& Elsevier]

Abstract: α-Eleostearic acid is one of the conjugated linolenic acids from tung oil, which is obtained from the seeds of Aleurites fordii. The effects of dietary α-eleostearic acid (18:3, n-5) on the post-initiation period of 7,12-dimethylbenz[a]anthracene (DMBA) and 1,2-dimethylhydrazine (DMH)-induced mammary and colon carcinogenesis were examined using female Sprague–Dawley (SD) rats. For initiation, rats were given subcutaneous injections of 40mg/kg body weight (5 times) and 20mg/kg body weight (3 times) of DMH during the age of 6–8 weeks and a single intragastric administration of 50mg/kg body weight of DMBA at 9 weeks. Then, the animals were treated with 0%, 0.01%, 0.1% or 1.0% α-eleostearic acid for 34 weeks. Control rats received the basal diet alone or 1.0% α-eleostearic acid without prior initiation treatment. All surviving animals were killed at week 37 of the experiment. There were no statistically significant alterations in any of the parameters for either mammary or colon tumors. These results thus indicate that α-eleostearic acid does not exert clear modification effects on DMBA and DMH-induced mammary and colon carcinogenesis, at least under the present experimental conditions. [Copyright &y& Elsevier]

Triacylglycerols of the seed oil of Trichosanthes kirilowii have been resolved by high-performance liquid chromatography (HPLC) in the silver-ion and reverse-phase modes. The fatty acids were identified by gas chromatography/mass spectrometry as the picolinyl esters. The main components are cis,cis-C18:2n-6 (38.2 mole%), C18:3 (punicic acid, 38.0 mole%), and cis-C18:1n-9 (11.8 mole%). Small amounts of C18:3 (α-eleostearic acid) and C18:3 (catalpic acid) were detected. Silver-ion HPLC exhibited excellent resolution in which fractions were resolved on the basis of the number and configuration of double-bonds. In this instance, the strength of interaction of a conjugated trienoic double-bond system with silver ions seemed to be between that of dienoic and monoenoic double bond systems. The triacylglycerols were also separated into 20 fractions by reverse-phase HPLC, and the fractionation was achieved according to the partition number in which a conjugated trienoic double bond was not equivalent to three monoenoic double bonds in a molecule with a given chainlength. The principal triacylglycerol species are (C18:2n-6) (C18:3) (28.3 mol% of total), (C18:1n-9)(C18:2n-6) (C18: 3) (19.0 mol%), and (C18:2n-6)(C18:3) (16.2 mol%), while simple triacylglycerols such as (C18:3) and (C18:2n-6) were present as minor components only (<1.0 mol%). Species esterified with conjugated trienoic acids comprise more than 96% of the total. Stereospecific analysis gave rise to insurmountable difficulties, but it is evident that there is some asymmetry in the distribution of fatty acids in the molecules. [ABSTRACT FROM AUTHOR]

Cherry seed oil, from the Rosaceae family, prunoid subfamily, is characterized by the existence of about 10% α-eleostearic acid. The structure of the acid was proven by H andC nuclear magnetic resonance. The triacylglycerols of this oil were identified and quantitated by highperformance liquid chromatography by means of several types of detectors. α-Eleostearic acid was not found in the seeds of previously studied prunoids (almond, peach, apricot and plum). The main fatty acids found in the seeds of cherry and other prunoids were linoleic (L), oleic (O) and palmitic acids, and the major triacylglycerols were LLO, LOO and OOO. These chemical data support the botanical relationship within the prunoid subfamily and show the proximity of cherry to the Chrysobalanaceae family. [ABSTRACT FROM AUTHOR]

• Hens fed conjugated linolenic acids accumulated approximately 550 mg rumenic acid per egg. • Conjugated linolenic acids did not affect docosahexaenoic acid synthesis in hens. • Dietary α-eleostearic acid accumulation in egg yolks was limited. • Dietary punicic acid significantly accumulated in eggs. • α-Eleostearic acid appears better converted than punicic acid to rumenic acid. The health promoting omega-3, -7, and -5 fatty acids, α-linolenic acid (ALA), docosahexaenoic acid (DHA), rumenic acid (RmA), and α-eleostearic acid (α-ESA)/punicic acid (PunA), are not currently combined in frequently consumed food items. We have evaluated the impact of supplementing laying hens' feeds with flaxseeds combined with oil derived from seeds of either Ricinodendron heudelotii , an α-ESA source, or Punica granatum , a PunA source, on the egg fatty acid profile. The supplemented diets increased the egg content in ALA, DHA, RmA, as well as α-ESA or PunA. The combination of dietary lipids did not affect the conversion rate of ALA into DHA. Hens fed on R. heudelotii or P. granatum seed oil both accumulated RmA in egg yolk, indicating an efficient conversion from the α-ESA or PunA precursors through a Δ-13 reductase activity. The accumulation of PunA in eggs was largely higher than that of α-ESA. [ABSTRACT FROM AUTHOR]

Polyhydroxyalkanoates (PHAs) are attractive new bioplastics for the replacement of plastics derived from fossil fuels. With their biodegradable properties, they have also recently been applied to the medical field. As poly(3-hydroxybutyrate) produced by wild-type Ralstonia eutropha has limitations with regard to its physical properties, it is advantageous to synthesize co- or terpolymers with medium-chain-length monomers. In this study, tung oil, which has antioxidant activity due to its 80% α-eleostearic acid content, was used as a carbon source and terpolymer P(53 mol% 3-hydroxybytyrate-co-2 mol% 3-hydroxyvalerate-co-45 mol% 3-hydroxyhexanoate) with a high proportion of 3-hydroxyhexanoate was produced in R. eutropha Re2133/pCB81. To avail the benefits of α-eleostearic acid in the tung oil-based medium, we performed partial harvesting of PHA by using a mild water wash to recover PHA and residual tung oil on the PHA film. This resulted in a film coated with residual tung oil, showing antioxidant activity. Here, we report the first application of tung oil as a substrate for PHA production, introducing a high proportion of hydroxyhexanoate monomer into the terpolymer. Additionally, the residual tung oil was used as an antioxidant coating, resulting in the production of bioactive PHA, expanding the applicability to the medical field. [ABSTRACT FROM AUTHOR]

In this study, seed oils of Thladiantha nudiflora and Thladiantha dubia were found to contain 55.5 and 44.4% mole of conjugated octadecatrienoic fatty acids, respectively. The presence of moieties of conjugated fatty acids was confirmed by a series from physical methods: UV, IR, 1 H and 13 C NMR. The triacylglycerols (TAGs) isolated of the seed oils were studied by RP-HPLC with diode array and mass spectrometric detections. It was shown that all 15 TAGs of Thladiantha dubia contain moieties of conjugated fatty acids - punicic, (9Z,11E,13Z)-octadeca-9,11,13-trienoic acid (35.6% mole) and 8.9% mole α-eleostearic, (9Z,11E,13E)-octadeca-9,11,13-trienoic acid. Meanwhile, 24 TAGs of Thladiantha nudiflora seed oil contain both acids in approximately equal proportions (27.4:28.2 % mole). The enrichment for polyunsaturated fatty acids of the hydrolysis product of the seed oils due to urea inclusion complex formation was discussed.

The seeds of Couepia longipendula contain 74.2% oil. Gas chromatography (GC) and gas chromatography/ mass spectrometry (GC/MS) of the methyl esters and oxazoline derivatives of the fatty acids and ultraviolet (UV), infrared (IR),H-nuclear magnetic resonance (NMR) andC-NMR spectra of the oil showed the presence of palmitic (25.2%), palmitoleic (0.9%), stearic (6.2%), oleic (26.5%), vaccenic (0.4%), linoleic (7.4%), arachidic (0.3%), α-eleostearic (11.3%) and α-licanic (21.8%) acids. Licanic acid methyl ester was isolated by thin-layer chromatography (TLC) and theC-NMR andH-NMR data are presented. [ABSTRACT FROM AUTHOR]

• Oil from kernels isolated by traditional heat treatment has an iodine value of 180. • Oil from mechanically dehulled kernels has a high iodine value of 194. • α-eleostearic acid is isomerized into β-eleostearic and catalpic acids. • Oils rich in CLnA have beneficial effects on human health. The aim of this study was to characterize the lipids present in the oil and kernels of Ricinodendron heudelotii seeds. Two dehulling methods were used to extract kernels from their husks: a heat treatment and a manual mechanical dehulling technique. Oil from kernels obtained by traditional heat treatment of seeds had a kinematic viscosity of 169 ± 0.5 mPa.s, and an iodine value of 175.6 ± 1.1 g/100 g oil. The oil from kernels isolated by mechanical dehulling had a kinematic viscosity of 128 ± 0.11 mPa.s and an iodine value of 195.2 ± 2.0 g/100 g oil. Determination of the minor compound profile of the oil revealed a total tocopherol content of 135.0 ± 0.4 mg oil from kernels isolated by traditional heat treatment. The oil obtained from kernels isolated by manual mechanical dehulling had a total tocopherol content of 178.3 ± 0.4 mg/100 g. An analysis of the fatty-acid profile of the oil from kernels isolated by traditional heat treatment revealed the presence of α-eleostearic acid (50.5% ±0.1), linoleic acid (24.0% ±0.0), β-eleostearic (8.4% ±0.0) and catalpic acid (0.40% ±0.1). By contrast, the fatty acid composition of oil from kernels isolated by manual mechanical dehulling was of α-eleostearic acid (60.1% ±0.2), linoleic acid (22.8% ±0.1). Ricinodendron heudelotii oil has a very high level (84.4 ± 0.4%) of polyunsaturated fatty acids (CLnA). Some analysis of the triglycerides present in the oil revealed the potential isomerization of α-eleostearic acid to form β-eleostearic acid and catalpic acid. [ABSTRACT FROM AUTHOR]