Two kinds of oils, pure perilla oil and a blend of perilla oil with palm oil, and their enzymatically interesterified oils having the same fatty acid compositions but with different compositions of triacylglycerol (TAG) species, were studied. In particular, the effects of TAG molecular species on the oxidation resistance of oils containing α-linolenic acid (Ln) were investigated. The content of TAG binding to three Ln molecules (3Ln-TAG) was found to be different between perilla oil (38.7%) and the interesterified oils (14.5-28.9%) , which were generated using Lipozyme RM-IM® (regiospecificity: sn-1, 3 positional). Oils with lower 3Ln-TAG contents were more stable to oxidation as determined by the conductometric determination method (CDM; 90°C, 20 L/h) than oils with higher 3Ln-TAG contents. This result was also supported by heating oxidation tests (180°C, 7 h) using the interesterified blended oils; the residual ratio of Ln-TAGs in the oils was found to be in the order of 3Ln-TAG<2Ln-TAG<1Ln-TAG. Oxidation stability of Lipase OF® (regiospecificity: random)-interesterified blended oils also improved on lowering the 3Ln-TAG content. In addition, the oxidation stabilities of Lipozyme RM-IM®-interesterified oils were slightly higher than those of the Lipase OF®-interesterified oils. We found that the content of 3Ln-TAG was almost the same in both oils, and the content of unsaturated fatty acid at the sn-1, 3 positions of Lipase OF®-interesterified oils was higher than that of Lipozyme RM-IM®-interesterified oils. These results indicate that oxidation stabilities of oils containing TAG with unsaturated fatty acid such as Ln at sn-2 position were higher than those having unsaturated fatty acids at the sn-1, 3 positions. From these results, the oxidation stability of oils rich in Ln, such as perilla oil and linseed oil, can be improved not only by decreasing 3Ln-TAG but also by enzymatically reducing the unsaturated fatty acid content at the sn-1, 3 positions.
Previously, we reported a new preparation method for liposomes and niosomes (nonionic vesicles) using supercritical carbon dioxide (scCO2) as the solvent (scRPE method). In this study, niosomes were prepared from polyglycerol fatty acid ester (PG ester)-type nonionic surfactants. These surfactants are made from naturally derived materials and are neither harmful to the human body nor to the environment. Niosomes were prepared using the scRPE method with ethanol as the co-solvent. Through this method, decaglycerol distearate (DG2S) and decaglycerol diisostearate (DG2IS) formed niosomes. On the other hand, decaglycerol monostearate (DG1S), which has a high hydrophilic-lipophilic balance (HLB) value, yielded a solution of spherical micelles, and decaglycerol tristearate (DG3S), which has a low HLB value, yielded a gel-like solution. Niosomes of DG2IS had higher trapping efficiencies and dispersion stabilities than those of DG2S because the membrane fluidity of the DG2IS niosomes was greater than that of the DG2S niosomes. The niosomes obtained in the present study are candidates for cosmetic and pharmaceutical applications because they are formed from nonionic surfactants derived from natural sources, and prepared using the scRPE method, which avoids the use of harmful organic solvents.
In this study, diacylglycerol-enriched soybean oil (DESO) was synthesized through Lipozyme 435-catalyzed glycerolysis of soybean oil (SO) in a solvent-free system using a modified bubble column reactor. The effects of enzyme load, mole ratio of glycerol to soybean oil, reaction temperature, gas flow and reaction time on DAG production were investigated. The selected conditions were established as being enzyme load of 4 wt% (mass of substrates), glycerol/soybean oil mole ratio of 20:1, reaction temperature of 80°C, gas flow of 10.6 cm/min, and a reaction time of 2.5 h, obtaining the DAG content of 49.4±0.5 wt%. The reusability of Lipozyme 435 was evaluated by monitoring the contents of DAG, monoacylglycerol (MAG) and triacylglycerol (TAG) in 10 consecutive runs. After purified by one-step molecular distillation, the DAG content of 63.5±0.3 wt% was achieved in DESO. The mole ratio of 1, 3-DAG to 1, 2-DAG was 2:1 and the fatty acid composition had no significant difference from that of soybean oil. However, the thermal properties of DESO and SO had considerable differences. Polymorphic form of DESO were mainly the β form and minor amounts of the β′ form. Granular aggregation and round-shaped crystals were detected in DESO.
Fish oil is composed of various fatty acids among which omega-3 fatty acids are considered as most beneficial. The effects of fish oil on the activity of a topical anticancer drug, imiquimod, and the immunomodulatory activity of omega-3 fatty acids was investigated in human basal and squamous cell carcinoma cell lines. Imiquimod-fish oil mixture exhibited higher carcinoma cell growth inhibition and immunomodulatory activity than imiquimod alone, especially against squamous cell carcinoma cells. Omega-3 fatty acids exhibited growth inhibition of both basal cell and squamous cell carcinoma cell lines and modulated the immune response. Omega-3 fatty acids of fish oil serve as inducers of interleukin-10, an anti-inflammatory cytokine, and as suppressors of interleukin-6 and tumor necrosis factor-alpha, which not only depress tumor growth but also adequately control the inflammatory side effects of imiquimod. Thus, imiquimod administration with fish oil could be beneficial for inhibition of non-melanoma skin carcinoma cells but further in vivo studies are needed to understand their role in skin cancer.
Iron deficiency anemia (IDA) is one of the most common nutritional disorders in the world. In the present study, we evaluated erythrocyte membrane fatty acid composition in premenopausal patients with IDA. Blood samples of 102 premenopausal women and 88 healthy control subjects were collected. After the erythrocytes were separated from the blood samples, the membrane lipids were carefully extracted, and the various membrane fatty acids were measured by gas chromatography (GC). Statistical analyses were performed with the SPSS software program. We used blood ferritin concentration <15 ng/mL as cut-off for the diagnosis of IDA. The five most abundant individual fatty acids obtained were palmitic acid (16:0), oleic acid (18:1, n-9c), linoleic acid (18:2, n-6c), stearic acid (18:0), and erucic acid (C22:1, n-9c). These compounds constituted about 87% of the total membrane fatty acids in patients with IDA, and 79% of the total membrane fatty acids in the control group. Compared with control subjects, case patients had higher percentages of palmitic acid (29.9% case versus 25.3% control), oleic acid (16.8% case versus 15.1% control), and stearic acid (13.5% case versus 10.5% control), and lower percentages of erucic acid (11.5% case versus 13.6% control) and linoleic acid (15.2% case versus 15.4% control) in their erythrocyte membranes. In conclusion, the total-erythrocyte-membrane saturated fatty acid (SFA) composition in premenopausal women with IDA was found to be higher than that in the control group; however, the total-erythrocyte-membrane unsaturated fatty acid (UFA) composition in premenopausal women with IDA was found to be lower than that in the control group. The differences in these values were statistically significant.
Numerous studies have shown that dietary omega-3 polyunsaturated fatty acids (PUFAs), particularly eicosapentaenoic acid (EPA), improve lipid metabolism. The beneficial effects of PUFA-derived oxidation products have been increasingly reported. However, EPA is easily oxidized in food products and in the human body, generating various derivatives of oxidized EPA (oxEPA), such that these oxidation products may partially contribute to EPA’s effect. We previously reported that oxEPA was more potent than intact EPA in reducing liver-X-receptor α (LXRα)-induced cellular triacylglycerol (TG) accumulation. However, the in vivo hypolipidemic effects of oxEPA remain unclear. In the present study, we evaluated the effect of oral administration of EPA and oxEPA on hepatic steatosis in mice induced by a high-sucrose diet and a synthetic LXRα agonist, TO-901317. Both EPA and oxEPA reduced TG accumulation in the liver and plasma biomarkers of liver injury. Furthermore, they suppressed the expression of lipogenic genes, but not β-oxidation genes, in a similar pattern as the biomarkers. Our results suggest that oxEPA and intact EPA suppress de novo lipogenesis to ameliorate hepatic steatosis.
Lathyrus species including L. ochrus and L. sativus are known for their food, feed and horticultural uses. Despite their widespread uses and cultivation, there is limited information on their chemistry. Previously, only the essential oil composition of L. rotundifolius, L. vernus and volatiles of L. odoratus have been reported. In the present research, volatiles of seven Lathyrus L. species, namely, L. aphaca, L. ochrus, L. cicera, L. sativus, L. gorgonei, L. saxatilis and L. blepharicarpos var. cyprius were analyzed by SPME GC-MS for the first time. Plant materials were collected from five different locations in Cyprus (February-March 2012). The main components of L. aphaca volatiles from four locations were yomogi alcohol 26.1-16.5%, camphor 21.6-10.1%, tetradecane 14.3-0%; L. cicera from five locations were yomogi alcohol 20.3-3.0%, camphor 18.7-2.0%; L. gorgonei from two locations were yomogi alcohol 24.5-13.1%, camphor 17.1-9.0% and L. sativus was yomogi alcohol 11.4%, camphor 9.0%. Yomogi alcohol was not present as the major compound in L. ochrus (2-methyl butanoic acid 7.2%), L. saxatilis (hexanal 7.7%) and L. blepharicarpos var. cyprius ((Z)-3-hexenal 8.6%) volatiles. The volatiles of the Lathyrus species were also compared with each other quantitative and qualitatively using AHC analysis to find out differences among the species. The irregular monoterpene yomogi alcohol is reported from the Lathyrus and the Leguminosae family for the first time. The existence of yomogi alcohol in Lathyrus volatiles points out that the irregular monoterpenes are not restricted solely to Asteraceae family.
Glyceric acids (GAs) esterified with long acyl chains (> C16) exhibit antitrypsin activity (Folia Microbiol. 46, 21-23 (2001)). However, their hydrophobic nature, derived from the long acyl chains, has limited the number of studies on their physical and biological properties. To improve the water solubility of diacyl GAs, GA was esterified with octanoyl groups (C8), and its physical properties were investigated. Synthesized dioctanoyl GA was not water-soluble, whereas its sodium salt was. Surface tension measurements of dioctanoyl GA sodium salt (diC8GA-Na) in water revealed that the critical micelle concentration (CMC) was 0.82 mM, and surface tension at the CMC was 25.5 mN/m. Additionally, diC8GA-Na inhibited casein digestion by trypsin to a greater extent than dioleoyl GA. These data suggest that water-soluble diacyl GAs may have utility as surfactants and bioactive compounds.
To improve the productivity of Paraphoma-like fungal strain B47-9 for biodegradable plastic (BP)-degrading enzyme (PCLE), the optimal concentration of emulsified poly(butylene succinate-co-adipate) (PBSA) in the medium was determined. Emulsified PBSA was consumed as a sole carbon source and an inducer of PCLE production by strain B47-9. Among the various concentrations of emulsified PBSA [0.09–0.9% (w/v)] used in flask cultivation, 0.27% yielded the maximum enzyme activity within a short cultivation period. To evaluate the residual concentration of emulsified PBSA in culture, emulsified PBSA in aliquots of culture supernatant was digested in vitro, and the concentration of released monomerised succinic acid was determined. Regardless of the initial concentration of emulsified PBSA in medium, PCLE activity was detected after residual succinic acid decreased below 0.04 mg/mL in culture broth. Jarfermentation was performed at a 0.27% PBSA concentration. Among the various airflow rates tested, 1 LPM resulted in a PCLE production rate of 1.0 U/mL/day. The enzyme activity in the resulting culture filtrate (4.2 U/2 mL) was shown to degrade commercial BP films (1 × 1 cm, 20 µm thickness) within 8 hours.
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