The purpose of the present study is to examine the oxidative behavior of punicic acid (9 cis, 11 trans, 13 cis-18:3 octadecatrienoic fatty acid) under in vivo condition using male albino rats after blending with dietary soybean oil. Male weanling Charles Foster rats (n = four to eight), weighing 65-68 grams, were allocated for fourteen weeks to diets containing 0.6, 1.2 and 2.4% (by weight) punicic acid obtained from snake gourd seed oil (Trichosanthes anguina) after mixing with soybean oil, vis-à-vis control group consisting of 100% soybean oil, containing 50.3% C18:2, 6.2% 9 cis, 12 cis, 15 cis-18:3 (linolenic acid) and does not contain punicic acid. Increase in weight remained higher than control in rats fed with 0.6 and 1.2% punicic acid throughout the experimental period. There was significant lowering in plasma total cholesterol (TC) and low-density lipoprotein cholesterol (LDL-C) in the groups fed with 2.4% punicic acid. Lipoprotein oxidation susceptibility or LOS expressed as nmoles of malondialdehyde (MDA) per mg of non-high density lipoprotein cholesterol (non-HDL-C) and plasma lipid peroxidation or PLP expressed as nmoles of MDA per ml of plasma exhibited maximum antioxidant efficiency at 1.2% punicic acid, being equivalent to that of control (100% soybean oil). While LOS expressed as nmoles of MDA decreased significantly (except at 2.4% punicic acid level) with the least oxidation at 0.6% punicic acid, with respect to control. Accordingly, punicic acid seemed to be acting both as pro-oxidant (at 1.2% punicic acid level) and antioxidant (at 0.6% punicic acid level), with significant decrease in TC and LDL-C at 2.4% punicic acid level when compared to control.
Examination was made of the amounts and compositions of diacyl glyceryl ethers (DAGE) in various tissue lipids of the deep-sea squid Berryteuthis magister. Liver specimens contained copious amounts of lipids (56.9%) which were composed almost entirely of triacylglycerols (TG: 53.1%) and DAGE (32.4%). Ovary samples contained substantial amounts of lipids (13.9%) with considerable DAGE (8.1%). Mantle, integument and testis samples contained small amounts of lipids (1.0, 1.1 and 1.5%, respectively) with lower DAGE content (0.1%, 0.1% and trace, respectively). In liver and mantle, glyceryl ethers originating in DAGE had essentially the same alkyl chains, whose most predominant component was 16:0 (70.2% and 69.9%) alcohol followed by 18:0 (7.1% and 6.3%), 18:1n-9 (7.4% and 5.9%) and 18:1n-7 (4.5% and 4.6%) alcohols, respectively. Component glyceryl ethers in ovary were characteristically rich in monoenes (52.9%) with 18:1n-9 (24.6%), 20:1n-9 (15.5%) and 18:1n-7 (10.2%) alcohols. Fatty acid compositions of DAGE, TG and phospholipid classes in various tissue lipids of this squid species are discussed.
The filamentous fungus Mortierella alpina was incubated aerobically at 20 °C for two weeks with shaking in a flask containing liquid medium composed of urea, dextrose, and various minerals including KH2PO4, MgSO4·7H2O and CaCl2·2H2O. Urea was found to be as good a source of nitrogen as potato protein only when certain minerals were present in the growth medium. The potassium, phosphorus, and magnesium minerals particularly affected the growth of the fungus. The cell mass yielded was proportional to the amount of KH2PO4 present in the growth medium while only a small amount of MgSO4·7H2O was critical for the growth, although additional amounts of MgSO4·7H2O did not increase the cell mass accordingly. Under mild agitation conditions the fungus grew in pulpy form, however, magnesium sulfate pelleted the fungus in the urea medium when potassium dihydrogenphosphate was present in a KH2PO4/MgSO4·7H2O weight ratio below 1. Lipid-free cells of the uniform pellets remarkably weighed more than the pulpy form and the arachidonic acid content in fatty acids of the pellet was greater, even though the overall level of fatty acids was lower. The results suggested that the lipid-free uniform pellets consumed much glucose leaving a small amount for lipid synthesis and that in the final stage of the incubation starvation of the fungus accelerated the fatty acid conversion to produce arachidonic acid.
Porcine pancreatic lipase (PPL) catalyzed transesterification between tributyrylglycerol and secondary alcohols was studied at 30°C using six 2-alkanols, five 3-alkanols and differrent organic solvents with the solvent hydrophobicity (log P) ranging from -1.1 to 4.5. The plots of the enantioselectivity (as log E, E: the enantiomeric ratio) against carbon number (CN) of 2-alkanol showed the minima at CN = 8 and 9 in the solvents with log P>-0.3 and log P<-0.3, respectively. In the case of 3-alkanol, the plots showed the minima at CN = 9 in the solvents with 3.2≥log P≥2.0 and the E values increased with CN of alcohol for the other solvents. The log E values showed a rough negative correlation with log P and their correlations were different depending on the structure of alcohol. The negative correlation was rationalized by a hydrophobic interaction. Based on the above results, it was concluded that the enantioselectivity was affected by a combination of the substrate structure and the solvent hydrophobicity.
Epoxidation of olefins was successfully achieved using molecular oxygen in the presence of an aldehyde and a catalytic amount of CuCl2 at room temperature. Hexanal was found to be a particularly good reducing agent for the CuCl2-catalyzed epoxidation. A good correlation was observed between the reactivity and the calculated ionization potential for some of the aldehydes tested. The present system was applied to epoxidation of a range of olefins in high to excellent yields.
Determination was made of trans fatty acid content in margarines marketed in Austria, Belgium, Czech Republic, Denmark, Finland, Hungary, Japan, Norway, Poland, Sweden and the United States by gas-liquid and silver-ion thin-layer chromatography carried out in conjunction. As wt% of total fatty acid, it was found that, in print margarines, trans fatty acid was less than 3% in most products of Austria, Finland, Hungary and Sweden. For products of Belgium, trans fatty acid was relatively low, at 4% on the average. In Czech Republic and Denmark, trans fatty acid was divided into two groups of less than 2% and 20% or more. In Japan, Norway, Poland and the United States, trans fatty acid was found to exceed 20%. In tub margarines, trans fatty acid was generally below 3% for Austria, Belgium, Czech Republic, Denmark, Finland, Hungary and Sweden. Japan, Norway, Poland and the United States indicated mean trans fatty acid to be relatively high, at 13-16%, though several brands of low trans fatty acid margarines (below 3%) appear on the market in these countries. In most cases, margarines low in trans fatty acid were rich in saturated fatty acid and the total value of trans and saturated fatty acids (TFA+SFA) was essentially the same in high and low trans fatty acid margarines. Margarines with total cis-polyunsaturated fatty acid (PUFA) to TFA+SFA ratio [PUFA/(TFA+SFA)], above 1, are available as print margarines in Denmark and tub margarines in all the other countries except for Sweden. TFA+SFA content (g/100g) in print margarines in the United States was quite low and tub margarines in Japan were noted to contain considerable TFA+SFA.
Fatty acid compositions of neutral lipids (NL) and polar lipids (PL) have been analyzed for a unique sample of Ophiuroidea (brittle star) Ophiura sarsi containing novel nonmethylene-interruped (NMI) fatty acids, 7E,13E-icosadienoic (20:2), 7E,13E,17Z-icosatrienoic (20:3), 9E,15E,19Z-docosatrienoic (22:3), and 4Z,9E,15E,19Z-docosatetraenoic (22:4) acids. All of the NMI fatty acids were concentrated in NL (mainly triacylglycerols) rather than in PL (mainly phosphatidylcholines and phosphatidylethanolamines). On the other hand, 6,9,12,15,18,21-tetracosahexaenoic acid (24:6n-3) usually observed in Ophiuroidea lipids was found in PL at higher concentration than in NL. Biological property and origin of the novel NMI fatty acids appear to be different from those of 24:6n-3.