ABSTRACT
An unusual fatty acid, cis-9,cis-15-octadecadienoic acid, has been identified in the pulp lipids of mango (Mangifera indica L.) grown in the Philippines. To our knowledge, the occurrence of cis-9,cis-15-octadecadienoic acid in higher plant lipids has not been previously reported. The structure confirmation was based on the results of chromatographic (capillary GC, argentation thin-layer) and spectrometric (GC-MS, infrared, ultraviolet) analysis and chemical treatment. This butylene-interrupted dienoic fatty acid is concentrated in the pulp part of mango fruit and occupies 5.4% of total acyl groups in the pulp lipids; whereas a common octadecadienoic acid, linoleic acid, is a minor component (1.1%) in the same lipids. If a trivial name is desired, it is suggested that cis-9,cis-15-octadecadienoic acid be called "mangiferic" acid.
Subject(s)
Fruit/chemistry , Linoleic Acids/analysis , Chromatography, Gas , Gas Chromatography-Mass Spectrometry , Isomerism , Linoleic Acids/chemistry , Philippines , SpectrophotometryABSTRACT
The long-chain fatty acid composition in rat liver, by which peroxisomal beta-oxidation system was induced, was analyzed in vitro and in vivo. In primary culture of hepatocytes, treatment with 0.4 mM clofibrate or long-chain fatty acids caused an increase in the peroxisomal beta-oxidation activity, in addition the oleic acid [18:1(n-9)] content in the cells was increased two-fold by addition of very long-chain fatty acids to the culture medium, but clofibrate had no effect. A two-fold of increase in 18:1(n-9) content was observed in the hepatic subcellular fractions from rats fed a diet containing 0.25% clofibric acid. The ratio of cis-vaccenic acid [18:1(n-7)] to total 18:1 content decreased by more than half compared with control in clofibric acid treated liver. The level of 18:1(n-7) was not changed in all experiments. It is suggested that perturbation of C-18 chain length fatty acids occurs in peroxisomal beta-oxidation induced liver.
Subject(s)
Fatty Acids/metabolism , Liver/metabolism , Microbodies/metabolism , Animals , Body Composition/physiology , Clofibrate/pharmacology , In Vitro Techniques , Liver/drug effects , Male , Oxidation-Reduction , Rats , Rats, Wistar , Subcellular Fractions/drug effects , Subcellular Fractions/metabolismABSTRACT
Vibrio sp. strain ABE-1 was grown in a medium that contained as its stable isotope tracer either [2,2-2H2]cis-9-hexadecenoic or [2,2-2H2]trans-9-hexadecenoic acid. Gas chromatographic-mass spectrometric analysis of the cis-9-hexadecenoic and trans-9-hexadecenoic acid fractions from the cells revealed the formation of an intracellularly isomerized 2,2-2H2-fatty acid which differed from the tracer only in the geometrical configuration of the double bond. This observation shows that cis-trans isomerization without a shift in double-bond position between these two geometric hexadecenoic acid isomers can occur in the cells.
Subject(s)
Fatty Acids, Unsaturated/chemistry , Vibrio/chemistry , Mass Spectrometry , StereoisomerismABSTRACT
The novel pathways of oleic acid formation from cis-vaccenic (cis-11-octadecenoic) acid and of cis-vaccenic acid formation from oleic acid by enzymatic positional isomerization have been proposed in higher plants, based on stable-isotope experiments using [2,2-2H2]cis-vaccenate or [2,2-2H2]oleate as an immediate precursor. A pulp homogenate and also pulp slices prepared from developing kaki (Diospyros kaki) fruit could catalyze these hitherto unknown isomerizations. This suggests the presence of a new type of isomerase responsible for the double-bond shifting reaction without cis-trans isomerization in the middle of fatty acid carbon chains.
Subject(s)
Oleic Acids/biosynthesis , Plants/metabolism , Chemical Phenomena , Chemistry , Isomerases/metabolism , Isomerism , Oleic Acid , Plants/enzymologyABSTRACT
Tocopherol, one of the antioxidants in vegetable fats and oils, was added to the autoxidized diet of male rats at the same tocopherol level as soybean oil before autoxidation. Autoxidized soybean oil was used as the test lipid; fresh soybean oil was the control. The diet containing autoxidized oil depressed the body weight gains and increased the tissue ratios to body weight, with the exception of testicle. Parallel with those, increased hemolysis, peroxide value and carbonyl value in the tissue lipids, and a decrease in linoleic or arachidonic acid was observed. The effect of dietary vitamin E on the tissue lipid peroxidation was different among the individual organs. From the results obtained by chemical analyses, the lipid peroxidation caused in the liver, heart and intestine was recognized to be suppressed effectively when the same tocopherol level as fresh soybean oil was added to the diet.
Subject(s)
Plant Oils/toxicity , Soybean Oil/toxicity , Vitamin E/pharmacology , Animals , Diet , Erythrocytes/drug effects , Fatty Acids/analysis , Fatty Acids/blood , Fatty Acids/metabolism , Hemolysis/drug effects , Kidney/drug effects , Kidney/metabolism , Lipid Metabolism , Liver/drug effects , Liver/metabolism , Male , Organ Size/drug effects , Oxidation-Reduction , Rats , Rats, Inbred Strains , Soybean Oil/analysis , Testis/drug effects , Testis/metabolism , Time FactorsABSTRACT
Ferricyanide reduction catalyzed by vitamin K-3 was accompanied by the decrease in intracellular (NAD(P)H concentration of yeast cells, and the rate of ferricyanide reduction depended on intracellular concentration of NADH rather than NADPH. The addition of glucose to the cell suspensions enhanced both ferricyanide reduction and intracellular NADH concentration. The catalytic action of vitamin K-3 on ferricyanide reduction was observed in the presence of NADH and plasma membrane preparations. As the toxic action of vitamin K-3 on cell growth of yeast was enhanced by addition of ferricyanide, ferricyanide reduction catalyzed by vitamin K-3 may inhibit cell growth by decreasing intracellular NADH concentration.
Subject(s)
Ferricyanides/metabolism , NAD/analysis , NADP/analysis , Oxidation-Reduction , Saccharomyces cerevisiae/metabolism , Vitamin K/pharmacologyABSTRACT
Microsomal NADPH-dependent lipid peroxidation catalyzed by ADP-Fe3+ was inhibited by the addition of caeruloplasmin. The antioxidant effect of caeruloplasmin was independent of the superoxide anion (O-2) scavenging activity. Since caeruloplasmin enhanced the function of ADP-Fe3+ acting as electron acceptor for microsomal electron transport system, the antioxidant effect of caeruloplasmin is considered to depend on the ferroxidase activity.
Subject(s)
Antioxidants , Ceruloplasmin/pharmacology , Lipid Peroxides/metabolism , Microsomes, Liver/metabolism , Animals , Horses , In Vitro Techniques , Male , Microsomes, Liver/drug effects , Oxidation-Reduction/drug effects , Rats , Rats, Inbred StrainsABSTRACT
The antioxidant effect of His-Cu (Histidine and cupric ion) on NADPH-dependent lipid peroxidation was proportional to the inhibitory effect on cytochrome c reduction i the presence of microsomes and ADP-Fe (ADP and ferric ion). The inhibiton of cytochrome c reduction by His-Cu caused no inhibition of NADPH oxidation. ADP-Fe stimulated NADPH oxidation in the absence of cytochrome c, and inhibited cytochrome c reduction. His-Cu inhibited NADPH-oxidation stimulated by ADP-Fe, but the antioxidant effect of His-Cu was independent of the effect on cytochrome b5 reduction. These results suggest that the antioxidant effect of His-Cu depends on the inhibitory effect on the electron transport from NADPH-cytochrome c reductase to ADP-Fe, but not on the inhibitory effect on the activity of the reductase.
