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Metabolism of fatty acids and their incorporation into phospholipids of the mitochondria and endoplasmic reticulum in isolated hepatocytes determined by isolation of fluorescence derivatives.

Isolated hepatocytes were incubated in the presence of [14C]palmitic, [14C]linoleic or [14C]linolenic acid and the time-courses of incorporation of radioactivity into phosphatidylcholine and phosphatidylethanolamine of microsomes and mitochondria were followed. For this purpose a procedure was developed for HPLC separation of 9-diazomethylanthracene (ADAM) derivatives of fatty acids. When [14C]palmitic acid was used, the major product of elongation and desaturation was octadecadienoic acid, which accounted for 35-65% of the total radioactivity. Labeled palmitoleic, stearic and oleic acids could also be isolated. In fatty acids which do not participate to any large extent in deacylation-reacylation reactions, the pattern of incorporation was characteristic: a high rate of incorporation into microsomal and a low rate of incorporation into mitochondrial phospholipids during the first 40 min, followed by a decrease in the former and an increase in mitochondrial labeling. This pattern is consistent with the fact that de novo synthesis of these two phospholipids occurs in the endoplasmic reticulum in vivo. When cells were incubated in the presence of [14C]linoleic acid, 70-90% of the radioactivity recovered in phospholipids was in this same form, whereas the remaining label was mainly in arachidonic acid and, to some extent, in eicosatrienoic acid. When hepatocytes were incubated in the presence of [14C]linolenic acid, 70-85% of the radioactivity in isolated phospholipids was associated with linolenic acid. As much as 20% of the label was recovered in docosahexanoic acid and 5-10% in arachidonic acid. In the case of the two latter labeled substrates the exchange reactions seem to dominate over de novo synthesis. For phospholipids synthesized de novo the transfer from the endoplasmic reticulum to mitochondria requires about 3 h.

Animals↗

Biosynthesis and regulation of iodolipids in calf thyroid.

The incorporation of 125I into iodolipids was investigated in calf thyroid slices. Time course studies showed that the iodination of lipid reaches a plateau after 30 min of incubation. A highly significant correlation was found between iodination of lipid and of protein (r = 0.906), suggesting that both reactions may be related. Addition of PTU or MMI caused a significant inhibition of lipid iodination, indicating that a peroxidase could be involved in this reaction. The iodinated lipids are not attached to protein, since they migrated in BEA chromatography and pancreatin digestion of the samples did not modify the percentage radioactivity. The iodolipid fraction observed in BEA chromatography was eluted and analysed by TLC. Iodinated free fatty acids and neutral lipids comprised most of the radioactivity. Although iodolipids are present in every subcellular fraction, the 20 000 X g pellet had the greatest proportion of iodinated fatty acids and neutral lipids.

Animals↗

Subcellular distribution of [125I]iodoaryl beta-methyl fatty acids.

Subcellular distribution studies of two aryl branched-chain and one aryl straight-chain iodinated fatty acids were carried out as part of a continuing effort to determine if such acids are metabolized by beta-oxidation. For the omega-iodoaryl fatty acids, a change in subcellular radioactivity location was observed which was chain-length dependent. Chain lengths of 15 carbons, straight and branched, were largely found in the nuclear-membrane fraction, whereas a chain length of 8 carbons was largely located in the cytosol. No unequivocal evidence for metabolic trapping in the mitochondria was observed for omega-iodoaryl branched-chain fatty acids using the centrifugation technique employed in this study.

Animals↗

Polyenoic acid metabolism in cultured dissociated brain cells.

The incorporation of [1-(14)C]linolenate (18:3 n - 3) into cellular lipids of cultured dissociated brain cells was studied. During the initial phases of incubation, radioactivity was found in free fatty acids, diacylglycerols, triacylglycerols, and choline phosphoglyceride pools preferentially. Incorporation into the ethanolamine phosphoglyceride pool increased steadily and paralleled desaturation and chain elongation of 18:3 --> 20:3 --> 20:4 --> 20:5 --> 22:5 --> 22:6. From pulse-chase studies it was evident that the label of the highly polyunsaturated fatty acids in ethanolamine phosphoglycerides is constantly increased while the label in the fatty acids of choline phosphoglycerides decreased. Uptake of 18:3 by the cells was reduced by lowering incubation temperature, the triacylglycerol and ethanolamine phosphoglyceride pools being mainly affected. Lowering the incubation temperatures essentially abolished conversion of labeled 18:3 to the higher polyenoic acids. At intermediate temperatures, conversion of 18:3 to 20:5 n - 3 was still active, but conversion of 20:5 n - 3 to 22:6 n - 3 was abolished, suggesting that formation of 22:6 from 18:3 proceeds by at least two reactions distinguishable by their temperature dependency.

Animals↗

Assessment of myocardial metabolism with iodine-123 heptadecanoic acid: effect of decreased fatty acid oxidation on deiodination.

Terminally radioiodinated fatty acid analogs are of potential use for the noninvasive delineation of regional alterations of fatty acid metabolism by gamma imaging. Since radioactivity from extracted iodine-123 heptadecanoic acid [( 123I]HDA) is released from the myocardium in form of free radioiodide (123I-) the present study was performed to determine whether deiodination of [123I]HDA is related to free fatty acid metabolism. Myocardial production of free radioiodide was measured in rat hearts in vitro and in vivo both under control conditions and after inhibition of fatty acid oxidation. In isolated rat hearts perfused at constant flow with a medium containing [123I]HDA, release of 123I- was markedly reduced during cardioplegia and pharmacologic inhibition of mitochondrial fatty acid transfer with POCA by 67% (p less than 0.005) and 72% (p less than 0.005), respectively. In fasted rats in vivo, 1 min after i.v. injection of [123I]HDA, 51 +/- 5% of myocardial radioactivity was recovered in the aqueous phase, containing free iodide, of myocardial lipid extracts. Aqueous activity was significantly decreased in fed (20 +/- 2%; p less than 0.002) and POCA pretreated (30 +/- 3.7%; p less than 0.05) animals exhibiting reduced oxidation of [14C]palmitate. Thus, deiodination of [123I]HDA was consistently reduced during inhibition of fatty acid oxidation in vitro and in vivo. The results apply to the interpretation of myocardial clearance curves of terminally radioiodinated fatty acid analogs.

Animals↗

Early effects of beta-adrenergic and muscarinic secretagogues on lipid and phospholipid metabolism in guinea pig parotid acinar cells. Stimulation of 2,3-sn-diacylglycerol formation by isoproterenol.

The early effects (0-120 s) of the beta-adrenergic secretagogue isoproterenol (2.10(-5) M) and the muscarinic secretagogue carbamoylcholine (2.10(-6) M) on various parameters of lipid and phospholipid metabolism were studied in isolated guinea pig parotid acinar cells. Both agonists enhanced within 10-20 s the incorporation of radioactive palmitate into the diacylglycerol, the triglyceride, and the phosphatidylinositol fractions but significantly diminished radioactive palmitate recovered in the acyl-CoA fraction. Carbamoylcholine decreased and isoproterenol increased the recovery of radioactive palmitate in the free fatty acid fraction. All changes had returned almost to control levels after 120 s. In cells prelabeled with [3H]arachidonate, carbamoylcholine exerted similar effects, whereas isoproterenol was almost ineffective. Both agonists stimulated the incorporation of radioactive glycerol into diacylglycerols 2-3-fold, while only carbamoylcholine stimulated the incorporation of [32P]phosphate into phosphatidylinositol and phosphatidate. Both agonists induced an increase in total diacylglycerols, carbamoylcholine being about twice as effective as isoproterenol. A lower concentration of carbamoylcholine (6.5.10(-7) M) had the same quantitative effect as 2.10(-5) M isoproterenol on the increase of total diacylglycerols. Even under these conditions carbamoylcholine, but not isoproterenol led to a significant translocation of protein kinase C from the soluble to the particulate fraction. Isoproterenol remained ineffective in this respect also when intracellular free calcium was increased with a calcium ionophore. This is explained by the finding that isoproterenol stimulates preferentially the formation of 2,3-sn-diacylglycerol, and carbamoylcholine preferentially stimulates the formation of 1,2-sn-diacylglycerol. The results indicate that in the guinea pig parotid acinar cell the two agonists do not only lead to activation of a triglyceride lipase (isoproterenol) or phosphoinositide-specific phospholipase(s) (carbamoylcholine), but also to a rapid change of flux through a number of other enzyme-catalyzed reactions involved in diacylglycerol turnover.

Acyl Coenzyme A↗

The effect of glycerol and other intermediates on the incorporation of 14C-fructose and 14C-glucose to hepatic triglyceride.

Mature male rats were given, orally, 14C-fructose either alone or in conjunction with dihydroxyacetone, glyceraldehyde, or glycerol. Glycerol was also administered with 14C-glucose in a dose equimolar with fructose. After 2 hr the rats were killed and the liver triglyceride fraction was separated. Estimations of the degree of incorporation of 14C from the radioactive labeled carbohydrate into the glycerol and fatty acid moieties were carried out. Dihydroxyacetone and glyceraldehyde reduced the incorporation of 14C-fructose into hepatic triglyceride to approximately equal extents, suggesting that both trioses contribute equally to alpha-glycerophosphate formation. Glycerol, however, brought about a profound increase in the amount of fructose converted to triglyceride. This effect of glycerol was not apparent to any measurable extent on glucose incorporation into triglyceride and none of the intermediates affected the proportional distribution of radioactive counts between the fatty acid and glycerol moieties of the triglyceride after 14C-fructose administration.

Animals↗

Specific sites of fatty acid sterol synthesis in isolated skin components.

Metabolic studies on isolated mouse skin components were undertaken to determine the specific sites of fatty acid and sterol synthesis. The concentrations of long-chain fatty acids and sterols and the incorporation of radioactivity from acetate-1-(14)C into these lipids are reported for various skin components and intact whole skin. Only fatty acids having chain lengths of 18 carbons or less were produced by the connective tissue cells of the dermis, while fatty acids containing 20 carbons or more, as well as the acids of 18 carbons or less, were synthesized in the upper dermis (papillary reticulum). The upper dermis also produced significant quantities of eicosenoic acid and of an octadecadienoic acid (not linoleic acid), and incorporated labeled acetate into fatty acids containing an odd number of carbons. Removal of the epidermis and adnexa diminished sterol synthesis. However, the upper region of the dermis was capable of synthesizing, from acetate, large quantities of unidentified nonsaponifiable lipids which were neither sterols nor squalene.

Acetates↗

Fatty acid and cholesterol synthesis from specifically labeled leucine by isolated rat hepatocytes.

Hepatocytes isolated from female rats meal-fed a high-glucose diet were incubated in Krebs-Henseleit bicarbonate medium containing 16.5 mM glucose, 3H2O, and 14C-labeled amino acids (-)-Hydroxycitrate depressed the incorporation of 3H2O and [14C] alanine into fatty acids and cholesterol. Incorporation of [U-14C]leucine into lipids was not affected but incorporation of 3H2O into lipids was decreased significantly by (-)-hydroxycitrate. (-)-Hydroxycitrate depressed the incorporation of radioactivity from [2-14C]leucine into fatty acids and cholesterol by 61 and 38%, respectively, and stimulated the incorporation of radioactivity from [4,5-3H]leucine 35 and 28%. As [2-14C]leucine labels the acetyl-CoA pool and [4,5-3H]leucine labels the acetoacetate pool, it was concluded that mitochondrial 3-hydroxy-3-methylglutaryl-CoA is not incorporated intact into cholesterol, and that acetoacetate can be activated effectively in the liver cytosol for support of cholesterol and fatty acid synthesis.

Acetoacetates↗

Significance of myocardial uptake of iodine 123-labeled beta-methyl iodophenyl pentadecanoic acid: comparison with kinetics of carbon 11-labeled palmitate in positron emission tomography.

BACKGROUND: A radioactively labeled beta-methyl branched fatty acid analog, 123I-15-(p-iodophenyl)-3-methyl pentadecanoic acid (BMIPP), has been developed to probe regional myocardial fatty acid metabolism. However, the significance of BMIPP uptake in the myocardium remains unclear. METHODS AND RESULTS: To evaluate the significance of BMIPP uptake, single-photon emission computed tomography was performed 30 minutes after injection of BMIPP, and 201Tl-labeled single-photon emission computed tomography was taken on a separate day in 10 patients. Findings of BMIPP and 201Tl-labeled imaging were compared with the data obtained from positron emission tomography with 11C-labeled palmitate. The BMIPP uptake (percent of maximum) was significantly correlated with the early uptake (percent) and delayed uptake (percent) of 11C-labeled palmitate (r = 0.659 and r = 0.687, respectively) (p < 0.01 each), whereas it was not significantly correlated with the residual fraction (r = 0.205) or the clearance half-time of the early component (r = 0.138) of 11C-labeled palmitate as a marker of beta-oxidation of the fatty acid. CONCLUSIONS: These data indicate that, although the myocardial uptake of BMIPP may not directly reflect beta-oxidation of fatty acids, its uptake may reflect both regional myocardial blood flow and fatty acid extraction.

Adult↗

Kinetics of radioiodinated species in subcellular fractions from rat hearts following administration of iodine-123-labelled 15-(p-iodophenyl)-3-(R,S)-methylpentadecanoic acid (123I-BMIPP).

It is recognized that iodine-123-labelled 15-(p-iodophenyl)-3-(R,S)-methylpentadecanoic acid (123I-BMIPP) slowly washes out of the myocardium. The mechanism for the washout was investigated in normal rat hearts by analyses of the subcellular distribution and lipid classes based on the BMIPP metabolism. Rat hearts were excised at 1-120 min after intravenous injection of 123I-BMIPP. After counting the radioactivity, the hearts were digested with Nagarse and homogenized, and then fractionated into the cytosolic, mitochondrial, microsomal and crude nuclear fractions by centrifugations. The radioactivity of each fraction was counted, and the lipid classes were analysed by radio-thin-layer chromatographic and high-performance liquid chromatographic methods. The heart uptake of 123I-BMIPP was maximal at 5 min (6.81%+/-0.36% ID/g), and 41% of the radioactivity disappeared within 120 min. The myocardial radioactivity was immediately distributed into the cytosolic, mitochondrial, microsomal and crude nuclear fractions. The distribution (%) of each fraction was almost identical from 5 min through 120 min. The cytosolic fraction was always the major site of radioactivity deposition (60%), and the time-activity curve of the cytosolic fraction paralleled that of the whole heart throughout the 120-min study period. In the cytosolic fraction, most of the radioactivity was incorporated into the triglyceride class, and the rest was present in the free fatty acid, phospholipid (phosphatidylcholine) and diglyceride classes. In the mitochondrial fraction, the radioactivity was mostly incorporated into the phospholipid class (phosphatidylethanolamine), followed by free fatty acids. The final metabolite of 123I-BMIPP, 123I-p-iodophenylacetic acid (123I-PIPA), initially appeared in the mitochondrial fraction as early as 1 min, and subsequently in the cytosolic fraction at 5 min. Another intermediary metabolite, 123I-p-iodophenyldodecanoic acid (123I-PIPC12), was found only in the mitochondrial fraction after 5 min. In conclusion, the slow washout kinetics of 123I-BMIPP from the myocardium mainly reflects the turnover rate of the triglyceride pool in the cytosol. The BMIPP metabolism, i.e. initial alpha-oxidation followed by subsequent cycles of beta-oxidation, was confirmed in vivo. The participation of the mitochondria in the metabolism was also proven.

Animals↗

Syntheses of phosphatidylcholines, sphingomyelins and cholesterol substituted with azido fatty acids. Photocrosslinking with nearest neighbouring lipids in liposomes chemical and mass spectroscopic proof.

The chemical synthesis of azido-substituted saturated, monoenoic and dienoic fatty acids of high specific tritium radioactivity, together with improved methods for their introduction into phosphatidylcholine, sphingomyelin and cholesteryl ester molecules are outlined. Phospholipid vesicles with these photosensitive probes were irradiated and the main crosslinking products isolated and characterized by high resolution mass spectroscopy.

Azides↗

In vitro acylation of rat brain myelin proteolipid protein.

The incorporation of fatty acid into myelin proteolipid protein (PLP) was studied by incubating brain slices from 17-day-old rats with [9,10-3H]palmitic acid. Myelin proteins were analyzed by gel electrophoresis. As in vivo (Agrawal, H. C., Randle, C. L., and Agrawal, D. (1982) J. Biol. Chem. 257, 4588-4592) most of the radioactivity co-migrated with PLP, with radioactivity also appearing in the regions of the DM-20 and Wolfgram proteins. Treatment of myelin proteins or purified PLP with 1 M hydroxylamine released most of the radioactivity, indicating that [3H]palmitic acid was covalently bound by ester linkage to the proteins. Cleavage of PLP with methanolic NaOH and examination of the released fatty acids by thin layer chromatography showed radioactivity associated with the methyl esters of palmitate, stearate, and oleate (76, 23, and 1%, respectively). A linear increase in radioactivity from [3H]palmitic acid was observed in PLP in both myelin and myelin-like fractions, while appearance of [14C]glycine-labeled PLP showed a lag of 45-60 minutes. These results indicate that lipid is added to PLP in the myelin and myelin-like membranes, or immediately prior to the appearance of PLP in these fractions. For both precursors, the specific activity of PLP was greater in the myelin-like fraction than in myelin, indicating that the myelin-like fraction may contain a precursor pool of PLP for myelin.

Acylation↗

The monoglyceride pathway of fat absorption in man.

The absorption of fat was studied in five male subjects with cannulation of the thoracic duct in the neck by the administration of doubly labeled monoglycerides, or triglyceride as well as labeled free glycerol or labeled free oleic acid, by gastric or duodenal intubation.Total recoveries of the administered glyceride radioactivity from the lymph lipids ranged from 35 to 53% for the glycerol label (tritium) and from 35 to 57% for the fatty acid label ((14)C). The recovery of administered radioactive free glycerol in lymph lipids was only 4.1%, even when given in mixture with bile salts, fatty acid, and monoglyceride.A comparison of the isotope ratios of the two components (glycerol and fatty acid) of the lymph glycerides with the ratios of these components of the original meal glyceride showed little change during the initial period of fat absorption, indicating that the doubly labeled monoglycerides passed into the lymph intact. During the later part of the period of major fat absorption, the ratios in lymph lipids changed due to loss of glycerol representation, indicating monoglyceride hydrolysis and portal venous diversion of free glycerol. Confirmation of the intact nature of 2-monoglyceride during absorption was made by analyzing the amount and position of the labeled fatty acid in the lymph triglycerides. The percentage of labeled fatty acid in the various positions of the lymph triglycerides was virtually identical with that of the meal during the initial period of fat absorption and then changed reflecting isomerization of fatty acids and subsequent complete hydrolysis of the glycerides.The 2-monoglyceride pathway appears to be the major route of fat absorption for man during normal digestion and absorption of dietary triglyceride.

Adult↗

Effect of BASF 13-338, a Substituted Pyridazinone, on Lipid Metabolism in Leaf Tissue of Spinach, Pea, Linseed, and Wheat.

A substituted pyridazinone (BASF 13-338) inhibited photosynthesis in spinach (Spinacia oleracea, Hybrid 102 Arthur Yates Ltd.) leaf discs and reduced the incorporation of [1-(14)C]acetate into trienoic acids of diacylgalactosylglycerol while causing radioactivity to accumulate in diacylgalac-tosylglycerol dienoic acids. Although BASF 13-338 inhibited photosynthesis in isolated spinach chloroplasts, it did not prevent dienoate desaturation. In discs, the labeling of fatty acids was affected by the inhibitor only in diacylgalactosylglycerol. Very little radioactivity was incorporated into trienes of phosphatidylcholine and the proportion of the label recovered in the fatty acids of phosphatidylcholine was not changed by BASF 13-338. The herbicides caused an increase in the proportion of the lipid (14)C incorporated into diacylgalactosylglycerol and a decrease in labeling of phosphatidylcholine, whereas the proportion of (14)C recovered in other lipids remained unchanged. Similar results were obtained with pea (Pisum sativum cv. Victory Freeze), linseed (Linum usitatissimum cv. Punjab), and wheat (Triticum aestivum cv. Karamu). With these species, a greater proportion of the label was incorporated into phosphatidylcholine and less into diacylgalactosylglycerol than with spinach. The data indicate that trienoate synthesis uses diacylgalactosylglycerol as substrate. BASF 13-338 appears to act at that step, and seems to cause in spinach a shift in polyenoate synthesis from the pathway involving microsomal phosphatidylcholine to the pathway operating inside the chloroplast.

Journal Article↗

Metabolism of eicosa-11,14-dienoic acid in rat testes. Evidence for delta8-desaturase activity.

The metabolism of [14C]eicosa-11,14-dienoic acid was investigated in rat testes in vivo and in vitro. Intratesticular injection of [1-14C]eicosa-11,14-dienoic acid resulted in the appearance of radioactivity (4-30% of 14C in total fatty acids) in 20-carbon trienoic fatty acids and a small amount (2-3.5%) in arachidonic acid. Analysis of the 20-carbon trienoic acid fraction by ozonolysis indicated that 15 to 34% of the 14C in this fraction was in an 8-carbon fragment originating from eicosa-8,11,14-trienoic acid. The rest (66 to 84%) was in a 5-carbon fragment, presumably originating from eicosa-5,11,14-trienoic acid. Incubation of testicular tissue minces or microsomes with [1-14C]eicosa-11,14-dienoic acid yielded labeled eicosa-8,11,14- and eicosa-5,11,14-trienoic acids in proportions similar to those obtained in vivo. Added unlabeled acetate had no effect on the formation of [14C]eicose-8,11,14-trienoic acid in vitro. Therefore, it is unlikely that the labeled eicosa-8,11,14-trienoic acid arose from elongation of octadeca-6,9,12-trienoic acid with labeled acetate derived from bio-oxidation of the labeled substrate. These results are compatible with a limited desaturation of eicosa-11,14-dienoic acid to eicosa-8,11,14-trienoic acid and provide evidence for delta8 desaturate activity in rat testis.

Acetates↗

Studies on bacillomycin D biosynthesis by Bacillus subtilis.

The biosynthesis of bacillomycin D, an antibiotic containing a beta-amino fatty acid and a peptide moiety with asparagine, glutamic acid, serine, proline, threonine, and tyrosine, was studied by incubating the Bacillus subtilis producer with various 14C-labelled precursors. Sodium acetate was incorporated into beta-amino fatty acids of bacillomycin D, and asparagine was the best precursor of the peptidic moiety. The kinetics of the incorporation of radioactive substrates into bacillomycin D and into beta-amino fatty acids show that the lipid and the peptide moieties of the antibiotic were synthesized at the same stage of growth of the bacteria. Comparing the effects of different inhibitors on the incorporation of radioactive precursors, the bacillomycin D and beta-amino fatty acids biosyntheses are discussed in relation to the biosyntheses of proteins, lipids and with sporulation.

Acetates↗