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PubMed2001

[GC-MS analysis of supercritical carbon dioxide extract from seeds of Zanthoxylum bungeanun Maxim].

The chemical components of supercritical carbon dioxide extracts from seeds of Zanthoxylum bungeanun Maxim. were studied by GC-MS-DS. Thirty-five compounds which account for 96.22% of the total area of the chromatographic peaks, were identified. The results showed that fatty acids and esters occupied 90.83% of total chromatographic efflux of the extracts. The main components of the extracts are oleic acid(38.91%), palmitic acid (29.45%), linoleic acid methyl ester(10.80%), linolenic acid methyl ester(8.64%), et al.

Carbon Dioxide↗
PubMed2001

[GC-MS analysis of supercritical carbon dioxide extraction products from pericarp of Zanthoxylum bungeanum].

The chemical constituents of supercritical carbon dioxide extraction products from pericarp of Zanthoxylum bungeanun Maxim. were studied by GC-MS-DS. Forty-five compounds which account for 86.76% of the area of the chromatographic peaks were identified. The results showed that the main components of the extracts are beta-pinene (10.33%), 1,8-terpinene (7.6%), cis-piperitol acetate (7.07%), oleic acid (5.46%), palmitic acid (5.41%) and 4-terpineol, (43.7%), et al.

Carbon Dioxide↗
PubMed2001

[Organic acid constituents from the stem of Securidaca inappendiculata Hassk].

OBJECTIVE: To investigate the organic acid constituents from the stem of Securidaca inappendiculata. METHOD: Column chromatographic techniques were used to isolate and purify the constituents. The structures were elucidated by spectra analysis. RESULT: Five compounds were isolated and identified as ferulic acid (I), cinnamic acid(II), palmitic acid(III), salicylic acid(IV) and benzoic acid(V). CONCLUSION: Compounds I-IV were isolated from the plant for the first time.

Cinnamates↗
PubMed2004

[Establishment of an immunological labelling of pigs using synthetic peptides].

The objective of this study was to develop a suitable combination consisting of synthetic peptides, carrier protein and adjuvant for immunological labelling of pigs. Specific antibody titres were evaluated by ELISA technique. From 9 peptides 4 were excluded from following investigations showing cross reactivity or low immunogenic effects, sufficient anti-peptide titres were achieved by 5 peptides. Labelling control is possible after 7 days at the earliest and can be used for the whole fattening period after single immunization using an effective carrier-adjuvant-combination. Mixing of peptides in one labelling dose had no negative influence on titres against single peptides. Different combinations of 4 carriers (keyhole limpet haemocyanin (KLH), palmitic-acid-3-cystein-acid (Pam3Cys), palmitic acid (Pam) and dextran) and 4 adjuvants (Montanide IMS 1313, Montanide ISA 25, Quil A and Diluvac forte) were tested. Optimal labelling could be seen by combination of 50 nmol peptide, KLH as carrier and Montanide IMS 1313 as adjuvant. Generally after booster injection titres were higher, however, a booster dose was not necessary using most effective adjuvants. A less immunogenic, but cost effective alternative for short time labelling (7 weeks) was a peptide-Pam3Cys-conjugate (75 nmol) combined with Quil A as an adjuvant (2 mg/ml). Immunological labelling of pigs is recommended as a good method for tracing back the origin of animals and meat products. It may be also used for vaccine labelling to prove vaccination of pigs.

Adjuvants, Immunologic↗
PubMed1993

Identification of the hydrophobic ligand-binding region in recombinant glutathione S-transferase P and its binding effect on the conformational state of the enzyme.

Recombinant glutathione S-transferase P (GST-P) was purified in a homogeneous state. Fatty acid analysis of the enzyme revealed that the final enzyme preparation endogenously bound fatty acids, mostly palmitic acid or stearic acid, which were difficult to dissociate from the complex. Temperature-dependent analysis by 1H NMR indicated that the molecular motion of fatty acids was strongly restrained under physiological conditions, which was significantly different from that of serum albumin. On the other hand, there existed another hydrophobic ligand-binding region in GST-P, to which 1-amino-8-naphthalenesulfonic acid and bilirubin would bind with relatively lower affinity than the endogenously bound fatty acid. The hydrophobic ligand-binding region was determined to be around 141-156 residues from the N-terminus by procedures including association of the enzyme to fatty acid-linked Sepharose and affinity labeling with fluorescent fatty acid. Furthermore, circular dichroism analysis showed that the binding of hydrophobic ligand to GST-P produced a remarkable conformational change of the enzyme, which led to states devoid of transferase activity. In addition, the hydrophobic ligand binding caused a significant fluorescence quenching of tryptophan 38, which was assumed to be located at the active center of GST-P. It could be the result of a conformational change of the active center of the enzyme.

Affinity Labels↗
PubMed1990

Effect of triiodothyronine on triglyceride synthesis in human fibroblasts in different types of hypertriglyceridemia.

Fibroblasts from 12 normotriglyceridemic subjects and 30 hypertriglyceridemic patients and family members were used to investigate triglyceride synthesis and the influence of triiodothyronine on it. The monolayers were incubated for 72 hours with and without the thyroid hormone, followed by incorporation studies of radiolabeled acetic acid or palmitic acid into the cellular triglyceride fraction. Triiodothyronine had no influence on triglyceride synthesis of normal cell lines and of cells derived from patients with secondary hypertriglyceridemia, whereas fibroblasts from endogenous type IV patients showed higher rates of triglyceride synthesis under identical conditions. Values for type IV were in the range of 134% to 466% of the hormone-free control incubations. In cultures derived from patients with familial combined hyperlipidemia, no stimulation by triiodothyronine was observed: values were in the range of 64% to 144% of the hormone-free controls. Three out of four lines with type V gave "normal" values and are supposed to represent secondary hypertriglyceridemia, whereas one line may express endogenous type IV. The evidence obtained in vitro with cultured cells indicates different metabolic defects in endogenous type IV and familial combined hyperlipidemia; it also shows the biochemically heterogenous nature of the disease "hypertriglyceridemia."

Acetates↗
PubMed2001

Atomic resolution structure analysis of beta' polymorph crystal of a triacylglycerol: 1,2-dipalmitoyl-3-myristoyl-sn-glycerol.

The crystal structure of the beta'-2 form of a mixed chain triacylglycerol (TAG), 1,2-dipalmitoyl-3-myristoyl-sn-glycerol (PPM), was determined to a final reliability factor of 0.074. This work is the first to resolve the atomic-level structure of the beta' polymorph, which is of the highest functionality among multiple polymorphs in asymmetric TAG. In particular, fat crystals present in food emulsions are in beta', whose transformation into beta causes deterioration in their physical properties. beta'-2, one of the two beta' forms of PPM, forms a monoclinic unit cell with a space group of C2; Z = 8, a = 16.534(5) A, b = 7.537(2) A, c = 81.626(9) A; beta = 90.28(2) degrees, V = 10171(3) A(3), density = 1.018 g/cm(3), and mu = 4.96 cm(-1). The following characteristics were obtained: 1) two asymmetric units, named A and B, form a hybrid-type orthorhombic perpendicular subcell; 2) the two asymmetric units reveal different glycerol conformations: trans for sn-1 palmitic acid and sn-2 palmitic acid, but gauche for sn-3 myristic acid in A; and trans for sn-2 palmitic acid and sn-3 myristic acid, but gauche for sn-1 palmitic acid in B; 3) a unit lamellae reveals a four-chain-length structure consisting of two double-layer leaflets; 4) the two double-layer leaflets are combined end-by-end in a unit lamellae; and 5) the chain axes are alternatively inclined against the lamellar interface. -- Sato, K., M. Goto, J. Yano, K. Honda, D. R. Kodali, and D. M. Small. Atomic resolution structure analysis of beta' polymorph crystal of a triacylglycerol: 1,2-dipalmitoyl-3-myristoyl-sn-glycerol. J. Lipid Res. 2001. 42: 338--345.

Calorimetry, Differential Scanning↗
PubMed1995

[Chemical constituents of Cyclocarya paliurus (Batal.) Iljinsk].

Four compounds were isolated from the leaves of Cyclocarya paliurus. They were identified as daucosstero, beta-L-arabopyranose, steraric acid and palmitic acid on the basis of spectral data and chemical properties. All of them were isolated from this plant for the first time.

Drugs, Chinese Herbal↗
PubMed1998

Effects of chain length and unsaturation of fatty acid mixtures infused into the abomasum of lactating dairy cows.

Six cows were utilized in a 6 x 6 Latin square design with 21-d periods to determine effects of the postruminal profile of fatty acids on dry matter (DM) intake, milk yield and composition, nutrient digestibilities, and plasma metabolites. Treatments were abomasal infusions of 1) control [168 g/d of meat solubles (carrier for fatty acids) plus 10.6 g/d of Tween 80 (emulsifier)], 2) control plus 450 g/d of mostly saturated fatty acids, 3) control plus 450 g/d of palm oil fatty acids low in linoleic acid, 4) control plus 450 g/d of palm oil fatty acids, 5) control plus 450 g/d of soybean oil fatty acids, and 6) control plus 450 g/d of soybean oil fatty acids high in palmitic acid. Treatments 2, 3, 4, and 6 contained similar ratios of C16 to C18 fatty acids. Infusion of soybean oil fatty acids or soybean oil fatty acids high in palmitic acid decreased intakes of DM, organic matter, crude protein, acid detergent fiber, neutral detergent fiber, gross energy, and total fatty acids and tended to decrease yields of milk and fat-corrected milk compared with the infusion of mostly saturated fatty acids. Infusion of palm oil fatty acids low in linoleic acid or palm oil fatty acids decreased milk fat percentage compared with other treatments. Ruminal characteristics and apparent digestibilities of DM, organic matter, crude protein, acid detergent fiber, neutral detergent fiber, energy, total fatty acids, and total C18 fatty acids were not different. Infusion of fatty acids increased concentrations of cholesterol in plasma. The amount of unsaturated fatty acids passing into the small intestine may influence responses of dairy cows to supplemental fat.

Abomasum↗
PubMed1967

Changes in fatty acid composition of sulfolipid and phospholipids during maturation of alfalfa.

Lipids were extracted from alfalfa samples collected at intervals over the growing season and were fractionated to yield pure sulfolipid. In the sulfolipid and in a phospholipid fraction the major fatty acids were palmitic, linolenic, and linoleic, of which the palmitic acid increased in proportion during the season while the proportion of linolenic acid dropped. The sulfolipid contained more linolenic acid and less palmitic and linoleic acids than the phospholipids, and had a greater rate of change of fatty acid composition.

Chromatography↗
PubMed1990

Palmitic acid-labeled lipids selectively incorporated into platelet cytoskeleton during aggregation.

Previous experiments showed that during the early stages (20-30 seconds) of aggregation induced by adenosine diphosphate (ADP, 2 microM) or thrombin (0.1 U/mL) of rabbit or human platelets prelabeled with [3H]palmitic acid, labeled lipid became associated with the cytoskeleton isolated after lysis with 1% Triton X-100, 5 mM EGTA [ethylene glycol-bis-(beta-aminoethyl ether)]-N,N,N',N'-tetra-acetic acid. The association appeared to be related to the number of sites of contact and was independent of the release of granule contents. We have now investigated the nature of the labeled lipids by thin-layer and column chromatography and found differences between the distribution of the label in intact platelets (both stimulated and unstimulated) and the isolated cytoskeletons. In both species, and with either ADP or thrombin as aggregating agent, 70-85% of the label in both intact platelets and in the cytoskeletons was in phospholipids. The distribution of label among the phospholipids in the cytoskeletons was similar to that in intact platelets except that the percentage of label in phosphatidylcholine was significantly higher in the cytoskeletons of human platelets than in the intact platelets, and the percentage of label in phosphatidylserine/phosphatidylinositol was significantly lower in the cytoskeletons of rabbit platelets and thrombin-aggregated human platelets than in intact platelets. The cytoskeletons contained a lower percentage of label in triacylglycerol, diacylglycerol, and cholesterol ester than the intact platelets. Contrary to a report in the literature, we found no evidence for the incorporation of diacylglycerol and palmitic acid into the cytoskeleton.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1983

Constitutive uptake and degradation of fatty acids by Yersinia pestis.

Yersinia pestis was found to utilize palmitic acid as a primary carbon and energy source. No inhibition of growth by palmitic acid was observed. Comparison of palmitic acid uptake by cells pregrown either with or without palmitic acid demonstrated that fatty acid uptake was constitutive. High basal levels of two enzymes of beta-oxidation, beta-hydroxyacyl-coenzyme A dehydrogenase and thiolase, and the two enzymes of the glyoxylate shunt, isocitrate lyase and malate synthase, were found in cells grown in defined medium with glucose. Elevated levels of all four enzymes were found when cells were grown with acetate as a primary carbon and energy source, and even higher levels were observed when palmitic acid was provided as a primary carbon and energy source. High-pressure liquid chromatography was used to demonstrate that, in the presence of glucose, uniformly labeled [14C]palmitic acid was converted to intermediates of the tricarboxylic acid cycle and glyoxylate shunt. Pregrowth with palmitic acid was not required for this conversion. Strains lacking the 6- or the 47-megadalton plasmid did not take up [3H]palmitic acid but did possess levels of enzyme activity comparable to those observed in the wild-type strain.

3-Hydroxyacyl CoA Dehydrogenases↗
PubMed1994

Absorption of isomeric, palmitic acid-containing triacylglycerols resembling human milk fat in the adult rat.

The effect of the positional distribution of palmitic acid (16:0) in triacylglycerols (TAG) on 16:0 apparent absorption in adult rats was investigated. The rats were fed two diets which contained 30 energy % as fat with identical total fatty acid compositions, both containing 30% 16:0. The Betapol diet contained TAG with 73% of total 16:0 in the sn-2 position, the control diet contained TAG with 6% of total 16:0 in the sn-2 position. After six weeks on these diets, the rats were killed two or six hours after the last meal, and the small intestine was removed, cut into 10-cm segments, and the fatty acid composition of the segment's contents was determined. At both time points the amount of 16:0 in the intestinal segments starting at 40 cm from the stomach was much lower in the animals fed Betapol than in the animals fed the control diet. Overall absorption of 16:0 and stearic acid was significantly greater in the Betapol group. Absorption of oleic and linoleic acid from the small intestine was similar in both groups, although the overall absorption was significantly greater in the animals fed Betapol. Total fat absorption was significantly higher in the Betapol-fed rats than in the control-fed rats. No effect on calcium and nitrogen absorption, on plasma total cholesterol and TAG levels, and on bodyweights (growth) was seen. The data demonstrate that the positional distribution of the fatty acids in the TAG molecule affects the site of absorption in the small intestine and particularly the net absorption of saturated fatty acids.

Animal Feed↗
PubMed1999

Intermediates and products formed during fatty acid alpha-oxidation in cucumber (Cucumis sativus).

Fatty acid alpha-oxidation is an essential metabolic pathway both in plants and in mammals which is still not completely understood. We previously described and purified an alpha-oxidation enzyme in cucumber which has been used in the present investigation of the alpha-oxidation reaction mechanism. Free fatty acids, and not the CoA thioesters, were found to undergo alpha-oxidation in cucumber. 2-Hydroxy- and 2-oxopalmitic acids were identified as palmitic acid alpha-oxidation intermediates by high-performance liquid chromatography and gas chromatography-mass spectrometry analysis in cucumber subcellular 150,000 x g(max) pellets obtained by differential centrifugation. Incubation of purified alpha-oxidation enzyme with [1-14C]palmitic acid resulted in the formation of both the above-described intermediates and the Cn-1 product, pentadecanal, and 14CO2. Besides 14CO2, 14C-formate was identified as an alpha-oxidation product from [1-14C]palmitic acid in cucumber subcellular fractions. Fe2+ stimulated the 14CO2 and 14C-formate production, and the addition of ascorbate and 2-oxoglutarate together with Fe2+ resulted in optimal alpha-oxidation activities, suggesting a dioxygenase reaction mechanism, as previously shown in mammals. NADPH and, to a lesser extent, NADH stimulated the total 14C-formate plus 14CO2 production but had only slight or no effects on 14CO2 production. H2O2 showed concentration-dependent inhibitory effects, while FAD had neither effect on 14CO2 nor 14CO2 plus 14C-formate production. The results in the present study demonstrate that an alpha-oxidation enzyme in cucumber is capable of oxidizing palmitic acid via 2-hydroxy- and 2-oxo-palmitic acid to produce pentadecanal and CO2. In contrast to the subcellular 150,000 x g(max) fraction, the purified alpha-oxidation enzyme could neither produce formate nor convert 14C-formate into 14C02, indicating two possible alpha-oxidation routes in cucumber.

Acyl Coenzyme A↗
PubMed1994

Dietary saturated and trans fatty acids and lipoprotein metabolism.

Earlier studies have shown that not all saturated fatty acids are equally hypercholesterolaemic: stearic acid (C18:0) and saturated fatty acids with less than 12 carbon atoms are thought not to raise serum cholesterol levels. This suggests that the cholesterol-raising effects of saturated fatty acids can be attributed to lauric acid (C12:0), myristic acid (C14:0) and palmitic acid (C16:0). These three saturated fatty acids also have different effects on serum total cholesterol levels. Results from recent controlled dietary experiments suggest that lauric acid raises serum total and low-density lipoprotein (LDL) cholesterol levels slightly less, and myristic acid more, as compared with palmitic acid. Myristic acid, however, also causes higher levels of high-density lipoprotein (HDL) cholesterol. Stearic acid has only a slight effect on serum LDL and HDL cholesterol levels as compared with oleic acid. Trans monounsaturated fatty acids, however, increase LDL and decrease HDL cholesterol levels. Precise effects on lipoproteins of short and medium chain triglycerides (C4:0-C10:0) have never been examined.

Cholesterol, HDL↗
PubMed1993

Corandomization of fats improves absorption in rats.

Human milk fat is well absorbed despite its large concentration of long-chain saturated fatty acids (LCSFA), particularly palmitic acid. The superior absorption has been ascribed in part to the uncommonly high proportion of the palmitic acid in the sn-2 position of the triglycerides, 70% in human milk triglycerides compared with 10-15% in the fats and oils commonly used in infant formula blends. Colipase-dependent pancreatic lipase selectively hydrolyzes the fatty acids at the sn-1 and 3 positions, yielding free fatty acids and the 2-monoglyceride, which are absorbable. Free palmitic acid, but not monopalmitin, can be lost as calcium soaps in the feces. The present study demonstrated that mixtures of coconut oil and palm olein are better absorbed by rats if the proportion of LCSFA in the sn-2 position is increased by the process of chemical randomization, in which the fatty acids of the native oils are redistributed equally to all three positions in the rearranged triglycerides. The fecal excretion of total fatty acids, essentially LCSFA, from the mixtures in which the oils were randomized together (corandomized) was 30 to 60% less than from the mixtures of native oils.

Animals↗
PubMed1996

Modulation of the activity of the human cholesteryl ester transfer protein by carboxylated derivatives. Evidence for 13-cis-retinoic acid as a potent activator of the protein's activity in plasma.

The influence of palmitic acid, 13-cis-retinoic acid, all-trans-retinoic acid, and all-trans-retinol on the activity of the human cholesteryl ester transfer protein (CETP) was evaluated either in total human plasma supplemented with a tracer dose of 3H-labeled cholesteryl-ester-containing high-density lipoprotein sub-fraction 3 ([3H]CE-HDL3), or in reconstituted mixtures containing [3H]CE-HDL3, isolated low-density lipoproteins (LDL), and purified CETP. In reconstituted mixtures, all the carboxylated derivatives increased progressively and significantly the transfer of 3H-labeled cholesteryl esters from [3H]CE-HDL3 towards LDL in the 20-100 microM concentration range. Under identical experimental conditions, CETP activity was only minimally modified in the presence of all-trans-retinol. When present at a concentration of 60, 80, or 100 microM, 13-cis-retinoic acid was a significantly more potent activator of CETP activity than all the other derivatives studied (P < 0.01 in all cases). In contrast to observations made with reconstituted mixtures, only 13-cis-retinoic acid, but not palmitic acid, was able to induce a significant, concentration-dependent stimulation of CETP activity in total human plasma. In fact, differences in the ability of 13-cis-retinoic acid and palmitic acid to modulate the plasma cholesteryl ester transfer reaction were linked to their relative affinity for albumin and lipoprotein substrates: fatty-acid-poor albumin reduced CETP activity to a significantly greater extent in reconstituted mixtures containing palmitic acid than in reconstituted mixtures containing 13-cis-retinoic acid (P < 0.01 for all the incubation mixtures in the 1-10 g/l albumin concentration range); palmitic acid presented a markedly lower ability to increase the electrophoretic mobility of LDL and HDL fractions in total plasma than 13-cis-retinoic acid. In support of a key role of the negatively charged carboxylic group of 13-cis-retinoic acid in upregulating CETP activity, cholesteryl ester transfer rates correlated positively with the electrophoretic mobility of LDL (r = 0.98; P < 0.0002) and HDL (r = 0.96; P < 0.0008) in total plasma supplemented with the carboxylated compound. It is concluded that 13-cis-retinoic acid can upregulate the CETP-mediated cholesteryl ester transfer reaction both in reconstituted mixtures containing isolated lipoproteins and purified CETP, and in total normolipidemic human plasma.

Blood Protein Electrophoresis↗
PubMed2004

Chronic hyperglycaemia promotes lipogenesis and triacylglycerol accumulation in human skeletal muscle cells.

AIMS/HYPOTHESIS: The present study was conducted to evaluate the effect of hyperglycaemia in itself on glucose and lipid metabolism in human skeletal muscle cells. METHODS: Satellite cells were isolated from biopsy samples from the vastus lateralis muscle and differentiated into multinucleated myotubes in cultures. Metabolism studies were performed using isotopes ([3H]deoxyglucose, [14C]glucose, [14C]oleic acid and [14C]palmitic acid), and mRNA and protein levels were analysed by real-time RT-PCR and western blotting respectively. RESULTS: Exposure of myotubes to 20 mmol/l glucose for 4 days reduced insulin-stimulated glucose uptake and glycogen synthesis to 57+/-5% (p<0.0001) and 56+/-5% (p<0.0001) of normoglycaemic (5.5 mmol/l glucose) controls respectively. Basal glucose uptake and glycogen synthesis were both reduced, whereas glucose oxidation was unaltered. Total cell content of glycogen and expression of GLUT1 and GLUT4 mRNA were not affected. There was a significant increase in the incorporation of glucose into cellular NEFA (88+/-17% increase, p=0.006), triacylglycerol (44+/-21% increase, p=0.04) and cholesterol ester (89+/-36% increase, p=0.02) in hyperglycaemic myotubes compared with controls. Diacylglycerol tended to be increased though not significantly, and phospholipid formation were unchanged. Relative to controls, total cell content of triacylglycerol was increased by 25+/-7% (p=0.02) and acyl-CoA:1,2-diacylglycerol acyltransferase 1 activity was increased by 34+/-4% (p=0.004), whereas acyl-CoA:1,2-diacylglycerol acyltransferase 1 mRNA expression was unchanged. Total cellular uptake of palmitic acid was reduced by 18+/-3% (p=0.006) in hyperglycaemic cells compared with controls, while uptake of oleic acid was unchanged. Oxidation of palmitic acid or oleic acid was not affected by hyperglycaemia. CONCLUSIONS/INTERPRETATION: Chronic hyperglycaemia increased triacylglycerol accumulation and the incorporation of carbohydrate into triacylglycerol (i.e. de novo lipogenesis) concomitantly with a reduced insulin-stimulated glucose uptake and glycogen synthesis. Enhanced acyl-CoA:1,2-diacylglycerol acyltransferase 1 activity supported the increased triacylglycerol synthesis during hyperglycaemia.

Base Sequence↗