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PubMed1981

Characterization of a novel glycosphingolipid, ceramide nonasaccharide, isolated from spermatozoa of the fresh water bivalve, Hyriopsis schlegelii.

A new glycosphingolipid, provisionally named Lipid III in our previous work (Hori, T., Sugita, M., Kanbayashi, J., and Itasaka, O. (1977) J. Biochem. (Tokyo) 81, 107-114), was extracted and purified from the spermatozoa of the fresh water bivalve, Hyriopsis schlegelii. The yield of the glycolipid was 1.8 mg/g dry weight of the spermatozoan preparation. Its chemical structure was characterized by compositional analysis, partial acid hydrolysis, methylation analysis, and proton nuclear magnetic resonance spectroscopy. The following structure is proposed: 3-O-MeFuc alpha 1 leads to 2.3-O-MeXyl beta 1 leads to 4(3-O-MeGalNAc alpha 1 leads to 3)Fuc alpha 1 leads to 4GlcNAc beta 1 leads to 2Man alpha 1 leads to 3(Xyl beta 1 leads to 2)Man beta 1 leads to 4Glc beta 1 leads to 1Cer. This glycolipid contains the same backbone as the pentaglycosyl ceramide (Lipid II) reported previously (Hori, T., Takeda, H., Sugita, M., and Itasaka, O. (1977) J. Biochem. (Tokyo) 82, 1281-1285). Lipid III is structurally related to Lipid II by linking it with a fucose and three kinds of O-methyl sugars, namely, 3-O-methylxylose, 3-O-methylfucose, and 3-O-methyl-N-acetylgalactosamine, through an internal fucose moiety. Unlike most vertebrate glycolipids, Lipid III appears to be unique in having an internal fucose and O-methyl sugars as well as mannose. To our knowledge, this is the first instance for the natural occurrence of 3-O-mehylxylose. Aliphatic constituents of the lipid are palmitic acid and stearic acid as the principal fatty acids, and octadeca-4-sphingenine as the major long chain base.

Animals↗
PubMed1994

Unsaturated fatty acids are required for continuous proliferation of transformed androgen-dependent cells by fibroblast growth factor family proteins.

Increase in dietary fat intake has been reported to be associated with progression of hormone-dependent cancers. To explore its mechanism, we examined the effects of fatty acids on the growth of androgen-dependent SC-3 cells cloned from mouse mammary cancer (Shionogi carcinoma 115). Their androgen-dependent growth was potentiated by linoleic acid in the defined medium. The effect of linoleic acid on fibroblast growth factor (FGF)-dependent growth was also addressed because androgen had been demonstrated to exert its mitogenic activity on SC-3 cells through an induction of the unique FGF family protein termed as androgen-induced growth factor. Exposure of SC-3 cells to basic FGF or androgen-induced growth factor exhibited only transient growth response. However, simultaneous addition of linoleic acid to the medium sustained the proliferation of FGF-stimulated, but not FGF-unstimulated, cells, although linoleic acid did not exert the significant effect on the process of S-phase entry of basic FGF-stimulated cells. Palmitoleic acid and oleic acid appeared to exert the actions similar to linoleic acid, while stearic acid was without any effect. Neither cyclooxygenase inhibitor nor 5-lipoxygenase inhibitor could block the growth-promoting ability of linoleic acid. Linoleic acid also enhanced their anchorage-independent growth in the presence of basic FGF. These results indicate that these unsaturated fatty acids play a role in sustaining the proliferation of FGF-stimulated SC-3 cells.

Animals↗
PubMed1994

Rat very-long-chain acyl-CoA dehydrogenase, a novel mitochondrial acyl-CoA dehydrogenase gene product, is a rate-limiting enzyme in long-chain fatty acid beta-oxidation system. cDNA and deduced amino acid sequence and distinct specificities of the cDNA-expressed protein.

cDNA encoding the precursor of rat very-long-chain acyl-CoA dehydrogenase (VLCAD) was cloned and sequenced. The longest cDNA insert had 2117 bases. This cDNA encodes the entire protein of 655 amino acids, including a 40-amino acid leader peptide and a 615-amino acid mature polypeptide. The identity of the VLCAD clone was confirmed by matching the amino acid sequence predicted from the cDNA to the NH2 terminus and seven internal proteolytic peptide sequences from purified rat liver VLCAD. The calculated molecular masses of the precursor protein, the mature protein, and the leader peptide are 70,961, 66,508, and 4,470 daltons, respectively. At the amino acid level, the significant homology to the other acyl-CoA dehydrogenases was found at the range from the 94th to the 473rd amino acid residue of the amino-terminal side. The catalytic residue and the residue lying near the dimethylbenzene side (si-side) of the flavin ring were speculated to be Glu-462 and Trp-249, respectively. The VLCAD cDNA was expressed in four kinds of hepatoma cells using a vaccinia virus expression system and was shown to encode the catalytically active enzyme. The cDNA expression in both rat hepatoma H4IIEC3 and McA-RH7777 enhanced about 3-fold mitochondrial beta-oxidation activity of long-chain fatty acids such as palmitic acid and stearic acid; hence, VLCAD is probably a rate-limiting enzyme in the long-chain fatty acid beta-oxidation system in these cell lines.

Acyl-CoA Dehydrogenase, Long-Chain↗
PubMed1993

The activation of factor VII in citrated plasma by charged long-chain saturated fatty acids at the interface of large triglyceride-rich lipoproteins.

The prolonged incubation of dilute plasma on ice in the presence of added sulphatide vesicles or the long-chain saturated fatty acids (FA) stearic acid (C18:0) or behenic acid (C22:0) induced a concentration-dependent increase in factor VII coagulant activity (VIIc). The addition of FA at various ratios to human serum albumin showed the micellar non-bound pool to be responsible for this effect, FA bound to the high-affinity or low-affinity binding sites of albumin having no influence on VIIc. Plasma VIIc also increased following addition of behenate-enriched lipoprotein particles produced by incubation of the d < 1.006 g/ml lipoprotein fraction with this FA, or addition of lipoprotein remnants produced by pre-incubation of the d < 1.006 g/ml fraction with lipoprotein lipase. Long-chain saturated fatty acids in the interface of lipoprotein remnants, produced by the interaction of triglyceride-rich lipoprotein particles with lipoprotein lipase, appear to provide a surface that activates the contact system of coagulation and subsequently factor VII.

Anticoagulants↗
PubMed1993

[Identification and characterization of hydrophobic ligand binding region in glutathione S-transferase P].

Recombinant glutathione S-transferase P (GST-P) was purified in a homogeneous state. Fatty acid analysis by gas-liquid chromatography-mass spectrometry (GC-MS) revealed that GST-P forms 1:1 complex with fatty acids, mostly palmitic acid or stearic acid, which were hardly isolated from the complex even through Lipidex 1,000 column chromatography at 37 degrees C. Temperature dependent analysis of 1H-NMR on the association between GST-P and fatty acids indicated that molecular motion of fatty acids were strongly restrained in a hydrophobic 'pocket' below the temperature of protein denaturation. On the other hand, there existed another hydrophobic ligand binding region, to which fatty acid and bilirubin would bind with relatively lower affinity. The binding region was determined to be at around 142-157 residues from amino terminus by the studies of GST-P binding to fatty acid-linked Sepharose and affinity labelings with either fluorescent fatty acid or bilirubin. The binding to this region noncompetitively inhibited the enzyme activity. Furthermore, circular dichroism (CD) analysis showed that the binding of hydrophobic ligands changed the secondary structure of GST-P, which suggested that the enzyme activity was regulated through conformational changes. As tryptophan 38 was assumed to locate at the active center from the study of site-directed mutagenesis, conformation of the active center was investigated by measuring the intrinsic tryptophan fluorescence. It showed that hydrophobic ligand binding caused the drastic conformational change, of which would be referred to the regulation of the enzyme activity.

Binding Sites↗
PubMed1993

The adipocyte lipid-binding protein at 1.6-A resolution. Crystal structures of the apoprotein and with bound saturated and unsaturated fatty acids.

Crystals of the adipocyte lipid-binding protein which diffract to near atomic resolution have been obtained in Na/K phosphate buffer/precipitant system. The structures of the apo-form and the protein with bound oleic acid and stearic acid have been determined and refined to 1.6-A resolution with R-factor around 18%. The conformations of the bound fatty acids are nearly the same. In both cases, the carboxylate group of the ligand interacts directly with Arg126 and Tyr128, indirectly with Arg106 through a water molecule. The hydrocarbon tail sticks out of the protein surface through a hydrophobic patch. Saturated and unsaturated fatty acids bind in essentially the same conformation. The remaining space of the binding pocket is filled with well ordered water molecules interacting with most of the polar side chains. Comparisons between the holo- and apostructures reveal that the hydrophobic patch on the protein surface formed by a helix and several tight turns might serve as a portal for lipid binding. Since the adipocyte lipid-binding protein is phosphorylated at Tyr19 by the insulin receptor kinase, the position of this side chain has been re-evaluated using the coordinates of the holo-forms. It appears that the position of Tyr19 does not change significantly upon the binding of either of the fatty acids.

Amino Acid Sequence↗
PubMed1995

[Free fatty acids in gallbladder bile].

Using gas chromatography and high performance liquid chromatography (HILC), we examined free fatty acid and lecithin molecular species in gallbladder biles from patients with cholesterol gallstones. Effect of free fatty acids on cholesterol nucleation in model bile was studied by a sensitive cholesterol crystal growth assay. Compared to bile of controls, biles from patients with gallstones had higher total free fatty acid level, more palmitic acid, more stearic acid, more linoleic acid and arachidonic acid. The lecithin pattern was similar in all. After free fatty acids were added to model bile, palmitic acid, oleic, acid, linoleic acid and arachidonic acid had significant effect of pro-nucleating, free fatty acids on non-protein pro-nucleating factor. These data suggest that variations in quantitation and composition of free fatty acids are importanct in the pathogenesis of cholesterol gallstone formation.

Bile↗
PubMed1977

[Effects of various modes of therapy on the fatty acid spectrum in hyperlipoproteinemia].

Gas-chromatographic investigations of the fatty acid pattern of the fractions of serum triglyceride and serum cholesterol ester revealed characteristic changes under different therapeutic measures in altogether 120 patients with primary hyperlipoproteinaemia of the types IIa, IIb and IV. Already under the treatment with basal metabolic diet, more clearly by medication with clofibrin acid, in the hyperlipoproteinaemia type IV the decrease of the palmitic acid, the palmitoleic acid, the stearic acid and oleic acid and the increase of linoleic acid, linoleneic acid, arachidonic acid and eikopentaenic acid in the triglyceride fraction developed. These fatty acids showed the same behaviour under the therapy with derivatives of nicotinic acids in the cholesterol ester fraction in the hyperlipoproteinaemia of type IIa. The combined treatment of the type IIb resulted in the same tendencies, however not so pronounced, of the spectrum in the cholesterol esters as well as of the fatty acids esterified in the triglycerides.

Cholesterol↗
PubMed1997

The relation between serum fatty acids and soil-transmitted helminthiasis in the Philippines.

The purpose of this study was observe the effects of soil-transmitted helminthiasis on the amounts of fatty acids in the serum. The subjects were 32 females with age ranging from 15 to 55 years old (22.6 +/- 12.0). The intensity of infection was light based on the criteria of the WHO Expert Committee. Seven fatty acids and serum cholesterol were determined, with the pentadecanoic acid (C15: 0) as internal standard. Serum fatty acid levels were correlated with age-group, dietary habit and body mass index. These factors were however not related with the levels of the serum fatty acids. But the amounts of palmitic acid and stearic acid in the infected group were markedly reduced as compared with the non-infected group.

Adolescent↗
PubMed1976

[Metabolism of essential and endogenous serum fatty acids in healthy persons, coronary disease and patients with lipid metabolism disorder. Partial aspect of high risk problem patients with age-related lipid and fatty acid concentrations in serum and regulation of long-chain products from essential and endogenous precursors in healthy subjects].

Total lipid, free and esterified cholesterol and triglycerides significantly increase in concentration with increasing age. Palmitic, palmitoleic, oleic and linoleic acid behave in the same way. Free fatty acids, phospholipids and stearic acid show the same concentrations in all groups of age. C20 fatty acids demonstrate a competitive regulatory mechanism of desaturase activity in their age dependant distribution. While the 20:3(n-9), a product of the endogenous (n-9) family, increases, the 20:3(n-6) and 20:4(n-6), both desaturation and chain elongation products of the essential n-6 family, decrease. Such behavior has been demonstrated in many feeding studies (12, 13, 15, 16, 17, 29) and is interpreted as a result of competitive substrate interaction on desaturase activity.

8,11,14-Eicosatrienoic Acid↗
PubMed2002

Block copolymer micelles for the encapsulation and delivery of amphotericin B.

PURPOSE: To assess the effect of fatty acid substitution of a micelle-forming poly(ethylene oxide)-block-poly(N-hexyl stearate-L-aspartamide) (PEO-b-PHSA) on the encapsulation, hemolytic properties and antifungal activity of amphotericin B (AmB). METHODS: PEO-b-PHSA with three levels of stearic acid substitution were synthesized and used to encapsulate AmB by a solvent evaporation method. Size exclusion chromatography and UV spectroscopy were used to confirm and measure levels of encapsulated AmB. The hemolytic activity of encapsulated AmB toward human red blood cells and its minimum inhibitory concentration against Candida albicans, Aspergillus fumigatus and Cryptococcus neoformans were obtained and compared to AmB alone. RESULTS: An increase in the level of stearic acid substitution on PEO-b-PHSA improved the encapsulation of AmB while reducing its hemolytic activity. PEO-b-PHSA micelles having 50% and 70% stearic acid substitution (mol fatty acid: mol reacted and unreacted hydroxyls) were completely non-hemolytic at 22 microg/ml. At 11% stearic acid substitution, AmB caused 50% hemolysis at 1 microg/ml. AmB in PEO-b-PHSA micelles was as effective as AmB alone against pathogenic fungi. CONCLUSIONS: PEO-b-PHSA micelles with a high level of stearic acid side chain substitution can effectively solubilize AmB, reduce its hemolytic activity yet retain its potent antifungal effects.

Amphotericin B↗
PubMed2006

Chocolate and prevention of cardiovascular disease: a systematic review.

BACKGROUND: Consumption of chocolate has been often hypothesized to reduce the risk of cardiovascular disease (CVD) due to chocolate's high levels of stearic acid and antioxidant flavonoids. However, debate still lingers regarding the true long term beneficial cardiovascular effects of chocolate overall. METHODS: We reviewed English-language MEDLINE publications from 1966 through January 2005 for experimental, observational, and clinical studies of relations between cocoa, cacao, chocolate, stearic acid, flavonoids (including flavonols, flavanols, catechins, epicatechins, and procynadins) and the risk of cardiovascular disease (coronary heart disease (CHD), stroke). A total of 136 publications were selected based on relevance, and quality of design and methods. An updated meta-analysis of flavonoid intake and CHD mortality was also conducted. RESULTS: The body of short-term randomized feeding trials suggests cocoa and chocolate may exert beneficial effects on cardiovascular risk via effects on lowering blood pressure, anti-inflammation, anti-platelet function, higher HDL, decreased LDL oxidation. Additionally, a large body of trials of stearic acid suggests it is indeed cholesterol-neutral. However, epidemiologic studies of serum and dietary stearic acid are inconclusive due to many methodologic limitations. Meanwhile, the large body of prospective studies of flavonoids suggests the flavonoid content of chocolate may reduce risk of cardiovascular mortality. Our updated meta-analysis indicates that intake of flavonoids may lower risk of CHD mortality, RR = 0.81 (95% CI: 0.71-0.92) comparing highest and lowest tertiles. CONCLUSION: Multiple lines of evidence from laboratory experiments and randomized trials suggest stearic acid may be neutral, while flavonoids are likely protective against CHD mortality. The highest priority now is to conduct larger randomized trials to definitively investigate the impact of chocolate consumption on long-term cardiovascular outcomes.

Journal Article↗
PubMed2002

Activity-guided fractionation of the seeds of Ziziphus jujuba using a cyclooxygenase-2 inhibitory assay.

Bioactivity-guided fractionation of petroleum ether- and EtOAc-soluble extracts of the seeds of Ziziphus jujuba using a cyclooxygenase-2 assay as a monitor indicated that the triglyceride, 1,3-di-O-[9(Z)-octadecenoyl]-2-O-[9(Z),12(Z)-octadecadienoyl]glycerol (3), and a fatty acid mixture of linoleic, oleic and stearic acids, were the major active components. A new pentacyclic lupane-type triterpene derivative, 3-O-[9(Z)-octadecenoyl]betulinic acid (1), and betulinic acid (2) were also isolated and identified. All isolates as well as pure linoleic, oleic and stearic acids were evaluated for their inhibitory effects against both cyclooxygenases-1 (COX-1) and -2 (COX-2).

Cyclooxygenase 1↗
PubMed1965

FURTHER STUDIES ON THE LIPID METABOLISM OF THE NORMAL AND VITAMIN B-12 DEFICIENT CHICK EMBRYO.

1. The triglyceride, cholesterol ester and total phospholipid fractions were isolated from the livers and yolk sacs of normal and vitamin B(12)-deficient chick embryos after 13, 15, 17, 19 and 21 days of incubation, and the fatty acid compositions were determined. 2. At all stages of incubation, the concentration of cholesterol ester in the livers of the normal embryos were greater, and on days 15 and 17 the concentrations of triglyceride were considerably less, than the corresponding concentrations in the livers of the deficient embryos. 3. Between day 13 and day 21 of incubation the concentration of oleic acid in the liver triglycerides of the normal embryos increased, whereas the concentrations of palmitic acid and docosahexaenoic acid decreased. Vitamin B(12) deficiency resulted in higher concentrations of palmitic acid in the liver triglycerides on days 15, 17 and 19, higher concentrations of C(18) polyunsaturated acids on days 13 and 15 and lower concentrations of oleic acid on days 13, 15, 17 and 19. 4. At all stages of development, cholesterol oleate accounted for almost 80% of the total liver cholesterol esters in both normal and deficient embryos. 5. As development of the normal embryos progressed, the concentrations of palmitic acid and arachidonic acid in the liver phospholipid decreased, whereas the concentrations of stearic acid and docosahexaenoic acid increased. Vitamin B(12) deficiency resulted in markedly higher concentrations of stearic acid and palmitic acid and markedly lower concentrations of arachidonic acid and docosahexaenoic acid in the liver phospholipids. 6. Vitamin B(12) deficiency did not influence the fatty acid composition of the triglyceride, cholesterol ester and phospholipid fractions either in the yolks of fertile unincubated eggs or in the yolks obtained from eggs that had been incubated for 13, 15, 17, 19 and 21 days.

Animals↗
PubMed1984

Inhibition of chymase activity by long chain fatty acids.

The activity of chymase was markedly inhibited by fatty acids with carbon chain lengths of 14-22 at doses greater than 0.02 microM, irrespective of the number of double bonds. Cis acids with a carbon chain length of 18, such as stearic acid, oleic acid, linoleic acid, and linolenic acid were potent inhibitors, whereas the trans isomer of oleic acid, elaidic acid, showed less inhibitory activity. The extent of inhibition by oleyl alcohol was almost the same as that by oleic acid, suggesting that the acid moiety itself was not necessary for the inhibition; but a fatty acid with a terminal functional amide, oleamide, showed little inhibitory activity. The inhibition was noncompetitive and was reversible, and the Ki value of oleic acid was 2.7 microM. Stearic acid and oleic acid inhibited all chymotrypsin-type serine endopeptidases tested. The ID50 values of these fatty acids for atypical mast cell protease were higher than those for the other chymotrypsin-type serine endopeptidases tested. Other proteases, such as papain, trypsin, collagenase, and carboxypeptidase A, except cathespin D, were not affected by stearic or oleic acid.

Animals↗
PubMed1975

Effect of tweens on the production of ergot alkaloids by Aspergillus fumigatus.

Tween 80, which caused increased biomass formation, also produced the highest increase in the uptake rate of all components of the medium. The fatty acid components of the respective Tweens, i.e. palmitic acid (Tween 40), stearic acid (Tween 60), and oleic acid (Tween 80), have no effect either on alkaloid production or on substrate uptake. The fatty acid composition was different in the cell membrane of the culture supplemented with Tween 60 and facilitated the transport of metabolites into the cells.

Amino Acids↗
PubMed2002

Analytical characterization of Salicornia bigelovii seed oil cultivated in Pakistan.

Seeds of Salicornia bigelovii (hybrid variety sos-10) were collected from five coastal areas of Pakistan on the Arabian Sea. Hexane-extracted oil content was 27.2-32.0%. Results of other physical and chemical parameters of the extracted oil were as follows: iodine value, 128.0-130.5; refractive index (40 degrees C), 1.4680-1.4695; unsaponifiable matter, 1.63-2.00%; saponification value, 178.6-189.0; density (30 degrees C), 0.9036-0.9074. Tocopherols (alpha, gamma, and delta) in the oil ranged up to 200 mg/kg. The S. bigelovii seed oil was found to contain high levels of linoleic acid (74.66-79.49%) and less oleic acid (12.33-16.83%). Saturated fatty acids, palmitic and stearic acids, ranged from 7 to 8.50% and from 1.24 to 1.69%, respectively. Linolenic acid (C(18:3) omega-3) was found within the range of 1.50-2.31%. The induction period (Rancimat, 20 L/h, 120 degrees C) of the crude oil was 1.40-1.70 h. Specific extinctions at 232 and 270 nm were 1.90-2.40 and 0.40-0.62, respectively. Many parameters of S. bigelovii seed oil were quite compatible with those of safflower oil.

Chenopodiaceae↗
PubMed2003

Oxidation reaction of high molecular weight carboxylic acids in supercritical water.

Stearic acid, being a model compound of high molecular weight carboxylic acids, was oxidized in a batch reactor by changing the oxygen supply with an insufficient oxygen supply at a constant reaction time at 420 degrees C. On the basis of the intermediate products identified by GC/MS, NMR, and HPLC analyses and the free-radical reaction mechanism, the oxidation pathways of high molecular weight carboxylic acids in supercritical water are discussed. The reaction of carboxylic acids in supercritical water proceeds with the consecutive oxidation of higher molecular weight carboxylic acids to lower molecular weight carboxylic acids through several major pathways. The attack of the hydroxyl radical occurs not only at the carbons in alpha-, beta-, gamma-positions to a --COOH group but also at the carbons ((omega-1)-carbon and/or omega-carbon) far in the alkyl chain from a --COOH group, which may lead to the formation of dicarboxylic acids.

Chromatography, High Pressure Liquid↗