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PubMed2003

Influence of Fatty acids on foaming properties of cider.

Seventy-seven ciders from four consecutive harvests, which were produced at industrial scale by cider-makers from the region of Asturias (northern Spain), were analyzed to evaluate their foam capacity. The Bikerman method for the evaluation of foaming characteristics was adapted to ciders. In foaming, there are two parameters, foam formation and foam stability, which are found to be related to each other. To determine the relationship between fatty acid content and foaming properties of cider, the multivariate analysis technique of canonical correlation analysis was applied. Foam stability is positively related to the content of caprylic acid. Foam height is positively related to linolenic, pentadecanoic, and palmitic acid and negatively related to stearic and linoleic acid.

Beverages↗

PubMed2006

Comparative evaluation of the emulsifying properties of phosphatidylcholine after enzymatic acyl modification.

The ability of enzymatically synthesized structured phosphatidylcholine (PC) containing caprylic acid to form and stabilize oil-in-water emulsions prepared with different triglycerides [medium chain triglycerides (MCT), soybean oil, and enzymatically synthesized structured lipids] was examined and compared with natural soybean PC and deoiled lecithin. Emulsions were prepared with varying oil and emulsifier concentrations. The particle size distribution, creaming stability, and viscosity were measured for the evaluation of the emulsifying properties. With an increase in the oil concentration, there was an increase in particle size, viscosity, and creaming layer. With an increase in the phospholipid (PL) concentration, there was usually a decrease in particle size and an increase in viscosity, where the emulsion stability was increased. General emulsions prepared with structured lipids resulted in smaller particle sizes as compared to MCT and soybean oil. Deoiled lecithin was able to increase the viscosity more significantly and give smaller particle sizes as compared to the other emulsifiers, thus producing more stable emulsions. However, in certain cases, structured PC was superior to deoiled lecithin and soybean PC. This observation was made for emulsions prepared with soybean oil or structured lipid at an oil/water ratio of 10:90. At an oil/water ratio of 30:70, the deoiled lecithin performed better as compared to the other PLs with all oil types. However, structured PC produced more stable emulsions as compared to natural soybean PC in MCT and soybean oil.

Caprylates↗

PubMed2001

Oral delivery of biologically active parathyroid hormone.

PURPOSE: Parathyroid hormone (PTH), the only drug known to stimulate bone formation. is a peptide therapeutic indicated in the treatment of osteoporosis. Unfortunately, PTH is only effective when dosed by injection because it has no oral bioavailability. Herein we report the oral absorption of PTH in rats and monkeys facilitated by the novel delivery agent, N-[8-(2-hydroxy-4-methoxy)bensoyl]amino caprylic acid (4-MOAC). METHODS: 4-MOAC was selected from a group of 100 delivery agents based on in vitro chromotography studies and in vivo screening studies in rats. The PTH/4-MOAC combination was then tested in monkeys. The interaction of 4-MOAC and PTH was evaluated by nuclear magnetic resonance (NMR) spectroscopy. RESULTS: Monkeys were administered an aqueous solution containing 4-MOAC and PTH and mean peak serum PTH concentrations of about 3000 pg/mL were obtained. The relative bioavailability of oral PTH was 2.1% relative to subcutaneous administration. The biological activity of the orally-delivered PTH was further evaluated in a rat model of osteoporosis. These studies showed that the bone formed following oral PTH/4-MOAC administration was comparable to that formed following PTH injections. The 4-MOAC mediated absorption of PTH is hypothesized to be the result of a noncovalent interaction between 4-MOAC and PTH. The preliminary evaluation of this interaction by NMR is described. CONCLUSIONS: 4-MOAC facilitates the absorption of PTH following oral administration to both rats and monkeys. The orally-absorbed PTH is biologically active as demonstrated in a rat model of osteoporosis.

Administration, Oral↗

PubMed1996

Water-in-oil microemulsions containing medium-chain fatty acids/salts: formulation and intestinal absorption enhancement evaluation.

PURPOSE: Water-in-oil (w/o) microemulsions have been developed which, in addition to non-ionic medium-chain glycerides, incorporate ionic lipids, primarily medium-chain fatty acids, such as caprylic (C8) capric (C10) and lauric (C12) acids and their corresponding sodium salts. The absorption enhancing activity of w/o microemulsions incorporating these lipids was evaluated in the rat using Calcein (MW = 623) a water-soluble and poorly absorbed marker molecule. METHODS: Phase diagrams were constructed where C8/C10 or C12 fatty acids were treated as lipophilic surfactants and their sodium salts as hydrophilic ones. The anesthetised rat model was employed to evaluate Calcein absorption upon a single intraduodenal administration from a solution and the various w/o microemulsions. RESULTS: A wide range of clear and transparent w/o microemulsions were obtained at ambient temperature either in liquid or solid form when a fixed blend of medium chain fatty acid/salt was titrated by a fixed ratio of the oil containing the oil-soluble mono- and diglycerides and deionized water or physiological saline. Upon intraduodenal administration in the anesthetised rat, the absorption of Calcein was improved from about 2% in aqueous solution up to about 37% in w/o microemulsions. Solid and liquid formulations were equally effective in improving bioavailability. The absorption enhancement activity of the fatty acids/salts followed the order C8 approximately C10 > C12. Absorption enhancement of Calcein was significantly reduced in the absence or presence of low levels of C8/C10 mono-/diglycerides. CONCLUSIONS: These results further support the use of medium-chain glycerides and fatty acids/salts in microemulsion formulations to improve intestinal absorption of water-soluble compounds.

Animals↗

PubMed2004

Defensive chemicals of two species of Trachypachus Motschulski.

Analyses of pygidial gland contents of two species of a previously uninvestigated family of beetles (Trachypachidae) by Gas Chromatography-Mass Spectrometry (GC-MS) revealed that their chemistry is similar to that reported from many members of the family Carabidae. Nevertheless, the composition of defensive gland fluids of the two species Trachypachus slevini and T. gibbsii differs sufficiently to distinguish between the two species solely on the basis of their defensive chemistry. The major components of T. slevini glandular fluid are methacrylic, tiglic, and octanoic (= caprylic) acids, together with the hydrocarbon (Z)-9-pentacosene. In contrast, the glandular contents of T. gibbsii contain a rather unique mixture of polar and nonpolar compounds, the principal constituents of which are methacrylic and ethacrylic acids (= 2-ethylacrylic acid), together with 2-phenylethanol, 2-phenylethyl methacrylate, 2-phenylethyl ethacrylate, and (Z)-9-pentacosene.

Animals↗

PubMed2001

Biomechanical measurements in microscopically thin stratum comeum using acoustics.

BACKGROUND/AIMS: This study investigated whether a scanning acoustic microscope (SAM) could be developed to measure changes in the mechanical properties of the microscopically thin external layer of skin, the stratum corneum. The adapted microscope was used to determine the effects of various aqueous reagents, as compared with water, on the thickness, density, compression wave velocity and elastic constant, using 10 microm thin sections of human skin. METHODS: Specimens were exposed to aqueous solutions of glycerol, sodium chloride and alpha-hydroxy caprylic acid (HCA) to investigate permeation and to investigate the effect of these solutions on the above physical properties for signal transmission at a centre frequency of approximately 650 MHz in a path parallel to the epidermal layers. RESULTS: The system of measurement was found to give repeatable results and to provide a reliable indicator of the change in mechanical properties of the stratum corneum that arise from imbibition with different substances. Acoustic measurements of untreated specimen thickness and density agreed well with optical measurements and with previously published measurements, respectively. The trend in change of elastic moduli, however, was not in agreement with the results of the large-scale extensibility tests of Takahashi et al. and Hall & Hill, which used thicker specimens that contained additional epidermal or dermal layers. CONCLUSION: Disparate trends in elastic moduli were believed to be due to the strain rate dependence of the tissues and the different rates of loading applied during testing.

Acoustics↗

PubMed2002

Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length.

BACKGROUND: Unsaturated fatty acids are known as neutrophil activators. In the present study we investigated whether saturated triglycerides and fatty acids may also contribute to the previously observed activation of neutrophils by nutritional lipid emulsions. Furthermore we tested the hypothesis that carbon-chain length is of importance in this respect. MATERIALS AND METHODS: Neutrophils (1 x 10(6) mL(-1)) were isolated from the blood of nine volunteers. Chemiluminescence was used to evaluate neutrophil activation, characterized by the production of oxygen radicals by neutrophils during incubation with 1 mmol L(-1) saturated fatty acid (6-20 carbon) or triglycerides (6-12 carbon fatty acid), dissolved in aqueous medium by preparing micelles with dipalmitoyl phosphatidylcholine (DPPC). Results were expressed as means +/- SEMs of the overall luminescence signal relative to the signal of cells incubated in medium. RESULTS: Similar to a positive control, the polyunsaturated fatty acid arachidonic acid (C20 : 4), the triglycerides tricaproin (TC6 : 0), tricaprylin (TC8 : 0) and trilaurin (TC12 : 0) as well as the fatty acids lauric acid (C12 : 0), palmitic acid (C16 : 0), stearic acid (C18 : 0) and arachidic acid (C20 : 0) all induced oxygen radical production in neutrophils, while the medium-chain triglyceride tricaprin (TC10 : 0) and fatty acids caproic acid (C6 : 0), caprylic acid (C8 : 0) and capric acid (C10 : 0) exerted no clear effects, similar to negative controls (DPPC and glycerol). CONCLUSIONS: Besides their (poly)-unsaturated counterparts, saturated triglycerides and fatty acids also activate neutrophils. Carbon chain-length is pivotal in the interaction of fatty acids and triglycerides and cells of the immune system.

Adult↗

PubMed1996

Production of high levels of 8:0 and 10:0 fatty acids in transgenic canola by overexpression of Ch FatB2, a thioesterase cDNA from Cuphea hookeriana.

The Mexican shrub Cuphea hookeriana accumulates up to 75% caprylate (8:0) and caprate (10:0) in its seed oil. An acyl-ACP thioesterase cDNA from C. hookeriana, designated Ch FatB2, has been identified, which, when expressed in Escherichia coli, provides thioesterase activity specific for 8:0- and 10:0-ACP substrates. Expression of this clone in seeds of transgenic canola, an oilseed crop that normally does not accumulate any 8:0 and 10:0, resulted in a dramatic increase in the levels of these two fatty acids accompanied by a preferential decrease in the levels of linoleate (18:2) and linolenate (18:3). The Ch FatB2 differs from Ch FatB1, another Cuphea hookeriana thioesterase reported recently, in both substrate specificity and expression pattern. The Ch FatB1 has a broad substrate specificity with strong preference for 16:0-ACP and is expressed throughout the plant; whereas Ch FatB2 is specific for 8:0/10:0-ACP and its expression is confined to the seed. It is proposed that the amplified expression of Ch FatB2 in the embryo provides the hydrolytic enzyme specificity determining the fatty acyl composition of Cuphea hookeriana seed oil.

Amino Acid Sequence↗

PubMedDate not supplied

Serologic activity of fatty acid dependent antibodies in albumin-free systems.

Fatty acid dependent agglutinin (FADA) refers to serum with the special ability to cause agglutination of red blood cells in the presence of certain fatty acids. The agglutinating mechanism is unclear. It has been proposed that the agglutinin reacts with albumin that has been conformationally altered by sodium caprylate and that the immune complex is passively adsorbed onto red blood cells. This report presents data that contradicts the proposal assigning a specific role to albumin in the agglutinating mechanism. FADA were isolated by column chromatography of resolubilized euglobulin preparations. No evidence of contamination with albumin was obtained in those IgM fractions possessing FADA activity. We propose, as an alternative explanation, that the serologic activity of FADA depends upon the interaction of IgM agglutinins with haptenic fatty acids.

Antibody Specificity↗

PubMed2005

The highly abundant protein Ag-lbp55 from Ascaridia galli represents a novel type of lipid-binding proteins.

Lipid-binding proteins exhibit important functions in lipid transport, cellular signaling, gene transcription, and cytoprotection. Their functional analogues in nematodes are nematode polyprotein allergens/antigens and fatty acid and retinoid-binding proteins. This work describes a novel 55-kDa protein, Ag-lbp55, purified from the parasitic nematode Ascaridia galli. By direct N-terminal sequencing, a partial amino acid sequence was obtained that allowed the design of oligonucleotide primers to obtain the full-length cDNA sequence. Sequence analysis revealed the presence of an N-terminal signal peptide of 25 amino acid residues and a FAR domain at the C terminus. Data base searches showed almost no significant homologies to other described proteins. The secondary structure of Ag-lbp55 was predominantly alpha-helical (65%) as shown by CD spectroscopy. It was found to bind with high affinity fatty acids (caprylic, oleic, and palmitic acid) and their fluorescent analogue dansylaminoundecanic acid. Immunolocalization showed that Ag-lbp55 is a highly abundant protein, mainly distributed in the inner hypodermis and extracellularly in the pseudocoelomatic fluid. A similar staining pattern was observed in other pathogenic nematodes, indicating the existence of similar proteins in these species.

Amino Acid Sequence↗

PubMed1993

Improvement of dietary protein utilisation in chicks by medium chain triglyceride.

1. To improve the influence of variation of ME intake, an experiment was carried out using equalized feeding to investigate the comparative effects on protein and energy utilisation in chicks of diets containing medium chain triglyceride (MCT) and long chain triglyceride (LCT). Experimental diets were given at 3 different food intakes, namely, 100, 120 or 147 g/bird/10 d. The diets contained MCT or LCT on an isoenergetic basis. Maize oil and caprylic acid triglyceride respectively, were used as LCT and MCT sources. 2. Body weight gain and food efficiency of chicks significantly increased with the supplement of dietary MCT compared with dietary LCT at all food intakes. Protein retention and the efficiency of protein utilisation (protein retained/protein intake) at all food intakes also significantly increased with dietary MCT, while body fat and fat retention were significantly reduced. Chicks fed the LCT-supplemented diet, on the other hand, had a lower protein retention, but significantly higher fat retention. The value for energy retention and the efficiency of energy utilisation (energy retained/ME intake) were not significantly different between MCT- and LCT-supplemented diets. 3. It was concluded that supplementing MCT to the chick diet would improve body weight gain and protein utilisation while regulating fat deposition compared to the LCT supplemented diet, under equalized feeding conditions.

Adipose Tissue↗

PubMed2004

Gastrointestinal absorption enhancement of insulin by administration of enteric microspheres and SNAC to rats.

The preparation and characteristics of insulin enteric microspheres (EMS) were studied and the gastrointestinal absorption enhancement of insulin by co-administering EMS with sodium N-(8-[2-hydroxybenzoyl] amino) caprylate (SNAC) was determined. The w/o/w and o(1)/o(2) emulsion solvent evaporation methods were used to prepare insulin-hydroxypropyl methylcellulose phthalate (HPMCP) EMS. High-performance liquid chormatography determined the drug loading, entrapment efficiency, stability to pepsin, and drug dissolution rate in hydrochloric acid solution (pH 1.2) and phosphate buffer solution (pH 6.8). The hypoglycaemic effect was studied by orally administrating the insulin EMS and SNAC to rats. The particle size of EMS (o(1)/o(2)) and EMS (w/o/w) was about 500 and 30 micro m respectively, and drug loading was 7 and 3% respectively. After being incubated with 18 micro g/mL pepsin solution (pH 1) at 37 degrees C, only 20% of insulin in EMS (o(1)/o(2)) was digested within 4 h, while 60% of the insulin in EMS (w/o/w) was digested within 1 h. In hydrochloric acid solution (pH 1.2), EMS (o(1)/o(2)) had less drug dissolution than EMS (w/o/w). In phosphate buffer solution (pH 6.8), the entire drug release time of EMS (o(1)/o(2)) and EMS (w/o/w) was 75 and 10 min, respectively. After orally administering with SNAC, EMS (o(1)/o(2)) could decrease the blood glucose level of rats remarkably and maintain the hypoglycaemic effect for 4 h, while EMS (w/o/w) had just a weakly hypoglycaemic effect. The results showed that the characteristics-optimized EMS, i.e. EMS (o(1)/o(2)) incorporating SNAC, could enhance insulin absorption significantly in the gastrointestional tract by taking advantage of both protection from enzyme degradation and improvement of drug permeability.

Administration, Oral↗

PubMed1975

Purification of fibrinogen using cationic detergent.

Stearyltrimethylammonium chloride was used to isolate human fibrinogen, and purified protein was obtained by removing the detergent bound to it. Medium consisting of 0.015--0.03 mM fibrinogen-detergent complex, 0.85 M NaCl, 0.03 M sodium caprylate, and 30 per cent ethanol was found to be effective for renaturation of fibrinogen from the complex. The purified fibrinogen did not form any fibrils on incubation for 15 days with Ca-2+ at pH 7.2, and 37 degrees. The clottability of the purified fibrinogen was over 99 per cent. Immunochemical studies showed that the purified fibrinogen produced one precipitation line with a mixture of anti-human fibrinogen and anti-human serum. Although highly purified, the fibrinogen preparation still contained a trace of plasminogen.

Calcium↗

PubMed2001

Orally active heparin and low-molecular-weight heparin.

The heparins, (unfractionated heparin (UFH) and low-molecular-weight heparins (LMWH)) given by subcutaneous or intravenous injection have been used extensively in the prevention and treatment of both venous and arterial thromboembolic disorders. The increasing use of the heparins, LMWHs in particular, in the out of hospital setting has stimulated interest in the development of orally absorbable antithrombotic agents that require little or no monitoring, and this includes the heparins. UFH or LMWH delivered orally has been shown to have an antithrombotic effect in animal thrombosis models although there is little change in plasma coagulation tests. The addition of a simple organic chemical N -(8-(2-hydroxybenzoyl)amino)caprylate (SNAC) to UFH markedly enhances its absorption. A phase II study in patients undergoing total hip replacement indicated that SNAC heparin in two different doses was as effective and safe as UFH given subcutaneously. A phase III clinical trial comparing two doses of SNAC heparin given orally with LMWH by subcutaneous injection for the prevention of venous thromboembolism in patients undergoing total hip replacement is currently underway.

Administration, Oral↗

PubMed1996

Two novel thioesterases are key determinants of the bimodal distribution of acyl chain length of Cuphea palustris seed oil.

The seed oil of Cuphea palustris has an unusual fatty-acyl composition, whereby the principal fatty-acyl groups, myristate (64%) and caprylate (20%), differ by more than two methylenes. We have isolated two thioesterase (TE) cDNAs from C. palustris, encoding proteins designated Cp FatB1 and Cp FatB2, which, when expressed in Escherichia coli, have TE activities specific for 8:0/10:0- and 14:0/16:0-acyl carrier protein substrates, respectively. The specific activities of the recombinant affinity-purified enzymes indicate that Cp FatB2 is kinetically superior to Cp FatB1. This result is consistent with the predominance of 14:0 in the seed oil, despite apparently equal mRNA abundance of the two transcripts in the seed. In C. palustris the expression of both sequences is confined to the seed tissues. Based on these findings we propose that these two enzymes are major factors determining the bimodal chain-length composition of C. palustris oil. Analysis of the immature and mature seed oil by reverse-phase high-performance liquid chromatography confirmed that the principal triglycerides contain both 8:0 and 14:0. This result indicates that both fatty acids are synthesized at the same time and in the same cells at all developmental stages during oil deposition, suggesting that the two TEs act together in the same fatty acid synthesis system.

Amino Acid Sequence↗

PubMed2004

A novel per-oral insulin formulation: proof of concept study in non-diabetic subjects.

AIMS: The aim of our study was to examine the absorption of insulin from the gastrointestinal (GI) tract, using a novel oral formulation-adding a delivery agent SNAC (sodium N-[8-(2-hydroxybenzoyl)amino] caprylate) in combination with insulin. METHODS: Capsules containing insulin and SNAC, in various combinations, were administered orally, as a single dose, to 12 non-diabetic subjects and four control subjects (receiving SNAC or insulin only) in order to assess its biological effect and safety. Plasma glucose levels, insulin and C-peptide concentrations, as well as SNAC levels, were determined, at timed intervals up to 4 h. RESULTS: In all cases, a glucose-lowering effect was demonstrated, preceded by an increase in plasma insulin levels. The nadir of plasma glucose levels appeared after 30-50 min, following the ingestion of the mixture. The plasma insulin levels were found to parallel the blood SNAC levels. Plasma C-peptide levels were suppressed by the lowered glucose levels achieved concurrent with the increasing amount of exogenous insulin absorbed, indicating that the secretion of endogenous hormone was partially abolished. There were no biological effects regarding blood glucose levels upon administration of SNAC or insulin when given alone. No adverse effects were detected during the trial or several weeks after the trial. CONCLUSIONS: Insulin in combination with a novel delivery agent, SNAC, given orally, is absorbed through the GI tract in a biologically active form. This was demonstrated by a glucose lowering effect of the mixture as well as a suppression of an endogenous insulin secretion.

Absorption↗

PubMedDate not supplied

Cost savings from intravenous immunoglobulin manufactured from chromotography/caprylate (IGIV-C) in persons with primary humoral immunodeficiency disorder.

OBJECTIVE: Human intravenous immunoglobulin manufactured with chromatography and caprylate methods (IGIV-C, 10%) was associated with a reduction in validated infections (pneumonia and sinusitis) compared with treatment with a licensed immunoglobulin product manufactured using standard solvent-detergent methods (IGIV-SD, 10%) in participants with primary humoral immunodeficiency disorder (PIDD). Our objective was to determine the cost-consequences of using IGIV-C instead of IGIV-SD. METHODS: Economic analysis of a double-blind, randomized, clinical trial was used. Participants were randomly assigned to IGIV-C (N = 87) or IGIV-SD (N = 85) and monitored for the development of validated infections over the course of 9 months. Consumed resources were enumerated including cost of physician and emergency room visits, medications (prescription and over-the-counter), work productivity losses, and hospitalizations. Resource data was obtained from case report forms, patient diaries and the trial medication database. Because the amount of IGIV-SD used exceeded that of IGIV-C (nonstatistically significant difference) and the products are equivalently priced, we conservatively excluded investigational product acquisition cost to avoid artificially biasing incremental cost differences. We used a societal perspective with indirect costs, measured in 2003 US dollars. Pricing of both IGIV products is anticipated to be equivalent. RESULTS: In a multivariate analysis, annual mean per participant costs were significantly lower between those receiving IGIV-C compared with IGIV-SD for prescription medications [-US 302 dollars, 95% confidence interval (CI) -US 598 dollars to -US 6 dollars], hospitalization (-US 1454 dollars, 95% CI -US 1828 dollars to -US 1080 dollars) and total costs (-US 1304 dollars, 95% CI -US 1867 dollars to -US 742 dollars). Costs associated with lost work productivity and physician visits were similar in both groups (P > 0.10). In sensitivity analyses, varying costs of concomitant medications, hospitalization and outpatient care, did not significantly change our results. CONCLUSION: IGIV-C is cost-saving compared with IGIV-SD among persons with PIDD.

Adult↗

PubMed1977

Bilirubin displacing effect of stabilizers added to injectable preparations of human serum albumin.

Stabilizers added to preparations of human serum albumin before heat treatment were tested for bilirubin displacing effect, using the peroxidase method. It was found that N-acetyltryptophan and sodium caprylate displace bilirubin from its complex with human serum albumin in vitro. The quantitative findings were used for a rough estimate of the effect of these substances on the free bilirubin concentration in blood plasma, expected when stabilized albumin preparations are given intravenously for prevention of kernicterus. The calculated effect is a delay of the decrease of free bilirubin concentration, or even a temporary increase. Sodium mandelate displaces less strongly.

Bilirubin↗