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PubMed2004

Structural determination and histochemical localization of ghrelin in the red-eared slider turtle, Trachemys scripta elegans.

We purified ghrelin peptide and determined the cDNA sequence encoding the precursor protein from the stomach of the red-eared slider turtle, Trachemys scripta elegans. The Trachemys ghrelin is comprised of 25-amino acids and has the sequence GSSFLSPEYQNTQQRKDPKKHTKLN. The third serine residue was modified by n-octanoic (C8:0), decanoic (C10:0) or unsaturated decanoic acid (C10:1). The carboxyl-terminal end of the peptide was not amidated, as seen in the ghrelins of other land vertebrates. Quantitative real-time PCR analysis revealed high levels of gene expression in the stomach and moderate levels in the large intestine and pancreas. Histochemical studies of turtle stomach revealed that ghrelin-immunopositive (ghrelin-ip) cells, which were small and round, were observed in the mucosal layer of the stomach but not in the myenteric plexus, and ghrelin-mRNA-expressing (ghrelin-ex) cells detected by in situ hybridization were scattered in a similar distribution as ghrelin-ip cells. These results indicate that ghrelin is present in reptiles.

Amino Acid Sequence↗
PubMed2001

Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior.

The solubilization of hydrophilic and lipophilic molecules, with biological relevance, in the monoolein/water (MO/W) system has been investigated for phase behavior. Small angle X-ray scattering (SAXS), nuclear magnetic resonance (NMR) and optical microscopy (OM) have been used to characterize the microstructure of the liquid crystalline phases. Partial phase diagrams of the MO/W system in the presence of sodium decanoate, 1-adamantanamine hydrochloride, decanoic and dodecanoic acids, acetyl salicilic acid and retinol have been determined. The stability of the various phases has been followed for at least eight months. The polarity and the molecular structure of the additive determine whether it is located at the polar interface or in the apolar region of the lipid layer. Therefore, the additive affects the interfacial curvature of the lipid layer differently, which in turn will trigger transition to disparate phases. A cubic-to-reverse hexagonal phase transition has been observed with time for most of the ternary systems, with the exception of 1-adamantanamine hydrochloride and retinol. The release of free glycerol and oleic acid due to MO hydrolysis has been clearly demonstrated by 13C NMR. This would account for the changes in phase behavior observed with time. The released oleic acid, located in the MO acyl chain region, favors the inverse interfacial curvature. The average lipid dimensions in the cubic and in the reverse hexagonal phases have been calculated from SAXS data.

Carbon Isotopes↗
PubMed1999

High-performance liquid chromatography method for the characterization of rhamnolipid mixtures produced by pseudomonas aeruginosa UG2 on corn oil.

A HPLC method was developed to quantify rhamnolipid species in a bacterial biosurfactant mixture. The biosurfactant mixtures containing mainly 3-[3'-(L-rhamnopyranosyl-oxy)decanoyloxy]decanoic acid (RhC10C10), 3-[3'-(2'-O-alpha-L-rhamnopyranosyl-oxy)decanoyloxy]decanoic acid (Rh2C10C10), 3-[3'-(2'-O-alpha-L-rhamnopyranosyl-oxy)decanoyloxy]dodecanoic acid (Rh2C10C12), and a dehydrogenated variety of the latter, 3-[3'-(2'-O-alpha-L-rhamnopyranosyl-oxy)decanoyloxy]dodecenoic acid (Rh2C10C12-H2), were isolated from Pseudomonas aeruginosa UG2 cultures grown on corn oil as sole carbon. The rhamnolipid species were identified and quantified after their derivatization to the corresponding phenacyl esters. To confirm the reliability of the HPLC method, the biosurfactant mixtures and the HPLC isolated species were further analyzed. Mass spectroscopy (electrospray ionization and atmospheric pressure chemical ionization techniques) was used to confirm their molecular mass, gas chromatography to verify their fatty acid content, and a colorimetric assay to quantify the rhamnose content.

Carbohydrate Sequence↗
PubMed2001

Measurement of androgen and estrogen receptors in breast tissue from subjects with anabolic steroid-dependent gynecomastia.

In order to assess the relationship between anabolic steroid administration and gynecomastia, we studied the effects produced by administering nandrolone decanoate and a mixture of propionate, phenilpropionate, isocaproate and testosterone decanoate to bodybuilders during a six month period. The following significant changes occurred: a 53% reduction in serum testosterone; LH and FSH levels were suppressed to 77% and 87%, respectively, in comparison to control values; and although 45% of the subjects showed an increase in serum estradiol levels, no statistically significant differences were found compared with control estradiol levels. With regard to estradiol and androgen receptors, 85% of gynecomastia tissue contained estradiol or androgen receptors, while 40% contained both. The mean values of estradiol and androgen receptors in the cytosol were 65 +/- 10 and 52 +/- 5 fmol/mg protein, respectively. Nuclear androgen and estradiol receptor levels were 33 +/- 7 and 67.5 +/- 9 fmol/mg protein, respectively. The presence of hormone receptors in gynecomastia receptive cells provides support for the hypothesis that gynecomastia is steroid-dependent.

Adult↗
PubMed2000

Anti-HIV-1 phorbol esters from the seeds of Croton tiglium.

Five phorbol diesters, together with three known ones, were isolated from a MeOH extract of the seeds of Croton tiglium, and their structures were determined by spectroscopic methods and selective hydrolysis of acyl groups. These compounds were assessed for their abilities to inhibit an HIV-induced cytopathic effect (CPE) on MT-4 cells and to activate protein kinase C (PKC) associated with tumor-promoting action. 12-O-Acetylphorbol-13-decanoate and 12-O-decanoylphorbol-13-(2-methylbutyrate) effectively inhibited the cytopathic effect of HIV-1 [complete inhibitory concentration (IC100) values of 7.6 ng/ml and 7.81 microg/ml, and minimum cytotoxic concentration (CC0) value of 62.5 and 31.3 microg/ml, respectively]; however, 12-O-acetylphorbol-13-decanoate showed no activation of PKC at concentrations of 10 and 100 ng/ml. 12-O-Tetradecanoylphorbol-13-acetate (TPA) was found to be not only the most potent inhibitor of HIV-1-induced CPE (IC100 value of 0.48 ng/ml), but also the most potent activator of PKC (100% activation at 10 ng/ml).

Animals↗
PubMed1999

Depressive symptoms and schizophrenic relapses: the effect of four neuroleptic drugs.

1. A prevalence of depressive symptomatology, ranging from 25% to 80% has been reported during the course of schizophrenia. 2. Depressive symptoms were assessed in 144 schizophrenic patients (DSM IV) during an acute exacerbation phase. 3. Depressive symptoms showed a prevalence ranging from 5.5% (severe clinical pictures) to 54.8 (mild clinical pictures). 4. The authors did not find a correlation between depressive symptoms per se and the presence of negative psychotic symptoms. Depression may be linked not so much to negative symptoms but to the psychotic state itself. 5. Depressive symptomatology concurrently occurred with schizophrenic relapses and improved together with the psychotic clinical picture, independently of the neuroleptic drug employed. Haloperidol, haloperidol decanoate and fluphenazine decanoate all showed a similar improvement of depressive symptoms. 6. L-sulpiride showed a trend to be most effective on depressive symptomatology in comparison to the other neuroleptics.

Adolescent↗
PubMed2001

Effect of flupenthixol on subjective and cardiovascular responses to intravenous cocaine in humans.

The effects of oral flupenthixol and intramuscular (i.m.) flupenthixol decanoate in combination with intravenous (i.v.) cocaine were evaluated in male cocaine abusers. Participants resided at an inpatient research unit for 27 days followed by an 11-day outpatient period. Oral flupenthixol (2.5 or 5.0 mg; p.o.) followed by flupenthixol decanoate (10 or 20 mg; i.m.) and placebo were investigated in individuals who were randomly assigned to one of three groups under double-blind conditions (placebo, low or high dose flupenthixol). During the inpatient period, participants had four fixed cocaine dosing sessions; each session they were administered four doses of i.v. cocaine (approx. 48 mg/70 kg), spaced 14 min apart. These sessions occurred once before medication (baseline phase), once following oral medication (oral phase), and twice following intramuscular medication (IM phase). Out of 23 participants, 18 completed the study; 4 of the 5 non-completers were in the high dose flupenthixol group. Overall, there were few subjective, cardiovascular, or cocaine pharmacokinetic differences between the placebo group and the low dose flupenthixol group, indicating that the low dose of flupenthixol was well tolerated, but ineffective. In the high dose flupenthixol group, two out of seven individuals (29%) experienced a dystonic reaction following oral flupenthixol and were medically discharged. Taken together, these findings indicate that flupenthixol is not a good candidate for treating cocaine abusers.

Adult↗
PubMed1991

Cholesterol esterase catalyzed hydrolysis of mixed micellar thiophosphatidylcholines: a possible charge-relay mechanism.

Mechanistic features of cholesterol esterase catalyzed hydrolysis of two thiophospholipids, rac-1-(hexanoylthio)-2-hexanoyl-3-glycerophosphorylcholine (6TPC) and rac-1-(decanoylthio)-2-decano-yl-3-glycerophosphorylcholine (10TPC), have been characterized. The hydrolysis of 10TPC that is contained in mixed micelles with Triton X-100 occurs strictly at the micellar interface, since the reaction rate is independent of the micelle concentration but depends hyperbolically on the mole fraction of the substrate in the micelles. This latter observation allows one to calculate the interfacial kinetic parameters V*max and K*m. The hydrolyses of 10TPC and p-nitrophenyl butyrate are similarly inhibited by the transition state analogue inhibitor phenyl-n-butylborinic acid, and therefore, physiological and nonphysiological substrates are processed at the same active site. The similarity of k*cat values for the acyl-similar substrates 10TPC and p-nitrophenyl decanoate indicates that the phospholipase A1 activity of cholesterol esterase is partially rate limited by turnover of a decanoyl-enzyme intermediate. Solvent isotope effects on V*max and V*max/K*m (which monitors acylation only) are approximately 2-3 and are consistent with transition states that are stabilized by general acid-base proton transfers. Proton inventories of V*max/K*m indicate that simultaneous proton transfers stabilize the acylation transition state, which requires a multifunctional acid-base machinery (perhaps a charge-relay system) in the cholesterol esterase active site. Similar results are obtained for the 6TPC reaction, both in the presence and absence of Triton X-100 micelles.

Acetylcholinesterase↗
PubMed1998

Imidazolyl carboxylic acids as mechanistic probes of flavocytochrome P-450 BM3.

omega-Imidazolyl carboxylic acids (C10-C12) have been used as probes of the active site and catalytic mechanism of the fatty acid hydroxylase P-450 BM3 from Bacillus megaterium. These compounds are the most potent inhibitors of P-450 BM3 yet reported. All are mixed inhibitors, increasing the Km and decreasing the kcat for laurate oxidation. All ligate the P-450 BM3 ferric heme iron, inducing a type II shift in the Soret absorbance band from 419 to 424 nm. Binding to the ferrous form is much weaker. 10-(Imidazolyl)decanoic acid was the best inhibitor (Kic = 0.9 microM, Kiu = 5.7 microM), while 12-(imidazolyl)dodecanoic acid (Kic = 1.35 microM, Kiu = 6.9 microM) was superior to 11-(imidazolyl)undecanoic acid (Kic = 7.5 microM, Kiu = 16 microM). Dissociation constants for binding to oxidized P-450 BM3 heme iron were determined spectrophotometrically as 8 microM (C12 azole) and 27 microM (C11 azole). The binding of 10-(imidazolyl)decanoic acid was too tight for an absolute Kd to be determined spectrophotometrically, but this value is <0.2 microM. The binding of different fatty acids to the enzyme was found to have distinct effects on the Kd for the azoles. Laurate induced tighter binding (Kd for the C12 azole lowered to 4.7 microM), while arachidonate weakened the affinity (Kd increased to 23 microM). Arachidonate diminished the affinity for the C10 azole sufficiently that a Kd could be determined by spectrophotometric titration (11 microM). Affinity for the C12 azole was decreased in active-site-mutants R47G (R47 tethers the fatty acid carboxylate group) and F87Y but increased in mutant F87G-indicating an important role for this residue in determining heme accessibility. The C10 azole binds much more weakly to the spin-state-insensitive F87Y (32. 2 microM), suggesting that the inhibitors may bind preferentially to different conformers of P-450 BM3. NADP+ binding in the reductase also tightened affinity of these inhibitors for P-450 BM3 (Kd for the C12 azole decreased to 2.7 microM), but this effect was not observed for FMN-deficient mutant W574D, suggesting that the interdomain effect of NADP+ on inhibitor binding was mediated via flavin mononucleotide. Resonance Raman spectroscopy indicates that the inhibitors form low-spin complexes with P-450 BM3 and that their binding induces movements of the heme vinyls relative to the ring.

Arachidonic Acid↗
PubMed2001

Headspace solid phase microextraction (SPME) analysis of flavor compounds in wines. Effect of the matrix volatile composition in the relative response factors in a wine model.

The application of headspace solid phase microextraction (SPME) for flavor analysis has been studied. Headspace SPME sampling was tested for nine common wine flavor compounds in 10% (v/v) aqueous ethanol: linalool, nerol, geraniol, 3-methyl-1-butanol, hexanol, 2-phenylethanol, ethyl hexanoate, ethyl octanoate, and ethyl decanoate. The chemical groups (monoterpenoids, aliphatic and aromatic alcohols, and esters) showed specific behavior in SPME analysis. SPME sampling parameters were optimized for these components. Relative response factors (RRFs), which establish the relationship between the concentration of the compound in the matrix liquid solution and the GC peak area, were estimated for all compounds. Log(10)(RRF) varied from 0 (3-methyl-1-butanol) to 3 (ethyl decanoate), according to their molecular weight. Quantification by SPME was shown to be highly dependent on the matrix composition; the compounds with higher RRF were the less affected. As a consequence, the data obtained with this methodology should be used taking into consideration these limitations, as shown in the analysis of four monovarietal Bairrada white wines (Arinto, Bical, Cerceal, and Maria Gomes).

Chromatography, Liquid↗
PubMed2006

Competition and coadsorption of di-acids and carboxylic acid solvents on HOPG.

The self-assemblies of di-acids HOOC-(CH(2))(n)-COOH (n = 20, 18, 16, 14, 12, 10) in three solvents hexanoic acid, octanoic acid, and decanoic acid on highly oriented pyrolytic graphite (HOPG) were studied with scanning tunneling microscopy (STM). In the solvent hexanoic acid, solvent molecules coadsorb with HOOC-(CH(2))(n)-COOH (n = 20, 18, 16) via formation of hydrogen bonds. The solvent octanoic acid coadsorbs with HOOC-(CH(2))(n)-COOH (n = 20, 18). Decanoic acid only coadsorbs with HOOC-(CH(2))(20)-COOH. In each solvent, the trend of coadsorption between solvent molecules and di-acid molecules decreases with decreasing chain-length of di-acid molecules. These systematic investigations suggest that coadsorption of solvent molecules with di-acid solute molecules is mainly dependent on the relative hydrogen-bond densities in the formed monolayer. This is consistent with the maximization of adsorption heat of the self-assembled monolayers of di-acids dissolved in solvents of carboxylic acids.

Journal Article↗
PubMed2004

Preparation and characterization of n-alkanoic acid self-assembled monolayers adsorbed on 316L stainless steel.

The electrochemical formation and characterization of decanoic, myristic, palmitic, and stearic acid self-assembled monolayers on a native oxide surface of 316L stainless steel have been studied. This work describes a new approach to surface modification of stainless steel in which the self-assembly of n-alkanoic acids is facilitated by applying a potential to the stainless steel in an organic electrolyte solution. While decanoic acid forms a disorganized monolayer as a result of sweeping the potential in an acetonitrile solution containing 0.1 mM of the respective acid, longer acids, that is, myristic and palmitic acids, form highly ordered closed-packed monolayers. This electrochemical approach results in highly reproducible monolayers that are deposited within a shorter time than the traditional assembly process. The monolayers were characterized by cyclic voltammetry, double-layer capacity (ac voltammetry), contact angle measurements, X-ray photoelectron spectroscopy, and external reflection-absorption Fourier transform infrared spectroscopy. The utilization and implications of this modification technique are discussed.

Journal Article↗
PubMed2005

Coumarins from the fruits of Seseli devenyense.

Eight new coumarins were isolated from the fruits of Seseli devenyense Simonkai. Their structures were established from NMR and mass data and their absolute configurations from chemical degradation correlation reactions. The new structures are the decanoic and dodecanoic esters of (+)-lomatin (3, 4), the decanoates of (+)-cis-khellactone at positions 4' (5) and 3' (6) as well as the 2'S epimer of 8-(2,3-dihydroxy-3-methylbutyl)-7-hydroxychromen-2-one (7) named devenyol, its two O-monoglucosides at positions 3' and 7 named devenyosides A (8) and B (9), and the corresponding 3'- and 7-O-diglucoside named devenyoside C (10). This plant is an interesting example of stereochemical diversity based on biodiversity given that other members of the Apiaceae family produce exclusively the 2'R epimers of compounds 7-9.

Apiaceae↗
PubMed1997

In vitro human skin barrier modulation by fatty acids: skin permeation and thermal analysis studies.

PURPOSE: This study aims to elucidate the skin permeation enhancement and the skin perturbation effects of a number of fatty acids, i.e. straight-chain saturated (SFA), monounsaturated (MUFA) and polyunsaturated acids (PUFA). METHODS: The skin permeation enhancement effects were studied using human stratum comeum (SC) and p-aminobenzoic acid (PABA) as a model permeant. The fatty acids in propylene glycol (FA/PG) were applied according to a pre-treatment/co-treatment protocol. The perturbation effects were studied using differential thermal analysis (DTA) on SC after pretreatment with FA/PG. RESULTS: SFA with 6 to 12 carbons exhibit a parabolic correlation between enhancement effect and chain-length, with a maximum at nonanoic-decanoic acids (with 9 and 10 carbons). Nonanoic and decanoic acids exert barely noticeable effects on the thermal behaviour of SC, suggesting that they easily mix with the skin lipids. All cis-6-, 9-, 11- or 13-octadecenoic acids (MUFA) enhance the permeation of PABA to the same extent. DTA revealed that the cis-9- and 13-isomers form a separate domain containing mostly the pure fatty acids within the SC lipids and suppress the lipid transitions at 70 degrees/80 degrees C. PUFA--linoleic (LA), alpha-linolenic (ALA) and arachidonic acids--enhance PABA permeation stronger than MUFA but additional double bonds do not further increase the degree of enhancement. LA and ALA form separate domains but do not completely suppress the SC lipid transitions at 70 degrees/80 degrees C. Increase in the enthalpy changes of 70 degrees/80 degrees transitions linearly correlates to the decrease in the permeability coefficients, suggesting that an increased perturbation of the skin lipids not necessarily has to yield an increased PABA permeation. CONCLUSIONS: The enhancement effects of fatty acids on the PABA penetration through SC are structure-dependent, associated with the existence of a balance between the permeability of pure fatty acids across SC and the interaction of the acids to skin lipids.

4-Aminobenzoic Acid↗
PubMed2003

Evidence that antioxidants prevent the inhibition of Na+,K(+)-ATPase activity induced by octanoic acid in rat cerebral cortex in vitro.

The objective of the present study was to investigate the in vitro effects of octanoic acid, which accumulates in medium-chain acyl-CoA dehydrogenase (MCAD) deficiency and in Reye syndrome, on key enzyme activities of energy metabolism in the cerebral cortex of young rats. The activities of the respiratory chain complexes I-IV, creatine kinase, and Na+,K(+)-ATPase were evaluated. Octanoic acid did not alter the electron transport chain and creatine kinase activities, but, in contrast, significantly inhibited Na+,K(+)-ATPase activity both in synaptic plasma membranes and in homogenates prepared from cerebral cortex. Furthermore, decanoic acid, which is also increased in MCAD deficiency, and oleic acid strongly reduced Na+,K(+)-ATPase activity, whereas palmitic acid had no effect. We also examined the effects of incubating glutathione and trolox (alpha-tocopherol) alone or with octanoic acid on Na+,K(+)-ATPase activity. Tested compounds did not affect Na+,K(+)-ATPase activity by itself, but prevented the inhibitory effect of octanoic acid. These results suggest that inhibition of Na+,K(+)-ATPase activity by octanoic acid is possibly mediated by oxidation of essential groups of the enzyme. Considering that Na+,K(+)-ATPase is critical for normal brain function, it is feasible that the significant inhibition of this enzyme activity by octanoate and also by decanoate may be related to the neurological dysfunction found in patients affected by MCAD deficiency and Reye syndrome.

Animals↗
PubMed2002

The effects of drug abuse on the stress responsive hypothalamic-pituitary-adrenal axis and the dopaminergic and endogenous opioid systems.

OBJECTIVE: Drugs of abuse have a significant impact on the stress responsive hypothalamic-pituitary-adrenal (HPA) axis and an abnormal response to stress may mediate the development or maintenance of addictive diseases. In animals, drugs of abuse, such as cocaine, lead to an activation of the HPA axis. Drugs of abuse also have an impact on the endogenous opioid system (EOS) and the dopaminergic system. Each of these systems has also been implicated in the mediation of aggressive behaviors. This brief report focuses on the effects of drugs of abuse on the stress responsive HPA, EOS and dopaminergic systems, and the role of these systems in mediating aggression and comorbidity of substance abuse and aggressive behaviors. METHOD: Rodents were administered either 'binge' pattern cocaine (15 mg/kg x 3 each day) or the androgenic anabolic steroid nandrolone decanoate and the effects on mRNA levels, receptor binding and circulating levels of stress hormones were analyzed. RESULTS: Both cocaine and nandrolone decanoate significantly impact the HPA axis, the EOS and the dopaminergic systems. CONCLUSION: Drugs of abuse impact substantially the same neural systems that affect aggressive behavior.

Dopamine↗
PubMed1965

Incorporation of 14C-labelled fatty acids into the mammary-gland lipids of the lactating rabbit.

1. [1-(14)C]Stearic acid, [9-(14)C]stearic acid, [9-(14)C]palmitic acid and [9-(14)C]decanoic acid were fed to lactating rabbits, and the fatty acids of the mammary gland were separated and partially degraded. 2. Most of the (14)C recovered was located in the acids fed. Stearic acid was least efficiently absorbed; decanoic acid was the most extensively metabolized. 3. Resynthesis after degradation to C(2) units led to uniform alternate labelling in the C(2)-C(10) acids, whereas C(12)-C(18) acids had excess of (14)C at the carboxyl end. 4. Acids formed by beta-oxidation down to C(12), but not below, were also present in the mammary-gland lipids. Desaturation of the administered acids was a very minor reaction.

Animals↗
PubMed1972

Fatty acid biosynthesis in rabbit mammary gland during pregnancy and early lactation.

The pattern of fatty acids synthesized by mammary-gland explants from rabbits during pregnancy and early lactation has been studied. From day 12 to day 18 of pregnancy, long-chain (C(14:0)-C(18:1)) fatty acids were the major products. From day 18 to day 21 of pregnancy there was an increase of up to 12-fold in the rate of fatty acid synthesis per unit wet weight of tissue that was almost exclusively caused by the synthesis of octanoic fatty acid and decanoic fatty acid, which are characteristic of rabbit milk. These medium-chain fatty acids were mainly incorporated into triglycerides. From day 22 to day 27 of pregnancy there was little change in the rate of fatty acid synthesis and the proportions of fatty acids synthesized were essentially the same as those synthesized by the lactating gland, i.e. 80-90% octanoic acid plus decanoic acid. About 2-4 days before parturition a second lipogenic stimulus occurred, although the pattern of fatty acids synthesized did not change.

Acetates↗