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At least 469 records · Page 26Linked to original sources
PubMed2004

Simple synthesis of beta-D-glycopyranosides using beta-glycosidase from almonds.

Enzymatic glycosidation of twenty-one kinds of alcohols (n-hepanol, n-octanol, 2-phenylethanol, 3-phenylpropanol, 4-phenylbutanol, 5-phenylpentanol, 6-phenylhexanol, furfury alcohol, 2-pyridinemethanol, isobutanol, isopentanol, p-methoxycinnamylalcohol) including secondary alcohols (isopropanol, cyclohexanol, 1-phenylethanol) and 1,omega-alkanediols (1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol), salicyl alcohol and 4-nitrophenyl beta-D-glucopyranoside (5) using beta-glucosidase from almonds stereoselectively gave the corresponding beta-D-glucopyranosides in moderate yield.

Alcohols↗
PubMed2000

Absolute configuration of a ceramide with a novel branched-chain fatty acid isolated from the epiphytic dinoflagellate, Coolia monotis.

The absolute configuration of the chiral center at the C15 position of a novel branched-chain fatty acid derived from a new ceramide isolated from the epiphytic dinoflagellate Coolia monotis was determined to be of R from by reversed-phase HPLC after cleavage to 12-methylpentadecanoic acid and subsequent conversion with the chiral fluorescent reagent, (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanol.

Animals↗
PubMed2000

Purification and characterization of cyclohexanone 1,2-monooxygenase from Exophiala jeanselmei strain KUFI-6N.

Baeyer-Villiger cyclohexanone 1,2-monooxygenase (CHMO) was purified 17.1-fold from cell extracts of the fungus Exophiala jeanselmei grown on cyclohexanol to electrophoretically homogeneity by serial chromatographies. The molecular mass of the native enzyme was approximately 74 kDa by gel filtration and SDS-PAGE. Some enzymic characterizations were studied. The NH2-terminal amino acid residues were Ala-Lys-Ser-Leu-Asp-Val-Leu-Ile-Val-Gly-Ala-Gly-Phe-Gly-Gly-Ile-Tyr-Gln-Leu-, with similarity to the bacterial CHMOs of FAD-binding and NADPH-dependent type Baeyer-Villiger monooxygenases.

Amino Acid Sequence↗
PubMed2002

Determination of the absolute configurations of the anteiso acid moieties of glycoglycerolipid S365A isolated from Corynebacterium aquaticum.

The absolute configurations of the two acid moieties, 12-methyltetradecanoate and 14-methylhexadecanoate, of glycoglycerolipid S365A isolated from Corynebacterium aquaticum were determined by an HPLC analysis after their conversion with the chiral fluorescent labeling reagents, (1S,2S)- and (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanol. Both anteiso acids had the S configuration.

Chromatography, High Pressure Liquid↗
PubMed2005

Isolation and functional analysis of cytochrome P450 CYP153A genes from various environments.

The cytochrome P450 CYP153 family is thought to mediate the terminal hydroxylation reactions of n-alkanes. We isolated 16 new P450 CYP153A genes (central region) from various environments such as petroleum-contaminated soil and groundwater, as well as one from the n-alkane-degrading bacterium Alcanivorax borkumensis SK2 (designated P450balk). The sequences of the new P450 genes were extended by PCR to generate full-length chimeric P450 genes, using the N- and C-terminal domains of P450balk. A differential CO-reduced P450 spectral analysis indicated that 8 P450 genes among the 16 chimeric genes were expressed in Escherichia coli to generate a soluble and functional enzyme. The several functional chimeric P450s and P450balk were further fused to the reductase domain of the self-sufficient P450 monooxygenase (P450RhF) at the C-terminus. E. coli cells expressing these self-sufficient P450 chimeric genes converted n-alkanes, cyclohexane, 1-octene, n-butylbenzene, and 4-phenyl-1-butene into 1-alkanols, cyclohexanol, 1,2-epoxyoctane, 1-phenyl-4-butanol, and 2-phenethyl-oxirane, respectively.

Alkanes↗
PubMed2006

ERK-dependent modulation of cerebellar synaptic plasticity after chronic Delta9-tetrahydrocannabinol exposure.

Chronic exposure to Delta9-tetrahydrocannabinol (THC) induces tolerance to cannabinoid-induced locomotor effects, which are mediated by cannabinoid receptors (CB1Rs) located in motor control regions, including the cerebellum. There is substantial evidence of cerebellar CB1R molecular adaptation and modifications in receptor signaling after prolonged cannabinoid exposure. However, very little is known about the effects of chronic cannabinoid administration on cerebellar synaptic plasticity, which may contribute to the development of cannabinoid behavioral tolerance. In the cerebellar cortex, activation of CB1R inhibits excitatory synaptic transmission at parallel fiber (PF)-Purkinje cell (PC) synapses by decreasing neurotransmitter release. Our study aimed to investigate the neurophysiological adaptive responses occurring at cerebellar PF-PC cell synapses after repeated THC exposure. In THC-tolerant mice, an increase of the basal release probability was found at PF-PC synapses, in parallel with a facilitation of slow mGluR1 (metabotropic glutamate receptor type 1)-mediated excitatory postsynaptic currents and a reduced sensitivity to the inhibitory effects of the CB1R agonist CP55,940 [(-)-cis-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl)cyclohexanol]. Additionally, after repeated THC exposures, presynaptic PF-PC long-term potentiation was blocked by A1R (adenosine receptor-1) activation. Inhibition of the extracellular signal regulated kinase (ERK) pathway prevented these alterations of cerebellar synaptic transmission and plasticity. In summary, we provide evidence for ERK-dependent modulatory mechanisms at PF-PC synapses after chronic THC administration. This contributes to generation of forms of pathological synaptic plasticity that might play a role in cannabinoid dependence.

Animals↗
PubMed2004

Alumina-based fiber for solid phase microextraction of alcohols from gaseous samples.

On the basis of the affinity of alumina towards hydroxyl functional groups, a solid phase microextraction (SPME) fiber was constructed using alumina powder and poly(vinyl chloride) (PVC). Different compositions were tested and alumina:PVC (97:3) was selected as an optimun composition. A piece of silver wire was used as fiber support. The fiber producing was simple and could be completed in a few minutes. The mechanical durability of the fiber was so good that only a single fiber was used during this study. Ethanol, 1-butanol, 2-butanol, 1-pentanol, 2-pentanol and cyclohexanol were selected as target analytes. Finally, ethanol concentration in the fruit juices and vinegar was measured using SPME-capillary gas chromatography followed by flame ionization detection.

Journal Article↗
PubMed2005

Retentivity and enantioselectivity of uniformly-sized molecularly imprinted polymers for (S)-nilvadipine in aqueous and non-aqueous mobile phases.

Uniformly-sized molecularly imprinted polymers (MIPs) for (S)-nilvadipine have been prepared by a multi-step swelling and polymerization method using methacrylic acid or 4-vinylpyridine (4-VPY) as a functional monomer, ethylene glycol dimethacrylate (EDMA) as a cross-linker, and toluene, chloroform, cyclohexanol or phenylacetonitrile as a porogen. The chiral recognition abilities of the MIPs for nilvadipine were evaluated using aqueous and non-aqueous mobile phases. Among the MIPs, the (S)-nilvadipine-imprinted 4-VPY-co-EDMA polymers prepared using toluene as a porogen showed the highest recognition ability for nilvadipine in both aqueous and non-aqueous mobile phases. In addition to molecular shape recognition, hydrogen-bonding interactions of the NH proton of nilvadipine with a pyridyl group of the (S)-nilvadipine-imprinted 4-VPY-co-EDMA polymers could play an important role in the retention and chiral recognition of nilvadipine in aqueous and non-aqueous mobile phases. Furthermore, the MIP for (S)-nilvadipine gave the highest molecular recognition ability when a porogenic solvent during polymerization was used as the mobile phase modifier.

Chromatography, High Pressure Liquid↗
PubMed1996

A risk-benefit assessment of tramadol in the management of pain.

Tramadol is a cyclohexanol derivative with mu-agonist activity. It has been used as an analgesic for postoperative or chronic pain since the late 1970s, and became one of the most popular analgesics of its class in Germany. International interest has been renewed during the past few years, when it was discovered that tramadol not only acts on opioid receptors, but also inhibits serotonin (5-hydroxytryptamine; 5-HT) and noradrenaline (norepinephrine) reuptake. This review aims to provide a risk-benefit assessment of tramadol in the management of acute and chronic pain syndromes. Tramadol has been used intraoperatively as part of balanced anaesthesia. Such use is under discussion, however, as it was associated with a high incidence of intraoperative recall and dreaming, and postoperative respiratory depression has been described after intraoperative administration of high doses. Postoperatively, intravenous and intramuscular tramadol has been used with good efficacy. Analgesic doses were comparable with pethidine (meperidine) and 10 times higher than morphine. Nausea and vomiting were the most frequently reported adverse effects. In controlled studies, haemodynamic and respiratory parameters were only minimally impaired. The risk of severe respiratory depression in typical dosages is negligible in comparison with other opioids used for postoperative pain management. Tramadol has been used with good results for the management of labour pain without respiratory depression of the neonate. It was also effective for the treatment of pain from myocardial ischaemia, ureteric colic and acute trauma. Good results have been published for cancer pain management with tramadol in several studies. The potential for abuse or addiction seems to be minimal, and serious complications have not been reported. For patients with severe pain, the efficacy of morphine is superior, and most patients with adequate analgesia from tramadol had to be changed to a more potent opioid after a few weeks due to increased nociceptive input during tumour progression. Tramadol can be recommended as a safe and efficient drug for step II according to the World Health Organization guidelines for cancer pain management.

Administration, Oral↗
PubMed1987

Metabolism of beta-myrcene in vivo and in vitro: its effects on rat-liver microsomal enzymes.

Metabolites isolated from the urine of rats after oral administration of beta-myrcene (I) were: 10-hydroxylinalool (II), 7-methyl-3-methylene-oct-6-ene-1,2-diol (IV), 1-hydroxymethyl-4-isopropenyl cyclohexanol (VI), 10-carboxylinalool (III) and 2-hydroxy-7-methyl-3-methylene-oct-6-enoic acid (V). Liver microsomes prepared from phenobarbital-treated rats convert beta-myrcene (I) to 10-hydroxylinalool (II) in the presence of NADPH and oxygen. NADH neither supported this reaction nor did it show any synergistic effect. The rate of conversion was significantly greater in microsomes prepared from phenobarbital-treated rats than from 3-methylcholanthrene-treated or control microsomal preparations. The formation of 10-hydroxylinalool (II) was inhibited by metyrapone, carbon monoxide, SKF-525A, p-chloromercuric benzoate (p-CMB) and cytochrome c. Titration of phenobarbital-induced liver microsomes with beta-myrcene (I) produced a series of type I difference spectra with peaks around 387-390 nm and troughs around 421-425 nm. The Ks for beta-myrcene was 10.6 microM. Administration (four days) of beta-myrcene (I) to rats did not result in any significant effect on the hepatic drug-metabolizing enzymes.

Acyclic Monoterpenes↗
PubMed1988

Oxidative deamination of alicyclic primary amines by liver microsomes from rats and rabbits.

1. Substrate selectivity and species difference in the oxidative deamination of the alicyclic primary amines, cyclopentylamine, cyclohexylamine, cycloheptylamine, 1- and 2-aminoindane, and 1- and 2-aminotetralin were studied using liver microsomes from rats and rabbits. 2. The deamination rates of the amines were much greater with liver microsomes from rabbits than from rats. Substrate selectivity resulted in much faster deamination of 1-aminoindane and 1-aminotetralin than of the corresponding 2-amino compounds, especially in rats. 3. When 1-aminoindane and 1-aminotetralin were incubated with rat liver microsomes and NADPH under 18O2, oxygen-18 was incorporated into the deaminated products, 1-indanone and 1-tetralone. The carbinolamine is a key intermediate in the oxidative deamination by rat liver microsomes, indicating the contribution of cytochrome P-450-dependent alpha-C-oxidation to the reaction. 4. Alicyclic primary amines gave type II binding spectra with rat and rabbit liver microsomes, but the spectra appeared to contain type I components. 5. The ratios of the alcohols, cyclohexanol, 2-tetralol and 2-indanol in the deaminated products were high in both rats and rabbits. The ketones were precursors of the alcohols, and substrate selectivity in reduction of the alicyclic ketones with NADPH was similar in both species.

Amines↗
PubMed1981

Neurotoxic metabolites of "commercial hexane" in the urine of shoe factory workers.

Urinary metabolites were tested in 41 shoe-factory workers exposed to a mixture of 10 solvents among which "commercial hexane" was the prevailing component. Cyclohexanol, 2-methyl-2-pentanol, 3-methyl-2-pentanol, and trichloroethanol were determined in connection with exposure to cyclohexane, 2-methylpentane, 3-methylpentane, and trichloroethylene, respectively. 2-Hexanol, 2,5-hexanedione, 2,5-dimethylfuran, and gamma-valerolactone were all determined in connection with n-hexane exposure only. 2,5-Hexanedione was the principal n-hexane metabolite found in the workers' urine. This finding of the experimentally proven neurotoxin 2,5-hexanedione in the urine of shoe-factory workers exposed to "commercial hexane" is consistent with the idea that this compound is responsible for the development of neuropathy in this group of individuals.

Air Pollutants↗
PubMed1981

Aminoglycosides. V. Synthesis of glucopyranoside derivatives of neamine modified in the 2-deoxystreptamine ring.

trans-4-Aminocyclohexanol-2'-amino-alpha-D-glucopyranosides were prepared which are derivatives of neamine having the 3-amino and 5 and 6 hydroxyl groups of the 2-deoxystreptamine ring replaced with hydrogen. The 2'-amino-alpha-glycosides were synthesized by the method of LEMIEUX using a chloro nitroso dimer of a glucal and appropriately substituted cyclohexanols. Reductive deblocking of the intermediate 2-oximino derivatives afforded paromamine and neamine analogues. Two examples of 2'-amino-alpha-glycosides with ring-opened variations of the 2-deoxystreptamine aglycone are described. None of the compounds exhibited better in vitro antibacterial activity than neamine when compared against Gram-positive and Gram-negative bacteria.

Bacteria↗
PubMed1976

[Effect of nicotinic acid derivatives on the cholesterol metabolism with special regard to biosynthesis, absorption and excretion of cholesterol in the salivary gland (author's transl)].

The cholesterol metabolism of the salivary gland of mice fed on a diet containing 0.5% nicotinic acid derivative, 2, 2, 6, 6, tetrakis--(nicotinoyl-oxymethyl)--cyclohexanol (K-31) was as follows. 1. Total cholesterol level of sublingual and submaxially glands decreased in mice fed on normal diet as well as cholesterol-added diet. 2. The in vivo cholesterol biosynthesis from the acetate-1-14C increased in the sublingual gland, while it was not affected in the submaxillary gland. However, in vitro cholesterol synthesis decreased in both sublingual and submaxillary glands. 3. The disappearance of cholesterol-4-14C injected into the mice was more rapid in the K-31 treated mice than in the control after 30 days. 4. The incorporation of cholesterol-7-3h with a constant specific radioactivity administered orally for 37 days was reduced in the sublingual and submaxillary glands of K-31 treated mice. 5. When the mice were maintained on cholesterol-added diet for 21 days after cholesterol-4-14C injection, the excretion of sterol-14C in the feces was increased in K-31 treated mice. Thus, it was considered that the decrease of the cholesterol level of salivary glands by oral administration of K-31 is due to the increase of the excretion of cholesterol, the decrease of the uptake of the external cholesterol and the increase of excretion of sterol in the feces. These alterations of the cholesterol metabolism appear to induce cholesterol biosynthesis.

Animals↗
PubMed2004

Volatile organic compound (VOC) analysis and sources of limonene, cyclohexanone and straight chain aldehydes in axenic cultures of Calothrix and Plectonema.

The volatile organic compounds (VOCs) in four standing cultures of axenic benthic cyanobacteria (Calothrix and Plectonema) were studied by GC/MS analysis. To verify the biogenic origin of the VOCs, 13C-labelling experiments were performed, and the differences in labelling were used to differentiate between biogenic and non-biogenic sources. Strongly labelled biogenic compounds were derived from the shikimate (cresol, skatole), isoprenoid (beta-cyclocitral, beta-ionone, geosmin) and fatty acid pathways (5Z-heptadecene, 3-octanone, 1-hexanol). New odour compounds derived from microorgansims were beta-cyclogeraniol, dihydro-beta-ionone and 2-hydroxy-2,6,6-trimethylcyclohexanone. The latter compound had already been found in lake water, but could not be assigned to a particular organism. Straight chain aldehydes (octanal, nonanal, decanal), cyclohexanone, cyclohexanol and limonene were unlabelled beyond their natural isotope ratio. Therefore, the biogenic origin of these compounds is doubtful despite their occurrence in axenic cultures. The observation that limonene was a racemate supports this view. The precursors and reactions that lead to the formation of these non-biogenic compounds are unknown and it may be that they are formed by the analytical procedures rather than then being present in the culture medium.

Aldehydes↗
PubMed1997

[The synthesize of mono-( 6-S-DNS )- beta-CD and its molecular recognition ability].

Mono- ( (6-S-DNS) - beta -CD is synthesized and characterized. The interaction between the luminescent derivative of beta-cyclodextrin and guest (cyclohexanol, cyclohexene, Bromocyclohexane, and p-phthalic acid, m-phthalic acid 3, 5-Dinitrobenzoic acid, p-hydroxybenzoic acid, p-animobenzoic acid)has been slutied. The binding constants and sensitivety factors are obtained based on modified Hildbrand-Benesi equation. The results show that the guest-Host inclusion complex with 1:1 stoichiometry is formed and that the binding constants and sensitivity factors for molecular recognition is directly related to the molecular structure and hydrophobic character of guest.

Hydrophobic and Hydrophilic Interactions↗
PubMed1998

[Synthesis and molecular recognition study of 6-Cs-beta-CD].

The reagents 6-Cs-beta-CD with molecular recognition function were synthesized and confirmed. Both basic condition and enough illumination were necessary for obtaining stable and strong fluorescence. With 6-Cs-beta-CD as the host, cyclohexanol, cyclohexene, cyclohexane and bromocyclohexane as the guest, the recognition properties were studied. The affinity of 6-Cs-beta-CD and the guest is distinct with different hydrophobicity of the guest.

Hydrophobic and Hydrophilic Interactions↗
PubMed2005

[Recent evidences in the pharmacological mechanisms of the tramadol].

Tramadol [(1R, 2R) and (1S, 2S)-2-dimethyl-amino-methyl-1-(3-methoxyphenyl) -cyclohexanol hydrochloride] has been used clinically. It binds to micro-opioid receptors with lower affinity than morphine, which suggests that the antinociceptive action of tramadol may not be due to opioid receptor binding. Several lines of evidence have shown that tramadol inhibits the reuptake of monoamines, as do antidepressant drugs such as desipramine. Tramadol inhibits the reuptake of NE and serotonin. The mechanisms of action of tramadol have not been well understood. Recently, some evidences in the mechanisms of action of tramadol have been published. Tramadol inhibits the muscarinic receptor, serotonin receptor, and nicotinic acetylcholine receptor ion-channel, suggesting these receptors might be related to the mechanisms of action of tramadol. In this review, the mechanisms of action of tramadol were reviewed form these findings. Tramadol does not alter renal blood flow (RBF) in normal rats. This suggests that tramadol would be a safe analgesic maintaining RBF during the postoperative period. It would be necessary to study the effects of tramadol on orphan G-ptotein coupled receptor which is related to the pain.

Analgesics, Opioid↗