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PubMed2005

Cytotoxic constituents of the octocoral Dendronephthya gigantea.

A known monoalkyl glycerol ether, (+/-)-1-nonadecyloxy-2,3-propanediol (1) was isolated from the ethyl acetate extract of a soft coral Dendronephthya gigantea as a weakly cytotoxic constituent against four human cancer cell lines, A549, HT-29, HT-1080, and SNU-638. In addition, a known ceramide, (2S,3R,4E,8E)-N-hexadecanoyl-2-amino-4,8-octadecadiene-1,3-diol (2), was also isolated as an inactive constituent. This is the first report on the isolation of the compounds 1 and 2 from the octocoral, Dendronephthya species.

Alkadienes↗

PubMedDate not supplied

Identification and determination of urinary metabolites of 2-isopropylnaphthalene in rabbits.

Four unconjugated metabolites, which were produced through the oxidation of the isopropyl chain of 2-isopropylnaphthalene (2-IPN), were isolated from the urine of rabbits receiving 2-IPN orally and identified: 2-(2-naphthyl)propionic acid, 2-(2-naphthyl)-2-propanol, 2-(2-naphthyl)-1,2-propanediol, and 2-(2-naphthyl)-2-hydroxypropionic acid, together with a small amount of the unchanged compound. Further, the unconjugated metabolites, which were produced through the oxidation of the naphthalene ring, were isolated and identified: 2-isopropylnaphthols and 2-isopropyl-5,6 (or 7,8)-dihydronaphthalene-5,6 (or 7,8)-diol. The identification of these metabolites was made by means of TLC, GLC, MS, IR, GC/MS, and FT-NMR. The presence of glucuronides of metabolites B, C, D, F, and H was also suggested by TLC and GLC of the extract obtained after hydrolysis by beta-glucuronidase. In addition, quantitative determination of the metabolites indicated that the total urinary excretion of the metabolites except 2-isopropylnaphthols in 24 hr after administration was about 29% of the dose.

Administration, Oral↗

PubMed2007

Photo-induced cold vapor generation with low molecular weight alcohol, aldehyde, or carboxylic acid for atomic fluorescence spectrometric determination of mercury.

With UV irradiation, Hg(2+) in aqueous solution can be converted into Hg(0) cold vapor by low molecular weight alcohols, aldehydes, or carboxylic acids, e.g., methanol, formaldehyde, acetaldehyde, glycol, 1,2-propanediol, glycerol, acetic acid, oxalic acid, or malonic acid. It was found that the presence of nano-TiO(2) more or less improved the efficiency of the photo-induced chemical/cold vapor generation (photo-CVG) with most of the organic reductants. The nano-TiO(2)-enhanced photo-CVG systems can be coupled to various analytical atomic spectrometric techniques for the determination of ultratrace mercury. In this work, we evaluated the application of this method to the atomic fluorescence spectrometric (AFS) determination of mercury in cold vapor mode. Under the optimized experimental conditions, the instrumental limits of detection (based on three times the standard deviation of 11 measurements of a blank solution) were around 0.02-0.04 microg L(-1), with linear dynamic ranges up to 15 microg L(-1). The interference of transition metals and the mechanism of the photo-CVG are briefly discussed. Real sample analysis using the photo-CVG-AFS method revealed that it was promising for water and geological analysis of ultralow levels of mercury.

Alcohols↗

PubMed2002

Effect of glucose on glycerol bioconversion by Lactobacillus reuteri.

The impact of glucose on glycerol metabolism, especially on 3-hydroxypropionaldehyde (3-HPA) accumulation by resting cells of Lactobacillus reuteri has been investigated. Two systems were used in the study: MRS(-) (modified MRS - omitting glucose, acetate and Tween 80) and distilled water (H(2)O). In MRS(-), addition of glucose enhanced glycerol metabolism in resting cells of L. reuteri, consequently increasing the accumulation of 3-HPA by regulating the NAD/NADH ratio. Enhanced glycerol metabolism correlated positively with the concentration of glucose. NADH produced during glucose metabolism was preferentially reoxidized to NAD by the reduction of 3-HPA to 1,3-propanediol; an adequate supply of glycerol therefore outweighed the repression of glucose on the accumulation of 3-HPA. At a molar ratio of glucose to glycerol no greater than 0.33, accumulation of 3-HPA was favored. In non-growing medium (H(2)O), addition of glucose seemed to be counter-productive with respect to 3-HPA accumulation. Lactate had a positive impact on glycerol metabolism, presumably by altering the redox flux, resulting in enhanced 3-HPA accumulation in both MRS(-) and H(2)O systems.

Aldehydes↗

PubMed2003

3-hydroxypropionaldehyde: applications and perspectives of biotechnological production.

3-hydroxypropionaldehyde (3-HPA) forms, together with HPA-hydrate and HPA-dimer, a dynamic, multi-component system (HPA system) used in food preservation, as a precursor for many modern chemicals such as acrolein, acrylic acid, and 1,3-propanediol (1,3-PDO), and for polymer production. 3-HPA can be obtained both through traditional chemistry and bacterial fermentation. To date, 3-HPA has been produced from petrochemical resources as an intermediate in 1,3-PDO production. In vivo, glycerol is converted in one enzymatic step into 3-HPA. The 3-HPA-producing Lactobacillus reuteri is used as a probiotic in the health care of humans and animals. The biotechnological production of 3-HPA from renewable resources is desirable both for use of 3-HPA in foods and for the production of bulk chemicals. The main challenge will be the efficient production and recovery of pure 3-HPA.

Acrolein↗

PubMed2005

Isolation and characterization of a new Mycobacterium austroafricanum strain, IFP 2015, growing on MTBE.

A new Mycobacterium austroafricanum strain, IFP 2015, growing on methyl tert-butyl ether (MTBE) as a sole carbon source was isolated from an MTBE-degrading microcosm inoculated with drain water of an MTBE-supplemented gasoline storage tank. M. austroafricanum IFP 2015 was able to grow on tert-butyl formate, tert-butyl alcohol (TBA) and alpha-hydroxyisobutyrate. 2-Methyl-1,2-propanediol was identified as the TBA oxidation product in M. austroafricanum IFP 2015 and in the previously isolated M. austroafricanum IFP 2012. M. austroafricanum IFP 2015 also degraded ethyl tert-butyl ether more rapidly than M. austroafricanum IFP 2012. Specific primers designed to monitor the presence of M. austroafricanum strains could be used as molecular tools to detect similar strains in MTBE-contaminated environment.

Bacterial Proteins↗

PubMed2025

Structural properties of short-chain carboxylic acids and alcohols relate to the molecular and physiological response of Salmonella enterica in an acidic environment.

Short-chain carboxylic acids (SCCA) and short-chain alcohols (SCALC) are naturally occurring antimicrobials that contribute to the biopreservation of food fermentations. This study investigated the effect of structurally different SCCA/SCALC with two-carbon (acetic acid; phenylacetic acid; 2-phenylethanol), three-carbon (propionic acid; 3-phenylpropionic acid; 3-phenylpropanol), and three-carbon chain with an additional hydroxyl group (lactic acid; 3-phenyllactic acid; 1-phenylpropanol) on the fitness, metabolic activity and gene expression of the pathogen Salmonella enterica at pH 4.5. SCCA inhibited Salmonella at lower concentrations than SCALC with the exception of lactic acid, which was partly consumed. The presence of a phenyl group enhanced antimicrobial activity. SCCA but not SCALC increased the lag phase of S. enterica, and in general, acetate was formed when cell growth was reduced by 20% suggesting a negative impact on bacteria fitness. Principal component analysis and hierarchical clustering indicated distinct gene expression profiles of S. enterica in response to SCCA or SCALC. In the presence of certain SCCA/SCALC, Salmonella activated pathways related to cellular pH control, and 1,2-propanediol, propionic acid and ethanolamine metabolism that involved the formation of metabolosomes. Genes related to flagellar assembly were less expressed and mobility was lower in the presence of lactic and 3-phenyllactic acid compared to controls suggesting a compound-specific response. KEY POINTS: • Differences in response among structurally different SCCA/SCALC at acidic condition. • SCCA/SCALC stress interfered with cell growth and metabolism of acetic and propionic acid. • Lactic acid prolonged the lag phase and reduced motility of Salmonella.

Salmonella enterica↗

PubMed2001

Influence of glucose on glycerol metabolism by wild-type and mutant strains of Clostridium butyricum E5 grown in chemostat culture.

In order to improve the yield of 1,3-propanediol (1,3-PPD) in Clostridium butyricum E5, we carried out cofermentation experiments on glucose/glycerol mixtures in chemostat culture. The results showed the influence of the ratio of the two carbon substrates on the production of the required diol. The progressive increase of glucose in culture medium containing a given concentration of glycerol made it possible to highlight the deviation of carbon flow from the oxidative towards the reducing pathway, in order to maintain the oxidation/reduction balance in the cell. The conversion of glycerol into 1,3-PPD thus increased from 0.63 mol mol(-1), without the addition of glucose, to a maximum of 0.89 mol mol(-1) for a molar glucose/glycerol ratio of 0.2 for the wild-type strain. The same experiments carried out with the mutant MD strain, which is resistant to allyl alcohol, led to similar results but with a maximum of 0.84 mol mol(-1) for a glucose/glycerol molar ratio of 0.1. Beyond a molar ratio of 0.2, the biosynthesis of enzymes for the glycerol metabolism was less subject to catabolic repression by glucose in the mutant MD strain than in the wild-type strain.

Alcohol Dehydrogenase↗

PubMed1999

Chemicals from biotechnology: molecular plant genetics will challenge the chemical and the fermentation industry.

Industrial biotechnology has evolved as a significant manufacturing tool for products like fuel-grade ethanol, organic acids and bulk amino acids, but most items are still speciality products for food and pharmaceutical applications. Current development projects within the chemical industry, including lactic acid and 1,3-propanediol based polymers and plastics, indicate that new biotechnological processes and products may soon approach the market place, clearly targeted at the leading petrochemical bulk outlets. This is flanked by a strategic shift by the major chemical companies in to "life sciences"-pharmaceuticals, agrochemicals and the seed business as well as biotech fine chemicals. The recent tremendous achievements in molecular plant genetics and transgenic crop breeding will boost agrobiotechnology, agriculture and renewable raw materials as compelling projects for chemistry and biotechnology. New plant-based production routes may challenge established chemical and biochemical domains, but at the same time open new horizons to valuable feedstocks, intermediates and end-products.

Biotechnology↗

PubMed1997

A novel proline-rich glycoprotein associated with the extracellular matrix of vascular bundles of Brassica petioles.

A panel of monoclonal antibodies (MAC204, MAC236, MAC265) which recognise extracellular matrix glycoproteins implicated in plant-microbe interactions has been used to study glycoprotein antigens in petioles of turnip (Brassica campestris L.). While MAC204 recognised two glycoproteins (gp120 and gp45) with apparent M(r) 120,000 and 45,000 in petiole extracts made with 2-amino-2-(hydroxymethyl)-1,3-propanediol (Tris) buffer containing sodium dodecyl sulfate, MAC236 recognised gp120 but not gp45, and MAC265 gave no or only weak reactivity. Tissue dissection studies established that gp120 was predominantly associated with the vascular bundle whereas gp45 was largely associated with the pith. This was consistent with results from tissue prints probed with MAC204 and MAC236 which also suggested a vascular localisation for gp120. Immunoelectronmicroscopy showed that MAC204 and MAC236 both labelled three-way junctions between cells of the phloem and sclerid fibres. Both gp120 and gp45 were shown to carry epitopes in common with known hydroxyproline-rich glycoproteins. Unlike gp45, gp120 could be extracted from petioles with Tris buffer alone and then isolated from this extract by trichloroacetic acid treatment (which left gp120 soluble), followed by size-exclusion and ion-exchange chromatography. Amino acid analysis revealed gp120 to be a novel glycoprotein, particularly rich in proline, lysine, valine and threonine but relatively poor in hydroxyproline. The most abundant sugars were arabinose and galactose. The potential role of this very basic cell surface glycoprotein in plant defence against microbes is discussed.

Antibodies, Monoclonal↗

PubMed2000

Low propensity of conventional antiepileptic drugs for interaction with felbamate against maximal electroshock-induced seizures in mice.

The objective of this study was to evaluate an interaction of the novel antiepileptic drug felbamate (2-phenyl-1,3-propanediol dicarbamate) with conventional antiepileptic drugs against maximal electroshock-induced convulsions in mice. Electroconvulsions were produced by means of an alternating current (ear-clip electrodes, 0.2-s stimulus duration, tonic hindlimb extension taken as the endpoint). Adverse effects were evaluated in the chimney test (motor performance) and passive avoidance task (long-term memory). Brain and plasma levels of antiepileptic drugs were measured by immunofluorescence. Felbamate (7.5-30 mg/kg) significantly increased the electroconvulsive threshold. Felbamate at the subprotective dose of 5 mg/kg did not affect the anticonvulsive action of antiepileptics studied. On the other hand, this drug used at the lowest protective dose of 7.5mg/kg remained without effect upon the activity of valproate, carbamazepine or phenobarbital, but significantly potentiated the protective potential of diphenylhydantoin. No adverse effects were observed with combinations of felbamate with these antiepileptics. Neither brain nor free plasma levels of antiepileptic drugs were changed by felbamate. The results indicate that the combination of felbamate with conventional antiepileptic drugs is not promising from the experimental point of view.

Animals↗

PubMed2006

Cryopreservation of human ovarian tissue.

New and often aggressive treatment schemes allow the successful healing of many young patients with cancer, but the price the young women have to pay is high: many of them lose ovarian function and fertility. Due to the improved long-term survival of adolescents and young women with malignancies undergoing gonadotoxic chemotherapy, preservation of future fertility has been the focus of recent ubiquitarian interest. A feasible solution is the cryopreservation of ovarian tissue. Ovarian tissue, after thawing, can be used in three different ways: 1. grafted into its normal site (orthotopic); 2. grafted into a site other than its normal position (heterotopic), necessitating recourse to in vitro fertilization (IVF); 3. grown and in vitro matured in order to obtain metaphase II oocytes for an IVF program. It is believed that protein supplementation, in cryopreservation solution, is essential for improving ovarian tissue cryopreservation. The aim of this study was to evaluate the ultrastructural appearance of human ovarian tissue cryopreserved in 1.5 M 1,2 propanediol (PROH), 0.2 M sucrose using different protein sources: fetal calf serum (FCS), plasmanate or syntetic serum substitute (SSS). Fresh and frozen/thawed ovarian tissues were compared by transmission electron microscope (TEM), to evaluate the appearance of stromal and follicle cells as affected by different protein sources. Our data indicate that FCS is a better protein support for ovarian tissue cryopreservation when compared to SSS or Plasmanate. In addition the follicles are more resistant to the cryopreservation with respect to stroma.

Adolescent↗

PubMed2006

Influence of freezing and low molecular weight cryoprotectants on microsomal membrane structure: a study by multiparametric fluorescent probe.

The influence of low molecular weight cryoprotectants (CPs) such as glycerol (GL), 1,2-propanediol (PD) and dimethylsulfoxide (DMSO) on the structure of rat liver microsomal membranes on the stages of equilibration and upon freezing up to -196 degrees C was studied using a multiparametric fluorescent probe of flavonol nature. It was estimated that the studied CPs have individual concentration ranges defining low amplitude of their action on biomembranes. An exceeding of these ranges strongly increases the violation of membrane native structure already at the stage of incubation with CPs, strengthening it during the freezing procedure. According to the perturbation effect on microsomal membranes the studied CPs can be arranged in a sequence: DMSO>PD>GL.

Animals↗

PubMed2006

Reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of bidentate nucleophiles.

The reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of 1,2-ethanediol leads to N (1)-(alkyl)-2-(5,7-dioxo-1,4-dioxepane-6-yl)-2-methylpropanamides. 1,3-Propanediol or 1,4-butanediol produce hydroxyalkyl 1-(tert-butyl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxylates. When the reaction was performed in the presence of catechol, bis(2-hydroxyphenyl) 2-[2-(tert-butylamino)-1,1-dimethyl-2-oxoethyl]malonate was obtained. 2-Aminophenols react with alkyl isocyanides in the presence of isopropylidene Meldrum's acid to produce 1-alkyl-N (3)-(2-hydroxyaryl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxamides in good yields.

Amides↗

PubMed2026

Integrated ¹H-NMR Metabolomics and Growth Kinetics Uncover Three Distinct Metabolic Scenarios in Lactiplantibacillus pentosus P7 Fermentation of Plant-Derived Prebiotics.

Lactic acid bacteria (LAB) drive a broad range of food and biotechnological fermentations, the outcomes of which depend not only on the bacterial genotype but also on the chemical composition of the fermentation substrate. To resolve how a single strain reorganises chemically distinct plant matrices, we profiled fermentations of Lactiplantibacillus pentosus P7 (GenBank JBLMKZ000000000) on garlic, onion, and kiwifruit extracts prepared in water and 70% ethanol, using growth kinetics combined with solvent-suppressed 500-MHz proton nuclear magnetic resonance metabolomics over 48 h, and integrated the data with whole-genome pathway annotations. Three substrate-specific metabolic scenarios emerged. On garlic, P7 grew vigorously, with the water extract exceeding the de Man-Rogosa-Sharpe reference medium at every time point (peak ΔOD₆₀₀ of 9.38 versus 8.52 at 24 h) and accumulating sorbose, rhamnose, and the aromatic amino acids phenylalanine and tryptophan (3.04- to 3.70-fold increases), providing first metabolic evidence consistent with the strain's four-copy aroE shikimate-dehydrogenase expansion. On onion, the lowest cell density coincided with the highest lactate output of the dataset (5.21-fold rise at 48 h), transient 5-hydroxymethylfurfural reduction, and accumulation of acetoin and 1,3-propanediol, mapping onto a redundant set of pyridine-nucleotide-dependent oxidoreductases and a pdu-independent diol pathway. On kiwifruit, citrate accumulated 8.9-fold at 16 h and then declined, consistent with an intact citCDEFG citrate-lyase operon paired with absence of canonical oxidative tricarboxylic acid enzymes. The optimal extraction solvent was substrate-dependent, water for garlic and ethanol for onion and kiwifruit. Overall, these results show that substrate chemistry, rather than strain identity, dictates which genome-encoded pathways P7 engages, establishing P7 as a versatile, substrate-tunable platform for the functional fermentation and biorefining of furanic-rich substrate streams. Raw NMR data and ISA-Tab metadata are available via MetaboLights with identifier MTBLS14463.

Lactiplantibacillus pentosus↗

PubMed1983

Separation of hemoglobin types by cation-exchange high-performance liquid chromatography.

The use of a recently developed cation-exchange HPLC packing material for the separation of hemoglobin types in human blood has been investigated. Adult and newborn hemolysates from normal individuals and from subjects with hemoglobin disorders were analyzed using a weak cation carboxymethyl-bonded phase on 5-micron-particle-size silica. Elution was accomplished using a Bistris (2-[bis(2-hydroxyethyl)amino]-2-(hydroxymethyl)-1, 3-propanediol) gradient. Seven well-resolved HbA1 fractions eluted before the major HbA peak. Hbs A1a, A1b, A1c and an HbA1 fraction that increased with aging of the hemolysates were separately eluted. HbF when present or when added to the hemolysates eluted as a distinct peak. HbA was followed by Hbs A2, S, and C when present. An early-eluting peak corresponding to Hb Bart's was identified in newborn hemolysates. It is concluded that cation-exchange HPLC provides a new tool for the reliable separation of minor hemoglobin components.

Adult↗

PubMed1983

Purification of reduced nicotinamide adenine dinucleotide by ion-exchange and high-performance liquid chromatography.

Combining ion-exchange (AG MP-1) and reversed-phase (C-18) partition chromatography accomplishes a higher degree of purification of NADH than either method can provide alone. Final elution in 95% ethanol, dehydration with anhydrous sodium sulfate, and storage in dry 1,2-propanediol over molecular sieves prevents hydrolysis of the purified dinucleotide.

Chromatography, High Pressure Liquid↗

PubMed1985

Measurement of acetol in serum.

A method for the derivatization of acetol (1-hydroxyacetone) with 2,4-dinitrophenylhydrazine (DNPH) and for the measurement of the acetol dinitrophenylhydrazone derivative (acetol-DNPH) by high-performance liquid chromatography is presented. The chromatographic separation described here resulted in baseline resolution of the acetol-DNPH peak. Peak integration was proportional to serum acetol concentration over a 5- to 500-nmol/ml range. No other method for the determination of acetol in serum currently exists. Serum from rats in diabetic ketoacidosis was found to contain 11.2 +/- 1.1 nmol acetol/ml serum (N = 3). Serum from a 21-day-fasted human contained 16 nmol/ml acetol. Serum from rats maintained on drinking water containing 1% acetone (v:v) for 6 days contained 152 +/- 31 nmol/ml acetol (N = 5). The presence of acetol in serum under conditions where acetoacetate and acetone are chronically elevated suggests that acetoacetate may be converted to glucose through the conversion of acetone to acetol and L-1,2-propanediol.

Acetone↗