Lipidomics as an important key for the identification of beer-spoilage bacteria.

Electrospray ionization-tandem mass spectrometry (ESI-MS/MS) was used for characterizing intact plasmalogen phospholipid molecules in beer-spoilage bacteria. Identification of intact plasmalogens was carried out using collision-induced dissociation and the presence of suitable marker molecular species, both qualitative and quantitative, was determined in samples containing the anaerobic bacteria Megasphaera and Pectinatus. Using selected ion monitoring (SIM), this method had a limit of detection at 1 pg for the standard, i.e. 1-(1Z-octadecenyl)-2-oleoyl-sn-glycero-3-phosphoethanolamine and be linear in the range of four orders of magnitude from 2 pg to 20 ng. This technique was applied to intact plasmalogen extracts from the samples of contaminated and uncontaminated beer without derivatization and resulted in the identification of contamination of beer by Megasphaera and Pectinatus bacteria. The limit of detection was about 830 cells of anaerobic bacteria, i.e. bacteria containing natural cyclopropane plasmalogenes (c-p-19:0/15:0), which is the majority plasmalogen located in both Megasphaera and Pectinatus. The SIM ESI-MS method has been shown to be useful for the analysis of low concentration of plasmalogens in all biological samples, which were contaminated with anaerobic bacteria, e.g. juice, not only in beer. Significance and impact of the study: Electrospray ionization-tandem mass spectrometry (ESI-MS/MS) using collision-induced dissociation was used to characterize intact plasmalogen phospholipid molecules in beer-spoilage anaerobic bacteria Megasphaera and Pectinatus. Using selected ion monitoring (SIM), this method has a detection limit of 1 pg for the standard 1-(1Z-octadecenyl)-2-oleoyl-sn-glycero-3-phosphoethanolamine and is linear within four orders of magnitude (2 pg to 20 ng). The limit of detection was about 830 cells of bacteria containing natural cyclopropane plasmalogen (c-p-19:0/15:0). SIM ESI-MS method is useful for analyzing low concentrations of plasmalogens in biological samples contaminated with anaerobic bacteria, e.g. beer or juice.

Protective effect of Clostridium tyrobutyricum in acute dextran sodium sulphate-induced colitis: differential regulation of tumour necrosis factor-α and interleukin-18 in BALB/c and severe combined immunodeficiency mice.

One of the promising approaches in the therapy of ulcerative colitis is administration of butyrate, an energy source for colonocytes, into the lumen of the colon. This study investigates the effect of butyrate producing bacterium Clostridium tyrobutyricum on dextran sodium sulphate (DSS)-induced colitis in mice. Immunocompetent BALB/c and immunodeficient severe combined immunodeficiency (SCID) mice reared in specific-pathogen-free (SPF) conditions were treated intrarectally with C. tyrobutyricum 1 week prior to the induction of DSS colitis and during oral DSS treatment. Administration of DSS without C. tyrobutyricum treatment led to an appearance of clinical symptoms - bleeding, rectal prolapses and colitis-induced increase in the antigen CD11b, a marker of infiltrating inflammatory cells in the lamina propria. The severity of colitis was similar in BALB/c and SCID mice as judged by the histological damage score and colon shortening after 7 days of DSS treatment. Both strains of mice also showed a similar reduction in tight junction (TJ) protein zonula occludens (ZO)-1 expression and of MUC-2 mucin depression. Highly elevated levels of cytokine tumour necrosis factor (TNF)-α in the colon of SCID mice and of interleukin (IL)-18 in BALB/c mice were observed. Intrarectal administration of C. tyrobutyricum prevented appearance of clinical symptoms of DSS-colitis, restored normal MUC-2 production, unaltered expression of TJ protein ZO-1 and decreased levels of TNF-α and IL-18 in the descending colon of SCID and BALB/c mice, respectively. Some of these features can be ascribed to the increased production of butyrate in the lumen of the colon and its role in protection of barrier functions and regulation of IL-18 expression.

Structural analysis of a polysaccharide from Chlorella kessleri by means of gas chromatography-mass spectrometry of its saccharide alditols.

Interpretation of gas chromatographic-mass spectrometric data of oligosaccharide alditols was used to determine their structures and to derive the structure of a water soluble polysaccharide isolated from Chlorella kessleri. 1H- and 13C-NMR was employed to assess the configuration of glycosidic bonds and individual monosaccharides were assigned to the L or D series by means of gas chromatography of the acetylated (S)-2-butyl glycosides.

Relationship between volatile odorous substances and production of avermectins by Streptomyces avermitilis.

The time course of production of odorous compounds, i.e. geosmin and oxolones, and of avermectins was determined during the cultivation of S. avermitilis in flasks, 1- and 50-L fermentors. The amount of the antibiotics increased with increasing cultivation time up to more than 2 g/L while the concentration of geosmin rose to more than 4 mg/L. Cultivation without reflux condenser resulted in a lower product formation due to the higher stripping of geosmin. A relatively tight correlation was found between the production of geosmin and the production of avermectins. The production of oxolones peaked on cultivation days 3-5, the sum of oxolones being 60 microg/L. Subsequently, the production dropped below a measurable level. This can be explained as being due to the inhibition of oxolone production by geosmin.

Adaptive changes in fatty acids of E. coli strains exposed to a quaternary ammonium salt and an amine oxide.

Resistant strains of Escherichia coli were obtained by stepwise cultivation in media with increasing concentration of antimicrobially active 1-(methyldodecyl)dimethylamine oxide and 1-(methyldodecyl)trimethylammonium bromide. Adaptive changes were determined in the fatty-acid (FA) composition in an isolated lipopolysaccharide sample from the outer membrane of these strains. The composition of this FA mixture from adapted strains was compared with that of FA from a sensitive strain. The differences were found in level of palmitic, heptadecanoic, heptadecenoic, heptadecadienoic and nonadecenoic acids. In addition, the adapted strains differed from each other in the content of myristic, pentadecanoic, stearic and linoleic acids.

Metabolites produced by cyanobacteria belonging to several species of the family Nostocaceae.

This paper provides a comprehensive overview of metabolites, including lipids and lipid-like compounds, nitrogen metabolites, oligopeptides and amino acid derivatives, produced by cyanobacteria of the genera Anabaenopsis, Aphanizomenon, Aulosira, Cylindrospermopsis, Cylindrospermum, Nodularia, and Richelia of the family Nostocaceae.

Use of the industrial yeast Candida utilis for cadmium sorption.

The sorption ability of Candida utilis biomass for cadmium ions with accumulating competence of dried cells and cells in alginate was compared. After an optimization of process conditions (pH 5.5, biomass concentration 1 g/L and c0 50 mg/L), the cadmium sorption capacity of dried yeast biomass was perceptibly higher than that of the other tested adsorbents. Considering the sorption of the dried yeast biomass equal to 100 %, the cells in alginate reached 86 % while native cells showed only 42 %.

Biogenesis of antibiotics-viewing its history and glimpses of the future.

This review aims at comparing some historical data with the current situation in the study of biogenesis of natural compounds, antibiotics in the first place. Biogenesis of tetracyclines and cycloheximide and related compounds serves as example. Examples of molecular biological and bioinformatics methods used in the study of antibiotic biogenesis are described both in terms of its historical aspects and the current knowledge.

Metabolites produced by nitrogen-fixing Nostoc species.

This paper provides a comprehensive overview of metabolites, including lipids and lipid-like compounds, boron-containing macrocycles, arsenolipids, oligopeptides and amino acid derivatives, produced by cyanobacteria of the genus Nostoc.

Removal of copper ions from dilute solutions by Streptomyces noursei mycelium. Comparison with yeast biomass.

Sorption properties of Streptomyces noursei mycelium for copper ions were compared with the accumulation competence of dried and native yeast (Candida utilis) biomass. The copper sorption capacity of S. noursei after optimization was found to be higher than that of the two other adsorbents (dried yeast biomass 82 %, native Candida cells 48 % of the sorption capacity of the S. noursei mycelium).

Influence of inhibitors of lipid biosynthesis on the production of avermectins in Streptomyces avermitilis.

Streptomyces avermitilis was grown in the presence of four inhibitors of fatty acid biosynthesis (p-chlorophenoxyacetic, DL-2-(p-chlorophenoxy)-propionic, 2-(p-chlorophenoxy)-2-methyl-propionic and p-fluorophenoxyacetic acids). The production of total lipids was inhibited and the cellular content of individual types of fatty acids was altered by these compounds. The anteiso-acid content decreased by up to one-half, whereas the content of iso-odd acids increased 10-fold in the presence of inhibitors. The decrease in anteiso-acids was accompanied by increased production of avermectins having a s-butyl group in the side chain (type 'a' avermectins). It was concluded that the common precursor, 2-methylbutyryl-CoA, was diverted from the biosynthetic pathway of fatty acids to that of avermectins.

Isobutyrate as a precursor of n-butyrate in the biosynthesis of tylosine and fatty acids.

Labelled sodium isobutyrate [(CD3)2-CHCOONa] was added to the culture medium of Streptomyces fradiae and up to 14 atoms of deuterium were found to be incorporated into a molecule of tylosin aglycone (tylactone). This observation is in accordance with the data in the literature. When fatty acids were analyzed, as much as 34% of the isobutyrate incorporated into the cell was formed to be transformed into butyrate that was used for the synthesis of even, straight-chain fatty acids; 57% of the labelled isobutyrate was incorporated into the even isoacids, whereas 9% was degraded to propionate and further used for the synthesis of the odd acids.

Nitrogen regulation of fatty acids and avermectins biosynthesis in Streptomyces avermitilis.

Fatty acid composition was analysed in the producer of avermectins, Streptomyces avermitilis C-18 grown in chemically defined medium with different nitrogen sources. Significant differences in nitrogen regulation of fatty acid biosynthesis were found in this strain in comparison with other streptomycetes studied so far. This finding could be explained at the level of regulation of branched-chain amino acid metabolism.

Novel brominated lipidic compounds from lichens of central Asia.

The composition of novel brominated aliphatic compounds from lichens collected during summer from stones around the lake Issyk-Kul (Central Asia) is described. The compounds, predominantly fatty acid derivatives with unique groups (bromine, cyclopropane, oxirane) and conjugated double and triple bonds, were identified by means of 1H and 13C-NMR, MS, IR and UV spectra.

Macrolactone glycosides of three lichen acids from Acarospora gobiensis, a lichen of Central Asia.

The compounds isolated from the extract of Central Asian lichen (Acarospora gobiensis H. Magn.) comprised three new glycosides having 18-hydroxy-dihydroalloprotolichesterinic, 18-hydroxy-neodihydroprotolichesterinic and 18-hydroxy-dihydroprotolichesterinic acids as aglycones and a di- or trisaccharide moiety linked at C-18 and at the carboxylic group. These compounds, called gobienines A-C, were found to be di- or trisacharides forming a macrolactone with the aglycone. The structures were elucidated by using extensive spectroscopic analysis (1D and 2D NMR, MS, IR and ORD) and chemical and enzymatic methods.

Glycoside esters from lichens of central Asia.

Ten compounds isolated from the extract of the central Asian lichens comprised new glycosides and glycoside esters having 18R-hydroxy-dihydroalloprotolichesterinic, 18S-hydroxy-dihydroprotolichesterinic and 18S-hydroxy-neodihydroprotolichesterinic acids, as the aglycones and a saccharide moiety linked at C-18 and also at C-21 made by glucose, xylose or rhamnose. The structures were elucidated using extensive spectroscopic analysis (1D and 2D NMR, MS, IR, UV and ORD) and by biochemical methods.

Further glucosides of lichens' acids from Central Asian lichens.

Eight compounds isolated from an extract of Central Asian lichens comprised new glucosides having murolic, protoconstipatic and allo-murolic acids as the aglycones and a saccharide moiety linked at C-18 made up of four glucoses. The structures were elucidated using extensive spectroscopic analysis (1D and 2D NMR, MS, IR, UV and CD) and by chemical methods.

Glycosidic compounds of murolic, protoconstipatic and allo-murolic acids from lichens of Central Asia.

Eleven compounds isolated from the extract of the Central Asian lichens comprised eight new glycosides having murolic, protoconstipatic and allo-murolic acids, as the aglycones and a saccharide moiety linked at C-18 made up of one or two sugars (glucose and apiose or rhamnose or xylose or arabinose). The structures were elucidated by using extensive spectroscopic analysis (1D and 2D NMR, MS, IR, UV and CD) and chemical methods.

Polyhalogenated homosesquiterpenic fatty acids from Plocamium cartilagineum.

We describe the composition of novel polyhalogenated homosesquiterpenic acids from the red alga Plocamium collected during summer on Maltese Islands and Corsica. The compounds, predominantly derivatives with unique groups (bromine, chlorine, and diene), were identified by means of 1H and 13C NMR, MS, IR and UV spectra.

Bromoallenic lipid compounds from lichens of central Asia.

The composition of two bromoallenic aliphatic fatty acids obtained from lichens collected around Lake Issyk-Kul (central Asia) is described. These compounds were identified by means of 1H and 13C NMR, MS and IR spectra.