ABSTRACT
It was demonstrated that the fungus Penicillium expansum 2-7, a resident strain of the orbital complex Mir, which became dominating at the end of a long-term space flight, formed biologically active secondary metabolites (antibiotics). Using physicochemical methods, these metabolites were identified as xanthocyllin X and questiomycin A. Time courses of their biosyntheses during growth and development of the producer culture were studied. Addition of zinc to the culture medium affected both the growth of the culture and the biosyntheses of the antibiotics. The concentrations of zinc in the medium, optimum for xanthocyllin X and questiomycin A production, amount to 0.3 and 3.0 mg/l, respectively.
Subject(s)
Anti-Bacterial Agents/metabolism , Butadienes/metabolism , Oxazines/metabolism , Penicillium/metabolism , Phenols/metabolism , Spacecraft , Anti-Bacterial Agents/biosynthesis , Butadienes/chemistry , Culture Media , Oxazines/chemistry , Penicillium/growth & development , Phenols/chemistry , Time Factors , ZincABSTRACT
Secondary metabolites of the three strains of Penicillium aurantiogriseum, isolated from permafrost sediments, were identified. It was found that these fungi synthesized diketopiperazine alkaloids roquefortine and 3,12-dihydroroquefortine. The strain VKM FW-766 synthesized alkaloids in in the course of certain growth-related processes. When the strain was grown on a mineral medium, time courses of roquefortine and 3,12-dihydroroquefortine concentrations were characterized by biphasic curves.
Subject(s)
Alkaloids/biosynthesis , Penicillium/metabolismABSTRACT
1-(2,3,5-Tri-O-acetyl)-beta-D-ribofuranosyl indole, the key compound in the synthesis of glycosides with the bis(indole) aglycone, was obtained for the first time by the indoline-indole method. There were synthesized 3-(1-methylindol-3-yl)-4-(1-glycosylindol-3-yl)furan(or pyrrole)-2,5-diones containing the residue of beta-D-ribofuranose or 2-deoxy-beta-D-ribofuranose and analogous glycosides of indolo[2,3-a]furano(or pyrrolo)[3,4-c]carbazol-5,7-diones, which are structurally relative to the antitumor antibiotic rebeccamycin. Their cytotoxicities toward a number of human tumor cell lines were studied in vitro, and the carbazole N-glycosides were shown to be more active than the bis-(indole) glycosides. At the same time, the ribofuranosides were found to be less active than the corresponding ribopyranosides synthesized previously.
Subject(s)
Aminoglycosides , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Indoles , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antineoplastic Agents/chemical synthesis , Biochemistry/methods , Carbazoles/chemistry , Drug Screening Assays, Antitumor , Furans/chemistry , Furans/pharmacology , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Pyrroles/chemistry , Pyrroles/pharmacology , Structure-Activity Relationship , Tumor Cells, CulturedSubject(s)
Anti-Bacterial Agents/chemistry , Fungi/chemistry , Anti-Bacterial Agents/pharmacology , Bacillus subtilis/drug effects , Bridged Bicyclo Compounds/chemistry , Bridged Bicyclo Compounds/pharmacology , Gram-Negative Bacteria/drug effects , Lactones/chemistry , Lactones/pharmacology , Magnetic Resonance Spectroscopy , Mass Spectrometry , Microbial Sensitivity Tests , Spectrophotometry, Infrared , Spectrophotometry, UltravioletABSTRACT
The study of the secondary metabolites of the relict strain Penicillium citrinum VKM FW-800 isolated from ancient Arctic permafrost sediments showed that this fungus produces agroclavine-1 and epoxyagroclavine-1, which are rare ergot alkaloids with the 5R,10S configuration of the tetracyclic ergoline ring system. The production of the alkaloids by the fungus showed a biphasic behavior, being intense in the phase of active growth and slowing down in the adaptive lag phase and in the stationary growth phase. The addition of zinc ions to the incubation medium led to a fivefold increase in the yield of the alkaloids. The alkaloids-producing Penicillium fungi isolated from different regions exhibited the same tendencies of growth and alkaloid production.
Subject(s)
Ergolines/metabolism , Geologic Sediments/microbiology , Penicillium/metabolism , Arctic Regions , Ergolines/analysis , Penicillium/growth & development , Penicillium/isolation & purificationABSTRACT
The analysis of the absorption spectra of the low-molecular-weight nitrogen-containing secondary metabolites--alkaloids--of 4 Penicillium chrysogenum strains and 6 Penicillium expansum strains isolated on board the Mir space station showed that all these strains synthesize metabolites of alkaloid origin (roquefortine, 3,12-dihydroroquefortine, meleagrin, viridicatin, viridicatol, isorugulosuvin, rugulosuvin B, N-acetyl-tryptamine, and a "yellow metabolite" containing the benzoquinone chromophore).
Subject(s)
Alkaloids/biosynthesis , Indoles , Penicillium chrysogenum/isolation & purification , Penicillium/isolation & purification , Spacecraft , Alkaloids/analysis , Alkaloids/chemistry , Chromatography, Thin Layer , Ergolines/analysis , Ergolines/metabolism , Heterocyclic Compounds, 4 or More Rings , Hydroxyquinolines/analysis , Hydroxyquinolines/metabolism , Molecular Weight , Nitrogen/analysis , Ovomucin/analysis , Ovomucin/biosynthesis , Penicillium/metabolism , Penicillium chrysogenum/metabolism , Piperazines/analysis , Quinolones/analysis , Quinolones/metabolism , Spectrophotometry, Ultraviolet , Tryptamines/analysis , Tryptamines/biosynthesisABSTRACT
Two diketopiperazine alkaloids, rugulosuvines A and B (tryptophan and phenylalanine are precursors), were isolated and purified from the culture liquid of Penicillium rugulosum VKM F-352 and Penicillium piscarium VKM F-325 fungi. Physical and physicochemical studies showed the absolute structure of rugulosuvine A. The absolute structure of rugulosuvine B was demonstrated to be similar to that of rugulosuvine A.
Subject(s)
Alkaloids/chemistry , Penicillium/chemistry , Piperazines/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Drug Screening Assays, Antitumor , Phenylalanine , Piperazines/isolation & purification , Piperazines/pharmacology , Tryptophan , Tumor Cells, CulturedABSTRACT
The type strain Penicillium vitale Pidoplichko et Bilai apud Bilai 1961 VKM F-3624 was found to considerably differ from a sibling species P. janthinellium (syn. P. simplicissimum) in some physiological and morphological features (growth rates at different temperatures, the size of philiades, and the shape of conidia), as well as in the pattern of the nitrogen-containing secondary metabolites produced (roquefortine, 3,12-dihydroroquefortine, meleagrin, aurantioclavine, indole-3-acetic acid, and N-acetyltryptamine). The data obtained suggest that P. vitale represent an independent species.
Subject(s)
Penicillium/classification , Classification , Nitrogen/metabolism , Penicillium/metabolismABSTRACT
Four new diketopiperazine alkaloids (1-4) were isolated from cultures of Penicillium fellutanum, and their structures were determined by MS and NMR measurements.
Subject(s)
Alkaloids/chemistry , Antineoplastic Agents/chemistry , Penicillium/chemistry , Alkaloids/pharmacology , Antineoplastic Agents/pharmacology , Culture Media , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Optical Rotation , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Tumor Cells, CulturedABSTRACT
Fungi of the species Penicillium piscarium produced diketopiperazine alkaloids (isorugulosuvine, puberuline, verrucosine, prolyltryptophanyldiketopiperazine, 12,13-dehydroprolyltryptophanyldiketopiperazine, fellutanine A, phenylalanylphenylalanyldiketopiperazine, as well as roquefortine and 3,12-dihydroroquefortine whose precursors are tryptophan, phenylalanine, leucine, proline, and histidine.
Subject(s)
Alkaloids/biosynthesis , Penicillium/metabolism , Piperazines/chemistry , Alkaloids/isolation & purification , Diketopiperazines , Species SpecificityABSTRACT
A synthesis of 3-(1H-3-indolyl)-4-(1-glycosyl-3-indolyl)furan-2,5-diones and -1H-pyrrole-2,5-diones modified with the residues of D-ribo-, D-xylo-, L-arabino-, D-galactopyranose, and D-lactose was described. Influence of the compounds prepared on DNA biosynthesis in CaOv cells was studied.
Subject(s)
Antineoplastic Agents/chemical synthesis , Glycosides/chemical synthesis , Antineoplastic Agents/pharmacology , Cell Division/drug effects , Glycosides/pharmacology , Humans , Magnetic Resonance Spectroscopy , Tumor Cells, Cultured/drug effectsABSTRACT
Three compounds with cytokinin activity have been isolated from the medium of Rhodospirillum rubrum grown photosynthetically. Two N-6 aminopurine cytokinins revealed in the medium were identical with those obtained from R. rubrum cells previously. The third compound with cytokinin activity in Amaranthus caudatus bioassay proved to be a simple phenolic compound with elemental composition C8H10O2. This cytokinin-like substance according to absorption spectra, mass spectrometry and 1H NMR spectra data was identified as 4-hydroxyphenethyl alcohol.
Subject(s)
Cytokinins/isolation & purification , Phenylethyl Alcohol/analogs & derivatives , Rhodospirillum rubrum/chemistry , Adenine/isolation & purification , Biological Assay , Chromatography, High Pressure Liquid , Chromatography, Thin Layer , Cytokinins/pharmacology , Magnetic Resonance Spectroscopy , Mass Spectrometry , Phenylethyl Alcohol/isolation & purification , Phenylethyl Alcohol/pharmacology , Plants/drug effects , Spectrometry, Fluorescence , Spectrophotometry, UltravioletSubject(s)
Adamantane/pharmacokinetics , Pseudomonas putida/metabolism , Rhodotorula/metabolism , Adamantane/analogs & derivatives , Biotransformation , Camphor 5-Monooxygenase , Chromatography, Gas , Cytochrome P-450 Enzyme System/metabolism , Magnetic Resonance Spectroscopy , Mass Spectrometry , Mixed Function Oxygenases/metabolism , Pseudomonas putida/enzymology , Rhodotorula/enzymologyABSTRACT
The strain Pseudomonas aeruginosa 142 isolated from the utilising PSBs bacterial association was capable of growth on 2-chloro- and 2,4-dichlorobenzoates as sole carbon sources, but it did not utilize 3-Cl, 4-Cl, 3,5-diCl- and 2,6-dichlorobenzoates. P. aeruginosa 142 dehalogenated 2-Cl-, 2,4-diCl- and 2,5-dichlorobenzoates in aerobic conditions. The release of chloride was not observed in microaerophilic and anaerobic conditions. The activities of catechol-1,2-dioxygenase and 4-chlorocatechol-1,2-dioxygenase were found in cell extracts after growth of this strain on 2,4-dichlorobenzoate. The presented results suggested that oxidative release of chloride in ortho-position is the first step of metabolism of 2-Cl-, 2,4-diCl- and 2,5-dichlorobenzoates. The further splitting of corresponding catechols is carried out by ortho-pathway.
Subject(s)
Chlorine/metabolism , Chlorobenzoates/metabolism , Dioxygenases , Pseudomonas aeruginosa/metabolism , Aerobiosis/physiology , Catechol 1,2-Dioxygenase , Catechols/chemistry , Molecular Structure , Oxidation-Reduction , Oxygenases/chemistry , Oxygenases/isolation & purificationABSTRACT
Pseudomonas strains harboring plasmids pBS3, pBS4, NAH7 were shown to carry out initial transformation of dibenzofurane to 4-[2'-(3'-hydroxy)-benzofuranyl]-2-keto-3-butenic acid due to broad substrate specificity of the enzymes of naphthalene catabolism nahA, nahB, nahC and nahD. These strains did not grow on dibenzofurane because of the inability of the enzyme nahE to split pyruvate of 4-[2'-(3' hydroxy)-benzofuranyl]-2-keto-3-butenic acid, which leads to accumulation of the latter. The strains harboring plasmids pBS2 and NPL-1 are not capable of any transformation of dibenzofurane.
Subject(s)
Benzofurans/pharmacokinetics , Naphthalenes/metabolism , Plasmids/genetics , Pseudomonas/metabolism , Biotransformation/physiology , Oxidation-Reduction , Substrate SpecificityABSTRACT
The monosporic plating of the avermectin-producing strain Streptomyces avermitilis VKM Ac-1301 with low activity showed the heterogeneity of the population. By selection of natural mutants the authors obtained a strain synthesizing up to 60 micrograms avermectin B1 per ml of culture liquid. The maximum avermectin yield was observed in the medium containing 7% glucose after 100-120 h of culture growth.