RESUMO
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.
Assuntos
Antibacterianos/metabolismo , Butadienos/metabolismo , Oxazinas/metabolismo , Penicillium/metabolismo , Fenóis/metabolismo , Astronave , Antibacterianos/biossíntese , Butadienos/química , Meios de Cultura , Oxazinas/química , Penicillium/crescimento & desenvolvimento , Fenóis/química , Fatores de Tempo , ZincoRESUMO
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.
Assuntos
Alcaloides/biossíntese , Penicillium/metabolismoRESUMO
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.
Assuntos
Aminoglicosídeos , Antineoplásicos/química , Antineoplásicos/farmacologia , Indóis , Antibacterianos/química , Antibacterianos/farmacologia , Antineoplásicos/síntese química , Bioquímica/métodos , Carbazóis/química , Ensaios de Seleção de Medicamentos Antitumorais , Furanos/química , Furanos/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Pirróis/química , Pirróis/farmacologia , Relação Estrutura-Atividade , Células Tumorais CultivadasAssuntos
Antibacterianos/química , Fungos/química , Antibacterianos/farmacologia , Bacillus subtilis/efeitos dos fármacos , Compostos Bicíclicos com Pontes/química , Compostos Bicíclicos com Pontes/farmacologia , Bactérias Gram-Negativas/efeitos dos fármacos , Lactonas/química , Lactonas/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
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.
Assuntos
Ergolinas/metabolismo , Sedimentos Geológicos/microbiologia , Penicillium/metabolismo , Regiões Árticas , Ergolinas/análise , Penicillium/crescimento & desenvolvimento , Penicillium/isolamento & purificaçãoRESUMO
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).
Assuntos
Alcaloides/biossíntese , Indóis , Penicillium chrysogenum/isolamento & purificação , Penicillium/isolamento & purificação , Astronave , Alcaloides/análise , Alcaloides/química , Cromatografia em Camada Fina , Ergolinas/análise , Ergolinas/metabolismo , Compostos Heterocíclicos de 4 ou mais Anéis , Hidroxiquinolinas/análise , Hidroxiquinolinas/metabolismo , Peso Molecular , Nitrogênio/análise , Ovomucina/análise , Ovomucina/biossíntese , Penicillium/metabolismo , Penicillium chrysogenum/metabolismo , Piperazinas/análise , Quinolonas/análise , Quinolonas/metabolismo , Espectrofotometria Ultravioleta , Triptaminas/análise , Triptaminas/biossínteseRESUMO
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.
Assuntos
Alcaloides/química , Penicillium/química , Piperazinas/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Fenilalanina , Piperazinas/isolamento & purificação , Piperazinas/farmacologia , Triptofano , Células Tumorais CultivadasRESUMO
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.
Assuntos
Penicillium/classificação , Classificação , Nitrogênio/metabolismo , Penicillium/metabolismoRESUMO
Four new diketopiperazine alkaloids (1-4) were isolated from cultures of Penicillium fellutanum, and their structures were determined by MS and NMR measurements.
Assuntos
Alcaloides/química , Antineoplásicos/química , Penicillium/química , Alcaloides/farmacologia , Antineoplásicos/farmacologia , Meios de Cultura , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Rotação Ocular , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Células Tumorais CultivadasRESUMO
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.
Assuntos
Alcaloides/biossíntese , Penicillium/metabolismo , Piperazinas/química , Alcaloides/isolamento & purificação , Dicetopiperazinas , Especificidade da EspécieRESUMO
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.
Assuntos
Antineoplásicos/síntese química , Glicosídeos/síntese química , Antineoplásicos/farmacologia , Divisão Celular/efeitos dos fármacos , Glicosídeos/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
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.
Assuntos
Citocininas/isolamento & purificação , Álcool Feniletílico/análogos & derivados , Rhodospirillum rubrum/química , Adenina/isolamento & purificação , Bioensaio , Cromatografia Líquida de Alta Pressão , Cromatografia em Camada Fina , Citocininas/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Álcool Feniletílico/isolamento & purificação , Álcool Feniletílico/farmacologia , Plantas/efeitos dos fármacos , Espectrometria de Fluorescência , Espectrofotometria UltravioletaAssuntos
Adamantano/farmacocinética , Pseudomonas putida/metabolismo , Rhodotorula/metabolismo , Adamantano/análogos & derivados , Biotransformação , Cânfora 5-Mono-Oxigenase , Cromatografia Gasosa , Sistema Enzimático do Citocromo P-450/metabolismo , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Oxigenases de Função Mista/metabolismo , Pseudomonas putida/enzimologia , Rhodotorula/enzimologiaRESUMO
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.
Assuntos
Cloro/metabolismo , Clorobenzoatos/metabolismo , Dioxigenases , Pseudomonas aeruginosa/metabolismo , Aerobiose/fisiologia , Catecol 1,2-Dioxigenase , Catecóis/química , Estrutura Molecular , Oxirredução , Oxigenases/química , Oxigenases/isolamento & purificaçãoRESUMO
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.
Assuntos
Benzofuranos/farmacocinética , Naftalenos/metabolismo , Plasmídeos/genética , Pseudomonas/metabolismo , Biotransformação/fisiologia , Oxirredução , Especificidade por SubstratoRESUMO
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.