A new antibiotic produced by a strain of aspergillus flavipes

Casinovi, C. G.; Grandolini, Giuliano; Mercantini, R.; Oddo, N; Olivieri, Raffaela; Tonolo, Alberto

doi:10.1016/s0040-4039(00)89581-7

Cited by 34 publications

(21 citation statements)

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“…These data led to the known fungal metabolite flavipucine ( 3b ), first isolated from Aspergillus flavipes in 1968 by Casinovi et al6 and structurally revised in 1972 by Findlay et al7 The given optical rotation ([ α ] D = –88, ethanol), however, did not agree with our value ([ α ] D = +132, ethanol). The presence of only one enantiomer was suggested by HPLC on a chiral phase (Chiralcel OD‐R, only one peak) and the existence of a possible diastereomer could be excluded from the 1 H‐NMR spectrum.…”

Section: Structure Elucidationcontrasting

confidence: 56%

“…Using 15 μg of the compound on 6‐mm filter discs, only (+)‐flavipucine ( 3a ) exhibited good antibacterial activity against the tested bacteria with inhibition diameters of 16, 17, and 11 mm, respectively. Antibacterial activity has also been reported for the enantiomer (–)‐flavipucine ( 3b ) with MICs of approximately 25 μg mL –1 against B. subtilis and E. coli 6. In addition, 3a showed strong antifungal inhibition down to 7.81 ppm against Phytophthora infestans and down to 31.3 ppm against Septoria tritici .…”

Section: Biological Activitiesmentioning

confidence: 83%

“…From biomalt agar cultures, we isolated and identified the known metabolites chrysophanol ( 1 ) and hypothemycin ( 2 ), while liquid surface cultures using a glucose/maltose medium gave flavipucine ( 3a ) as the major metabolite. Addition of sodium acetate to surface cultures with the same medium expanded the metabolic profile of Phoma sp., resulting in the identification of flavipucine ( 3a ),6,7 isoflavipucine ( 4 ),8 and the new metabolite dihydroisoflavipucine ( 5 ). Surprisingly, the isolated flavipucine differed from the published data by the inverse value of optical rotation.…”

Section: Introductionmentioning

confidence: 99%

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(+)‐Flavipucine, the Missing Member of the Pyridione Epoxide Family of Fungal Antibiotics

et al. 2011

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From the culture extracts of the endophytic fungus, Phoma sp., isolated from the plant Salsola oppositifolia, five secondary metabolites were isolated and characterized. On biomalt agar medium, the strain produced the known substances chrysophanol (1) and hypothemycin (2), while from liquid-surface fermentations on a glucose/maltose medium, 2,4-pyridione derivatives were obtained. Interestingly, one of the isolated compounds, flavipucine (3a), showed a positive [α] D ; it, thus, was the enantiomer of the known, but configurationally as yet unassigned (-)-flavipucine (3b). By using quantum-chemical circular-dichroism calculations, the abso-

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Section: Structure Elucidationcontrasting

confidence: 56%

Section: Biological Activitiesmentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

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(+)‐Flavipucine, the Missing Member of the Pyridione Epoxide Family of Fungal Antibiotics

et al. 2011

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“…HPO derivatives prevalent in numerous natural products isolated from plants (such as ricinine (II) isolated from castor oil plants), and fungi (such as flavipucine (III) isolated from aspergillus flavipes). They exhibit a broad range of biological activities, such as antifungal, antibiotic, insecticidal, cytotoxic, neurotoxic, antiproliferation and antibacterial…”

Section: Introductionmentioning

confidence: 99%

Temperature‐Dependent Green Synthesis of New Series of Mannich Bases from 4‐Hydroxy‐pyridine‐2‐one and Their Antioxidant Activity Evaluation

2020

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A novel class of bio-based 4-hydroxy-2-pyridones was synthesized via Mannich reaction under solvent free conditions in absence any catalyst at room temperature. Interestingly, in thermal condition, the yields of these products were decreased and others products (from condensation of two molecules of 2pyridone and one molecule of aldehyde) were obtained. Then the antioxidant activity of the synthesized compounds were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay methods. In general all of products showed significant radical scavenging potential, but the derivatives of pyrrolidine were more significant effective than the piperidine derivatives. This protocol provides a convenient, room temperature, solvent-free, and catalyst-free access to new 3-substituted-4-hydroxy-2-pyridones.

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“…Dessa forma é possível enumerar algumas piridonas com ação antimicrobiana: apiosporamida (Alfatafta et al, 1994) fusapiridona A (Tsuchinari et al, 2007), kirromicina (Wolf e Zahner, 1971), harzianopiridona (Dickinson et al, 1989), atepenin B, B4 e A5 (Omura et al, 1988), flavipucina (Casinovi et al, 1968) e leporina A (TePaske et al, 1991); e com ação antifúngica: funiculosina (Ando et al, 1969) e ilicicolina H (Hayakawa et al, 1971). …”

Section: Ensaio Enzimático Sobre a Inibição De Gapdh De Trypanosoma Cunclassified

Otimização das condições de cultivo de Beauveria bassiana e Mycoleptodiscus indicus visando à produção de metabólitos com atividades antimicrobiana, antiparasitária e antitumoral

Andrioli¹

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Versão corrigida da Tese de Doutorado apresentada ao Programa de Pós-Graduação em 16/03/2012. A versão original encontra-se disponível na Faculdade de Ciências Farmacêuticas de Ribeirão Preto/USP Ribeirão Preto 2012 UNIVERSIDADE DE SÃO PAULO FACULDADE DE CIÊNCIAS FARMACÊUTICAS DE RIBEIRÃO PRETO Otimização das condições de cultivo de Beauveria bassiana e Mycoleptodiscus indicus visando à produção de metabólitos com atividades antimicrobiana, antiparasitária e antitumoral DedicatóriaDedico este trabalho à Jaime Andrioli e Lea T. Tedesco Andrioli, meus queridos pais que transmitiram a mim os mais importantes valores da vida, aos meus amados irmãos Gabriela e Ronald e a Deus pelo dom da vida. Agradecimento especialProf. Dr. Jairo Kenupp Bastos "Se eu não fosse imperador, desejaria ser professor. Não conheço missão maior e mais nobre que a de dirigir as inteligências jovens e preparar os homens do futuro." Dom Pedro II AgradecimentosÀ Deus, pelo dom da vida;Aos meus queridos pais, Jaime e Lea Andrioli;Aos meus amados irmãos, Gabriela e Ronald;À toda minha família, repleta de pessoas de bom coração; It is known that microorganisms are considered as promising source of bioactive molecules and endophytic and entomopathogenic fungi are included in this group. Therefore, we selected the entomopathogenic fungus Beauveria bassiana and the endophytic fungus Mycoleptodiscus indicus to initiate the prospection aiming to determine the favorable growing conditions to obtain secondary metabolites with biological activity. This work was guided by biological assays and chromatographic analysis. The fractions obtained in the cultivation in a large scale were subjected to biological tests (leishmanicidal, antimalarial, antimicrobial and cytotoxic). The dichloromethane and ethyl acetate fractions of both fungi showed promising results in antitumor and leishmanicidal assays. Then, these fractions were subjected to chromatographic processes that allowed the isolation of compounds whose chemical structures were elucidated through the use of NMR techniques, mass spectrometry, UV, IR, αD, and X-ray diffraction. From cultures of B. bassiana were obtained compounds from the pyridone class: pyridovericin, pyridovericin-N-O-(4-O-methyl-β-D-glucopyranoside) and pyridovericin-15-deoxy, being the latter two novel compounds; and alloxazine class: 7,8-dimethylalloxazine (lumichrome) and 1-methyl-11-hydroxylumichrome, being this last one unprecedented. From M. indicus cultures were obtained compounds from two classes: azaphilone and chromene. In this thesis we report the derivatives eugenitin, 6-methoxyeugenin and 9-hydroxyeugenin, which have been isolated from a wide variety of plants and fungi. Azaphilones are a class of structurally diverse fungal metabolites, known pigments with pyran-quinone structure and contains a highly oxygenated bicyclic core and a chiral quaternary center. Then, we obtained two known azaphilones: austdiol and austdiol diacetate (product of acetylation), and three unprecedent azaphilones: austdiol dimer, austdiol dihydrois...

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A new antibiotic produced by a strain of aspergillus flavipes

Cited by 34 publications

References 0 publications

(+)‐Flavipucine, the Missing Member of the Pyridione Epoxide Family of Fungal Antibiotics

(+)‐Flavipucine, the Missing Member of the Pyridione Epoxide Family of Fungal Antibiotics

Temperature‐Dependent Green Synthesis of New Series of Mannich Bases from 4‐Hydroxy‐pyridine‐2‐one and Their Antioxidant Activity Evaluation

Otimização das condições de cultivo de Beauveria bassiana e Mycoleptodiscus indicus visando à produção de metabólitos com atividades antimicrobiana, antiparasitária e antitumoral

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