Edson Rodrigues-Fo

Universidade Federal de São Carlos, São Carlos, Estado de Sao Paulo, Brazil

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Publications (20)27.11 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: During our studies concerning endophytic fungi, two indole alkaloids were co-produced with verruculogen by Penicillium brasilianum isolated from Melia azedarach (Meliaceae). The compounds were isolated by the use of combined chromatographic procedures and identified by physical methods, mainly 1D- and 2D-NMR experiments. This article also describes the production of verruculogen TR-2, first described for this species of Penicillium, and a verruculogen TR-2C-11 epimer, that is a novel fungal natural product. The kinetic production of verruculogen and verruculogen TR-2 produced by P. brasilianum were evaluated in order to understand the involvement of verruculogen TR-2 in verruculogen biosynthesis.
    Natural product research 07/2012; · 1.01 Impact Factor
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    ABSTRACT: The oxidative potential of the fungus Penicillium brasilianum, a strain isolated as an endophyte from a Meliaceae plant (Melia azedarach), was investigated using 1-indanone as a substrate to track the production of monooxygenases. The fungus produced the dihydrocoumarin from 1-indanone with the classical Baeyer-Villiger reaction regiochemistry, and (-)-(R)-3-hydroxy-1-indanone with 78% ee. Minor compounds resulting from lipase and SAM activities were also detected. The biotransformation procedures were also applied to a collection of Penicillium and Aspergillus fungi obtained from M. azedarach and Murraya paniculata. The results showed that Baeyer-Villiger were mostly active in fungi isolated from M. azedarach. Almost all of the fungi tested produced 3-hydroxy-1-indanone..
    Journal of Microbiology and Biotechnology 06/2012; 22(6):832-7. · 1.40 Impact Factor
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    ABSTRACT: In our continuous studies on the chemistry of the endophytic fungus Penicillium griseoroseum, an endophyte isolated from fruits of Coffea arabica, we isolated clavatol, a dimethylated tetraketide, and its dimer which appears to be a novel natural compound. The studies also resulted in the identification of two known tetronic acids, viridicatic acid and terrestric acid, found in ethyl acetate and n-butanol extracts. Spectroscopic studies using 1-D and 2-D NMR and MS/MS analysis were performed to determine the structures of these compounds, first reported by this Penicillium. Two other tetronic acids congeners were identified through HPLC/MS/MS studies, based on fragmentation pattern of ions produced from ionised tetronic acids, and UV light absorptions.
    Natural product research 01/2012; 2012(pp. 1–8). · 1.01 Impact Factor
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    ABSTRACT: Endophytic fungi, isolated from a number of different species of tropical plants, were investigated for lipid biodiesel precursor production. The extracts produced from liquid cultures of these fungi were subjected to acidcatalyzed transesterification reactions with methanol producing methyl esters and then analyzed through chromatographic (GC-FID) and spectrometric techniques (MS, NMR ¹H). The European Standard Method, EN 14103, was used for the quantification of methyl esters extracted from the fungi of the species and genera studied. Xylariaceous fungi exhibited the highest concentrations of methyl esters (91%), and hence may be a promising source for biofuel.
    Journal of Microbiology and Biotechnology 07/2011; 21(7):728-33. · 1.40 Impact Factor
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    ABSTRACT: Four depsides, all of them new as natural products, were isolated from Cladosporium uredinicola solid-media culture and identified as 3-hydroxy-2,5-dimethylphenyl 2,4-dihydroxy-3,6-dimethylbenzoate (1), 3-hydroxy-2,4,5-trimethylphenyl 2,4-dihydroxy-3,6-dimethylbenzoate (2), 3-hydroxy-2,5-dimethylphenyl 3-[(2,4-dihydroxy-3,6-dimethylbenzoyl)oxy]-6-hydroxy-2,4-dimethylbenzoate (3), and 3-hydroxy-2,4,5-trimethylphenyl 3-[(2,4-dihydroxy-3,6-dimethylbenzoyl)oxy]-6-hydroxy-2,4-dimethylbenzoate (4). The endophytic fungus was isolated from Psidium guajava fruits and cultivated over sterilized rice. The compounds 1–4 were purified by classical chromatographic procedures, and the chemical structures were identified by spectroscopic studies, mainly 1D- and 2D-NMR and LC/ESI-MS/MS. Three of the isolated depsides exhibited moderate bacteriostatic and/or bactericide effects on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtillis.
    Helvetica Chimica Acta 01/2011; 94:1077. · 1.38 Impact Factor
  • Bianca Ferreira da Silva, Edson Rodrigues-Fo
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    ABSTRACT: Penicillium griseoroseum, isolated as an endophytic microorganism from Coffeea arabica seeds, was grown in Czapeck's medium containing 5,7,3′,4′,5′-pentamethoxyflavanone. The fungus incorporated a dimethylated tetraketide, clavatol, a typical fungal secondary metabolite, into the flavanone structure at C-6, resulting in a novel benzylated flavonoid. Clavatol was also found free in the fungus extract. The compounds were isolated by chromatographic procedures and identified by extensive spectroscopic studies, including MS/MS and 1D and 2D NMR. The process probably involves enzymes catalyzing C–C bound formation, which is uncommon in fungi. The possibility of fungi participation in the biosynthesis of plant benzylated flavonoids is discussed.Graphical abstractResearch highlights▶ Penicillium griseoroseum is and endophytic fungus found in coffee tree. ▶ This fungus produce clavatol, a small polyketide. ▶ When cultivated in the presence of a pentamethoxylflavanone, P. griseoroseum. ▶ Incorporated Clavatol in the flavanone.
    Journal of Molecular Catalysis B Enzymatic 12/2010; 67:184-188. · 2.82 Impact Factor
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    ABSTRACT: Biosynthetic studies on brasiliamides, potently convulsive and bacteriostatic compounds from an endophytic Penicillium brasilianum isolated from Melia azedarach (Meliaceae), confirms their phenylpropanoid origin, which is very uncommon in fungi. Feeding experiments with [2-(13)C]- phenylalanine indicated the incorporation of two units of this amino acid on brasiliamide structures. The first step in the phenylpropanoid pathway to those compounds was evaluated through enzymatic bioassays and confirmed the phenylalanine ammonia-lyase (PAL) participation. The metabolism of phenylalanine in this fungus is discussed.
    Journal of Microbiology and Biotechnology 03/2010; 20(3):622-9. · 1.40 Impact Factor
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    ABSTRACT: The title meroterpene neoaustin {systematic name: (1'S,2'R,3S,7'R,9'S,11'S,12'R)-11'-hydr-oxy-2,2,2',9',12'-penta-methyl-6',15'-dimethyl-ene-2,6-dihydro-13'-oxaspiro-[pyran-3,5'-tetra-cyclo-[7.5.1.0(1,11).0(2,7)]penta-deca-ne]-6,10',14'-trione}, C(25)H(30)O(6), comprises five rings, three six-membered and two five-membered. The absolute configuration was established based on [α(D)] = +166.91° (c 1.21, CH(2)Cl(2)). In the crystal, the mol-ecules are connected into a supra-molecular helical chain via O-H⋯O hydrogen bonds reinforced by C-H⋯O contacts.
    Acta Crystallographica Section E Structure Reports Online 03/2009; 65(Pt 3):o612. · 0.35 Impact Factor
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    ABSTRACT: The title meroterpene neoaustin systematic name: (1'S,2'R,3S,7'R,9'S,11'S,12'R)-11'-hydroxy- 2,2,2',9',12'-pentamethyl-6',15'-dimethylene-2,6-dihydro-13'-oxaspiro[py ran-3,5'-tetracyclo[7.5.1.0(1,11).0(2,7)]pentadecane]-6,10',14'-trione, C25H30O6, comprises five rings, three six-membered and two five-membered. The absolute configuration was established based on [alpha D] = + 166.91 degrees (c 1.21, CH2Cl2). In the crystal, the molecules are connected into a supramolecular helical chain via O-H center dot center dot center dot O hydrogen bonds reinforced by C-H center dot center dot center dot O contacts.
    Acta Crystallographica Section E Structure Reports Online 01/2009; 65:O612-U2621. · 0.35 Impact Factor
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    ABSTRACT: THE TITLE MEROTERPENE PREAUSTINOID A (SYSTEMATIC NAME: methyl 15-hydr-oxy-2,6,6,10,13,15-hexa-methyl-17-methyl-ene-7,14,16-trioxotetra-cyclo-[11.3.1.0(2,11).0(5,10)]hepta-decane-1-car-box-yl-ate), C(26)H(36)O(6), features a fused four-ring arrangement. Three rings are in different distorted chair conformations and the other is in a distorted boat conformation. The absolute configuration was established based on [α(D)] = -4.97° (c = 1.10 g l(-1), CH(2)Cl(2)). In the crystal, the mol-ecules are connected into supra-molecular chains via O-H⋯O hydrogen bonds.
    Acta Crystallographica Section E Structure Reports Online 01/2009; 65(Pt 2):o221. · 0.35 Impact Factor
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    ABSTRACT: The mosquito Aedes aegypti is an increasing problem of public health, being the vector responsible for dengue and Yellow Fever in tropical and subtropical regions. The aim of this work was to determine the potential larvicidal activity of a series of meroterpenoids, compounds 1-7, previously obtained fungal secondary metabolites from Penicillium sp., against the third-instar larvae of A. aegypti. The lethal concentrations (LC(50) and LC(90)) of 1-7 were evaluated 24 h after exposure. Dehydroaustin (4) was the most active meroterpenoid in the series, with an LC(50) value of 2.9 ppm, making it an attractive natural insecticide.
    Chemistry & Biodiversity 03/2008; 5(2):341-5. · 1.81 Impact Factor
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    ABSTRACT: The plant Sapindus saponaria is a good producer of terpenoidal and sesquiterpenoidal saponins, which are accumulated in its fruits. Although saponins usually act as antifungal compounds, a fungus was found living on the internal part of its pericarp. Tentative identification of the fungus, based on micro and macro-morphological aspects inspection, as well as on the secondary metabolite production, suggested the fungus to be a Xylariaceous microorganism. When the fungus is placed in contact with glycosides extracted from the host plant, or exogenous glycosides and other terpenoid compounds, it showed ability to transform them in another compounds. Analysis of these products using liquid chromatography and mass spectrometry showed that these biotransformations are mainly monohydroxylation and glycosilation. These findings contrasts most of the reports found in the literature which shows that hydrolysis at sugar chain are frequently observed during glycoside biotransformation by fungi.
    World Journal of Microbiology and Biotechnology 01/2008; 24(8):1341-1348. · 1.35 Impact Factor
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    ABSTRACT: Structural characterization by NMR spectroscopy and DFT calculations was performed for two dimeric naphtho-gamma-pyrones, the polyketides Aurasperone A and Fonsecinone A. Experimental data (13C NMR chemical shifts and interatomic geometries) were found to be in reasonable agreement with theoretical ones, obtained at B3LYP level for three different basis sets (6-31G/6-31G(d)/6-31G(d,p)). Additionally, the dipolar moments calculation allowed explaining the different solubility for these molecules. The 13C NMR theoretical chemical shifts were calculated with the GIAO method and the solvent effects were taken into account by means of the PCM approximation. In this work, the DFT/GIAO methodology shows to be a reliable tool in the assignment of experimental NMR chemical shifts of similar molecules.
    International Journal of Quantum Chemistry 01/2008; 108:2408-2416. · 1.17 Impact Factor
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    ABSTRACT: Complete assignments of 1H and 13C NMR chemical shifts of the polyketides aurasperone A and fonsecinone A were made by means of nuclear Overhauser enhancement and heteronuclear NMR correlation experiments. These compounds were isolated for the first time from Aspergillus aculeatus, an endophytic fungus obtained from leaves of Melia azedarach(Meliaceae).
    Magnetic Resonance in Chemistry 12/2005; 43(11):962-5. · 1.53 Impact Factor
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    ABSTRACT: A collection of endophytic fungi was obtained from living apparently symptomless roots, stems, leaves and fruits of Melia azedarach. This is an exotic tree introduced into Brazil from Asia and is a producer of insecticidal compounds. It grows very well and is apparently resistant to many pathogens. Each segment from the plant was sampled during two periods. A total of 55 fungal isolates were recovered. Hyphomycetes were more prevalent than Ascomycetes, Coelomycetes and Basidiomycetes. The genera Aspergillus and Penicillium were the most common in the plant.
    World Journal of Microbiology and Biotechnology 10/2003; 19(8):767-770. · 1.35 Impact Factor
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    ABSTRACT: In this study, gamma radiation from cobalt-60 was used to degrade the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D) dimethylamine salt in water in the presence of humic acid. The 2,4-D dimethylamine salt 1.13×10−4 mol dm−3 solution was irradiated with different doses. HPLC was used as an analytical technique to determine the degradation rate of herbicide studied. The results showed that the herbicide was completely degraded at an absorbed dose of 3 kGy. Degradation decreased when humic acid was added to all the doses. ESI/MS and MS/MS were used to identify the radiolytic degradation products. A fragmentation path for production of 4.6-dichlororesorcinol, is suggested. The radiolytic yields (G) were calculated.
    Radiation Physics and Chemistry 01/2003; · 1.38 Impact Factor
  • Regina M Geris dos Santos, Edson Rodrigues-Fo
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    ABSTRACT: A Penicillium sp was isolated from the root bark of Melia azedarach and cultivated over sterilized rice. After chromatographic procedures, two meroterpenes, named preaustinoid A and B, were obtained in addition to the known alkaloid verruculogen. Their structures were identified by extensive spectroscopic studies, and they exhibited moderate bacteriostatic effects on Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Bacillus sp.
    Phytochemistry 01/2003; 61(8):907-12. · 3.35 Impact Factor
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    ABSTRACT: Careful analysis of the electron impact (EI) mass spectral data obtained for the trimethylsilyl (TMS) ethers of known trichothecene mycotoxins of the deoxynivalenol group permitted the construction of a database useful for the identification of these mycotoxins directly from a gas chromatography/mass spectrometry (GC/MS) run. Structures of the ions at m/z 103, 117, 147 and 191 were elucidated by high-resolution mass spectrometry (HRMS) and a fragmentation scheme was suggested. The relative abundances of these ions in the mass spectra of the trichothecenes allowed a fast structural diagnosis during analysis of biological matrices. A new mycotoxin of this group, 3-acetylnivalenol, was tentatively identified by using MS data interpretation only.
    Rapid Communications in Mass Spectrometry 02/2002; 16(19):1827-35. · 2.51 Impact Factor
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    ABSTRACT: A Pestalotiopis sp. was isolated from the trunk bark of Pinus taeda. The fungus was cultivated in liquid medium and produced three highly oxygenated caryophyllene sequiterpene derivatives, named pestalotiopsolide A, taedolidol and 6-epitaedolidol, respectively. The sesquiterpenes were isolated by silica gel based chromatographic procedures and their structures were elucidated by NMR spectroscopic data.
    Zeitschrift fur Naturforschung C 58(5-6):319-24. · 0.60 Impact Factor
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    Regina M Geris dos Santos, Edson Rodrigues-Fo
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    ABSTRACT: From the methanol extract of Penicillium sp. cultivated on sterilized rice for three weeks we isolated three new meroterpenes preaustinoid A1, A2 and B1. The fungus was isolated from the root bark of Melia azedarach after surface sterilization. The structures of these compounds were identified by intensive spectroscopic studies.
    Zeitschrift fur Naturforschung C 58(9-10):663-9. · 0.60 Impact Factor