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Mondol M.A.M.,University of Gottingen | Surovy M.Z.,Bangabandhu Sheikh Mujibur Rahman Agricultural University | Islam M.T.,Bangabandhu Sheikh Mujibur Rahman Agricultural University | Schuffler A.,Institute of Biotechnology and Drug Research | Laatsch H.,University of Gottingen
Journal of Agricultural and Food Chemistry | Year: 2015

The cytotoxicity of the extract obtained from Myrothecium roridum M10 and a characteristic 1H signal at δH ∼8 led to the assumption that verrucarin/roridin-type compounds were present. Upscaling on rice medium led to the isolation of four new metabolites: verrucarins Y (1) and Z (6) (macrocyclic trichothecenes), bilain D (12) (a diketopiperazine derivative), and hamavellone C (14) (an unusual cyclopropyl diketone). In addition, nine known trichothecenes [verrucarin A (3), 16-hydroxyverrucarin A (5), verrucarin B (7), 16-hydroxyverrucarin B (8), verrucarin J (2), verrucarin X (4), roridin A (9), roridin L-2 (10), and trichoverritone (11)] and a bicyclic lactone [myrotheciumone A (15)] were identified. Their structures and configurations were determined by spectroscopic methods, published data, Mosher's method, and considering biosyntheses. Some trichothecenes showed motility inhibition followed by lysis of the zoospores against devastating Phytophthora nicotianae within 5 min. Compounds 2, 3, 7, and 9 also exhibited potent activities against Candida albicans and Mucor miehei. © 2015 American Chemical Society. Source


Arfan M.,University of Gottingen | Shaaban K.A.,University of Gottingen | Schuffler A.,Institute of Biotechnology and Drug Research | Laatsch H.,University of Gottingen
Natural Product Communications | Year: 2012

Chemical investigation of the terrestrial Streptomyces sp. isolates GT2005/020 and ANK148 led to the isolation of two microbial furanone derivatives, 5-hydroxy-4-methylnaphtho[1,2-b]furan-3-one (1) and 4-hydroxy-5-methyl-furan-3-one (2), respectively, which have some similarity to quorum sensing molecules of the AI-2 type. In addition, the known compounds chalcomycin, ferulic acid, indole-3-acetic acid, uracil, thymine, 2′-deoxy-thymidin, monensin B (3), phencomycin, and 1-acetyl-β- carboline were isolated. The structures of 1 and 2 were deduced from extensive studies of NMR (1D and 2D) and mass spectra. Additionally, the complete NMR shift assignments for monensin B (3) using H-H COSY, HMQC and HMBC experiments are reported here for the first time. We are describing the taxonomy and fermentation of the producing strains, the structure elucidation of the new metabolites and their bioactivity. (Chemical Equation Presented). Source


Piyasena N.P.K.G.,University of Gottingen | Schuffler A.,Institute of Biotechnology and Drug Research | Laatsch H.,University of Gottingen
Natural Product Communications | Year: 2015

A new nitrogen containing compound named xylactam B (2), along with a further eight known compounds, ceramide 2a, cerebroside B, cyclo(prolyl,valyl), marmesin, 5-methoxycarbonylmellein, 5-methylmellein, polypropylene glycol and p-hydroxybenzoic acid, were isolated from an endophytic Xylaria sp. The structure elucidation of the new compound and the other isolates was carried out with the help of spectroscopic analyses and databases. Source


Zinad D.S.,University of Gottingen | Shaaban K.A.,University of Gottingen | Ali Abdalla M.,University of Gottingen | Islam Md.T.,University of Gottingen | And 3 more authors.
Natural Product Communications | Year: 2011

Four isocoumarins have been isolated from the terrestrial Streptomyces sp. ANK302, namely 6,8-dimethoxy-3-methylisocoumarin (1), 6,8-dihydroxy-3- methylisocoumarin (2), 6,8-dihydroxy-7-methoxy-3-methylisocoumarin (3), and 6,7,8-trimethoxy-3-methylisocoumarin (4). Compound 1 is a new naturally-occurring isocoumarin, and 2 was isolated as a new bacterial product. The structures 1-4 were deduced from high resolution mass, 1D and 2D NMR spectra and by comparison with related compounds from the literature. Compound 2 showed a strong zoosporicidal activity at a concentration of 5 μg/mL against a phytopathogenic oomycete, Plasmopara viticola, and 1 was active against Candida albicans. Source


Talontsi F.M.,University of Gottingen | Dittrich B.,University of Gottingen | Schuffler A.,Institute of Biotechnology and Drug Research | Sun H.,Max Planck Institute for Biophysical Chemistry | Laatsch H.,University of Gottingen
European Journal of Organic Chemistry | Year: 2013

In the search for new compounds to protect plants from fungi, an endophytic fungus, Epicoccum sp. CAFTBO, obtained from Theobroma cacao was found to produce three polyoxygenated polyketides, namely epicolactone (1) and epicoccolides A (2) and B (3), together with seven known metabolites. The structures of these compounds were elucidated by a combination of detailed spectroscopic and spectrometric analyses as well as DFT calculations of the electronic circular dichroism spectra and the single-crystal X-ray diffraction analysis of 1. Compounds 1-3 showed potent antimicrobial activities and significant inhibitory effects on the mycelial growth of two peronosporomycete phytopathogens, Pythium ultimum and Aphanomyces cochlioides, and the basidiomycetous fungus Rhizoctonia solani. Three polyoxygenated polyketides 1-3, together with seven known metabolites, have been isolated from Epicoccum sp. CAFTBO, an endophytic fungus found in Theobroma cacao. Compounds 1-3 showed potent antimicrobial activities and significant inhibitory effects on the mycelial growth of two peronosporomycete phytopathogens and the basidiomycetous fungus Rhizoctonia solani. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Source

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