Structure elucidation and synthesis of hydroxylated isatins from Streptomycetes
2016
Shaaban, Khaled A. | Shaaban, Mohamed | Nair, Vimal | Schuhmann, Imelda | Win, Hnin Yu | Lei, Lei | Dittrich, Birger | Helmke, Elisabeth | Schüffler, Anja | Laatsch, Hartmut
Chemical investigation of terrestrial and marine streptomycete isolates led to the identification of two new natural pigments, namely, 6-hydroxyisatin (3) and 6-hydroxy-5-methoxyisatin (4). Additionally, the strains delivered numerous known compounds, among them Nᵝ-acetyltryptamine, N-acetyltyramine, phenylacetamide, N-(2-phenethyl)acetamide, 1-acetyl-β-carboline, tyrosol, 2′-deoxyadenosine, 2′-deoxythymidine, anthranilic acid, 2′-deoxyuridine, indolyl-3-acetic acid, indolyl-3-carboxylic acid, and p-hydroxybenzoic acid. The isatin structures were deduced by NMR and mass studies and further confirmed by synthesis and by X-ray diffraction of the isomeric 5-hydroxy-6-methoxyisatin (5).
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