Terretonin M: A new meroterpenoid from the thermophilic Aspergillus terreus TM8 and revision of the absolute configuration of penisimplicins |
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| Authors: | Mohamed Shaaban Mohammad Magdy El-Metwally Ahmed Adel Abdel-Razek Hartmut Laatsch |
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| Institution: | 1. Chemistry of Natural Compounds Department, Division of Pharmaceutical Industries, National Research Centre, Dokki-Cairo, Egypt;2. University of G?ttingen, Institute of Organic and Biomolecular Chemistry, G?ttingen, Germanymshaaba@gmail.com;4. Faculty of Science, Botany and Microbiology Department, Damanhour University, Damanhour, Egypt;5. Faculty of Science, Botany Department, Mansoura University, El-Mansoura, Egypt;6. University of G?ttingen, Institute of Organic and Biomolecular Chemistry, G?ttingen, Germany |
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| Abstract: | Terretonin M (1), a new highly oxygenated tetracyclic meroterpenoid, was isolated from the thermophilic fungus Aspergillus terreus TM8 together with 10 known metabolites: terrelumamide A, asterrelenin, 7-prenyl-indolyl-3-carbaldehyde, (3β,5α,6β)-3,5,6-trihydroxy-ergosta-7,22-diene, sitostenone, linoleic acid, ergosterol, uracil, p-hydroxy-benzoic acid, and indole-3-carboxylic acid. The chemical structure of the new compound was elucidated by extensive 1D, 2D NMR, and ESI HR mass measurements, and by comparison with literature data. The absolute configuration of 1 was resolved by analysis of its NOESY spectrum and comparison of its experimental ECD spectrum with DFT calculations. In parallel to this work, revision of the absolute configuration of penisimplicins 3a and 3b is proposed on the basis of their ECD and ORD data. The isolation and taxonomic characterisation of A. terreus TM8 is reported, and the antimicrobial activity of the crude extract and the isolated compounds was studied as well. |
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| Keywords: | Terretonin M penisimplicins Aspergillus terreus TM8 taxonomy antimicrobial activity |
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