Journal
NATURAL PRODUCT RESEARCH
Volume 32, Issue 20, Pages 2437-2446Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/14786419.2017.1419230
Keywords
Terretonin M; penisimplicins; Aspergillus terreus TM8; taxonomy; antimicrobial activity
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Funding
- German Academic Exchange Service (DAAD)
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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, (3 beta, 5 alpha, 6 beta)-3,5,6-trihydroxy-ergosta-7,22-diene, sitostenone, linoleic acid, ergosterol, uracil, p-hydroxybenzoic 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. [GRAPHICS] .
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