Details

Autor(en) / Beteiligte

• Tran, Trong D.
• Wilson, Brice A.P.
• Henrich, Curtis J.
• Wendt, Karen L.
• King, Jarrod
• Cichewicz, Robert H.
• Stchigel, Alberto M.
• Miller, Andrew N.
• O'Keefe, Barry R.
• Gustafson, Kirk R.

Titel

Structure elucidation and absolute configuration of metabolites from the soil-derived fungus Dictyosporium digitatum using spectroscopic and computational methods

Ist Teil von

• Phytochemistry (Oxford), 2020-05, Vol.173, p.112278-112278, Article 112278

Ort / Verlag

England: Elsevier Ltd

Erscheinungsjahr

2020

Quelle

Access via ScienceDirect (Elsevier)

Beschreibungen/Notizen

• Following the discovery of a new class of compounds that inhibit the mucosa-associated lymphoid tissue lymphoma translocation 1 (MALT1) protease in a prior study, further chemical investigation of the Dictyosporium digitatum fungus resulted in the identification of 16 additional metabolites, including 12 undescribed compounds (1–12). The constitution and relative configuration of these new molecules were established by comprehensive NMR and HRMS analyses. Their absolute configurations were determined by employing Mosher's ester analysis and TDDFT ECD calculations. Two sesquiterpenes, dictyosporins A (1) and B (2), possess an undescribed eudesmen-type of structural scaffold. The ability of the isolated compounds to inhibit MALT1 proteolytic activity was evaluated, but none of them exhibited significant inhibition. The structure and absolute configuration of twelve metabolites from the fungus Dictyosporium digitatum were established by NMR and HRMS, in conjunction with Mosher's ester analysis and quantum mechanical ECD calculations. [Display omitted] •Twelve undescribed compounds were identified from the soil-derived fungus Dictyosporium digitatum.•Absolute configurations were established using Mosher's ester analysis and quantum chemical ECD calculations.•Two sesquiterpenes, dictyosporins A (1) and B (2), have a unique carbon-oxygen structural framework.