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

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

doi:10.1016/j.phytochem.2020.112278

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

Journal article

Peer reviewed

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

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

Phytochemistry, Vol.173, pp.1-9

2020

DOI: https://doi.org/10.1016/j.phytochem.2020.112278

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Abstract

Chemical Sciences

Biological Sciences

Medical and Health Sciences

dictyosporium digitatum

dictyosporiaceae

structure elucidation

Mosher's ester analysis

DFT calculations

dictyosporin

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.

Details

Title: Structure elucidation and absolute configuration of metabolites from the soil-derived fungus Dictyosporium digitatum using spectroscopic and computational methods
Authors: Trong D Tran (Author) - University of the Sunshine Coast
Brice A P Wilson (Author) - National Cancer Institute, United States
Curtis J Henrich (Author) - National Cancer Institute, United States
Karen L Wendt (Author) - University of Oklahoma, United States
Jarrod B King (Author) - University of Oklahoma, United States
Robert H Cichewicz (Author) - University of Oklahoma, United States
Alberto M Stchigel (Author) - Universitat Rovira i Virgil, Spain
Andrew N Miller (Author) - University of Illinois, United States
Barry R O'Keefe (Author) - National Cancer Institute, United States
Kirk R Gustafson (Author) - National Cancer Institute, United States
Publication details: Phytochemistry, Vol.173, pp.1-9
Publisher: Elsevier Ltd.
Date published: 2020
DOI: 10.1016/j.phytochem.2020.112278
ISSN: 0031-9422
Organisation Unit: School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering; Centre for Bioinnovation
Language: English
Record Identifier: 99451335502621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Biochemistry & Molecular Biology; Plant Sciences

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