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

Back

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

Files and links (1)

url

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

Published Version

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.
DOI: 10.1016/j.phytochem.2020.112278
ISSN: 0031-9422
Organisation Unit: School of Science, Technology and Engineering; Centre for Bioinnovation; School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99451335502621
Output Type: Journal article

Metrics

14 Record Views

5 Times Cited - Web of Science

See more details

InCites Highlights

These are selected metrics from InCites Benchmarking & Analytics tool, related to this output

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

UN Sustainable Development Goals (SDGs)

This output has contributed to the advancement of the following goals:

Source: InCites