Literature DB >> 32078832

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

Trong D Tran1, Brice A P Wilson1, Curtis J Henrich2, Karen L Wendt3, Jarrod King3, Robert H Cichewicz3, Alberto M Stchigel4, Andrew N Miller5, Barry R O'Keefe6, Kirk R Gustafson7.   

Abstract

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. Published by Elsevier Ltd.

Entities:  

Keywords:  DFT calculations; Dictyosporiaceae; Dictyosporin; Dictyosporium digitatum; Mosher's ester analysis; Structure elucidation

Mesh:

Substances:

Year:  2020        PMID: 32078832      PMCID: PMC7124996          DOI: 10.1016/j.phytochem.2020.112278

Source DB:  PubMed          Journal:  Phytochemistry        ISSN: 0031-9422            Impact factor:   4.072


  12 in total

1.  Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability.

Authors:  Steven G Smith; Jonathan M Goodman
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

2.  Enhancing NMR Prediction for Organic Compounds Using Molecular Dynamics.

Authors:  Eugene E Kwan; Richard Y Liu
Journal:  J Chem Theory Comput       Date:  2015-10-14       Impact factor: 6.006

Review 3.  Eudesmane sesquiterpenoids from the Asteraceae family.

Authors:  Quan-Xiang Wu; Yan-Ping Shi; Zhong-Jian Jia
Journal:  Nat Prod Rep       Date:  2006-08-07       Impact factor: 13.423

4.  The fungi: 1, 2, 3 ... 5.1 million species?

Authors:  Meredith Blackwell
Journal:  Am J Bot       Date:  2011-03-02       Impact factor: 3.844

Review 5.  Chemical ecology of fungi.

Authors:  Peter Spiteller
Journal:  Nat Prod Rep       Date:  2015-07       Impact factor: 13.423

6.  Application of Mosher's method for absolute configuration assignment to bioactive plants and fungi metabolites.

Authors:  Alessio Cimmino; Marco Masi; Marco Evidente; Stefano Superchi; Antonio Evidente
Journal:  J Pharm Biomed Anal       Date:  2017-02-21       Impact factor: 3.935

7.  Revision of the Massarineae (Pleosporales, Dothideomycetes).

Authors:  K Tanaka; K Hirayama; H Yonezawa; G Sato; A Toriyabe; H Kudo; A Hashimoto; M Matsumura; Y Harada; Y Kurihara; T Shirouzu; T Hosoya
Journal:  Stud Mycol       Date:  2015-11-18       Impact factor: 16.097

8.  Secondary Metabolites from the Fungus Dictyosporium sp. and Their MALT1 Inhibitory Activities.

Authors:  Trong D Tran; Brice A P Wilson; Curtis J Henrich; Louis M Staudt; Lauren R H Krumpe; Emily A Smith; Jarrod King; Karen L Wendt; Alberto M Stchigel; Andrew N Miller; Robert H Cichewicz; Barry R O'Keefe; Kirk R Gustafson
Journal:  J Nat Prod       Date:  2019-01-02       Impact factor: 4.050

9.  Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.

Authors:  Thomas R Hoye; Christopher S Jeffrey; Feng Shao
Journal:  Nat Protoc       Date:  2007       Impact factor: 13.491

10.  An unusual piceatannol dimer from Rheum austral D. Don with antioxidant activity.

Authors:  Lin Hu; Na-Na Chen; Qun Hu; Cui Yang; Qing-Song Yang; Fang-Fang Wang
Journal:  Molecules       Date:  2014-08-04       Impact factor: 4.411

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  2 in total

1.  Biosynthesis of Xylariolide D in Penicillium crustosum Implies a Chain Branching Reaction Catalyzed by a Highly Reducing Polyketide Synthase.

Authors:  Sina A Stierle; Shu-Ming Li
Journal:  J Fungi (Basel)       Date:  2022-05-09

Review 2.  The Novel Compounds with Biological Activity Derived from Soil Fungi in the Past Decade.

Authors:  Danyu Zhang; Shoujie Li; Mohan Fan; Changqi Zhao
Journal:  Drug Des Devel Ther       Date:  2022-10-12       Impact factor: 4.319

  2 in total

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