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

  1. Author:
    Tran, Trong D
    Wilson,Brice
    Henrich,Curtis
    Wendt, Karen L
    King, Jarrod
    Cichewicz, Robert H
    Stchigel, Alberto M
    Miller, Andrew N
    O'Keefe,Barry
    Gustafson,Kirk

  2. Author Address

    Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702-1201, United States., Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702-1201, United States; Basic Science Program, Frederick National Laboratory for Cancer Research, Frederick, MD, 21702-1201, United States., Natural Products Discovery Group, Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK, 73019-5251, United States., Mycology Unit, Universitat Rovira i Virgili, C/ Sant Lloren 231; 21, 43201, Reus, Spain., University of Illinois, Illinois Natural History Survey, 1816 South Oak Street, Champaign, IL, 61820-6970, United States., Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702-1201, United States; Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick, MD, 21702-1201, United States., Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD, 21702-1201, United States. Electronic address: gustafki@mail.nih.gov.,
    1. Year: 2020
    2. Date: May
    3. Epub Date: 2020 02 17
  2. Journal: Phytochemistry
    1. 173
    2. Pages: 112278
  4. Type of Article: Article
  5. Article Number: 112278
  6. ISSN: 0031-9422
  1. 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.

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External Sources

  1. View Full Text
  2. DOI: 10.1016/j.phytochem.2020.112278
  3. PMID: 32078832
  4. View record in Web of Science®
  5. WOS: 000528188900016
  6. PII : S0031-9422(19)30782-4

Library Notes

  1. Fiscal Year: FY2019-2020
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