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Suberitamides A-C, Aryl Alkaloids from a Pseudosuberites sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity

  1. Author:
    Kim,Chang-Kwon [ORCID]
    Wang,Dongdong [ORCID]
    Wilson,Brice [ORCID]
    Saurí, Josep
    Voeller, Donna
    Lipkowitz, Stanley
    O'Keefe,Barry
    Gustafson,Kirk [ORCID]

  2. Author Address

    Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, MD 21702-1201, USA., Structure Elucidation Group, Analytical Research and Development, Merck & Co., Inc., Boston, MS 02115, USA., Women 39;s Malignancies Branch, Center for Cancer Research, National Cancer Institute, Bethesda, MD 20892-1578, USA., Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick, MD 21701-1201, USA.,
    1. Year: 2020
    2. Date: NOV
    3. Epub Date: 2020 10 28
  2. Journal: Marine drugs
    1. 18
    2. 11
    3. Pages: pii: E536
  4. Type of Article: Article
  5. Article Number: 536
  6. ISSN: 1660-3397
  1. Abstract:

    Three new aryl alkaloids named suberitamides A-C (1-3), were isolated from an extract of the marine sponge Pseudosuberites sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis. To assign the challenging relative configuration of the saturated five-membered ring in suberitamide A (1), a simple and efficient NMR protocol was applied that is based on the analysis of 2- and 3-bond 1H-13C spin-spin coupling constants using a PIP (pure in-phase) HSQMBC (heteronuclear single quantum multiple bond correlation) IPAP (in-phase and anti-phase) experiment. Suberitamides A (1) and B (2) inhibited Cbl-b, an E3 ubiquitin ligase that is an important modulator of immune cell function, with IC50 values of approximately 11 µM.

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External Sources

  1. View Full Text
  2. DOI: 10.3390/md18110536
  3. PMID: 33126420
  4. View record in Web of Science®
  5. WOS: 000593681900001
  6. PII : md18110536

Library Notes

  1. Fiscal Year: FY2020-2021
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