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Diterpenoids isolated from the Samoan marine sponge Chelonaplysilla sp. inhibit Mycobacterium tuberculosis growth

The Journal of Antibiotics volume 73, pages 568–573 (2020)Cite this article

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Abstract

Crude extracts of the marine sponge Chelonaplysilla sp. collected in Samoa, that were obtained from the NCI Open Repository (NCS 21903), inhibited Mycobacterium tuberculosis growth. Assay-guided fractionation of the extract led to the isolation and structural elucidation of the known diterpenoid macfarlandin D (1) and three new diterpenoids macfarlandins F (2), G (3), and H (4). Macfarlandin D (1) exhibited potent antimicrobial activity against M. tuberculosis with an MIC of 1.2 ± 0.4 µg mL−1. Macfarlandins F (2), G (3), and H (4) exhibited significantly weaker antitubercular activities, revealing SAR for the macfarlandin antitubercular pharmacophore. The structures of compounds 2, 3, and 4 were elucidated via detailed analysis of NMR and MS data.

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Acknowledgements

We thank Douglas Joerss, Aaron Korkegian, Carol Haggerty, Barry O’Keefe, and Dave Newman for technical assistance along with Roopa Ramamoorthi and Cathyryne Manner at BVGH for help in establishing the collaboration between IDRI and the University of British Columbia. Financial support was provided by an NSERC Discovery grant to RJA.

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Authors and Affiliations

  1. Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2016 Main Mall, Vancouver, BC, V6T 1Z1, Canada

    Josiane A. Monteiro de Oliveira, David E. Williams & Raymond J. Andersen

  2. TB Discovery Research, Infectious Disease Research Institute, Seattle, WA, 98102, USA

    Shilah Bonnett, James Johnson & Tanya Parish

  3. Seattle Children’s Research Institute, Seattle Children’s Hospital, Seattle, WA, 98109, USA

    Tanya Parish

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  1. Josiane A. Monteiro de Oliveira
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  2. David E. Williams
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  3. Shilah Bonnett
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  4. James Johnson
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  5. Tanya Parish
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  6. Raymond J. Andersen
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Correspondence to Tanya Parish or Raymond J. Andersen.

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The authors declare that they have no conflict of interest.

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Dedicated to Professor William Fenical, a pioneer and leader in the field of marine natural products chemistry, who has inspired all of us who attempt to follow in his footsteps.

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de Oliveira, J.A.M., Williams, D.E., Bonnett, S. et al. Diterpenoids isolated from the Samoan marine sponge Chelonaplysilla sp. inhibit Mycobacterium tuberculosis growth. J Antibiot 73, 568–573 (2020). https://doi.org/10.1038/s41429-020-0315-4

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  • DOI: https://doi.org/10.1038/s41429-020-0315-4

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