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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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