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

Josiane A.Monteiro de Oliveira; David E. Williams; Shilah Bonnett; James Johnson; Tanya Parish; Raymond J. Andersen

doi:10.1038/s41429-020-0315-4

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

Josiane A.Monteiro de Oliveira
, David E. Williams
, Shilah Bonnett
, James Johnson
, Tanya Parish
, Raymond J. Andersen

University of British Columbia
Infectious Disease Research Institute
TB Discovery Research
Seattle Children's Research Institute
Seattle Children's Hospital

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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.

Original language	English
Pages (from-to)	568-573
Number of pages	6
Journal	Journal of Antibiotics
Volume	73
Issue number	8
DOIs	https://doi.org/10.1038/s41429-020-0315-4
Publication status	Published - 13 May 2020
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being
SDG 14 Life Below Water

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10.1038/s41429-020-0315-4

Cite this

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title = "Diterpenoids isolated from the Samoan marine sponge Chelonaplysilla sp. inhibit Mycobacterium tuberculosis growth",

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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doi = "10.1038/s41429-020-0315-4",

language = "English",

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journal = "Journal of Antibiotics",

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T1 - Diterpenoids isolated from the Samoan marine sponge Chelonaplysilla sp. inhibit Mycobacterium tuberculosis growth

AU - de Oliveira, Josiane A.Monteiro

AU - Williams, David E.

AU - Bonnett, Shilah

AU - Johnson, James

AU - Parish, Tanya

AU - Andersen, Raymond J.

PY - 2020/5/13

Y1 - 2020/5/13

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AB - 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.

U2 - 10.1038/s41429-020-0315-4

DO - 10.1038/s41429-020-0315-4

M3 - Article

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SN - 0021-8820

VL - 73

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JO - Journal of Antibiotics

JF - Journal of Antibiotics

IS - 8

ER -

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

Abstract

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