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An anti-mycobacterial bisfunctionalized sphingolipid and new bromopyrrole alkaloid from the Indonesian marine sponge Agelas sp.

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Abstract

In the course of our studies on anti-mycobacterial substances from marine organisms, the known dimeric sphingolipid, leucettamol A (1), was isolated as an active component, together with the new bromopyrrole alkaloid, 5-bromophakelline (2), and twelve known congeners from the Indonesian marine sponge Agelas sp. The structure of 2 was elucidated based on its spectroscopic data. Compound 1 and its bis TFA salt showed inhibition zones of 12 and 7 mm against Mycobacterium smegmatis at 50 μg/disk, respectively, while the N,N’-diacetyl derivative (1a) was not active at 50 μg/disk. Therefore, free amino groups are important for anti-mycobacterial activity. This is the first study to show the anti-mycobacterial activity of a bisfunctionalized sphingolipid. Compound 13 exhibited weak PTP1B inhibitory activity (29% inhibition at 35 μM).

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Acknowledgements

This work was supported in part by the Kanae Foundation for the Promotion of Medical Science to H. Y. and the Grant for Basic Science Research Projects from The Sumitomo Foundation to H. Y. We express our thanks to Dr. K. Ogawa of the Z. Nakai Laboratory for the identification of the marine sponge and to Mr. T. Matsuki and S. Sato for the measurements of mass spectra.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai, 981-8558, Japan

    Delfly B. Abdjul, Hiroyuki Yamazaki, Syu-ichi Kanno, Ayako Tomizawa, Kazuyo Ukai & Michio Namikoshi

  2. Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado, 95115, Indonesia

    Delfly B. Abdjul & Deiske A. Sumilat

  3. Faculty of Mathematic and Natural Sciences, Sam Ratulangi University, Kampus Bahu, Manado, 95115, Indonesia

    Henki Rotinsulu & Defny S. Wewengkang

  4. Faculty of Nursing, University of Pembangunan Indonesia, Bahu, Manado, 95115, Indonesia

    Magie M. Kapojos

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  1. Delfly B. Abdjul
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  2. Hiroyuki Yamazaki
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  3. Syu-ichi Kanno
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Correspondence to Hiroyuki Yamazaki.

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Abdjul, D.B., Yamazaki, H., Kanno, Si. et al. An anti-mycobacterial bisfunctionalized sphingolipid and new bromopyrrole alkaloid from the Indonesian marine sponge Agelas sp.. J Nat Med 71, 531–536 (2017). https://doi.org/10.1007/s11418-017-1085-6

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  • DOI: https://doi.org/10.1007/s11418-017-1085-6

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