Preprint Article Version 1 This version is not peer-reviewed

New Sesterterpenes from the Antarctic Sponge Suberites sp.

Version 1 : Received: 5 November 2024 / Approved: 6 November 2024 / Online: 6 November 2024 (16:52:29 CET)

How to cite: Olsen, S. S.; Morrow, S. K.; Szabo, J. L.; Teng, M. N.; Tran, K. C.; Amsler, C. D.; McClintock, J. B.; Baker, B. J. New Sesterterpenes from the Antarctic Sponge Suberites sp.. Preprints 2024, 2024110376. https://doi.org/10.20944/preprints202411.0376.v1 Olsen, S. S.; Morrow, S. K.; Szabo, J. L.; Teng, M. N.; Tran, K. C.; Amsler, C. D.; McClintock, J. B.; Baker, B. J. New Sesterterpenes from the Antarctic Sponge Suberites sp.. Preprints 2024, 2024110376. https://doi.org/10.20944/preprints202411.0376.v1

Abstract

Chemical investigation of the Antarctic sponge Suberites sp. has previously led to the identification of new suberitane derivatives, some of which show bioactivity toward the respiratory syncytial virus (RSV). Our ongoing NMR-guided investigation of new specimens of the sponge resulted in the isolation of five new analogs (1-5), the previously reported suberitenones A-D (6-9) and oxaspirosuberitenone (10). Suberitenone K (1) was characterized as the 8-keto derivative of suberitenone A, while three new phenols, suberitandiol (2), abeosuberitandiol (3), and furanosuberitandiol (4), and the degraded sesterterpene norsuberitenone B (5) were also found. 3 displays a ring contraction while 4 has a new dihydrofuran ring. Structural characterization was achieved by a combination of NMR, HR-MS, and X-ray diffraction. Suberitenone D and the new metabolite suberitenone K showed moderate activity towards RSV, while norsuberitenone B and furanosuberitandiol were found to have mild activity.

Keywords

Suberites sp.; sesterterpenes; suberitane; porifera; Antarctica; RSV

Subject

Chemistry and Materials Science, Organic Chemistry

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