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New Sesterterpenes from the Antarctic Sponge Suberites sp.

Authors: Stine S. H. Olsen; Sydney K. Morrow; Julia L. Szabo; Michael N. Teng; Kim C. Tran; Charles D. Amsler; James B. McClintock; +1 Authors

New Sesterterpenes from the Antarctic Sponge Suberites sp.

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 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), previously reported suberitenones A–D (6–9), and oxaspirosuberitenone (10). Suberitenone K (1) was characterized as the 8-keto derivative of 6, while three new phenols, suberitandiol (2), abeosuberitandiol (3), and furanosuberitandiol (4), and the degraded sesterterpene norsuberitenone B (5) were also found. Compound 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 (XRD). Moderate activity towards RSV was reported for 9 and the new metabolite 1, with IC50 values of 15.0 μM and 39.8 μM, respectively.

Keywords

Chemistry and Materials Science, Sesterterpenes, Magnetic Resonance Spectroscopy, Molecular Structure, QH301-705.5, porifera, Organic Chemistry, suberitane, RSV, Antarctic Regions, <i>Suberites</i> sp., sesterterpenes, Antiviral Agents, Article, Porifera, Respiratory Syncytial Viruses, X-Ray Diffraction, Antarctica, Animals, Humans, Biology (General)

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
4
Top 10%
Average
Top 10%
Green
gold