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April 24, 2026Organic Letters1 citations

Vosamidines A–C, Polycyclic 2-Aminoimidazole Alkaloids from a Marine Calcareous Sponge Vosmaeropsis wilsoni

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SSSarath P. D. SenadeeraTarget (United States)DWD J WangXihua UniversityBWBrice A. P. WilsonTarget (United States)

Key Points

  • To isolate and characterize three polycyclic alkaloids from a marine sponge and assess their biological activity.
  • Isolated vosamidines A-C from sponge Vosmaeropsis wilsoni.
  • Determined structures using spectroscopic and computational analysis.
  • Evaluated biological activity in an oncogenic fusion protein kinase assay.
  • Vosamidine A features a unique pentacyclic core structure.
  • Vosamidine B is an oxidized derivative of Vosamidine A with rearrangement.
  • Vosamidine C has a hexacyclic ring with a thioether, and compounds 1 and 2 showed modest inhibition in the kinase assay.

Abstract

Vosamidines A-C (1-3), three polycyclic 2-aminoimidazole alkaloids, were isolated from a marine calcareous sponge, Vosmaeropsis wilsoni. Their structures were determined by extensive analysis of spectroscopic and spectrometric data, along with ECD computational studies. Vosamidine A possesses a 6/5/5/5/6/15(6)(5)-fused ring system based on a unique pentacyclic core. Vosamidine B is an oxidized and ring rearranged derivative of 1. Vosamidine C possesses an unusual 5/5/6/5/5/8 hexacyclic ring system incorporating a thioether ring. Plausible biosynthetic pathways for 1-3 are proposed. Compounds 1 and 2 had modest inhibition in the oncogenic fusion protein kinase DNAJB1-PKAcα assay.

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Cite This Study

Senadeera et al. (2026) studied this question.

synapsesocial.com/papers/69eb099a553a5433e34b40b2https://doi.org/10.1021/acs.orglett.6c00476
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