Tetradehydrohalicyclamine B, a new proteasome inhibitor from the marine sponge Acanthostrongylophora ingens

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Highlights

  • Tetradehydrohalicyclamine B (1) was isolated from Acanthostrongylophora ingens.

  • 1 is the second example found to have a pyridinium ring in halicyclamines.

  • The absolute configuration of halicyclamine B (2) was determined by ECD experiment.

  • 1 and 2 inhibited the constitutive proteasome as well as the immunoproteasome.

  • The inhibitory activities of 2 were 4- to 10-fold more potent than those of 1.

Abstract

A new halicyclamine derivative, tetradehydrohalicyclamine B (1), was isolated from the marine sponge Acanthostrongylophora ingens, along with halicyclamine B (2) as proteasome inhibitors. Compound 1 is the second example found to have a pyridinium ring in the halicyclamine family. Although the relative configuration of 2 was previously determined by X-ray crystallographic analysis, here we determined the absolute configuration of 2 by ECD experiment. Compounds 1 and 2 inhibited the constitutive proteasome as well as the immunoproteasome. The inhibitory activities of 2 were 4- to 10-fold more potent than those of 1.

Section snippets

Acknowledgement

This work was supported by JSPS KAKENHI Grants 18406002 and 17H03994 to S.T.

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    These authors contributed equally to this work.

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