Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

Beilstein J Org Chem. 2024 Dec 9:20:3215-3220. doi: 10.3762/bjoc.20.267. eCollection 2024.

Abstract

A new psammaplysin derivative, ceratinadin G (1), was obtained from the Okinawan marine sponge Pseudoceratina sp., and the gross structure was clarified through spectroscopic and spectrometric analyses. The absolute configuration of compound 1 was established by comparing its NMR and ECD data with those of the known psammaplysin derivative, psammaplysin F (2). Ceratinadin G (1) is a rare nitrile containing a cyano group as aminoacetonitrile, and is the first psammaplysin derivative possessing a cyano group. In vitro assays indicated that compound 1 displayed moderate cytotoxicity against L1210 murine leukemia cells and KB epidermoid carcinoma cells.

Keywords: Pseudoceratina sp.; ceratinadin; cytotoxicity; marine sponge; psammaplysin.

Grants and funding

This work was partially supported by the Kobayashi Foundation and JSPS KAKENHI (Grant Numbers JP19K16398, JP20K07116, JP24K09860).