Pseudoceratonic Acid and Moloka’iamine Derivatives from the Red Sea Verongiid Sponge <i>Pseudoceratina arabica</i>

Abstract

During an investigation of the chemistry of the Red Sea Verongiid sponge Pseudoceratina arabica, we discovered a small molecule, pseudoceratonic acid (1), along with the new moloka’iamine derivatives, ceratinines N (2), O (3), and the previously reported compounds moloka’iamine (4), hydroxymoloka’iamine (5) and ceratinamine (6). The structural assignments of 1–6 were accomplished by interpretation of their NMR and HRESIMS spectral data. Pseudoceratonic acid possesses a dibrominated hydrazine-derived functional group not found in any reported chemical compound. Pseudoceratonic acid selectively inhibited the growth of E. coli and S. aureus, while ceratinine N selectively inhibited C. albicans. Further, ceratinine N showed potent cytotoxic effects against the triple-negative breast cancer, colorectal carcinoma, and human cervical carcinoma cell lines down to 2.1 µM.

Keywords

• Red Sea Verongiid sponge
• <i>Pseudoceratina arabica</i>
• pseudoceratonic acid
• dibromotyrosine alkaloids
• ceratinines N and O
• structure determinations