Mahorones, Highly Brominated Cyclopentenones from the Red Alga Asparagopsis taxiformis

The red alga Asparagopsis taxiformis (Rhodophyta, Bonnemaisoniaceae) has been shown to produce a large diversity of halogenated volatile organic compounds, with one to four carbons. As the distribution of this alga may expand worldwide, we implemented a research program that aims to understand the functions of its specialized metabolome in marine ecosystems. Phytochemical investigations performed on A. taxiformis gametophyte stages from the Indian Ocean revealed two new highly brominated cyclopentenones named mahorone (1) and 5-bromomahorone (2). They are the first examples of natural 2,3-dibromocyclopentenone derivatives. Their structure elucidation was achieved using spectrometric methods including NMR and MS. A standardized ecotoxicological assay was used as an assessment of their role in the environment, revealing high toxicities for both compounds (Ec(50) 0.16 mu M for 1 and 2). Additionally, both compounds were evaluated in antibacterial, antifungal, and cytotoxicity assays. Compounds 1 and 2 exhibit mild antibacterial activities against the human pathogen Acinetobacter baumannii.