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 f...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2014-05, Vol.77 (5), p.1150-1155
Main Authors: Greff, Stéphane, Zubia, Mayalen, Genta-Jouve, Grégory, Massi, Lionel, Perez, Thierry, Thomas, Olivier P
Format: Article
Language:English
Subjects:
Acinetobacter baumannii
Acinetobacter baumannii - drug effects
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - isolation & purification
Anti-Bacterial Agents - pharmacology
Antifungal Agents - chemistry
Antifungal Agents - isolation & purification
Antifungal Agents - pharmacology
Asparagopsis taxiformis
Bonnemaisoniaceae
Cyclopentanes - chemistry
Cyclopentanes - isolation & purification
Cyclopentanes - pharmacology
Environmental Sciences
Humans
Hydrocarbons, Brominated - chemistry
Hydrocarbons, Brominated - isolation & purification
Indian Ocean
Molecular Structure
Rhodophyta
Rhodophyta - chemistry
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Summary: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 (EC50 0.16 μM 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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np401094h