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Iodinated meroditerpenes from a red alga Callophycus sp.

Lavoie Serge, Brumley David, Alexander Troy S., Jasmin Christine, Carranza Franz A., Nelson Kate, Quave Cassandra L. et Kubanek Julia. (2017). Iodinated meroditerpenes from a red alga Callophycus sp. The Journal of Organic Chemistry, 82, (8), p. 4160-4169.

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URL officielle: http://dx.doi.org/doi:10.1021/acs.joc.7b00096

Résumé

Unique iodine-containing meroditerpenes iodocallophycoic acid A (1) and iodocallophycols A–D (2–5) were discovered from the Fijian red alga Callophycus sp. Because flexibility of the molecular skeleton impaired full characterization of relative stereochemistries by NMR spectroscopy, a DFT-based theoretical model was developed to derive relevant interproton distances which were compared to those calculated from NOE measurements, yielding the relative stereochemistries. The correct 2S,6S,7S,10S,14S enantiomers were then identified by comparison of theoretical and experimental ECD spectra. Biological activities of these iodinated and brominated meroditerpenes and additional new, related bromophycoic acid F (6) and bromophycoic acid A methyl ester (7), were evaluated for relevant human disease targets. Iodocallophycoic acid A (1) showed moderate antibiotic activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF) with MIC values of 1.4 and 2.2 μg mL–1, respectively. It also potentiated the anti-MRSA activity of oxacillin in a synergistic fashion, resulting in an 8-fold increase in oxacillin potency, for a MIC of 16 μg mL–1.

Type de document:Article publié dans une revue avec comité d'évaluation
ISSN:0022-3263
Volume:82
Numéro:8
Pages:p. 4160-4169
Version évaluée par les pairs:Oui
Date:2017
Identifiant unique:10.1021/acs.joc.7b00096
Sujets:Sciences naturelles et génie > Sciences naturelles > Chimie
Département, module, service et unité de recherche:Départements et modules > Département des sciences fondamentales
Mots-clés:Callophycus, meroditerpenes, iodocallophycoic acid, iodocallophycols, biological activities
Déposé le:01 sept. 2021 18:34
Dernière modification:01 sept. 2021 18:34
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