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Antibacterial oligomeric polyphenols from the green alga Cladophora socialis

Lavoie Serge, Sweeney-Jones Anne Marie, Mojib Nazia, Dale Brandon, Gagaring Kerstin, McNamara Case W., Quave Cassandra L., Soapi Katy et Kubanek Julia. (2019). Antibacterial oligomeric polyphenols from the green alga Cladophora socialis. The Journal of Organic Chemistry, 84, (9), p. 5035-5045.

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URL officielle: http://dx.doi.org/doi:10.1021/acs.joc.8b03218

Résumé

A series of oligomeric phenols including the known natural product 3,4,3′,4′-tetrahydroxy-1,1′-biphenyl (3), the previously synthesized 2,3,8,9-tetrahydroxybenzo[c]chromen-6-one (4), and eight new related natural products, cladophorols B–I (5–12), were isolated from the Fijian green alga Cladophora socialis and identified by a combination of NMR spectroscopy, mass spectrometric analysis, and computational modeling using DFT calculations. J-resolved spectroscopy and line width reduction by picric acid addition aided in resolving the heavily overlapped aromatic signals. A panel of Gram-positive and Gram-negative pathogens used to evaluate pharmacological potential led to the determination that cladophorol C (6) exhibits potent antibiotic activity selective toward methicillin-resistant Staphylococcus aureus (MRSA) with an MIC of 1.4 μg/mL. Cladophorols B (5) and D–H (7–11) had more modest but also selective antibiotic potency. Activities of cladophorols A–I (4–12) were also assessed against the asexual blood stages of Plasmodium falciparum and revealed cladophorols A (4) and B (5) to have modest activity with EC50 values of 0.7 and 1.9 μg/mL, respectively.

Type de document:Article publié dans une revue avec comité d'évaluation
ISSN:0022-3263
Volume:84
Numéro:9
Pages:p. 5035-5045
Version évaluée par les pairs:Oui
Date:2019
Identifiant unique:10.1021/acs.joc.8b03218
Sujets:Sciences naturelles et génie > Sciences naturelles > Biologie et autres sciences connexes
Sciences naturelles et génie > Sciences naturelles > Chimie
Sciences de la santé > Sciences médicales > Pharmacologie
Département, module, service et unité de recherche:Départements et modules > Département des sciences fondamentales
Mots-clés:Cladophora socialis, green alga, polyphenol, oligomer, antibiotic
Déposé le:01 sept. 2021 19:01
Dernière modification:01 sept. 2021 19:01
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