Antibacterial Oligomeric Polyphenols from the Green Alga Cladophora socialis

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 Cladophor...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-05, Vol.84 (9), p.5035-5045
Main Authors: Lavoie, Serge, Sweeney-Jones, Anne Marie, Mojib, Nazia, Dale, Brandon, Gagaring, Kerstin, McNamara, Case W, Quave, Cassandra L, Soapi, Katy, Kubanek, Julia
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03218