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Antibacterial Oligomeric Polyphenols from the Green Alga Cladophora socialis

Lavoie, Serge and Sweeney-Jones, Anne Marie and Mojib, Nazia and Dale, Brandon and Gagaring, Kerstin and McNamara, Case W. and Quave, Cassandra L. and Soapi, Katy M. and Kubanek, Julia (2019) Antibacterial Oligomeric Polyphenols from the Green Alga Cladophora socialis. The Journal of Organic Chemistry, 84 (9). pp. 5035-5045. ISSN 0022-3263

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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.

Item Type: Journal Article
Additional Information: PMID: 30908914
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Technology and Environment (FSTE) > Institute of Applied Science
Depositing User: Fulori Nainoca - Waqairagata
Date Deposited: 07 May 2019 00:52
Last Modified: 07 May 2019 00:52

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