SCIENCE@home

Antibacterial Oligomeric Polyphenols from the Green Alga Cladophora socialis

S. Lavoie,A. M. Sweeney-Jones,Nazia Mojib,Brandon Dale,Kerstin Gagaring,C. McNamara,C. Quave,K. Soapi,J. Kubanek

Published 2019 in Journal of Organic Chemistry

ABSTRACT

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.

PUBLICATION RECORD

CITATION MAP

EXTRACTION MAP

CLAIMS

  • No claims are published for this paper.

CONCEPTS

  • No concepts are published for this paper.

REFERENCES

Showing 1-33 of 33 references · Page 1 of 1

CITED BY

Showing 1-23 of 23 citing papers · Page 1 of 1