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Bioorganic & Medicinal Chemistry Letters
Vol. 27 (22), 2017, Pages: 4970-4974

Antibacterial activities of viriditoxin congeners and synthetic analogues against fish pathogens

Tae Hwan Noh, Liu Sen, Jongki Hong, Joon-Hee Lee, Hyung Ryong Moon, Jee H.Jung

College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea.

Abstract

Viriditoxin is a fungal secondary metabolite of the fungus Paecilomyces variotii derived from the inner tissues of the giant jellyfish Nemopilema nomurai. Viriditoxin exhibits antibacterial activity against Streptococcus iniae and Streptococcus parauberis, which are major pathogens of aqua cultured fish. Viriditoxin induced abnormal cell morphologies in the fish pathogens S. iniae and S. parauberis, presumably by inhibiting FtsZ polymerization as was previously observed in Escherichia coli. Synthetic analogues of viriditoxin, designed based on docking simulation results to FtsZ of Staphylococcus aureus, were prepared and compared with viriditoxin for antibacterial activity. Reconstitution of free hydroxyl or carboxyl groups of the methoxyl or methyl ester groups of viriditoxin led to significant reduction of antibacterial activity, implying that the natural molecule is optimized for antibacterial activity to deter bacteria potentially harmful to Paecilomyces.

Graphical abstract

Keywords: Viriditoxin, Antibacterial activity, FtsZ inhibitor, Fish pathogens.

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