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Mar. Drugs 2014, 12(2), 940-963; doi:10.3390/md12020940
Article

Antimicrobial Activity of the Marine Alkaloids, Clathrodin and Oroidin, and Their Synthetic Analogues

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Received: 25 November 2013; in revised form: 17 January 2014 / Accepted: 23 January 2014 / Published: 14 February 2014
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Abstract: Marine organisms produce secondary metabolites that may be valuable for the development of novel drug leads as such and can also provide structural scaffolds for the design and synthesis of novel bioactive compounds. The marine alkaloids, clathrodin and oroidin, which were originally isolated from sponges of the genus, Agelas, were prepared and evaluated for their antimicrobial activity against three bacterial strains (Enterococcus faecalis, Staphylococcus aureus and Escherichia coli) and one fungal strain (Candida albicans), and oroidin was found to possess promising Gram-positive antibacterial activity. Using oroidin as a scaffold, 34 new analogues were designed, prepared and screened for their antimicrobial properties. Of these compounds, 12 exhibited >80% inhibition of the growth of at least one microorganism at a concentration of 50 µM. The most active derivative was found to be 4-phenyl-2-aminoimidazole 6h, which exhibited MIC90 (minimum inhibitory concentration) values of 12.5 µM against the Gram-positive bacteria and 50 µM against E. coli. The selectivity index between S. aureus and mammalian cells, which is important to consider in the evaluation of a compound’s potential as an antimicrobial lead, was found to be 2.9 for compound 6h.
Keywords: marine alkaloid; Agelas; antimicrobial; antibacterial; antifungal; pyrrole-2-aminoimidazole; oroidin; clathrodin marine alkaloid; Agelas; antimicrobial; antibacterial; antifungal; pyrrole-2-aminoimidazole; oroidin; clathrodin
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Zidar, N.; Montalvão, S.; Hodnik, Ž.; Nawrot, D.A.; Žula, A.; Ilaš, J.; Kikelj, D.; Tammela, P.; Mašič, L.P. Antimicrobial Activity of the Marine Alkaloids, Clathrodin and Oroidin, and Their Synthetic Analogues. Mar. Drugs 2014, 12, 940-963.

AMA Style

Zidar N, Montalvão S, Hodnik Ž, Nawrot DA, Žula A, Ilaš J, Kikelj D, Tammela P, Mašič LP. Antimicrobial Activity of the Marine Alkaloids, Clathrodin and Oroidin, and Their Synthetic Analogues. Marine Drugs. 2014; 12(2):940-963.

Chicago/Turabian Style

Zidar, Nace; Montalvão, Sofia; Hodnik, Žiga; Nawrot, Dorota A.; Žula, Aleš; Ilaš, Janez; Kikelj, Danijel; Tammela, Päivi; Mašič, Lucija P. 2014. "Antimicrobial Activity of the Marine Alkaloids, Clathrodin and Oroidin, and Their Synthetic Analogues." Mar. Drugs 12, no. 2: 940-963.



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