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Tetrahedron. 2017 Apr 20;73(16):2234-2241. doi: 10.1016/j.tet.2017.03.003. Epub 2017 Mar 6.

Marinocyanins, cytotoxic bromo-phenazinone meroterpenoids from a marine bacterium from the streptomycete clade MAR4.

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Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, La Jolla, CA, 92093-0204, USA.
Institute of Applied Sciences, Faculty of Science, Technology and Environment, The University of the South Pacific, Laucala Campus, Private Mail Bag, Suva, Fiji.
Department of Biology, College of Engineering, Science & Technology (CEST), School of Science, Dept. of Biology, Fiji National University, Natabua Campus, Lautoka, Fiji.
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093, USA.


Six cytotoxic and antimicrobial metabolites of a new bromo-phenazinone class, the marinocyanins A-F (1-6), were isolated together with the known bacterial metabolites 2-bromo-1-hydroxyphenazine (7), lavanducyanin (8, WS-9659A) and its chlorinated analog WS-9659B (9). These metabolites were purified by bioassay-guided fractionation of the extracts of our MAR4 marine actinomycete strains CNS-284 and CNY-960. The structures of the new compounds were determined by detailed spectroscopic methods and marinocyanin A (1) was confirmed by crystallographic methods. The marinocyanins represent the first bromo-phenazinones with an N-isoprenoid substituent in the skeleton. Marinocyanins A-F show strong to weak cytotoxicity against HCT-116 human colon carcinoma and possess modest antimicrobial activities against Staphylococcus aureus and amphotericin-resistant Candida albicans.


Bromophenazinones; MAR4 actinomycete; Meroterpenoids

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