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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.

Author information

1
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, La Jolla, CA, 92093-0204, USA.
2
Institute of Applied Sciences, Faculty of Science, Technology and Environment, The University of the South Pacific, Laucala Campus, Private Mail Bag, Suva, Fiji.
3
Department of Biology, College of Engineering, Science & Technology (CEST), School of Science, Dept. of Biology, Fiji National University, Natabua Campus, Lautoka, Fiji.
4
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093, USA.

Abstract

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.

KEYWORDS:

Bromophenazinones; MAR4 actinomycete; Meroterpenoids

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