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

TitleMarinocyanins, cytotoxic bromo-phenazinone meroterpenoids from a marine bacterium from the streptomycete Glade MAR4
Publication TypeJournal Article
Year of Publication2017
AuthorsAsolkar R.N, Singh A., Jensen PR, Aalbersberg W., Carte B.K, Feussner K.D, Subramani R., DiPasquale A., Rheingold A.L, Fenical W
JournalTetrahedron
Volume73
Pagination2234-2241
Date Published2017/04
Type of ArticleArticle
ISBN Number0040-4020
Accession NumberWOS:000399630600007
Keywordsagents; Bromophenazinones; discovery; MAR4 actinomycete; Meroterpenoids
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. (C) 2017 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2017.03.003
Short TitleTetrahedron
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