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Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment

Lookup NU author(s): Wael Abdel-Mageed, Marcell Wagner, Dr Marc Schumacher, Wasu Pathom-Aree, Professor Michael Goodfellow, Professor Alan Bull


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Dermacoccus abyssi sp. nov., strains MT1.1 and MT1.2 are actinomycetes isolated from Mariana Trench sediment at a depth of 10 898 m. Fermentation using ISP2 and 410 media, respectively, lead to production of seven new oxidized and reduced phenazine-type pigments, dermacozines A-G (1-7), together with the known phenazine-1-carboxylic acid (8) and phenazine-1,6-dicarboxylic acid (9). Extensive use was made of 1D and 2D-NMR data, and high resolution MS to determine the structures of the compounds. To confirm the structure of the most complex pentacyclic analogue (5) we made use of electronic structure calculations to compare experimental and theoretical UV-Vis spectra, which confirmed a novel structural class of phenazine derivatives, the dermacozines. The absolute stereochemistry of dermacozine D (4) was determined as S by a combination of CD spectroscopy and electronic structure calculations. Dermacozines F (6) and G (7) exhibited moderate cytotoxic activity against leukaemia cell line K562 with IC50 values of 9 and 7 mu M, respectively, while the highest radical scavenger activity was observed for dermacozine C (3) with an IC50 value of 8.4 mu M.

Publication metadata

Author(s): Abdel-Mageed WM, Milne BF, Wagner M, Schumacher M, Sandor P, Pathom-Aree W, Goodfellow M, Bull AT, Horikoshi K, Ebel R, Diederich M, Fiedler HP, Jaspars M

Publication type: Article

Publication status: Published

Journal: Organic & Biomolecular Chemistry

Year: 2010

Volume: 8

Issue: 10

Pages: 2352-2362

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry


DOI: 10.1039/c001445a


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Funder referenceFunder name
"Een Haerz fur kriibskrank Kanner" asbl
"Recherches Scientifiques Luxembourg (RSL)" association
Action Lions Vaincre le Cancer
Scottish Government Rural and Environment Research and Analysis Directorate at the University of Aberdeen Rowett Institute of Nutrition and Health, Scotland
"Recherche Cancer et Sang" foundation
Egyptian Government
Leverhulme Trust
PTDC/FIS/73578/2006Portuguese Foundation for Science and Technology