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

Wael M. Abdel-Mageed, Bruce Forbes Milne, Marcell Wagner, Marc Schumacher, Peter Sandor, Wasu Pathom-aree, Michael Goodfellow, Alan T. Bull, Koki Horikoshi, Rainer Peter Ebel, Marc Diederich, Hans-Peter Fiedler, Marcel Jaspars

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Abstract

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.

Original languageEnglish
Pages (from-to)2352-2362
Number of pages11
JournalOrganic & Biomolecular Chemistry
Volume8
Issue number10
Early online date18 Mar 2010
DOIs
Publication statusPublished - 2010

Keywords

  • radical-scavenging activity
  • marine natural-products
  • approxmate coulomb potentials
  • auxiliary basis-set
  • Gaussin-basis sets
  • phenazine-1,6-dicarboxylic acid
  • phenazine-1-carboxylic acid
  • pseudomonas-fluorescens
  • secondary metabolites
  • biosynthetic-pathway

Cite this

Abdel-Mageed, W. M., Milne, B. F., Wagner, M., Schumacher, M., Sandor, P., Pathom-aree, W., Goodfellow, M., Bull, A. T., Horikoshi, K., Ebel, R. P., Diederich, M., Fiedler, H-P., & Jaspars, M. (2010). Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment. Organic & Biomolecular Chemistry, 8(10), 2352-2362. https://doi.org/10.1039/c001445a