Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment.
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 IC(50) values of 9 and 7 microM, respectively, while the highest radical scavenger activity was observed for dermacozine C (3) with an IC(50) value of 8.4 microM.
Abdel-Mageed
Wael M
WM
Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen, Scotland, UK AB24 3UE.
Milne
Bruce F
BF
Wagner
Marcell
M
Schumacher
Marc
M
Sandor
Peter
P
Pathom-aree
Wasu
W
Goodfellow
Michael
M
Bull
Alan T
AT
Horikoshi
Koki
K
Ebel
Rainer
R
Diederich
Marc
M
Fiedler
Hans-Peter
HP
Jaspars
Marcel
M
D000192:Actinomycetales / Q000737:chemistry* / Q000378:metabolism; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D019015:Geologic Sediments / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D020014:K562 Cells; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010140:Pacific Ocean; D010619:Phenazines / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D010858:Pigmentation
D000970:Antineoplastic Agents; D016166:Free Radical Scavengers; D010619:Phenazines