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

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 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.

Bioactive Secondary Metabolites with Unique Aromatic and Heterocyclic Structures Obtained from Terrestrial Actinomycetes Species

“…This then couples to the C6-C2 building block (i.e., phenylacetic acid) to produce aotaphenazine (20). In the same manner Abdel-Mageed et al 36) proposed a biosynthetic pathway for dermacozines E-G (25-27) possessing very similar structures to aotaphenazine (20).…”

“…IFM 11307 isolated from a soil sample collected from Yoro Valley, Ichihara, Chiba, Japan gave four pyranonaphthoquinones (34)(35)(36). 29) Compound 35 at 0.1 µM significantly overcame TRAIL resistance in AGS cell lines.…”

Ocean Dwelling Actinobacteria as Source of Antitumor Compounds

“…nov., strains MT1.1 and MT1.2, which was derived from Mariana Trench sediment. The compounds exhibited low cytotoxicity against K562 cell line among which highest cytotoxicity was observed for dermacozines F and G with IC50 value of 9 and 7 μM, respectively (Abdel-Mageed et al 2010).…”

Biologically active secondary metabolites from Actinomycetes

“…They show antitumour activity against lung cancer, breast cancer, melanoma and prostate cancer cells [11,75]. Tartrolons, compounds leukaemia cell line K562), antiprotozoal and free radical scavenging activity (Figure 9) [78].…”