Dermacozine N, the First Natural Linear Pentacyclic Oxazinophenazine with UV–Vis Absorption Maxima in the Near Infrared Region, along with Dermacozines O and P Isolated from the Mariana Trench Sediment Strain Dermacoccus abyssi MT 1.1T

Abstract

Three dermacozines, dermacozines N–P (1–3), were isolated from the piezotolerant Actinomycete strain Dermacoccus abyssi MT 1.1T, which was isolated from a Mariana Trench sediment in 2006. Herein, we report the elucidation of their structures using a combination of 1D/2D NMR, LC-HRESI-MSn, UV–Visible, and IR spectroscopy. Further confirmation of the structures was achieved through the analysis of data from density functional theory (DFT)–UV–Visible spectral calculations and statistical analysis such as two tailed t-test, linear regression-, and multiple linear regression analysis applied to either solely experimental or to experimental and calculated 13C-NMR chemical shift data. Dermacozine N (1) bears a novel linear pentacyclic phenoxazine framework that has never been reported as a natural product. Dermacozine O (2) is a constitutional isomer of the known dermacozine F while dermacozine P (3) is 8-benzoyl-6-carbamoylphenazine-1-carboxylic acid. Dermacozine N (1) is unique among phenoxazines due to its near infrared (NIR) absorption maxima, which would make this compound an excellent candidate for research in biosensing chemistry, photodynamic therapy (PDT), opto-electronic applications, and metabolic mapping at the cellular level. Furthermore, dermacozine N (1) possesses weak cytotoxic activity against melanoma (A2058) and hepatocellular carcinoma cells (HepG2) with IC50 values of 51 and 38 μM, respectively.

Marine natural products

“…10 Dermacozines N–P 22 , 23 , 24 , were isolated from a piezotolerant actinomycete strain Dermacoccus abyssi with dermacozine N 22 bearing a novel linear pentacyclic phenoxazine motif. 11 Genome mining of Fulvivirga sp. revealed a desferrioxamine-like BGC that contained an unknown gene fulF that is conserved in many Bacteroidetes species.…”

The dermacozines and light: a novel phenazine semiquinone radical based photocatalytic system from the deepest oceanic trench of the Earth

“…In this process the electronic core phenazine structure is modified by the bacterium suggestive of compounds with differing redox properties. [2][3][4][5] To investigate this, we recorded CVs of test compounds isolated from the medium of Dermacoccus abyssi MT1.1 T (dermacozines B, E, F, O, P and phenazine-1-carboxylic acid (PCA)) in a suit-able electrolyte (0.1 M NaClO 4 in acetonitrile) [ESI S5-10 † and Table 1].…”

“…The in vivo function of these compounds is unknown, but it has been suggested that due to their range of UV-Vis absorbances, structural properties and radical scavenging activity they may participate in electron shuttling reactions. [2][3][4][5] Reports on phenazines participating in reducing matter (e.g., O 2 /O 2…”

Structural and Biological Insights into the Hot‐Spot Marine Natural Products Reported from 2012 to 2021

“…[ 23 ] Dermacozine N ( 12 ), the first natural linear pentacyclic oxazinophenazinea found in nature, was obtained from a Mariana Trench sediment‐derived Dermacoccus abyssi (Figure 2). [ 24 ]…”