RT Journal Article
T1 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.
A1 Juhasz, Bertalan
A1 Pech-Puch, Dawrin
A1 Tabudravu, Jioji N
A1 Cautain, Bastien
A1 Reyes, Fernando
A1 Jiménez, Carlos
A1 Kyeremeh, Kwaku
A1 Jaspars, Marcel
K1 (DFT)-UV-Vis spectral calculation
K1 13C-NMR chemical shift linear and multiple regression
K1 Dermacoccus abyssi MT 1.1T
K1 Mariana Trench
K1 absorption maxima in the near infrared region
K1 deep sea natural products
K1 dermacozine
K1 phenoxazine
AB 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.
YR 2021
FD 2021-06-03
LK http://hdl.handle.net/10668/18104
UL http://hdl.handle.net/10668/18104
LA en
DS RISalud
RD Apr 15, 2025