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
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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 1.1ᵀAutor(es)
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2021-06-03Cita bibliográfica
Juhasz, B.; Pech-Puch, D.; Tabudravu, J.N.; Cautain, B.; Reyes, F.; Jiménez, C.; Kyeremeh, K.; Jaspars, M. 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. Mar. Drugs 2021, 19, 325. https://doi.org/10.3390/md19060325
Resumen
[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.
Palabras clave
Deep sea natural products
Mariana Trench
Dermacoccus abyssi MT 1.1ᵀ
¹³C-NMR chemical shift linear and multiple regression
(DFT)-UV-Vis spectral calculation
Phenoxazine
Dermacozine
Absorption maxima in the near infrared region
Mariana Trench
Dermacoccus abyssi MT 1.1ᵀ
¹³C-NMR chemical shift linear and multiple regression
(DFT)-UV-Vis spectral calculation
Phenoxazine
Dermacozine
Absorption maxima in the near infrared region
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Atribución 4.0 Internacional (CC BY 4.0)
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1660-3397