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 1.1 T

Bertalan Juhasz, Dawrin Pech-Puch, Jioji N. Tabudravu, Bastien Cautain, Fernando Reyes, Carlos Jiménez, Kwaku Kyeremeh, Marcel Jaspars*

*Corresponding author for this work

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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.
Original languageEnglish
Article numbere325
Number of pages22
JournalMarine Drugs
Volume19
Issue number6
DOIs
Publication statusPublished - 3 Jun 2021

Keywords

  • 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

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