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Article

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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Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Old Aberdeen AB24 3UE, UK
2
Departamento de Biología Marina, Universidad Autónoma de Yucatán, Km. 15.5, Carretera Mérida-Xmatkuil, A.P. 4-116 Itzimná, Mérida 97100, Yucatán, Mexico
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School of Natural Sciences, Faculty of Science and Technology, University of Central Lancashire, Preston PR1 2HE, UK
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Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, Edificio Centro de Desarrollo Farmacéutico y Alimentario, Parque Tecnológico de Ciencias de la Salud, 18016 Granada, Spain
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Centro de Investigacións Científicas Avanzadas (CICA) e Departmento de Química, Facultade de Ciencias, AE CICA-INIBIC, Universidad da Coruña, 15071 A Coruña, Spain
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Marine and Plant Research Laboratory of Ghana, Department of Chemistry, School of Physical and Mathematical Sciences, University of Ghana, Legon-Accra P.O. Box LG 56, Ghana
*
Author to whom correspondence should be addressed.
Academic Editor: Daniela Giordano
Mar. Drugs 2021, 19(6), 325; https://doi.org/10.3390/md19060325
Received: 1 May 2021 / Revised: 28 May 2021 / Accepted: 30 May 2021 / Published: 3 June 2021
(This article belongs to the Special Issue Bioactive Molecules from Extreme Environments II)
Three dermacozines, dermacozines N–P (13), 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. View Full-Text
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 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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MDPI and ACS Style

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

AMA Style

Juhasz B, Pech-Puch D, Tabudravu JN, 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. Marine Drugs. 2021; 19(6):325. https://doi.org/10.3390/md19060325

Chicago/Turabian Style

Juhasz, Bertalan, Dawrin Pech-Puch, Jioji N. Tabudravu, Bastien Cautain, Fernando Reyes, Carlos Jiménez, Kwaku Kyeremeh, and Marcel Jaspars. 2021. "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" Marine Drugs 19, no. 6: 325. https://doi.org/10.3390/md19060325

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