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

doi:10.3390/md19060325

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 language	English
Article number	e325
Number of pages	22
Journal	Marine Drugs
Volume	19
Issue number	6
DOIs	https://doi.org/10.3390/md19060325
Publication status	Published - 3 Jun 2021

Bibliographical note

Funding: Dawrin Pech-Puch received his postdoctoral fellowship from the National Council of Science and Technology (CONACYT) of Mexico.

Acknowledgments: The authors wish to express their thanks to Michael Goodfellow, School of Nat- ural and Environmental Sciences, Newcastle University for providing the pure colony of Dermacoccus abyssi MT 1.1T, to Wasu Pathom-Aree (Chiang Mai University, Thailand), who isolated the strain fur- thermore to the Kaiko operation team and the crew of M.S. Yokosuka, JAMSTEC, Yokosuka, Japan, for the sediment collection. The authors thank and acknowledge the significant contribution of John W. Still—SEM Specialist, ACEMAC Facility, The University of Aberdeen; Lucinda Wight—Microscope and Histology Specialist, School of Medicine, Medical Sciences and Nutrition, The University of Aberdeen for preparing the strain Dermacoccus abyssi MT 1.1T for EM imaging; Russel Gray for NMR measurements—The University of Aberdeen, Department of Chemistry, Marine Biodiscovery Centre, NMR Laboratory; Bella Juraj for NMR measurements—The University of Edinburgh, Joseph Black Building, School of Chemistry, NMR Laboratory. Marcel Jaspars and Bertalan Juhasz acknowledge the help of the University of Edinburgh through the EPSR Grant: EP/R030065/1 for the 800 MHz NMR measurements with the 5 mm TCI He Cryoprobe of compounds 1 and 2. Carlos Jimenéz and Dawrin Pech-Puch acknowledge the help of CESGA for the computational support. Bertalan Juhasz wishes to express his sincere gratitude to his supervisor, Marcel Jaspars, for his invaluable trust and support.

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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Juhasz, B., Pech-Puch, D., Tabudravu, J. N., Cautain, B., Reyes, F., Jiménez, C., Kyeremeh, K., & Jaspars, M. (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 1.1 T. Marine Drugs, 19(6), Article e325. https://doi.org/10.3390/md19060325

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. / Juhasz, Bertalan; Pech-Puch, Dawrin; Tabudravu, Jioji N. et al.
In: Marine Drugs, Vol. 19, No. 6, e325, 03.06.2021.

Research output: Contribution to journal › Article › peer-review

Juhasz, B, Pech-Puch, D, Tabudravu, JN, Cautain, B, Reyes, F, Jiménez, C, Kyeremeh, K & Jaspars, M 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 1.1 T', Marine Drugs, vol. 19, no. 6, e325. https://doi.org/10.3390/md19060325

Juhasz B, Pech-Puch D, Tabudravu JN, Cautain B, Reyes F, Jiménez C et al. 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. Marine Drugs. 2021 Jun 3;19(6):e325. doi: 10.3390/md19060325

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title = "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",

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.",

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",

author = "Bertalan Juhasz and Dawrin Pech-Puch and Tabudravu, {Jioji N.} and Bastien Cautain and Fernando Reyes and Carlos Jim{\'e}nez and Kwaku Kyeremeh and Marcel Jaspars",

note = "Funding: Dawrin Pech-Puch received his postdoctoral fellowship from the National Council of Science and Technology (CONACYT) of Mexico. Acknowledgments: The authors wish to express their thanks to Michael Goodfellow, School of Nat- ural and Environmental Sciences, Newcastle University for providing the pure colony of Dermacoccus abyssi MT 1.1T, to Wasu Pathom-Aree (Chiang Mai University, Thailand), who isolated the strain fur- thermore to the Kaiko operation team and the crew of M.S. Yokosuka, JAMSTEC, Yokosuka, Japan, for the sediment collection. The authors thank and acknowledge the significant contribution of John W. Still—SEM Specialist, ACEMAC Facility, The University of Aberdeen; Lucinda Wight—Microscope and Histology Specialist, School of Medicine, Medical Sciences and Nutrition, The University of Aberdeen for preparing the strain Dermacoccus abyssi MT 1.1T for EM imaging; Russel Gray for NMR measurements—The University of Aberdeen, Department of Chemistry, Marine Biodiscovery Centre, NMR Laboratory; Bella Juraj for NMR measurements—The University of Edinburgh, Joseph Black Building, School of Chemistry, NMR Laboratory. Marcel Jaspars and Bertalan Juhasz acknowledge the help of the University of Edinburgh through the EPSR Grant: EP/R030065/1 for the 800 MHz NMR measurements with the 5 mm TCI He Cryoprobe of compounds 1 and 2. Carlos Jimen{\'e}z and Dawrin Pech-Puch acknowledge the help of CESGA for the computational support. Bertalan Juhasz wishes to express his sincere gratitude to his supervisor, Marcel Jaspars, for his invaluable trust and support. ",

year = "2021",

month = jun,

day = "3",

doi = "10.3390/md19060325",

language = "English",

volume = "19",

journal = "Marine Drugs",

issn = "1660-3397",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "6",

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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 1.1 T

AU - Juhasz, Bertalan

AU - Pech-Puch, Dawrin

AU - Tabudravu, Jioji N.

AU - Cautain, Bastien

AU - Reyes, Fernando

AU - Jiménez, Carlos

AU - Kyeremeh, Kwaku

AU - Jaspars, Marcel

N1 - Funding: Dawrin Pech-Puch received his postdoctoral fellowship from the National Council of Science and Technology (CONACYT) of Mexico. Acknowledgments: The authors wish to express their thanks to Michael Goodfellow, School of Nat- ural and Environmental Sciences, Newcastle University for providing the pure colony of Dermacoccus abyssi MT 1.1T, to Wasu Pathom-Aree (Chiang Mai University, Thailand), who isolated the strain fur- thermore to the Kaiko operation team and the crew of M.S. Yokosuka, JAMSTEC, Yokosuka, Japan, for the sediment collection. The authors thank and acknowledge the significant contribution of John W. Still—SEM Specialist, ACEMAC Facility, The University of Aberdeen; Lucinda Wight—Microscope and Histology Specialist, School of Medicine, Medical Sciences and Nutrition, The University of Aberdeen for preparing the strain Dermacoccus abyssi MT 1.1T for EM imaging; Russel Gray for NMR measurements—The University of Aberdeen, Department of Chemistry, Marine Biodiscovery Centre, NMR Laboratory; Bella Juraj for NMR measurements—The University of Edinburgh, Joseph Black Building, School of Chemistry, NMR Laboratory. Marcel Jaspars and Bertalan Juhasz acknowledge the help of the University of Edinburgh through the EPSR Grant: EP/R030065/1 for the 800 MHz NMR measurements with the 5 mm TCI He Cryoprobe of compounds 1 and 2. Carlos Jimenéz and Dawrin Pech-Puch acknowledge the help of CESGA for the computational support. Bertalan Juhasz wishes to express his sincere gratitude to his supervisor, Marcel Jaspars, for his invaluable trust and support.

PY - 2021/6/3

Y1 - 2021/6/3

N2 - 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.

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.

KW - deep sea natural products

KW - Mariana Trench

KW - Dermacoccus abyssi MT 1.1T

KW - 13C-NMR chemical shift linear and multiple regression

KW - (DFT)-UV-Vis spectral calculation

KW - phenoxazine

KW - dermacozine

KW - absorption maxima in the near infrared region

U2 - 10.3390/md19060325

DO - 10.3390/md19060325

M3 - Article

SN - 1660-3397

VL - 19

JO - Marine Drugs

JF - Marine Drugs

IS - 6

M1 - e325

ER -

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

Abstract

Bibliographical note

Keywords

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