Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment

Wael M. Abdel-Mageed, Bruce Forbes Milne, Marcell Wagner, Marc Schumacher, Peter Sandor, Wasu Pathom-aree, Michael Goodfellow, Alan T. Bull, Koki Horikoshi, Rainer Peter Ebel, Marc Diederich, Hans-Peter Fiedler, Marcel Jaspars

Research output: Contribution to journalArticle

74 Citations (Scopus)

Abstract

Dermacoccus abyssi sp. nov., strains MT1.1 and MT1.2 are actinomycetes isolated from Mariana Trench sediment at a depth of 10 898 m. Fermentation using ISP2 and 410 media, respectively, lead to production of seven new oxidized and reduced phenazine-type pigments, dermacozines A-G (1-7), together with the known phenazine-1-carboxylic acid (8) and phenazine-1,6-dicarboxylic acid (9). Extensive use was made of 1D and 2D-NMR data, and high resolution MS to determine the structures of the compounds. To confirm the structure of the most complex pentacyclic analogue (5) we made use of electronic structure calculations to compare experimental and theoretical UV-Vis spectra, which confirmed a novel structural class of phenazine derivatives, the dermacozines. The absolute stereochemistry of dermacozine D (4) was determined as S by a combination of CD spectroscopy and electronic structure calculations. Dermacozines F (6) and G (7) exhibited moderate cytotoxic activity against leukaemia cell line K562 with IC50 values of 9 and 7 mu M, respectively, while the highest radical scavenger activity was observed for dermacozine C (3) with an IC50 value of 8.4 mu M.

Original languageEnglish
Pages (from-to)2352-2362
Number of pages11
JournalOrganic & Biomolecular Chemistry
Volume8
Issue number10
Early online date18 Mar 2010
DOIs
Publication statusPublished - 2010

Keywords

  • radical-scavenging activity
  • marine natural-products
  • approxmate coulomb potentials
  • auxiliary basis-set
  • Gaussin-basis sets
  • phenazine-1,6-dicarboxylic acid
  • phenazine-1-carboxylic acid
  • pseudomonas-fluorescens
  • secondary metabolites
  • biosynthetic-pathway

Cite this

Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment. / Abdel-Mageed, Wael M.; Milne, Bruce Forbes; Wagner, Marcell; Schumacher, Marc; Sandor, Peter; Pathom-aree, Wasu; Goodfellow, Michael; Bull, Alan T.; Horikoshi, Koki; Ebel, Rainer Peter; Diederich, Marc; Fiedler, Hans-Peter; Jaspars, Marcel.

In: Organic & Biomolecular Chemistry, Vol. 8, No. 10, 2010, p. 2352-2362.

Research output: Contribution to journalArticle

Abdel-Mageed, WM, Milne, BF, Wagner, M, Schumacher, M, Sandor, P, Pathom-aree, W, Goodfellow, M, Bull, AT, Horikoshi, K, Ebel, RP, Diederich, M, Fiedler, H-P & Jaspars, M 2010, 'Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment', Organic & Biomolecular Chemistry, vol. 8, no. 10, pp. 2352-2362. https://doi.org/10.1039/c001445a
Abdel-Mageed, Wael M. ; Milne, Bruce Forbes ; Wagner, Marcell ; Schumacher, Marc ; Sandor, Peter ; Pathom-aree, Wasu ; Goodfellow, Michael ; Bull, Alan T. ; Horikoshi, Koki ; Ebel, Rainer Peter ; Diederich, Marc ; Fiedler, Hans-Peter ; Jaspars, Marcel. / Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment. In: Organic & Biomolecular Chemistry. 2010 ; Vol. 8, No. 10. pp. 2352-2362.
@article{aac865c1d3fc41ccb95f246bc4142e65,
title = "Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment",
abstract = "Dermacoccus abyssi sp. nov., strains MT1.1 and MT1.2 are actinomycetes isolated from Mariana Trench sediment at a depth of 10 898 m. Fermentation using ISP2 and 410 media, respectively, lead to production of seven new oxidized and reduced phenazine-type pigments, dermacozines A-G (1-7), together with the known phenazine-1-carboxylic acid (8) and phenazine-1,6-dicarboxylic acid (9). Extensive use was made of 1D and 2D-NMR data, and high resolution MS to determine the structures of the compounds. To confirm the structure of the most complex pentacyclic analogue (5) we made use of electronic structure calculations to compare experimental and theoretical UV-Vis spectra, which confirmed a novel structural class of phenazine derivatives, the dermacozines. The absolute stereochemistry of dermacozine D (4) was determined as S by a combination of CD spectroscopy and electronic structure calculations. Dermacozines F (6) and G (7) exhibited moderate cytotoxic activity against leukaemia cell line K562 with IC50 values of 9 and 7 mu M, respectively, while the highest radical scavenger activity was observed for dermacozine C (3) with an IC50 value of 8.4 mu M.",
keywords = "radical-scavenging activity, marine natural-products, approxmate coulomb potentials, auxiliary basis-set, Gaussin-basis sets, phenazine-1,6-dicarboxylic acid, phenazine-1-carboxylic acid, pseudomonas-fluorescens, secondary metabolites, biosynthetic-pathway",
author = "Abdel-Mageed, {Wael M.} and Milne, {Bruce Forbes} and Marcell Wagner and Marc Schumacher and Peter Sandor and Wasu Pathom-aree and Michael Goodfellow and Bull, {Alan T.} and Koki Horikoshi and Ebel, {Rainer Peter} and Marc Diederich and Hans-Peter Fiedler and Marcel Jaspars",
note = "Acknowledgements The authors are grateful to EPSRC National Mass Spectrometric Centre, University of Wales, Swansea, for mass spectrometric analysis. We also thank Sharon M. Kelly, Institute of Biomedical and Life Sciences, University of Glasgow, for CD measurements. We thank the Kaiko operation team and the crew of M.S. Yokosuka for collecting sediment samples. WMAM thanks the Egyptian Government for a Ph.D. scholarship. ATB thanks the Leverhulme Trust for an Emeritus Fellowship. MJ is the recipient of a BBSRC Research Development Fellowship. This work also was supported in part by the “Recherche Cancer et Sang” foundation, Telˆ evie and the “Recherches Scientifiques Luxembourg (RSL)” ˆ association. MS is supported by a Telˆ evie grant. The authors ˆ thank the “Action Lions Vaincre le Cancer” and “Een Haerz fir ¨ kriibskrank Kanner” asbl for additional support. BFM thanks the Portuguese Foundation for Science and Technology for financial support (PTDC/FIS/73578/2006). All theoretical calculations were performed using the RINH/BioSS Beowulf cluster which is funded by the Scottish Government Rural and Environment Research and Analysis Directorate at the University of Aberdeen Rowett Institute of Nutrition and Health, Scotland with the assistance of Dr Tony Travis.",
year = "2010",
doi = "10.1039/c001445a",
language = "English",
volume = "8",
pages = "2352--2362",
journal = "Organic & Biomolecular Chemistry",
issn = "1477-0520",
publisher = "The Royal Society of Chemistry",
number = "10",

}

TY - JOUR

T1 - Dermacozines, a new phenazine family from deep-sea dermacocci isolated from a Mariana Trench sediment

AU - Abdel-Mageed, Wael M.

AU - Milne, Bruce Forbes

AU - Wagner, Marcell

AU - Schumacher, Marc

AU - Sandor, Peter

AU - Pathom-aree, Wasu

AU - Goodfellow, Michael

AU - Bull, Alan T.

AU - Horikoshi, Koki

AU - Ebel, Rainer Peter

AU - Diederich, Marc

AU - Fiedler, Hans-Peter

AU - Jaspars, Marcel

N1 - Acknowledgements The authors are grateful to EPSRC National Mass Spectrometric Centre, University of Wales, Swansea, for mass spectrometric analysis. We also thank Sharon M. Kelly, Institute of Biomedical and Life Sciences, University of Glasgow, for CD measurements. We thank the Kaiko operation team and the crew of M.S. Yokosuka for collecting sediment samples. WMAM thanks the Egyptian Government for a Ph.D. scholarship. ATB thanks the Leverhulme Trust for an Emeritus Fellowship. MJ is the recipient of a BBSRC Research Development Fellowship. This work also was supported in part by the “Recherche Cancer et Sang” foundation, Telˆ evie and the “Recherches Scientifiques Luxembourg (RSL)” ˆ association. MS is supported by a Telˆ evie grant. The authors ˆ thank the “Action Lions Vaincre le Cancer” and “Een Haerz fir ¨ kriibskrank Kanner” asbl for additional support. BFM thanks the Portuguese Foundation for Science and Technology for financial support (PTDC/FIS/73578/2006). All theoretical calculations were performed using the RINH/BioSS Beowulf cluster which is funded by the Scottish Government Rural and Environment Research and Analysis Directorate at the University of Aberdeen Rowett Institute of Nutrition and Health, Scotland with the assistance of Dr Tony Travis.

PY - 2010

Y1 - 2010

N2 - Dermacoccus abyssi sp. nov., strains MT1.1 and MT1.2 are actinomycetes isolated from Mariana Trench sediment at a depth of 10 898 m. Fermentation using ISP2 and 410 media, respectively, lead to production of seven new oxidized and reduced phenazine-type pigments, dermacozines A-G (1-7), together with the known phenazine-1-carboxylic acid (8) and phenazine-1,6-dicarboxylic acid (9). Extensive use was made of 1D and 2D-NMR data, and high resolution MS to determine the structures of the compounds. To confirm the structure of the most complex pentacyclic analogue (5) we made use of electronic structure calculations to compare experimental and theoretical UV-Vis spectra, which confirmed a novel structural class of phenazine derivatives, the dermacozines. The absolute stereochemistry of dermacozine D (4) was determined as S by a combination of CD spectroscopy and electronic structure calculations. Dermacozines F (6) and G (7) exhibited moderate cytotoxic activity against leukaemia cell line K562 with IC50 values of 9 and 7 mu M, respectively, while the highest radical scavenger activity was observed for dermacozine C (3) with an IC50 value of 8.4 mu M.

AB - Dermacoccus abyssi sp. nov., strains MT1.1 and MT1.2 are actinomycetes isolated from Mariana Trench sediment at a depth of 10 898 m. Fermentation using ISP2 and 410 media, respectively, lead to production of seven new oxidized and reduced phenazine-type pigments, dermacozines A-G (1-7), together with the known phenazine-1-carboxylic acid (8) and phenazine-1,6-dicarboxylic acid (9). Extensive use was made of 1D and 2D-NMR data, and high resolution MS to determine the structures of the compounds. To confirm the structure of the most complex pentacyclic analogue (5) we made use of electronic structure calculations to compare experimental and theoretical UV-Vis spectra, which confirmed a novel structural class of phenazine derivatives, the dermacozines. The absolute stereochemistry of dermacozine D (4) was determined as S by a combination of CD spectroscopy and electronic structure calculations. Dermacozines F (6) and G (7) exhibited moderate cytotoxic activity against leukaemia cell line K562 with IC50 values of 9 and 7 mu M, respectively, while the highest radical scavenger activity was observed for dermacozine C (3) with an IC50 value of 8.4 mu M.

KW - radical-scavenging activity

KW - marine natural-products

KW - approxmate coulomb potentials

KW - auxiliary basis-set

KW - Gaussin-basis sets

KW - phenazine-1,6-dicarboxylic acid

KW - phenazine-1-carboxylic acid

KW - pseudomonas-fluorescens

KW - secondary metabolites

KW - biosynthetic-pathway

U2 - 10.1039/c001445a

DO - 10.1039/c001445a

M3 - Article

VL - 8

SP - 2352

EP - 2362

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 10

ER -