Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species: novel inhibitors of protein kinases

Gernot Brauers, Ruangelie Edrada-Ebel, Rainer Ebel, Peter Proksch, Victor Wray, Albrecht Berg, Udo Gräfe, Christoph Schächtele, Frank Totzke, Gunter Finkenzeller, Dieter Marme, Jurgen Kraus, Miriam Münchbach, Manuela Michel, Gerhard Bringmann, Karsten Schaumann

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

An undescribed fungus of the genus Microsphaeropsis, isolated from the Mediterranean sponge Aplysina aerophoba, produces two new betaenone derivatives (1, 2) and three new 1,3,6, 8-tetrahydroxyanthraquinone congeners (5-7). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data and by CD spectroscopy. This is the first report wherein the (1)H and (13)C NMR data of the betaenone congeners are fully and unambiguously assigned on the basis of two-dimensional NMR spectroscopy. Furthermore, we describe the first elucidation of the absolute configuration of 1-(2'-anthraquinonyl)ethanols such as 5 and 6, by quantum chemical calculation of their circular dichroism (CD) and comparison with experimentally measured spectra. Moreover, it was shown that compounds 1, 5, 6, and 7 are inhibitors of PKC-epsilon, CDK4, and EGF receptor tyrosine kinases.

LanguageEnglish
Pages739-745
Number of pages7
JournalJournal of Natural Products
Volume63
Issue number6
DOIs
Publication statusPublished - Jun 2000

Fingerprint

Anthraquinones
Porifera
Protein Kinase Inhibitors
Circular Dichroism
Fungi
Nuclear magnetic resonance
Protein Kinase C-epsilon
Circular dichroism spectroscopy
Derivatives
Epidermal Growth Factor Receptor
Protein-Tyrosine Kinases
Nuclear magnetic resonance spectroscopy
Spectrum Analysis
Ethanol
Magnetic Resonance Spectroscopy
1,3,6,8-tetrahydroxyanthraquinone

Keywords

  • animals
  • anthraquinones
  • circular dichroism
  • enzyme inhibitors
  • ketones
  • magnetic resonance spectroscopy
  • mass spectrometry
  • mitosporic fungi
  • naphthols
  • porifera
  • protein conformation
  • protein kinase inhibitors

Cite this

Brauers, Gernot ; Edrada-Ebel, Ruangelie ; Ebel, Rainer ; Proksch, Peter ; Wray, Victor ; Berg, Albrecht ; Gräfe, Udo ; Schächtele, Christoph ; Totzke, Frank ; Finkenzeller, Gunter ; Marme, Dieter ; Kraus, Jurgen ; Münchbach, Miriam ; Michel, Manuela ; Bringmann, Gerhard ; Schaumann, Karsten. / Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species : novel inhibitors of protein kinases. In: Journal of Natural Products. 2000 ; Vol. 63, No. 6. pp. 739-745.
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abstract = "An undescribed fungus of the genus Microsphaeropsis, isolated from the Mediterranean sponge Aplysina aerophoba, produces two new betaenone derivatives (1, 2) and three new 1,3,6, 8-tetrahydroxyanthraquinone congeners (5-7). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data and by CD spectroscopy. This is the first report wherein the (1)H and (13)C NMR data of the betaenone congeners are fully and unambiguously assigned on the basis of two-dimensional NMR spectroscopy. Furthermore, we describe the first elucidation of the absolute configuration of 1-(2'-anthraquinonyl)ethanols such as 5 and 6, by quantum chemical calculation of their circular dichroism (CD) and comparison with experimentally measured spectra. Moreover, it was shown that compounds 1, 5, 6, and 7 are inhibitors of PKC-epsilon, CDK4, and EGF receptor tyrosine kinases.",
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Brauers, G, Edrada-Ebel, R, Ebel, R, Proksch, P, Wray, V, Berg, A, Gräfe, U, Schächtele, C, Totzke, F, Finkenzeller, G, Marme, D, Kraus, J, Münchbach, M, Michel, M, Bringmann, G & Schaumann, K 2000, 'Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species: novel inhibitors of protein kinases' Journal of Natural Products, vol. 63, no. 6, pp. 739-745. https://doi.org/10.1021/np9905259

Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species : novel inhibitors of protein kinases. / Brauers, Gernot; Edrada-Ebel, Ruangelie; Ebel, Rainer; Proksch, Peter; Wray, Victor; Berg, Albrecht; Gräfe, Udo; Schächtele, Christoph; Totzke, Frank; Finkenzeller, Gunter; Marme, Dieter; Kraus, Jurgen; Münchbach, Miriam; Michel, Manuela; Bringmann, Gerhard; Schaumann, Karsten.

In: Journal of Natural Products, Vol. 63, No. 6, 06.2000, p. 739-745.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Anthraquinones and betaenone derivatives from the sponge-associated fungus Microsphaeropsis species

T2 - Journal of Natural Products

AU - Brauers, Gernot

AU - Edrada-Ebel, Ruangelie

AU - Ebel, Rainer

AU - Proksch, Peter

AU - Wray, Victor

AU - Berg, Albrecht

AU - Gräfe, Udo

AU - Schächtele, Christoph

AU - Totzke, Frank

AU - Finkenzeller, Gunter

AU - Marme, Dieter

AU - Kraus, Jurgen

AU - Münchbach, Miriam

AU - Michel, Manuela

AU - Bringmann, Gerhard

AU - Schaumann, Karsten

PY - 2000/6

Y1 - 2000/6

N2 - An undescribed fungus of the genus Microsphaeropsis, isolated from the Mediterranean sponge Aplysina aerophoba, produces two new betaenone derivatives (1, 2) and three new 1,3,6, 8-tetrahydroxyanthraquinone congeners (5-7). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data and by CD spectroscopy. This is the first report wherein the (1)H and (13)C NMR data of the betaenone congeners are fully and unambiguously assigned on the basis of two-dimensional NMR spectroscopy. Furthermore, we describe the first elucidation of the absolute configuration of 1-(2'-anthraquinonyl)ethanols such as 5 and 6, by quantum chemical calculation of their circular dichroism (CD) and comparison with experimentally measured spectra. Moreover, it was shown that compounds 1, 5, 6, and 7 are inhibitors of PKC-epsilon, CDK4, and EGF receptor tyrosine kinases.

AB - An undescribed fungus of the genus Microsphaeropsis, isolated from the Mediterranean sponge Aplysina aerophoba, produces two new betaenone derivatives (1, 2) and three new 1,3,6, 8-tetrahydroxyanthraquinone congeners (5-7). The structures of the compounds were established on the basis of NMR spectroscopic and mass spectrometric data and by CD spectroscopy. This is the first report wherein the (1)H and (13)C NMR data of the betaenone congeners are fully and unambiguously assigned on the basis of two-dimensional NMR spectroscopy. Furthermore, we describe the first elucidation of the absolute configuration of 1-(2'-anthraquinonyl)ethanols such as 5 and 6, by quantum chemical calculation of their circular dichroism (CD) and comparison with experimentally measured spectra. Moreover, it was shown that compounds 1, 5, 6, and 7 are inhibitors of PKC-epsilon, CDK4, and EGF receptor tyrosine kinases.

KW - animals

KW - anthraquinones

KW - circular dichroism

KW - enzyme inhibitors

KW - ketones

KW - magnetic resonance spectroscopy

KW - mass spectrometry

KW - mitosporic fungi

KW - naphthols

KW - porifera

KW - protein conformation

KW - protein kinase inhibitors

U2 - 10.1021/np9905259

DO - 10.1021/np9905259

M3 - Article

VL - 63

SP - 739

EP - 745

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 6

ER -