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

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61 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.

Original languageEnglish
Pages (from-to)739-745
Number of pages7
JournalJournal of Natural Products
Volume63
Issue number6
DOIs
Publication statusPublished - Jun 2000

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Keywords

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

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