Structure and absolute configuration of the fungal ansabenzoquinone rhizopogone

J Nat Prod. 2009 Feb 27;72(2):214-7. doi: 10.1021/np8007073.

Abstract

The main pigment of the basidiomycete Rhizopogon pumilionus is the [13]paracyclophane derivative rhizopogone (1). The structures of 1 and the accompanying 2-acetoxyrhizopogone (5) were determined by spectroscopic studies, including 1D and 2D NMR measurements. The absolute configuration of 1 was assigned by comparison of its CD spectrum with that of secotridentoquinone (4). The structures of 1 and tridentoquinone (3) suggest a common biosynthesis originating from 2-geranylgeranyl-6-hydroxy-1,4-benzoquinone (9). This supports the close taxonomic relationship of the genera Rhizopogon and Suillus (Boletales).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Austria
  • Basidiomycota / chemistry*
  • Benzoquinones / chemistry*
  • Benzoquinones / isolation & purification*
  • Circular Dichroism
  • Crystallography, X-Ray
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pigments, Biological / chemistry*
  • Pigments, Biological / isolation & purification*

Substances

  • Benzoquinones
  • Pigments, Biological
  • rhizopogone