title: Structure and absolute configuration of the fungal ansabenzoquinone rhizopogone.
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).
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universitat Munchen, Butenandtstrasse 5-13, 81377 Munchen, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Lang
authors.forename: Erhard
authors.initials: E
authors.lastname: Jägers
authors.forename: Kurt
authors.initials: K
authors.lastname: Polborn
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Steglich
mesh_terms: D001317:Austria; D001487:Basidiomycota / Q000737:chemistry*; D016227:Benzoquinones / Q000737:chemistry* / Q000302:isolation & purification*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010860:Pigments, Biological / Q000737:chemistry* / Q000302:isolation & purification*
chemical_list: D016227:Benzoquinones; D010860:Pigments, Biological; C550236:rhizopogone