Structure and absolute configuration of the fungal ansabenzoquinone rhizopogone.
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).
Lang
Martin
M
Department Chemie, Ludwig-Maximilians-Universitat Munchen, Butenandtstrasse 5-13, 81377 Munchen, Germany.
Jägers
Erhard
E
Polborn
Kurt
K
Steglich
Wolfgang
W
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*
D016227:Benzoquinones; D010860:Pigments, Biological; C550236:rhizopogone