Pigments of Fungi, Part 27. New Xanthorin Derivatives from a Fungus of the Genus Dermocybe

Abstract

The hydroxy lated anthraquinones 2 and 4 were isolated from an indigenous Australian mushroom of the genus Dermocybe, and their structures were established by spectroscopic and chemical methods.Hydroxylated anthraquinones occur in great variety in the fruiting bodies of fungi belonging to the closely related genera Cortinarius and Dermocybe. [The rank of Dermocybe remains a matter for debate. In line with most recent chemical publications (1), and consistent with Moser (2), we have elected to treat Dermocybe as a genus. Other authorities regard Dermocybe as a sub-genus of Cortinarius.] More than thirty pigments of LITERATURE CITED

New Xanthorin Glycosides from a Dermocybe Species

“…A description of the fungus has been published previously. 2 Extraction, Isolation, and Derivatization of Natural Products 3 and 4. Fresh fruiting bodies of Dermocybe sp.…”

“…WAT 22963 (Agaricales). 2 Drawn by the intensity of the pigmentation that remained in the aqueous phase when the total EtOH extract of Dermocybe sp. WAT 22963 was partitioned between EtOAc and H 2 O, the constituents of this fungus were reexamined.…”

“…The deep red organic phase afforded, among other things the xanthorin derivatives 1 and 2, which were identified by direct comparison with authentic materials. 2 A small aliquot of the orange aqueous phase was stirred at room temperature with dilute HCl, and the resulting hydrolysate was extracted with EtOAc. All of the pigments then passed into the organic phase, and the principal components of the extract were separated by preparative silica TLC.…”

“…Earlier we described the isolation and structure elucidation of ω-hydroxyxanthorin 1- O -methyl ether ( 1 ) and xanthorin 1- O -methyl ether ( 2 ) from the organic-soluble extractives of the indigenous Australian toadstool Dermocybe sp. WAT 22963 (Agaricales) . Drawn by the intensity of the pigmentation that remained in the aqueous phase when the total EtOH extract of Dermocybe sp.…”

“…Fresh fruiting bodies were macerated in EtOH overnight, the extracts were evaporated, and the residual slurry was partitioned between EtOAc and H 2 O. The deep red organic phase afforded, among other things the xanthorin derivatives 1 and 2 , which were identified by direct comparison with authentic materials . A small aliquot of the orange aqueous phase was stirred at room temperature with dilute HCl, and the resulting hydrolysate was extracted with EtOAc.…”