Dermocybe sanguinea

Most of the previously identified 25 chlorinated anthraquinones are found in lichen and fungi (1). The newly discovered examples have a wider range of sources. Studies of the lichen Nephroma laevigatum from the British Columbia coast have identified the new anthraquinone, 7-chloro-l-O-methyl-co-hydroxy-emodin (2157), and the two novel hypericins, 7,7 -dichlorohypericin (2158) and 2,2, 7,7 -tetrachlorohypericin (2159) (1931), as well as 5-chloroemodin (2160), 5-c h I oro -1 - (9 - m e t h v I - o >- h yd ro x ye m od i n (2161), and 5-chloro-co-hydroxyemodin (2162) (1932). In addition to containing several known chlorinated anthraquinones, the Scandinavian fungus Dermocybe sanguinea has afforded the new 5,7-dichloroendocrocin (2163) (1933). The novel tetracyclic anthraquinones... 

Raisanen R, Bjork H, Hynninen PH (2000) Two-Dimensional TLC Separation and Mass Spectrometric Identification of Anthraquinones Isolated from the Fungus Dermocybe sanguinea. Z Naturforsch 55c 195... 

VON WRIGHT A, RAATIKAINEN O, TAIPALE H, KARENLAMPI S and MAKI-PAAKKANEN J (1992) Directly acting geno- and cytotoxic agents from a wild mushroom Dermocybe sanguinea. Mutation Research 269, 27-33. 

Obt. as a mixture with its 2 -epimer. Metab. of toadstool Dermocybe sanguinea. Dark green needles (MeOH). Mp 155-160°. 

Metab. of toadstool Dermocybe sanguinea. Orange needles (EtOAc/HCOOH). Mp 268-271°. [ot] +22 (c, 0.07 in CHCI3). Isol. as a partial racemate. 

Metab. of Dermocybe sanguinea. Orange needles (MeOH). Mp 195-200°. 

Scheme 52. Biosynthetic relationships between pigments of Dermocybe sanguinea...

Pilzpigmente X. Anthrachinon-glucoside aus Dermocybe sanguinea (Wulf. ex Fr.) Wiinsche. Chem. Ber. 105, 2928 (1972). 

That emodin (288) is the precursor of both dermoglaucin (297) and dermocybin (298) has been established by the successful incorporation of [2,4- H2]emodin-6-P-D-glucopyranoside into these neutral pigments in young fruit bodies of Dermocybe semisanguinea 601), a species related to D. sanguinea. ... 

The significance to the systematic classification of Dermocybe of various modes of pigment development, including the sanguinea type and cinnabarina type illustrated above, has been expounded further by Keller 401, 403). 

Keller, G., and J.F. Ammirati Chemotaxonomic Significance of Anthraquinone Derivatives in North American Species of Dermocybe, Section Sanguineae. Myco-taxon 18, 357 (1983). 

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