Xanthodermine

Structural formula
General
Surname	Xanthodermine
other names	N 2 - (4-hydroxyphenyl) - L -glutamoyl hydrazide; (2 S ) -2-Amino-5- [2- (4-hydroxyphenyl) hydrazino] -5-oxopentanoic acid ( IUPAC ) ;
Molecular formula	C 11 H 15 N 4 O 4
External identifiers / databases
PubChem	15382848
Wikidata	Q41742331
properties
Molar mass	253.25 g mol −1
Physical state	firmly
Melting point	190-192 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Xanthodermin is a mushroom poison from the carbolic Egerling (synonym carbolic mushroom , Agaricus xanthoderma ) with the very rare structural element of a phenylhydrazine . Structurally related to xanthodermine is the homologous agaritin with a hydroxymethyl instead of the phenolic OH group that occurs in mushrooms .

properties

Xanthodermin is autoxidizable. Due to this property, the yellow coloration of the carbolic mushroom is based on damage to the white skin and during preparation. A deep yellow monohydrazone of 1,4-benzoquinone is formed by dehydration (see reaction scheme). The structure was only clarified in 1985 and then synthesized.

Occurrence

Xanthodermin occurs in the widespread Karbol-Egerling (synonym Karbol-Champignon, Agaricus xanthoderma ) in addition to Agaricon and is also responsible for the toxicity and antibiotic effect of the fungus. The building block 4-hydroxyphenylhydrazine and its glucuronide are metabolic products of the likewise toxic and mutagenic phenylhydrazine . Studies of its cytotoxic effects are available for xanthodermin itself. It is much more effective than the ortho isomer found in lichens ( IC ₅₀ = 1.6 μM in B16 cells).

Individual evidence

↑ ^a ^b ^c ^d Angew.Chem. 97, 1063 (1985), Hilbig, Sabine, Andries, Thomas, Steglich, Wolfgang, Anke, Timm; On the chemistry and antibiotic activity of the Carbolegerling (Agaricus xanthoderma) ; doi: 10.1002 / anie.19850971222 ; Chem. Abstr. 1986: 106 184.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Interlaken_1988; Schlunegger, Urs P .; Biologically Active Molecules. Some Chemical Phenomena of Mushrooms and Toadstools (Springer Verlag); ISBN 978-3-642-74582-9 ( online ; from page 4)
↑ B. Fischer, J. Lüthy, C. Schlatter: Determination of the content of agaritin in cultivated mushrooms ( Agaricus bisporus ) using high-performance liquid chromatography (HPLC). Journal of Food Study and Research. September 1984, 179 (3), pp. 218-223, doi: 10.1007 / BF01041897 .
↑ Bioorg. Med. Chem. Lett. 20: 4582 (2010); Roullier, Catherine; Chollet-Krugler, Marylene; van de Weghe, Pierre; Lohezic-Le Devehat, Francoise; Boustie, J; A novel aryl-hydrazide from the marine lichen Lichina pygmaea: Isolation, synthesis of derivatives, and cytotoxicity assays ; doi: 10.1016 / j.bmcl.2010.06.013 ; Chem. Abstr. 2010: 900 778.

[Angew_97_1063-1] Angew.Chem. 97, 1063 (1985), Hilbig, Sabine, Andries, Thomas, Steglich, Wolfgang, Anke, Timm; On the chemistry and antibiotic activity of the Carbolegerling (Agaricus xanthoderma) ; doi: 10.1002 / anie.19850971222 ; Chem. Abstr. 1986: 106 184.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Interlaken_1988-3] Interlaken_1988; Schlunegger, Urs P .; Biologically Active Molecules. Some Chemical Phenomena of Mushrooms and Toadstools (Springer Verlag); ISBN 978-3-642-74582-9 ( online ; from page 4)

[X-Agaritin-4] B. Fischer, J. Lüthy, C. Schlatter: Determination of the content of agaritin in cultivated mushrooms ( Agaricus bisporus ) using high-performance liquid chromatography (HPLC). Journal of Food Study and Research. September 1984, 179 (3), pp. 218-223, doi: 10.1007 / BF01041897 .

[BMCL_20_4582-5] Bioorg. Med. Chem. Lett. 20: 4582 (2010); Roullier, Catherine; Chollet-Krugler, Marylene; van de Weghe, Pierre; Lohezic-Le Devehat, Francoise; Boustie, J; A novel aryl-hydrazide from the marine lichen Lichina pygmaea: Isolation, synthesis of derivatives, and cytotoxicity assays ; doi: 10.1016 / j.bmcl.2010.06.013 ; Chem. Abstr. 2010: 900 778.