Agaricon

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Structural formula
Structural formula of Agaricon
General
Surname Agaricon
Molecular formula C 10 H 11 N 3 O
Brief description
External identifiers / databases
CAS number
  • 732208-07-0 (Leucoagaricon Base)
  • 99280-75-8 (leuco agaricon HCl)
  • 99280-73-6 (dehydroleukoagaricon)
Wikidata Q41763865
properties
Molar mass 189.23 g mol −1
Physical state

firmly

Melting point
  • 115 ° C (agaricon; decomposition)
  • 224 ° C (leuco agaricon hydrochloride)
safety instructions
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 .

Agaricon is a mushroom poison from the carbolic mushroom ( Agaricus xanthodermus , synonym carbolic Egerling ). The structure was only clarified in 1985 and then synthesized.

properties

Agaricon is present in the fungus in its colorless leuco form , the leuco agaricon. This has the structural elements of amidine and phenylhydrazine , which are very rare in natural products . Leucoagaricon is autoxidizable. The yellow coloration of the carbolic mushroom is based on this property when the white skin is damaged and when the mushroom is prepared. After injury to the fruiting body, leuco agaricon changes into the orange-yellow agaricon in aqueous solution, a monohydrazone of 1,4-benzoquinone, on contact with atmospheric oxygen with the help of oxidases . Other sources suspect a biosynthesis from xanthodermine .

Autoxidation of the leuco agaricon (left) to the agaricon (right)

The structure of the oxidation product is not far removed from that of the deeply colored cyanine dyes.

Occurrence

Carbolic mushroom from the underside with a yellowing tuber

Leucoagaricon occurs in the widespread Karbol-Egerling (synonym: Karbol-Champignon ) in addition to xanthodermin 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 toxic and mutagenic phenylhydrazine .

Individual evidence

  1. ↑ a b c d e Burkhard Fugmann: RÖMPP Lexikon Naturstoffe, 1st edition, 1997 . Georg Thieme Verlag, 2014, ISBN 978-3-13-179291-4 , p. 12 ( Google Books ).
  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.
  3. ↑ Urs P. Schlunegger (Ed.): Biologically Active Molecules: Identification, Characterization and Synthesis Proceedings of a Seminar on Chemistry of Biologically Active Compounds and Modern Analytical Methods . Springer Science & Business Media, Berlin / Heidelberg 1989, ISBN 978-3-642-74582-9 , p. 4th ff . ( limited preview in Google Book search).
  4. ↑ a b c d Sabine Hilbig, Thomas Andries, Wolfgang Steglich, Timm Anke: On the chemistry and antibiotic activity of the Carbolegerling (Agaricus xanthoderma) . In: Angewandte Chemie . tape 97 , no. 12 , 1985, pp. 1063-1064 , doi : 10.1002 / anie.19850971222 .
  5. ^ Progress in the Chemistry of Organic Natural Products . Springer Science & Business Media, 2012, ISBN 978-3-7091-6971-1 , p. 239 ( Google Books ).
  6. ↑ Entry on phenylhydrazine in the GESTIS substance database of the IFA , accessed on October 9, 2017(JavaScript required) .