Atromentine

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Structural formula
Structural formula of atromentine
General
Surname Atromentine
other names
  • 2,5-dihydroxy-3,6-bis (4-hydroxyphenyl) -cyclohexa-2,5-diene-1,4-dione
  • 2,5-dihydroxy-3,6-bis (4-hydroxyphenyl) - p -benzoquinone
Molecular formula C 18 H 12 O 6
Brief description

bronze-colored panels

External identifiers / databases
CAS number 519-67-5
PubChem 99148
ChemSpider 89570
Wikidata Q4817643
properties
Molar mass 324.3 g mol −1
Physical state

firmly

Melting point

> 300 ° C

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 .

Atromentine is a mushroom ingredient and a member of the terphenylquinone class . The connection was first described by Wilhelm Thörner in 1878.

Occurrence

Atromentin occurs in the brown outer skin of the velvet foot kremplings ( Paxillus atrotomentosus , Basidiomycetes ). The colorless leucomentins are present in the mushroom meat . In these, one, two or three hydroxyl groups of the central phenyl unit are esterified with (2 Z , 4 S , 5 S ) -4,5-epoxy-2-hexenoic acid.

Leucoatromentin
(2Z, 4S, 5S) -4,5-epoxy-2-hexenoic acid
Leucoatromentin (2 Z , 4 S , 5 S ) -4,5-epoxy-2-hexenoic acid

The leucomentins can easily be split under alkaline conditions and oxidized to atromentin. Atromentin derivatives esterified with various acids are also found in fungi (example: aurantiacin )

biosynthesis

Atromentine is produced during biosynthesis through the dimerization of 4-hydroxyphenylpyruvic acid.

properties

Atromentin acts including as inhibitor for enzymes of HIV - replication . This compound is therefore a very promising metabolite for biomedical research and for the development of new drugs.

Individual evidence

  1. ↑ a b c d Entry on Atromentin. In: Römpp Online . Georg Thieme Verlag, accessed on September 3, 2019.
  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. ↑ W. Thörner: About a quinone-like body occurring in an Agaricus species . In: Reports of the German Chemical Society . tape 11 , no. 1 , January 1878, p. 533-535 , doi : 10.1002 / cber.187801101143 .
  4. ↑ entry to Leucomentine. In: Römpp Online . Georg Thieme Verlag, accessed on September 4, 2019.
  5. ↑ Hartmut Foerster: Atromentin biosynthesis. MetaCyc, 2014, accessed September 4, 2019 .