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Polyporic acid

Polyporic acid
Names
Preferred IUPAC name
23,26-Dihydroxy[11,21:24,31-terphenyl]-22,25-dione
Other names
Polyporin; Orygameic acid
Identifiers
3D model (JSmol)
ChemSpider
MeSH C118527
UNII
  • InChI=1S/C18H12O4/c19-15-13(11-7-3-1-4-8-11)16(20)18(22)14(17(15)21)12-9-5-2-6-10-12/h1-10,19,22H
    Key: HZKFHDXTSAYOSN-UHFFFAOYSA-N
  • InChI=1/C18H12O4/c19-15-13(11-7-3-1-4-8-11)16(20)18(22)14(17(15)21)12-9-5-2-6-10-12/h1-10,19,22H
    Key: HZKFHDXTSAYOSN-UHFFFAOYAL
  • C1=CC=C(C=C1)C2=C(C(=O)C(=C(C2=O)O)C3=CC=CC=C3)O
Properties
C18H12O4
Molar mass 292.290 g·mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Polyporic acid is a para-terphenyl benzoquinone compound first identified by German chemist Stahlschmidt from a mycelial culture of the fungus species Hapalopilus nidulans in 1877.[1][2] This chemical, present at 20–40% of the fresh weight of the fruit bodies,[3] inhibits the enzyme dihydroorotate dehydrogenase.[4] It is found in other mushrooms, but in much lower amounts.[4]

In animal studies, consumption of polyporic acid caused reduced locomotor activity, depressed visual placing response, hepatorenal failure, metabolic acidosis, hypokalaemia, and hypocalcaemia.[4] Because these effects are similar to those observed in individuals poisoned by H. nidulans, polyporic acid is thought to be the primary toxin in H. nidulans.[4]

Polyporic acid has some antifungal[5] and antibacterial activity.[6] It has been shown to be an intermediate in the biosynthesis of allantofuranone, a gamma-lactone antibiotic from the fungus Allantophomopsis lycopodina.[7]

  1. ^ Cite error: The named reference Stahlschmidt 1877 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Calì 2003 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Bechtold 2009 was invoked but never defined (see the help page).
  4. ^ a b c d Cite error: The named reference Kraft 1998 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Brewer 1977 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Brewer 1984 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Schüffler 2011 was invoked but never defined (see the help page).

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Polyporsäure German Acide polyporique French 多孔菌酸 Chinese

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