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]

References

  1. ^ Stahlschmidt C. (1877). "Ueber eine neue in der Natur vorkommende organische Säure" [A new naturally occurring organic acid]. Justus Liebigs Annalen der Chemie. 187 (2–3): 177–197. doi:10.1002/jlac.18771870204.
  2. ^ Spatafora C, Calì V, Tringali C (2003). Polyhydroxy-p-terphenyls and related p-terphenylquinones from fungi: overview and biological properties. Vol. 29. pp. 263–307. doi:10.1016/S1572-5995(03)80009-1. ISBN 9780444515100. {{cite book}}: |journal= ignored (help)
  3. ^ Räisänen R. (2009). "Dyes from lichens and mushrooms". In Bechtold T, Mussak R (eds.). Handbook of Natural Colorants. Chichester, UK: John Wiley & Sons. p. 192. ISBN 978-0-470-74496-3.
  4. ^ a b c d Kraft J, Bauer S, Keilhoff G, Miersch J, Wend D, Riemann D, Hirschelmann R, Holzhausen HJ, Langner J (1998). "Biological effects of the dihydroorotate dehydrogenase inhibitor polyporic acid, a toxic constituent of the mushroom Hapalopilus rutilans, in rats and humans". Archives of Toxicology. 72 (11): 711–721. doi:10.1007/s002040050565. PMID 9879809. S2CID 41488737.
  5. ^ Brewer D, Maass WS, Taylor A (1977). "The effect on fungal growth of some 2,5-dihydroxy-1,4-benzoquinones". Canadian Journal of Microbiology. 23 (7): 845–51. doi:10.1139/m77-126. PMID 884625.
  6. ^ Brewer D, Jen WC, Jones GA, Taylor A (1984). "The antibacterial activity of some naturally occurring 2,5-dihydroxy-1,4-benzoquinones". Canadian Journal of Microbiology. 30 (8): 1068–1092. doi:10.1139/m84-166. PMID 6541963.
  7. ^ Schüffler A, Liermann JC, Opatz T, Anke T (2011). "Elucidation of the biosynthesis and degradation of allantofuranone by isotopic labelling and fermentation of modified precursors". ChemBioChem. 12 (1): 148–154. doi:10.1002/cbic.201000448. PMID 21181846. S2CID 30217850.