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]
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| Names | |
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| Preferred IUPAC name
23,26-Dihydroxy[11,21:24,31-terphenyl]-22,25-dione | |
| Other names
Polyporin; Orygameic acid
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| MeSH | C118527 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C18H12O4 | |
| Molar mass | 292.290 g·mol−1 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Toxic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
edit- ^ 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.
- ^ 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) - ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.