Polyporic acid is a para-

terphenyl Terphenyls are a group of closely related aromatic hydrocarbons. Also known as diphenylbenzenes or triphenyls, they consist of a central benzene ring substituted with two phenyl groups. There are three substitution patterns: ''ortho''-terphenyl ...

benzoquinone Benzoquinone (C6H4O2) is a quinone with a single benzene ring. There are 2 (out of 3 hypothetical) benzoquinones: * 1,4-Benzoquinone, most commonly, right image (also ''para''-benzoquinone, ''p''-benzoquinone, ''para''-quinone, or just quinone) * 1 ...

compound first identified by German chemist Stahlschmidt from a

mycelial Mycelium (plural mycelia) is a root-like structure of a fungus consisting of a mass of branching, thread-like hyphae. Fungal colonies composed of mycelium are found in and on soil and many other substrate (biology), substrates. A typical single ...

culture of the

fungus A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from th ...

species ''

Hapalopilus nidulans ''Hapalopilus rutilans'' (also known as ''Hapalopilus nidulans'') is a species of polypore fungus in the family Polyporaceae. Officially described in 1821, it was transferred to its current genus ''Hapalopilus'' six decades later. It is commonly ...

'' in 1877. This chemical, present at 20–40% of the fresh weight of the

fruit bodies The sporocarp (also known as fruiting body, fruit body or fruitbody) of fungi is a multicellular structure on which spore-producing structures, such as basidia or asci, are borne. The fruitbody is part of the sexual phase of a fungal life cyc ...

, inhibits the enzyme

dihydroorotate dehydrogenase Dihydroorotate dehydrogenase (DHODH) is an enzyme that in humans is encoded by the ''DHODH'' gene on chromosome 16. The protein encoded by this gene catalyzes the fourth enzymatic step, the ubiquinone-mediated oxidation of dihydroorotate to ...

. It is found in other mushrooms, but in much lower amounts. In animal studies, consumption of polyporic acid caused reduced locomotor activity, depressed visual placing response, hepatorenal failure, metabolic acidosis, hypokalaemia, and hypocalcaemia. 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''. Polyporic acid has some

antifungal An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as crypto ...

and

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

activity. It has been shown to be an intermediate in the biosynthesis of allantofuranone, a gamma-lactone antibiotic from the fungus ''Allantophomopsis lycopodina''.

References

{{Reflist, refs= {{cite book , veditors=Bechtold T, Mussak R , title=Handbook of Natural Colorants , chapter=Dyes from lichens and mushrooms , author=Räisänen R. , chapter-url=https://books.google.com/books?id=hBFxuH5uXyIC&pg=PA192 , year=2009 , publisher=John Wiley & Sons , location=Chichester, UK , isbn=978-0-470-74496-3 , page=192 {{cite journal , vauthors=Brewer D, Maass WS, Taylor A , title=The effect on fungal growth of some 2,5-dihydroxy-1,4-benzoquinones , journal=Canadian Journal of Microbiology , year=1977 , volume=23 , issue=7 , pages=845–51 , pmid=884625 , doi=10.1139/m77-126 {{cite journal , vauthors=Brewer D, Jen WC, Jones GA, Taylor A , title=The antibacterial activity of some naturally occurring 2,5-dihydroxy-1,4-benzoquinones , journal=Canadian Journal of Microbiology , year=1984 , volume=30 , issue=8 , pages=1068–1092 , pmid=6541963 , doi=10.1139/m84-166 {{cite book , vauthors=Spatafora C, Calì V, Tringali C , title=Polyhydroxy-''p''-terphenyls and related ''p''-terphenylquinones from fungi: overview and biological properties , journal=Studies in Natural Products Chemistry , year=2003 , volume=29 , issue=J , pages=263–307 , doi=10.1016/S1572-5995(03)80009-1, isbn=9780444515100 {{cite journal , vauthors=Kraft J, Bauer S, Keilhoff G, Miersch J, Wend D, Riemann D, Hirschelmann R, Holzhausen HJ, Langner J , title=Biological effects of the dihydroorotate dehydrogenase inhibitor polyporic acid, a toxic constituent of the mushroom ''Hapalopilus rutilans'', in rats and humans , journal=Archives of Toxicology , year=1998 , volume=72 , issue=11 , pages=711–721 , pmid=9879809 , doi=10.1007/s002040050565, s2cid=41488737 {{cite journal , vauthors=Schüffler A, Liermann JC, Opatz T, Anke T , title=Elucidation of the biosynthesis and degradation of allantofuranone by isotopic labelling and fermentation of modified precursors , journal=ChemBioChem , year=2011 , volume=12 , issue=1 , pages=148–154 , doi=10.1002/cbic.201000448, pmid=21181846 , s2cid=30217850 {{cite journal , author=Stahlschmidt C. , title=Ueber eine neue in der Natur vorkommende organische Säure , journal=Justus Liebigs Annalen der Chemie, year=1877 , trans-title=A new naturally occurring organic acid , volume=187 , issue=2–3 , pages=177–197 , doi=10.1002/jlac.18771870204, url=https://zenodo.org/record/1447337 1,4-Benzoquinones Phenyl compounds Hydroxybenzoquinones Mycotoxins found in Basidiomycota Neurotoxins