Polyporic acid

Polyporic acid

Names
IUPAC name 2,5-Dihydroxy-3,6-diphenylcyclohexa-2,5-diene-1,4-dione
Other names Polyporin; Orygameic acid
Identifiers
CAS Number	548-59-4
ChemSpider	10587
Jmol interactive 3D	Image
MeSH	C118527
PubChem	11056
InChI 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
SMILES C1=CC=C(C=C1)C2=C(C(=O)C(=C(C2=O)O)C3=CC=CC=C3)O
Properties
Chemical formula	C18H12O4
Molar mass	292.29 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Polyporic acid is a 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] 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 black rot 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". Studies in Natural Products Chemistry 29 (J): 263–307. doi:10.1016/S1572-5995(03)80009-1.
3. Räisänen R. (2009). "Dyes from lichens and mushrooms". In Bechtold T, Mussak R. Handbook of Natural Colorants. Chichester, UK: John Wiley & Sons. p. 192. ISBN 978-0-470-74496-3.
4. 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.
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.