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Thelephoric acid

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Thelephoric acid
Structural formula of thelephoric acid
Space-filling model of the thelephoric acid molecule
Names
Preferred IUPAC name 2,3,8,9-Tetrahydroxybenzobis(benzofuran)-6,12-dione
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H8O8/c19-7-1-5-11(3-9(7)21)25-17-13(5)15(23)18-14(16(17)24)6-2-8(20)10(22)4-12(6)26-18/h1-4,19-22HKey: PDICCECAPKBDBB-UHFFFAOYSA-N
  • InChI=1/C18H8O8/c19-7-1-5-11(3-9(7)21)25-17-13(5)15(23)18-14(16(17)24)6-2-8(20)10(22)4-12(6)26-18/h1-4,19-22HKey: PDICCECAPKBDBB-UHFFFAOYAC
SMILES
  • c1c2c(cc(c1O)O)oc3c2C(=O)c4c(c5cc(c(cc5o4)O)O)C3=O
Properties
Chemical formula C18H8O8
Molar mass 352.254 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Thelephoric acid is a terphenylquinone pigment that is found in several fungi, such as Omphalotus subilludens and Polyozellus multiplex. Thelephoric acid has been shown to inhibit prolyl endopeptidase, an enzyme that has a role in processing proteins (specifically, amyloid precursor protein) in Alzheimer's disease. Chemicals that inhibit prolyl endopeptidase have attracted research interest due to their potential therapeutic effects. It is derived from atromentin, and its precursor can be from cyclovariegatin. Fragmentation patterns have suggested that polymers of thelephoric acid exists.

References

  1. Sullivan G, Garrett RD, Lenehan RF (1971). "Occurrence of atromentin and thelephoric acid in cultures of Clitocybe subilludens". Journal of Pharmaceutical Sciences. 60 (11): 1727–29. doi:10.1002/jps.2600601134. PMID 4332377.
  2. Ju-Yeon K, Rhee I-K, Lee K-B, Hwang J-S, Yoo I-D, Song K-S (1999). "Thelephoric acid and kynapcin-9 in mushroom Polyozellus multiflex inhibit prolyl endopeptidase in vitro". Journal of Microbiology and Biotechnology. 9 (6): 798–803.
  3. Hwang JS, Song KS, Kim WG, Lee TH, Koshino H, Yoo ID (1997). "Polyozellin, a new inhibitor of prolyl endopeptidase from Polyozellus multiplex". The Journal of Antibiotics. 50 (9): 773–77. doi:10.7164/antibiotics.50.773. PMID 9360624.
  4. Nagasawa I, Kaneko A, Suzuki T, Nishio K, Kinoshita K, Shiro M, Koyama K (2014). "Potential anti-angiogenesis effects of p-terphenyl compounds from Polyozellus multiplex". Journal of Natural Products. 77 (4): 963–8. doi:10.1021/np401046z. PMID 24601669.
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