Thelephoric acid

Thelephoric acid
Structural formula of thelephoric acid
Space-filling model of the thelephoric acid molecule
Names
Preferred IUPAC name
2,3,8,9-Tetrahydroxybenzo[1,2-b:4,5-b′]bis([1]benzofuran)-6,12-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • 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/h1-4,19-22H
    Key: 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/h1-4,19-22H
    Key: PDICCECAPKBDBB-UHFFFAOYAC
  • c1c2c(cc(c1O)O)oc3c2C(=O)c4c(c5cc(c(cc5o4)O)O)C3=O
Properties
C18H8O8
Molar mass 352.254 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thelephoric acid is a terphenylquinone pigment that is found in several fungi, such as Omphalotus subilludens[1] and Polyozellus multiplex.[2] 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.[3][4] 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.