Pseudohypericin

Pseudohypericin
Names
Preferred IUPAC name
1,3,4,6,8,13-Hexahydroxy-10-(hydroxymethyl)-11-methylphenanthro[3,4,5,6-fghij]perylene-7,14-dione
Identifiers
CAS Number
  • 55954-61-5
3D model (JSmol)
  • Interactive image
3DMet
  • B03886
ChEBI
  • CHEBI:8605
ChEMBL
  • ChEMBL1614664
ChemSpider
  • 4445065
ECHA InfoCard 100.111.993 Edit this at Wikidata
EC Number
  • 611-335-2
KEGG
  • C10392
PubChem CID
  • 4978
UNII
  • MQ0U4663ZO
CompTox Dashboard (EPA)
  • DTXSID00204541 Edit this at Wikidata
InChI
  • InChI=1S/C30H16O9/c1-7-2-9(32)19-23-15(7)16-8(6-31)3-10(33)20-24(16)28-26-18(12(35)5-14(37)22(26)30(20)39)17-11(34)4-13(36)21(29(19)38)25(17)27(23)28/h2-5,31,34-39H,6H2,1H3
    Key: NODGUBIGZKATOM-UHFFFAOYSA-N
  • CC1=CC(=O)C2=C(C3=C(C=C(C4=C3C5=C6C7=C(C1=C25)C(=CC(=O)C7=C(C8=C(C=C(C4=C86)O)O)O)CO)O)O)O
Properties
Chemical formula
 C30H16O9
Molar mass 520.449 g·mol−1
log P 4.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Pseudohypericin is an aromatic polycyclic dione that is very closely related to hypericin. It is found most commonly in the St. John's wort family of plants, namely in Hypericum perforatum.[1] In preliminary studies in animal models, pseudohypericin has shown antiviral effects.[2][3] It may also contribute to the potential antidepressant effect of Hypericum perforatum extracts.[4]

References

  1. ^ Kitanov, Gerassim M. (2001). "Hypericin and pseudohypericin in some Hypericum species". Biochemical Systematics and Ecology. 29 (2): 171–178. doi:10.1016/S0305-1978(00)00032-6. PMID 11106845.
  2. ^ Meruelo, D.; Lavie, G.; Lavie, D. (1988). "Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: Aromatic polycyclic diones hypericin and pseudohypericin". Proceedings of the National Academy of Sciences. 85 (14): 5230–5234. Bibcode:1988PNAS...85.5230M. doi:10.1073/pnas.85.14.5230. PMC 281723. PMID 2839837.
  3. ^ Hudson, J.B.; Lopez-Bazzocchi, I.; Towers, G.H.N. (1991). "Antiviral activities of hypericin". Antiviral Research. 15 (2): 101–112. doi:10.1016/0166-3542(91)90028-P. PMID 1650164.
  4. ^ Butterweck, Veronika; Petereit, Frank; Winterhoff, Hilke; Nahrstedt, Adolf (1998). "Solubilized Hypericin and Pseudohypericin from Hypericum perforatum Exert Antidepressant Activity in the Forced Swimming Test3". Planta Medica. 64 (4): 291–294. doi:10.1055/s-2006-957437. PMID 9619107.
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