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]

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
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.111.993 Edit this at Wikidata
EC Number
  • 611-335-2
KEGG
UNII
  • 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
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).

References

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  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.