Pseudohypericin

Last updated
Pseudohypericin
Pseudohypericin2DACS.svg
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.111.993 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 611-335-2
KEGG
PubChem CID
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).

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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