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
EC Number	611-335-2;
KEGG	C10392;
PubChem CID	4978;
UNII	MQ0U4663ZO;
CompTox Dashboard (EPA)	DTXSID00204541 ;
	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;
	SMILES 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

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

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.
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.
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.
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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[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.