Hypericin: Difference between revisions

Hypericin^[1]
Names
	IUPAC name 1,3,4,6,8,13-hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione
	Other names 4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone
Identifiers
CAS Number	548-04-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	4444511;
ECHA InfoCard	100.008.129
PubChem CID	5281051;
CompTox Dashboard (EPA)	DTXSID40203270 ;
	SMILES CC1=CC(=C2C3=C1C4=C5C(=C(C=C4C)O)C(=O)C6=C(C=C(C7=C6C5=C3C8=C7C(=CC(=C8C2=O)O)O)O)O)O;
Properties
Chemical formula	C30H16O8
Molar mass	504.450 g·mol−1
Appearance	Blue-black solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 23:50, 10 February 2010

Hypericin is a red-coloured anthraquinone-derivative, which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint John's wort).^[2] Hypericin is believed to act as an antibiotic and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine β-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine.

The crude extract of Hypericum has weak receptor affinity for MAO-A and MAO-B receptors. Isolated hypericin does not display this activity, but does have affinity for NMDA receptors.

The large chromophore system in the molecule means that it can cause photosensitivity when ingested beyond threshold amounts. Photosensitivity is often seen in animals that have been allowed to graze on St. John's Wort. Because hypericin accumulates preferentially in cancerous tissues, it is also used as an indicator of cancerous cells. In addition, hypericin is under research as an agent in photodynamic therapy, whereby a biochemical is absorbed by an organism to be later activated with spectrum-specific light from specialized lamps or laser sources, for therapeutic purposes.

References

^ Merck Index, 11th Edition, 4799
^ Oubre, Alondra (1991). "Hypericin: the active ingredient in Saint John's Wort". Retrieved September 18, 2006. {{cite web}}: Cite has empty unknown parameters: |month= and |coauthors= (help)

[1] Merck Index, 11th Edition, 4799

[2] Oubre, Alondra (1991). "Hypericin: the active ingredient in Saint John's Wort". Retrieved September 18, 2006. {{cite web}}: Cite has empty unknown parameters: |month= and |coauthors= (help)

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 The crude extract of ''Hypericum'' has weak receptor affinity for [[Monoamine oxidase A|MAO-A]] and [[Monoamine oxidase B|MAO-B]] receptors. Isolated hypericin does not display this activity, but does have affinity for [[NMDA receptor]]s.
-The large [[chromophore]] system in the molecule means that it can cause [[photosensitivity]] when ingested beyond threshold amounts.  Because hypericin accumulates preferentially on [[cancer]]ous tissues, it is also used as an indicator of cancerous cells. In addition, hypericin is under research as an agent in [[photodynamic therapy]], whereby a biochemical is absorbed by an organism to be later activated with spectrum-specific light from specialized lamps or [[laser]] sources, for therapeutic purposes.
+The large [[chromophore]] system in the molecule means that it can cause [[photosensitivity]] when ingested beyond threshold amounts.  Photosensitivity is often seen in [[Photosensitivity_in_animals|animals]] that have been allowed to graze on St. John's Wort.  Because hypericin accumulates preferentially in [[cancer|cancerous]] tissues, it is also used as an indicator of cancerous cells. In addition, hypericin is under research as an agent in [[photodynamic therapy]], whereby a biochemical is absorbed by an organism to be later activated with spectrum-specific light from specialized lamps or [[laser]] sources, for therapeutic purposes.
 ==References==