hypericin

Hypericin[1]
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 Y
PubChem	5281051
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
ChemSpider ID	4444511
Properties
Molecular formula	C30H16O8
Molar mass	504.44 g mol−1
Appearance	Blue-black solid
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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. Because hypericin accumulates preferentially on 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