Hyperforin

Hyperforin

Clinical data
Dependence liability	Nil
Routes of administration	Oral
ATC code	none
Legal status
Legal status	US: OTC Unscheduled
Pharmacokinetic data
Metabolism	Hepatic and CYP3A & CYP2B
Biological half-life	9-19.64 hours
Identifiers
IUPAC name (1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dion
CAS Number	11079-53-1
PubChem (CID)	114787
IUPHAR/BPS	2764
DrugBank	DB01892 Y
ChemSpider	16736597 Y
UNII	RM741E34FP Y
KEGG	C07608 Y
ChEBI	CHEBI:5834 Y
ECHA InfoCard	100.112.565
Chemical and physical data
Formula	C35H52O4
Molar mass	536.784973
3D model (Jmol)	Interactive image
Melting point	79–80 °C (174–176 °F)
Solubility in water	0.66 mg/mL (20 °C)
SMILES CC(C)C(=O)[C@@]21C(=O)[C@@](C[C@H](C\C=C(/C)C)[C@@]1(C)CC\C=C(/C)C)(C\C=C(/C)C)C(=O)C(\C\C=C(/C)C)=C2\O
InChI InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1 Y Key:IWBJJCOKGLUQIZ-HQKKAZOISA-N Y
NY (what is this?)

Hyperforin is a produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St John's wort). Hyperforin (along with adhyperforin) is believed to be one of the three chief active constituents of St. John's wort -the other two being hypericin (along with pseudohypericin) and several flavonoid constituents.

Hyperforin has only been found in significant amounts in Hypericum perforatum (St. John's wort) with other related species such as Hypericum calycinum (Greater St. John's wort or Aaron's beard) containing lower levels of the phytochemical. It is thought to be a reuptake inhibitor. It accumulates in oil glands, pistils, and fruits, probably as a plant defense against herbivory. Other Hypericum species contain low amounts of hyperforin.

Hyperforin is a prenylated phloroglucinol derivative. The structure of hyperforin was elucidated by a research group from the Shemyakin Institute of Bio-organic Chemistry (USSR Academy of Sciences in Moscow) and published in 1975. A total synthesis of the non-natural enantiomer of hyperforin was reported in 2010 and a total synthesis of the natural enantiomer was disclosed in 2012.

Hyperforin is unstable in the presence of light and oxygen.

Some pharmacokinetic data on hyperforin is available for an extract containing 5% hyperforin. Maximal plasma levels (C_max) in human volunteers were reached 3.5h after administration of an extract containing 14.8 mg hyperforin. Biological half-life (t_1/2) and mean residence time were 9h and 12h respectively with an estimated steady state plasma concentration of 100 ng/mL (approx. 180 nM) for 3 doses/d. Linear plasma concentrations were observed within a normal dosage range and no accumulation occurred.