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Hyperforin

Hyperforin


IUPAC name	(1S,5S,7S,8R)-4-hydroxy-8-methyl-3,5,7 -tris(3-methylbut-2-enyl)-8-(4-methylpent- 3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1] non-3-ene-2,9-dione
Identifiers
CAS number	11079-53-1
SMILES	CCCC(=O)[C@]12C(=O)C(=C([C@](C1=O) (C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C) CC=C(C)C)O)CC=C(C)C
Properties
Molecular formula	C₃₅H₅₂O₄
Molar mass	536.78 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Hyperforin is one of the principal constituents identified in St John's wort. Hyperforin is a prenylated phloroglucinol believed to be the main active constituent responsible for its antidepressant effects. (Barnes et al., 2002) Hyperforin has been shown to inhibit the uptake of 5-HT(serotonin), dopamine, noradrenaline, GABA and glutamate. (Chatterjee et al., 1998) Hyperforin is also thought to be responsible for the induction of the cytochrome P450 enzymes CYP3A4 and CYP2C9 by binding to the Pregnane X Receptor (PXR).

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As ejaculatory control

Hyperforin and other serotonin agonists significantly reduces the pelvic floor contractions elicited by 8-OH-DPAT. ^[1] Thus, pharmacological modulation of the ejaculatory threshold using serotonin reuptake inhibitors and hyperforin may offer patients an option of achieving improved ejaculatory control.

References

Barnes J, Anderson LA, Phillipson JD (2002). Herbal Medicines: A guide for healthcare professionals (2 ed.) London: Pharmaceutical Press. ISBN 0-85369-474-5
Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A, Muller WE (1998a). Hyperforin as a possible antidepressant component of hypericum extracts. Life Sci 63 (6), 499-510.
Thomas, C.A., Tyagi, S., Yoshimura, N., Chancellor, M.B., Tyagi, P.: Effect of hyperforin-enriched extract on pro-ejaculatory effect of 8-Hydroxy-2-(Di-N-Propylamino) tetralin in anesthetized rats. Urology, in press, 2007.

Category: Antidepressants