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Hyperforin
Hyperforin flat view Hyperforin stereospecific view
General
Systematic 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
Molecular formula	C35H52O4
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
Molar mass	536.78 g/mol
CAS number	11079-53-1
PubChem ID	114787
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa)

'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).
In a study by Thomas et al., (2007), using pelvic floor muscle contractile activity as a marker of the expulsion phase of ejaculation in anaesthetized rats, hyperforin and other seratoin agonists significantly reduced the pelvic floor contractions elicited by 8-OH-DPAT. Pharmacological modulation of the ejaculatory threshold using seratonin reuptake inhibitors and hyperforin may offer patients an option of achieving improved ejaculatory control.

Contents

See Also

References

See Also

★ St John's Wort

★ Serotonin

★ 5-HTP

★ hypericum

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.