Hyperforin

Chembox new
Name = Hyperforin
ImageFile = hyperforin.png ImageSize = 300px
ImageName = Hyperforin flat view
ImageFile1 = Hyperforin.svg
ImageSize1 = 250px
ImageName1 = Hyperforin stereospecific view
IUPACName = (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
Section1 = Chembox Identifiers
Pubchem = 114787
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
CASNo = 11079-53-1
Section2 = Chembox Properties
Formula = C₃₅H₅₂O₄
MolarMass = 536.78 g/mol

Hyperforin is one of the principal constituents identified in St John's wort.

Pharmacology

Hyperforin is a prenylated phloroglucinol believed to be the main active constituent responsible for the antidepressant effects of extracts of St John's wort.cite book |author=Newall, Carol A.; Joanne Barnes; Anderson, Linda R. |title=Herbal medicines: a guide for healthcare professionals |publisher=Pharmaceutical Press |location=London |year=2002 |pages= |isbn=0-85369-474-5 |oclc= |doi=] Hyperforin has been shown to inhibit the uptake of the neurotransmitters serotonin, dopamine, noradrenaline, GABA and glutamate.cite journal |author=Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A, Müller WE |title=Hyperforin as a possible antidepressant component of hypericum extracts |journal=Life Sci. |volume=63 |issue=6 |pages=499–510 |year=1998 |pmid=9718074 |doi=10.1016/S0024-3205(98)00299-9] It was identified as a specific activator of the ion channel TRPC6 which is involved in neuronal axonal sprouting. The activation of TRPC6 causes entry of sodium and calcium ions in neuronal cells which can explain the inhibition of neurotransmitter uptake.cite journal |author=Leuner K, Kazanski V, Müller M, "et al" |title=Hyperforin--a key constituent of St. John's wort specifically activates TRPC6 channels |journal=The FASEB journal : official publication of the Federation of American Societies for Experimental Biology |volume=21 |issue=14 |pages=4101–11 |year=2007 |month=December |pmid=17666455 |doi=10.1096/fj.07-8110com |url=]
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).Fact|date=October 2008

Chemistry

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.cite journal |author=Bystrov NS, Gupta ShR, Dobrynin VN, Kolosov MN, Chernov BK |title= [Structure of the antibiotic hyperforin] |language=Russian |journal=Doklady Akademii nauk SSSR |volume=226 |issue=1 |pages=88–90 |year=1976 |month=January |pmid=1248360 |doi= |url=] cite journal |author=Bystrov NS, Chernov BK, Dobrynin VN, Kolosov MN |title= [The structure of hyperforin] |language= |journal=Tetrahedron Letters |volume=16 |issue=32 |pages=2791-2794 |year=1975 |month= |pmid= |doi=10.1016/S0040-4039(00)75241-5 |url=] . There is no published total synthesis of hyperforin, despite the attempts by several research groups.

As ejaculatory control

Hyperforin and other serotonin agonists significantly reduces the pelvic floor contractions elicited by 8-OH-DPAT.cite journal |author=Thomas CA, Tyagi S, Yoshimura N, Chancellor MB, Tyagi P |title=Effect of hyperforin-enriched extract on pro-ejaculatory effect of 8-hydroxy-2-(di-N-propylamino)tetralin in anesthetized rats |journal=Urology |volume=70 |issue=4 |pages=813–6 |year=2007 |pmid=17991578 |doi=10.1016/j.urology.2007.05.016] Thus, pharmacological modulation of the ejaculatory threshold using serotonin reuptake inhibitors and hyperforin may offer patients an option of achieving improved ejaculatory control.

ee also

*St John's Wort
*Serotonin
*5-HTP
*Hypericum

References