Hyperforin

Structural formula
General
Surname	Hyperforin
other names	(1 R , 5 S , 6 R , 7 S ) -4-Hydroxy-6-methyl-1,3,7-tris (3-methylbut-2-enyl) -6- (4-methylpent-3-enyl) -5- (2-methylpropanoyl) bicyclo [3.3.1] non-3-ene-2,9-dione
Molecular formula	C 35 H 52 O 4
Brief description	light yellow solid
External identifiers / databases
EC number	601-000-9
ECHA InfoCard	100.112.565
PubChem	114787
ChemSpider	16736597
DrugBank	DB01892
Wikidata	Q412742
properties
Molar mass	536.79 g mol −1
Physical state	firmly
Melting point	79-80 ° C
safety instructions
H and P phrases	H: 225-301 + 311 + 331-370
	P: 210-280-302 + 352 + 312-304 + 340 + 312-370 + 378-403 + 235
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hyperforin is one of the main ingredients in St. John's wort .

Occurrence

St. John's wort ( Hypericum perforatum )

In the plant, hyperforin mainly accumulates in pistils and fruits, where it probably has defensive functions as a secondary plant substance.

Structure and biosynthesis

In chemical and structural terms, hyperforin can be derived from phloroglucinol by polyprenylation . In the process, the latter loses both its aromaticity and its phenolic character. The basic structure of the hyperforin arises biochemically from isobutyryl-CoA and three molecules of malonyl-CoA with the help of isobutyrophenone synthase.

Effects

Hyperforin is medically effective, one of the main effects of Hyperforin is as an antidepressant . Hyperforin is a reuptake inhibitor of serotonin , dopamine , norepinephrine , GABA and glutamic acids . So it inhibits the reuptake of these neurotransmitters from the synaptic cleft. Hyperforin also binds to the enzymes cytochrome P450 , CYP3A4 and CYP2C9 as well as to the pregnan X receptor (PXR).

Derived connections

Aristoforin (C ₃₇ H ₅₄ O ₆ , CAS number: 849215-53-8)

literature

Siegfried Bäumler. Medicinal plants practice today - portraits, recipes, application. Page 222. Elsevier Urban & Fischer Munich, 1st edition, 2007.

Web links

More about hyperforin and St. John's wort

Individual evidence

^ R. Scott Obach: Inhibition of Human Cytochrome P450 Enzymes by Constituents of St. John's Wort, an Herbal Preparation Used in the Treatment of Depression . In: Journal of Pharmacology and Experimental Therapeutics . tape 294 , no. 1 , 2000, pp. 88-95 ( full text ).
↑ Entry on Hyperforin. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.
↑ ^a ^b Hyperforin data sheet at Sigma-Aldrich , accessed on November 3, 2019 ( PDF ).

↑ L. Beerhues: Hyperforin. In: Phytochemistry . 67/20/2006. Pp. 2201-7. PMID 16973193

^ J. Barnes et al .: Herbal Medicines: A guide for healthcare professionals . Pharmaceutical Press, London 2002, ISBN 0-85369-474-5 .

↑ SS Chatterjee et al .: Hyperforin as a possible antidepressant component of hypericum extracts . In: Life Sci . 63/6/1998. Pp. 499-510, PMID 9718074 .

[1] R. Scott Obach: Inhibition of Human Cytochrome P450 Enzymes by Constituents of St. John's Wort, an Herbal Preparation Used in the Treatment of Depression . In: Journal of Pharmacology and Experimental Therapeutics . tape 294 , no. 1 , 2000, pp. 88-95 ( full text ).

[2] Entry on Hyperforin. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.

[Sigma-3] Hyperforin data sheet at Sigma-Aldrich , accessed on November 3, 2019 ( PDF ).

[4] L. Beerhues: Hyperforin. In: Phytochemistry . 67/20/2006. Pp. 2201-7. PMID 16973193

[5] J. Barnes et al .: Herbal Medicines: A guide for healthcare professionals . Pharmaceutical Press, London 2002, ISBN 0-85369-474-5 .

[6] SS Chatterjee et al .: Hyperforin as a possible antidepressant component of hypericum extracts . In: Life Sci . 63/6/1998. Pp. 499-510, PMID 9718074 .