044889
CAS Number
238074-03-8Grade
Highly PurifiedMDL Number
MFCD04000098Molecular Formula
C35H51O4•C12H24NMolecular Weight
718.1EU Commodity Code
38220090Shipping Temp
RTStorage Temp
4°C/-20°CHyperforin DCHA
Key constituent of St. John's wort. Shows properties of potential pharmacological interest, including anti-bacterial, anti-malarial, anti-inflammatory, anti-cancer and anti-angiogenic effects. Anti-depressant and anxiolytic compound. Specific activator of TRPC6 channels. Inhibits the re-uptake of neurotransmitters in synapses (serotonin, norepinephrine, dopamine, GABA, glutamate). Activator of the pregnane X receptor (PXR). Regulates expression of the cytochrome P450 CYP3A4 and CYP2C9 and hepatic drugs metabolism. Potential anti-Alzheimer compound. Potent SIRT1 (sirtuin 1) and SIRT2 (sirtuin 2) inhibitor.
Synonyms
(1R,5R,6R,7S)-2-Hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-enyl)-6-(4-methylpent-3-enyl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-2-ene-4,9-dione . DCHA
Source
Isolated from St. John's wort (Hypericum perforatum)
Molecular Formula
C35H51O4•C12H24N
Solubility
100% ethanol, methanol or DMSO.
Appearance
Supplied as a white to off-white solid.
Note
The DCHA salt stabilizes hyperforin which normally has only a short shelf life.
Storage and Stability
Store at -20°C under inert atmosphere. Protect from light. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
Toxicity and Hazards
All products should be handled by qualified personnel only, trained in laboratory procedures.
Intended for research use only. Not for use in human, therapeutic, or diagnostic applications.
References
1. Antibacterial activity of hyperforin from St John's wort, against multiresistant Staphylococcus aureus and gram-positive bacteria: C.M. Schempp, et al.; Lancet 353, 2129 (1999)|2. St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor: L.B. Moore, et al.; PNAS 97, 7500 (2000)|3. Hyperforin-antidepressant activity by a novel mechanism of action: W.E. Müller, et al.; Pharmacopsychiatry 34 (Suppl 1), S98 (2001)|4. Hypericum perforatum (St John's Wort): a non-selective reuptake inhibitor? A review of the recent advances in its pharmacology: P.J. Nathan; J. Psychopharmacol. 15, 47 (2001) (Review)|5. Inhibition of tumour cell growth by hyperforin, a novel anticancer drug from St. John's wort that acts by induction of apoptosis: C.M. Schempp, et al.; Oncogene 21, 1242 (2002)|6. Dual modulation of striatal acetylcholine release by hyperforin, a constituent of St. John's wort: M.L. Buchholzer, et al.; J. Pharmacol. Exp. Ther. 301, 714 (2002)|7. Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase: D. Albert, et al.; Biochem. Pharmacol. 64, 1767 (2002)|8. Induction and inhibition of cytochromes P450 by the St. John's wort constituent hyperforin in human hepatocyte cultures: B.J. Komoroski; Drug Metab. Dispos. 32, 512 (2004)|9. NMDA receptor-antagonistic properties of hyperforin, a constituent of St. John's Wort: V. Kumar, et al.; J. Pharmacol. Sci. 102, 47 (2006)|10. Hyperforin, a new lead compound against the progression of cancer and leukemia? C. Quiney, et al.; Leukemia 20, 1519 (2006)|11. Hyperforin-a key constituent of St. John's wort specifically activates TRPC6 channels: K. Leuner, et al.; FASEB J. 21, 4101 (2007)|12. Phloroglucinol derivatives guttiferone G, aristoforin, and hyperforin: inhibitors of human sirtuins SIRT1 and SIRT2: C. Gey, et al.; Angew. Chem. Int. Ed. Engl. 46, 5219 (2007)|13. In vitro antimalarial activity of hyperforin, a prenylated acylphloroglucinol. A structure-activity study: L. Verotta, et al.; Bioorg. Med. Chem. Lett. 17, 1544 (2007)|14. Hyperforin is a novel type of 5-lipoxygenase inhibitor with high efficacy in vivo: C. Feisst, et al.; Cell. Mol. Life Sci. 66, 2759 (2009)|15. Neurobiological effects of Hyperforin and its potential in Alzheimer's disease therapy: T.N. Griffith, et al.; Curr. Med. Chem. 17, 391 (2010)USBio References
No references available