AdipoGen Life Sciences

Hyperforin . DCHA

CHF 150.00

In stock

AG-CN2-0008-C500500 µgCHF 150.00

AG-CN2-0008-M0011 mgCHF 210.00

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Product Details
Synonyms	HPF; (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
Product Type	Chemical
Properties
Formula	C₃₅H₅₁O₄ . C₁₂H₂₄N
MW	535.8 . 182.3
CAS	238074-03-8
Source/Host Chemicals	Isolated from St. John's wort (Hypericum perforatum).
Purity Chemicals	≥97% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in 100% ethanol, methanol or DMSO.
Other Product Data	The DCHA salt stabilizes hyperforin which normally has only a short shelf life.
InChi Key	ZUYCAROZOLUHJY-DNSWOBEMSA-N
Smiles	C1CCC(CC1)NC1CCCCC1.CC(C)C(=O)[C@@]12C(O)=C(CC=C(C)C)C(=O)[C@@](CC=C(C)C)(C[C@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C2=O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep under inert gas. Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Key constituent of St. John's wort.
Shows properties of potential pharmacological interest, including antibacterial [1], anti-malarial [13], anti-inflammatory [7, 14], anti-cancer and anti-angiogenic effects [5, 10].
Anti-depressant and anxiolytic compound [3].
Specific activator of TRPC6 channels [11].
Inhibits the re-uptake of neurotransmitters in synapses (serotonin, norepinephrine, dopamine, GABA, glutamate) [4].
Activator of the pregnane X receptor (PXR) [2].
Regulates expression of the cytochrome P450 CYP3A4 and CYP2C9 and hepatic drugs metabolism [8].
Potential anti-Alzheimer compound [6, 9, 15].
Potent SIRT1 (sirtuin 1) and SIRT2 (sirtuin 2) inhibitor [12].
Based on the anti-inflammatory activity of Hyperforin and its simultaneous blockade of multiple signaling pathways, such as IFN‐γ/IL‐1β/TNF‐α, JAK/STAT, NF‐κB and MAPK it has been suggested a valuable agent for cytokine storm treatment during COVID-19 [16].
Hyperforin targets glutathione peroxidase-4 (GPX-4).
Enhances heme oxygenase-1 (HO-1) expression

Product References

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)
St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor: L.B. Moore, et al.; PNAS 97, 7500 (2000)
Hyperforin-antidepressant activity by a novel mechanism of action: W.E. Müller, et al.; Pharmacopsychiatry 34 (Suppl 1), S98 (2001)
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)
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)
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)
Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase: D. Albert, et al.; Biochem. Pharmacol. 64, 1767 (2002)
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)
NMDA receptor-antagonistic properties of hyperforin, a constituent of St. John's Wort: V. Kumar, et al.; J. Pharmacol. Sci. 102, 47 (2006)
Hyperforin, a new lead compound against the progression of cancer and leukemia? C. Quiney, et al.; Leukemia 20, 1519 (2006)
Hyperforin-a key constituent of St. John's wort specifically activates TRPC6 channels: K. Leuner, et al.; FASEB J. 21, 4101 (2007)
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)
In vitro antimalarial activity of hyperforin, a prenylated acylphloroglucinol. A structure-activity study: L. Verotta, et al.; Bioorg. Med. Chem. Lett. 17, 1544 (2007)
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)
Neurobiological effects of Hyperforin and its potential in Alzheimer's disease therapy: T.N. Griffith, et al.; Curr. Med. Chem. 17, 391 (2010)
Can Hypericum perforatum (SJW) prevent cytokine storm in COVID‐19 patients? P. Masiello, et al.; Phytother Res. (Epub ahead of print) (2020)
Hyperforin Elicits Cytostatic/Cytotoxic Activity in Human Melanoma Cell Lines, Inhibiting Pro-Survival NF-κB, STAT3, AP1 Transcription Factors and the Expression of Functional Proteins Involved in Mitochondrial and Cytosolic Metabolism: A. Cardile, et al.; Int. J. Mol. Sci. 24, 1263 (2023)
Hyperforin Enhances Heme Oxygenase-1 Expression Triggering Lipid Peroxidation in BRAF-Mutated Melanoma Cells and Hampers the Expression of Pro-Metastatic Markers: A. Cardile, et al.; Antioxidants 12, 1369 (2023)

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