Hyperforin . DCHA

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Product Code: AG-CN2-0008
CodeSizePrice
AG-CN2-0008-C500500 ug£110.00
Quantity:
AG-CN2-0008-M0011 mg£170.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C

Images

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Chemical Structure
❮❯

Chemical Structure

Documents

Further Information

Alternate Names/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
Appearance:
White to off-white solid.
CAS:
238074-03-8
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Keep under inert gas.Protect from light.
Hazards:
H302, H312
InChi:
InChI=1S/C35H52O4.C12H23N/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3;11-13H,1-10H2/t27-,33+,34+,35-;/m0./s1
InChiKey:
ZUYCAROZOLUHJY-DNSWOBEMSA-N
Long Description:
Chemical. CAS: 238074-03-8. Formula: C35H51O4 . C12H24N. MW: 535.8 . 182.3. Isolated from St. John's wort (Hypericum perforatum). Key constituent of St. John's wort. Shows properties of potential pharmacological interest, including antibacterial, 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.
MDL:
MFCD04000098
Molecular Formula:
C35H51O4 . C12H24N
Molecular Weight:
535.8 . 182.3
Other data:
The DCHA salt stabilizes hyperforin which normally has only a short shelf life.
Package Type:
Vial
Precautions:
P270, P280, P312
Product 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?gamma/IL?1beta/TNF?alpha, JAK/STAT, NF?kappaB and MAPK it has been suggested a valuable agent for cytokine storm treatment during COVID-19 [16].
Purity:
>97% (HPLC)
Signal word:
Warning
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
Solubility Chemicals:
Soluble in 100% ethanol, methanol or DMSO.
Source / Host:
Isolated from St. John's wort (Hypericum perforatum).
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

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. M?ller, 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)

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