Hyperforin

CAS# 11079-53-1

Hyperforin

Catalog No. BCN8848----Order now to get a substantial discount!

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Quality Control of Hyperforin

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Chemical structure

Hyperforin

3D structure

Chemical Properties of Hyperforin

Cas No. 11079-53-1 SDF Download SDF
PubChem ID 441298 Appearance Powder
Formula C35H52O4 M.Wt 536.80
Type of Compound Miscellaneous Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,5R,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
SMILES CC(C)C(=O)C12C(=O)C(=C(C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C
Standard InChIKey KGSZHKRKHXOAMG-HQKKAZOISA-N
Standard InChI InChI=1S/C35H52O4/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/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Hyperforin

The herbs of Hypericum monogynum

Biological Activity of Hyperforin

DescriptionHyperforin acts as an angiogenesis inhibitor, it as a possible antidepressant component of hypericum extracts. Hyperforin acts as a dual inhibitor of 5-LO and COX-1 in intact cells as well as on the catalytic activity of the crude enzymes, suggesting therapeutic potential in inflammatory and allergic diseases connected to eicosanoids.
TargetsCOX-1 | 5-LO | 5-HT recepter | GABA recepter
In vitro

Hyperforin as a possible antidepressant component of hypericum extracts.[Pubmed: 9718074 ]

Life Sci. 1998;63(6):499-510.


METHODS AND RESULTS:
We demonstrate that the phloroglucinol derivative Hyperforin is not only the major lipophilic chemical constituent of the medicinal plant Hypericum perforatum (St. John's wort) but also a potent uptake inhibitor of serotonin (5-HT), dopamine (DA), noradrenaline (NA), GABA and L-Glutamate with IC50 values of about 0.05-0.10 microg/ml (5-HT, NA, DA, GABA) and about 0.5 microg/ml (L-glutamate) in synaptosomal preparations. Furthermore, potencies of two different hypericum extracts in two conventional pharmacological paradigms useful for the detection of antidepressants (behavioral despair, learned helplessness), closely correlate with their Hyperforin contents. In addition, most till now known neuropharmacological properties of the clinically used hypericum extracts can also be demonstrated with pure Hyperforin.
CONCLUSIONS:
It appears, therefore, that this non-nitrogenous constituent is a possible major active principle responsible for the observed clinical efficacies of the extract as an antidepressant and that it could also be a starting point for drug discovery projects engaged in the search of psychoactive drugs with novel mode of action.

Protocol of Hyperforin

Kinase Assay

Hyperforin acts as an angiogenesis inhibitor.[Pubmed: 16320199]

Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase.[Pubmed: 12445866 ]

Biochem Pharmacol. 2002 Dec 15;64(12):1767-75.

The acylphloroglucinol derivative Hyperforin is the major lipophilic constituent in the herb Hypericum perforatum (St. John's wort). The aim of the present study was to investigate if Hyperforin as well as extracts of H. perforatum can suppresses the activities of 5-lipoxygenase (5-LO) and cyclooxygenases (COX), key enzymes in the formation of proinflammatory eicosanoids from arachidonic acid (AA).
METHODS AND RESULTS:
In freshly isolated human polymorphonuclear leukocytes stimulated with Ca(2+) ionophore A23187, Hyperforin inhibited 5-LO product formation with IC(50) values of about 1-2 microM, in the absence or presence of exogenous AA (20 microM), respectively, being almost equipotent to the well-documented 5-LO inhibitor zileuton (IC(50) = 0.5-1 microM). Experiments with purified human 5-LO demonstrate that Hyperforin is a direct 5-LO inhibitor (IC(50) approximately 90 nM), acting in an uncompetitive fashion. In thrombin- or ionophore-stimulated human platelets, Hyperforin suppressed COX-1 product (12(S)-hydroxyheptadecatrienoic acid) formation with an IC(50) of 0.3 and 3 microM, respectively, being about 3- to 18-fold more potent than aspirin. At similar concentrations, Hyperforin suppressed COX-1 activity in platelets in presence of exogenous AA (20 microM) as well as in cell-free systems. Hyperforin could not interfere with COX-2 product formation and did not significantly inhibit 12- or 15-LO in platelets or leukocytes, respectively.
CONCLUSIONS:
We conclude that Hyperforin acts as a dual inhibitor of 5-LO and COX-1 in intact cells as well as on the catalytic activity of the crude enzymes, suggesting therapeutic potential in inflammatory and allergic diseases connected to eicosanoids.

Planta Med. 2005 Nov;71(11):999-1004.

Hyperforin is a plant compound from Hypericum perforatum that inhibits tumor cell proliferation in vitro by induction of apoptosis. Here, we report that Hyperforin also acts as an angiogenesis inhibitor in vitro and in vivo.
METHODS AND RESULTS:
In vitro, Hyperforin blocked microvessel formation of human dermal microvascular endothelial cells (HDMEC) on a complex extracellular matrix. Furthermore, Hyperforin reduced proliferation of HDMEC in a dose-dependent manner, without displaying toxic effects or inducing apoptosis of the cells. To evaluate the antiangiogenic activity of Hyperforin in vivo, Wistar rats were subcutaneously injected with MT-450 mammary carcinoma cells and were treated with peritumoral injections of Hyperforin or solvent. Hyperforin significantly inhibited tumor growth, induced apoptosis of tumor cells and reduced tumor vascularization, as shown by in situ staining of CD31-positive microvessels in the tumor stroma.
CONCLUSIONS:
These data suggest that, in addition to the induction of tumor cell apoptosis, Hyperforin can also suppress angiogenesis by a direct, non-toxic effect on endothelial cells.

Hyperforin Dilution Calculator

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Hyperforin Molarity Calculator

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Preparing Stock Solutions of Hyperforin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8629 mL 9.3145 mL 18.6289 mL 37.2578 mL 46.5723 mL
5 mM 0.3726 mL 1.8629 mL 3.7258 mL 7.4516 mL 9.3145 mL
10 mM 0.1863 mL 0.9314 mL 1.8629 mL 3.7258 mL 4.6572 mL
50 mM 0.0373 mL 0.1863 mL 0.3726 mL 0.7452 mL 0.9314 mL
100 mM 0.0186 mL 0.0931 mL 0.1863 mL 0.3726 mL 0.4657 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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