Home >> Research Area >>Natural Products>>Coumarins>> 8-Geranyloxypsoralen

8-Geranyloxypsoralen

CAS# 7437-55-0

8-Geranyloxypsoralen

Catalog No. BCN4296----Order now to get a substantial discount!

Product Name & Size Price Stock
8-Geranyloxypsoralen: 5mg $265 In Stock
8-Geranyloxypsoralen: 10mg Please Inquire In Stock
8-Geranyloxypsoralen: 20mg Please Inquire Please Inquire
8-Geranyloxypsoralen: 50mg Please Inquire Please Inquire
8-Geranyloxypsoralen: 100mg Please Inquire Please Inquire
8-Geranyloxypsoralen: 200mg Please Inquire Please Inquire
8-Geranyloxypsoralen: 500mg Please Inquire Please Inquire
8-Geranyloxypsoralen: 1000mg Please Inquire Please Inquire

Quality Control of 8-Geranyloxypsoralen

Number of papers citing our products

Chemical structure

8-Geranyloxypsoralen

3D structure

Chemical Properties of 8-Geranyloxypsoralen

Cas No. 7437-55-0 SDF Download SDF
PubChem ID 5317564 Appearance White powder
Formula C21H22O4 M.Wt 338.4
Type of Compound Coumarins Storage Desiccate at -20°C
Solubility Soluble in acetonitrile and chloroform
Chemical Name 9-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
SMILES CC(=CCCC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C)C
Standard InChIKey SOVNCTNQAWWYAQ-OQLLNIDSSA-N
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 8-Geranyloxypsoralen

The herbs of Seseli mairei Wolff

Biological Activity of 8-Geranyloxypsoralen

Description8-Geranyloxypsoralen inhibits β-secretase (BACE1) activity in non-competitive manner, with the IC(50) values <25.0 uM, it can induce vasorelaxation on rat arterial tissues. 8-Geranyloxypsoralen possesses nematicidal activities, the median lethal concentrations (LC(50)) is 188.3 mg/ L against B. xylophilus and is 117.5 mg/L against P. redivivus.
TargetsBACE | P450 (e.g. CYP17) | Antifection
In vitro

Nematicidal coumarins from Heracleum candicans Wall.[Pubmed: 18569707 ]

Nat Prod Res. 2008 May 20;22(8):666-71.

The root extract of Heracleum candicans Wall. exhibited antagonistic activities against nematodes Bursaphelenchus xylophilus (Steiner et Buhrer) Nickle and Panagrellus redivivus (Linn.) Goodey.
METHODS AND RESULTS:
Through bioassay-guided fractionations, three coumarins were obtained from the extract of H. candicans and determined to be 8-Geranyloxypsoralen (1), imperatorin (2), and heraclenin (3) based on spectra data. All three compounds possessed nematicidal activities against the two tested nematodes. The median lethal concentrations (LC(50)) of compounds 1-3 at 72 h were 188.3, 161.7, and 114.7 mg L(-1) respectively against B. xylophilus and were 117.5, 179.0, and 148.7 mg L(-1) respectively against P. redivivus.
CONCLUSIONS:
This is the first report about species in the Umbelliferae family that possesses nematicidal activity.

Vasodilation and radical-scavenging activity of imperatorin and selected coumarinic and flavonoid compounds from genus Casimiroa.[Pubmed: 24309287]

Phytomedicine. 2014 Apr 15;21(5):586-94.

Hypertension is a very widespread condition which is not strictly considered as an illness but if not countered, progressively causes damage to all tissues and loss in their functionality. For this reason the find of new antihypertensive agents is prominent and medicinal plants and their derivatives are valuable for the purpose. The genus Casimiroa (Rutaceae) includes plants from Central America and Mexico; among these, Casimiroa edulis Llave et Lex. and Casimiroa pubescens Ramirez are the most relevant species, even for their medicinal uses. The decoction of leaves and seeds is traditionally taken as a tea mainly to lower blood pressure.
METHODS AND RESULTS:
The object of this research was the study of vascular activity of coumarinic and flavonoid compounds isolated from seeds of Casimiroa spp. in comparison with Casimiroa edulis and Casimiroa pubescens extracts. The phenolic compounds isolated from Casimiroa were herniarin (Her), imperatorin (Imp), 8-Geranyloxypsoralen (GOP) and 5,6,2',3',4'-pentamethoxyflavone (PMF). All these compounds induced vasorelaxation on rat arterial tissues although with different effectiveness. To study the cellular mechanisms of the vasorelaxation exhibited by imperatorin, we used selective inhibitors of different receptors and enzymes, such as atropine, pyrilamine, nifedipine, L-NAME and DETC. In a further step of this research, we evaluated the radical-scavenging activity of Casimiroa extracts and isolated compounds by means of DPPH assay. In general, we observed that the scavenging activities increased in a concentration-dependent manner for all substances. The phenolic compounds highlight a synergism of vasodilation and antioxidant activity which may be very useful in the management of cardiovascular diseases.
CONCLUSIONS:
Among the evaluated compounds, imperatorin shows a significant vasorelaxant activity even higher than acetylcholine and similar to nitrite, and also useful antiradical capabilities. All these properties suggest its possible role against hypertension and vasculopathies, even if in vivo studies are needed to determine the actual applications.

Protocol of 8-Geranyloxypsoralen

Kinase Assay

Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.[Pubmed: 22222157]

Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4.[Pubmed: 16481174]

Bioorg Med Chem. 2006 Jun 1;14(11):3865-71.

Furanocoumarins have been shown to inhibit CYP3A4 in vitro with varying degrees of potency.
METHODS AND RESULTS:
In this study, we report the effects of a series of novel furanocoumarins based on the naturally occurring derivative 8-geranylepoxypsoralen which has been shown to be a more potent inhibitor of CYP3A4 than its 5-position-substituted counterpart bergamottin. Compounds were designed, synthesised and tested for their ability to inhibit CYP3A4 activity in human liver microsomes using testosterone as the marker substrate. Both the saturated and unsaturated phenolic furanocoumarin derivatives were found to be inactive. However, the 8-alkyloxy-furanocoumarin analogues were shown to inhibit CYP3A4 activity in a dose dependent manner, with IC(50) values ranging from 0.78+/-0.11 to 3.93+/-0.53 microM.
CONCLUSIONS:
The reduced furan derivative dihydro-8-Geranyloxypsoralen showed a 4-fold decrease in inhibitory potency, suggesting that the furan moiety plays a role in the interaction between these compounds and CYP3A4.

Bioorg Med Chem. 2012 Jan 15;20(2):784-8.

The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity.
METHODS AND RESULTS:
Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC(50) value of 9.9 μM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5-methoxypsoralen (35), 8-Geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC(50) values <25.0 μM.
CONCLUSIONS:
Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.

8-Geranyloxypsoralen Dilution Calculator

Concentration (start)
x
Volume (start)
=
Concentration (final)
x
Volume (final)
 
 
 
C1
V1
C2
V2

calculate

8-Geranyloxypsoralen Molarity Calculator

Mass
=
Concentration
x
Volume
x
MW*
 
 
 
g/mol

calculate

Preparing Stock Solutions of 8-Geranyloxypsoralen

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9551 mL 14.7754 mL 29.5508 mL 59.1017 mL 73.8771 mL
5 mM 0.591 mL 2.9551 mL 5.9102 mL 11.8203 mL 14.7754 mL
10 mM 0.2955 mL 1.4775 mL 2.9551 mL 5.9102 mL 7.3877 mL
50 mM 0.0591 mL 0.2955 mL 0.591 mL 1.182 mL 1.4775 mL
100 mM 0.0296 mL 0.1478 mL 0.2955 mL 0.591 mL 0.7388 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.

Organizitions Citing Our Products recently

 
 
 

Calcutta University

University of Minnesota

University of Maryland School of Medicine

University of Illinois at Chicago

The Ohio State University

University of Zurich

Harvard University

Colorado State University

Auburn University

Yale University

Worcester Polytechnic Institute

Washington State University

Stanford University

University of Leipzig

Universidade da Beira Interior

The Institute of Cancer Research

Heidelberg University

University of Amsterdam

University of Auckland
TsingHua University
TsingHua University
The University of Michigan
The University of Michigan
Miami University
Miami University
DRURY University
DRURY University
Jilin University
Jilin University
Fudan University
Fudan University
Wuhan University
Wuhan University
Sun Yat-sen University
Sun Yat-sen University
Universite de Paris
Universite de Paris
Deemed University
Deemed University
Auckland University
Auckland University
The University of Tokyo
The University of Tokyo
Korea University
Korea University
Featured Products
New Products
 

References on 8-Geranyloxypsoralen

Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4.[Pubmed:16481174]

Bioorg Med Chem. 2006 Jun 1;14(11):3865-71.

Furanocoumarins have been shown to inhibit CYP3A4 in vitro with varying degrees of potency. In this study, we report the effects of a series of novel furanocoumarins based on the naturally occurring derivative 8-geranylepoxypsoralen which has been shown to be a more potent inhibitor of CYP3A4 than its 5-position-substituted counterpart bergamottin. Compounds were designed, synthesised and tested for their ability to inhibit CYP3A4 activity in human liver microsomes using testosterone as the marker substrate. Both the saturated and unsaturated phenolic furanocoumarin derivatives were found to be inactive. However, the 8-alkyloxy-furanocoumarin analogues were shown to inhibit CYP3A4 activity in a dose dependent manner, with IC(50) values ranging from 0.78+/-0.11 to 3.93+/-0.53 microM. The reduced furan derivative dihydro-8-Geranyloxypsoralen showed a 4-fold decrease in inhibitory potency, suggesting that the furan moiety plays a role in the interaction between these compounds and CYP3A4.

Nematicidal coumarins from Heracleum candicans Wall.[Pubmed:18569707]

Nat Prod Res. 2008 May 20;22(8):666-71.

The root extract of Heracleum candicans Wall. exhibited antagonistic activities against nematodes Bursaphelenchus xylophilus (Steiner et Buhrer) Nickle and Panagrellus redivivus (Linn.) Goodey. Through bioassay-guided fractionations, three coumarins were obtained from the extract of H. candicans and determined to be 8-Geranyloxypsoralen (1), imperatorin (2), and heraclenin (3) based on spectra data. All three compounds possessed nematicidal activities against the two tested nematodes. The median lethal concentrations (LC(50)) of compounds 1-3 at 72 h were 188.3, 161.7, and 114.7 mg L(-1) respectively against B. xylophilus and were 117.5, 179.0, and 148.7 mg L(-1) respectively against P. redivivus. This is the first report about species in the Umbelliferae family that possesses nematicidal activity.

Structure-activity relationships for naturally occurring coumarins as beta-secretase inhibitor.[Pubmed:22222157]

Bioorg Med Chem. 2012 Jan 15;20(2):784-8.

The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of beta-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC(50) value of 9.9 muM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5-methoxypsoralen (35), 8-Geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC(50) values <25.0 muM. Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.

Description

8-Geranyloxypsoralen is a furanocoumarin isolated from grapefruit, acts as a potent inhibitor of P450 3A4 (CYP3A4) with an IC50 of 3.93 μM.

Keywords:

8-Geranyloxypsoralen,7437-55-0,Natural Products, buy 8-Geranyloxypsoralen , 8-Geranyloxypsoralen supplier , purchase 8-Geranyloxypsoralen , 8-Geranyloxypsoralen cost , 8-Geranyloxypsoralen manufacturer , order 8-Geranyloxypsoralen , high purity 8-Geranyloxypsoralen

Online Inquiry for:

      Fill out the information below

      • Size:Qty: - +

      * Required Fields

                                      Result: