6,7,8-Trimethoxycoumarin | CAS:6035-49-0

6,7,8-Trimethoxycoumarin

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Description:

6,7,8-Trimethoxycoumarin has antiviral activity, it shows high anti-HRV-2 effect , with IC (50) value of 11.98 muM. It also can improve gastroprotective effects.

Targets:

P450 (e.g. CYP17) | AChR | Antifection | HRV

In vitro:

Planta Med. 2009 Feb;75(3):195-204.

In silico target fishing for rationalized ligand discovery exemplified on constituents of Ruta graveolens.[Pubmed: 19096995]

The identification of targets whose interaction is likely to result in the successful treatment of a disease is of growing interest for natural product scientists.
METHODS AND RESULTS:
In the current study we performed an exemplary application of a virtual parallel screening approach to identify potential targets for 16 secondary metabolites isolated and identified from the aerial parts of the medicinal plant RUTA GRAVEOLENS L. Low energy conformers of the isolated constituents were simultaneously screened against a set of 2208 pharmacophore models generated in-house for the IN SILICO prediction of putative biological targets, i. e., target fishing. Based on the predicted ligand-target interactions, we focused on three biological targets, namely acetylcholinesterase (AChE), the human rhinovirus (HRV) coat protein and the cannabinoid receptor type-2 (CB (2)). For a critical evaluation of the applied parallel screening approach, virtual hits and non-hits were assayed on the respective targets. For AChE the highest scoring virtual hit, arborinine, showed the best inhibitory IN VITRO activity on AChE (IC (50) 34.7 muM). Determination of the anti-HRV-2 effect revealed 6,7,8-Trimethoxycoumarin and arborinine to be the most active antiviral constituents with IC (50) values of 11.98 muM and 3.19 muM, respectively. Of these, arborinine was predicted virtually. Of all the molecules subjected to parallel screening, one virtual CB (2) ligand was obtained, i. e., rutamarin. Interestingly, in experimental studies only this compound showed a selective activity to the CB (2) receptor ( Ki of 7.4 muM) by using a radioligand displacement assay.
CONCLUSIONS:
The applied parallel screening paradigm with constituents of R. GRAVEOLENS on three different proteins has shown promise as an IN SILICO tool for rational target fishing and pharmacological profiling of extracts and single chemical entities in natural product research.

J Ethnopharmacol. 1999 Dec 15;68(1-3):283-8.

Antiviral flavonoid from Pterocaulon sphacelatum, an Australian Aboriginal medicine.[Pubmed: 10624889]

The antipicornaviral activity of an ethanolic extract of the green aerial parts of the Australian plant Pterocaulon sphacelatum (Labill.) Benth. & Hook. f. ex F. Muell. has been investigated. This plant has been a favoured traditional medicine, used for the treatment of colds by the Australian Aboriginal people.
METHODS AND RESULTS:
Antiviral activity-guided fractionation of the extract of P. sphacelatum using an inhibition of poliovirus-induced cytopathic effect assay, has yielded the antiviral flavonoid chrysosplenol C (3,7,3'-trimethoxy-5,6,4'-trihydroxyflavone). This compound is a 4'-hydroxy-3-methoxyflavone, one of a group of compounds known to be potent and specific inhibitors of picornaviral replication.
CONCLUSIONS:
These compounds inhibit the replication of rhinoviruses, the most frequent causative agent of the common cold. The coumarin 6,7,8-Trimethoxycoumarin was also isolated from the ethanolic extract.

In vivo:

Nutrients. 2015 Mar 13;7(3):1945-64.

Gastroprotective efficacy and safety evaluation of scoparone derivatives on experimentally induced gastric lesions in rodents.[Pubmed: 25781220]

Among these compounds, 5,6,7-trimethoxycoumarin and 6,7,8-Trimethoxycoumarin were found to have gastroprotective activity greater than the standard drug rebamipide; 6-methoxy-7,8-methylenedioxycoumarin, 6-methoxy-7,8-(1-methoxy)-methylenedioxycoumarin, 6,7-methylenedioxycoumarin, and 6,7-(1-methoxy)-methylenedioxycoumarin were found to be equipotent or less potent that of rebamipide. Pharmacological studies suggest that the presence of a methoxy group at position C-5 or C-8 of the scoparone's phenyl ring significantly improves gastroprotective activity, whereas the presence of a dioxolane ring at C-6, C-7, or C-8 was found to have decreased activity.
METHODS AND RESULTS:
In order to assess toxicological safety, two of the potent gastroprotective scoparone derivatives-5,6,7-trimethoxycoumarin and 6,7,8-Trimethoxycoumarin-were examined for their acute toxicity in mice as well as their effect on cytochrome P450 (CYP) enzyme activity. These two compounds showed low acute oral toxicity in adult male and female mice, and caused minimal changes to CYP3A4 and CYP2C9 enzyme activity.
CONCLUSIONS:
These results indicate that compared to other scoparone derivatives, 5,6,7-trimethoxycoumarin and 6,7,8-Trimethoxycoumarin can improve gastroprotective effects, and they have low toxicity and minimal effects on drug-metabolizing enzymes.

6,7,8-Trimethoxycoumarin Description

Source:	The herbs of Viola yedonensis Makino.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

CAS No.	6035-49-0	Price	$288 / 20mg
Catalog No.	CFN97024	Purity	>=98%
Molecular Weight	236.2	Type of Compound	Coumarins
Formula	C₁₂H₁₂O₅	Physical Description	Cryst.
Download	COA MSDS SDF	Similar structural	Comparison (Web) (SDF)

Product Name	6,7,8-Trimethoxycoumarin
CAS No.:	6035-49-0
Catalog No.:	CFN97024
Molecular Formula:	C₁₂H₁₂O₅
Molecular Weight:	236.2 g/mol
Purity:	>=98%
Type of Compound:	Coumarins
Physical Desc.:	Cryst.
Targets:	P450 (e.g. CYP17) \| AChR \| Antifection \| HRV
Source:	The herbs of Viola yedonensis Makino.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Price:	$288 / 20mg
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Antiviral Compound Library Gastro-protective Compound Library Coumarins Compound Library P450 (e.g. CYP17) Inhibitor Library Antifection Inhibitor Library AChR Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	4.2337 mL	21.1685 mL	42.337 mL	84.674 mL	105.8425 mL
5 mM	0.8467 mL	4.2337 mL	8.4674 mL	16.9348 mL	21.1685 mL
10 mM	0.4234 mL	2.1169 mL	4.2337 mL	8.4674 mL	10.5843 mL
50 mM	0.0847 mL	0.4234 mL	0.8467 mL	1.6935 mL	2.1169 mL
100 mM	0.0423 mL	0.2117 mL	0.4234 mL	0.8467 mL	1.0584 mL

CFN99113	Fraxetin	574-84-5	208.17	C₁₀H₈O₅
CFN99747	Fraxin	524-30-1	370.32	C₁₆H₁₈O₁₀
CFN90181	Isofraxidin	486-21-5	222.19	C₁₁H₁₀O₅
CFN98764	Calycanthoside	483-91-0	384.3	C₁₇H₂₀O₁₀
CFN98860	Fraxidin	525-21-3	222.2	C₁₁H₁₀O₅
CFN97024	6,7,8-Trimethoxycoumarin	6035-49-0	236.2	C₁₂H₁₂O₅
CFN70339	Artemicapin C	334007-19-1	206.2	C₁₀H₆O₅