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5-Hydroxy-3',4',7-trimethoxyflavone

CAS# 29080-58-8

5-Hydroxy-3',4',7-trimethoxyflavone

Catalog No. BCN5194----Order now to get a substantial discount!

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5-Hydroxy-3',4',7-trimethoxyflavone: 5mg $529 In Stock
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Quality Control of 5-Hydroxy-3',4',7-trimethoxyflavone

Number of papers citing our products

Chemical structure

5-Hydroxy-3',4',7-trimethoxyflavone

3D structure

Chemical Properties of 5-Hydroxy-3',4',7-trimethoxyflavone

Cas No. 29080-58-8 SDF Download SDF
PubChem ID 5272653 Appearance Yellow powder
Formula C18H16O6 M.Wt 328.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one
SMILES COC1=C(C=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC)O)OC
Standard InChIKey HIXDQWDOVZUNNA-UHFFFAOYSA-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 5-Hydroxy-3',4',7-trimethoxyflavone

The herbs of Callicarpa bodinieri Levl.

Biological Activity of 5-Hydroxy-3',4',7-trimethoxyflavone

Description5-Hydroxy-3',4',7-trimethoxyflavone has anti-inflammatory, antibacterial and antifungal activities, it also shows moderate antitrypanosomal activity with MIC value of 19.0 ug/ml. 5-Hydroxy-3',4',7-trimethoxyflavone shows prominent inhibitory activity against soybean lipoxygenase, it can significantly inhibit nitric oxide production and induce reduction in the mRNA expressions of inducible nitric oxide synthase and cyclooxygenase-2 in lipopolysaccharide-induced inflammation in RAW 264.7 macrophages.
TargetsLOX | TNF-α | IL Receptor | PGE | COX | NOS | Antifection
In vitro

Protective effect of 5-hydroxy-3′,4′,7-trimethoxyflavone against inflammation induced by lipopolysaccharide in RAW 264.7 macrophage: in vitro study and in silico validation.[Reference: WebLink]

Med. Chem. Res.,2016,25(9):1754-67.

The herb Lippia nodiflora L. (Verbenaceae) has been documented to exhibit anti-inflammatory, antipyretic, antitussive, antidiabetic, anticancer, and antimelanogenesis properties. In the present study, we aimed at evaluating the anti-inflammatory activity of 5-Hydroxy-3',4',7-trimethoxyflavone, a flavonoid from L. nodiflora, using lipopolysaccharide induced inflammation in RAW 264.7 macrophages.
METHODS AND RESULTS:
5-hydroxy-3′,4′,7-trimethoxyflavone significantly inhibited nitric oxide production and demonstrated slight reduction in prostaglandin-E2 level at tested concentrations. The production of pro-inflammatory cytokines, such as TNF-α, IL-6, and IL-1β, were obviously reduced by 5-Hydroxy-3',4',7-trimethoxyflavone in a concentration-dependent manner. Moreover, 5-Hydroxy-3',4',7-trimethoxyflavone significantly induced reduction in the mRNA expressions of inducible nitric oxide synthase and cyclooxygenase-2, representing that inhibition occurs at the transcriptional level. In addition, we performed molecular docking and molecular dynamic simulations to study the interaction of 5-Hydroxy-3',4',7-trimethoxyflavone with inflammatory mediators such as inducible nitric oxide synthase and cyclooxygenase-2. Docking study showed its hydrogen bond interactions with key residues in the active site of inducible nitric oxide synthase and cyclooxygenase-2, enlightening its possible binding mode at the molecular level. The results of molecular dynamic simulations showed the stability of complexes and their interactions.
CONCLUSIONS:
Taken together, these findings envisage 5-Hydroxy-3',4',7-trimethoxyflavone as a potential candidate molecule for the progress of therapeutic strategy against inflammation-related diseases.

Antifungal Flavonoids from Ballota glandulosissima.[Reference: WebLink]

Pharm. Biol.,2008, 41(7):483-6.

The flavonoids kumatakenin (1), pachypodol (2), 5-Hydroxy-3',4',7-trimethoxyflavone (3), velutin (4), salvigenin (5), retusin (6) and corymbosin (7) have been isolated from the aerial parts of Ballota glandulosissima Hub.-Mor & Patzak. Among them, 2–4 and 7 have not been reported previously in the genus Ballota.
METHODS AND RESULTS:
The antibacterial and antifungal activities of 1–4 and 6 were tested against Bacillus subtilis, Staphylococcus aureus, Staphylococcus faecalis, Echerichia coli, Pseudomonas aeruginosa, Candida albicans, Candida krusei and Candida galabrata.

Anti-infective Activities of Secondary Metabolites from Vitex pinnata.[Reference: WebLink]

J.Appl. Pharm. Sci.,2016,6(1):102-6.

The phytochemical investigation of Vitex pinnata led to the isolation of a mixture of steroids β-sitosterol and stigmasterol (1a and 1b) and three known flavonoid identified as 5-Hydroxy-3',4',7-trimethoxyflavone(2), 5-hydroxy-7,4’-dimethoxy-flavone (3) and 5-hydroxy-3,3’,4’,7-tetramethoxyflavone (4). The structures of all isolated compounds were carried out by NMR and mass spectrometry.
METHODS AND RESULTS:
The isolated compounds were evaluated for their anti-infective activities against Trypanosoma brucei brucei and Microbacterium marinum. Compound 1-4 showed moderate antitrypanosomal activity with MIC values of 6.25μg/ml, 19.0, 21.0 and 17.0μM, respectively while no activity observed on anti-mycobacterial.
CONCLUSIONS:
This study is the first to report the presence of three flavones and their antitrypanosomal activity from V. pinnata.

Protocol of 5-Hydroxy-3',4',7-trimethoxyflavone

Kinase Assay

Anti-allergenic activity of polymethoxyflavones from Kaempferia parviflora.[Reference: WebLink]

In vitro, fluorescence-quenching and computational studies on the interaction between lipoxygenase and 5-hydroxy-3',4',7-trimethoxyflavone from Lippia nodiflora L.[Pubmed: 26155726]

J Recept Signal Transduct Res. 2015 Jul 9:1-9.

The folk use of L. nodiflora was validated using the isolated natural compound, 5-Hydroxy-3',4',7-trimethoxyflavone (HTMF) by in vitro, fluorescence spectroscopic and molecular modeling studies with lipoxygenase (LOX), because LOX plays an essential role in inflammatory responses.
METHODS AND RESULTS:
In this perspective, the methanol extract and 5-Hydroxy-3',4',7-trimethoxyflavone are shown to demonstrate prominent inhibitory activity against soybean lipoxygenase, with an IC50 value of 21.12 and 23.97 µg/ml, respectively. The data obtained from the spectroscopic method revealed that the quenching of intrinsic fluorescence of LOX is produced as a result of the complex formation of LOX-5-Hydroxy-3',4',7-trimethoxyflavone. The binding mode analysis of 5-Hydroxy-3',4',7-trimethoxyflavone within the LOX enzyme suggested that hydrogen bond formation, hydrophobic interaction and π-π stacking could account for the binding of 5-Hydroxy-3',4',7-trimethoxyflavone. Molecular dynamics results indicated the interaction of 5-Hydroxy-3',4',7-trimethoxyflavone with LOX and the stability of ligand-enzyme complex was maintained throughout the simulation.
CONCLUSIONS:
The computational results are reliable with experimental facts and provided a good representation for understanding the binding mode of 5-Hydroxy-3',4',7-trimethoxyflavone inside the active site of lipoxygenase enzyme.

Journal of Functional Foods, 2015,13:100-7.

The inhibitory effects of 13 polymethoxyflavones (PMFs) obtained from Kaempferia parviflora extracts were evaluated on RBL-2H3 cell degranulation.
METHODS AND RESULTS:
These flavones suppressed antigen-induced degranulation in RBL-2H3 cells. 5-Hydroxy-3',4',7-trimethoxyflavone (KP02) and 5,3′-dihydroxy-3,7,4′,-trimethoxyflavone (KP10) showed potent inhibitory activities. KP10 significantly suppressed calcium ionophores, such as A23187 and 2,5-ditert-butylhydroquinone, which promoted calcium influx from the outside of cells and from the endoplasmic reticulum, respectively. However, these activities did not fully explain the PMFs' effects. Immunoblot analysis of KP02 and KP10 showed that the inhibitory effects were attributable to the downregulation of PLCγ1 kinase phosphorylation in the signaling pathways involved in degranulation. The phosphorylation levels of Syk were also suppressed by the addition of KP10. KP02 and KP10 treatment to the cells did not affect the high affinity IgE receptor (FcεRI) levels inside RBL-2H3 cells, but they suppressed the FcεRI levels in the plasma membrane.
CONCLUSIONS:
Therefore, K. parviflora PMFs have multiple degranulation mechanisms to suppress RBL-2H3 cells and would be beneficial for alleviating type I allergy symptoms.

5-Hydroxy-3',4',7-trimethoxyflavone Dilution Calculator

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Preparing Stock Solutions of 5-Hydroxy-3',4',7-trimethoxyflavone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.046 mL 15.23 mL 30.4599 mL 60.9199 mL 76.1499 mL
5 mM 0.6092 mL 3.046 mL 6.092 mL 12.184 mL 15.23 mL
10 mM 0.3046 mL 1.523 mL 3.046 mL 6.092 mL 7.615 mL
50 mM 0.0609 mL 0.3046 mL 0.6092 mL 1.2184 mL 1.523 mL
100 mM 0.0305 mL 0.1523 mL 0.3046 mL 0.6092 mL 0.7615 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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References on 5-Hydroxy-3',4',7-trimethoxyflavone

In vitro, fluorescence-quenching and computational studies on the interaction between lipoxygenase and 5-hydroxy-3',4',7-trimethoxyflavone from Lippia nodiflora L.[Pubmed:26155726]

J Recept Signal Transduct Res. 2015;35(6):569-77.

Lippia nodiflora L. is extensively used in traditional medicine for several medicinal purposes, including their use in inflammatory disorders. In this study, the folk use of L. nodiflora was validated using the isolated natural compound, 5-hydroxy-3',4',7-trimethoxyflavone (HTMF) by in vitro, fluorescence spectroscopic and molecular modeling studies with lipoxygenase (LOX), because LOX plays an essential role in inflammatory responses. In this perspective, the methanol extract and HTMF are shown to demonstrate prominent inhibitory activity against soybean lipoxygenase, with an IC50 value of 21.12 and 23.97 microg/ml, respectively. The data obtained from the spectroscopic method revealed that the quenching of intrinsic fluorescence of LOX is produced as a result of the complex formation of LOX-HTMF. The binding mode analysis of HTMF within the LOX enzyme suggested that hydrogen bond formation, hydrophobic interaction and pi-pi stacking could account for the binding of HTMF. Molecular dynamics results indicated the interaction of HTMF with LOX and the stability of ligand-enzyme complex was maintained throughout the simulation. The computational results are reliable with experimental facts and provided a good representation for understanding the binding mode of HTMF inside the active site of lipoxygenase enzyme.

Description

7,3',4'-Tri-O-methylluteolin (5-Hydroxy-3',4',7-trimethoxyflavone) is a flavonoid from the herb Lippia nodiflora L. (Verbenaceae) which has been documented to exhibit anti-inflammatory, antipyretic, antitussive, antidiabetic, anticancer, and antimelanogenesis properties. 7,3',4'-Tri-O-methylluteolin obviously reduces the prodn of pro-inflammatory cytokines, such as TNF-α, IL-6, and IL-1β in a concentration-dependent manner. 7,3',4'-Tri-O-methylluteolin significantly induces reduction in the mRNA expressions of inducible nitric oxide synthase and cyclooxygenase-2, representing that inhibition occurs at the transcriptional level.

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