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7,4'-Di-O-methylapigenin

CAS# 5128-44-9

7,4'-Di-O-methylapigenin

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Quality Control of 7,4'-Di-O-methylapigenin

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Chemical structure

7,4'-Di-O-methylapigenin

3D structure

Chemical Properties of 7,4'-Di-O-methylapigenin

Cas No. 5128-44-9 SDF Download SDF
PubChem ID 5281601 Appearance Yellow powder
Formula C17H14O5 M.Wt 298.3
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms 4',7-Dimethoxy-5-Hydroxyflavone
Solubility DMSO : 5 mg/mL (16.76 mM; Need ultrasonic)
Chemical Name 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
SMILES COC1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC)O
Standard InChIKey LZERJKGWTQYMBB-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 7,4'-Di-O-methylapigenin

1 Aquilaria sp. 2 Artemisia sp. 3 Citrus sp. 4 Daphne sp. 5 Kaempferia sp. 6 Lonicera sp. 7 Rosmarinus sp. 8 Scutellaria sp. 9 Turnera sp.

Biological Activity of 7,4'-Di-O-methylapigenin

Description1. Apigenin 7, 4'-dimethyl ether (7,4'-Di-O-methylapigenin) can inhibit α-glucosidase and α-amylase enzymes and enhance 2-NBDG uptake in L6 cells, it has hypolipidemic effect on mouse pre-adipocyte (3T3L1) cell lines.

7,4'-Di-O-methylapigenin Dilution Calculator

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7,4'-Di-O-methylapigenin Molarity Calculator

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Preparing Stock Solutions of 7,4'-Di-O-methylapigenin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3523 mL 16.7616 mL 33.5233 mL 67.0466 mL 83.8082 mL
5 mM 0.6705 mL 3.3523 mL 6.7047 mL 13.4093 mL 16.7616 mL
10 mM 0.3352 mL 1.6762 mL 3.3523 mL 6.7047 mL 8.3808 mL
50 mM 0.067 mL 0.3352 mL 0.6705 mL 1.3409 mL 1.6762 mL
100 mM 0.0335 mL 0.1676 mL 0.3352 mL 0.6705 mL 0.8381 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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Background on 7,4'-Di-O-methylapigenin

The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml). IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2] In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2] In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1]

References:
[1]. Alvarez, M.E. et al.Phytochemical study and anti-inflammatory properties of Lampaya hieronymi Schum. ex Moldenke.Farmaco. Jun-Jul;55(6-7):502-5.doi:10.1016/S0014-827X(00)00067-7(2000). [2]. Mangoyi, R., Midiwo, J. & Mukanganyama, S. Isolation and characterization of an antifungal compound 5-hydroxy-7,4'-dimethoxyflavone from Combretum zeyheri. BMC complementary and alternative medicine 15, 405, doi:10.1186/s12906-015-0934-7 (2015).

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References on 7,4'-Di-O-methylapigenin

Effect on oxidative stress, glucose uptake level and lipid droplet content by Apigenin 7, 4'-dimethyl ether isolated from Piper longum L.[Pubmed:26028738]

J Food Sci Technol. 2015 Jun;52(6):3561-70.

Piper longum L. (Family: Piperaceae), is a widely used herb in several Ayurvedic formulations prescribed for various diseases. Potential of the plant material as an antidiabetic and cardio protective agent has not been evaluated so far. In the study, we designed experiments to evaluate antioxidant, glucose uptake potential and lipid content regulating potential of extracts and compound from P. longum fruits. Solvent extracts from Piper longum fruits using hexane, ethyl acetate, methanol, 70 % methanol-water were taken and apigenin 7, 4'-dimethyl ether (ADE) was isolated from ethyl acetate extract. Antioxidant activity, glucose uptake potential and adipocyte differentiation assay was performed with extract and pure compound. Antioxidant activity in terms of TRP (196.03 mug/mg GAE), DPPH assay (IC50-173.09 mug/mL), hydroxyl radical scavenging assay (IC50-20.42 mug/mL), inhibiting LDL oxidation (IC50-51.99 mug/mL) and to enhance SOD activity (25.3 %) was higher in ethyl acetate extract (EAP). Phenolic and flavonoid content was measured and showed a positive correlation with antioxidant activity. Presence of apigenin 7, 4'-dimethyl ether (ADE) and piperine (Pip) in EAP was determined by HPTLC analysis and was isolated. ADE inhibited alpha-glucosidase and alpha-amylase enzymes and enhanced 2-NBDG uptake in L6 cells. Hypolipidemic effect of ADE on mouse pre-adipocyte (3T3L1) cell lines also showed a dose dependent reduction on lipid droplet content and effective concentration range was determined as 1-2.5 mug/mL. The results suggested that Piper longum fruits can provide a natural source of antioxidants with antidiabetic and anti obesity potential.

Five new flavone 5-O-glycosides from Lethedon tannaensis: lethedosides and lethediosides.[Pubmed:10075750]

J Nat Prod. 1999 Feb;62(2):241-3.

Five new 7-methoxy-flavone 5-O-glycosides were isolated from a cytotoxic MeOH extract of Lethedon tannaensis, and the structures were elucidated by 2D NMR spectral analysis and by chemical methods. Lethedosides A (1), B (2), and C (3) were 5-O-glucosides of 7,3', 4'-tri-O-methylluteolin, 7,3',4',5'-tetra-O-methyltricetin, and 7,3', 4'-tri-O-methytricetin, respectively; lethediosides A (4) and B (5) and a known compound 6 were 5-O-xylosylglucosides of 7,3', 4'-tri-O-methylluteolin, 7,3',4',5'-tetra-O-methyltricetin, and 7, 4'-di-O-methylapigenin, respectively. These flavonoids were either inactive or weakly active against KB tumor cells, in contrast to previously isolated flavones from the same plant.

Description

The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C.

Keywords:

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