Centaureidin

CAS# 17313-52-9

Centaureidin

Catalog No. BCN2575----Order now to get a substantial discount!

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Quality Control of Centaureidin

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Chemical structure

Centaureidin

3D structure

Chemical Properties of Centaureidin

Cas No. 17313-52-9 SDF Download SDF
PubChem ID 5315773 Appearance Powder
Formula C18H16O8 M.Wt 360.31
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxychromen-4-one
SMILES COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)O)OC)O)OC)O
Standard InChIKey BZXULYMZYPRZOG-UHFFFAOYSA-N
Standard InChI InChI=1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3
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 Centaureidin

The herbs of Eupatorium fortunei Turcz.

Biological Activity of Centaureidin

Description1. Centaureidin augments IFN-gamma promoter activity by approximately four-fold. 2. Centaureidin inhibits dendrite outgrowth from melanocytes by activating Rho, resulting in the inhibition of melanosome transfer from melanocytes to keratinocytes. 3. Centaureidin shows potential vasorelaxant activity.
TargetsPotassium Channel | IFN-γ

Centaureidin Dilution Calculator

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Centaureidin Molarity Calculator

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Preparing Stock Solutions of Centaureidin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7754 mL 13.8769 mL 27.7539 mL 55.5078 mL 69.3847 mL
5 mM 0.5551 mL 2.7754 mL 5.5508 mL 11.1016 mL 13.8769 mL
10 mM 0.2775 mL 1.3877 mL 2.7754 mL 5.5508 mL 6.9385 mL
50 mM 0.0555 mL 0.2775 mL 0.5551 mL 1.1102 mL 1.3877 mL
100 mM 0.0278 mL 0.1388 mL 0.2775 mL 0.5551 mL 0.6938 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 Centaureidin

Preliminary study of the potential vasodilator effects on rat aorta of centaurein and centaureidin, two flavonoids from Centaurea corcubionensis.[Pubmed:9580164]

Planta Med. 1998 Mar;64(2):116-9.

In this work, the potential vasorelaxant activity of centaurein and Centaureidin, two flavonoids from Centaurea corcubionensis, were studied for the first time in rat aorta. Centaureidin (10 microM-0.1 mM) totally relaxed, in a concentration-dependent manner and with almost equal effectiveness, the contractions induced by NA (IC50 = 16.7 +/- 1.9 microM) or by a high K+ concentration (IC50 = 16.1 +/- 3.1 microM) in intact rat aortic rings. Mechanical removal of endothelium did not significantly modify the vasoralexant effects of this flavone (IC50 = 20.8 +/- 2.4 microM for NA; IC50 = 21 +/- 2.9 microM for K+). On the other hand, centaurein (1 microM-0.1 mM) had no effect on NA- and high K(+)-induced contractions in rubbed and intact rat aortic rings. These results indicate that substitution by glucose in the chemical structure of Centaureidin leads to the loss of its vasodilator activity.

Flavonoids, centaurein and centaureidin, from Bidens pilosa, stimulate IFN-gamma expression.[Pubmed:17408892]

J Ethnopharmacol. 2007 Jun 13;112(2):232-6.

Bidens pilosa is used as an ethnical medicine for bacterial infection or immune modulation in Asia, America and Africa. Here, we employed an IFN-gamma promoter-driven luciferase reporter construct and T cells to characterize immunomodulatory compounds from this plant based on a bioactivity-guided isolation principle. We found that PHA, a positive control, caused a six-fold increase in IFN-gamma promoter activity. In contrast, hot water crude extracts from Bidens pilosa and its butanol subfraction increased IFN-gamma promoter activity to two- and six-fold, respectively. Finally, centaurein (EC(50)=75 microg/ml) and its aglycone, Centaureidin (EC(50)=0.9 microg/ml), isolated from this butanol subfraction, augmented IFN-gamma promoter activity by approximately four-fold. Consistent with the role of centaurein or its aglycone in IFN-gamma regulation, we showed that centaurein induced the activity of NFAT and NFkappaB enhancers, located within the IFN-gamma promoter, in Jurkat cells. Overall, our results showed that centaurein regulated IFN-gamma transcription, probably via NFAT and NFkappaB in T cells.

Centaureidin promotes dendrite retraction of melanocytes by activating Rho.[Pubmed:16476521]

Biochim Biophys Acta. 2006 Mar;1760(3):487-94.

Melanosomes synthesized within melanocytes are transferred to keratinocytes through dendrites, resulting in a constant supply of melanin to the epidermis, and this process determines skin pigmentation. During screening for inhibitors of melanosome transfer, we found a novel reagent, Centaureidin, that induces significant morphological changes in normal human epidermal melanocytes and inhibits melanocyte dendrite elongation, resulting in a reduction of melanosome transfer in an in vitro melanocyte-keratinocyte co-culture system. Since members of the Rho family of small GTP-binding proteins act as master regulators of dendrite formation, and activated Rho promotes dendrite retraction, we studied the effects of Centaureidin on the small GTPases. In in vitro binding assay, Centaureidin activated Rho and furthermore, a Rho inhibitor (C. botulinum C3 exoenzyme), a Rho kinase inhibitor (Y27632) and a small GTPase inhibitor (Toxin B) blocked dendrite retraction induced by Centaureidin. These results suggest Centaureidin could act via the Rho signaling pathway, and it may directly or indirectly activate Rho. Thus, Centaureidin appears to inhibit dendrite outgrowth from melanocytes by activating Rho, resulting in the inhibition of melanosome transfer from melanocytes to keratinocytes.

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