Oroxin A

CAS# 57396-78-8

Oroxin A

Catalog No. BCN1202----Order now to get a substantial discount!

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Chemical structure

Oroxin A

3D structure

Chemical Properties of Oroxin A

Cas No. 57396-78-8 SDF Download SDF
PubChem ID 5320313 Appearance Yellow powder
Formula C21H20O10 M.Wt 432.38
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Oroxin A; 5,6,7-Trihydroxyflavone 7-glucoside
Solubility Soluble in methanol and water
Chemical Name 5,6-dihydroxy-2-phenyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES C1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
Standard InChIKey IPQKDIRUZHOIOM-IAAKTDFRSA-N
Standard InChI InChI=1S/C21H20O10/c22-8-14-17(25)19(27)20(28)21(31-14)30-13-7-12-15(18(26)16(13)24)10(23)6-11(29-12)9-4-2-1-3-5-9/h1-7,14,17,19-22,24-28H,8H2/t14-,17-,19+,20-,21-/m1/s1
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 Oroxin A

1 Scutellaria sp.

Biological Activity of Oroxin A

DescriptionOroxin A is a xanthine oxidase (XO) inhibitor, it exerts its antibreast cancer effects by inducing ER stress-mediated senescence, activating the key stress signaling pathway, and increasing key ER stress genes and expression levels.
TargetsXO
In vitro

Oroxin A inhibits breast cancer cell growth by inducing robust endoplasmic reticulum stress and senescence.[Pubmed: 26599214 ]

Anticancer Drugs. 2016 Mar;27(3):204-15.

Breast cancer is a major cause of cancer death among women. Although various anticancer drugs have been used in clinics, drugs that are effective against advanced and metastatic breast cancer are still lacking and in great demand.
METHODS AND RESULTS:
In this study, we found that Oroxin A, an active component isolated from the herb Oroxylum indicum (L.) Kurz, effectively inhibited the growth of human breast cancer cells MDA-MB-231 and MCF7 by inducing endoplasmic reticulum (ER) stress-mediated senescence. Oroxin A caused breast cancer cell cycle arrest at the G2/M stage, and reorganization of microtubules and actin cytoskeleton accompanied by a decrease in cellular mitosis. ER-specific probe ER-Tracker Red and confocal microscope imaging showed that ER-Tracker Red-positive cells increased in an Oroxin A dosage-dependent manner. In addition, Oroxin A increased cell population with high β-Gal activity and SAHF-positive staining; these data suggest that Oroxin A induces breast cancer cell ER stress and senescence. Mechanistic studies showed that Oroxin A led to a significant increase in intracellular reactive oxygen species levels, promoted expression of ER stress markers ATF4 and GRP78, and increased the phosphorylation of a key stress-response signaling protein p38, resulting in an ER stress-mediated senescence.
CONCLUSIONS:
Taken together, our data indicate that Oroxin A exerts its antibreast cancer effects by inducing ER stress-mediated senescence, activating the key stress p38 signaling pathway, and increasing key ER stress genes ATF4 and GRP78 expression levels.

Protocol of Oroxin A

Structure Identification
Yao Xue Xue Bao. 2006 Apr;41(4):380-4.

[Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS].[Pubmed: 16856488]

To establish a comprehensive HPLC analytical method of Huanglianjiedu decoction.
METHODS AND RESULTS:
This study was performed by HPLC-UV/MS to identify the chemical constituents of the whole and individual herbs of the "Huanglianjiedu decoction". Zorbax Extend C18 (150 mm x 4. 6 mm ID, 5 microm) column was used; the mobile phase was composed of acetonitrile (A) and water (B, with 0.5% acetic acid) with gradient elution; the flow rate was 1.0 mL x min(-1) and the column temperature was setup at 25 degrees C. The detection wavelength was 254 nm. The chromatogram of Huanglianjiedu decoction showed 21 main peaks. Peaks 1, 2, 5 and 18 were from Gardenia jasminoides Ellis, Peaks 8, 13, 14, 15, 16, 17, 19 and 21 from Scutellaria baicalensis Georgi. While 10 from Coptis chinensis Franch and 20 from Phellodendron amurense Rupr., Peaks 3, 4, 6, 9, 11 and 12 came from them together. Peak 7 presented in the chromatograms of the herbs except Gardenia jasminoides Ellis. By comparison of the retention time, the on-line UV spectra and MS spectra, 11 peaks were identified as 5 (geniposide), 9 (jatrorrhizine), 10 (coptisine), 11 (palmatine), 12 (berberine), 13 (baicalin), 15 (Oroxin A), 17 (wogonoside), 19 (baicalein), 20 (obaculactone), 21 (wogonin), then eight of them were quantified by HPLC-UV.
CONCLUSIONS:
The method could represent the characteristics of Huanglianjiedu decoction, and it could be used to evaluate the quality and quantity of Huanglianjiedu decoction. It distinguished between Coptis chinensis Franch and Phellodendron amurense Rupr. by HPLC for the first time.

Oroxin A Dilution Calculator

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Preparing Stock Solutions of Oroxin A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3128 mL 11.5639 mL 23.1278 mL 46.2556 mL 57.8195 mL
5 mM 0.4626 mL 2.3128 mL 4.6256 mL 9.2511 mL 11.5639 mL
10 mM 0.2313 mL 1.1564 mL 2.3128 mL 4.6256 mL 5.782 mL
50 mM 0.0463 mL 0.2313 mL 0.4626 mL 0.9251 mL 1.1564 mL
100 mM 0.0231 mL 0.1156 mL 0.2313 mL 0.4626 mL 0.5782 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 Oroxin A

Oroxin A inhibits breast cancer cell growth by inducing robust endoplasmic reticulum stress and senescence.[Pubmed:26599214]

Anticancer Drugs. 2016 Mar;27(3):204-15.

Breast cancer is a major cause of cancer death among women. Although various anticancer drugs have been used in clinics, drugs that are effective against advanced and metastatic breast cancer are still lacking and in great demand. In this study, we found that Oroxin A, an active component isolated from the herb Oroxylum indicum (L.) Kurz, effectively inhibited the growth of human breast cancer cells MDA-MB-231 and MCF7 by inducing endoplasmic reticulum (ER) stress-mediated senescence. Oroxin A caused breast cancer cell cycle arrest at the G2/M stage, and reorganization of microtubules and actin cytoskeleton accompanied by a decrease in cellular mitosis. ER-specific probe ER-Tracker Red and confocal microscope imaging showed that ER-Tracker Red-positive cells increased in an Oroxin A dosage-dependent manner. In addition, Oroxin A increased cell population with high beta-Gal activity and SAHF-positive staining; these data suggest that Oroxin A induces breast cancer cell ER stress and senescence. Mechanistic studies showed that Oroxin A led to a significant increase in intracellular reactive oxygen species levels, promoted expression of ER stress markers ATF4 and GRP78, and increased the phosphorylation of a key stress-response signaling protein p38, resulting in an ER stress-mediated senescence. Taken together, our data indicate that Oroxin A exerts its antibreast cancer effects by inducing ER stress-mediated senescence, activating the key stress p38 signaling pathway, and increasing key ER stress genes ATF4 and GRP78 expression levels.

Discovery of xanthine oxidase inhibitors from a complex mixture using an online, restricted-access material coupled with column-switching liquid chromatography with a diode-array detection system.[Pubmed:24510210]

Anal Bioanal Chem. 2014 Mar;406(7):1975-84.

To find potential lead compounds for antigout drug discovery, an automated online, restricted-access material coupled with column-switching liquid chromatography with a diode-array detection (RAM-LC-DAD) system was developed for screening of xanthine oxidase (XO) inhibitors and their affinity rankings in complex mixtures. The system was first evaluated by analyzing a mixture of six compounds with known inhibition of XO. Nonspecific binding to the denatured XO was investigated and used as the control for screening. Subsequently, the newly developed system was applied to screening of a natural product, Oroxylum indicum extract, and four compounds which could specifically interact with XO were found and identified as oroxin B, Oroxin A, baicalin, and baicalein. The results were verified by a competitive binding test using the known competitive inhibitor allopurinol and were further validated by an inhibition assay in vitro. The online RAM-LC-DAD system developed was shown to be a simple and effective strategy for the rapid screening of bioactive compounds from a complex mixture.

[Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS].[Pubmed:16856488]

Yao Xue Xue Bao. 2006 Apr;41(4):380-4.

AIM: To establish a comprehensive HPLC analytical method of Huanglianjiedu decoction. METHODS: This study was performed by HPLC-UV/MS to identify the chemical constituents of the whole and individual herbs of the "Huanglianjiedu decoction". Zorbax Extend C18 (150 mm x 4. 6 mm ID, 5 microm) column was used; the mobile phase was composed of acetonitrile (A) and water (B, with 0.5% acetic acid) with gradient elution; the flow rate was 1.0 mL x min(-1) and the column temperature was setup at 25 degrees C. The detection wavelength was 254 nm. RESULTS: The chromatogram of Huanglianjiedu decoction showed 21 main peaks. Peaks 1, 2, 5 and 18 were from Gardenia jasminoides Ellis, Peaks 8, 13, 14, 15, 16, 17, 19 and 21 from Scutellaria baicalensis Georgi. While 10 from Coptis chinensis Franch and 20 from Phellodendron amurense Rupr., Peaks 3, 4, 6, 9, 11 and 12 came from them together. Peak 7 presented in the chromatograms of the herbs except Gardenia jasminoides Ellis. By comparison of the retention time, the on-line UV spectra and MS spectra, 11 peaks were identified as 5 (geniposide), 9 (jatrorrhizine), 10 (coptisine), 11 (palmatine), 12 (berberine), 13 (baicalin), 15 (Oroxin A), 17 (wogonoside), 19 (baicalein), 20 (obaculactone), 21 (wogonin), then eight of them were quantified by HPLC-UV. CONCLUSION: The method could represent the characteristics of Huanglianjiedu decoction, and it could be used to evaluate the quality and quantity of Huanglianjiedu decoction. It distinguished between Coptis chinensis Franch and Phellodendron amurense Rupr. by HPLC for the first time.

Description

Oroxin A is the major component of an ethanol-water Oroxylum indicum (L.) Kurz (Bignoniaceae) seed extract (OISE), activates peroxisome proliferator-activated receptor γ (PPARγ) by docking into the PPARγ protein ligand-binding domain. Oroxin A exhibits an inhibitory activity against α-glucosidase and an antioxidant capacity. Oroxin A exerts anti-breast cancer effects by inducing ER stress-mediated senescence.

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