Oroxin BCAS# 114482-86-9 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 114482-86-9 | SDF | Download SDF |
| PubChem ID | 10077207 | Appearance | Yellowish powder |
| Formula | C27H30O15 | M.Wt | 594.52 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | Baicalein 7-gentiobioside; Oroxin B; 5,6,7-Trihydroxyflavone 7-diglucoside | ||
| Solubility | Soluble in methanol and water | ||
| Chemical Name | 5,6-dihydroxy-2-phenyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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)COC5C(C(C(C(O5)CO)O)O)O)O)O)O)O)O | ||
| Standard InChIKey | HAYLVXFWJCKKDW-IJTBWITGSA-N | ||
| Standard InChI | InChI=1S/C27H30O15/c28-8-15-19(31)22(34)24(36)26(41-15)38-9-16-20(32)23(35)25(37)27(42-16)40-14-7-13-17(21(33)18(14)30)11(29)6-12(39-13)10-4-2-1-3-5-10/h1-7,15-16,19-20,22-28,30-37H,8-9H2/t15-,16-,19-,20-,22+,23+,24-,25-,26-,27-/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. |
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| 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. |
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| 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. | ||
| Description | Oroxin B can selectively induce tumor-suppressive ER stress and concurrently inhibit tumor-adaptive ER stress in B-lymphoma cells for effective anti-lymphoma therapy. |
| Targets | p38MAPK |
| In vitro | Molecular modeling reveals the novel inhibition mechanism and binding mode of three natural compounds to staphylococcal α-hemolysin.[Pubmed: 24312202 ]PLoS One. 2013 Nov 27;8(11):e80197. |
| In vivo | Oroxin B selectively induces tumor-suppressive ER stress and concurrently inhibits tumor-adaptive ER stress in B-lymphoma cells for effective anti-lymphoma therapy.[Pubmed: 26253462 ]Toxicol Appl Pharmacol. 2015 Oct 15;288(2):269-79.Cancer cells have both tumor-adaptive and -suppressive endoplasmic reticulum (ER) stress machineries that determine cell fate. In malignant tumors including lymphoma, constant activation of tumor-adaptive ER stress and concurrent reduction of tumor-suppressive ER stress favors cancer cell proliferation and tumor growth.
Current ER stress-based anti-tumor drugs typically activate both tumor-adaptive and -suppressive ER stresses, resulting in low anti-cancer efficacy; hence, selective induction of tumor-suppressive ER stress and inhibition of tumor-adaptive ER stress are new strategies for novel anti-cancer drug discovery. Thus far, specific tumor-suppressive ER stress therapeutics have remained absent in clinical settings.
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Oroxin B Dilution Calculator
Oroxin B Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.682 mL | 8.4101 mL | 16.8203 mL | 33.6406 mL | 42.0507 mL |
| 5 mM | 0.3364 mL | 1.682 mL | 3.3641 mL | 6.7281 mL | 8.4101 mL |
| 10 mM | 0.1682 mL | 0.841 mL | 1.682 mL | 3.3641 mL | 4.2051 mL |
| 50 mM | 0.0336 mL | 0.1682 mL | 0.3364 mL | 0.6728 mL | 0.841 mL |
| 100 mM | 0.0168 mL | 0.0841 mL | 0.1682 mL | 0.3364 mL | 0.4205 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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[Chemical constitunents of seeds of Oroxylum indicum].[Pubmed:23672042]
Zhongguo Zhong Yao Za Zhi. 2013 Jan;38(2):204-7.
OBJECTIVE: To study the chemical constituents in the seeds of Oroxylum indicum. METHOD: Twenty compounds were isolated and purified by silica gel, and Sephadex LH-20 column chromatography, and their structures were determined by spectroscopic analysis including NMR and MS. RESULT: Twenty compounds were isolated and identified as oroxin A (1), Oroxin B (2), chrysin (3), baicalein (4), quercetin (5), apigenin (6), kaempferol (7), quercetin-3-O-ara-binopyranoside (8), lupeol C9), lup-20 (29)-ene-2alpha,3beta-diol (10), pinosylvin (11), dihydropinosylvin (12), cholest-5-ene-3, 7-diol (13), rengyol (14), isorengyol (15), zarzissine (16), (E) -pinosylvin-3-O-beta-D-glucopyranoside (17), adenosine (18), sitosterol (19) and daucosterol (20). CONCLUSION: Compounds 11-13 and 15-18 were obtained from the genus Oroxylum for the first time, and except compound 18, the remaining 6 compounds were obtained from the family Bignoniaceae for the first time.
Oroxin B selectively induces tumor-suppressive ER stress and concurrently inhibits tumor-adaptive ER stress in B-lymphoma cells for effective anti-lymphoma therapy.[Pubmed:26253462]
Toxicol Appl Pharmacol. 2015 Oct 15;288(2):269-79.
Cancer cells have both tumor-adaptive and -suppressive endoplasmic reticulum (ER) stress machineries that determine cell fate. In malignant tumors including lymphoma, constant activation of tumor-adaptive ER stress and concurrent reduction of tumor-suppressive ER stress favors cancer cell proliferation and tumor growth. Current ER stress-based anti-tumor drugs typically activate both tumor-adaptive and -suppressive ER stresses, resulting in low anti-cancer efficacy; hence, selective induction of tumor-suppressive ER stress and inhibition of tumor-adaptive ER stress are new strategies for novel anti-cancer drug discovery. Thus far, specific tumor-suppressive ER stress therapeutics have remained absent in clinical settings. In this study, we explored unique tumor-suppressive ER stress agents from the traditional Chinese medicinal herb Oroxylum indicum, and found that a small molecule Oroxin B selectively induced tumor-suppressive ER stress in malignant lymphoma cells, but not in normal cells, effectively inhibited lymphoma growth in vivo, and significantly prolonged overall survival of lymphoma-xenografted mice without obvious toxicity. Mechanistic studies have revealed that the expression of key tumor-adaptive ER-stress gene GRP78 was notably suppressed by Oroxin B via down-regulation of up-stream key signaling protein ATF6, while tumor-suppressive ER stress master gene DDIT3 was strikingly activated through activating the MKK3-p38 signaling pathway, correcting the imbalance between tumor-suppressive DDIT3 and tumor-adaptive GRP78 in lymphoma. Together, selective induction of unique tumor-suppressive ER stress and concurrent inhibition of tumor-adaptive ER stress in malignant lymphoma are new and feasible approaches for novel anti-lymphoma drug discovery and anti-lymphoma therapy.
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.
Molecular modeling reveals the novel inhibition mechanism and binding mode of three natural compounds to staphylococcal alpha-hemolysin.[Pubmed:24312202]
PLoS One. 2013 Nov 27;8(11):e80197.
alpha-Hemolysin (alpha-HL) is a self-assembling, channel-forming toxin that is produced as a soluble monomer by Staphylococcus aureus strains. Until now, alpha-HL has been a significant virulence target for the treatment of S. aureus infection. In our previous report, we demonstrated that some natural compounds could bind to alpha-HL. Due to the binding of those compounds, the conformational transition of alpha-HL from the monomer to the oligomer was blocked, which resulted in inhibition of the hemolytic activity of alpha-HL. However, these results have not indicated how the binding of the alpha-HL inhibitors influence the conformational transition of the whole protein during the oligomerization process. In this study, we found that three natural compounds, Oroxylin A 7-O-glucuronide (OLG), Oroxin A (ORA), and Oroxin B (ORB), when inhibiting the hemolytic activity of alpha-HL, could bind to the "stem" region of alpha-HL. This was completed using conventional Molecular Dynamics (MD) simulations. By interacting with the novel binding sites of alpha-HL, the ligands could form strong interactions with both sides of the binding cavity. The results of the principal component analysis (PCA) indicated that because of the inhibitors that bind to the "stem" region of alpha-HL, the conformational transition of alpha-HL from the monomer to the oligomer was restricted. This caused the inhibition of the hemolytic activity of alpha-HL. This novel inhibition mechanism has been confirmed by both the steered MD simulations and the experimental data obtained from a deoxycholate-induced oligomerization assay. This study can facilitate the design of new antibacterial drugs against S. aureus.
