Ephedrannin ACAS# 82001-39-6 |
Quality Control & MSDS
3D structure
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Number of papers citing our products
| Cas No. | 82001-39-6 | SDF | Download SDF |
| PubChem ID | 21676348 | Appearance | Powder |
| Formula | C30H20O11 | M.Wt | 556.5 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),5,9,15,17,19-heptaen-7-one | ||
| SMILES | C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C4=C(C=C3O)OC5(C(C4C6=C(C=C(C=C6O5)O)O)O)C7=CC=C(C=C7)O)O)O | ||
| Standard InChIKey | GPBSBBVDERLESN-QZFRTWIZSA-N | ||
| Standard InChI | InChI=1S/C30H20O11/c31-14-5-1-12(2-6-14)27-26(37)25(36)22-18(35)11-20-23(28(22)39-27)24-21-17(34)9-16(33)10-19(21)40-30(41-20,29(24)38)13-3-7-15(32)8-4-13/h1-11,24,29,31-35,37-38H/t24-,29-,30+/m0/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. | ||
Ephedrannin A Dilution Calculator
Ephedrannin A Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.7969 mL | 8.9847 mL | 17.9695 mL | 35.9389 mL | 44.9236 mL |
| 5 mM | 0.3594 mL | 1.7969 mL | 3.5939 mL | 7.1878 mL | 8.9847 mL |
| 10 mM | 0.1797 mL | 0.8985 mL | 1.7969 mL | 3.5939 mL | 4.4924 mL |
| 50 mM | 0.0359 mL | 0.1797 mL | 0.3594 mL | 0.7188 mL | 0.8985 mL |
| 100 mM | 0.018 mL | 0.0898 mL | 0.1797 mL | 0.3594 mL | 0.4492 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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Inhibitory effect of ephedrannins A and B from roots of Ephedra sinica STAPF on melanogenesis.[Pubmed:25857772]
Biochim Biophys Acta. 2015 Jul;1850(7):1389-96.
BACKGROUND: Melanogenesis, a process producing the pigment melanin in human skin, eyes and hair, is a major physiological response against various environmental stresses, in particular exposure to ultraviolet radiation, and its pathway is regulated by a key enzyme, tyrosinase. In this study, we evaluated the effects of ephedrannins A and B, which are polyphenols from the roots of Ephedra sinica, commonly used in herbalism in oriental countries, on mushroom tyrosinase and melanogenesis in B16F10 melanoma cells. METHODS: Their effects on mushroom tyrosinase were determined via kinetic studies using a spectrophotometric analysis and those on melanin and tyrosinase production in melanoma cells treated with alpha-MSH (melanin stimulating hormone) were examined using PCR and ELISA. RESULTS: Both ephedrannins A and B exhibited concentration-dependent inhibitory effects on L-tyrosine oxidation by mushroom tyrosinase, and the inhibition mechanism was competitive and reversible with L-tyrosine as the substrate. In addition, melanin production in melanoma cells was also suppressed in a concentration-dependent manner by ephedrannins A and B without significant effects on cell proliferation at the concentrations tested. Both compounds showed inhibitory effects on melanin production by suppressing the transcription of tyrosinase in the cells. CONCLUSION: Both compounds exhibited significant inhibitory effects, but the inhibition by ephedrannin B was much more effective than that by Ephedrannin A. Both ephedrannins A and B may be good candidates for a whitening agent for skin. GENERAL SIGNIFICANCE: This is the first report that describes effective inhibition of melanin production by ephedrannins A and B isolated from Ephedra roots.
Ephedrannin A and B from roots of Ephedra sinica inhibit lipopolysaccharide-induced inflammatory mediators by suppressing nuclear factor-kappaB activation in RAW 264.7 macrophages.[Pubmed:20939997]
Int Immunopharmacol. 2010 Dec;10(12):1616-25.
Ephedra sinica is a traditional Chinese medicinal herb and has pharmacological functions including anti-inflammatory effects. However, the active ingredients from Ephedra roots have not been characterized. Here, two active constituents were isolated and their structures and mechanisms of action were defined. Active constituents from Ephedra roots were isolated by continuous solvent-extractions and column chromatography. Their structures were determined by use of multiple types of spectrometry. The mechanisms of action were examined using lipopolysaccharide (LPS)-stimulated RAW 264.7 cells through PCR, ELISA, electrophoretic mobility shift assays, and immunocytochemistry. Two active constituents, Ephedrannin A and B, belonging to the A-type proanthocyanidin family were identified. Both Ephedrannin A and B effectively suppressed the transcription of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1beta (IL-1beta). These compounds exerted their anti-inflammatory actions on LPS-stimulated macrophages by suppressing the translocation of nuclear factor-kappa B (NF-kappaB) and the phosphorylation of p38 mitogen-activated protein (MAP) kinase. Ephedrannin A and B both exhibited strong anti-inflammatory effects, however, the optimal dose of ephedrannin B was 10 times lower than that of Ephedrannin A. This is the first report describing effective anti-inflammatory activity for Ephedrannin A and B isolated from Ephedra roots. Ephedrannin B may be a good candidate for delaying the progression of human inflammatory diseases and warrants further studies.
Dimeric proanthocyanidins from the roots of Ephedra sinica.[Pubmed:18975262]
Planta Med. 2008 Dec;74(15):1823-5.
Two new dimeric proanthocyanidins, ephedrannin B ( 2) and mahuannin E ( 4), along with two known congeners, Ephedrannin A ( 1) and mahuannin D ( 3), were isolated from the roots of Ephedra sinica Stapf. Based on NMR, MS, and CD analysis, the structures of the new compounds were deduced to be 5,7,4'-trihydroxyflavan-[4(alpha)-->8,2(alpha)-->O-->7]-kaempferol ( 2) and 5,7,4'-trihydroxyflavan-[4(beta)-->8,2(beta)-->O-->7]- EPI-afzelechin ( 4). The compounds 1 - 4 were evaluated for cytotoxicity against three tumor cell lines (SGC-7901, HepG2, and HeLa), and 2 was found to be significantly active.
