TrifolirhizinCAS# 6807-83-6 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 6807-83-6 | SDF | Download SDF |
| PubChem ID | 442827 | Appearance | White crystalline |
| Formula | C22H22O10 | M.Wt | 446.4 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | (-)-Maackiain 3-O-glucoside; Sophojaponicin B1 | ||
| Solubility | Soluble in acetone; sparingly soluble in methan | ||
| SMILES | C1C2C(C3=C(O1)C=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC5=CC6=C(C=C25)OCO6 | ||
| Standard InChIKey | VGSYCWGXBYZLLE-QEEQPWONSA-N | ||
| Standard InChI | InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/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. | ||
| Description | Trifolirhizin possesses potential anti-inflammatory and anti-cancer activities, it inhibits acetylcholine mediated airway smooth muscle (ASM) contraction or directly relaxes pre-contracted ASM independent of β 2 -adrenoceptors. Trifolirhizin may be a a candidate as skin-whitening agents, it exerts varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis. |
| Targets | Adrenergic Receptor | COX | TNF-α | IL Receptor |
| In vitro | Anti-Inflammatory and antiproliferative activities of trifolirhizin, a flavonoid from Sophora flavescens roots.[Pubmed: 19402641 ]J Agric Food Chem. 2009 Jun 10;57(11):4580-5.Trifolirhizin, a pterocarpan flavonoid, was isolated from the roots of Sophora flavescens, and its chemical structure was confirmed by (1)H and (13)C NMR and MS spectra.
Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesis.[Pubmed: 18175961]Biol Pharm Bull. 2008 Jan;31(1):154-8.Previously, it was reported that some prenylated flavonoids contained in the dichloromethane fraction of the ethanolic extract of Sophora flavescens, such as kuraridin, sophoraflavanone G, kurarinone, and kushenol F, are tyrosinase inhibitors; however, based on the level of these inhibitors in the extract, its inhibitory effect on tyrosinase activity was higher than expected.
This has led us to further investigate other possible constituents that may contribute to the extract's strong inhibitory activity.
|
| Cell Research | Induction of apoptosis by maackiain and trifolirhizin (maackiain glycoside) isolated from sanzukon (Sophora Subprostrate Chen et T. Chen) in human promyelotic leukemia HL-60 cells.[Pubmed: 15547735 ]Oncol Rep. 2004 Dec;12(6):1183-8.We have investigated the effects of maackiain and Trifolirhizin (maackiain glycoside) isolated from sanzukon (Sophora Subprostrate Chen et T. Chen) on DNA of human promyelotic HL-60 leukemia cells.
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| Animal Research | The Sophora flavescens flavonoid compound trifolirhizin inhibits acetylcholine induced airway smooth muscle contraction.[Pubmed: 23993294]Phytochemistry. 2013 Nov;95:259-67.Asthma is a serious health problem worldwide, particularly in industrialized countries. Despite a better understanding of the pathophysiology of asthma, there are still considerable gaps in knowledge as well as a need for classes of drugs.
ASHMI™ (Anti-asthma Herbal Medicine Intervention) is an aqueous extract of Ganoderma lucidum (Fr.) P. Karst (Ling Zhi), Sophora flavescens Aiton (Ku Shen) and Glycyrrhiza uralensis Fisch. ex DC (Gan Cao).
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Trifolirhizin Dilution Calculator
Trifolirhizin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2401 mL | 11.2007 mL | 22.4014 mL | 44.8029 mL | 56.0036 mL |
| 5 mM | 0.448 mL | 2.2401 mL | 4.4803 mL | 8.9606 mL | 11.2007 mL |
| 10 mM | 0.224 mL | 1.1201 mL | 2.2401 mL | 4.4803 mL | 5.6004 mL |
| 50 mM | 0.0448 mL | 0.224 mL | 0.448 mL | 0.8961 mL | 1.1201 mL |
| 100 mM | 0.0224 mL | 0.112 mL | 0.224 mL | 0.448 mL | 0.56 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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Anti-Inflammatory and antiproliferative activities of trifolirhizin, a flavonoid from Sophora flavescens roots.[Pubmed:19402641]
J Agric Food Chem. 2009 Jun 10;57(11):4580-5.
Trifolirhizin, a pterocarpan flavonoid, was isolated from the roots of Sophora flavescens, and its chemical structure was confirmed by (1)H and (13)C NMR and MS spectra. Its anti-inflammatory activity was examined in lipopolysaccharide (LPS)-stimulated mouse J774A.1 macrophages. Trifolirhizin not only dose-dependently inhibited LPS-induced expression of pro-inflammatory cytokines including tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6) but also inhibited lipopolysaccharide (LPS)-induced expression of cyclooxygenase-2 (COX-2). In addition, Trifolirhizin showed in vitro inhibitory effects on the growth of human A2780 ovarian and H23 lung cancer cells. These results suggest that Trifolirhizin possesses potential anti-inflammatory and anticancer activities.
Induction of apoptosis by maackiain and trifolirhizin (maackiain glycoside) isolated from sanzukon (Sophora Subprostrate Chen et T. Chen) in human promyelotic leukemia HL-60 cells.[Pubmed:15547735]
Oncol Rep. 2004 Dec;12(6):1183-8.
We have investigated the effects of maackiain and Trifolirhizin (maackiain glycoside) isolated from sanzukon (Sophora Subprostrate Chen et T. Chen) on DNA of human promyelotic HL-60 leukemia cells. It was found that extent of induction of apoptosis by maackiain was larger than that by Trifolirhizin in human leukemia HL-60 cells. Morphological changes showing apoptotic bodies were observed in the HL-60 cells treated with maackiain and Trifolirhizin. The fragmentations of DNA by maackiain and Trifolirhizin to oligonucleosomal-sized fragments that is a characteristic of apoptosis was observed to be concentration- and time-dependent in the HL-60 cells. The data of the present study show that the suppressions by maackiain and trifolrhizin of growth of the HL-60 cells result from the induction of apoptosis by these compounds, and that the extent of growth suppression and induction of apoptosis by maackiain was greater than that by the glycoside (Trifolirhizin).
Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesis.[Pubmed:18175961]
Biol Pharm Bull. 2008 Jan;31(1):154-8.
Previously, it was reported that some prenylated flavonoids contained in the dichloromethane fraction of the ethanolic extract of Sophora flavescens, such as kuraridin, sophoraflavanone G, kurarinone, and kushenol F, are tyrosinase inhibitors; however, based on the level of these inhibitors in the extract, its inhibitory effect on tyrosinase activity was higher than expected. This has led us to further investigate other possible constituents that may contribute to the extract's strong inhibitory activity. The results of this study indicate that kurarinol (1), kuraridinol (2), and Trifolirhizin (3), from the ethyl acetate fraction of Sophora extract, can inhibit tyrosinase activity. Compared with kojic acid (16.22+/-1.71 microM), compounds 1-3 possessed potent tyrosinase inhibitory activity with IC(50) values of 8.60+/-0.51, 0.88+/-0.06, and 506.77+/-4.94 microM, respectively. These three compounds were further tested for their inhibitory effects on melanogenesis. In cultured B16 melanoma cells, 1-3 markedly inhibited (>50%) melanin synthesis at 50 microM. This is the first study indicating that 1-3 exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, and therefore, are candidates as skin-whitening agents.
The Sophora flavescens flavonoid compound trifolirhizin inhibits acetylcholine induced airway smooth muscle contraction.[Pubmed:23993294]
Phytochemistry. 2013 Nov;95:259-267.
Asthma is a serious health problem worldwide, particularly in industrialized countries. Despite a better understanding of the pathophysiology of asthma, there are still considerable gaps in knowledge as well as a need for classes of drugs. ASHMI (Anti-asthma Herbal Medicine Intervention) is an aqueous extract of Ganoderma lucidum (Fr.) P. Karst (Ling Zhi), Sophora flavescens Aiton (Ku Shen) and Glycyrrhiza uralensis Fisch. ex DC (Gan Cao). It prevents allergic asthma airway hyper-reactivity in mice and inhibits acetylcholine (ACh) induced airway smooth muscle (ASM) contraction in tracheal rings from allergic asthmatic mice. The purpose of this research was to identify individual herb(s) and their active compound(s) that inhibit ASM contraction. It was found that S. flavescens, but not G. lucidum or G. uralensis aqueous extracts, inhibited ASM contraction in tracheal rings from asthmatic mice. Bioassay-guided isolation and identification of flavonoid fractions/compound(s) via methylene chloride extraction, preparative HPLC fractionation, and LC-MS and NMR spectroscopic analyses showed that Trifolirhizin is an active constituent that inhibits acetylcholine mediated ASM contraction or directly relaxes pre-contracted ASM independent of beta2-adrenoceptors.
