(+)-LyoniresinolCAS# 14464-90-5 |
- (-)-Lyoniresinol
Catalog No.:BCN3488
CAS No.:31768-94-2
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 14464-90-5 | SDF | Download SDF |
| PubChem ID | 11711453 | Appearance | Powder |
| Formula | C22H28O8 | M.Wt | 420.5 |
| Type of Compound | Lignans | Storage | Desiccate at -20°C |
| Synonyms | lyoniresinol | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (6R,7R,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol | ||
| SMILES | COC1=CC(=CC(=C1O)OC)C2C(C(CC3=CC(=C(C(=C23)OC)O)OC)CO)CO | ||
| Standard InChIKey | ZDVZKBOFCHOPLM-SUNYJGFJSA-N | ||
| Standard InChI | InChI=1S/C22H28O8/c1-27-15-7-12(8-16(28-2)20(15)25)18-14(10-24)13(9-23)5-11-6-17(29-3)21(26)22(30-4)19(11)18/h6-8,13-14,18,23-26H,5,9-10H2,1-4H3/t13-,14-,18+/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 | 1. Lyoniresinol shows robust anti-melanogenic activity, decreases tyrosinase activity and melanin biosynthesis in B16F10 cells by activating ERK signaling, which downregulated MITF, tyrosinase, but not TRP-1 and TRP-2 protein expression. 2. Lyoniresinol has antioxidant effect. |
| Targets | ERK |
(+)-Lyoniresinol Dilution Calculator
(+)-Lyoniresinol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3781 mL | 11.8906 mL | 23.7812 mL | 47.5624 mL | 59.453 mL |
| 5 mM | 0.4756 mL | 2.3781 mL | 4.7562 mL | 9.5125 mL | 11.8906 mL |
| 10 mM | 0.2378 mL | 1.1891 mL | 2.3781 mL | 4.7562 mL | 5.9453 mL |
| 50 mM | 0.0476 mL | 0.2378 mL | 0.4756 mL | 0.9512 mL | 1.1891 mL |
| 100 mM | 0.0238 mL | 0.1189 mL | 0.2378 mL | 0.4756 mL | 0.5945 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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Antimicrobial property of (+)-lyoniresinol-3alpha-O-beta-D-glucopyranoside isolated from the root bark of Lycium chinense Miller against human pathogenic microorganisms.[Pubmed:16212233]
Arch Pharm Res. 2005 Sep;28(9):1031-6.
(+)-Lyoniresinol-3alpha-O-beta-D-glucopyranoside (1) was isolated from an ethyl acetate extract of the root bark from Lycium chinense Miller, and its structure was determined using 1D and 2D NMR spectroscopy including DEPT, HMQC, and HMBC. (+)-Lyoniresinol-3alpha-O-beta-D-glucopyranoside exhibited potent antimicrobial activity against antibiotic-resistant bacterial strains, methicillin-resistant Staphylococcus aureus (MRSA) isolated from patients, and human pathogenic fungi without having any hemolytic effect on human erythrocytes. In particular, compound 1 induced the accumulation of intracellular trehalose on C. albicans as stress response to the drug, and disrupted the dimorphic transition that forms pseudo-hyphae caused by the pathogenesis. This indicates that (+)-Lyoniresinol-3alpha-O-beta-D-glucopyranoside has excellent potential as a lead compound for the development of antibiotic agents.
A short asymmetric synthesis of (+)-lyoniresinol dimethyl ether.[Pubmed:15176840]
J Org Chem. 2004 Jun 11;69(12):4140-4.
A short, efficient synthesis of the lignan (+)-Lyoniresinol dimethyl ether is described. The synthesis is achieved by asymmetric photocyclization of an achiral dibenzylidenesuccinate to a chiral aryldihydronaphthalene. (-)-Ephedrine is used as a chiral auxiliary to bias the atropisomeric equilibrium in the dibenzylidenesuccinate prior to the photochemical reaction. The synthesis of the title compound was accomplished in five steps, and the final product was recrystallized to constant melting point and rotation.
Lyoniresinol inhibits melanogenic activity through the induction of microphthalmia-associated transcription factor and extracellular receptor kinase activation.[Pubmed:23099844]
Mol Cell Biochem. 2013 Jan;373(1-2):211-6.
Lyoniresinol was one of the eight lignans purified from methanol extract of Vitex negundo and was shown to have robust tyrosinase inhibitory capacity. However, the mechanism of its action is not known. Hence, the goal of the current study was to study the effects of Lyoniresinol on cytotoxicity and melanin content in murine B16F10 melanoma cells and to delineate the underlying mechanism of tyrosinase inhibition. Lyoniresinol was purified from methanol extract of Vitex negundo root and when tested in B16F10, cells showed robust anti-melanogenic activity. It caused the downregulation of microphthalmia-associated transcription factor (MITF) and tyrosinase steady state protein expression levels. Flow cytometry analysis of Lyoniresinol-treated cells showed that the latter activates extracellular receptor kinase (ERK) phosphorylation, which causes MITF protein degradation and suppression of tyrosinase activity. Lyoniresinol decreased tyrosinase activity and melanin biosynthesis in B16F10 cells by activating ERK signaling, which downregulated MITF, tyrosinase, but not TRP-1 and TRP-2 protein expression. Contingent to more vigorous in vitro and in vivo experiments, Lyoniresinol can perhaps be incorporated into clinical dermatologic use as a skin lightening agent.
