Lappaol FCAS# 69394-17-8 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 69394-17-8 | SDF | Download SDF |
| PubChem ID | 73425459 | Appearance | Powder |
| Formula | C40H42O12 | M.Wt | 714.8 |
| Type of Compound | Lignans | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (3R,4R)-3,4-bis[[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]methyl]oxolan-2-one | ||
| SMILES | COC1=C(C=CC(=C1)C2C(C3=CC(=CC(=C3O2)OC)CC4COC(=O)C4CC5=CC(=C6C(=C5)C(C(O6)C7=CC(=C(C=C7)O)OC)CO)OC)CO)O | ||
| Standard InChIKey | YXNKOCZXAVTXTG-NYGVLQSXSA-N | ||
| Standard InChI | InChI=1S/C40H42O12/c1-46-32-15-22(5-7-30(32)43)36-28(17-41)26-11-20(13-34(48-3)38(26)51-36)9-24-19-50-40(45)25(24)10-21-12-27-29(18-42)37(52-39(27)35(14-21)49-4)23-6-8-31(44)33(16-23)47-2/h5-8,11-16,24-25,28-29,36-37,41-44H,9-10,17-19H2,1-4H3/t24-,25+,28-,29-,36+,37+/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. Lappaol F has antioxidant and antiaging properties, it may promote the C. elegans longevity and stress resistance through a JNK-1-DAF-16 cascade. 2. Lappaol F has potential chemosensitizing activity, it may be candidates for developing novel adjuvant anticancer agents. 3. Lappaol F exhibits antitumor activity in vitro and in vivo and has strong potential to be developed as an anticancer therapeutic. 4. Lappaol F strongly inhibited NO production in the LPS-stimulated RAW264.7 cells with the IC(50) value of 9.5 microM. |
| Targets | JNK | P-gp | p21 | CDK | NO |
Lappaol F Dilution Calculator
Lappaol F Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.399 mL | 6.995 mL | 13.9899 mL | 27.9799 mL | 34.9748 mL |
| 5 mM | 0.2798 mL | 1.399 mL | 2.798 mL | 5.596 mL | 6.995 mL |
| 10 mM | 0.1399 mL | 0.6995 mL | 1.399 mL | 2.798 mL | 3.4975 mL |
| 50 mM | 0.028 mL | 0.1399 mL | 0.2798 mL | 0.5596 mL | 0.6995 mL |
| 100 mM | 0.014 mL | 0.0699 mL | 0.1399 mL | 0.2798 mL | 0.3497 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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Natural lignans from Arctium lappa modulate P-glycoprotein efflux function in multidrug resistant cancer cells.[Pubmed:25765837]
Phytomedicine. 2015 Feb 15;22(2):301-7.
Arctium lappa is a well-known traditional medicinal plant in China (TCM) and Europe that has been used for thousands of years to treat arthritis, baldness or cancer. The plant produces lignans as secondary metabolites which have a wide range of bioactivities. Yet, their ability to reverse multidrug resistance (MDR) in cancer cells has not been explored. In this study, we isolated six lignans from A. lappa seeds, namely arctigenin, matairesinol, arctiin, (iso)lappaol A, lappaol C, and Lappaol F. The MDR reversal potential of the isolated lignans and the underlying mechanism of action were studied using two MDR cancer cell lines, CaCo2 and CEM/ADR 5000 which overexpress P-gp and other ABC transporters. In two-drug combinations of lignans with the cytotoxic doxorubicin, all lignans exhibited synergistic effects in CaCo2 cells and matairesinol, arctiin, lappaol C and Lappaol F display synergistic activity in CEM/ADR 5000 cells. Additionally, in three-drug combinations of lignans with the saponin digitonin and doxorubicin MDR reversal activity was even stronger enhanced. The lignans can increase the retention of the P-gp substrate rhodamine 123 in CEM/ADR 5000 cells, indicating that lignans can inhibit the activity of P-gp. Our study provides a first insight into the potential chemosensitizing activity of a series of natural lignans, which might be candidates for developing novel adjuvant anticancer agents.
Lignans from Arctium lappa and their inhibition of LPS-induced nitric oxide production.[Pubmed:17202721]
Chem Pharm Bull (Tokyo). 2007 Jan;55(1):150-2.
A new butyrolactone sesquilignan, isolappaol C (1), together with four known lignans, lappaol C (2), lappaol D (3), Lappaol F (4), and diarctigenin (5), were isolated from the methanolic extract of the seeds from the Arctium lappa plant. The structure of isolappaol C (1) was determined by spectral analysis including 1D- and 2D-NMR. All the isolates were evaluated for their inhibitory effects on the LPS-induced nitric oxide production using murine macrophage RAW264.7 cells. Lappaol F (4) and diarctigenin (5) strongly inhibited NO production in the LPS-stimulated RAW264.7 cells with IC(50) values of 9.5 and 9.6 microM, respectively.
Lappaol F, a novel anticancer agent isolated from plant arctium Lappa L.[Pubmed:24222662]
Mol Cancer Ther. 2014 Jan;13(1):49-59.
In an effort to search for new cancer-fighting therapeutics, we identified a novel anticancer constituent, Lappaol F, from plant Arctium Lappa L. Lappaol F suppressed cancer cell growth in a time- and dose-dependent manner in human cancer cell lines of various tissue types. We found that Lappaol F induced G(1) and G(2) cell-cycle arrest, which was associated with strong induction of p21 and p27 and reduction of cyclin B1 and cyclin-dependent kinase 1 (CDK1). Depletion of p21 via genetic knockout or short hairpin RNA (shRNA) approaches significantly abrogated Lappaol F-mediated G(2) arrest and CDK1 and cyclin B1 suppression. These results suggest that p21 seems to play a crucial role in Lappaol F-mediated regulation of CDK1 and cyclin B1 and G(2) arrest. Lappaol F-mediated p21 induction was found to occur at the mRNA level and involved p21 promoter activation. Lappaol F was also found to induce cell death in several cancer cell lines and to activate caspases. In contrast with its strong growth inhibitory effects on tumor cells, Lappaol F had minimal cytotoxic effects on nontumorigenic epithelial cells tested. Importantly, our data also demonstrate that Lappaol F exhibited strong growth inhibition of xenograft tumors in nude mice. Lappaol F was well tolerated in treated animals without significant toxicity. Taken together, our results, for the first time, demonstrate that Lappaol F exhibits antitumor activity in vitro and in vivo and has strong potential to be developed as an anticancer therapeutic.
Natural lignans from Arctium lappa as antiaging agents in Caenorhabditis elegans.[Pubmed:26141518]
Phytochemistry. 2015 Sep;117:340-350.
Arctium lappa is a well-known traditional medicinal plant in China (TCM) and Europe that has been used for thousands of years to treat arthritis, baldness or cancer. The plant produces lignans as secondary metabolites, which have a wide range of bioactivities. Yet, their antiaging potential has not been explored. In this study, we isolated six lignans from A. lappa seeds, namely arctigenin, matairesinol, arctiin, (iso)lappaol A, lappaol C, and Lappaol F. The antioxidant and antiaging properties of the isolated lignans were studied using Caenorhabditis elegans as a relevant animal model. All lignans at concentrations of 10 and 100 muM significantly extended the mean life span of C. elegans. The strongest effect was observed with matairesinol, which at a concentration of 100 muM extended the life span of worms by 25%. Additionally, we observed that five lignans are strong free radical-scavengers in vitro and in vivo and all lignans can improve survival of C. elegans under oxidative stress. Furthermore, the lignans can induce the nuclear translocation of the transcription factor DAF-16 and up-regulate its expression, suggesting that a possible underlying mechanism of the observed longevity-promoting activity of lignans depends on DAF-16 mediated signaling pathway. All lignans up-regulated the expression of jnk-1, indicating that lignans may promote the C. elegans longevity and stress resistance through a JNK-1-DAF-16 cascade. Our study reports new antiaging activities of lignans, which might be candidates for developing antiaging agents.
