LupulonCAS# 468-28-0 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 468-28-0 | SDF | Download SDF |
| PubChem ID | 68051 | Appearance | Powder |
| Formula | C26H38O4 | M.Wt | 414.6 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one | ||
| SMILES | CC(C)CC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)CC=C(C)C)O | ||
| Standard InChIKey | LSDULPZJLTZEFD-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28-29H,10,13-15H2,1-8H3 | ||
| 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. | ||
Lupulon Dilution Calculator
Lupulon Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.412 mL | 12.0598 mL | 24.1196 mL | 48.2393 mL | 60.2991 mL |
| 5 mM | 0.4824 mL | 2.412 mL | 4.8239 mL | 9.6479 mL | 12.0598 mL |
| 10 mM | 0.2412 mL | 1.206 mL | 2.412 mL | 4.8239 mL | 6.0299 mL |
| 50 mM | 0.0482 mL | 0.2412 mL | 0.4824 mL | 0.9648 mL | 1.206 mL |
| 100 mM | 0.0241 mL | 0.1206 mL | 0.2412 mL | 0.4824 mL | 0.603 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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Differential role of apoptosis and autophagy associated with anticancer effect of lupulone (hop beta-acid) derivatives on prostate cancer cells.[Pubmed:24954859]
Anticancer Agents Med Chem. 2014;14(8):1169-78.
Lupulone, a beta-acid derived from hop extracts has been shown to exhibit cytotoxic activity against cancer cells. In this study we investigated the functional role of different modes of cell death that mediate anticancer effect of Lupulone derivatives in prostate cancer cells. ELISA, immunoblotting and siRNA approaches were utilised to study cell death, expression of proteins of interest and their functional activities. We found that the anticancer effect of Lupulone derivatives on prostate cancer cells is associated with induction of apoptosis and autophagy as determined by increases of DNA fragmentation and LC3I/ LC3II conversion respectively. Inhibition of apoptosis using a pan-caspase inhibitor resulted in increased levels of autophagy. Following screening of proteins associated with autophagy we found that Atg4beta expression was increased in prostate cancer cells after treatment with Lupulone. Transfection of cells with siRNA against Atg4beta resulted in increased levels of apoptosis in prostate cancer cells. Treatment of prostate cancer cells with Lupulone derivatives initiated two modes of cell death: apoptosis as a killing pathway and autophagy as a protection against cell death. Further studies are required to investigate the regulation of Atg4beta activity in Lupulone derivatives-induced negative crosstalk between apoptosis and autophagy.
An investigation into the anticancer effects and mechanism of action of hop beta-acid lupulone and its natural and synthetic derivatives in prostate cancer cells.[Pubmed:24168111]
Nutr Cancer. 2013;65(7):1086-92.
Lupulone, a beta-acid derived from hop extracts has been shown to exhibit antibacterial and anticancer activity. In this study we investigated the anticancer potency of Lupulone and its novel derivatives and their mechanism of action on prostate cancer cells. Cell viability was determined using the MTT assay, and the ELISA approach was used to investigate induction of apoptosis. Immunoblot analysis was carried out to determine activation and regulation of proteins associated with cell death. Screening of natural and new Lupulone derivatives for their anticancer activity demonstrated that one (Lupulone derivative 1h) displayed stronger anticancer activity than Lupulone itself on PC3 and DU145 prostate cancer cells. We further found that Lupulone derivatives induced caspase-dependent apoptosis that is associated with activation of caspases 8, 9, and 3. Furthermore, caspase 8 inhibitor Z-IETD-fmk reduced cell death induced by Lupulone derivatives, suggesting that apoptosis is mediated by caspase 8. Finally, we found that Lupulone and its synthetic derivatives also increased formation of LC3II suggesting that autophagy is also implicated in prostate cancer cell death. The new Lupulone derivatives induce caspase-dependent apoptosis and autophagy in prostate cancer cells and appear to be good candidates for further preclinical studies of prostate cancer treatment.
Genome-wide transcription analyses in Mycobacterium tuberculosis treated with lupulone.[Pubmed:24948953]
Braz J Microbiol. 2014 Apr 18;45(1):333-41.
Mycobacterium tuberculosis (M. tuberculosis), the causative agent of tuberculosis, still causes higher mortality than any other bacterial pathogen until now. With the emergence and spread of multidrug-resistant (MDR) and extensively drug-resistant (XDR-TB) strains, it becomes more important to search for alternative targets to develop new antimycobacterial drugs. Lupulone is a compound extracted from Hops (Hurnulus lupulus), which exhibits a good antimicrobial activity against M. tuberculosis with minimal inhibitory concentration (MIC) value of 10 mug/mL, but the response mechanisms of Lupulone against M. tuberculosis are still poorly understood. In this study, we used a commercial oligonucleotide microarray to determine the overall transcriptional response of M. tuberculosis H37Rv triggered by exposure to MIC of Lupulone. A total of 540 genes were found to be differentially regulated by Lupulone. Of these, 254 genes were upregulated, and 286 genes were downregulated. A number of important genes were significantly regulated which are involved in various pathways, such as surface-exposed lipids, cytochrome P450 enzymes, PE/PPE multigene families, ABC transporters, and protein synthesis. Real-time quantitative RT-PCR was performed for choosed genes to verified the microarray results. To our knowledge, this genome-wide transcriptomics approach has produced the first insights into the response of M. tuberculosis to a Lupulone challenge.
