Lupulone
(Synonyms: 蛇床酮) 目录号 : GC47582
A beta-acid
Cas No.:468-28-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Lupulone is a beta-acid that has been found in the hop plant, H. lupulus, and has diverse biological activities, including antibacterial, antioxidant, and anticarcinogenic properties.1,2,3 Lupulone is active against B. subtilis and S. aureus (MICs = 1 and 1.2 µg/ml, respectively), as well as T. b. brucei and L. m. mexicana (IC50s = 0.9 and 4.7 µg/ml, respectively).1,2 It scavenges 2,2-diphenyl-1-picrylhydrazyl radicals in a cell-free assay and inhibits lipid peroxidation in rat brain homogenates (IC50s = 25 and 39 µM, respectively).4 It reduces proliferation, migration, and capillary tube formation in human umbilical vein endothelial cells (HUVECs) when used at concentrations ranging from 2.5 to 50 µg/ml.5 Lupulone (40 µg/ml) activates the extrinsic apoptotic death pathway in SW480 and SW620 colon cancer cells.3
1.Teuber, M., and Schmalreck, A.F.Membrane leakage in Bacillus subtilis 168 induced by the hop constituents lupulone, humulone, isohumulone and humulinic acidArch. Mikrobiol.94(2)159-171(1973) 2.Bocquet, L., Sahpaz, S., Bonneau, N., et al.Phenolic compounds from Humulus lupulus as natural antimicrobial products: New weapons in the fight against methicillin resistant Staphylococcus aureus, Leishmania mexicana and Trypanosoma brucei strainsMolecules24(6)1024(2019) 3.Lamy, V., Roussi, S., Chaabi, M., et al.Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cellsApoptosis13(10)1232-1242(2008) 4.Tagashira, M., Watanabe, M., and Uemitsu, N.Antioxidative activity of hop bitter acids and their analoguesBiosci. Biotechnol. Biochem.59(4)740-742(1995) 5.Siegel, L., Miternique-Grosse, A., Griffon, C., et al.Antiangiogenic properties of lupulone, a bitter acid of hop conesAnticancer Res.28(1A)289-294(2008)
| Cas No. | 468-28-0 | SDF | |
| 别名 | 蛇床酮 | ||
| Canonical SMILES | O=C1C(C/C=C(C)/C)(C/C=C(C)/C)C(O)=C(C(CC(C)C)=O)C(O)=C1C/C=C(C)/C | ||
| 分子式 | C26H38O4 | 分子量 | 414.6 |
| 溶解度 | Methanol: slightly soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.412 mL | 12.0598 mL | 24.1196 mL |
| 5 mM | 0.4824 mL | 2.412 mL | 4.8239 mL |
| 10 mM | 0.2412 mL | 1.206 mL | 2.412 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells
Apoptosis 2008 Oct;13(10):1232-42.PMID:18726190DOI:10.1007/s10495-008-0250-5.
Our study aimed to compare death signalling pathways triggered by Lupulone in TRAIL-sensitive human colon cancer cells (SW480) and in their derived TRAIL-resistant metastatic cells (SW620). Lupulone (40 microg/ml) up-regulated expression of TRAIL DR4/DR5 death receptors at the cell surface of both cell lines, even in the absence of exogenous TRAIL ligand. Cell death induced by Lupulone was inhibited in SW480 and SW620 cells exposed to blocking anti-DR4/DR5 antibodies. In SW480 cells, Lupulone triggered cell death through a cross-talk between TRAIL-DR4/DR5 and the mitochondrial (intrinsic) pathways involving caspase-8 activation and Bid protein cleavage. As a consequence mitochondrial cytochrome c was released into the cytosol and activation of caspases-9 and -3 was observed. In the metastatic SW620 cells, Lupulone restored the sensibility of these cells to TRAIL ligand and activated the extrinsic apoptotic pathway via DR4/DR5 death receptors and the involvement of the caspase-8/caspase-3 cascade. The demonstration that Lupulone is able to activate TRAIL-death signalling pathways even in TRAIL resistant cancer cells highlights the potential of this natural compound for cancer prevention and therapy.
Lupulone triggers p38 MAPK-controlled activation of p53 and of the TRAIL receptor apoptotic pathway in human colon cancer-derived metastatic cells
Oncol Rep 2011 Jul;26(1):109-14.PMID:21519792DOI:10.3892/or.2011.1273.
We previously reported that the chemopreventive agent Lupulone induces apoptosis through activation of the extrinsic pathway via TRAIL DR4/DR5 death receptors overcoming SW620 cell resistance to TRAIL. However, the underlying molecular mechanisms remain unknown. Since the mitogen-activated protein kinases (MAPKs), Jun N-terminal kinase (JNK), extracellular signal-regulated kinase (ERK) and p38 control fundamental cellular processes such as apoptosis, we determined the role of these MAPKs in lupulone-triggered apoptosis. We analyzed the effects of JNK, ERK and p38 MAPK inhibitors on lupulone-induced apoptosis by flow cytometry using specific antibodies and real-time RT-PCR. Our data showed that among the MAPKs, only p38 played a major role in lupulone-triggered apoptosis. In contrast to JNK and ERK inhibition, the specific inactivation of p38 inhibited the lupulone-triggered up-regulation of p53 and TRAIL-death receptor DR4/DR5 expression, and prevented DNA fragmentation. Lupulone treatment enhanced the expression of the anti-apoptotic Mcl-1 protein by 60% favoring the preservation of mitochondrial integrity. The inactivation of p38 initiated a 50% reduction in Mcl-1, Bcl-2 and Bax expression without changing the Mcl-1/Bax ratio suggesting that p38 was not involved in the protective effect of Lupulone on mitochondria. Our data support the view that the lupulone-triggered enhanced expression of p38 plays a major role in the activation of p53 and of the TRAIL-death receptor apoptotic pathway in SW620 human colon cancer-derived metastatic cells.
Antiangiogenic properties of Lupulone, a bitter acid of hop cones
Anticancer Res 2008 Jan-Feb;28(1A):289-94.PMID:18383859doi
Background: Angiogenesis is the result of intricate steps regulated by the balance between agonistic and antagonistic effectors. Disturbance of this balance leads to an 'angiogenic' switch critical for tumor development. Materials and methods: Using human umbilical vein endothelial cells (HUVEC) the effects of Lupulone were analyzed on proliferation induced by angiogenic growth factors, transmembrane cell migration toward fibronectin and formation of a network of tubular-like structures on Matrigel. Results: Lupulone (2.5-50 microg/ml) induced a concentration-dependent inhibition of HUVEC proliferation and chemotaxis. Lupulone caused a significant reduction of closed capillary-like structures in Matrigel indicating a strong inhibitory effect on neovascularisation. In mice receiving Lupulone (20 mg/kg/day) in drinking water for 21 days, new vessel formation was reduced by 50% in matrigel plugs implanted under the skin when compared with controls. Conclusion: The present data demonstrate that Lupulone is able to inhibit angiogenesis in vitro and in vivo. Lupulone emerges as a potential chemopreventive agent when considering its strong antiangiogenic properties.
Quantification of co-, n-, and ad-lupulone in hop-based dietary supplements and phytopharmaceuticals and modulation of their contents by the extraction method
J Pharm Biomed Anal 2019 May 10;168:124-132.PMID:30807916DOI:10.1016/j.jpba.2019.02.022.
Hop β-bitter acids (lupulones) are health-beneficial components of Humulus lupulus L. showing, for example, antidepressant-like effects in vitro. Despite of the widespread use of hops for medicinal purposes, the concentrations of lupulones in hop-based drugs have not been reported yet. The present study developed, validated, and applied a method with external calibration, which allows for the first time separate quantification of co-, n-, and ad-lupulone in hop-based drugs by UHPLC‒DAD. Concentrations between 'not detectable' and 2.7 mg/mL co-lupulone, 2.2 mg/mL nlupulone, or 0.7 mg/mL ad-lupulone were measured in nine different commercial dietary supplements and phytopharmaceuticals. Only one hop tincture contained sufficient Lupulone to possibly exert potential antidepressant effects. Aiming for products with increased Lupulone content, the extraction efficiency of different solvents was investigated. Complete extraction of lupulones from raw hops was achieved by organic solvents including methanol and ethanol, whereas aqueous mixtures resulted in low recovery. These results indicate that adapted extraction conditions may result in more effective hops products.
Antimicrobial activity of Lupulone against Clostridium perfringens in the chicken intestinal tract jejunum and caecum
J Antimicrob Chemother 2008 Apr;61(4):853-8.PMID:18276602DOI:10.1093/jac/dkn024.
Objectives: Owing to the spread of antibiotic resistance among human infectious agents, there is a need to research antibiotic alternatives for use in animal agricultural systems. Antibiotic-free broiler chicken production systems are known to suffer from frequent outbreaks of necrotic enteritis due in part to pathogenic type A Clostridium perfringens. Hop (Humulus lupulus) bitter acids are known to possess potent antimicrobial activity. Lupulone was evaluated for in vivo antimicrobial activity to inhibit C. perfringens in a chick gastrointestinal colonization model. Methods: Using a week-2 per os inoculated C. perfringens chicken colonization model, C. perfringens counts in mid-intestinal and caecal contents were compared between chickens administered Lupulone at 62.5, 125 and 250 ppm in drinking water versus 0 ppm control. Results At day 22, post-hatch intestinal C. perfringens counts of lupulone-treated chickens were significantly lower (P < 0.05) than water-treated control groups in both jejunal and caecal sampling sites across all Lupulone dosages tested. Conclusions: Lupulone administered through water inhibits gastrointestinal levels of inoculated pathogenic clostridia within the chicken gastrointestinal tract. Lupulone was effective within the chemically complex mixture of material within the gastrointestinal tract, thereby making this agent a target of further research as an antibiotic alternative for this and possibly other intestinal infections.