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Lupulone Sale

(Synonyms: 蛇床酮) 目录号 : GC47582

A beta-acid

Lupulone Chemical Structure

Cas No.:468-28-0

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1 mg
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10 mg
¥5,396.00
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产品描述

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)

Chemical Properties

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
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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
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Research Update

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.