Colupulone
(Synonyms: 类蛇麻酮) 目录号 : GC49146
A β-acid with diverse biological activities
Cas No.:468-27-9
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
Colupulone is a β-acid that has been found in H. lupulus and has diverse biological activities.1,2,3 It activates the pregnane X receptor (PXR) in a reporter assay when used at concentrations of 1, 3, and 10 µM.1 Dietary administration of colupulone (0.18% w/w) induces hepatic cytochrome P450 (CYP) isoform 3A (CYP3A) activity in mice.2 It also decreases serum glucose levels in non-diabetic mice and increases serum glucose levels in db/db mice.3
1.Teotico, D.G., Bischof, J.J., Peng, L., et al.Structural basis of human pregnane X receptor activation by the hops constituent colupuloneMol. Pharmacol.74(6)1512-1520(2008) 2.Mannering, G.J., Shoeman, J.A., and Deloria, L.B.Identification of the antibiotic hops component, colupulone, as an inducer of hepatic cytochrome P-4503A in the mouseDrug Metab. Dispos.20(2)142-147(1992) 3.Mannering, G.J., Shoeman, J.A., and Shoeman, D.W.Effects of colupulone, a component of hops and brewers yeast, and chromium on glucose tolerance and hepatic cytochrome P450 in nondiabetic and spontaneously diabetic miceBiochem. Biophys. Res. Commun.200(3)1455-1462(1994)
| Cas No. | 468-27-9 | SDF | |
| 别名 | 类蛇麻酮 | ||
| Canonical SMILES | O=C(C(C)C)C(C(O)=C1C/C=C(C)\C)=C(O)C(C/C=C(C)\C)(C/C=C(C)\C)C1=O | ||
| 分子式 | C25H36O4 | 分子量 | 400.6 |
| 溶解度 | DMSO: soluble,Methanol: soluble | 储存条件 | -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 | 2.4963 mL | 12.4813 mL | 24.9626 mL |
| 5 mM | 0.4993 mL | 2.4963 mL | 4.9925 mL |
| 10 mM | 0.2496 mL | 1.2481 mL | 2.4963 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。
Colupulone, colupone and novel deoxycohumulone geranyl analogues as larvicidal agents against Culex pipiens
Pest Manag Sci 2022 Oct;78(10):4217-4222.PMID:35705833DOI:10.1002/ps.7039.
Background: As climate change proceeds, the management of the population of mosquitoes becomes more and more challenging. Insect adulticides and larvicides constitute significant control techniques, with the latter being considered the leading mosquito control method. However, the development of mosquito resistance development and the adverse side effects caused by the extensive use of synthetic insecticides have turned research towards the discovery of environmentally-friendly solutions. Plants and bacteria have historically proven to be a good source of insecticidally active compounds, which may possess novel modes of action to overcome current resistance mechanisms and could also possess favorable human and environmental safety profiles. A previous study demonstrated that the naturally occurring prenylated acyl phloroglucinol deoxycohumulone is a potent larvicidal agent against Culex pipiens. Herein the structural characteristics that improve it are explored by evaluating Colupulone and novel geranylated analogues. Results: Colupulone, a prenylated acyl phloroglucinol isolated from Humulus lupulus, colupone, and novel geranylated acyl phloroglucinol congeners, were synthesized and evaluated against Cx. pipiens larva. Results indicated that selected derivatives exhibited superior potency than deoxycohumulone (LC50 43.7 mg L-1 ). Thus, strong activity was observed for Colupulone (LC50 19.7 mg L-1 ), and some novel geranyl analogues of deoxycohumulone reaching at LC50 17.1 mg L-1 , while colupone and similar compounds were almost inactive. Conclusion: The results determined the relationship between the target activity and the chemical structure of the tested compounds, and they revealed significantly improved larvicidal candidates. These results highlight the potential of the acyl phloroglucinol chemistry for further development of mosquito larvicides. © 2022 Society of Chemical Industry.
The effect of Colupulone (a HOPS beta-acid) on hepatic cytochrome P-450 enzymatic activity in the rat
Food Chem Toxicol 1994 Nov;32(11):1007-14.PMID:7959454DOI:10.1016/0278-6915(94)90140-6.
Colupulone, a component of hops, was examined for its ability to alter rat hepatic cytochrome P-450 enzymatic activity, expression of hepatic cytochrome P-450 mRNA, and in vitro promutagen activation. Colupulone was fed to male Sprague-Dawley rats for 5 days at 0.36% in the modified AIN 76 diet. Three cytochrome P-450 enzymatic activities were measured, and the corresponding steady-state mRNA levels were examined by Northern blot hybridization. Colupulone increased cytochrome P450IIB and P450IIIA steady-state mRNA levels. In vitro promutagen activation was measured in the Ames assay using liver homogenates from each treatment group. Colupulone treatment did not alter the ex vivo cytochrome P-450-mediated activation of aflatoxin B1 or benzo[a]pyrene to their mutagenic forms. The effect of long-term Colupulone administration on in vivo cytochrome P-450 enzymatic activity remains to be determined.
Synthesis and P-glycoprotein induction activity of Colupulone analogs
Org Biomol Chem 2015 May 21;13(19):5488-96.PMID:25875530DOI:10.1039/c5ob00554j.
Brain amyloid-beta (Aβ) plaques are one of the primary hallmarks associated with Alzheimer's disease (AD) pathology. Efflux pump proteins located at the blood-brain barrier (BBB) have been reported to play an important role in the clearance of brain Aβ, among which the P-glycoprotein (P-gp) efflux transporter pump has been shown to play a crucial role. Thus, P-gp has been considered as a potential therapeutic target for treatment of AD. Colupulone, a prenylated phloroglucinol isolated from Humulus lupulus, is known to activate pregnane-X-receptor (PXR), which is a nuclear receptor controlling P-gp expression. In the present work, we aimed to synthesize and identify analogs of Colupulone that are potent P-gp inducer(s) with an ability to enhance Aβ transport across the BBB. A series of Colupulone analogs were synthesized by modifications at both prenyl as well as acyl domains. All compounds were screened for P-gp induction activity using a rhodamine 123 based efflux assay in the P-gp overexpressing human adenocarcinoma LS-180 cells, wherein all compounds showed significant P-gp induction activity at 5 μM. In the western blot studies in LS-180 cells, compounds 3k and 5f were able to induce P-gp as well as LRP1 at 1 μM. The effect of compounds on the Aβ uptake and transport was then evaluated. Among all tested compounds, diprenylated acyl phloroglucinol displayed a significant increase (29%) in Aβ transport across bEnd3 cells grown on inserts as a BBB model. The results presented here suggest the potential of this scaffold to enhance clearance of brain Aβ across the BBB and thus its promise for development as a potential anti-Alzheimer agent.
Effects of Colupulone, a component of hops and brewers yeast, and chromium on glucose tolerance and hepatic cytochrome P450 in nondiabetic and spontaneously diabetic mice
Biochem Biophys Res Commun 1994 May 16;200(3):1455-62.PMID:8185600DOI:10.1006/bbrc.1994.1614.
Brewers yeast contains factors that increase and decrease glucose tolerance. Hop components (lupulones) that adhere to yeast during the brewing process elicit a variety of biological effects including the induction of hepatic cytochrome P4503A. Colupulone was tested for its effects on glucose tolerance and cytochrome P450. Serum glucose levels 30 min after the injection of glucose were lowered by Colupulone in nondiabetic Swiss-Webster mice, elevated in diabetic C57B1/KSJ-db/db mice, and unaffected in nondiabetic C57B1/KSJ+m/+m mice. Colupulone lowered hemoglobin glycation slightly in +m/+m mice but not in db/db mice. The cytochrome P450 system was highly induced by Colupulone in both db/db and +m/+m mice. Chromium, which acts in concert with the factor in yeast that enhances glucose tolerance, had little or no effect on the plasma glucose level or the cytochrome P450 system in either +m/+m or db/db mice.
Structural basis of human pregnane X receptor activation by the hops constituent Colupulone
Mol Pharmacol 2008 Dec;74(6):1512-20.PMID:18768384DOI:10.1124/mol.108.050732.
Hops extracts are used to alleviate menopausal symptoms and as an alternative to hormone replacement therapy, but they can produce potentially harmful drug-drug interactions. The nuclear xenobiotic receptor pregnane X receptor (PXR) is promiscuously activated by a range of structurally distinct chemicals. It has a key role in the transcriptional regulation of genes that encode xenobiotic metabolism enzymes. In this study, hops extracts are shown to induce the expression of numerous drug metabolism and excretion proteins. The beta-bitter acid Colupulone is demonstrated to be a bioactive component and direct activator of human PXR. The 2.8-A resolution crystal structure of the ligand binding domain of human PXR in complex with Colupulone was elucidated, and Colupulone was observed to bind in a single orientation stabilized by both van der Waals and hydrogen bonding contacts. The crystal structure also indicates that related alpha- and beta-bitter acids have the capacity to serve as PXR agonists as well. Taken together, these results reveal the structural basis for drug-drug interactions mediated by Colupulone and related constituents of hops extracts.