Xanthohumol D
目录号 : GC37939
Xanthohumol D，分离于酒花，是一种醌还原酶2 (QR-2) 抑制剂，IC50 为110 μM，并与 QR-2 活性位点结合。Xanthohumol D 在体外对人癌细胞株有抗增殖作用。
Cas No.:274675-25-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Xanthohumol D, isolated from hops, is an inhibitor of quinone reductase-2 (QR-2) with the IC50 value of 110 μM, and binds to the active site of QR-2. Xanthohumol D shows antiproliferative activity on human cancer cell lines in vitro[1][2]. IC50: 110 μM (Quinone reductase-2)[1]
[1]. Choi Y, et al. Screening natural products for inhibitors of quinone reductase-2 using ultrafiltration LC-MS. Anal Chem. 2011 Feb 1;83(3):1048-52. [2]. Tronina T, et al. Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro. Bioorg Med Chem. 2013 Apr 1;21(7):2001-6.
| Cas No. | 274675-25-1 | SDF | |
| Canonical SMILES | O=C(C1=C(OC)C=C(O)C(CC(O)C(C)=C)=C1O)/C=C/C2=CC=C(O)C=C2 | ||
| 分子式 | C21H22O6 | 分子量 | 370.4 |
| 溶解度 | Soluble in DMSO | 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 | 2.6998 mL | 13.4989 mL | 26.9978 mL |
| 5 mM | 0.54 mL | 2.6998 mL | 5.3996 mL |
| 10 mM | 0.27 mL | 1.3499 mL | 2.6998 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。
Fungal metabolites of xanthohumol with potent antiproliferative activity on human cancer cell lines in vitro
Bioorg Med Chem 2013 Apr 1;21(7):2001-6.PMID:23434138DOI:10.1016/j.bmc.2013.01.026.
Xanthohumol (1) and Xanthohumol D (2) were isolated from spent hops. Isoxanthohumol (3) was obtained from xanthohumol by isomerisation in alkaline solution. Six metabolites were obtained as a result of transformation of xanthohumol (1) by selected fungal cultures. Their structures were established on the basis of their spectral data. One of them: 2″-(2'''-hydroxyisopropyl)-dihydrofurano-[4″,5″:3',4']-4',2-dihydroxy-6'-methoxy-α,β-dihydrochalcone (6) has not been previously reported in the literature. The antioxidant properties of hops flavonoids and xanthohumol derivatives were investigated using the 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method. The effects of these compounds on proliferation of MCF-7, PC-3 and HT-29 human cancer cell lines were determined by the SRB assay. With the exception of one metabolite, all tested compounds showed antiproliferative activity against the tested human cancer lines. α,β-Dihydroxanthohumol (4), obtained through the biotransformation of xanthohumol, showed higher antiproliferative activity against MCF-7 human breast carcinoma cell line than cisplatin, a widely used anticancer therapeutic agent, and a comparably high activity against PC-3 human prostate cancer cell line.
Screening natural products for inhibitors of quinone reductase-2 using ultrafiltration LC-MS
Anal Chem 2011 Feb 1;83(3):1048-52.PMID:21192729DOI:10.1021/ac1028424.
Inhibitors of quinone reductase-2 (NQO2; QR-2) can have antimalarial activity and antitumor activities or can function as chemoprevention agents by preventing the metabolic activation of toxic quinones such as menadione. To expedite the search for new natural product inhibitors of QR-2, we developed a screening assay based on ultrafiltration liquid chromatography-mass spectrometry that is compatible with complex samples such as bacterial or botanical extracts. Human QR-2 was prepared recombinantly, and the known QR-2 inhibitor, resveratrol, was used as a positive control and as a competitive ligand to eliminate false positives. Ultrafiltration LC-MS screening of extracts of marine sediment bacteria resulted in the discovery of tetrangulol methyl ether as an inhibitor of QR-2. When applied to the screening of hop extracts from the botanical, Humulus lupulus L., xanthohumol and Xanthohumol D were identified as ligands of QR-2. Inhibition of QR-2 by these ligands was confirmed using a functional enzyme assay. Furthermore, binding of xanthohumol and Xanthohumol D to the active site of QR-2 was confirmed using X-ray crystallography. Ultrafiltration LC-MS was shown to be a useful assay for the discovery of inhibitors of QR-2 in complex matrixes such as extracts of bacteria and botanicals.
Screening method for the discovery of potential cancer chemoprevention agents based on mass spectrometric detection of alkylated Keap1
Anal Chem 2005 Oct 1;77(19):6407-14.PMID:16194107DOI:10.1021/ac050892r.
Natural products are important sources of drugs such as cancer chemopreventive agents, but most assays for the discovery of compounds in natural product extracts are low throughput and provide little information about lead compounds in these complex mixtures. The induction of enzymes such as quinone reductase, glucuronyl transferases, glutathione S-transferases, and sulfotransferases can protect cells against the toxic and neoplastic effects of carcinogens. An increase in the concentration of Nrf2 in the nucleus of a cell upregulates the antioxidant response element and induces the expression of these chemopreventive enzymes. Based on the hypothesis that ubiquitination and proteosome-mediated degradation of Nrf2 in the cytoplasm decreases upon the covalent modification of 1 or more of the 27 cysteine sulfhydryl groups on Keap1 (a protein that sequesters Nrf2 in the cytoplasm) and results in higher Nrf2 levels both in the cytoplasm and in the nucleus, a high-throughput mass spectrometry-based screening assay was designed to detect alkylation of sulfhydryl groups of human Keap1. As an initial high-throughput screening step, matrix-assisted laser desorption time-of-flight mass spectrometry was used to determine whether incubation of Keap1 with a botanical sample produced adducts of Keap1. Test extracts found to form adducts with Keap1 were then incubated with the alternative biological nucleophile glutathione and characterized using LC-UV-MS-MS. After validation of the assay using two model alkylating agents, fractions of an extract of hops (Humulus lupulus L.) from the brewing industry were screened, and several compounds were detected as potential chemopreventive agents. Two of these electrophilic hops constituents were identified as xanthohumol and Xanthohumol D. In a subsequent cell-based assay, xanthohumol and Xanthohumol D were confirmed to be potent inducers of quinone reductase, and reaction with Keap1 was also confirmed. Therefore, this new mass spectrometric screening assay was demonstrated to facilitate the discovery of chemoprevention agents in complex natural product mixtures.