Zerumbone
(Synonyms: 球姜酮) 目录号 : GC40902
A natural sesquiterpene with diverse effects
Cas No.:471-05-6
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
Zerumbone is a natural monocyclic sesquiterpene first isolated from rhizomes of the wild ginger Z. zerumbet. It potently inhibits the activation of Epstein-Barr virus by phorbol esters (IC50 = 140 nM). Zerumbone inhibits Sonic hedgehog signaling and induces apoptosis in cancer cell lines. It has also been shown to have anti-oxidant and anti-inflammatory activities, contributing to immunomodulatory and hepatoprotective effects.
| Cas No. | 471-05-6 | SDF | |
| 别名 | 球姜酮 | ||
| Canonical SMILES | CC1(C)C/C=C(C)/CC/C=C(C)\C(/C=C/1)=O | ||
| 分子式 | C15H22O | 分子量 | 218.3 |
| 溶解度 | DMSO : ≥ 125 mg/mL (572.53 mM) | 储存条件 | 4°C, protect from light |
| 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 | 4.5809 mL | 22.9043 mL | 45.8085 mL |
| 5 mM | 0.9162 mL | 4.5809 mL | 9.1617 mL |
| 10 mM | 0.4581 mL | 2.2904 mL | 4.5809 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。
Zerumbone Inhibits Helicobacter pylori Urease Activity
Molecules 2021 May 1;26(9):2663.PMID:34062878DOI:10.3390/molecules26092663.
Helicobacter pylori (H. pylori) produces urease in order to improve its settlement and growth in the human gastric epithelium. Urease inhibitors likely represent potentially powerful therapeutics for treating H. pylori; however, their instability and toxicity have proven problematic in human clinical trials. In this study, we investigate the ability of a natural compound extracted from Zingiber zerumbet Smith, Zerumbone, to inhibit the urease activity of H. pylori by formation of urease dimers, trimers, or tetramers. As an oxygen atom possesses stronger electronegativity than the first carbon atom bonded to it, in the Zerumbone structure, the neighboring second carbon atom shows a relatively negative charge (δ-) and the next carbon atom shows a positive charge (δ+), sequentially. Due to this electrical gradient, it is possible that H. pylori urease with its negative charges (such as thiol radicals) might bind to the β-position carbon of Zerumbone. Our results show that Zerumbone dimerized, trimerized, or tetramerized with both H. pylori urease A and urease B molecules, and that this formation of complex inhibited H. pylori urease activity. Although Zerumbone did not affect either gene transcription or the protein expression of urease A and urease B, our study demonstrated that Zerumbone could effectively dimerize with both urease molecules and caused significant functional inhibition of urease activity. In short, our findings suggest that Zerumbone may be an effective H. pylori urease inhibitor that may be suitable for therapeutic use in humans.
Healthy Zerumbone: From Natural Sources to Strategies to Improve Its Bioavailability and Oral Administration
Plants (Basel) 2022 Dec 20;12(1):5.PMID:36616138DOI:10.3390/plants12010005.
Zerumbone is a multifunctional compound with antimicrobial, antitumor, hyperalgesic, antioxidant and anti-inflammatory applications, and constitutes a point molecule for the future synthesis of derivatives with improved efficiency. This monocyclic sesquiterpenoid is found in high content in wild ginger (Zingiber zerumbet Smith), a perennial herb with economic importance as an ornamental as well as a medicinal plant. The presence of Zerumbone is a distinctive feature that allows identification and differentiation from other species, not only in Zingiber, but also in Curcuma, Alpinia, Boesenbergia, Ethlingera and Ammomum spp., as well as related families (Costaceaee). To successfully use Zerumbone in areas such as medicine, food and agriculture, further research on improving its low solubility and bioavailability, as well as its preservation, is a major current priority. In addition, despite its promising pharmacological activities, preclinical and clinical studies are required to demonstrate and evaluate the in vivo efficacy of Zerumbone.
Potential of Zerumbone as an Anti-Cancer Agent
Molecules 2019 Feb 18;24(4):734.PMID:30781671DOI:10.3390/molecules24040734.
Cancer is still a major risk factor to public health globally, causing approximately 9.8 million deaths worldwide in 2018. Despite advances in conventional treatment modalities for cancer treatment, there are still few effective therapies available due to the lack of selectivity, adverse side effects, non-specific toxicities, and tumour recurrence. Therefore, there is an immediate need for essential alternative therapeutics, which can prove to be beneficial and safe against cancer. Various phytochemicals from natural sources have been found to exhibit beneficial medicinal properties against various human diseases. Zerumbone is one such compound isolated from Zingiber zerumbet Smith that possesses diverse pharmacological properties including those of antioxidant, antibacterial, antipyretic, anti-inflammatory, immunomodulatory, as well as anti-neoplastic. Zerumbone has shown its anti-cancer effects by causing significant suppression of proliferation, survival, angiogenesis, invasion, and metastasis through the molecular modulation of different pathways such as NF-κB, Akt, and IL-6/JAK2/STAT3 (interleukin-6/janus kinase-2/signal transducer and activator of transcription 3) and their downstream target proteins. The current review briefly summarizes the modes of action and therapeutic potential of Zerumbone against various cancers.
Tumor-Inhibitory Effects of Zerumbone Against HT-29 Human Colorectal Cancer Cells
Int J Toxicol 2022 Sep-Oct;41(5):402-411.PMID:35719111DOI:10.1177/10915818221104417.
Colorectal cancer (CRC) is the second cause of cancer-associated death globally. Recently, herbal medicinal products and, in particular, Zerumbone have been widely studied and used for cancer treatment as they induce significant anti-cancer effects. However, there is limited information about the anti-cancer effects of Zerumbone in CRC. Therefore, we aimed to investigate the in vitro anti-cancer effects of the Zerumbone in CRC, focusing on cell apoptosis and migration. Anti-proliferative and anti-migratory effects of Zerumbone on HT-29 cells were evaluated using MTT and scratch wound healing assay, respectively. Quantitative real-time PCR (qRT-PCR) was performed to determine the mRNA expression levels of migration and apoptosis-related genes. Apoptosis and cell cycle distribution were evaluated by flow cytometry. The intracellular level of reactive oxygen species (ROS) was measured using a ROS assay kit. Additionally, matrix metalloproteinase-2/-9 (MMP-2/-9) activity was determined using gelatin zymography. Zerumbone suppressed the viability of the HT-29 cells dose-dependently while having less cytotoxicity on normal NIH/3T3 cells. Zerumbone induced apoptosis in HT-29 cells and arrested the cell cycle in the G2/M phase. These effects were associated with alteration in the expression of apoptosis-related genes (up-regulation of Bax and down-regulation of Bcl-2 genes). Zerumbone also enhanced the generation of ROS in HT-29 cells. Furthermore, Zerumbone significantly inhibited the migration of HT-29 cells and decreased MMP-2/-9 mRNA expression and activity. Our findings provide a potential use for Zerumbone to induce apoptosis and suppress metastasis in HT-29 cells; thus, it could be developed as a promising natural agent for future CRC therapy.
Formulation and Nanotechnology-Based Approaches for Solubility and Bioavailability Enhancement of Zerumbone
Medicina (Kaunas) 2020 Oct 23;56(11):557.PMID:33114101DOI:10.3390/medicina56110557.
About 40-70% of drug molecules in the clinical development pipeline suffer from one of either low aqueous solubility, poor absorption, or extremely low bioavailability. Approximately 75% of the world population relies on traditional therapies and therefore there has been a growing interest in the utilization of natural compounds. Zerumbone is one such natural compound, classified as a sesquiterpenoid that is extracted from the essential volatile oils of rhizomes from Zingiber zerumbet. It possesses strong antitumor, antioxidant, antimicrobial, and anti-inflammatory activity. However, despite promising preclinical studies demonstrating the therapeutic utility of Zerumbone, its clinical development has been limited due to its low aqueous solubility, poor absorption, or associated low bioavailability. Multiple reviews demonstrating the pharmacological effects of Zerumbone for various diseases have been published. However, to our knowledge, no review demonstrates the various formulation strategies developed to overcome the biopharmaceutical challenges of Zerumbone. The purpose of this review is to provide a comprehensive perspective on Zerumbone as a molecule for formulation development. A section related to pharmacokinetics, toxicity, and patents of Zerumbone is included. This review provides the importance of developing novel formulations of Zerumbone to overcome its biopharmaceutical challenges thereby advance its potential in the treatment of various diseases.