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Zerumbone Sale

(Synonyms: 球姜酮) 目录号 : GC40902

A natural sesquiterpene with diverse effects

Zerumbone Chemical Structure

Cas No.:471-05-6

规格 价格 库存 购买数量
10mM (in 1mL DMSO)
¥385.00
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5mg
¥350.00
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10mg
¥560.00
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25mg
¥1,120.00
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产品描述

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.

Chemical Properties

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: soluble,Ethanol: soluble 储存条件 4°C, protect from light
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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
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Research Update

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.