Zingiberene
(Synonyms: α-Zingiberene; (-)-Zingiberene) 目录号 : GC61472
Zingiberene(α-Zingiberene)是一种单环倍半萜烯，是姜油的主要成分。具有神经保护潜能。Zingiberene能诱导自噬(autophagy)。具有抗癌活性。
Cas No.:495-60-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Zingiberene (α-Zingiberene) is a monocyclic sesquiterpene which is the predominant constituent of ginger with oil content (Zingiber officinale). Neuroprotective potential[1]. Zingiberene triggers autophagy. Anticancer activity[2].
Zingiberene (6.25, 12.5, 25, 50 and 100 μg/mL; 24 hours) attenuates hydrogen peroxide-induced toxicity in neuronal cells[1]. Zingiberene (0, 10, 20 and 40 µM; 24 hours) considerably inhibits the proliferation of Colon cancer (CC) cells[2].
[1]. B Togar, et al. Zingiberene attenuates hydrogen peroxide-induced toxicity in neuronal cells. Hum Exp Toxicol. 2015 Feb;34(2):135-44. [2]. Hai Chen, Zingiberene inhibits in vitro and in vivo human colon cancer cell growth via autophagy induction, suppression of PI3K/AKT/mTOR Pathway and caspase 2 deactivation. J BUON. Jul-Aug 2019;24(4):1470-1475.
| Cas No. | 495-60-3 | SDF | |
| 别名 | α-Zingiberene; (-)-Zingiberene | ||
| Canonical SMILES | CC1=CC[C@H]([C@@H](C)CC/C=C(C)\C)C=C1 | ||
| 分子式 | C15H24 | 分子量 | 204.35 |
| 溶解度 | 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 | 4.8936 mL | 24.4678 mL | 48.9356 mL |
| 5 mM | 0.9787 mL | 4.8936 mL | 9.7871 mL |
| 10 mM | 0.4894 mL | 2.4468 mL | 4.8936 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。
Zingiberene exerts chemopreventive activity against 7,12-dimethylbenz(a)anthracene-induced breast cancer in Sprague-Dawley rats
J Biochem Mol Toxicol 2022 Oct;36(10):e23146.PMID:35698847DOI:10.1002/jbt.23146.
Breast cancer is the primary cause of cancer-related death in females, wherein increased mortality of breast cancer patients is recorded worldwide. Zingiberene is a monocyclic sesquiterpene from the ginger plant and has many pharmacological benefits. In this exploration, we assessed the anticancer actions of Zingiberene against the 7,12-dimethylbenz(a)anthracene (DMBA)-stimulated mammary carcinogenesis in rats and MDA-MB-231 cells. Breast cancer was induced in the Female Sprague-Dawley rats through the 25 mg/kg of DMBA in 0.5 ml of corn oil and then treated with 20 and 40 mg/kg of Zingiberene, respectively. The body weight of animals and tumor volume was measured. Hematological parameters, transaminases, lipid profile, lipid peroxidation, and antioxidants status were scrutinized using standard techniques. The estrogen receptor-α and inflammatory markers were inspected by using respective assay kits. Histological damage scores were determined. In vitro experiments were conducted to scrutinize Zingiberene's effect on cell viability and apoptotic cell death in MDA-MB-231 cells. Zingiberene substantially modulated the DMBA-stimulated physiological and hematological changes and decreased the transaminases, and lipid peroxidation in the DMBA-stimulated animals. Zingiberene also elevated the antioxidant level and suppressed the inflammatory markers. Histological study revealed the protective effects of Zingiberene. The viability of MDA-MB-231 cells was noticeably diminished by the Zingiberene, thus inducing apoptotic cell death. Overall, our findings reliably proved the anticancer potential of Zingiberene against the DMBA-stimulated mammary tumorigenesis, and it could be a promising chemotherapeutic agent.
Antibacterial Activity and Mechanism of Ginger Essential Oil against Escherichia coli and Staphylococcus aureus
Molecules 2020 Aug 30;25(17):3955.PMID:32872604DOI:10.3390/molecules25173955.
Though essential oils exhibit antibacterial activity against food pathogens, their underlying mechanism is understudied. We extracted ginger essential oil (GEO) using supercritical CO2 and steam distillation. A chemical composition comparison by GC-MS showed that the main components of the extracted GEOs were Zingiberene and α-curcumene. Their antibacterial activity and associated mechanism against Staphylococcus aureus and Escherichia coli were investigated. The diameter of inhibition zone (DIZ) of GEO against S. aureus was 17.1 mm, with a minimum inhibition concentration (MIC) of 1.0 mg/mL, and minimum bactericide concentration (MBC) of 2.0 mg/mL. For E. coli, the DIZ was 12.3 mm with MIC and MBC values of 2.0 mg/mL and 4.0 mg/mL, respectively. The SDS-PAGE analysis revealed that some of the electrophoretic bacterial cell proteins bands disappeared with the increase in GEO concentration. Consequently, the nucleic acids content of bacterial suspension was raised significantly and the metabolic activity of bacteria was markedly decreased. GEO could thus inhibit the expression of some genes linked to bacterial energy metabolism, tricarboxylic acid cycle, cell membrane-related proteins, and DNA metabolism. Our findings speculate the bactericidal effects of GEO primarily through disruption of the bacterial cell membrane indicating its suitability in food perseveration.
Zingiberene inhibits in vitro and in vivo human colon cancer cell growth via autophagy induction, suppression of PI3K/AKT/mTOR Pathway and caspase 2 deactivation
J BUON 2019 Jul-Aug;24(4):1470-1475.PMID:31646793doi
Purpose: Colon cancer (CC) is one of the deadly malignancies and the second most frequent cancer in the world. The development of drug resistance and dearth of the viable drug options form a serious obstacle in the treatment of CC. Herein, the anticancer potential of Zingiberene was examined against the CC cells. Methods: The proliferation rate of the CC cells was assessed by cell counting assay. Autophagy was detected by transmission electron microscopy (TEM). The transfected cells were then treated with varied concentrations of Zingiberene (0, 10, 20 and 40 µM) for 24 h and monitored by fluorescent microscopy. Cell cycle analysis was performed by flow cytometry. Protein expression was determined by immunoblotting. Results: Zingiberene could considerably inhibit the proliferation of CC cells. The anticancer activity of Zingiberene against the HT-29 CC cells was found to be due to induction of autophagy. The Zingiberene triggered autophagy was also linked with increase in the expression of LC3-II and decrease in p62 expression. However, no apparent effects were observed on the LC3-I expression. Moreover, it was found that zingiberine also caused activation of autophagy-related caspases in the HT-29 cells. Further, it was found that Zingiberene could inhibit the mTOR/PI3K/AKT signalling pathway in the CC cells. Zingiberene also suppressed the weight and volume of the xenografted tumors concentration-dependently. Conclusions: These results indicate that Zingiberene may inhibit the growth of CC in vitro and in vivo and may be used for the development of systemic therapy against CC.
Zingiberene and curcumene in wild tomato
J Environ Sci Health B 2003 Jul;38(4):489-500.PMID:12856930DOI:10.1081/PFC-120021668.
Composition of ginger oil prepared from fresh ginger rhizomes, Zingiber officinale Roscoe (Zingiberaceae) was determined by gas chromatography (GC) and GC-mass spectrometric techniques. The main sesquiterpene hydrocarbons identified were alpha-zingiberene (27-30%), alpha-curcumene (8-9%), beta-sesquiphellandrene (4.8%). and bisabolene (3.2%). The function of Zingiberene and curcumene as insecticides, repellents, and insect feeding deterrents has been previously reported. Other plant species having similar constituents might be found. Leaves of six wild tomato accessions of Lycopersicon hirsutum f. glabratum (Mull); three accessions of L. hirsutum f. typicum (Humb & Bonpl.); two accessions of L. pennellii Corr. (D'Arcy); one accession of L. pimpinellifolium; and one commercial tomato L. esculentumm cv. Fabulous were analyzed. Analysis of L. hirsutum f. typicum (Solanaceae) accessions indicated the presence of Zingiberene, curcumene, and other lipophilic secondary metabolites in the leaves of two accessions (PI-127826 and PI-127827). An average three month old wild tomato plant of accessions PI-127826 and PI-127827 provided 1.93 and 1.30 kg fresh leaves (averaging about 38,307 and 28,130 cm2 exposed leaf surface area, respectively) and produced 19.3 and 10.1 g of Zingiberene and curcumene (PI-127826) and 17.2 and 1.8 g of Zingiberene and curcumene (PI-127827), respectively. Leaf extracts of the wild tomato L. hirsutum f. typicum (accessions PI-127826 and PI-127827) can be used as a biorational source of Zingiberene and curcumene.
Zingiberene targets the miR-16/cyclin-B1 axis to regulate the growth, migration and invasion of human liver cancer cells
J BUON 2020 Jul-Aug;25(4):1904-1910.PMID:33099931doi
Purpose: Liver cancer or hepatocellular carcinoma (HCC) is considered as one of the most frequent malignancies with significantly high morbidity and mortality across the globe. MicroRNAs (miRs) are regarded as important regulators of liver cancer formation and its development. However, the full biochemical mechanism of their role is still very less understood. The main objective of the current research work was to examine the role of miR-16/cyclin-B1 axis in liver cancer regulation and how this pathway along with liver cancer migration and invasion are targeted by Zingiberene molecule. Methods: Quantitative reverse transcriptase polymerase chain reaction was used to evaluate miR-16 expression in HCC cell lines. Western blotting was performed to evaluate the expression of the miR-16 target genes. Effects on cell migration and invasion were evaluated by in vitro wound healing assay and transwell Matrigel assay, respectively. Effects of Zingiberene on HCC cell viability were evaluated by MTT assay. Results: Zingiberene treatment led to downregulation of miR-16 in HepG2 human hepatocellular carcinoma cells, accompanied by induction of G0/G1 cell cycle arrest targeting cyclin B1 as direct target. These effects were also accompanied by inhibition of cell migration and invasion, indicating that miR-16 can have a significant role as liver cancer suppressor after Zingiberene treatment. Luciferase reporter assay confirmed that miR-16, which was one of HCC downregulated miRs, directly targeted Cyclin B1 in HCC cells. Conclusion: The current study indicates miR-16/cyclin B1 axis might have significant applications as a therapeutic target for patients with liver cancer.