8-Gingerol
(Synonyms: 8-姜辣醇) 目录号 : GC60542
A natural TRPV1 agonist
Cas No.:23513-08-8
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
8-Gingerol is a natural chemical found in the rhizomes of ginger (Z. officinale). It contains the same aromatic region and polar link but has a longer hydrophobic tail than the more abundant 6-gingerol . Like 6-gingerol, 8-gingerol activates the transient receptor potential vanilloid receptor 1 (TRPV1; EC50 = 5.0 ?M), inhibits COX-2, and inhibits the growth of H. pylori in vitro.1,2 8-Gingerol also augments wound healing, suppresses IL-2-induced proliferation of T lymphocytes, and potentiates β-agonist-induced relaxation of airway smooth muscle.3,4,5 Oral 8-gingerol is expected to be readily absorbed and rapidly metabolized by glucuronidation and sulfation, with minimal to modest effects on cytochrome P450 isoforms.6,7
1.Dedov, V.N., Tran, V.H., Duke, C.C., et al.Gingerols: a novel class of vanilloid receptor (VR1) agonistsBr. J. Pharmacol.137(6)793-798(2002) 2.Chrubasik, S., Pittler, M.H., and Roufogalis, B.D.Zingiberis rhizoma: A comprehensive review on the ginger effect and efficacy profilesPhytomedicine12(9)684-701(2005) 3.Bakht, M.A., Alajmi, M.F., Alam, P., et al.Theoretical and experimental study on lipophilicity and wound healing activity of ginger compoundsAsian Pac. J. Trop. Biomed.4(4)329-333(2014) 4.Bernard, M., Furlong, S.J., Power Coombs, M.R., et al.Differential inhibition of T lymphocyte proliferation and cytokine synthesis by [6]-Gingerol, [8]-Gingerol, and [10]-GingerolPhytother. Res.29(11)1707-1713(2015) 5.Townsend, E.A., Zhang, Y., Xu, C., et al.Active components of ginger potentiate β-agonist-induced relaxation of airway smooth muscle by modulating cytoskeletal regulatory proteinsAm. J. Respir. Cell Mol. Biol.50(1)115-124(2014) 6.Mukkavilli, R., Gundala, S.R., Yang, C., et al.Modulation of cytochrome P450 metabolism and transport across intestinal epithelial barrier by ginger biophenolicsPLoS One9(9)e108386(2014) 7.Qiu, J.-X., Zhou, Z.-W., He, Z.-X., et al.Estimation of the binding modes with important human cytochrome P450 enzymes, drug interaction potential, pharmacokinetics, and hepatotoxicity of ginger components using molecular docking, computational, and pharmacokinetic modeling studiesDrug Des. Devel. Ther.9841-866(2015)
| Cas No. | 23513-08-8 | SDF | |
| 别名 | 8-姜辣醇 | ||
| Canonical SMILES | CCCCCCC[C@H](O)CC(CCC1=CC=C(O)C(OC)=C1)=O | ||
| 分子式 | C19H30O4 | 分子量 | 322.44 |
| 溶解度 | DMSO: ≥ 100 mg/mL (310.14 mM) | 储存条件 | Store at -20°C, sealed storage, away from moisture and 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 | 3.1014 mL | 15.5068 mL | 31.0135 mL |
| 5 mM | 0.6203 mL | 3.1014 mL | 6.2027 mL |
| 10 mM | 0.3101 mL | 1.5507 mL | 3.1014 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。
8-Gingerol Ameliorates Myocardial Fibrosis by Attenuating Reactive Oxygen Species, Apoptosis, and Autophagy via the PI3K/Akt/mTOR Signaling Pathway
Front Pharmacol 2021 Jul 28;12:711701.PMID:34393792DOI:10.3389/fphar.2021.711701.
8-Gingerol (8-Gin) is the series of phenolic substance that is extracted from ginger. Although many studies have revealed that 8-Gin has multiple pharmacological properties, the possible underlying mechanisms of 8-Gin against myocardial fibrosis (MF) remains unclear. The study examined the exact role and potential mechanisms of 8-Gin against isoproterenol (ISO)-induced MF. Male mice were intraperitoneally injected with 8-Gin (10 and 20 mg/kg/d) and concurrently subcutaneously injected with ISO (10 mg/kg/d) for 2 weeks. Electrocardiography, pathological heart morphology, myocardial enzymes, reactive oxygen species (ROS) generation, degree of apoptosis, and autophagy pathway-related proteins were measured. Our study observed 8-Gin significantly reduced J-point elevation and heart rate. Besides, 8-Gin caused a marked decrease in cardiac weight index and left ventricle weight index, serum levels of creatine kinase and lactate dehydrogenase (CK and LDH, respectively), ROS generation, and attenuated ISO-induced pathological heart damage. Moreover, treatment with 8-Gin resulted in a marked decrease in the levels of collagen types I and III and TGF-β in the heart tissue. Our results showed 8-Gin exposure significantly suppressed ISO-induced autophagosome formation. 8-Gin also could lead to down-regulation of the activities of matrix metalloproteinases-9 (MMP-9), Caspase-9, and Bax protein, up-regulation of the activity of Bcl-2 protein, and alleviation of cardiomyocyte apoptosis. Furthermore, 8-Gin produced an obvious increase in the expressions of the PI3K/Akt/mTOR signaling pathway-related proteins. Our data showed that 8-Gin exerted cardioprotective effects on ISO-induced MF, which possibly occurred in connection with inhibition of ROS generation, apoptosis, and autophagy via modulation of the PI3K/Akt/mTOR signaling pathway.
Ginger from Farmyard to Town: Nutritional and Pharmacological Applications
Front Pharmacol 2021 Nov 26;12:779352.PMID:34899343DOI:10.3389/fphar.2021.779352.
Ginger (Zingiber officinale) is one of the most widely used natural products consumed as a spice and medicine for treating diabetes, flatulent intestinal colic, indigestion, infertility, inflammation, insomnia, a memory booster, nausea, rheumatism, stomach ache, and urinary tract infections. To date, over 400 bioactive components, such as diarylheptanoids, gingerol analogues, phenylalkanoids, sulfonates, monoterpenoid glycosides, steroids, and terpene compounds have been derived from ginger. Increasing evidence has revealed that ginger possesses a broad range of biological activities, especially protective effects against male infertility, nausea and vomiting, analgesic, anti-diabetic, anti-inflammatory, anti-obesity, and other effects. The pharmacological activities of ginger were mainly attributed to its active phytoconstituents such as 6-gingerol, gingerdiol, gingerol, gingerdione, paradols, shogaols, sesquiterpenes, zingerone, besides other phenolics and flavonoids. In recent years, in silico molecular docking studies revealed that gingerol (6-gingerol, 8-Gingerol, and 10-gingerol) and Shogaol (6-shogaol, 8-shogaol, 10-shogaol) had the best binding affinities to the receptor protein in disease conditions such as diabetes, inflammation, obesity, and SARS-CoV-2. Furthermore, some clinical trials have indicated that ginger can be consumed for alleviation of nausea and vomiting induced by surgery, pain, diabetes, obesity, inflammation, male infertility. This review provides an updated understanding of the scientific evidence on the development of ginger and its active compounds as health beneficial agents in future clinical trials.
Therapeutic Effects of 6-Gingerol, 8-Gingerol, and 10-Gingerol on Dextran Sulfate Sodium-Induced Acute Ulcerative Colitis in Rats
Phytother Res 2017 Sep;31(9):1427-1432.PMID:28762585DOI:10.1002/ptr.5871.
Ulcerative colitis is one of the most common types of inflammatory bowel disease and is multifactorial and relapsing. 6-Gingerol, a component of gingerols extracted from ginger (Zingiber officinale), has been reported to improve ulcerative colitis. The present study aims to investigate the therapeutic efficacy of two analogous forms of 6-gingerol, 8-Gingerol, and 10-gingerol, on ulcerative colitis. Colitis was induced in rats through consumption of 5% (w/v) dextran sulfate sodium drinking water for 7 consecutive days. 6-Gingerol, 8-Gingerol, and 10-gingerol were then given intraperitoneally at doses of 30 mg kg-1 d-1 for another 7 days, respectively. Body weight change, disease activity index, inflammatory cytokines, and oxidative stress indices were measured, and the colonic tissue injuries were assessed macroscopically and histopathologically. Results showed that all three gingerols attenuated colitic symptoms evoked by dextran sulfate sodium, significantly elevated superoxide dismutase activity, decreased malondialdehyde levels and myeloperoxidase activity in the colon tissue, and markedly reduced the content of tumor necrosis factor alpha and Interleukin 1 beta in the serum. Histological observations showed that all three gingerols obviously accelerated mucosal damage healing. It is concluded that 6-gingerol, 8-Gingerol, and 10-gingerol, the three analogues, have a strong and relatively equal efficacy in the treatment of colitis. Copyright © 2017 John Wiley & Sons, Ltd.
Pharmacokinetics of 6-gingerol, 8-Gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects
Cancer Epidemiol Biomarkers Prev 2008 Aug;17(8):1930-6.PMID:18708382DOI:10.1158/1055-9965.EPI-07-2934.
Background: Ginger shows promising anticancer properties. No research has examined the pharmacokinetics of the ginger constituents 6-gingerol, 8-Gingerol, 10-gingerol, and 6-shogaol in humans. We conducted a clinical trial with 6-gingerol, 8-Gingerol, 10-gingerol, and 6-shogaol, examining the pharmacokinetics and tolerability of these analytes and their conjugate metabolites. Methods: Human volunteers were given ginger at doses from 100 mg to 2.0 g (N = 27), and blood samples were obtained at 15 minutes to 72 hours after a single p.o. dose. The participants were allocated in a dose-escalation manner starting with 100 mg. There was a total of three participants at each dose except for 1.0 g (N = 6) and 2.0 g (N = 9). Results: No participant had detectable free 6-gingerol, 8-Gingerol, 10-gingerol, or 6-shogaol, but 6-gingerol, 8-Gingerol, 10-gingerol, and 6-shogaol glucuronides were detected. The 6-gingerol sulfate conjugate was detected above the 1.0-g dose, but there were no detectable 10-gingerol or 6-shogaol sulfates except for one participant with detectable 8-Gingerol sulfate. The C(max) and area under the curve values (mean +/- SE) estimated for the 2.0-g dose are 0.85 +/- 0.43, 0.23 +/- 0.16, 0.53 +/- 0.40, and 0.15 +/- 0.12 microg/mL; and 65.6.33 +/- 44.4, 18.1 +/- 20.3, 50.1 +/- 49.3, and 10.9 +/- 13.0 microg x hr/mL for 6-gingerol, 8-Gingerol, 10-gingerol, and 6-shogaol. The corresponding t(max) values are 65.6 +/- 44.4, 73.1 +/- 29.4, 75.0 +/- 27.8, and 65.6 +/- 22.6 minutes, and the analytes had elimination half-lives <2 hours. The 8-Gingerol, 10-gingerol, and 6-shogaol conjugates were present as either glucuronide or sulfate conjugates, not as mixed conjugates, although 6-gingerol and 10-gingerol were an exception. Conclusion: Six-gingerol, 8-Gingerol, 10-gingerol, and 6-shogaol are absorbed after p.o. dosing and can be detected as glucuronide and sulfate conjugates.
High-performance liquid chromatographic analysis of 6-gingerol, 8-Gingerol, 10-gingerol, and 6-shogaol in ginger-containing dietary supplements, spices, teas, and beverages
J Chromatogr B Analyt Technol Biomed Life Sci 2007 Sep 1;856(1-2):41-7.PMID:17561453DOI:10.1016/j.jchromb.2007.05.011.
Ginger root powder is widely used as a dietary supplement as well as a spice and flavoring agent in foods and beverages. In this study, we developed a high-performance liquid chromatographic (HPLC) method that is suitable for the analysis of 6-gingerol, 6-shogaol, 8-Gingerol, and 10-gingerol in a wide variety of ginger-containing dietary supplements, spices, teas, mints, and beverages. 6-Gingerol, 6-shogaol, 8-Gingerol, and 10-gingerol were extracted from various ginger-containing products with ethyl acetate and analyzed by HPLC on a C-8 reversed phase column at 282 nm. The recoveries of 6-, 8-, and 10-gingerol, and 6-shogaol from the ginger dietary supplements and ginger-containing products were 94.7+/-4.1, 93.6+/-3.4, 94.9+/-4.0, 97.1+/-3.8%, respectively. The within-day coefficients of variation for 6-gingerol, 6-shogaol, 8-Gingerol, and 10-gingerol standards at 50.0 microg/mL were 2.54, 2.38, 2.55, and 2.31%, respectively. The lower limit of quantitation was 25 ng injected. The standard curves for 6-, 8-, and 10-gingerol and 6-shogaol were linear from 10.0 to 1000 microg/mL. The variation (CV's) in the 6-gingerol, 6-shogaol, 8-Gingerol, and 10-gingerol concentrations of nine different ginger root dietary supplements were 115.2, 45.7, 72.3, and 141.7%, respectively. The gingerol composition of various ginger-containing spices, teas, and beverages also were found to vary widely. The proposed method can be used for the analysis and standardization of 6-, 8-, and 10-gingerol in ginger-containing dietary supplements, spices, food products and beverages and as a method for determining the amounts of 6-shogaol as a marker for 6-gingerol stability.