![[8]-Shogaol](/upload/1124/V30733.png)
| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 100mg | |||
| Other Sizes |
| Targets |
- Cyclooxygenase-2 (COX-2): Inhibited by [8]-Shogaol with an IC₅₀ value of 3.5 μM [1]
- Cyclooxygenase-1 (COX-1): Inhibited by [8]-Shogaol with a Ki value of 2.1 μM [2] - Human leukemia cells (HL-60, U937): Induced apoptosis via targeting reactive oxygen species (ROS) generation and caspase activation; [8]-Shogaol showed antiproliferative activity with IC₅₀ values of 8.2 μM (HL-60 cells) and 10.5 μM (U937 cells) [3] |
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| ln Vitro |
1. COX-2 inhibitory activity:
- [8]-Shogaol dose-dependently inhibited COX-2 enzyme activity in vitro, with maximum inhibition (92%) at 20 μM; IC₅₀ was determined as 3.5 μM [1] - The inhibition was selective for COX-2 over COX-1 (selectivity index = COX-1 IC₅₀ / COX-2 IC₅₀ = 5.7) [1] 2. COX-1 inhibitory and anti-platelet activity: - [8]-Shogaol competitively inhibited COX-1 activity with a Ki of 2.1 μM, reducing thromboxane A₂ (TXA₂) production in human platelets [2] - At 10 μM, [8]-Shogaol inhibited collagen-induced platelet aggregation by 78%, and arachidonic acid-induced aggregation by 85% [2] 3. Antiproliferative and pro-apoptotic activity in leukemia cells: - [8]-Shogaol suppressed proliferation of HL-60 (human promyelocytic leukemia) and U937 (human monocytic leukemia) cells in a time- and dose-dependent manner; IC₅₀ values were 8.2 μM (HL-60, 48 h) and 10.5 μM (U937, 48 h) [3] - Induced apoptosis in HL-60 cells: After 24 h treatment with 15 μM [8]-Shogaol, apoptotic rate (Annexin V-positive cells) increased from 3.2% (control) to 68.5% [3] - Triggered ROS generation: 10 μM [8]-Shogaol increased intracellular ROS levels by 3.2-fold (DCFH-DA assay) at 12 h [3] - Depleted glutathione (GSH): 15 μM [8]-Shogaol reduced intracellular GSH content by 62% at 24 h compared to control [3] - Activated caspases: Western blot showed cleaved caspase-3, -8, and -9 levels increased significantly after 18 h treatment with 10 μM [8]-Shogaol [3] |
| Enzyme Assay |
1. COX-2 enzyme activity assay:
- Reaction system contained COX-2 enzyme, arachidonic acid (substrate), and different concentrations of [8]-Shogaol (0.1-20 μM) [1] - Incubated at 37°C for 15 min; reaction was stopped by adding 1 M HCl [1] - Prostaglandin E₂ (PGE₂) (product of COX-2) was measured via enzyme-linked immunosorbent assay (ELISA); COX-2 activity was calculated based on PGE₂ levels, and IC₅₀ was derived from dose-response curves [1] 2. COX-1 enzyme activity assay: - Purified COX-1 enzyme was mixed with arachidonic acid and [8]-Shogaol (0.1-50 μM) in reaction buffer [2] - Incubated at 37°C for 20 min; TXA₂ (product of COX-1 in platelets) was converted to TXB₂ by adding SnCl₂ [2] - TXB₂ levels were quantified via radioimmunoassay (RIA); Ki value was calculated using Lineweaver-Burk plots [2] 3. Platelet aggregation assay: - Human platelets were isolated from fresh blood (centrifugation at 150×g for 10 min, then 1000×g for 15 min) and resuspended in Tyrode’s buffer [2] - Platelet suspension (200 μl) was preincubated with [8]-Shogaol (1-50 μM) for 5 min at 37°C [2] - Aggregation was induced by adding collagen (5 μg/ml) or arachidonic acid (100 μM); aggregation rate was measured using a platelet aggregometer for 5 min [2] |
| Cell Assay |
1. Leukemia cell culture and proliferation assay:
- HL-60 and U937 cells were cultured in RPMI-1640 medium supplemented with 10% fetal calf serum (FCS) and antibiotics, maintained at 37°C in 5% CO₂ [3] - Cells (5×10⁴ cells/well) were seeded in 96-well plates and treated with [8]-Shogaol (0-30 μM) for 24-72 h [3] - MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) solution (5 mg/ml) was added (20 μl/well) and incubated for 4 h [3] - Formazan crystals were dissolved in DMSO; absorbance was measured at 570 nm, and cell viability was calculated relative to control (untreated cells) [3] 2. Apoptosis detection (Annexin V/PI staining): - HL-60 cells (1×10⁶ cells/ml) were treated with [8]-Shogaol (0-20 μM) for 24 h [3] - Cells were harvested, washed with PBS, and stained with Annexin V-FITC and propidium iodide (PI) according to standard protocol [3] - Stained cells were analyzed by flow cytometry; apoptotic cells were defined as Annexin V-positive/PI-negative (early apoptosis) or Annexin V-positive/PI-positive (late apoptosis) [3] 3. ROS and GSH measurement: - ROS detection: HL-60 cells (1×10⁶ cells/ml) were loaded with DCFH-DA (10 μM) for 30 min, then treated with [8]-Shogaol (10 μM) [3] - Fluorescence intensity (ex: 488 nm, em: 525 nm) was measured at 0-24 h via flow cytometry to assess ROS levels [3] - GSH detection: Cells were lysed with 5% trichloroacetic acid; lysates were mixed with 5,5’-dithiobis-(2-nitrobenzoic acid) (DTNB) reagent [3] - Absorbance at 412 nm was measured, and GSH content was calculated using a standard curve [3] 4. Western blot for caspase activation: - HL-60 cells were treated with [8]-Shogaol (0-15 μM) for 18 h, then lysed in RIPA buffer [3] - Protein samples (30 μg/lane) were separated by SDS-PAGE and transferred to PVDF membranes [3] - Membranes were incubated with primary antibodies against caspase-3, -8, -9 (pro and cleaved forms) and β-actin (loading control), followed by secondary antibody [3] - Bands were visualized using enhanced chemiluminescence (ECL) reagent, and densitometry was performed to quantify cleaved caspase levels [3] |
| Toxicity/Toxicokinetics |
Cytotoxicity to normal cells: [8]-gingerol showed low cytotoxicity to human peripheral blood mononuclear cells (PBMCs); at a concentration of 20 μM, the cell viability of PBMCs was 82% (compared to 28% for HL-60 cells)[3]
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| References | |
| Additional Infomation |
[8]-Gingerol is a monomethoxybenzene, belonging to the enone class and also a phenolic compound.
It has been reported that ginger (Zingiber officinale) contains [8]-gingerol, and there is relevant data. See also: Ginger (partial). 1. Chemical background: [8]-gingerol is the pungent component of ginger (Zingiber officinale), which is derived from the dehydration reaction of [8]-gingerol during ginger processing (drying or heating) [1][2][3]. 2. COX inhibition mechanism: [8]-gingerol inhibits COX enzymes by competing with arachidonic acid (substrate) for the active site of COX-1/2 [1][2]. 3. Leukemia cell apoptosis mechanism: [8]-gingerol induces apoptosis through the endogenous (mitochondrial) pathway. ROS generation → GSH depletion → loss of mitochondrial membrane potential → caspase-9 activation → caspase-3 activation → apoptosis [3] |
| Molecular Formula |
C19H28O3
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|---|---|
| Molecular Weight |
304.4238
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| Exact Mass |
304.203
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| CAS # |
36700-45-5
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| PubChem CID |
6442560
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
452.3±35.0 °C at 760 mmHg
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| Flash Point |
154.6±19.4 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.516
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| LogP |
4.91
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
22
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| Complexity |
325
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(/C(/[H])=C(\[H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C1C([H])=C([H])C(=C(C=1[H])OC([H])([H])[H])O[H]
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| InChi Key |
LGZSMXJRMTYABD-MDZDMXLPSA-N
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| InChi Code |
InChI=1S/C19H28O3/c1-3-4-5-6-7-8-9-10-17(20)13-11-16-12-14-18(21)19(15-16)22-2/h9-10,12,14-15,21H,3-8,11,13H2,1-2H3/b10-9+
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| Chemical Name |
(E)-1-(4-hydroxy-3-methoxyphenyl)dodec-4-en-3-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~328.49 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 6.25 mg/mL (20.53 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (8.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2849 mL | 16.4247 mL | 32.8494 mL | |
| 5 mM | 0.6570 mL | 3.2849 mL | 6.5699 mL | |
| 10 mM | 0.3285 mL | 1.6425 mL | 3.2849 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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