| Size | Price | Stock | Qty |
|---|---|---|---|
| 25mg |
|
||
| 50mg |
|
||
| 100mg |
|
||
| 250mg |
|
Shogaol (6-Shogaol) is a novel and potent pungent constituent of ginger that is able to reduce blood pressure and gastric contraction
| Targets |
6-Shogaol activates the Nuclear factor E2-related factor 2 (Nrf2)/Antioxidant Response Element (ARE) pathway, leading to upregulation of heme oxygenase-1 (HO-1) and other antioxidant enzymes.
The activation is mediated through phosphorylation of p38 mitogen-activated protein kinase (MAPK) and the PI3K/Akt pathway. |
|---|---|
| ln Vitro |
Anticancer activity of shogaol ([6]-Shogaol) has been observed against multiple cell lines [1]. Shogaol ([6]-Shogaol) is thought to be cytotoxic in a variety of cell lines, with the most sensitive cells to 6-shogaol being KB (IC50=7.4±2.2 μM) and HL60 (IC50=7.9±2.0 μM)[2]. Compared to 6-gingerol (IC50=150 μM), 6-gingerol (IC50=8 μM) had a significantly greater growth-inhibiting impact on HCT-116 human colon cancer cells [3]. The phosphorylation of mitogen-activated protein kinases (MAPKs), including ERK, JNK, and p38, is stimulated by shogaol ([6]-Shogaol). Additionally, treatment with LY294002 (an Akt-specific inhibitor) and SB202190 (a p38-specific inhibitor) reduced the expression of Nrf2 and HO-1 generated by 6-shogaol [4].
A 6-Shogaol-rich ginger extract (GEE8080) was produced by extracting dried ginger powder with 95% ethanol at 80°C, resulting in a 6-fold higher 6-Shogaol content (21 mg/g dry matter) compared to room temperature extraction (GEE80RT, 3.5 mg/g dry matter). In HepG2-C8 cells stably transfected with an ARE-luciferase reporter gene, GEE8080 (50 μg/mL) treatment for 12 hours potently induced ARE-luciferase activity, with induction similar to the positive control sulforaphane (SFN). In HepG2 cells, GEE8080 (50 μg/mL) treatment for 2 hours strongly induced Nrf2 protein expression, and treatment for 24 hours upregulated HO-1 protein expression. GEE8080 (50 μg/mL) treatment for 1 hour stimulated phosphorylation of MAPKs (ERK, JNK, and p38) but did not affect Akt phosphorylation. Pretreatment with the p38 inhibitor SB202190 or the PI3K/Akt inhibitor LY294002 completely blocked GEE8080-induced upregulation of Nrf2 and HO-1 expression in HepG2 cells. GEE8080 treatment did not inhibit HepG2 cell viability at concentrations up to 50 μg/mL after 24 hours. |
| ln Vivo |
The administration of Shogaol ([6]-Shogaol to mice also restored DEN-reduced activity and protein expression of hepatic antioxidant enzymes such as superoxide dismutase, glutathione peroxidase, and catalase [ 4]. The induction of Nrf2 and HO-1 by 6-shogaol was also confirmed in mice. Diethylnitrosamine (DEN)-mediated elevation of serum aspartate aminotransferase and alanine aminotransferase as well as DEN-induced hepatic lipid peroxidation are reduced by Shogaol ([6]-Shogaol).
In a diethylnitrosamine (DEN)-induced liver injury mouse model, oral administration of the 6-Shogaol-rich extract (GEE8080) at doses of 10 and 100 mg/kg body weight (b.w.), three times per week for one week prior to and concurrent with DEN challenge (30 mg/kg b.w., i.p., three times per week for three weeks), significantly attenuated DEN-mediated elevations in serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) levels. GEE8080 administration (10 and 100 mg/kg b.w.) also completely inhibited DEN-induced hepatic lipid peroxidation, as measured by thiobarbituric acid reactive substances (TBARS). In liver tissues of DEN-treated mice, GEE8080 administration restored the DEN-attenuated protein expression of Nrf2 and HO-1. GEE8080 administration (10 and 100 mg/kg b.w.) significantly restored the DEN-reduced activity and protein expression of hepatic antioxidant enzymes, including superoxide dismutase (SOD), glutathione peroxidase (GPx), and catalase (CAT). The lower dose (10 mg/kg) of GEE8080 showed slightly greater induction of SOD and GPx enzyme activity and was more effective in restoring protein expression levels of these enzymes compared to the higher dose (100 mg/kg). |
| Cell Assay |
Cell viability was assessed using the MTT assay. HepG2 cells were seeded in 24-well plates, starved overnight in serum-free medium, and then treated with compounds. After treatment, MTT solution (5 mg/mL) was added and incubated for 4 hours. The formazan crystals were dissolved, and absorbance was measured at 570 nm.
ARE-reporter gene activity was measured using HepG2-C8 cells stably transfected with the pARE-T1-luciferase reporter gene. After treatment, cells were lysed, and luciferase activity was measured using a luciferase assay system and normalized to protein content. For protein expression analysis (Western blot), treated HepG2 cells or homogenized mouse liver tissues were lysed. Proteins were separated by SDS-PAGE, transferred to membranes, blocked, and incubated with primary antibodies (e.g., anti-Nrf2, anti-HO-1, anti-phospho-ERK, etc.) overnight. After incubation with HRP-conjugated secondary antibodies, protein bands were visualized using enhanced chemiluminescence reagents. |
| Animal Protocol |
Male Balb/c mice (6 weeks old) were divided into five groups (n=5 per group).
The normal control group received the vehicle (polyethylene glycol oil, PEG) orally for one week. The DEN group received PEG for one week and then was injected intraperitoneally (i.p.) with DEN (30 mg/kg b.w.) dissolved in saline, three times per week for three weeks. Two GEE8080 treatment groups were administered GEE8080 extract orally at doses of 10 or 100 mg/kg b.w., three times per week for one week, followed by co-administration with DEN (i.p., 30 mg/kg b.w., three times per week) for three weeks. The positive control group received silymarin orally at 100 mg/kg b.w. on the same schedule as the GEE8080 groups, followed by DEN challenge. At the end of the treatment period, serum and liver tissues were collected for analysis. |
| ADME/Pharmacokinetics |
The study indicates that both 6-Shogaol and 6-shogaol are extensively metabolized under cell culture conditions. The authors state that they are currently working on the purification and identification of the major metabolites. [3]
|
| References |
|
| Additional Infomation |
[6]-Shogaol is a monomethoxybenzene belonging to the phenol and enone classes. It has been reported in dwarf plants (Flueggea suffruticosa), European fir (Abies holophylla), and other organisms with relevant data. See also: Ginger (partial). 6-Shogaol is a dehydrated product of 6-Shogaol and can be enriched in ginger extracts via high-temperature extraction. The bioactivity (antioxidant defense, hepatoprotective effects) observed in this study was attributed to ginger extract (GEE8080) rich in 6-Shogaol, indicating that 6-Shogaol is the key active ingredient. This study proposes that 6-Shogaol exerts its effects by activating the p38 MAPK and Nrf2/ARE pathways. The PI3K/Akt signaling pathway upregulates the expression of antioxidant enzymes such as HO-1, SOD, GPx, and CAT. This is the first report to demonstrate that ginger extract rich in 6-Shogaol exerts hepatoprotective and antioxidant defense effects in cells and mice through the Nrf2/ARE pathway.
|
| Molecular Formula |
C17H24O3
|
|---|---|
| Molecular Weight |
276.376
|
| Exact Mass |
276.172
|
| CAS # |
555-66-8
|
| PubChem CID |
5281794
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
1.0±0.1 g/cm3
|
| Boiling Point |
427.5±35.0 °C at 760 mmHg
|
| Flash Point |
150.3±19.4 °C
|
| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.522
|
| LogP |
3.85
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
9
|
| Heavy Atom Count |
20
|
| Complexity |
299
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O(C([H])([H])[H])C1=C(C([H])=C([H])C(=C1[H])C([H])([H])C([H])([H])C(/C(/[H])=C(\[H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O)O[H]
|
| InChi Key |
OQWKEEOHDMUXEO-BQYQJAHWSA-N
|
| InChi Code |
InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
|
| Chemical Name |
(E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one
|
| Synonyms |
Shogaol 6-Shogaol
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ≥ 50 mg/mL (~180.92 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.05 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 25.0 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 (9.05 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 (9.05 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 | 3.6182 mL | 18.0910 mL | 36.1821 mL | |
| 5 mM | 0.7236 mL | 3.6182 mL | 7.2364 mL | |
| 10 mM | 0.3618 mL | 1.8091 mL | 3.6182 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT03698318 | COMPLETED | Dietary Supplement: Tested product n°1 Dietary Supplement: Tested product n°2 Dietary Supplement: Tested product n°3 |
Healthy Subject | Givaudan France Naturals | 2018-10-15 | Not Applicable |
| NCT03894137 | UNKNOWN STATUS | Dietary Supplement: Grains of Paradise | Obesity | Plexus Worldwide | 2019-10 | Not Applicable |
|
|
|
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
