(E)-[8]-Shogaol
(E)-[8]-Shogaol is an isomer of [8]-Shogaol (HY-N2435). [8]-Shogaol is an orally active apoptosis inducer and growth inhibitor. [8]-Shogaol induces apoptosis by promoting the expression of the pro-apoptotic protein Bad, antagonizing members of the Bcl-2 family, and activating the caspase cascade. [8]-Shogaol also induces autophagy and endoplasmic reticulum stress by generating reactive oxygen species, depleting glutathione, and disrupting mitochondrial transmembrane potential. In addition, [8]-Shogaol inhibits LPS-mediated production of inflammatory cytokines and sensitizes radioresistant gastric cancer cells to radiotherapy. [8]-Shogaol is widely used in studies related to leukemia, colorectal cancer, gastric cancer, as well as LPS-induced sepsis or inflammation.
For research use only. We do not sell to patients.
- CAS No.: 104186-07-4
- Formula: C19H28O3
- Molecular Weight:304.42
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
![(E)-[8]-Shogaol Chemical Structure](https://file.medchemexpress.com/product_pic/hy-n2435a.gif "Click to View (E)-[8]-Shogaol Chemical Structure")
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Biological Activity
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Chemical Information
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Biological Activity
Description
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| IMR-32 | ED50 |
8.8 μM
Compound: 10
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Effective dose to protect IMR-32 cells from beta-Amyloid (BA) insult was determined using MTT reduction assay
Effective dose to protect IMR-32 cells from beta-Amyloid (BA) insult was determined using MTT reduction assay
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[PMID: 14980683] |
In Vitro
[8]-Shogaol (10-50 μM; 24 h) potently reduces human promyelocytic leukemia HL-60 cell viability in a concentration-dependent manner[1].
[8]-Shogaol (10-50 μM; 24 h, 30 μM; 1-12 h) induces apoptosis in human promyelocytic leukemia HL-60 cells in both concentration- and time-dependent manners[1].
[8]-Shogaol (30 μM; 1-12 h) activates caspase-3, -8, and -9 (but not caspase-1) and triggers cleavage of PARP, DFF-45, and D4-GDI in a time-dependent manner in human promyelocytic leukemia HL-60 cells[1].
[8]-Shogaol (15-25 μM; 24 h) induces concentration-dependent G2/M phase cell cycle arrest in human colon cancer HCT116 cells, with 58.10% of cells in G2/M phase at 25 μM, and modulates cell cycle-related protein expression[2].
[8]-Shogaol (15-25 μM; 24 h) dose-dependently inhibits the PI3K/AKT signaling pathway in human colon cancer HCT116 cells by reducing p-AKT and p-PI3K levels, and attenuates SC79-induced AKT phosphorylation[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:human promyelocytic leukemia HL-60 cells
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Concentration:10, 20, 30, 40, 50 μM
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Incubation Time:24 h
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Result:Reduced HL-60 cell viability in a concentration-dependent manner.
Decreased cell viability to ~60% at 10 μM, ~45% at 20 μM, ~5% at 30 μM, and near 0% at 40 and 50 μM.
Showed statistically significant differences from control at all concentrations (P < 0.001).
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Cell Line:human promyelocytic leukemia HL-60 cells
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Concentration:10, 20, 30, 40, 50 μM (24 h incubation); 30 μM (1, 3, 6, 9, 12 h incubation)
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Incubation Time:24 h (10, 20, 30, 40, 50 μM); 1, 3, 6, 9, 12 h (30 μM)
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Result:Increased percentage of apoptotic HL-60 cells (sub-G1 population) to 11.70% at 10 μM, 25.97% at 20 μM, 35.68% at 30 μM, 41.43% at 40 μM, and 43.67% at 50 μM after 24 h treatment.
Increased sub-G1 population to 6.19% at 1 h, 10.42% at 3 h, 31.43% at 6 h, 28.06% at 9 h, and 25.64% at 12 h with 30 μM treatment over time.
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Cell Line:human colon cancer HCT116 cells, normal human HEK293 cells
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Concentration:5-40 μM (MTT assay); 15-25 μM (morphological analysis)
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Incubation Time:24 h (MTT assay); null (morphological analysis)
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Result:Exhibited a concentration-dependent inhibitory effect on HCT116 cells, with an IC50 value of 20.03 μM.
Showed minimal toxicity towards normal HEK293 cells.
Reduced HCT116 cell number and induced rounded, vacuolated morphology with increasing concentration.
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Cell Line:human colon cancer HCT116 cells
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Concentration:15-25 μM (single treatment); 20 μM (co-treatment with SC79)
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Incubation Time:24 h
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Result:Reduced p-AKT and p-PI3K expression in a concentration-dependent manner, while total AKT and PI3K expression remained relatively stable.
Attenuated SC79-induced p-AKT expression when co-treated with SC79.
In Vivo
[8]-Shogaol (30 mg/kg; i.p.; twice weekly) increases survival by approximately fourfold and reduces levels of pro-inflammatory cytokines (TNF-α, IL-6, IL-1β) in a murine LPS-induced sepsis model[3].
[8]-Shogaol (30-60 mg/kg; i.p.; twice weekly) significantly inhibits AGS gastric cancer tumor growth in nude mice without causing body weight loss[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Balb/c female nude mice (5 weeks old)[2]
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Dosage:20 mg/kg; 40 mg/kg
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Administration:p.o.; daily; 14 days
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Result:Reduced mean tumor volume to 0.585 cm3 and mean tumor weight to 0.942 g at 20 mg/kg.
Reduced mean tumor volume to 0.317 cm3 and mean tumor weight to 0.548 g at 40 mg/kg.
Induced reduced cell density, apoptotic cells, and necrotic regions in tumor tissue via H&E staining.
Increased apoptosis in a concentration-dependent pattern confirmed by TUNEL staining.
Reduced P-AKT expression and increased Beclin-1 expression in tumor tissue at 40 mg/kg.
- RNA extraction experimental
- Detection of Apoptosis
- TUNEL staining for apoptotic DNA fragmentation
- LPS-Induced Endotoxemia/Systemic Inflammation
- Annexin V plus membrane-impermeant dye apoptosis staining
- ROS/oxidative-stress fluorescent staining
- Autophagy
- Apoptosis Solutions
- Lysosome and acidic-vesicle live-cell staining
- Research Protocol for Inflammation-related Diseases
- Macroautophagy Solutions
Chemical Information
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CAS No. 104186-07-4
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Molecular Weight 304.42
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Formula C19H28O3
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SMILES
CCCCCCC/C=C/C(CCC1=CC(OC)=C(C=C1)O)=O
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Shieh PC, et al. Induction of apoptosis by [8]-shogaol via reactive oxygen species generation, glutathione depletion, and caspase activation in human leukemia cells. J Agric Food Chem. 2010;58(6):3847-3854. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
(E)-[8]-Shogaol Related Classifications
HY-N2435A Related Classifications
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