104691-86-3
104691-86-3 structure
- Name: 5,7,4'-Trihydroxy-8-(3,3-dimethylallyl)isoflavone
- Chemical Name: Lupiwighteone
- CAS Number: 104691-86-3
- Molecular Formula: C20H18O5
- Molecular Weight: 338.354
- Catalog: Natural product Flavonoids
- Create Date: 2016-12-09 03:08:13
- Modify Date: 2025-08-27 10:24:22
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Lupiwighteone is an isoflavone present widely in wild-growing plants, with antioxidant, antimicrobial and anticancer effects. Lupiwighteone induces caspase-dependent and -independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway[1][2].
| Name | Lupiwighteone |
|---|---|
| Synonyms |
4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-
5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-chromen-4-one 5,7,4'-Trihydroxy-8-(3,3-dimethylallyl)isoflavone 5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one |
| Description | Lupiwighteone is an isoflavone present widely in wild-growing plants, with antioxidant, antimicrobial and anticancer effects. Lupiwighteone induces caspase-dependent and -independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway[1][2]. |
|---|---|
| Related Catalog | |
| Target |
apoptosis[2] |
| In Vitro | Lupiwighteone (2-100 μM; 72 hours) shows cytotoxicity towards various cell lines, especially on DU-145 cells and SGC-7901 cells with IC50s of 23.7 μM and 21 μM, respectively[2]. Lupiwighteone (20-60 μM; 48 hours) induces (cell cycle arrest in DU-145 cells[2]. Lupiwighteone (20-60 μM; 48 hours) induces cells apoptosis[2]. Lupiwighteone (20-60 μM; 48 hours) decreases the cell cycle-related protein expressions in a dose-dependent manner in DU-145 cells[2]. Lupiwighteone (20-60 μM; 48 hours) induces a dose-dependent increase in ROS production[2]. Lupiwighteone up-regulates of cytochrome c and caspase-3, and subsequent cleavage of PARP-1 and down-regulates of the p-Akt/Akt ratio and VEGF expression, suggests the activation of mitochondria-based intrinsic apoptosis in DU-145 cells[2]. Cell Viability Assay[2] Cell Line: DU-145 cells, C4-2 cells, SGC-7901 cells, Hela cells, HUVEC, MCF-7 cells, CNE cells, Vero Concentration: 2 μM, 5 μM, 25 μM, 50 μM, 100 μM Incubation Time: 72 hours Result: Had inhibition on the survival of many cancer cell lines and HUVEC. Cell Cycle Analysis[2] Cell Line: DU-145 cells Concentration: 20 μM, 40 μM, 60 μM Incubation Time: 48 hours Result: Induced cell cycle arrest. Apoptosis Analysis[2] Cell Line: DU-145 cells Concentration: 20 μM, 40 μM, 60 μM Incubation Time: 48 hours Result: Induced apoptosis. Western Blot Analysis[2] Cell Line: DU-145 cells Concentration: 20 μM, 40 μM, 60 μM Incubation Time: 48 hours Result: Decreased CDK1, 2, 4, 6, cyclinD1, and cyclinB1 protein expression in a dose-dependent manner. |
| References |
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 583.5±50.0 °C at 760 mmHg |
| Melting Point | 133-135℃ |
| Molecular Formula | C20H18O5 |
| Molecular Weight | 338.354 |
| Flash Point | 211.8±23.6 °C |
| Exact Mass | 338.115417 |
| PSA | 90.90000 |
| LogP | 5.05 |
| Vapour Pressure | 0.0±1.7 mmHg at 25°C |
| Index of Refraction | 1.667 |
| Hazard Codes | Xi |
|---|