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: 2024-01-07 22:13:37
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	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer
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	[1]. Won YS, et al. Lupiwighteone induces caspase-dependent and -independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway. Food Chem Toxicol. 2020 Jan;135:110863. [2]. Ren J, et al. Isoflavone lupiwighteone induces cytotoxic, apoptotic, and antiangiogenic activities in DU-145 prostate cancer cells. Anticancer Drugs. 2015 Jul;26(6):599-611.

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

104691-86-3	916917-28-7
22697-65-0	1246926-08-8
959421-20-6	143724-75-8
5240-95-9	90179-86-5
1446712-19-1	90179-85-4