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5,7,3',4'-Tetrahydroxy-6,8-diprenylisoflavone

Names

[ CAS No. ]:
66777-70-6

[ Name ]:
5,7,3',4'-Tetrahydroxy-6,8-diprenylisoflavone

[Synonym ]:
3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6,8-bis(3-methyl-2-buten-1-yl)-4H-chromen-4-one
4H-1-Benzopyran-4-one, 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis(3-methyl-2-buten-1-yl)-
5,7,3',4'-Tetrahydroxy-6,8-diprenylisoflavone

Biological Activity

[Description]:

6,8-Diprenylorobol, a prenylated isoflavone, is a nature product that could be isolated from the leaves of Cudrania tricuspidata. 6,8-Diprenylorobol antiproliferative effect and induces apoptosis through activation of p53 and generation of ROS[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Bcl-2 Family
Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Apoptosis >> Caspase
Signaling Pathways >> PI3K/Akt/mTOR >> Akt
Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK
Signaling Pathways >> MAPK/ERK Pathway >> ERK
Signaling Pathways >> MAPK/ERK Pathway >> JNK
Signaling Pathways >> Stem Cell/Wnt >> ERK

[In Vitro]

6,8-Diprenylorobol (20-60 μM; 24-72 h) 抑制 LoVo 和 HCT15 细胞增殖[1]。 6,8-Diprenylorobol (20-60 μM;24 h) 诱导 LoVo 和 HCT15 细胞凋亡,激活 p53 并调控 MAPKs[1]。 6,8-Diprenylorobol (20-60 μM; 1 h) 增加 LoVo 和 HCT15 细胞的 ROS 水平[1]。 Cell Viability Assay[1] Cell Line: LoVo and HCT15 cells Concentration: 20, 40, and 60 μM Incubation Time: 24, 48, and 72 hours Result: Inhibited the growth of LoVo and HCT15 cells in a dose- and dose-dependent manner. Apoptosis Analysis[1] Cell Line: LoVo and HCT15 cells Concentration: 20, 40, and 60 μM Incubation Time: 24 hours Result: Induced apoptosis of LoVo and HCT15 cells in a dose- and time-dependent manner. Western Blot Analysis[1] Cell Line: LoVo and HCT15 cells Concentration: 20, 40, and 60 μM Incubation Time: 24, 48, and 72 hours Result: Decreased the expression of PARP and increased the expression of cleaved PARP. Up-regulated Bax and Bim expressions and downregulated Bcl-2 expression. Up-regulated cleaved caspase-3, -7, -8, and -9 expressions, and down-regulated procaspase-3, -7, -8, and -9 expressions. Decreased the expression of phosphorylated Akt, ERK, JNK, and p38 and increased the expression of FOXO3, p53, p27, and p21.

[References]

[1]. Choi YJ, et, al. 6,8-Diprenylorobol induces apoptosis in human colon cancer cells via activation of intracellular reactive oxygen species and p53. Environ Toxicol. 2021 May;36(5):914-925.  

[2]. Tuan Anh HL, et, al. Prenylated isoflavones from Cudrania tricuspidata inhibit NO production in RAW 264.7 macrophages and suppress HL-60 cells proliferation. J Asian Nat Prod Res. 2017 May;19(5):510-518.  

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
667.1±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C25H26O6

[ Molecular Weight ]:
422.470

[ Flash Point ]:
228.6±25.0 °C

[ Exact Mass ]:
422.172943

[ PSA ]:
111.13000

[ LogP ]:
6.94

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.650

Precursor & DownStream

Precursor

DownStream


Related Compounds

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