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90-18-6

90-18-6 structure
90-18-6 structure
  • Name: 3,3',4',5,6,7-HEXAHYDROXYFLAVONE
  • Chemical Name: quercetagetin
  • CAS Number: 90-18-6
  • Molecular Formula: C15H10O8
  • Molecular Weight: 318.23500
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-04-16 08:00:00
  • Modify Date: 2024-01-09 22:26:51
  • Quercetagetin (6-Hydroxyquercetin) is the major flavonoid isolated from Citrus unshiu (C. unshiu) peel[3]. Quercetagetin is a moderately potent and selective, cell-permeable pim-1 kinase inhibitor (IC50, 0.34 μM)[1]. Anti-inflammatory and anticancer properties.

Name quercetagetin
Synonyms 3,5,6,7,3',4'-hexahydroxyflavonol
2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydroxychromen-4-one
6-Hydroxyquercetin
3,3',4',5,6,7-hexahydroxyflavone
3,5,6,7,3',4'-hexahydroxyflavone
Quercetagetin
Description Quercetagetin (6-Hydroxyquercetin) is the major flavonoid isolated from Citrus unshiu (C. unshiu) peel[3]. Quercetagetin is a moderately potent and selective, cell-permeable pim-1 kinase inhibitor (IC50, 0.34 μM)[1]. Anti-inflammatory and anticancer properties.
Related Catalog
Target

PIM1:0.34 μM (IC50)

PIM2:3.45 μM (IC50)

RSK2:2.82 μM (IC50)

PKA:21.2 μM (IC50)

In Vitro Quercetagetin also inhibits PIM2, PKA, and RSK2 with IC50s of 3.45, 21.2, and 2.82 µM, respectively. Quercetagetin inhibits PIM1 activity in intact RWPE2 prostate cancer cells in a dose-dependent manner (ED50, 5.5 μM). Furthermore Quercetagetin inhibits the activity of the Aurora-A kinase (IC50, ~4 μM). When pim-1-expressing cells were treated with Quercetagetin, p-BAD(S112) levels were markedly reduced in proportion to the concentration of Quercetagetin. Half-maximal inhibition occurred at 5.5 μM extracellular concentration[1]. Quercetagetin shows strong 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical-scavenging activity (IC50 7.89 μM) but much lower hydroxyl radical-scavenging activity (IC50 203.82 μM). Furthermore, Quercetagetin significantly reduces ROS in Vero cells and shows a strong protective effect against hydrogen peroxide-induced DNA damage[3].
In Vivo Quercetagetin significantly inhibits UVB-induced skin cancer development. Topical application of 4 or 20 nmol of Quercetagetin to mouse skin reduces tumor incidence by 32.0% and 46.7%, respectively[2].
Cell Assay RWPE2 cells are treated with Quercetagetin (0-12.5 μM) for up to 72 h. Cell number is measured by crystal violet staining and read at 570 nm[1].
Animal Admin Mice[2] UVB-induced skin tumorigenesis SKH-1 hairless mouse model are treated with topical application of 4 or 20 nmol of Quercetagetin. At the end of the study, the dimensions of each tumor in each mouse are recorded. Tumor volume is calculated[2].
References

[1]. Holder S, et al. Characterization of a potent and selective small-molecule inhibitor of the PIM1 kinase. Mol Cancer Ther. 2007 Jan;6(1):163-72.

[2]. Baek S, et al. Structural and functional analysis of the natural JNK1 inhibitor quercetagetin. J Mol Biol. 2013 Jan 23;425(2):411-23.

[3]. Yang X, et al. Isolation and identification of an antioxidant flavonoid compound from citrus-processing by-product. J Sci Food Agric. 2011 Aug 15;91(10):1925-7.

Density 1.912 g/cm3
Boiling Point 732.4ºC at 760 mmHg
Melting Point >300ºC
Molecular Formula C15H10O8
Molecular Weight 318.23500
Flash Point 280.3ºC
Exact Mass 318.03800
PSA 151.59000
LogP 1.69360
Index of Refraction 1.863
Storage condition 2-8℃