Scutellarin
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IUPAC name
4′,5,6-Trihydroxy-4-oxoflav-2-en-7-yl β-D-glucopyranosiduronic acid
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Systematic IUPAC name
(2S,3S,4S,5R,6S)-6-{[5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid | |
Other names
Breviscapine; Breviscapin; Scutellarein-7-glucuronide; Scutellarein-7beta-D-glucuronide; Scutellarein-7beta-D-glucuronoside; Scutellarein-7-O-beta-D-glucuronide; 7-(β-D-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C21H18O12 | |
Molar mass | 462.36 g/mol |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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1314 mg/kg (mouse, intravenous) [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Scutellarin is a flavone, a type of phenolic chemical compound. It can be found in the Asian "barbed skullcap" Scutellaria barbata and the north American plant S. lateriflora both of which have been used in traditional medicine. The compound is found only in trace amounts in the "Chinese skullcap" Scutellaria baicalensis, another plant used in traditional Chinese medicine.
The determination of the structure of scutellarin took Guido Goldschmiedt many years: after the first publication on that topic in 1901, only in 1910 he managed to obtain enough starting material for more detailed studies.
Scutellarin has anticancer properties. It has been found to induce
Scutellarin also shows protective effects for nerve cells that are affected by estrogen.[3]
Scutellarin has been shown as a potential treatment for diabetic retinopathy, which could prevent diabetic blindness. In laboratory studies, scutellarin inhibits hypoxia-induced and moderately high glucose-induced proliferation and vascular endothelial growth factor (VEGF) expression in human retinal endothelial cells; thus, it could be a potential therapy for diabetic retinopathy. However, how scutellarin inhibits VEGF is unknown.[4]
Scutellarin has anti-