Scutellarin
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Scutellarin
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CAS No:
27740-01-8
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Formula:
C21H18O12
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Chemical Name:
Scutellarin
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Synonyms:
β-D-Glucopyranosiduronic acid,5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl;Glucopyranosiduronic acid,5,6-dihydroxy-2-(p-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl,β-D-;Scutellarin;Flavone,4′,5,6,7-tetrahydroxy-,7-β-D-glucopyranuronoside;5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl β-D-glucopyranosiduronic acid;Scutellarein 7-β-D-glucuronoside;Scutellarein 7-glucuronide;Scutellarein 7-β-D-glucuronide;Scutellarein 7-O-β-D-glucuronide;Scutellarin B;Scutellarein 7-O-β-glucuronide;1329-06-2;32647-60-2;676536-34-8;1692861-25-8
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CAS No:
Description
Scutellarin, an active flavone isolated from Scutellaria baicalensis, can down-regulates the STAT3/Girdin/Akt signaling in HCC cells, and inhibits RANKL-mediated MAPK and NF-κB signaling pathway in osteoclasts.
Scutellarin is the glycosyloxyflavone which is the 7-O-glucuronide of scutellarein. It has a role as an antineoplastic agent and a proteasome inhibitor. It is a glycosyloxyflavone, a glucosiduronic acid, a trihydroxyflavone and a monosaccharide derivative. It derives from a scutellarein. It is a conjugate acid of a scutellarin(1-).
Drug Information
beta-D-glucopyranosiduronic acid, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl
Scutellarin Use and Manufacturing
A mixed solution of 300 mL water and 300 mL acetone was added to 20 g (42 mmol) of compound IV, and 70 mL of 10percent aqueous sodium hydroxide was added dropwise under stirring at 0 °C. The reaction was stirred continuously under protection of nitrogen gas at 0 °C for about two hours, which was completed as detected by HPLC. 10percent aqueous hydrochloric acid was added dropwise under stirring, to adjust pH to 2.0∼3.0, and stirred continuously for 1 hour followed by gradually raising to room temperature, with large amount of yellow solid 5, 6, 4'-trihydroxyflavone-7-O-D-glucuronic acid gradually separated out. The reaction mixture was left standing overnight at room temperature, filtered by suction, and the filter cake was washed with suitable amount of water and acetone, dried and then recrystallized with ethanol to obtain 17.3 g of pure 5, 6, 4'-trihydroxyflavone-7-O-D-glucuronic acid, with a yield of 89percent. The purity was 98.74percent detected by HPLC, the chromatogram detected by HPLC was shown in Figure 1, and the statistical result was shown in table 1. 1H-NMR (400MHz, DMSO), δ (ppm): 10.41 (1H, s), 8.63 (1H, s), 7.94 (2H, d, J= 8.8Hz), 6.99 (1H, s), 6.94 (2H, d, J= 8.8Hz), 6.86 (1H, s), 5.51-5.31 (3H, br), 5.28 (1H, d, J= 7.5 Hz), 4.11 (2H, d, J=9.6Hz), 3.43 (4H, m).
Scutellarin is an active flavonoid component from the medical plant Erigeron breviscapus (Vant) Hand-Mazz. Scutellarin is used as a micrpcirculation promoter for the treatment of cardio-cerebrovascular diseases. Studies suggest that Scutellarin has anti-cancer properties and has been shown to enhance apoptosis of tumor cells.
Computed Properties
Molecular Weight:462.4
XLogP3:0.8
Hydrogen Bond Donor Count:7
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:4
Exact Mass:462.07982601
Monoisotopic Mass:462.07982601
Topological Polar Surface Area:203
Heavy Atom Count:33
Complexity:777
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Dilate microvessels, improve microcirculation, enhance myocardial function and blood supply to the heart and brain; reduce blood viscosity, resist platelet aggregation, prevent thrombosis and dissolve blood; lower blood sugar and blood lipids.
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