Scutellarin

Description

Scutellarin is a flavone that has been found in S. barbata and has diverse biological activities, including anticancer, lipid lowering, antioxidative, and neurocognitive properties. It inhibits proliferation of PC-9 and H1975 non-small cell lung cancer (NSCLC) cells in a concentration-dependent manner and induces apoptosis and autophagy when used at a concentration of 160 μM, effects that can be blocked by the autophagy inhibitor HCQ . Scutellarin (30 and 60 mg/kg per day) reduces tumor growth in an H1975 mouse xenograft model. It decreases serum total cholesterol and LDL-cholesterol and increases HDL-cholesterol in a high-fat diet-induced mouse model of non-alcoholic fatty liver disease (NAFLD) when administered at doses of 25 and 50 mg/kg. It decreases hepatic malondialdehyde (MDA), glutamic-oxalacetic transaminase (GOT), and glutamic-pyruvic transaminase (GPT) activity, increases catalase (CAT) and total antioxidative capacity (T-AOC) activity, and increases the hepatic expression of PPARγ, PGC-1α, and Nrf2 in the same model. Scutellarin (5, 25, and 50 mg/kg per day) also prevents deficits in spatial and novel object memory in rats in the Y maze and novel object recognition test, respectively.

Chemical Properties

Soluble in alkali and glacial acetic acid, pyridine, slightly soluble in general organic solvents, insoluble in water. Suggest to dissolve with DMSO Plant source has the leaves of Scutellaria altissima L., family Labiatae

Uses

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.

Definition

ChEBI: The glycosyloxyflavone which is the 7-O-glucuronide of scutellarein.

Synthesis

119262-68-9

27740-01-8

General procedure: 20 g (42 mmol) of methyl (2S,3S,4S,5R,6S)-6-((5,6-dihydroxy-2-(4-hydroxyphenyl)-4-yloxy-4H-benzopyran-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate was dissolved in a mixed solvent of 300 mL of water and 300 mL of acetone at 0 °C Stirring. Under the protection of nitrogen, 70 mL of 10% aqueous sodium hydroxide solution was slowly added dropwise, and the reaction temperature was maintained at 0 °C with continuous stirring for about 2 h. The reaction process was monitored by HPLC. After the reaction was completed, 10% hydrochloric acid aqueous solution was slowly added dropwise under stirring to adjust the pH of the reaction solution to 2.0-3.0, and stirring was continued for 1 hour. Subsequently, the reaction system was gradually brought to room temperature and a large amount of yellow solid 5,6,4'-trihydroxyflavone-7-yloxy-glucuronic acid was observed to precipitate gradually. The reaction mixture was allowed to stand at room temperature overnight, followed by diafiltration and the filter cake was washed with appropriate amount of water and acetone and dried. Finally, purification by ethanol recrystallization afforded 17.3 g of pure 5,6,4'-trihydroxyflavone-7-yloxy-glucuronic acid in 89% yield. The purity of the product was 98.74% by HPLC, and its HPLC chromatogram is shown in Fig. 1, and the statistical results are shown in Table 1.1H-NMR (400 MHz, DMSO) data were as follows: δ 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), 6.99 (1H, s), 6.94 (2H, d, J = 8.8Hz). d, J = 8.8 Hz), 6.86 (1H, s), 5.51-5.31 (3H, br), 5.28 (1H, d, J = 7.5 Hz), 4.11 (2H, d, J = 9.6 Hz), 3.43 (4H, m).

in vivo

IC 50

STAT3; HIV-1

References

[1] Patent: EP2840088, 2015, A1. Location in patent: Paragraph 0042