Name | Wogonin |
Synonyms | WOGONIN Wogonin vogonin Wogonin 632-85-9 5,7-DIHYDROXY-8-METHOXYFLAVON 5,7-DIHYDROXY-8-METHOXYFLAVONE 5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one 5,7-dihydroxy-8-methoxy-2-phenyl-4h-1-benzopyran-4-on 5,7-dihydroxy-8-methoxy-2-phenyl-4h-1-benzopyran-4-one 5,7-Dihydroxy-8-methoxy-2-phenyl-4H-1-benzopyran-4-one |
CAS | 632-85-9 |
EINECS | 1592732-453-0 |
InChI | InChI=1/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3 |
InChIKey | XLTFNNCXVBYBSX-UHFFFAOYSA-N |
Molecular Formula | C16H12O5 |
Molar Mass | 284.26 |
Density | 1.420±0.06 g/cm3(Predicted) |
Melting Point | 203-206°C |
Boling Point | 518.8±50.0 °C(Predicted) |
Flash Point | 198.3°C |
Solubility | Easily soluble in methanol, ethanol, acetone and ethyl acetate, soluble in ethanol, acetic acid and chloroform, slightly soluble in benzene and water, insoluble in carbon disulfide and petroleum. |
Vapor Presure | 2.21E-11mmHg at 25°C |
Appearance | Yellow needle crystal |
Color | Light Yellow to Yellow |
Maximum wavelength(λmax) | ['319nm(EtOH)(lit.)'] |
pKa | 6.83±0.40(Predicted) |
Storage Condition | Inert atmosphere,2-8°C |
Refractive Index | 1.668 |
MDL | MFCD00017736 |
Physical and Chemical Properties | It is very soluble in methanol, ethanol, acetone and ethyl acetate, soluble in ethanol, acetic acid and chloroform, slightly soluble in benzene and water, insoluble in carbon disulfide and petroleum. From the root of Scutellaria baicalensis Georgi |
Safety Description | 24/25 - Avoid contact with skin and eyes. |
WGK Germany | 3 |
RTECS | LK8331000 |
HS Code | 29329990 |
Plant Source: | Scutellaria baicalensis Georgi |
Scutellaria baicalensis | Scutellaria baicalensis Georgi is the dried root of Scutellaria baicalensis Georgi. Born in the grassland, high gravel slope; China's main production in Hebei, Inner Mongolia, Shanxi, Shandong, Shaanxi and other places. [plant morphology] perennial herb. The main root was thick, slightly conical, with brown skin. Stem square, 25-60cm in height, base multi-branched, smooth or short-hairy. Leaves opposite, egg-shaped, or linear-shaped, 1.5-4.5 in length, 3- 12mm in width, Apex obtuse or acute, base rounded, entire, with eyelashes, upper smooth or short hair, with glandular dots below, smooth or short hair only in the middle rib; Sessile or short-stalked. Racemose axillary, flowers biased to one side; Calyx bell-shaped, white villous, Apex 5-lobed; Crown lip-shaped, upper lip longer than lower lip, tube-shaped, distally enlarged, base very thin, purple, 2-2.5cm long, with white pubescence on the surface; Stamens 4,2 strong; Pistil 1; Ovary 4-dehiscence, basolateral in style. Small nuts 4, rounded, black. Flowering period: July-August. Fruiting period: 8-9 months. [chemical constituents] The root of Scutellaria baicalensis Georgi contains baicalein, baicalin, wogonin, wogonin, scutellarin, benzoic acid, β-sitosterol, etc. Baicalein is contained in stems and leaves. harvested from spring to early summer (Autumn is also available). Plants grown for 3 to 4 years were selected. After the roots were excavated, the stems and seedlings, fibrous roots and soil were removed. When the roots were half-dried, the skin was removed and dried. Figure 1 is the dried root of plant Scutellaria baicalensis |
pharmacological effects | wogonin is a flavonoid compound extracted from the root of Scutellaria baicalensis Georgi, including antioxidant activity, anti-inflammatory, immunomodulatory effects. In addition, it also has neuroprotective effect in cerebral ischemia. The small intestine excised in mice showed a papaverine-like spasmolytic effect, but the effect was weak, about 1/5 of papaverine. Oral administration of wogonin can reduce the level of triglyceride induced by ethanol in rats. Wogonin also has anti-cancer and diuretic effects. |
Anti-inflammatory and anti-allergic effects | The decoction of Scutellaria baicalensis Georgi had obvious inhibitory effect on yeast-induced foot swelling of rats; the methanol extract of Scutellaria baicalensis, baicalein, baicalin and wogonin can inhibit the increase of vascular permeability induced by acetic acid in mice and reduce the Acute plantar edema induced by synthetic polyamines in rats, inhibition of secondary damage of bone degeneration in rats with adjuvant arthritis. Baicalin and aglycone could inhibit the hyperpermeability of mouse ear capillaries induced by experimental inflammation. The compound Scutellaria baicalensis injection, anti-inflammatory oral liquid, huangqin decoction and so on, have obvious anti-inflammatory effect. The anti-inflammatory mechanism of Scutellaria baicalensis Georgi was preliminarily considered to be related to its anti-arachidonic acid (AA) metabolism. |
hypolipidemic effect | Scutellaria baicalensis Georgi has significant hypolipidemic effect, and its main effective component is flavonoid. Baicalin and baicalein could reduce the levels of serum free fatty acid, triglyceride and liver total cholesterol, free cholesterol, triglyceride in experimental hyperlipidemia rats; Wogonin could reduce the levels of serum and liver triglyceride; scutellarin Ⅱ can reduce serum total cholesterol and liver triglyceride concentration; Baicalein and wogonin can also increase serum high density lipoprotein (HDL)-cholesterol levels. Baicalein and baicalin can increase the concentration of Serum Phospholipid and decrease the level of phospholipid in liver tissue. The flavonoids in Scutellaria baicalensis Georgi can inhibit lipolysis of rat adipose tissue and inhibit fat synthesis from glucose. |
antithrombotic effect | various components of Scutellaria baicalensis Georgi can inhibit platelet aggregation, such as baicalein, wogonin, scutellarin and chrysin at a concentration of 110mol/L can inhibit the aggregation of platelet induced by collagen, chrysin and baicalein, wogonin can also inhibit platelet aggregation induced by ADP and arachidonic acid, and baicalein and baicalin can also inhibit the conversion of fibrinogen into fibrin induced by thrombin, and can prevent the diffuse intravascular coagulation induced by endotoxin. The above effects can prevent thrombosis. Its inhibition of platelet aggregation is stronger than aspirin. The mechanism of action is mainly to inhibit thromboxane A2(TXA2) synthase, so that the generation of TXA2 is reduced; At the same time, it can increase the level of cAMP, so that the platelet aggregation is obviously reduced; it can also specifically inhibit platelet 12-lipoxygenase activity, reduce the synthesis of 12-HETE, and reduce platelet adhesion. So Scutellaria has anti-thrombosis and prevention and treatment of atherosclerosis. |
diuretic effect | Scutellaria baicalensis Georgi decoction, infusions and extracts, wogonin has obvious diuretic effect on experimental animals. When the amount of urine secretion increases, the blood pressure also decreases, and baicalin has the strongest effect. Its diuretic effect may be related to the increase of PGE1 and PGE2. In the acute diuretic experiment, the effect of baicalin was the strongest, the second was wogonin, and the baicalin was worse. Scutellaria baicalensis Georgi alcohol extract and decoction (normal persons and rabbits) also have diuretic effect. |
identification method | determination conditions of wogonin by HPLC (64%) stationary phase flow rate (ml/min) detection wavelength (nm) column wenwogonin Nova-Pak C18 5 μm (4.5mm x 150mm) water-acetonitrile-glacial acetic acid (73:23:3) 1.0 25C |
the common methods of extracting wogonin from Scutellaria baicalensis Georgi | 1, steam distillation 2, organic Solvent extraction 3, Soxhlet extraction 4, enzyme extraction 5, ultrasonic extraction |
Use | for content determination/identification/pharmacological experiments. Pharmacological effects: antispasmodic effect, anti-cancer diuretic effect. for diuresis and blood pressure lowering. |