Name | Alkannin |
Synonyms | ALKANNIN Alkannin ANCHUSIN NSC 94524 Arnebin IV Anchusaic acid GroMwell Root Extract (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)-1,4-naphthoquinone |
CAS | 517-88-4 |
EINECS | 208-245-7 |
Molecular Formula | C16H16O5 |
Molar Mass | 288.3 |
Density | 1.373±0.06 g/cm3(Predicted) |
Melting Point | 149° |
Boling Point | 567.4±50.0 °C(Predicted) |
Specific Rotation(α) | 20Cd -165° (benzene); -226° (chloroform). Also reported as -254 ± 7° (chloroform) (Toribara) |
pKa | 7.34±0.20(Predicted) |
Toxicity | LD50 in male, female mice, rats (g/kg): 3.0 ± 1.0; 3.1 ± 0.1; >1.0 orally (Majlathova) |
plant extract | The Lithospermum extract is a dry root extract of the Lithospermum plant Xinjiang arnebia euchroma or Lithospermum neticeae. Shikonin cold taste sweet, salty, into the liver, heart meridian, with cooling blood and promoting blood circulation, detoxification through blood stasis effect. Its main active ingredients are naphthoquinone pigments, such as acetylshikonin, shikonin, etc. Modern pharmacological studies have shown that Lithospermum has good anti-inflammatory, antibacterial, antifertility, antioxidant, anti-tumor, hypoglycemic, liver protection and cardiovascular system. The anti-inflammatory and bacteriostatic effect is the traditional efficacy of lithospermum, that is, anti-inflammatory, astringent and antipyretic. The anti-inflammatory components in Lithospermum mainly exist in the alcohol extract. Lithospermum is the dried root of Arnebia euchroma (Roy le) John St., Lithospermum erythronzon Sieb. et Zucc. Or Inner Mongolia Arnebia gutta Bunge. Also known as the purple Dan, purple spirit, red spirit, red spirit, ground blood, arborvitae, soft lithospermum, lithospermum, lithospermum, lithospermum root, old lithospermum, lithospermum, lithospermum, etc. Born in the mountain field, road side and Xiangyang slope, mainly in Heilongjiang, Jilin, Liaoning, Hebei, Henan, Hunan, Guangxi and other places. Plant morphology: perennial herb, 40-80cm in height. Root thick, conical, purple-red, purple when dry. Stems were upright, with flat-volt-shaped thick and firm hairs. The leaves are alternate, in the form of a cone, 4-8cm in length, 1-2cm in width, without stem or with short stem, both sides are short thick bristles. Inflorescence racemose; Calyx lobes linear; Corona White, 6-8mm long, Throat 5 scales, scales slightly concave at Apex, ovary 4, nutlets 4, usually becoming minority due to degeneration, gray-white, smooth and glossy. Flowering 5-6 months, fruit 7-8 months. This information was compiled by Lin Xiangyun. Figure 1 is the Lithospermum |
Chemical constituents and properties | shikonin and its derivatives are the main active components isolated from the plant shikonin, it is a highly fat-soluble naphthoquinone pigment, mainly including shikonin, acetyl shikonin,β-hydroxyisovaleryl shikonin,β-HIVs, Β-hydroxyisovalerylalkannin, β,β-dimethacryloylalkannin, β,β-dimethacryloylshishimin and β-acetoxyisovaleryl acanin (β). Shikonin: molecular formula C16H16O5, molecular weight 288.31. Purple Flake crystal or crystalline powder, mp 147 ℃ ~ 149 ℃,[α]D 20 138 ° (benzene). Insoluble in water, soluble in alcohol, organic solvents and vegetable oils. Soluble in alkaline water, acid precipitation and precipitation. Figure 2 structural formula of shikonin |
extraction method | extraction and separation of total naphthoquinone shikonin → chloroform ultrasonic extraction → extract → Recovery of chloroform → total naphthoquinone shikonin extraction and separation of shikonin → petroleum ether (30°C-60 °) soxhlet extraction for 4 hours → extract → Recovery of petroleum ether → dark red thick substance → add methanol to dissolve, discard insoluble substance → methanol liquor → Recovery of methanol, low-temperature drying → shikonin |
pharmacological action | 1. Hypoglycemic effect of lithospermum leaf extract and shikonin (A, B, C) have obvious hypoglycemic effect. 2. Antibacterial effect of lithospermum extract on Jingke 68-1 Virus test tube has inhibitory effect on Staphylococcus aureus, Staphylococcus Albus, Pseudomonas aeruginosa, Escherichia coli, Salmonella Typhi, Streptococcus A, streptococcus B has obvious bacteriostatic effect. 3. Effect on blood coagulation intraperitoneal injection of shikonin components (shikonin, acetyl shikonin) does not affect the blood coagulation time, but can prevent the anticoagulant effect of heparin. 4. Anti-tumor effect the extract of arnebia euchroma has a certain inhibitory effect on the late stage of DNA synthesis (G2 phase) of Hela cells. 5. Effects of shikonin on inhibiting proliferation, promoting apoptosis and inducing cell cycle arrest of drug-resistant human choriocarcinoma cell line (JAR/MTX) in vitro, experiments showed that the concentration of shikonin increased with the increase of the dose and the extension of the action time, the inhibition rate of the growth of choriocarcinoma resistant cells was also significantly increased. 6. Effect of shikonin on the function of hypothalamic-pituitary-gonadal axis in adolescent female rats the experiment showed that the serum hormone level of the arnebia euchroma group was significantly lower than that of the negative control group, there was no significant difference compared with the positive control group. The results indicate that shikonin can inhibit the function of hypothalamic-pituitary-gonadal axis in rats. 7. The experimental study of anti-Virus effect showed that L-shikonin at the concentration of 6.0~0.75 mg/mL could inhibit the pathogenic degeneration of chicken embryo cells from Parainfluenza Virus to Virus, and shikonin could inhibit the replication of multi-drug resistant HIV Virus strain; arnebia polysaccharide has HPV-DNA inhibition activity in vitro, and has obvious anti-human papilloma Virus effect. 8. Anti-inflammatory and anti-allergic effects the water extract and alcohol extract of arnebia euchroma have certain anti-inflammatory effects, which can reduce xylene-induced ear swelling in mice, and have inhibitory effects on specific allergic reactions, it can inhibit the release of histamine from rat peritoneal mast cells in a dose-dependent manner. 9. Protective effect of lithospermum extract on D-galactosamine induced liver injury, can significantly inhibit D-galactosamine liver injury in mice alanine aminotransferase (ALT), aspartate aminotransferase (AST) malondialdehyde (MDA) increased and superoxide dismutase (SOD), glutathione peroxidase (GSH-PX) decreased. Other Lithospermum petroleum ether and chloroform extracts not only can significantly inhibit the oxidation of lard, effectively scavenging free radicals, with strong reducing ability, but also can participate in redox reaction. |
physical and chemical identification | (1) take 0.5g powder of this product, place it in a test tube, and heat the bottom of the tube, red gas was generated and condensed into red-brown oil droplets on the wall of the test tube. (2) take 0.5g of this product powder, add 20ml of petroleum ether (60~90 C), ultrasonic treatment for 20 minutes, filtration, filtrate concentration to about 1ml, as a test solution. Another 0.5g of shikonin control medicinal material was taken, and the control medicinal material solution was prepared by the same method. According to the thin layer chromatography test, 4 μl of each of the above two solutions were absorbed, respectively, on the same silica gel G thin layer plate, with cyclohexane-toluene-ethyl acetate-formic acid (5:5:0.5:0.1) for the development of the agent, expand, take out, dry. In the chromatogram of the test article, the same purplish red spot was displayed at a position corresponding to the chromatogram of the control medicinal material; After spraying with 10% potassium hydroxide methanol solution, the spot turned blue. |
efficacy | arnebia euchroma is a drug for liver and pericardium, which is specially used in blood. Function of heat, cool blood, swelling, detoxification and laxative, it can be used for blood heat toxin and stool secret disease. Can also be used for skin damage, skin disease. Modern measles popular fashion with its decoction as a preventive medicine, quite effective. |
Use | for antipyretic, detoxification, anti-inflammatory drugs. Oral prevention of measles, made of ointment for external use can promote granulation and used for swelling, burns, chilblain, eczema, water cells. The patient also received Tongli bowel movement. In recent years, the tissue culture method has also been used to produce canned shikonin, which is used as a cosmetic. Shikonin is an enantiomeric dye extracted from shikonin and shikonin. It can be used as a dye, and has wound healing, anti-inflammatory, antibacterial, anti-tumor and other effects. |
avoid | those with gastrointestinal weakness and smooth stool |
production method | is present in the root of a plant of the family lithospermum, arnebia euchroma, etc. Shikonin can also be produced by cell culture of shikonin. |