5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
Deoxyshikonin
CAS: 43043-74-9
Molecular Formula: C16H16O4
5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione - Names and Identifiers
5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione - Physico-chemical Properties
| Molecular Formula | C16H16O4 |
| Molar Mass | 272.3 |
| Density | 1.269±0.06 g/cm3(Predicted) |
| Melting Point | 91°C |
| Boling Point | 503.7±50.0 °C(Predicted) |
| Solubility | Soluble in methanol, ethanol, DMSO and other organic solvents |
| Appearance | Red powder |
| pKa | 7.42±0.20(Predicted) |
| Storage Condition | 2-8℃ |
| MDL | MFCD00144053 |
5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione - Reference
| Reference Show more | 1. Zhu Yongle, Dong Na, Qu Xiaolan, et al. Determination of deoxyshikonin in shikonin from different habitats by HPLC [J]. Journal of Taishan Medical College, 2017 038(011):1229-1231. 2. Dong Na, Gao Zhao Jun, Qu Xiaolan, et al. Simultaneous determination of five naphthoquinones in arnebia euchroma by HPLC [J]. Journal of Taishan Medical College, 2019, 40(05):336-338. 3. Gao Zhao-jun, Liu qiue, Qu Xiaolan, etc. Comparative study on HPLC fingerprints of arnebia euchroma and arnebia euchroma in Taishan [J]. China Modern Applied Pharmacy, 2019, 036(010):1193-1196. 4. [IF = 5.279] Wenqin Li et al."Discovery of Natural Products Multitarget Inhibitors of Insect Chitinolytic Enzymes through High-Throughput Screening."J Agr Food Chem. 2021;69(37):10830-10837 5. [IF=7.848] Mingyue Zhou et al."Oriented Layered Graphene Oxide Pad Favoring High Loading Capacity and Stability for High-Throughput Chemical Screening."Advanced Materials Technologies. 2022 Mar 11 |
5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione - Reference Information
| effective components of shikonin | deoxyshikonin is one of the main effective components of shikonin, belonging to naphthoquinone compounds. Naphthoquinone is the main active ingredient of lithospermum, its content accounted for 3 to 6.5%, with a variety of physiological and pharmacological activities, such as Callus anti-inflammatory, antibacterial, antiviral, antipyretic, hemostatic, anti-tumor, liver, hypoglycemic, sedative and immune regulation. |
| plant sources and chemical constituents | the traditional Chinese medicine Lithospermum is of the genus Anlebia euehroma John St., also known as arnebia euchroma), the genus Lithospermum (Lithospermum erythrorizon Sieb. Et Zucc., also known as Lithospermum) and dried roots of a variety of plants in the genus Arnebia gut Bunge. Mainly distributed in China's provinces, in some other countries or regions are also distributed. Lithospermum was originally recorded in the "Shen Nong herbs", with cooling blood, blood circulation, detoxification effect of rash. Used for blood fever, measles, sore, eczema, fire and water burns. There are two main components of arnebia euchroma: one is water-soluble components, the current research is relatively small, the preliminary thought is mainly a mixture of polysaccharide and glycoprotein; the other is a variety of biologically active substances with strong fat solubility, including shikonin naphthoquinones, phenolic acids, alkaloids, phenol and benzoquinones, triterpene acids and sterols, flavonoids and so on. Among them, shikonin naphthoquinone compounds, including shikonin and a series of derivatives, are important medicinal components of shikonin. Figure 1 shows the purple steppe plants. |
| physical and chemical identification | TLC identification: Take appropriate amount of sample powder and load it into percolation column, with petroleum ether (30~60 ℃) percolation, percolation liquid is concentrated to a small volume, point on silica gel G plate, with shikonin, β' acetyloxy isooctyl acanin, deoxyshikonin, acetoshikonin, β,β-dimethacryloylacanin were used as control, and ethyl acetate-petroleum ether (1:9) was used as developing solvent, the spots were all purple. |
| extraction method | there is no extraction method for the single component of shikonin in the current study. As a naphthoquinone component in arnebia euchroma, reference can be made to the reported extraction of total naphthoquinone. Comparison of the content of total naphthoquinones extracted by different methods with reference to the determination method of total pigments of naphthoquinones in Lithospermum in Chinese Pharmacopoeia (2010 Edition), take each extract dry extract 0.02g, set it in a 100ml measuring flask, add ethanol to the scale, shake it to dissolve it completely, and filter it. Take 5.0ml continuous filtrate accurately, put it in a 25ml measuring flask, add ethanol to the scale, shake the hook. According to the ultraviolet-visible spectrophotometry, the absorbance was measured at the wavelength of 516nm. According to the absorption coefficient of L-shikonin was 242, the content of total naphthoquinones in the extract was calculated. Four processes were selected for comparison, and the comparison order of total naphthoquinone content in the extracts was as follows: 95% ethanol cold soaking> 95% ethanol ultrasonic> 95% ethanol leakage> 95% ethanol reflux method. The best extraction process is precision weighing Xinjiang shikonin (S4) coarse powder 5.0g, adding 95% ethanol 60.0, cold soak extraction 8H, filter paper filtration and filtrate, determination. |
| Content determination and analysis | [chromatographic conditions] (1) normal phase chromatography: column: whatman Partisil-10PAC column (250mm × 4.6); Mobile phase: n-hexane-ethyl acetate-glacial acetic acid (89.2:10:0.8); Flow rate: 1.2ml/min; Detection wavelength: 270nm; Column temperature: 28. (2) reversed phase chromatography: Column: Lichrosorb C18 column (200mm × 5mm,10 μm); Mobile phase: chloroform-methanol-water-glacial acetic acid (14:52:28:6); Flow rate: 1.2ml/min; Detection wavelength: 270nm; Column temperature: 80. [preparation of test article] The root of this product was extracted with petroleum ether (30~60 ℃), and the extract was dewaxed and passed through Waters C18 pre-column. Figure 2 is the HPLC diagram of shikonin and its derivatives in shikonin a normal phase diagram; B reverse phase diagram; c petroleum ether extract diagram (1 deoxyshikonin 2-6 shikonin and other derivatives) |
| Structure spectrum | FIG. 3 is a multi-stage mass fragmentation mechanism of deoxyshikonin. |
| pharmacological action | 1. Chemokine inhibition: by inhibiting the activity of chemokines, anti-inflammatory, anti-tumor, anti-viral and immune regulation can be achieved. The results also show that shikonin has a selective chemokine inhibitory effect, so it is expected to be developed as a drug for the treatment of inflammatory diseases. 2. Anti-tumor effect: shikonin and its derivatives have certain inhibitory effect on tumor cell 5180. At present, the anti-tumor drugs are screened from the similar structure of shikonin at home and abroad. 3. Anti-inflammatory effect: in recent years, it was found that the water extract, ether extract and drunk extract of lithospermum have good anti-inflammatory effect. The extract of arnebia euchroma and its naphthoquinone compounds have strong inhibitory effect on Candida albicans, and the clinical application of arnebia ointment has obvious improvement effect on monilial oral diseases. 4. Liver injury protection: Lithospermum fat-soluble and water-soluble extract has a protective effect on acute liver injury, significantly reduced serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) activity, the liver tissue superoxide dismutase (SOD) and glutathione peroxidase (GsH Px) activity increased significantly, and malondialdehyde (MDA) content decreased, and can significantly reduce liver cell degeneration and necrosis. 5. Lithospermum in the treatment of scald in clinical application: Lithospermum has antibacterial, Staphylococcus aureus, Pseudomonas aeruginosa and other bacteria are inhibited, and can accelerate epithelial growth, accelerate wound healing. As a scald drug, arnebia euchroma is widely used in clinical practice. Clinical application of arnebia preparation in the treatment of burn, bedsore, eczema, sore healing and other skin diseases, the effect is obvious. |
| Industrial application | The shikonin naphthoquinone compound is also a natural plant pigment, ranging in color from orange to deep red and purple, it can also be used in cosmetics, pharmaceutical capsules, capsules, industrial printing and dyeing, detergents and other coloring. The various components and structures of shikonin naphthoquinone compounds determine the broad spectrum of their functions and the diversification of their uses, and can become the intermediate raw materials of natural products in various industries. As a natural pigment in cosmetics and printing and dyeing industry, also has great development and application prospects. |
| safe | storage method: sealed, cool, dry storage. Nature and stability: Under normal circumstances will not decompose, no dangerous reaction. |
| Use | for content determination/identification/pharmacological experiments. |
Last Update：2024-04-09 21:53:21
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View History
5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
DIBENZO-21-CROWN 7-ETHER
6369-47-7
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Inositol 1,2,3,4,5,6-hexakis(dihydrogen phosphate)
methyl [4-(1-adamantyl)(methylsulfonyl)anilino]acetate
6-butyl-6H-indolo[2,3-b]quinoxaline
548467-23-8
5-{3-nitrobenzoyl}-4,4,6-trimethyl-4,5-dihydro-1H-[1,2]dithiolo[3,4-c]quinoline-1-thione
58099-76-6
DIBENZO-21-CROWN 7-ETHER
6369-47-7
2-Thiophenecarbonitrile, 3-[(diphenylmethylene)amino]-5-methyl-
Inositol 1,2,3,4,5,6-hexakis(dihydrogen phosphate)
methyl [4-(1-adamantyl)(methylsulfonyl)anilino]acetate
6-butyl-6H-indolo[2,3-b]quinoxaline
548467-23-8
5-{3-nitrobenzoyl}-4,4,6-trimethyl-4,5-dihydro-1H-[1,2]dithiolo[3,4-c]quinoline-1-thione
58099-76-6