(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione
Cryptotanshinone
CAS: 35825-57-1
Molecular Formula: C19H20O3
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione - Names and Identifiers
| Name | Cryptotanshinone |
| Synonyms | Cryptotanshinone CRYPTOTANSHINONE TANSHINONE, CRYPTO TANSHINONE, CRYPTO(P) hexahydro-1,6,6-trimethyl-,(R)- Phenanthro[1,2-b]furan-10,11-dione,1,2,6,7,8,9- (R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione (r)-1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione (1R)-1,6,6-trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dione |
| CAS | 35825-57-1 |
| InChI | InChI=1/C19H20O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,10H,4-5,8-9H2,1-3H3/t10-/m0/s1 |
| InChIKey | IJSBKZLSTIFYIE-FPKDZHNTSA-N |
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione - Physico-chemical Properties
| Molecular Formula | C19H20O3 |
| Molar Mass | 296.36 |
| Density | 1.23±0.1 g/cm3(Predicted) |
| Melting Point | 192°C(lit.) |
| Boling Point | 459.0±45.0 °C(Predicted) |
| Specific Rotation(α) | -91.4 (CHCl3) |
| Flash Point | 203.4°C |
| Solubility | Soluble in methanol, ethanol, benzene, ether, soluble in acetone, chloroform |
| Vapor Presure | 1.31E-08mmHg at 25°C |
| Appearance | Orange red needle crystal |
| Color | orange-brown |
| Maximum wavelength(λmax) | ['263nm(lit.)'] |
| BRN | 5445400 |
| Storage Condition | 2-8°C |
| Sensitive | Sensitive to light |
| Refractive Index | 1.602 |
| MDL | MFCD07636810 |
| Physical and Chemical Properties | Soluble in methanol, ethanol, benzene, ether, soluble in acetone, chloroform. From Labiatae plant salvia miltiorrhiza. |
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all |
| WGK Germany | 3 |
| RTECS | SF8282645 |
| HS Code | 29321900 |
| Hazard Class | 6.1 |
| Packing Group | III |
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione - Introduction
Pharmacological effects: It has anti-oxidation and anti-aging functions, and has a certain effect on the treatment of coronary heart disease, angina pectoris, and myocardial damage. Cryptotanshinone has antibacterial effect, 1 mg/ml has inhibitory effect on Staphylococcus aureus and Pseudomonas aeruginosa, and also has certain inhibitory effect on hemolytic streptococcus.
Last Update：2022-10-16 17:24:52
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione - Reference Information
| plant source: | salvia miltiorrhiza |
| Overview | Cryptotanshinone (cryptotanshinone,CTS) is the main fat-soluble extract of Salvia miltiorrhiza. It is an orange needle-like crystal. It belongs to diterpene quinone compounds. Most of these components have a ternary or quaternary ring o-quinone or p-quinone structure on the skeleton, making most of them have anti-tumor, antioxidant, anti-inflammatory, antibacterial and other activities. In recent years, great progress has been made in the study of the pharmacological activity mechanism of this compound. |
| effect | 1) therapeutic effect on hepatobiliary cancer the anti-cancer target of cryptotanshinone is predicted by screening technology based on reverse efficacy. The results showed that cryptotanshinone could inhibit the proliferation of human liver cancer SMMC-7721 cells in cell experiments, which may be closely related to its reduction of MAP2K1 protein mRNA expression. In the experiment of human liver cancer HepG-2 cells, Xie Fei found that cryptotanshinone can inhibit Bcl-2 expression, promote Bax expression, regulate Bel-2/Bax ratio, and finally activate downstream effector easpase-3, thus inducing HepG-2 apoptosis. 2) Therapeutic effect on prostate cancer Prostate cancer (PCa) is a common clinical cancer, and androgen receptor (AR) is the main goal of treating PCa. Reducing androgen substances or preventing AR production is widely used to inhibit AR-mediated PCa cell growth. In vivo and in vitro experiments in mice, tanshinone (including cryptotanshinone, tanshinone I, and tanshinone IIA) can inhibit 130PCa cells, and its mechanism may be by blocking the cell cycle and inducing apoptosis, thereby inhibiting its growth. In addition, cryptotanshinone can inhibit PCa by inhibiting lysine-specific demethylase 1(LSD1), regulating the demethylation function of histone H3 lysine 9(H3K9), down-regulating AR signal and inhibiting its transcriptional activity. It not only affects AR function, but also significantly inhibits AR transcription activity and AR target gene expression at mRNA and protein levels. At the same time, it also blocks the interaction between AR and lysine specific demethylase 1LSD1), inhibits AR target gene promoter, and increases monomethylation and dimethylation of histone H3 lysine 9(H3K9). |
| Salvia miltiorrhiza active ingredient | Cryptotanshinone (cryptotanshinone) is a diterpene quinone extracted from the dried root and rhizome of Salvia miltiorrhiza, a plant in the family Lamiaceae. It is a representative component of the fat-soluble components of Salvia miltiorrhiza, a drug for promoting blood circulation and removing blood stasis. It has the effects of anti-androgen excessive secretion, killing Corynebacterium acne, and eliminating inflammation, therefore, it has a good effect on the treatment of acne. In addition, cryptotanshinone also has the potential function of delaying the deterioration of early Alzheimer's disease. |
| source plant | the main source is Salvia Salvia miltiorrhiza Bge, a Labiatae plant. Dry roots and rhizomes. It is named "Danshen" because of its red color and shape similar to ginseng, also known as blood ginseng, purple salvia, red salvia, etc. The same genus includes about 700-1050 species, all over the world In the warm zone, mainly distributed in the Mediterranean and West Asia. There are about 83 species, 25 varieties and 9 variants of this genus in China, mainly distributed in southwest China. Figure 1 is a picture of Salvia miltiorrhiza. |
| chemical components of salvia miltiorrhiza | 80% components in salvia miltiorrhiza were reported after the 70s, and most of them were discovered by Chinese scholars. at present, there are more than 80 components in salvia miltiorrhiza that have clarified their structures, of which diterpenoids account for more than half, and most of these compounds are isolated from roots, and there are few studies on the aboveground part. Salvia miltiorrhiza mainly contains two major components: one is fat-soluble diterpenoids, and the other is water-soluble polyphenolic acids. Both types have pharmacological activities. In addition to diterpene quinone compounds and phenolic acid compounds, many other structural types of compounds such as salvia miltiorrhiza lactone alkaloids have been found in salvia miltiorrhiza. Salvia miltiorrhiza also contains 15 kinds of free amino acids such as glutamic acid, alanine, aspartic acid, histidine, isoleucine, phenylalanine, threonine and arginine, as well as calcium, magnesium, barium, aluminum, nickel, selenium, iron, zinc, tin and other inorganic elements. |
| pharmacological activity | cryptotanshinone is a representative component in the fat-soluble components of salvia miltiorrhiza, a drug for promoting blood circulation and removing blood stasis. its unique chemical structure and pharmacokinetic characteristics make it gradually become the object of attention. Recent studies have confirmed that it has shown good prospects in cardiovascular diseases, anti-tumor, antibacterial and anti-inflammatory, metabolic disorders and neurodegenerative diseases. 1. Antimicrobial effect: The chemical components separated from total tanshinone have been proved by in vitro antibacterial tests. Cryptotanshinone has the strongest antibacterial activity and high content, so it is the main antibacterial activity in total tanshinone. Component. Cryptotanshinone has a significant inhibitory effect on Staphylococcus aureus, methicillin-resistant Staphylococcus aureus and β-lactamase-positive Staphylococcus aureus. Cryptotanshinone destroys the structure of the bacterial cell wall and cell membrane, leading to The permeability of the cell membrane increases, which in turn makes the cell contents leak; at the same time, Cryptotanshinone has a certain effect on the synthesis of bacterial protein, which reduces the protein in the cell, and affects and hinders the expression of protein in the cell, eventually lead to the loss of normal physiological functions of bacteria. 2. Anti-tumor effect: It has cytotoxic activity on selected human cancer cell lines HeLa, HepG2 and OVCAR-3, and its IC50 is 17.2, 29.7 and 9.12 μmol/L respectively. 3. Cardiovascular protection: It can prevent and treat blood coagulation and restore blood circulation. 4. Anti-allergic effect: Under the guidance of anti-allergic activity tracking, tanshinone Ⅰ, tanshinone ⅡA, cryptotanshinone and dihydrotanshinone Ⅰ were isolated from Salvia miltiorrhiza, and it was found that they have interference with IgE receptor-mediated PLCγ2 and MAPK tyrosine phosphorylation. Among them, dihydrotanshinone I and cryptotanshinone activity is significant, IC50 is 16 and 36 μM respectively. The results indicate that dihydrofuran ring may play an important role in its activity. |
| extraction and purification | at present, the extraction methods of cryptotanshinone reported in the literature mainly include water-alcohol method, ultrasonic method, flash extraction method, microwave method, etc., while the purification methods of extract mainly include Na2CO3 solution washing, macroporous adsorption resin adsorption, countercurrent chromatography, etc. the ethanol extraction process of salvia miltiorrhiza and the ethanol extraction process after water extraction were compared. The results showed that the fat-soluble part of Salvia miltiorrhiza was extracted by water extraction and alcohol extraction, and cryptotanshinone was separated from it by silica gel column chromatography and recrystallization. The extraction and separation method improves the utilization rate of Salvia miltiorrhiza, is simple and time-saving, and is suitable for large-scale production. Purification of NaHCO3: Salvia miltiorrhiza was used as raw material, ultrasonic extraction with 95% ethanol, extraction and purification of fat-soluble components in Salvia miltiorrhiza was carried out by NaHCO3 solution, and the contents of tanshinone ⅡA and cryptotanshinone in the extract were determined by high performance liquid chromatography. Based on this and the quality of fat-soluble extract as evaluation indexes, orthogonal test was designed to investigate the extraction times of NaHCO3 solution, concentration of NaHCO3 solution, extraction times and solid-liquid ratio. The results showed that the optimum conditions for extraction and purification of tanshinone ⅡA and cryptotanshinone from Salvia miltiorrhiza were as follows: 5% NaHCO3 solution for 3 times and 6.48 times 95% ethanol for 2 times. Microwave-assisted extraction method: The microwave-assisted extraction process of cryptotanshinone from Salvia miltiorrhiza was optimized and the content of cryptotanshinone was determined. Orthogonal experiment was used to optimize the extraction process of microwave-assisted extraction method. The content of cryptotanshinone was determined by ultraviolet spectrophotometry. The results showed that the optimal extraction conditions of cryptotanshinone were as follows: ethanol concentration 95%, extraction time 5min, solid-liquid ratio 1:12, and extraction content of cryptotanshinone 1.5 mg/g. The method is fast, efficient, stable and reproducible. |
| determination of content | determination of cryptotanshinone has been reported by high performance liquid chromatography, electrochemical method, fluorescence spectrophotometry, etc. 1. HPLC method Determination of baicalin, cryptotanshinone and tanshinone ⅡA in Danqin dropping pills by HPLC. Preparation of 1.1 reference substance solution: 24, 10 and 12mg of baicalin, cryptotanshinone and tanshinone ⅡA reference substance are accurately weighed respectively, placed in a 100mL brown volumetric flask, dissolved with ethanol and diluted to scale, and shaken well. Accurately measure 5mL, place it in a 10mL brown volumetric flask, add ethanol to dilute to scale, shake well, and obtain a mixed reference solution containing 120 μg/mL of baicalin, 50 μg/mL of cryptotanshinone and 60 μg/mL of tanshinone Ⅱ A60μg/mL respectively. 1.2 Preparation of the test solution: Take 20 Danqin dripping pills, grind them evenly, weigh 125mg precisely, place them in a 50mL conical flask, add 25mL ethanol precisely, weigh them, dissolve them by ultrasound for 5min, dry the wall of the flask, make up the lost ethanol, shake well, and obtain the product. 1.3 chromatographic conditions and system applicability tests: MZC18 analytical column (250mm × 4.6mm,5 μm),C18 protective column (Beijing Analytical Instrument Factory, 5.0mm × 4.6mm,5 μm); Mobile phase A is 85% acetonitrile aqueous solution (containing 0.5% triethylamine, phosphoric acid adjusted pH3.0), mobile phase B is 10% acetonitrile aqueous solution (containing 0.5% triethylamine, phosphoric acid adjusted pH3.0), gradient elution, the program is 0 ~ 100%,B 80% ~ 0%; Volume flow rate: 1.0 mL/min; Detection wavelength: 270nm. Under this chromatographic condition, baicalin, cryptotanshinone, tanshinone ⅡA reference substance, negative samples (the mass ratio of PEG6000, PEG1000, and propylene glycol is heated and melted at 7: 63: 10) and Danqin Dropping Pills were measured. Figure 1. It can be seen that the retention times of baicalin, cryptotanshinone and tanshinone ⅡA are 6.7, 19.3 and 22.8min respectively, and the separation degree from their adjacent peaks is greater than 1.5. The theoretical plate number analysis is 3600, 7500 and 6300. 2. electrochemical method because cryptotanshinone molecule contains quinone structure and is easy to be redox, it can be detected by electroanalytical chemistry method. The electrochemical behavior of cryptotanshinone on the electrode was studied by cyclic voltammetry and a new method for the determination of cryptotanshinone by differential pulse voltammetry was established. In pH 4.0 acetate buffer, the oxidation peak current has a good linear relationship with the concentration of cryptotanshinone in the range of 3.0 × 10-8~2.0 × 10-7mol/L, and the detection limit is 2.0 × 10-9mol/L. Glassy carbon electrode can effectively eliminate the interference of other components in the sample to the determination of cryptotanshinone, and has been used for the direct determination of cryptotanshinone in actual samples. The method has high sensitivity and wide detection range. |
| preparation research | cryptotanshinone is insoluble in water, has low dissolution in vitro and low oral bioavailability. In order to improve the dissolution of cryptotanshinone, various preparations were studied. 1. Liposomes Cryptotanshinone nanoliposomes were prepared by ultrasonic-homogenate-freeze-drying method. Liposome as a new drug carrier has good effects in improving the dissolution rate of drugs, enhancing the targeting, slow release, controllability, low degree and intelligence of drugs. In addition, it can also activate the body's own immune function, reduce the therapeutic effect of drugs, and improve the patient's compliance. Cryptotanshinone nanoliposomes were prepared by freeze-drying method with a particle size of 20-80nm. With the decrease of the ratio of soybean lecithin to cryptotanshinone, the particle size gradually decreases and the encapsulation efficiency gradually decreases. In vitro drug release showed zero-order kinetic drug release characteristics. The best process conditions for preparation, the weight ratio of drug/carrier is 1:20, and the volume ratio of water/oil is 3:2. 2. Solid dispersion The solid dispersion of cryptotanshinone-PVP was prepared by solvent evaporation method, and the solid dispersion of cryptotanshinone-PEG was prepared by melting method. The properties of solid dispersion and its effect on dissolution were studied by in vitro dissolution, differential thermal analysis and microscopic observation. Results On the surface, the dissolution rates of PVP and PEG solid dispersions reached 9.7 times and 7.5 times of that of bulk drugs respectively in 45min. The characteristic melting peak of cryptotanshinone disappeared in DTA curve of solid dispersion. Both solid dispersions can significantly improve the dissolution of cryptotanshinone, while PVP solid dispersion has higher dissolution than PEG solid dispersion. |
| metabolism in vivo | within 3 hours after oral administration of cryptotanshinone in rats, the first metabolites in bile include tanshinone II-A in addition to the original drug, indicating that dehydrogenase in the intestine or liver may convert cryptotanshinone into tanshinone II-A. 1,2,3,4 and 5 metabolites with greater polarity than cryptotanshinone appeared in bile after 6 hours of oral administration of the drug in rats, indicating that the drug has undergone repeated hepatic and intestinal circulation and is catalyzed by liver microsomal drug enzymes., Gradually converted into corresponding metabolites. For example, hydroxytanshinone II-A may be catalyzed by hydroxylase, and the condensate of tanshinone II-A and glutamate may be converted by acyl-CoA and glutamate 2-N acyltransferase. Metabolites 2,3,5 and 6 were positive in vitro antibacterial tests, but the original drug (No. 6) was still the most active, so the original drug may still be the main pharmacological effect in animals. Figure 2 shows the possible pathways for the biotransformation of cryptotanshinone in animals. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: It has anti-oxidation and anti-aging functions, and has a certain effect on the treatment of coronary heart disease, angina pectoris, and myocardial damage. Cryptotanshinone has antibacterial effect, 1 mg/ml has inhibitory effect on Staphylococcus aureus and Pseudomonas aeruginosa, and also has certain inhibitory effect on hemolytic streptococcus. a diterpenoid compound, is an effective STAT3 inhibitor. |
Last Update：2024-04-09 21:11:58
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View History
(R)-1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-phenanthro(1,2-b)furan-10,11-dione
3-Formyl-indazole-1-carboxylic acid tert-butyl ester
2-Oxopentanedioic acid calcium salt
(hydroxyethyl)urea
丁氧基乙烯
3-Formyl-indazole-1-carboxylic acid tert-butyl ester
2-Oxopentanedioic acid calcium salt
(hydroxyethyl)urea
丁氧基乙烯