Cryptotanshinone CAS 35825-57-1

Cryptotanshinone, the molecular formula is C19H20O3, CAS 35825-57-1. It is a brown powder. It has two chiral centers and four enantiomers exist. Poor solubility, hardly soluble in water, soluble in ethanol, dimethyl sulfoxide (DMSO), methanol, acetone, chloroform and other organic solvents. When complexed with β-cyclodextrin, its solubility can be improved. The thermal properties are relatively stable, and it is not easy to volatilize and decompose at room temperature, but its melting point is low, only 86 °C. When heated to a certain temperature, it can be decomposed to produce a variety of gases, such as CO, CO2 and so on. It is a quinone diene derivative present in the rhizome of Salvia miltiorrhiza. It is widely used in the medical field and has various pharmacological activities. It can be used to treat diseases such as cardiovascular diseases, nervous system diseases, inflammation and tumors. In terms of semiconductor materials, it can be made into thin film electronic components and fluorescent probes. In the medical field, it can be used as a nano drug carrier for drug delivery and imaging. In addition, in terms of paint catalyst application, a highly efficient paint catalyst has also been successfully prepared.

Cryptotanshinone is a compound with a relatively special structure, and its main structural features are as follows:

1. Diterpene ketone structure: it belongs to diterpenoids, which contain two ring structures of six-membered ring and five-membered ring. Among them, the five-membered ring is a cyclopentadienyl ethyl ketone part, which is the most special part in the structure of product. Diterpene ketones are ubiquitous in plants and are widely used in drug research and development.

2. Benzophenone structure: The molecule of it contains a dibenzophenone structure, which is located above the five-membered ring, which is one of the characteristics different from other diterpene ketone compounds. This structure is often regarded as one of the fingerprint structures of diterpene ketones.

3. Other structural features: it contains multiple aromatic rings and double bonds, so it has strong aromaticity and instability. At the same time, because the molecule contains multiple functional groups such as hydroxyl groups and carbene groups, it has good biological activity and modifiable properties.

Due to the above structural characteristics, it is widely used in the field of medicine and has become a compound that has attracted much attention.

Hidden tanshinone is a diterpenoid compound of tanshinone type extracted from Salvia miltiorrhiza, which has various pharmacological activities. The following is a detailed introduction to its uses:

Antiviral

 

Hidden tanshinone has broad-spectrum antiviral properties. In vitro studies have shown that it can significantly inhibit the replication of various viruses, including vesicular stomatitis virus (VSV), encephalomyocarditis virus (EMCV), influenza A virus (H1N1), herpes simplex virus type 1 (HSV-1), etc., within the concentration range of 4-8 μ mol · L ⁻¹. Its mechanism of action involves blocking the virus adsorption and replication stages, and increasing the expression level of interferon stimulated genes (ISGs) by activating the JAK-STAT pathway, forming a multiple antiviral defense system.

Anti inflammatory

 

Hidden tanshinone exhibits significant activity in the anti-inflammatory field, capable of inhibiting inflammatory responses and the release of inflammatory mediators. Animal experiments have confirmed that:

As a total tanshinone component (TTS), it can effectively inhibit xylene induced ear edema in mice, reduce lipopolysaccharide induced sepsis mortality, and alleviate pathological changes of acute kidney injury.
In the lipopolysaccharide induced mouse macrophage model, salvianolic acid can inhibit the production of inflammatory mediators and significantly increase the survival rate of D-galactosamine sensitized mice.
By reducing the expression of CD14 and TLR4 and inhibiting LPS induced phosphorylation of TAK1, it exerts a protective effect on the inflammatory response.

Antiplatelet aggregation and antithrombotic effects

 

Cryptotanshinone inhibits ADP induced platelet aggregation in rats in a concentration dependent manner, and its mechanism of action is related to antagonizing platelet P2Y12 receptors. This receptor belongs to the G-protein (Gi) coupled receptor family and can inhibit platelet activation by blocking its signaling pathway. In addition, network pharmacology studies suggest that it may exert anti venous thromboembolism effects by regulating coagulation related targets.

Anti tumor

 

Hidden tanshinone exhibits multi-target and multi pathway regulatory properties in the field of anti-tumor, and has inhibitory effects on various solid tumors

Gastric cancer:
By dose dependently inhibiting the growth of gastric cancer MKN-45 cells, increasing the expression of pro apoptotic proteins and reducing the expression of anti apoptotic proteins.
The mechanism of action involves the generation of reactive oxygen species and inhibition of MAPK and Akt signaling pathways, leading to cell cycle arrest in the G2/M phase and inducing Caspase dependent apoptosis.
It can inhibit the activity of Wnt/β - catenin signaling pathway and reduce the invasive ability of gastric cancer cells.
Inhibiting PKM2 gene transcription and translation by enhancing miR-124 expression, blocking aerobic glycolysis pathway.

 

liver cancer:
As a STAT3 inhibitor, it induces apoptosis in human liver cancer Hepal-6 cells through the JAK2/STAT3 signaling pathway.
Activation of the TLR7/MyD88/NF - κ B signaling pathway enhances the immune killing of M1 macrophages against liver cancer cells.
By activating the AMPK signaling pathway, the cell cycle of human liver cancer HepG2 cells is arrested in the G1 phase, inducing autophagic cell death.
It has a radiosensitizing effect on the H22 tumor bearing mouse model of liver cancer and can arrest the cell cycle in the G2/M phase.
Inhibition of the PI3K/Akt/mTOR signaling pathway induces autophagy in HepG2 cells and induces ferroptosis by increasing the accumulation of reactive oxygen species.

Prostate cancer:
As an AR inhibitor, it blocks AR dimerization and AR co regulatory factor complex formation, inhibiting androgen/AR mediated cell growth.

 

Disrupting the interaction between AR and LSD1, inhibiting LSD1 mediated H3K9 demethylation, and reducing AR signaling.
Inducing apoptosis and autophagic cell death in human prostate cancer DU145 cells involves upstream triggering factors such as death related protein kinases and reactive oxygen species.
Inhibit downstream PI3K/Akt signaling pathway by reducing the expression of heteromucin.
Bladder cancer:
The mechanism of inducing autophagy in T24 and UMUC-3 cells of bladder cancer involves inhibiting the activation of PI3K/Akt/mTOR signaling pathway.
leukemia:
It has a proliferative inhibitory effect on leukemia cell lines, and the mechanism may be related to inducing cell differentiation or apoptosis.

Antibacterial

 

Has inhibitory effects on various pathogenic bacteria:

At a concentration of 1mg/ml, it can inhibit the growth of Staphylococcus aureus and Pseudomonas aeruginosa, and also has a certain inhibitory effect on Streptococcus pyogenes.
By disrupting the bacterial cell wall and membrane structure, increasing membrane permeability leads to the leakage of cellular contents.
Affects bacterial protein synthesis, leading to a decrease in proteins within the bacterial body and hindering their expression.

Protection of the nervous system

 

Potential in the treatment of neurodegenerative diseases:

Alzheimer's disease:
Easy to intervene in the generation and metabolism of A β through the blood-brain barrier, reducing its neurotoxic damage.
As a non competitive inhibitor, it inhibits acetylcholinesterase (AChE) activity and restores acetylcholine levels.
It has a significant protective effect on glutamate induced cortical neuron apoptosis, and the mechanism involves inhibiting intracellular reactive oxygen species generation and regulating Bcl-2 protein family expression.
Cerebral ischemic injury:
Inhibit glial cell proliferation caused by ischemic injury and protect neuronal survival.

Metabolic regulation

 

Hidden tanshinone has potential application value in the treatment of metabolic diseases:

Diabetes related:
Improving the status of insulin resistant ovarian granulosa cells by regulating multiple genes and signaling pathways.
It has therapeutic effects on dexamethasone induced ovarian insulin resistance rats, reducing ovulation rate and decreasing testosterone and estrogen production.
Lipid metabolism:
The antioxidant activity of tanshinone components (including cryptotanshinone) is related to lipid metabolism regulation, and may improve lipid metabolism disorders by reducing oxidative stress.

Skin disease treatment

 

Hidden tanshinone is widely used in dermatology:

Acne:
Kill Propionibacterium acnes and Staphylococcus aureus in hair follicles, and inhibit inflammatory reactions.
To exert anti androgen effects and regulate sebum secretion, it is often used in combination with minocycline or isotretinoin to enhance therapeutic efficacy in clinical practice.
Other inflammatory skin diseases:
By inhibiting the release of inflammatory mediators and regulating immune function, symptoms such as folliculitis and dermatophytosis can be improved.

It is a natural compound with various pharmacological activities, which exists in the rhizome of Salvia miltiorrhiza. Due to the increasing demand for research and application of its pharmacological activity, there is also a high demand for research on its synthesis method.

1. Extraction from natural products:

The most common way to get It is to extract it from the rhizome of Salvia miltiorrhiza. The method includes the following steps:

(1) Collect the rhizome of Salvia miltiorrhiza and remove impurities.

(2) Extract It and other secondary metabolites from the rhizome of Salvia miltiorrhiza by means of ultrasonication and distillation.

(3) Pure Cryptotanshinone was purified by thin layer chromatography, high performance liquid chromatography and other techniques.

Although the process of this method is simple, it is not suitable for the large-scale preparation of It due to the limitation of the source of natural products.

2. Obtained by chemical synthesis:

In order to obtain a sufficient amount of It for pharmacological experiments and clinical trials, researchers have also tried many chemical synthesis methods. These methods can be grouped into the following categories:

(1) Method based on quinone compounds:

The method uses 2-hydroxy-5-methyl-1,4-benzoquinone as a raw material to obtain It through multi-step reactions.

Specific steps are as follows:

Step 1: First react 2-hydroxy-5-methyl-1,4-benzoquinone with methyl acetoacetate in the presence of sodium hydroxide at 80°C to obtain 2-hydroxy-5-methyl-3-acetoxy base-1,4-benzoquinone.

Step 2: Stir and react the above product with excess sodium carbonate, cuprous chloride and ammonia water in tetrahydrofuran for 6 hours to obtain 2-hydroxy-5-methyl-3-acetoxy-1,4-benzoquinone copper complex things.

Step 3: Decompose the above product with hydrochloric acid and methanol to obtain 2-hydroxy-5-methyl-1,4-benzoquinone.

Step 4: Stir and react 2-hydroxy-5-methyl-1,4-benzoquinone and isopropylchlorosilane in acetone for 20 hours to obtain It.

Advantages: The method has simple steps and the raw materials are readily available.

Disadvantages: The price of raw materials required by this method is high, and there are many by-products in some reactions, which makes the synthesis amount of this method unstable and the cost is high.

(2) Methods based on ketones:

The method uses 4-hydroxy-2,6-dimethyl-1,3-benzophenone as a raw material to obtain product through multi-step reactions.

Specific steps are as follows:

Step 1: Firstly, react 4-hydroxy-2,6-dimethyl-1,3-benzophenone with epoxypentane in isopropanol to obtain 4-hydroxy-3-epoxypentyl-2,6 -Dimethyl-1,3-benzophenone.

Step 2: React the above products with NaBH4 and CuCl2 respectively to obtain two products--4-hydroxy-3-epoxypentyl-2,6-dimethyl-1,3-benzophenone and 4-hydroxy-3 - Epoxypentyl-2,6-dimethyl-1,5-benzophenone.

Step 3: React the above product with bromoacetone and sodium sulfonate to obtain two products--4-hydroxy-3-epoxypentyl-2,6-dimethyl-1,3-phenyl-3- Propionyloxyacetone and 4-hydroxy-3-epoxypentyl-2,6-dimethyl-1,5-phenyl-3-sulfoacetone.

Step 4: The above product undergoes a multi-step reaction to finally obtain product.

Advantages: The method has fewer steps and the reaction product is easy to purify.

Disadvantages: This method has complicated steps, needs to use a variety of toxic chemical reagents, the process is relatively complicated, and it has great environmental pollution.

(3) The method of using microbial metabolism:

The method is based on microorganisms capable of synthesizing product, through artificial cultivation and screening, to obtain some microbial strains that can be used to produce .

Specific steps are as follows:

Step 1: Screen out microbial strains with Cryptotanshinone synthesis ability, such as Fungi, Actinomyces, etc.

Step 2: Carry out artificial cultivation of the strain under suitable conditions, such as selecting the appropriate medium, cultivation time, cultivation temperature and cultivation method, etc.

Step 3: Use biotechnology means to optimize the method, such as using genetic engineering technology to improve the synthetic ability of product.

Advantages: the method belongs to the biosynthesis method, is green and environmentally friendly, and is easy to realize industrial production.

Disadvantages: This method requires strain screening and optimization, and the process is relatively time-consuming and complicated.

All in all, the above methods can synthesize product, but their own advantages and disadvantages also need to be selected according to the application situation. In the future, with the continuous development of chemical synthesis technology and biotechnology, more new methods will be developed and provide better options for the large-scale preparation of it.

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