Oridonin CAS 28957-04-2

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Oridonin, is a light yellow needle shaped crystal with CAS 28957-04-2 and molecular formula C20H28O6. It is a bioactive natural substance isolated from Rabdosia plants in the family Lamiaceae. Its main components are natural organic compounds of the ent kau red diterpenoid type, which are colorless prismatic crystals with an extremely bitter taste. They are insoluble in water but soluble in organic solvents such as ether, methanol, and ethanol. It has the effects of clearing heat and detoxifying, reducing swelling and dispersing nodules, promoting blood circulation and relieving pain. It is an effective ingredient extracted from winter grass, which has the effects of clearing heat and detoxifying, reducing swelling and nodules, promoting blood circulation and relieving pain. It can be used to treat diseases such as tonsillitis, pharyngitis, lymphadenitis, mumps, mastitis, gingivitis, arthritis, etc.

Oridonin is a biologically active natural substance isolated from plants of the Rabdosia genus in the Labiatae family. It is also known as  Yanming Caoning. Its chemical formula is C20H28O6 (some data also indicate that its molecular formula is C20H24NO4, which may be due to differences in sources or preparation methods), molecular weight is 364.433, and CAS registry number is 28957-04-2. Ophiopogon methyl is a colorless prismatic crystal or light yellow needle shaped crystal with an extremely bitter taste. It is difficult to dissolve in water, but soluble in organic solvents such as ether, methanol, and ethanol. Its main components are natural organic compounds of the kaempferol type tetracyclic diterpenes, which have various pharmacological activities, especially showing significant effects in anti-tumor, anti-inflammatory, neuroprotective, and antibacterial aspects. The following is a detailed exploration of the mechanism of action of winter grass beetle extract.

1. Mechanism of anti-tumor action

 

It has shown significant activity in anti-tumor and has become a research hotspot for scholars at home and abroad. Its anti-tumor effect is mainly achieved through the following aspects:
(1) Regulating the cell cycle: G1 to S and G2 to M are the two most important stages in regulating tumor cell growth during the cell cycle. The proliferation of tumor cells can be blocked by regulating these two stages. For example, berberine can block gastric cancer cell line SGC-7901 in the G2/M phase, inhibit its proliferation, induce cell apoptosis and autophagy.

(2) Promote tumor cell apoptosis: Promote tumor cell apoptosis through various signaling pathways and mechanisms of action. It can upregulate the expression levels of endoplasmic reticulum stress-related proteins such as glucose regulated protein 78 (GRP78), phosphorylated protein kinase R-like endoplasmic reticulum kinase (p-PERK), phosphorylated eukaryotic translation initiation factor eIF2 alpha subunit (p-eIF2 alpha), and CCAAT enhancer binding protein (CHOP), and promote apoptosis of human laryngeal cancer cells Hep-2 and TU212 through the endoplasmic reticulum apoptosis pathway.

(3) Inhibiting tumor cell autophagy: Not only can it promote tumor cell apoptosis, but it can also exert anti-tumor effects by inhibiting the autophagy process of tumor cells. The specific mechanism may involve the regulation of autophagy related proteins.
(4) Inhibiting tumor cell invasion and metastasis: It can also exert its anti-tumor effect by inhibiting tumor cell invasion and metastasis. For example, reducing the migration and invasion ability of tumor cells by inhibiting the activity of matrix metalloproteinases (MMPs).

2. Anti inflammatory mechanism

 

It also exhibits significant anti-inflammatory activity, and its anti-inflammatory mechanism is mainly related to the inhibition of NF - κ B and TLR4 related signaling pathways, as well as the promotion of NLRP3 inflammasome activation.
(1) Inhibition of NF - κ B signaling pathway: NF - κ B is an important inflammatory regulatory factor involved in the occurrence and development of various inflammatory diseases. The anti-inflammatory effect can be achieved by inhibiting the activation of NF - κ B to reduce the release of inflammatory factors.

(2) Inhibition of TLR4 signaling pathway: TLR4 is the main mediator of innate immune and inflammatory responses, involved in the development of various inflammatory diseases. It can exert anti-inflammatory effects by inhibiting the overexpression of TLR4 and suppressing the activation of downstream signaling pathways such as p38 mitogen activated protein kinase (MAPK) and NF - κ B.

(3) Promote the activation of NLRP3 inflammasome: NLRP3 inflammasome is an important inflammatory regulatory complex involved in the occurrence and development of various inflammatory diseases. It can enhance the phagocytic and clearance abilities of inflammatory cells by promoting the activation of NLRP3 inflammasomes, thereby exerting anti-inflammatory effects.

3. Mechanism of neuroprotective effect

 

It also exhibits certain activity in neuroprotection, and its neuroprotective mechanism is mainly related to the inhibition of model cell apoptosis and oxidative stress.
(1) Inhibition of model cell apoptosis: It can exert neuroprotective effects by inhibiting the apoptosis of model cells. The specific mechanism may involve the regulation of apoptosis related proteins, such as inhibiting the expression of Bax protein and promoting the expression of Bcl-2 protein.

(2) Inhibiting oxidative stress: Oxidative stress is one of the important causes of neuronal damage. The damage to nerve cells can be reduced by inhibiting oxidative stress. The specific mechanism may involve the regulation of antioxidant enzymes, such as increasing the activity of superoxide dismutase (SOD) and glutathione peroxidase (GSH Px).

4. Antibacterial mechanism

 

It also has antifungal effects, especially strong synergistic effects on azole resistant fungi.
(1) Synergistic azole Drugs: When used in combination with azole drugs such as fluconazole, itraconazole, and voriconazole, it can significantly reduce the minimum inhibitory concentration (MIC) of azole drugs and promote the sensitivity of azole resistant fungi to azole drugs.
(2) Inhibition of fungal growth: Antifungal effects can be achieved by inhibiting fungal growth. The specific mechanism may involve damage to fungal cell walls or inhibition of enzyme activity within fungal cells.

5. Other pharmacological effects

 

In addition to the above-mentioned effects, it also has cardioprotective effects and inhibits the proliferation of fibroblast like synovial cells in rheumatoid arthritis.
(1) Myocardial protective effect: As an NLRP3 inhibitor, it can reduce the expression of IL-1 β and IL-18 after myocardial infarction in mice, improve myocardial fibrosis, reshape the structure of adverse myocardial cells, and achieve myocardial protection.

(2) Inhibition of fibroblast like synovial cell proliferation in rheumatoid arthritis: It can inhibit the proliferation of rheumatoid arthritis fibroblast like synovial cells (RA-FLS) and induce RA-FLS apoptosis and autophagy by increasing the expression levels of Bax and caspase-3 proteins, inhibiting Beclin-1 protein levels.

Oridonin, is a light yellow needle shaped crystal with CAS 28957-04-2 and molecular formula C20H28O6. It is a bioactive natural substance isolated from Rabdosia plants in the family Lamiaceae. Its main components are natural organic compounds of the ent kau red diterpenoid type, which are colorless prismatic crystals with an extremely bitter taste. They are insoluble in water but soluble in organic solvents such as ether, methanol, and ethanol. It has the effects of clearing heat and detoxifying, reducing swelling and dispersing nodules, promoting blood circulation and relieving pain. It is an effective ingredient extracted from winter grass, which has the effects of clearing heat and detoxifying, reducing swelling and nodules, promoting blood circulation and relieving pain. It can be used to treat diseases such as tonsillitis, pharyngitis, lymphadenitis, mumps, mastitis, gingivitis, arthritis, etc.

Ophiopogon methyl is a tetracyclic diterpenoid compound extracted and isolated from Ophiopogon japonicus, which is one of the most important Chinese herbal medicines used in clinical practice. More than half a century ago, it was confirmed that oridnin has immunomodulatory, anti-inflammatory, antiviral and other effects, especially in the treatment of upper respiratory tract infections.
Recent laboratory and clinical studies have shown that oridnin is an effective drug against transplanted tumors - prostate cancer, breast cancer, lobar lung cell cancer, etc.

Due to its susceptibility to oxidation, poor water solubility, and short biological half-life, the use of berberine as a clinical chemotherapy drug is limited. The aim of this paper is to prepare long circulating liposomes of Ophiopogon japonicus, which can prolong the retention time and increase the concentration of the drug in the blood.
This method was used to study the preparation process of long circulating liposomes of Lonicera japonica, the distribution of Lonicera japonica liposomes in mouse blood and tissues, and the anti-tumor effect of Lonicera japonica liposomes on H22 liver cancer mice.

Firstly, the extraction and purification process of arbutin from Lonicera japonica was studied. Add 12 times the amount of 95% ethanol to the powder of winter grass, and extract it three times with ultrasound for 30 minutes each time. Add 24% activated carbon with ultrasonic decolorization to the ethanol extract of winter grass twice, each time for 20 minutes.

The collected eluent from 16 minutes to 23 minutes was evaporated and concentrated, and then vacuum dried to obtain white powder of Ophiopogon japonicus. The purity was detected by high-performance liquid chromatography to be 99.0%, and the extraction rate was 65.4%.

The chemical structure of the extract was identified and validated using mass spectrometry, elemental analysis, ultraviolet, infrared, nuclear magnetic resonance, and high-performance liquid chromatography. Study on the preparation process of long circulating liposomes of Lonicera japonica and establish a high-performance liquid chromatography method for determining the content of Lonicera japonica. Using encapsulation efficiency and drug loading as indicators, the effects of the dosage of soy lecithin, cholesterol, berberine, and PEG2000-DESPE, as well as the type and volume of hydration medium, on encapsulation efficiency and drug loading were investigated.
Optimized the prescription and preparation process through experimental design:

Determine the content of winter grass beetle.

The optimal process is:

The particle size of the prepared berberine liposomes follows a normal distribution between 100nm and 200nm, with an average particle size of 150nm, an encapsulation efficiency of 95.4%, and a drug loading capacity of 4.24%.

The results of in vitro release indicate that:
The release of berberine from liposomes was almost complete after 96 hours. The confirmed prescription is good, the process is feasible, and the high performance liquid chromatography method is simple, accurate, and fast, which is conducive to controlling the quality of berberine liposomes.

The same method was used to prepare regular liposomes of berberine (without PEG_ (2000) - DSPE in the lipid membrane). The prepared long circulating liposomes and regular liposomes were stored at 5 ℃ for 80 days, and all indicators remained stable with little change in encapsulation efficiency. The results showed that the long circulating liposomes and regular liposomes of Ophiopogon japonicus had good storage stability at 5 ℃. Study the tissue distribution and pharmacokinetic characteristics of long circulating liposomes and regular liposomes of Ophiopogon japonicus in mice. High performance liquid chromatography was used to determine the concentration of oridonin in mouse blood and tissues. For long circulating liposomes and regular lipids of Ophiopogon japonicus:
A comparison was made between the distribution characteristics and pharmacokinetic parameters of body and winter grass injection in mice. Long circulating liposomes of oridnin extended the circulation time of oridnin in mice. Using the animal transplantation tumor experiment method, H22 mouse liver cancer cells were subcutaneously inoculated into Kunming mice for in vivo tumor inhibition experiments to investigate the tumor inhibition rates of long circulating liposomes, regular liposomes, and injection of oridnin on solid tumors.

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