Betulonic acid is mainly extracted from birch bark; it can also be obtained by chemical synthesis using betulin as raw material. Alias betulinic acid, natural lupine-type pentacyclic triterpenoids. Chemical name 3β-hydroxy-lup-20(29)-ene-28-oic acid [4], molecular formula C30H48O3, molecular weight 456.71, CAS number 472-15-1, boiling point 550.0±33.0 °C (Predicted), acidity coefficient ( pKa)4.61±0.70(Predicted), density 1.065±0.06 g/cm3(Predicted) , it is a white powder with slight gas and bitter taste. It was first discovered in the bark of Rhamnaceae evergreen plants growing in East Africa in the 1990s.
In the mid-1990s, it was discovered that betulinic acid can selectively kill human melanoma cells without killing healthy cells; Betulinic acid is clinically inhibitory to HIV-1 infection. It also has an inhibitory effect on malignant tumor cells such as brain tumors, neuroectodermal tumors, and leukemia, and is widely used in the field of medicine and health care.
Betulinic acid (English: Betulinic acid, also known as betulinic acid, betulinic acid, epi-betulinic acid) is a natural lupine-type pentacyclic triterpene compound with antiretroviral activity, antimalarial activity and Anti-inflammatory activity, recently reported to have anti-cancer activity by inhibiting topoisomerase, was first found in some species of Betula, such as the bark of Betula pubescens (Betula pubescens), hence the name.
Betulinic acid is insoluble in water, slightly soluble in methanol, ethanol, acetone, easily soluble in tetrahydrofuran and pyridine.
CAS Number |
472-15-1 |
Molecular Weight |
456.700 |
Density |
1.1±0.1 g/cm3 |
Boiling Point |
550.0±33.0 °C at 760 mmHg |
Molecular Formula |
C30H48O3 |
Melting Point |
295-298 °C (dec.)(lit.) |
Common Name |
Betulinic acid |
Flash Point |
300.5±21.9 °C |
Product name |
Betulinic acid |
Extract source |
Birch bark |
Extraction Solvent |
Ethyl alcohol |
Appearance |
White crystalline powder |
Solubility |
Soluble in: chloroform, ethanol, acetone, methanol, ether; very slightly soluble in: benzene |
Identification |
HPLC |
Sulphated Ash |
NMT 0.5% |
Heavy metals |
NMT 20 PPM |
Loss On Drying |
NT 5.0% |
Powder size |
80Mesh, NLT90% |
Assay of Betulinic acid (HPLC test, percent, Standard in House) |
Min. 95.0% |
Residual Solvents |
|
- N-hexane |
NMT 290 PPM |
- Methanol |
NMT 3000 PPM |
- Acetone |
NMT 5000 PPM |
- Ethyl Acetate |
NMT 5000 PPM |
- Ethanol |
NMT 5000 PPM |
Pesticide Residues |
|
- Total DDT (Sum of p,p'-DDD,P,P'-DDE,o,p'-DDT and p,p' -DDT) |
NMT 0.05 PPM |
- Aldrin, Endrin, Dieldrin |
NMT 0.01 PPM |
Microbiological Quality (Total viable aerobic count) |
|
- Bacteria, CFU/g, not more than |
NMT 103 |
- Moulds and yeasts, CFU/g, not more than |
NMT 102 |
- E.coli, Salmonella, S. aureus, CFU/g |
Absence |
Storage |
In Tight, Light-resistant and Dry Place. Avoid Direct Sunshine. |
Shelf life |
24 months |
First, it is extracted and isolated from natural plants. This method consumes a large amount of solvent, the yield is low, and the impurities are not easy to separate, so it is rarely used; second, betulin is used as a precursor to obtain betulinic acid through organic synthesis. This method has been applied in industrial production, and industrial-scale betulinic acid can be obtained, which is the main source of betulinic acid in the market; thirdly, betulin is used as a precursor to produce betulinic acid through microbial transformation. This method represents a new direction for the plant extraction industry in the future, but there are still many technical problems that cannot be solved.
Betulinic acid was first discovered to have strong selective cytotoxicity to melanoma cells. In recent years, it has also been found to have strong broad-spectrum activity on other tumor cells. Tube cell tumor, Ewing tumor and other malignant tumors, colon cancer, breast cancer, lung cancer, liver cancer, prostate cancer, renal cell, ovarian or cervical cancer and leukemia have strong inhibitory effect.
1) Anti tumor effect of Betulonic Acid
Betulinic acid was first found to have extremely strong selective cytotoxicity to melanoma cells. In recent years, it has also been found to have strong broad-spectrum activity to other tumor cells, such as glioblastoma, neuroblastoma, neuroblastoma, ewing tumor and other malignant tumors, colon cancer, breast cancer, lung cancer, liver cancer, prostate cancer, kidney cell Ovarian or cervical cancer and leukemia have strong inhibitory effects.
2) Anti inflammatory effect
Most pentacyclic triterpenes have anti-inflammatory activities. Both betulin and betulinic acid have mild anti-inflammatory properties at higher concentrations, and their anti-inflammatory properties may depend on their inhibition of protein kinase C, without involving any neurogenic inflammatory mechanisms. There are also studies indicating that its activity is the result of interaction with glucocorticoid receptors.
The anti-inflammatory effect of betulinic acid has been verified in vitro and in vivo model systems. Betulinic acid can inhibit the production of PGE2 and alleviate inflammatory reactions.
3) Bacteriostatic effect
It has been found that betulinic acid has a certain antibacterial effect, which can inhibit a variety of bacteria including Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Staphylococcus epidermidis. However, studies have shown that its antibacterial activity is weak, which may be related to its belonging to lupine pentacyclic triterpenes, its structure is similar to that of hopane pentacyclic triterpenes, and the presence of substances on the bacterial membrane that can biosynthetically synthesize hopane pentacyclic triterpenes. Based on the existing research on the antibacterial ability of betulinic acid, its potential as an antibacterial agent is small.
4) Antiviral effect
Betulinic acid has prominent antiviral activity, especially HIV activity, and has effective effects on anti hepatitis C virus, anti herpes simplex virus, anti Eico virus, and anti influenza virus.
5) Anti hyperlipidemic effect
Some studies have found that betulinic acid and its derivatives can play an anti hyperlipidemic role by regulating adipokines, reducing lipid production, and reducing the levels of triacylglycerol and total cholesterol.
6) Anti diabetes effect
Betulinic acid shows good efficacy in the treatment of diabetes, mainly through inhibition α- Amylase and α- Glucosidase can reduce the hydrolysis of polysaccharides and promote glycogen synthesis.
7) Antioxidant stress activation
BA has a protective effect on normal cells and the body, which is related to antioxidant stress. For example, betulinic acid has protective effects on ischemia reperfusion injury in the brain, kidneys, and heart. BA has protective effects on cerebral ischemia reperfusion injury in mice through antioxidant stress, anti nitrogen stress, and increased blood flow.
8) Other diseases
There are also some studies that have found that betulinic acid has a certain improvement effect on Alzheimer's disease. Its protective effect is mainly through reducing neurobehavioral and cognitive dysfunction, reducing proinflammatory cytokines in the hippocampus, and reducing oxidation and nitrification reactions.
At the same time, there are also literature reports that betulinic acid has certain anti anxiety effects, and some anti anxiety drugs have already used the betulinic acid component. This may be related to the high fat solubility of betulinic acid, which can penetrate the brain barrier.
Application:
BA is a very valuable natural product. As biological agents, BA and its derivatives have shown great potential in anti-cancer and HIV treatment, and play an important role in the body's anti-oxidative damage and immune regulation process, and are a class of promising drug lead compounds. It is of great value for the research and development of new drugs, and the NCI of the American Cancer Institute has included it in the Rapid Research and Development Program (RAID).
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