Product Name: Anemosapogenin
Synonym name: 23-Hydroxybetulinic acid
Catalogue No.: BP0168
Cas No.: 85999-40-2
Formula: C30H48O4
Mol Weight: 472.71
Botanical Source: Paeonia japonica, Anemone chinensis and Pulsatilla chinensis
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
23 Hydroxybetulinic acid (CAS number: 85999-40-2) is a natural triterpenoid compound that has received widespread attention in the field of pharmacology due to its unique biological activity. As a hydroxyl derivative of betulinic acid, 23 hydroxybetulinic acid has high structural modification, endowing it with excellent pharmacological properties and potential clinical application value. In recent years, with the deepening of pharmacological research on natural products, 23 hydroxybetulinic acid has gradually become one of the important candidate molecules for the development of anti-tumor drugs due to its significant anti-cancer activity.
This review will systematically elucidate the chemical structure and physicochemical properties, plant sources, and extraction methods of 23 hydroxybetulinic acid, with a focus on its pharmacological activity and mechanism of action. Combined with drug parameters and pharmacokinetic characteristics, it will explore its clinical application prospects and future development directions, aiming to provide theoretical basis and practical guidance for related research.
23 hydroxybetulinic acid belongs to the pentacyclic triterpenoid class, with a molecular formula of C30H48O4 and a molecular weight of 472.7. Its structure is based on the five ring skeleton of betulinic acid, with hydroxyl modification introduced at the 23rd carbon position to form a 23 hydroxyl substituent, increasing the polarity and hydrogen bond donor ability of the molecule. This structural feature not only affects its biological activity, but also has a significant impact on its pharmacokinetic properties.
In terms of physicochemical properties, the LogP value of 23 hydroxybetulinic acid is 4.2, indicating its good lipid solubility, which is beneficial for transmembrane absorption but may limit water solubility. The polar surface area (TPSA) is 77.76 Å ², indicating that its molecules have moderate polarity that facilitates binding to biological targets. The molecule contains four hydrogen bond receptors, enhancing its binding affinity with protein receptors. According to the blood-brain barrier permeability assessment, the penetration ability of 23 hydroxybetulinic acid is relatively low, indicating its limited distribution in the central nervous system. Toxicological indicators show that it has no hepatotoxicity, cardiotoxicity, or hERG channel inhibition, and the Ames test is negative, indicating its high safety and good potential for drug development.
23 hydroxybetulinic acid mainly comes from various plants, especially the hydride metabolites of lupinus spp. As a leguminous plant, lupine contains abundant triterpenoids and their derivatives, providing a natural source of 23 hydroxybetulinic acid. In addition to lupine, this compound can also be detected in some white birch plants and other plants rich in triterpenoids, but the content is relatively low.
The extraction method generally adopts organic solvent extraction combined with column chromatography separation technology. Common extraction solvents include ethanol, methanol, and ethyl acetate, which utilize their good solubility for triterpenoids. The extraction process usually includes drying and crushing plant materials, solvent extraction, concentration, liquid-liquid distribution, and purification by silica gel column chromatography. In recent years, ultrasound assisted extraction and supercritical CO2 extraction techniques have gradually been applied to the extraction of this compound, improving extraction efficiency and purity while reducing the use of organic solvents, in line with the concept of green chemistry.
The pharmacological activity research of 23 hydroxybetulinic acid mainly focuses on its anti-cancer effect, and also involves anti-inflammatory, antiviral, and immune regulation aspects.
A large number of in vitro cell experiments and in vivo animal model studies have confirmed that 23 hydroxybetulinic acid has a significant inhibitory effect on a variety of tumor cells, including but not limited to lung cancer, breast cancer, liver cancer, colorectal cancer and melanoma cells. Its anti-tumor effect is manifested by inhibiting cell proliferation, inducing cell apoptosis, blocking cell cycle, and inhibiting tumor metastasis.
Specifically, 23 hydroxybetulinic acid can induce tumor cell apoptosis by activating the mitochondrial pathway, regulate Bcl-2 family protein expression, promote cytochrome C release, and activate the caspase cascade reaction. In addition, the compound can inhibit the invasion and migration ability of tumor cells, reduce the activity of matrix metalloproteinases (MMPs), and block signal transduction in the tumor microenvironment.
23 hydroxybetulinic acid exhibits good anti-inflammatory activity in an inflammatory model. By inhibiting the NF - κ B signaling pathway and downregulating the expression of pro-inflammatory factors such as TNF - α and IL-6, the inflammatory response is alleviated. Its immune regulatory effect is reflected in regulating macrophage function and promoting anti-tumor immune response, enhancing the body's immune surveillance of tumors.
Some studies have shown that 23 hydroxybetulinic acid has inhibitory effects on certain viruses, which may be achieved by interfering with the virus replication cycle or enhancing the host immune response, but the relevant mechanisms still need to be further explored.
The anticancer mechanism of 23 hydroxybetulinic acid is complex, involving multiple signaling pathways and molecular targets.
This compound promotes the loss of mitochondrial membrane potential by regulating the Bcl-2/Bax ratio, leading to the release of cytochrome C into the cytoplasm, activation of caspase-9 and caspase-3, and ultimately triggering cell apoptosis. This pathway is the core mechanism by which it induces programmed cell death in tumor cells.
23 hydroxybetulinic acid can inhibit I κ B α phosphorylation, prevent NF - κ B nuclear translocation, reduce the expression of pro-inflammatory factors and anti apoptotic genes, and inhibit the survival and proliferation of tumor cells.
This compound downregulates the phosphorylation levels of PI3K and Akt, inhibits mTOR signaling, leads to cell cycle arrest and apoptosis, and hinders the growth and metabolism of tumor cells.
By inhibiting the expression and activity of MMP-2 and MMP-9, 23 hydroxybetulinic acid reduces tumor cell matrix degradation, inhibits cell migration and invasion, and blocks the process of tumor metastasis.
The study also suggests that it may exert anti-tumor effects by regulating ROS levels, activating p53 signaling, and affecting cellular autophagy pathways, but the specific mechanism needs further clarification.
The pharmacological evaluation of 23 hydroxybetulinic acid shows that it has good potential for drug development. The molecular weight of 472.7 conforms to Lipinski's rule, and although the LogP value of 4.2 is high, it is still within an acceptable range, indicating that its lipophilicity is moderate and conducive to cell membrane penetration. The TPSA is 77.76 Å ², which supports its good bioavailability.
Toxicological evaluation shows that the compound has no hepatotoxicity or cardiotoxicity, and does not exhibit hERG channel inhibition or genotoxicity, indicating high safety. The low permeability of the blood-brain barrier suggests a lower risk of central nervous system side effects.
In terms of pharmacokinetics, existing research is relatively limited. In vivo experiments have shown that 23 hydroxybetulinic acid is well absorbed orally, but its bioavailability is limited by its poor water solubility. Its metabolism is mainly through the liver enzyme system, involving oxidation and hydroxylation reactions. The main excretion pathways are bile and urine. In the future, it is necessary to improve its stability and in vivo half-life through structural modification and pharmaceutical optimization.
23 hydroxybetulinic acid has shown broad clinical application prospects due to its significant anti-cancer activity and good safety. As an anti-tumor candidate drug derived from natural products, it has potential advantages in the treatment of lung cancer, breast cancer and other solid tumors. Especially in combination chemotherapy and targeted therapy, 23 hydroxybetulinic acid may exert a synergistic effect, reducing the toxic side effects of chemotherapy drugs.
Future research should focus on the following directions:
Pharmacokinetic and pharmacodynamic studies Systematically evaluate its absorption, distribution, metabolism, and excretion characteristics in the body, and optimize the dosing regimen.
Structural modification and pharmaceutical optimization Improving water solubility and bioavailability through chemical modification, developing nanocarriers and sustained-release formulations, and enhancing therapeutic efficacy.
Deepening mechanism research Reveal its multi-target mechanism of action and explore its potential for combined application with immunotherapy and gene therapy.
Preclinical and clinical trials Conduct systematic toxicological evaluations and clinical trials to verify its safety and efficacy, and promote its clinical translation.
Expansion of indications for multiple diseases In addition to anti-tumor effects, explore its potential applications in anti-inflammatory, antiviral, and immune regulation fields.
23 hydroxybetulinic acid, as a structurally unique and biologically active triterpenoid natural product, exhibits significant anti-cancer potential and good safety. Its multi-target and multi mechanism characteristics provide new ideas for the development of natural anti-tumor drugs. Although research on its pharmacokinetics and clinical applications is still in its infancy, with advances in medicinal chemistry, molecular biology, and pharmaceutical technology, 23 hydroxybetulinic acid is expected to become an important breakthrough in the development of anticancer drugs. Future systematic research and clinical validation will lay a solid foundation for its widespread application, promoting the development and innovation of natural product pharmacology.
