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Synonym name:
Catalogue No.: BP0068
Cas No.: 4339-72-4
Formula: C32H50O4
Mol Weight: 498.748
Botanical Source: Fairly widespread in plants
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.
HPLC of 3-O-acetyloleanolic acid
HNMR of 3-O-acetyloleanolic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
63.6000
6.8000
Low
Unknown
Unknown
Unknown
Unknown
No
Unknown
3-O-acetyloleanolic acid (CAS No.: 4339-72-4) is a natural olean alkyd product isolated from the seeds of the plant Vigna sinensis K. As a derivative of oleanolic acid compounds, 3-O-acetyloleanolic acid has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse biological activity. Previous studies have shown that this compound has significant anti-angiogenic effects, capable of dose-dependent inhibition of human umbilical vein endothelial cell (HUVEC) proliferation, migration, and tubular formation. Additionally, 3-O-acetyloledanolic acid demonstrated the ability to inhibit vascular endothelial growth factor A (VEGF-A)-induced lymphangiogenesis and lymph node metastasis in animal models of oral squamous cell carcinoma. More importantly, this compound also demonstrated potential in regulating blood glucose levels, significantly lowering blood glucose in streptozozotin (STZ)-induced diabetic rat models, suggesting its potential in the treatment of hyperglycemia and diabetes. This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application potential of 3-O-acetyloleanolic acid, aiming to provide a theoretical basis and research direction for its further development.
3-O-Acetyl-oledanolic acid is an acetylated derivative of oledanulic acid with a molecular formula of C32H50O5 and a molecular weight of 498.70. Structurally, 3-O-acetyloledanolic acid introduces an acetyl group (-COCH3) at the hydroxyl site 3 of oleanolic acid, a modification that not only affects its polarity and lipid solubility but may also alter its binding affinity with biological targets. The compound has a LogP value of 6.8, indicating high lipid solubility, indicating good cell membrane penetration but may also face challenges in bioavailability and solubility. Its topological pole surface area (TPSA) is 63.6 Ų, and the number of hydrogen bond acceptors is 4, indicating certain polar characteristics in intermolecular interactions. The blood-brain barrier has low permeability, suggesting its limited distribution in the central nervous system. Regarding safety indicators such as hepatotoxicity, cardiotoxicity, hERG channel inhibition, and genotoxicity (Ames test), there are currently no detailed reports and further systematic evaluation is needed.
3-O-Acetyloleanodelic acid is mainly extracted from the seeds of the leguminous plant Vigna sinensis K. Vigna sinensis is widely distributed in tropical regions of Asia and Africa and is an important food and feed crop. Its seeds are rich in various triterpene compounds, especially oleanolic alkyd and its derivatives. During extraction, organic solvents such as ethanol, methanol, or ethyl acetate are typically used for extraction and extraction, followed by liquid-liquid separation and column chromatography (silica gel, C18 reversed phase column) for separation and purification. High-performance liquid chromatography (HPLC) and mass spectrometry (MS) technologies are commonly used for component identification and purity testing. Acetyl-modified 3-O-acetyloledanolic acid can be obtained by chemical acetylation or directly isolated from natural extracts. In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, laying the foundation for large-scale production.
One of the most notable pharmacological activities of 3-O-acetyloledanolic acid is its anti-angiogenesis ability. In vitro experiments showed that this compound inhibited the proliferation, migration, and tubular structure formation of human umbilical vein endothelial cells (HUVEC) in a dose-dependent manner, with a key step that blocked the formation of neovascular tumors. In vivo animal models, especially in oral squamous cell carcinoma models, 3-O-acetyloledanolic acid effectively inhibited VEGF-A-induced lymphangiogenesis and lymph node metastasis, significantly slowing tumor progression. These results indicate its potential application value in anti-tumor therapy, especially in inhibiting tumor metastasis and invasion.
In addition to anti-angiogenesis, 3-O-acetyloledanolic acid can also induce apoptosis in various cancer cell lines. Its mechanism of inducing apoptosis involves mitochondrial pathway activation, cell cycle arrest, and upregulation of pro-apoptotic protein expression. Relevant studies have shown that this compound exhibits certain cytotoxicity against oral cancer, liver cancer, and lung cancer cells, suggesting its potential as a candidate molecule for antitumor drugs.
Research on 3-O-acetyloledanolic acid in metabolic diseases is also gradually underway. In STZ-induced diabetic rat models, oral 3-O-acetyloledolanolic acid significantly lowered blood glucose levels and improved glucose metabolism disorders. This compound may act by modulating the AMPK signaling pathway, inhibiting the activity of the glucose transporter SGLT2, and influencing insulin sensitivity-related targets. Additionally, it may regulate molecules such as EHMT2, UBP2, and PAI1, which are related to glucose metabolism and inflammation, thereby alleviating diabetes-related complications.
The multi-target mechanism of 3-O-acetyloledanolic acid forms the basis for its pharmacological diversity. The anti-angiogenic effect mainly works by inhibiting the VEGF-A signaling pathway, blocking the proliferation and migration of endothelial cells, and suppressing angiogenesis and lymphangiogenesis. The specific mechanism may involve downregulating VEGFR-2 expression, inhibiting the PI3K/Akt and MAPK signaling pathways, thereby reducing the secretion of pro-angiogenic factors.
In terms of antitumor activity, 3-O-acetyloledanolic acid induced cancer cell apoptosis is closely related to mitochondrial membrane potential loss and activation of caspase families (such as caspase-3 and caspase-9). Additionally, it can regulate the expression of Bcl-2 family proteins, promote upregulation of the pro-apoptotic protein Bax, and inhibit the anti-apoptotic protein Bcl-2, thereby inducing programmed cell death.
For hyperglycemia, 3-O-acetyloledanolic acid modulates several key targets, including:
The synergistic regulation of these targets enables 3-O-acetyloledolic acid to demonstrate multiple effects in improving glucose metabolism and preventing and treating diabetic complications.
Druggability analysis of 3-O-acetyloledanolic acid showed that its high lipophilic solubility (LogP=6.8) favors cell membrane penetration but may result in poor water solubility, affecting oral bioavailability. TPSA is 63.6 Ų, and moderate polarity helps molecules bind to targets. The number of hydrogen bond receptors is 4, meeting some requirements of the Lipinski rule, but the overall molecular weight is close to 500, indicating the need to pay attention to pharmacokinetic properties.
The low permeability of the blood-brain barrier indicates limited distribution in the central nervous system, which may reduce central side effects but restrict its application in neurological diseases. Safety indicators such as hepatotoxicity, cardiotoxicity, and hERG channel inhibition remain unclear and require further evaluation through in vivo and in vitro trials. Genotoxicity (Ames test) data is lacking, and safety evaluation still needs improvement.
In terms of pharmacokinetics, there is currently a lack of systematic data on in vivo absorption, distribution, metabolism, and excretion (ADME). Given its high lipid solubility, there may be issues with first-pass effects and metabolic stability. Future research should focus on formulation optimization, improving solubility and bioavailability, as well as clarifying metabolic pathways and potential drug interactions.
3-O-Acetyloledanolic acid, with its multiple pharmacological activities including anti-angiogenesis, anti-tumor, and hypoglycemic effects, demonstrates broad clinical application potential. In the field of tumor treatment, especially for oral squamous cell carcinoma and other solid tumors, its ability to inhibit tumor neovascularization and lymphatic metastasis offers new ideas for anti-tumor drug development. Combined with its ability to induce cancer cell apoptosis, 3-O-acetyloledinalic acid is expected to be a candidate molecule for monotherapy or combination therapy.
In the field of metabolic diseases, 3-O-acetyloledenalic acid modulates blood glucose metabolism through multiple targets, offering a potential new strategy for the treatment of diabetes and its complications. In the future, modern drug design technologies can be combined to optimize pharmacokinetic properties, improve oral bioavailability, and further promote clinical translation.
However, current research mostly focuses on in vitro and animal models, lacking systematic preclinical safety evaluations and human trial data. In the future, toxicological research should be strengthened to clarify the safety and potential side effects of long-term medication. At the same time, in-depth analysis of its molecular mechanisms and target networks will help accurately target indications and guide clinical applications.
3-O-Acetyloledanolic acid, as a natural triterpenoid compound derived from Vigna sinensis K. seeds, demonstrates promising drug development potential due to its unique chemical structure and diverse biological activities. Its anti-angiogenesis, anti-tumor, and hypoglycemic effects offer new possibilities for treating various diseases. Although there are still challenges in druggability, safety, and pharmacokinetics, with advances in extraction and purification techniques, structural modification strategies, and pharmacological mechanism research, 3-O-acetyloledanolic acid is expected to become an important candidate molecule in the development of natural product drugs. Future research should focus on systematic preclinical evaluation, mechanism analysis, and formulation optimization to promote their translation into clinical applications and benefit patients.
Shenshuai
Wenjing
Hedandan
