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Product name: Ursolic acid
Synonym name: Micromerol; Formosolic acid; Forucosolic acid; Bungeolic acid; Prunol; Urson; Malol; Masterin
Catalogue No.: BP1426
Cas No.: 77-52-1
Formula: C30H48O3
Mol Weight: 456.711
Botanical Source: Eriobotrya japonica （Thunb.） Lindl.
Physical Description:
Type of Compound: Triterpenoids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.
HPLC of Ursolic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
57.5300
6.6298
5.0417
.0011
5.5621
9.2025
Low
93.1571
4.7226
No
No
No
No
No
No
0.0
No
No
Yes
No
Ursolic acid (CAS number: 77-52-1) is a pentacyclic triterpene natural product widely found in various plants, attracting attention for its diverse biological activities. As a β-hydroxyl-substituted derivative of urs-12-en-28-oic acid, ursolic acid structurally has a typical triterpene backbone, giving it unique pharmacological properties. In recent years, ursolic acid has become a hot topic in pharmacological research of natural products due to its significant anti-cancer, anti-inflammatory, antioxidant, and metabolic regulatory effects. Especially in the prevention and treatment of digestive system tumors such as colon cancer, ursolic acid has shown promising potential, with related molecular targets covering key pathways including AMPK, BCL2, STAT3, TOP1, MAPK1, TNF, PIK3CA, EGFR, PTGS2, and TP53, revealing its pharmacological basis with multiple targets and mechanisms.
This paper aims to systematically review the chemical structure and physicochemical properties of ursolic acid, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and to explore its potential value and future development trends in clinical applications, providing references for research and drug development in the field of natural product pharmacology.
Ursolic acid is a pentacyclic triterpene carboxylic acid with the chemical formula C_30H_48O_3 and a molecular weight of 456.7110. Its core structure is based on the ursane framework, specifically urs-12-en-28-OIC acid, with three carbon atoms replaced by β-hydroxyl groups. This structure imparts high hydrophobicity to ursolic acid, with a LogP value as high as 6.6298, indicating strong lipophilicity. It is poorly soluble in water (about 0.0011 mg/mL) but easily soluble in organic solvents such as ethanol and dichloromethane. Its topological pole surface area (TPSA) is 57.53 Ų, indicating moderate molecular polarity that facilitates membrane penetration.
Ursolic acid is structurally stable, presenting a typical pentacyclic triterpene backbone containing one carboxyl group and one hydroxyl group; these functional groups provide key sites for its biological activity. Its low blood-brain barrier permeability and lack of hERG channel inhibition suggest a low risk of neurological side effects. The Ames test result was negative, indicating that ursolic acid does not have significant genotoxicity.
Ursolic acid is widely found in the epiderm, leaves, fruits, and roots of various plants, especially from apple peels, rosemary, sage, honeysuckle, and bearberry leaves. Its content varies depending on the plant species, part, maturity, and growing environment. Apple peels contain a high amount of ursolic acid and are easily accessible, making them an important raw material for industrial extraction.
Traditional extraction methods mainly use organic solvent extraction methods, such as ethanol, methanol, or ethyl acetate, combined with modern technologies like ultrasound-assisted extraction and microwave-assisted extraction to improve extraction efficiency and purity. The extraction process typically includes plant crushing, solvent soaking, filtration, concentration, and purification (such as silica gel column chromatography and high-performance liquid chromatography separation). In recent years, supercritical CO_2 extraction technology has gradually been applied to ursolic acid extraction due to its green and environmentally friendly nature and strong selectivity.
During extraction and purification, controlling temperature and pH is crucial for the stability of ursolic acid, avoiding high-temperature degradation and acid-base hydrolysis. The final ursolic acid obtained is a white to pale yellow crystalline powder, with a purity usually exceeding 95%.
The pharmacological activities of ursolic acid cover multiple aspects including anticancer, anti-inflammatory, antioxidant, metabolic regulation, antibacterial, and neuroprotective effects, demonstrating broad clinical application potential.
Ursolic acid exhibits significant inhibitory effects in various tumor models, especially in colon cancer cell lines (such as HCT116, SW480), where it can induce apoptosis, block the cell cycle, and inhibit tumor cell proliferation and migration. Its mechanism of action involves regulation of multiple signaling pathways, including activation of the AMPK signaling pathway, inhibition of the STAT3 and PI3K/Akt pathways, regulation of BCL2 family protein expression, and promotion of TP53-mediated cell cycle arrest and apoptosis.
Arsolic acid reduces inflammatory responses by inhibiting PTGS2 (COX-2) expression and the release of pro-inflammatory factors such as TNF-α. Moreover, its antioxidant capacity is mainly achieved by scavenging free radicals and enhancing intracellular antioxidant enzyme activity, helping to alleviate the pathological progression of oxidative stress-related diseases.
As a natural metabolic regulator, ursolic acid can activate AMPK, promote lipid metabolism and energy balance, and show potential for anti-obesity and improvement of metabolic syndrome. It inhibits the expression of genes related to fat formation in adipose tissue, promotes fat breakdown, and helps protect cardiovascular and liver functions.
Ursolic acid also exhibits certain antibacterial, antiviral, and neuroprotective activities, can reduce neuroinflammation, promote nerve cell survival, and demonstrate its potential application value in neurodegenerative diseases.
Ursolic acid achieves its pharmacological effects through multi-target and multi-pathway regulation, and its mechanism of action has been extensively studied in the prevention and treatment of colon cancer.
AMPK, as a cellular energy sensor, is an important target for ursolic acid to regulate metabolism and inhibit tumor growth. Arsolic acid activates AMPK, promotes cellular energy metabolism balance, inhibits fat synthesis and cell proliferation, and induces autophagy and apoptosis.
Arsolic acid regulates the expression of BCL2 and its related proteins, disrupts mitochondrial membrane potentials, and promotes apoptosis. By reducing the expression of the anti-apoptotic protein BCL2, enhancing the activity of the pro-apoptotic protein BAX can induce programmed death of tumor cells.
Arsolic acid inhibits STAT3 phosphorylation and nuclear translocation, blocking its transcriptional activity, reducing the expression of tumor-promoting genes, and inhibiting tumor cell proliferation and invasion.
Ursolic acid inhibits DNA topoisomerase I, hindering DNA replication and transcription, leading to tumor cell death.
Arsolic acid regulates the MAPK signaling pathway, affects cell proliferation and differentiation, and inhibits abnormal tumor cell growth.
By regulating the expression of TNF-α, ursolic acid alleviates the inflammatory microenvironment and suppresses tumor-related inflammatory responses.
Arsolic acid inhibits the PI3K/Akt signaling pathway, blocks cell proliferation and survival signals, and promotes apoptosis.
Ursolic acid interferes with EGFR signaling, inhibiting tumor cell growth and migration.
Ursolic acid inhibits COX-2 expression, reduces the production of pro-inflammatory prostaglandins, and exerts anti-inflammatory and anti-tumor effects.
Arsolic acid activates TP53, promotes cell cycle arrest and DNA repair, and induces tumor cell apoptosis.
In summary, ursolic acid regulates tumor cell proliferation, apoptosis, migration, and the inflammatory microenvironment through multi-target synergistic effects, demonstrating a complex yet effective anti-cancer mechanism.
The druggability evaluation of ursolic acid shows that it has certain advantages and challenges.
Ursolic acid has a moderate molecular weight (456.7 Da), but its high LogP value (6.63) and extremely low water solubility (0.0011 mg/mL) limit its oral bioavailability. Its lower TPSA (57.53 Ų) favors membrane penetration, but its hydrophobicity limits its distribution in vivo.
Ursolic acid does not inhibit hERG channels, indicating a lower risk of cardiotoxicity. Ames test was negative, indicating no significant mutagenicity. Preclinical toxicology studies have shown a wide safety window and good tolerability.
Ursolic acid is poorly absorbed orally and has low bioavailability, mainly due to its hydrophobicity and low solubility. It is widely distributed in the body, but its low blood-brain barrier permeability limits its application in the central nervous system. Metabolism is mainly via the hepatic cytochrome P450 enzyme system, with metabolites including hydroxylation and glucuronic acid conjugates. Excretion mainly involves bile and feces.
To overcome low bioavailability, researchers have developed various delivery systems, such as nanoparticles, liposomes, solid dispersions, and complexes, to improve solubility and in vivo stability.
As a versatile natural product, ursolic acid shows great potential in the prevention and treatment of colon cancer and other tumors. Its multi-target mechanism provides a theoretical basis for combination therapy and multi-drug targeted therapy. Combined with modern drug delivery technologies, the bioavailability and targeting of ursolic acid are expected to be significantly improved.
Currently, clinical research on ursolic acid is still in its early stages, mainly focusing on safety evaluation and in vitro and animal model validation. In the future, pharmacokinetic research should be strengthened to clarify the optimal dosage regimen and administration. At the same time, by combining precision medicine strategies with molecular targets, the synergistic effects of ursolic acid with chemotherapy drugs or immunotherapies are being explored to promote clinical translation.
In addition, the potential applications of ursolic acid in anti-inflammatory, metabolic diseases, and neuroprotection are also worth further exploration, providing new ideas for comprehensive treatment of various chronic diseases.
As a typical pentacyclic triterpene natural product, ursolic acid has become an important subject of natural product pharmacological research due to its unique chemical structure and diverse pharmacological activities. Its multi-target mechanism of action in colon cancer and other diseases reveals the multidimensional potential of natural products to regulate diseases. Despite druggability challenges such as poor water solubility and low bioavailability, the development of modern drug delivery technology offers new possibilities for its clinical application.
In the future, by integrating multidisciplinary research combining systems pharmacology, molecular biology, and medicinal chemistry, the pharmacological mechanisms of ursolic acid will be further advanced and its clinical translation, supporting the widespread application of natural products in modern medicine. Research on ursolic acid not only broadens the pharmacological horizons of triterpene natural products but also provides valuable natural molecular templates for the development of novel anticancer and metabolic regulation drugs.
Shenshuai
Wenjing
Hedandan
