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At least 37 records · Page 2Linked to original sources
PubMed2003

Development of LC-MS method for determination of ursolic acid: application to the analysis of ursolic acid in Staphylea holocarpa Hemsl.

Ursolic acid is a hydroxy pentacyclic triterpene, which has a chemoprotective activity in human. A reliable and reproducible liquid chromatography-mass spectrometric assay (LC-MS) was developed for the determination of ursolic acid in laboratory-made mixtures and in leaves and twigs extracts of Staphylea holocarpa Hemsl. The methanolic solution of the extracted ursolic acid was chromatographically analyzed using Shim Pack CLC-CN, C18 (150 x 6 mm, 5 mu) column and a mobile consisting of methanol-1% acetic acid solution (4:1) at a flow rate of 1.0 ml min(-1). The mass spectrometer (LCQ-Finnigan) was programmed in the positive single ion monitoring (SIM) to permit detection and quantitation of ursolic acid in MS-SIM mode at m/z 439.2, 411.2 and 390.9. Linear correlation (r > 0.99) of the peak area and the concentration of ursolic acid over the concentration range 0.25-10 microg ml(-1) was obtained. The relative standard deviation (%R.S.D.) and percentage deviation from the nominal concentrations (%DEV) were found to be 3.03-3.59% and -4.5 to +6.2%, respectively. Analysis of laboratory-made mixtures containing known concentrations of ursolic acid, as quality control samples, gave a mean recovery percentage of 97.8%. Application of the proposed method for the analysis of leaves and twigs extracts of S. holocarpa Hemsl. gave mean percentage contents of ursolic acid of 0.95 and 0.25%, respectively.

Chromatography, Liquid↗
PubMed1986

Search for possible antitumor promoters by inhibition of 12-O-tetradecanoylphorbol-13-acetate-induced Epstein-Barr virus activation; ursolic acid and oleanolic acid from an anti-inflammatory Chinese medicinal plant, Glechoma hederaceae L.

From an anti-inflammatory Chinese medicinal plant, Glechoma hederaceae L., two triterpene carboxylic acids, ursolic acid (UA) and oleanolic acid (OA) have been isolated as inhibitors of 12-O-tetradecanoylphorbol-13-acetate (TPA) induced Epstein-Barr virus (EBV) activation in Raji cells. Both acids significantly inhibited the activation at a 1000-fold molar ratio to TPA, and also teleocidin B-4. The dose responses of the acids were very similar to those of the antitumor promoters, retinoic acid (RA) and glycyrrhetinic acid (GA). However, a characteristic property that UA and OA possess, far higher cell viability to the Raji cells than RA to the Raji cells, has been pointed out. Furthermore, enhancement of the inhibitory activity was found in 3-keto derivatives of UA and OA, while either loss of oxygen functionality at C-3 position of UA or oxidation at C-3 of GA led to reduction of the activity. Binding assay suggested that the inhibitory activity should be exhibited by some event caused after binding of TPA to the receptor in the cells.

Biological Assay↗
PubMed2005

The cytotoxic activity of ursolic acid derivatives.

Ursolic acid and 2alpha-hydroxyursolic acid isolated from apple peels were found to show growth inhibitory activity against four tumor cell lines, HL-60, BGC, Bel-7402 and Hela. Structural modifications were performed on the C-3, C-28 and C-11 positions of ursolic acid and the cytotoxicity of the derivatives was evaluated. The SAR revealed that the triterpenes possessing two hydrogen-bond forming groups (an H-donor and a carbonyl group) at positions 3 and 28 exhibit cytotoxic activity. The configuration at C-3 was found to be important for the activity. Introduction of an amino group increased the cytotoxicity greatly. A 3beta-amino derivative was 20 times more potent than the parent ursolic acid. The 28-aminoalkyl dimer compounds showed selective cytotoxicity.

Antineoplastic Agents, Phytogenic↗
PubMed2002

Ursolic acid as a trypanocidal constituent in rosemary.

The MeOH extract of the leaves of rosemary (Rosmarinus officinalis L.) completely inhibited the motility of cultured epimastigotes of Trypanosoma cruzi at the concentration of 2 mg/ml after 2 h of incubation. Activity-guided fractionation of the MeOH extract has resulted in the isolation of three triterpene acids, betulinic, oleanolic and ursolic acids. Ursolic acid stopped the movement of all T. cruzi epimastigotes at the minimum concentration (MC(100)) of 40 micro g/ml (88 micro M) after 48 h of incubation. Oleanolic acid was less active (MC(100): 250 micro g/ml, 550 micro M) and betulinic acid was practically inactive.

Animals↗
PubMed2001

Sterols, triterpenes and biflavonoids of Viburnum jucundum and cytotoxic activity of ursolic acid.

The triterpenes ursolic acid (1), 27-p-Z-coumaroyloxyursolic acid (2), 27-p-E-coumaroyloxyursolic acid, alpha-amyrine-3-palmitate and lupeol-3-palmitate were isolated through a bioactivity-guided fractionation from the acetonic extract of the aerial parts of Viburnum jucundum Morton in addition to amentoflavone, an epimeric mixture at C-2 of 2,3-dihydroamentoflavone, beta-sitosterol and beta-sitosteryl glucopyranoside. Ursolic acid (1) was the only constituent that exhibited cytotoxic activity toward three human cancer cell lines in culture. This is the first phytochemical and cytotoxic analysis performed to this plant species.

Antineoplastic Agents, Phytogenic↗
PubMed2004

Cardiotonic and antidysrhythmic effects of oleanolic and ursolic acids, methyl maslinate and uvaol.

The cardiotonic and antidysrhythmic effects of four triterpenoid derivatives, namely oleanolic acid (OA), ursolic acid (UA), and uvaol (UV), isolated from the leaves of African wild olive (Olea europaea, subsp. africana) as well as methyl maslinate (MM) isolated from the leaves of Olea europaea (Cape cultivar) were examined. The derivatives showed low toxicity on brine shrimp test. They displayed significant, dose-response vasodepressor effect and sinus bradicardia, most prominent for OA and MM. The derivatives acted as beta-adrenergic antagonists, blocking the effect of adrenaline and isoprenaline. The established positive inotropic and dromotropic effects were most distinctive for OA and MM. The antidysrhythmic effects were evaluated on CaCl2- and adrenaline-induced chemical arrhythmias, and on ischemia-reperfusion arrhythmia. OA and UA displayed antidysrhythmic effects on both types of chemical arrhythmia; OA and UV in dose 40 mg/kg conferred significant antidysrhythmic activity on ischemia and reperfusion arrhythmias. The effect was comparable to that of propranolol and suggestive of beta-adrenergic antagonistic activity. On the basis of the vasodepressor, cardiotonic and antidysrhythmic effects of these compounds, it was concluded that OA and UV isolated from wild African olive leaves, or crude extract containing all components, can provide a cheap and accessible source of additive to conventional treatment of hypertension, complicated by stenocardia and cardiac failure.

Animals↗
PubMed2006

Protective effects of ursolic acid and oleanolic acid in leukemic cells.

Ursolic acid (UA) and oleanolic acid (OA) have similar chemical structures but differ in the position of one methyl group on the ring E. We investigated protective effects of these two triterpenoic acids against H(2)O(2)-induced DNA damage in leukemic L1210, K562 and HL-60 cells using single-cell gel electrophoresis (SCGE). We compared their protective effects (antioxidant activities) with respect to the different position of the methyl group in their chemical structures. After 24h pre-treatment of cells both compounds investigated inhibited significantly the incidence of DNA single strand breaks induced by H(2)O(2). The concentration range of UA and OA was in all experiments 2.5-10 micromol/l. The antioxidant activity of OA determined by SCGE was significantly higher compared to UA in L1210 ((+)P<0.05) and K562 cells ((+++)P<0.001). Significant difference of the antioxidant activities of the two compounds was evidently connected with the different position of the methyl group. The protective effect of OA was in HL-60 cells slightly lower compared to the activity of UA, but the difference between the protective effects of UA and OA was not significant. In conclusion we can say that both natural pentacyclic triterpenoic acids investigated, UA and OA, manifested potent antioxidant effects. The different position of one methyl group in their chemical structures caused moderately different biological activities of these compounds on three leukemic cell lines. To explore their mechanisms of action further investigation seems to be therefore worthwhile.

Animals↗
PubMed2003

[Effects of ursolic acid on liver-protection and bile secretion].

OBJECTIVE: To study the liver-protection and promoting bile secretion of ursolic acid. METHODS: Ursolic acid was administrated to the mice with liver injury induced by CCl4 or APIT. ALT, AST levels in serum were examined. The bile flow rate and the concentration of the main components in the bile of rats administrated with ursolic acid were estimated. RESULTS: Ursolic acid could decrease the serum ALT, AST, SB levels in the mice treated with CCl4 or APIT, promote the secretion of bile and increase the concentration of bilirubin in the bile. CONCLUSION: Ursolic acid exhibited significant liver protection and promoting blie secretion.

Alanine Transaminase↗
PubMed2005

Differential gene expression for investigation of Escherichia coli biofilm inhibition by plant extract ursolic acid.

After 13,000 samples of compounds purified from plants were screened, a new biofilm inhibitor, ursolic acid, has been discovered and identified. Using both 96-well microtiter plates and a continuous flow chamber with COMSTAT analysis, 10 microg of ursolic acid/ml inhibited Escherichia coli biofilm formation 6- to 20-fold when added upon inoculation and when added to a 24-h biofilm; however, ursolic acid was not toxic to E. coli, Pseudomonas aeruginosa, Vibrio harveyi, and hepatocytes. Similarly, 10 microg of ursolic acid/ml inhibited biofilm formation by >87% for P. aeruginosa in both complex and minimal medium and by 57% for V. harveyi in minimal medium. To investigate the mechanism of this nontoxic inhibition on a global genetic basis, DNA microarrays were used to study the gene expression profiles of E. coli K-12 grown with or without ursolic acid. Ursolic acid at 10 and 30 microg/ml induced significantly (P < 0.05) 32 and 61 genes, respectively, and 19 genes were consistently induced. The consistently induced genes have functions for chemotaxis and mobility (cheA, tap, tar, and motAB), heat shock response (hslSTV and mopAB), and unknown functions (such as b1566 and yrfHI). There were 31 and 17 genes repressed by 10 and 30 microg of ursolic acid/ml, respectively, and 12 genes were consistently repressed that have functions in cysteine synthesis (cysK) and sulfur metabolism (cysD), as well as unknown functions (such as hdeAB and yhaDFG). Ursolic acid inhibited biofilms without interfering with quorum sensing, as shown with the V. harveyi AI-1 and AI-2 reporter systems. As predicted by the differential gene expression, deleting motAB counteracts ursolic acid inhibition (the paralyzed cells no longer become too motile). Based on the differential gene expression, it was also discovered that sulfur metabolism (through cysB) affects biofilm formation (in the absence of ursolic acid).

Biofilms↗
PubMed2005

Protective effect of ursolic acid on ethanol-mediated experimental liver damage in rats.

Ursolic acid is a triterpenoid that exists in nature and is the major component of some traditional medicinal herbs. In this study, ursolic acid has been evaluated for its hepatoprotective effect against chronic ethanol-mediated toxicity in rats. Ethanol administration (7.9 g/kg/day) for 60 days resulted in increased oxidative stress, decreased antioxidant defense and liver injury. It also negatively affected the serum total protein, albumin and A/G ratio. Subsequent to the experimental induction of toxicity (i.e. after the initial period of 30 days) ursolic acid treatment performed by co-administering ursolic acid (10, 20 and 40 mg/kg body weight) for 30 days along with the daily dose of ethanol. While this treatment causing a significant improvement in body weight, food intake and serum protein levels, it decreases serum aminotransferase activities (aspartate aminotransferase and alanine aminotransferase) and total bilirubin levels. Ursolic acid improved the antioxidant status of alcoholic rats, which is evaluated by the decreased levels of lipid peroxidation markers in plasma (thiobarbituric acid reactive substances and lipid hydroperoxides) and increased levels of circulatory antioxidants such as reduced glutathione, ascorbic acid and alpha-tocopherol. Histopathological observations were also in correlation with the biochemical parameters. The activity of ursolic acid (20 mg/kg) compares well with silymarin, a known hepatoprotective drug, and seems to be better in certain parameters. The protective effect of ursolic acid is probably related to its antioxidant activities.

Animals↗
PubMedDate not supplied

Cytostatic, cytotoxic and protein tyrosine kinase inhibitory activity of ursolic acid in A431 human tumor cells.

The effect of the tritepene, ursolic acid, on the proliferation of A431 human epidermoid carcinoma cells was studied. According to our investigations, ursolic acid is a potent inhibitor of A431 cell growth. Ursolic acid markedly reduced A431 cell growth in a time- and dose-dependent manner. We found a good correlation between the results of direct cell counting and the MTT test. During long periods of drug exposure, ursolic acid exhibited both cytotoxic and cytostatic activity. The effect was partially reversible on drug removal. The greatest cytotoxicity was observed both in the trypan blue test and in the MTT test at 50 mM. Investigations on tyrosine kinase inhibition were performed by biochemical and cellular assays on A431 cells. Ursolic acid inhibited tyrosine kinase activity of A431 cells in biochemical assay in a dose-dependent manner with an IC50 of 24 mM. In cellular assay, when A431 cells were pretreated with ursolic acid for 24, 48 and 168 hours at various concentrations (5, 10, 20, 30 and 50 mM), lower values of IC50 were measured: 6.8 microM for 24 hours, 5.2 mM for 48 hours and 1.4 mM for 168 hours. The results suggest that ursolic acid exerts an antiproliferative effect through the inhibition of tyrosine kinase enzymes.

Antineoplastic Agents, Phytogenic↗
PubMed2003

In vivo anti-nociceptive and anti-inflammatory effect of the two triterpenes, ursolic acid and 23-hydroxyursolic acid, from Cussonia bancoensis.

Triterpenoids, ursolic acid (1) and 23-hydroxyursolic acid (2) were obtained from the hydrolysis of BuOH fraction of Cussonia bancoensis extract to test antinociceptive and anti-inflammatory effect of C. bancoensis (Araliaceae). Compound 1 and 2 exhibited anti-nociceptive effects, which were determined by acetic acid-induced writhing test and hot plate test. The effect of 2 was much more potent in acetic acid-induced writhing test than in hot plate test. Compound 1 and 2 significantly inhibited 1%-carrageenan-induced edema in the rat. These results suggest that the two triterpenes, ursolic acid and 23-hydroxyursolic acid, are responsible for the anti-nociceptive and anti-inflammatory effect of C. bancoesnsis.

Analgesics↗
PubMed2004

Effects of ursolic acid on different steps of the angiogenic process.

Ursolic acid is a triterpenoid with pleiotropic biological effects. In this report, we study the effects of ursolic acid on different key steps of angiogenesis. Our results show that ursolic acid is able to inhibit key steps of angiogenesis in vitro, including endothelial cell proliferation, migration, and differentiation. At the same time, it seems to stimulate other key steps of angiogenesis, such as extracellular matrix degradation by MMP-2 and urokinase. Although ursolic acid can inhibit in vivo angiogenesis in the CAM assay, the different signs of the effects it causes on different steps of angiogenesis force one to be cautious concerning its anti-angiogenic potential.

Animals↗
PubMedDate not supplied

Activation of caspase-3 protease during the process of ursolic acid and its derivative-induced apoptosis.

The apoptosis-inducing effect of the triterpene saponins, namely, ursolic acid and its natural derivative, methyl-ursolate beta-D-glucoside on A431 human epidermoid carcinoma cells was studied. The cells treated with 5-50 microg/ml of ursolic acid resulted in a dose- and time-dependent decrease in cell number, due to an increase of apoptotic cells as evidenced by MTT assay together with morphological changes. The highest dose (50 microg/ml) of ursolic acid resulted in approximately 90% inhibition in tumor cell growth after 96 hours of treatment and 60% of apoptosis after 48 hours. To the contrary, when the same treatment was carried out with methyl-ursolate beta-D-glucoside, after 96 hours of treatment the percentage of cell growth inhibition was found to be only 30% at the dose of 50 microg/ml and the value of apoptosis did not exceed 10%. Similarly to these results, ursolic acid effectively induced proteolytic activation of caspase-3 protease in a dose-dependent manner while its derivative showed only weak activity in this enzyme assay. The addition of DEVD-CHO prior to ursolic acid and methyl-ursolate beta-D-glucoside treatment effectively prevented the loss of triterpenes-induced viability. In summary, the triterpene saponins investigated contain an apoptotic-inducing activity in A431 cells and in the case of ursolic acid it is associated with proteolytic activation of caspase-3 and/or other similar caspases. Our results also indicated that methylation of COOH-28 together with the glycosylation of C3 of ursolic acid have a strong impact on its antitumor activity.

Apoptosis↗
PubMed1992

Effect of ursolic acid from epicuticular waxes of Jacaranda decurrens on Schizaphis graminum.

Ursolic acid from Jacaranda decurrens showed toxicity and feeding deterrency towards the greenbug Schizaphis graminum. Biological activity was determined by analyzing ursolic acid effects on the survival, reproductive index, and population growth rate of the greenbug. Survival and reproductive index decreased in direct proportion to ursolic acid content in the diet. The population growth rate decreased markedly when the aphids were fed on barley leaves sprayed with ursolic acid dissolved in DMSO, in comparison to leaves sprayed only with DMSO. The feeding behavior of the greenbug was also affected by ursolic acid. Ingestion time on diet with 0.1 mM was reduced about 30% in relation to the ingestion time on control diet.

Animals↗