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At least 19 recordsLinked to original sources
PubMed2003

Effect of naturally occurring triterpenoids glycyrrhizic acid, ursolic acid, oleanolic acid and nomilin on the immune system.

The effect of naturally occurring triterpenoid compounds such as glycyrrhizic acid, ursolic acid, oleanolic acid, and nomilin on the immune system was studied using Balb/c mice. Intraperitoneal treatments with 5 doses of these terpenoid compounds were found to enhance the total white blood cells (WBC) count. In ursolic acid, oleanolic acid and nomilin treated animals the maximum total WBC count was observed on the 6th day, while in glycyrrhizic acid treated animals it was observed only on the 9th day after the drug treatment. In ursolic acid, oleanolic acid and nomilin treated animals the percentage of increase in the total WBC count was to 91.48 +/- 4.6%, 135.75 +/- 6.4% and 117.33 +/- 17.9% respectively. In the glycyrrhizic acid treated animals the total WBC count was increased to 114.9 +/- 18%. Bone marrow cellularity and alpha-esterase positive cells were also enhanced by the treatment with these terpenoids. Treatment with various triterpenoids along with antigen produced an enhancement in the specific antibody titre and the number of plaque forming cells (PFC) in the spleen. Triterpenoids remarkably inhibited delayed type hypersensitivity reaction (DTH). These results indicate the immunomodulatory activity of naturally occurring triterpenoids such as glycyrrhizic acid, ursolic acid, oleanolic acid and nomilin.

Animals↗
PubMed2003

Inhibition of ultraviolet-A-modulated signaling pathways by asiatic acid and ursolic acid in HaCaT human keratinocytes.

Premature aging of the skin (photoaging) is a well-documented consequence of exposure to ultraviolet-A (UVA). Enhanced generation of reactive oxygen species and induction of matrix metalloproteinases (MMPs) appear to be the most important components of UVA-modulated signal transduction pathways, ultimately leading to photoaging. In this study, we investigated the effects of asiatic acid and ursolic acid, triterpene compounds, on the UVA-modulated signaling pathways using HaCaT human keratinocytes as a model cellular system. In the cells, we confirmed that UVA irradiation induced oxidative stress and increased the expression of MMP-2. Asiatic acid and ursolic acid significantly suppressed the UVA-induced reactive oxygen species production and lipid peroxidation. Pretreatment with asiatic acid or ursolic acid significantly reduced the UVA-induced activation and expression of MMP-2. In addition, UVA-induced enhanced expression of p53, a hallmark of UV-induced DNA damage and cell death, was also significantly inhibited by pretreatment with asiatic acid or ursolic acid. Taken together, these results suggest that asiatic acid and ursolic acid may be an effective inhibitor of UVA-modulated signal transduction pathways in human skin cells. These results further suggest that these agents may be useful in the prevention of UVA-induced photoaging.

Cell Survival↗
PubMed1995

Pharmacology of oleanolic acid and ursolic acid.

Oleanolic acid and ursolic acid are triterpenoid compounds that exist widely in food, medicinal herbs and other plants. This review summarizes the pharmacological studies on these two triterpenoids. Both oleanolic acid and ursolic acid are effective in protecting against chemically induced liver injury in laboratory animals. Oleanolic acid has been marketed in China as an oral drug for human liver disorders. The mechanism of hepatoprotection by these two compounds may involve the inhibition of toxicant activation and the enhancement of the body defense systems. Oleanolic acid and ursolic acid have also been long-recognized to have antiinflammatory and antihyperlipidemic properties in laboratory animals, and more research is warranted to develop a therapy for patients. Recently, both compounds have been noted for their antitumor-promotion effects, which are stimulating additional research in this field. Oleanolic acid and ursolic acid are relatively non-toxic, and have been used in cosmetics and health products. The possible mechanisms for the pharmacological effects and the prospects for these two compounds are discussed.

Antineoplastic Agents, Phytogenic↗
PubMed2003

MECC determination of oleanolic acid and ursolic acid isomers in Ligustrum lucidum Ait.

In this paper, a novel method to separate and determine oleanolic acid and ursolic acid isomers in Ligustrum lucidum Ait was studied by micellar electrokinetic capillary chromatography (MECC). The baseline separation of the two analytes were obtained on the condition that the buffer contained 15 mmol/l disodium hydrogen phosphate, 15 mmol/l disodium tetreborate, 10 mmol/l SDS and 5% (v/v) alcohol. The contents of the oleanolic acid and ursolic acid were determined in L. lucidum Ait, Folium photiniae and Flos campsis; they were 78.3 (R.S.D. = 2.75%) and 20.7 mg/g (R.S.D. = 2.97%), 27.9 (R.S.D. = 3.67%) and 79.8 mg/g (R.S.D. = 3.44%), 65.5 (R.S.D. = 3.73%) and 60.4 mg/g (R.S.D. = 4.06%) (n = 5), respectively. The recoveries of the analytes in the extract of L. lucidum Ait were 102%, (R.S.D. = 2.85%) for oleanolic acid and 104% (R.S.D. = 3.21%) for ursolic acid (n = 5). With the emphasis on the effects of SDS and alcohol concentrations on the separation of the isomers were investigated.

Algorithms↗
PubMed1999

[Determination of oleanolic acid and ursolic acid in spica Prunellae by derivative GC method].

OBJECTIVE: To develop a GC method to determine the oleanolic acid and ursolic acid in Spica Prunellae. METHOD: Before GC analysis, the sample was derivatized with CH2N2 solution. The GC conditions were as follows: comumn-10% SE-30(2m x 3mm) and column temperature -270 degrees C. RESULT: The two constituents were well separated and had good linearity in the range of 0.0025-0.4000 mg/ml. The average recoveries and RSD of oleanolic acid were 93.53% and 3.5%, 94.18% and 3.0% respectively. CONCLUSION: The method is good for determining oleanolic acid and ursolic acid in Chinese medicines.

Chromatography, Gas↗
PubMed2003

Isolation, characterization and biological activity of betulinic acid and ursolic acid from Vitex negundo L.

Two pentacyclic triterpenoids, betulinic acid (3beta-hydroxylup-20-(29)-en-28-oic acid) (3), and ursolic acid (2beta-hydroxyurs-12-en-28-oic acid) (4), were isolated for the first time from leaves of Vitex negundo L. along with three other compounds; an aliphatic alcohol n-hentriacontanol (1), beta-sitosterol (2) and p-hydroxybenzoic acid (5). Their antifeedant activity against the larvae of an agricultural pest, the castor semilooper (Achoea janata), in a no-choice laboratory assay and their antibacterial activity against Bacillus subtilis and Escherichia coli, by the paper disc method, were tested. Ursolic acid (4) showed more effective antifeedant activity than the betulinic acid (3). However, both these compounds have shown a very mild antibacterial activity. The other three compounds; n-hentriacontanol (1), beta-sitosterol (2) and p-hydroxybenzoic acid (5) have shown a little antifeedant activity against the larvae and did not show any antibacterial activity.

Animals↗
PubMed1991

Protective effect of oleanolic acid and ursolic acid against lipid peroxidation.

In a search for plant products against cancer, the protective effect of two plant products, ursolic acid isolated from Ocimum sanctum and oleanolic acid from Eugenia jumbolana against free radical induced damage was studied. Three different standard systems viz., ascorbic acid, carbon tetrachloride, ADP/Iron were used to induce lipid peroxidation in isolated rat liver microsomes in vitro. Both oleanolic acid and ursolic acid offered remarkable protection of 90% and 60% respectively. Both the compounds did not induce lipid peroxidation by themselves that improved the therapeutic application.

Adenosine Diphosphate↗
PubMed1997

Oleanolic acid and ursolic acid stabilize liposomal membranes.

The effects of oleanolic acid (OA) and ursolic acid (UA) on the fluidity and stability of dipalmitoyl phosphatidylcholine (DPPC) liposomal membrane were monitored by measuring the fluorescence polarization of 1,6-diphenyl-1,3,5-hexatriene labeled in the liposomal membrane and the leakage of calcein from the probe-encapsulated liposomes. The experiments with the liposomes made of DPPC and OA or UA showed that OA and UA exhibited a moderate fluidity-modulating effect for the liquid-crystalline liposomal membrane, and a strong condensing effect for both crystalline and liquid-crystalline liposomal membranes. Their effects were comparable to those of cholesterol. These results suggest that their fluidity-modulating and condensing effects might have some implications in their biological functions.

Diphenylhexatriene↗
PubMed1997

Effects of oleanolic acid and ursolic acid on inhibiting tumor growth and enhancing the recovery of hematopoietic system postirradiation in mice.

Two triterpene acids, oleanolic acid (OA) and ursolic acid (UA) were examined for their ability to inhibit the tumor growth and modify hematopoiesis after irradiation in three experimental systems: (a) in vivo anti-tumor activity of implanted tumor by ascitic cells was found to be augmented by addition of OA and UA at a high concentration and inhibited in a dose-dependent manner; (b) in the sublethal whole-body irradiated mice treated with the drugs in the 30 min preirradiation period, enhanced effects of OA and UA on peripheral leukocytes were observed by a different significance, and (c) when these chemicals were administered i.p. to mice 30 min before 4 Gy irradiation, both OA and UA enhanced the postirradiation responses of splenic blastogenesis by PHA. UA was a more potent tumorigenic inhibitor than OA. Combining with the gamma-irradiation, however, there was no significant synergetic effect on their anti-tumor activity. The beneficial effects of OA and UA on hematopoiesis and immunocompetence under this study, suggested they might partially play a role in anti-cancer and, furthermore, with the ability to decrease undesirable radiation damage to the hematopoietic tissue after radiotherapy.

Animals↗
PubMed2004

Inhibition of cytochrome P450 activities by oleanolic acid and ursolic acid in human liver microsomes.

Oleanolic acid (OA) and ursolic acid (UA), triterpene acids having numerous pharmacological activities including anti-inflammatory, anti-cancer, and hepato-protective effects, were tested for their ability to modulate the activities of several cytochrome P450 (CYP) enzymes using human liver microsomes. OA competitively inhibited CYP1A2-catalyzed phenacetin O-deethylation and CYP3A4-catalyzed midazolam 1-hydroxylation, the major human drug metabolizing CYPs, with IC50 (Ki) values of 143.5 (74.2) microM and 78.9 (41.0) microM, respectively. UA competitively inhibited CYP2C19-catalyzed S-mephenytoin 4'-hydroxylation with an IC50 (Ki) value of 119.7 (80.3) microM. However, other CYPs tested showed no or weak inhibition by both OA and UA. The present study demonstrates that OA and UA have inhibitory effects on CYP isoforms using human liver microsomes. It is thus likely that consumption of herbal medicines containing OA or UA, or administration of OA or UA, can cause drug interactions in humans when used concomitantly with drugs that are metabolized primarily by CYP isoforms. In addition, it appears that the inhibitory effect of OA on CYP1A2 is, in part, related to its anti-inflammatory and anticancer activities.

Chromatography, High Pressure Liquid↗
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↗
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↗