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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↗
PubMedDate not supplied

Quantification of eugenol, luteolin, ursolic acid, and oleanolic acid in black (Krishna Tulasi) and green (Sri Tulasi) varieties of Ocimum sanctum Linn. using high-performance thin-layer chromatography.

Ocimum sanctum (family Lamiaceae) is a reputed drug of Ayurveda, commonly known as Tulasi. In the present work, we quantified 4 marker compounds, viz., eugenol, luteolin, ursolic acid, and oleanolic acid, from the leaf of green and black varieties of O. sanctum using high-performance thin-layer chromatography (HPTLC) with densitometry. The methods were found to be precise, with relative standard deviation (RSD) values for intraday analyses in the range of 0.52 to 0.91%, 0.77 to 1.29%, 0.11 to 0.16%, and 0.34 to 0.42% and for interday analyses in the range of 0.73 to 0.96%, 1.02 to 2.08%, 0.11 to 0.12%, and 0.39 to 0.64% for different concentrations of eugenol, luteolin, ursolic acid, and oleanolic acid, respectively. Instrumental RSD values were 0.24, 0.39, 0.21, and 0.18% for eugenol, luteolin, ursolic acid, and oleanolic acid, respectively. Accuracy of the methods was checked by conducting a recovery study at 3 different levels for the 4 compounds, and the average recoveries were found to be 99.73, 99.3, 100.58, and 100.57%, respectively. Eugenol content ranged from 0.175 to 0.362% (w/w) and luteolin from 0.019 to 0.046% (w/w) in the samples analyzed. Green variety was found to contain higher amounts of ursolic acid [0.478 and 0.348% (w/w), from Sources 1 and 2, respectively] than the black variety [0.252 and 0.264% (w/w) from Sources 1 and 2, respectively]. Black variety had 0.174 and 0.218% (w/w) of oleanolic acid from Sources 1 and 2, respectively, while it was not detected in the green variety. Ursolic acid and oleanolic acid ran at the same Rf value and could not be resolved in several solvent systems tried. However, we observed that only ursolic acid gave yellow fluorescence under 366 nm ultraviolet light after derivatization with anisaldehyde-sulfuric acid reagent. The HPTLC-densitometry methods for the quantification of the 4 markers in O. sanctum leaf will have the applicability in quality control.

Calibration↗
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↗
PubMed1993

Phytochemical studies of seeds of medicinal plants. III. Ursolic acid and oleanolic acid glycosides from seeds of Patrinia scabiosaefolia Fischer.

Three isomeric pairs of ursolic acid (1, 3, and 5) and oleanolic acid (2, 4, and 6) glycosides were isolated as predominant constituents from seeds of Patrinia scabiosaefolia Fischer (Valerianaceae). Based on chemical and spectral evidence, their structures were established to be 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] ursolic acid (1) and oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl] ursolic acid (3) and oleanolic acid (4), and 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl- (1-->3)]-alpha-L-arabinopyranosyl] ursolic acid (5) and oleanolic acid (6), respectively. Glycosides 1, 5, and 6 are new compounds and named as patrinia-glycosides A-I, B-I, and B-II, respectively. Glycoside 3 is a known but is the first naturally occurring product. Ursolic acid glycosides were first found from this plant specimen.

Carbohydrate Sequence↗
PubMed2005

Anti-tumor activity of a 3-oxo derivative of oleanolic acid.

Oleanolic acid (3beta-hydroxy-olea-12-en-28-oic acid, OA) exists widely in plant kingdom and possesses various pharmacological activities. In recent years, it was found that it had marked anti-tumor effects and exhibited cytotoxic activity towards many cancer cell lines in culture. In this article, the anti-tumor and differentiation-inducing effects of a derivative of OA modified at C-3, 3-oxo oleanolic acid (3-oxo-olea-12-en-28-oic acid, 3-oxo-OA, 3-7-1) was reported. In vitro, 3-7-1 were found to inhibit significantly the growth of cancer cells derived from different tissues. And 3-7-1 had inhibitory effect on melanoma in vivo. This selection may relate to the differentiation induced by 3-7-1. The inhibition of 3-7-1 on B16-BL6 suggests that 3-7-1 may be a useful anti-cancer agent for melanoma.

Antineoplastic Agents↗
PubMed2004

Cytokine-mediated induction of metallothionein in Hepa-1c1c7 cells by oleanolic acid.

Oleanolic acid (OA), a pentacyclic triterpene acid, has been reported to possess inducing activity of hepatic metallothionein (MT). However, the mechanism underlying its effects is unknown. This study investigated the effects of OA on the regulation of MT expression in an in vitro model. OA that was added directly to Hepa-1c1c7 cells had no effect on MT induction. However, MT and its mRNA levels increased markedly when the Hepa-1c1c7 cells were cultured with the OA-treated conditioned media from the RAW 264.7 cells. Co-treating the RAW 264.7 cells with OA and pentoxifylline, a TNF-alpha synthesis inhibitor, resulted in a decrease in the effects of OA on the MT induction. In the OA-exposed RAW 264.7 cell cultures, production and mRNA levels of TNF-alpha and IL-6 were increased. However, the MT induction activity was inhibited when antibodies to TNF-alpha and/or IL-6 were added to the OA-treated conditioned media from the RAW 264.7 cells. These results suggest that the up-regulation of MT expression by OA was mediated by the TNF-alpha and IL-6 released from UA-activated macrophages.

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↗
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↗
PubMed2006

Antimutagenicity of ursolic acid and oleanolic acid against doxorubicin-induced clastogenesis in Balb/c mice.

Ursolic acid (UA) and oleanolic acid (OA) are triterpenoid compounds found in food, medicinal herbs and various other plants in free form or bound to glycosides. Both substances are known for their antimicrobial, hepatoprotective, anti-inflammatory, antiallergic, antiviral and cytotoxic activities. In the present study, we evaluated the antimutagenic potential of UA and OA using the micronucleus test in peripheral blood and bone marrow of Balb/c mice. The animals were divided into 10 treatment groups: mice treated with UA (80 mg/kg b.w.); OA (80 mg/kg b.w.); a mixture of UA and OA (80 mg/kg b.w.); the antineoplastic agent doxorubicin (DXR, 90 mg/kg b.w.); DMSO and DXR; UA and DXR; OA and DXR; UA, OA and DXR, and negative and solvent controls. UA, OA and a mixture of UA and OA were administered to the animals by gavage, followed by the intraperitoneal injection of DXR. The results showed a significant reduction in micronucleus frequency in the groups concomitantly treated with the triterpenoid compounds and DXR compared to that treated with DXR alone. The present results demonstrate the antimutagenic activity of UA and OA under the experimental conditions used in this study.

Animals↗
PubMed2002

Effects of ursolic acid and oleanolic acid on human colon carcinoma cell line HCT15.

AIM: Ursolic acid (UA) and oleanolic acid (OA) are triperpene acids having a similar chemical structure and are distributed wildly in plants all over the world. In recent years, it was found that they had marked anti-tumor effects. There is little literature currently available regarding their effects on colon carcinoma cells. The present study was designed to investigate their inhibitory effects on human colon carcinoma cell line HCT15. METHODS: HCT15 cells were cultured with different drugs. The treated cells were stained with hematoxylin-eosin and their morphologic changes observed under a light microscope. The cytotoxicity of these drugs was evaluated by tetrazolium dye assay. Cell cycle analysis was performed by flow cytometry (FCM). Data were expressed as means +/-SEM and Analysis of variance and Student' t-test for individual comparisons. RESULTS: Twenty-four to 72 h after UA or OA 60 micromol/L treatment, the numbers of dead cells and cell fragments were increased and most cells were dead at the 72nd hour. The cytotoxicity of UA was stronger than that of OA. Seventy-eight hours after 30 micromol/L of UA or OA treatment, a number of cells were degenerated, but cell fragments were rarely seen. The IC(50) values for UA and OA were 30 and 60 micromol/L, respectively. Proliferation assay showed that proliferation of UA and OA-treated cells was slightly increased at 24h and significantly decreased at 48 h and 60 h, whereas untreated control cells maintained an exponential growth curve. Cell cycle analysis by FCM showed HCT15 cells treated with UA 30 and OA 60 for 36 h and 72 h gradually accumulated in G(0)/G(1) phase (both drugs P<0.05 for 72 h), with a concomitant decrease of cell populations in S phase (both drugs P<0.01 for 72 h) and no detectable apoptotic fraction. CONCLUSION: UA and OA have significant anti-tumor activity. The effect of UA is stronger than that of OA. The possible mechanism of action is that both drugs have an inhibitory effect on tumor cell proliferation through cell-cycle arrest.

Antineoplastic Agents, Phytogenic↗
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↗
PubMed2005

Induced accumulation of oleanolic acid and ursolic acid in cell suspension cultures of Uncaria tomentosa.

Increasing sucrose from 20 to 50 g l(-1) in Uncaria tomentosa cell suspension cultures enhanced ursolic acid and oleanolic acid production from 129 +/- 61 to 553 +/- 193 microg g(-1) cell dry wt. The maximal concentration of both triterpenes (1680 +/- 39 microg g(-1) cell dry wt) was 8 days after elicitation by jasmonic acid, while yeast extract or citrus pectin treatments produced 1189 +/- 20 or 1120 +/- 26 microg g(-1) cell dry wt, respectively. The ratio of ursolic acid:oleanolic acid was constant at 70:30.

Biomass↗
PubMed2005

A pilot trial evaluating Meta050, a proprietary combination of reduced iso-alpha acids, rosemary extract and oleanolic acid in patients with arthritis and fibromyalgia.

The aim of this open-label, 8-week observational trial was to investigate the efficacy of Meta050 (a proprietary, standardized combination of reduced iso-alpha-acids from hops, rosemary extract and oleanolic acid) on pain in patients with rheumatic disease. Osteoarthritis, rheumatoid arthritis and fibromyalgia patients were given 440 mg Meta050 three times a day for 4 weeks, which was changed to 880 mg twice a day for the subsequent 4 weeks in the majority of patients. Pain and condition-specific symptoms were assessed using a standard visual analog scale (VAS), an abridged arthritis impact measurement scale (AIMS2) and the fibromyalgia impact questionnaire. Fifty-four subjects with rheumatic disease completed the trial. Following treatment, a statistically significant decrease in pain of 50% and 40% was observed in arthritis subjects using the VAS (p < 0.0001; Wilcoxon-ranked sums) and AIMS2 (p < 0.0001), respectively. Fibromyalgia subject scores did not significantly improve. A decreasing trend of C-reactive protein, a marker for inflammation, was also observed in those subjects who presented with elevated C-reactive protein. No serious side effects were observed. These observations suggest that Meta050 at a dosage of 440 mg three times a day has a beneficial effect on pain in arthritis subjects.

Administration, Oral↗
PubMed1992

Studies on the constituents of Aster scaber Thunb. III. Structures of scaberosides B7, B8 and B9, minor oleanolic acid glycosides isolated from the root.

Three new oleanolic acid 3,28-O-bisdesmosides, scaberosides B7, B8 and B9, were isolated as minor saponins from the root of Aster scaber THUNB. (Compositae), and their structures were determined based on spectral and chemical evidence as follows. Scaberoside B7 is 3-O-beta-D-glucopyranosyluronic acid oleanolic acid 28-[O-beta-D-apiofuranosyl-(1----3)-[O-beta-D-xylopyranosyl-(1---- 4)-O-alpha-L-rhamnopyranosyl-(1----2)-alpha-L-arabinopyranosyl] ester, scaberoside B8, 3-O-beta-D-glucopyranosyl oleanolic acid 28-[O-beta-D-xylopyranosyl-(1----4)-O-alpha-L-rhamnopyranosyl-(1----2)-a lpha-L-arabinopyranosyl] ester, and scaberoside B9, 3-O-beta-D-glucopyranosyluronic acid oleanolic acid 28-[O-alpha-L-rhamnopyranosyl-(1----2)-[O-beta-D-xylopyranosyl-(1----6)] -beta-D-glucopyranosyl] ester. Scaberosides B7 and B9 were obtained as their methyl esters.

Carbohydrate Conformation↗