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Oleanolic Acid (oleanolic + acid)

Distribution by Scientific Domains

Chemistry	70%
Medical Sciences	25%

Selected Abstracts

Antioxidative and Anti-Inflammatory Protection of Oleanolic Acid and Ursolic Acid in PC12 Cells

JOURNAL OF FOOD SCIENCE, Issue 7 2008
Shih-Jei Tsai
ABSTRACT:, PC12 cells were used to examine the in vitro antioxidative and anti-inflammatory effects of oleanolic acid (OA) and ursolic acid (UA). PC12 cells were pretreated with OA or UA at 20 and 40 ,M and followed by exposure of hydrogen peroxide (H2O2) or 1-methyl-4-phenylpyridinium ion (MPP+) to induce cell injury. Results showed that H2O2 - or MPP+ -treatment significantly decreased cell viability and increased lactate dehydrogenase (LDH) release (P < 0.05). The pretreatment from OA or UA significantly and concentration-dependently reduced subsequent H2O2 - or MPP+ -induced cell death and LDH release (P < 0.05). Either H2O2 - or MPP+ -treatment significantly increased malonyldialdehyde (MDA) formation, decreased glutathione (GSH) content, and diminished glutathione peroxidase (GPX), catalase, and superoxide dismutase (SOD) activities (P < 0.05). The pretreatment from OA or UA significantly retained GSH, and reversed H2O2 - and MPP+ -induced impairment in catalase and SOD activities (P < 0.05), and decreased MDA formation (P < 0.05). Either H2O2 - or MPP+ -treatment significantly elevated interleukin-6 (IL-6) and tumor necrosis factor (TNF)-, levels (P < 0.05). The pretreatments from OA or UA significantly attenuated subsequent H2O2 - or MPP+ -induced release of IL-6 and TNF-, (P < 0.05). Based on the observed antioxidative and anti-inflammatory activities from OA and UA, these 2 compounds were potent agents against neurodegenerative disorder. [source]

Gas phase isomeric differentiation of oleanolic and ursolic acids associated with heptakis-(2,6-di- O -methyl)-,-cyclodextrin by electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry

JOURNAL OF MASS SPECTROMETRY (INCORP BIOLOGICAL MASS SPECTROMETRY), Issue 4 2010
Zhan Yu
Abstract Oleanolic acid (OA) and ursolic acid (UA) are isomeric triterpenoid compounds with similar pharmaceutical properties. Usually, modern chromatographic and electrophoretic methods are widely utilized to differentiate these two compounds. Compared with mass spectrometric (MS) methods, these modern separation methods are both time- and sample-consuming. Herein, we present a new method for structural differentiation of OA and UA by Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) with the association of heptakis-(2,6-di- O -methyl)-,-cyclodextrin (DM-,-CD). Exact MS and tandem MS (MS/MS) data showed that there is no perceptible difference between OA and UA, as well as their ,-cyclodextrin and ,-cyclodextrin complexes. However, there is a remarkable difference in MS/MS spectra of DM-,-CD complexes of OA and UA. The peak corresponding to the neutral loss of a formic acid and a water molecule could only be observed in the MS/MS spectrum of the complex of DM-,-CD : OA. Molecular modeling calculations were also employed to further investigate the structural differences of DM-,-CD : OA and DM-,-CD : UA complexes. Therefore, by employing DM-,-CD as a reference reagent, OA and UA could be differentiated with purely MS method. Copyright © 2010 John Wiley & Sons, Ltd. [source]

Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L.

JOURNAL OF PHARMACY AND PHARMACOLOGY: AN INTERNATI ONAL JOURNAL OF PHARMACEUTICAL SCIENCE, Issue 1 2005
K. Urech
Detection of antiproliferative activity and bioactivity-guided fractionation of viscin, a lipophilic extract from Viscum album L., led to the isolation of betulinic acid, oleanolic acid and ursolic acid as active components. Viscin, betulinic acid, oleanolic acid and ursolic acid inhibited growth and induced apoptotic cell death in Molt4, K562 and U937 leukaemia cells. The growth inhibitory effect of viscin was more pronounced in Molt4 and U937 cells (IC50 (concentration that inhibited cell proliferation by 50%): 118 ± 24 and 138 ± 24 ,g mL,1) than in K562 cells (IC50: 252 ± 37 ,g mL,1). Oleanolic acid was the least effective in all cell lines (7.5,45.5% inhibition at 10 ,g mL,1) and ursolic acid the most active in Molt4 and U937 cells (81.8 and 97.8% inhibition, respectively, at 5 ,g mL,1). A dose-dependent loss of membrane phospholipid asymmetry associated with apoptosis was induced in all cell lines as shown in flow cytometry by the externalization of phosphatidylserine and morphological changes in cell size and granularity. There were differences in individual cell lines' response towards the apoptosis-inducing effect of viscin, betulinic acid, oleanolic acid and ursolic acid. The triterpenoids ,-amyrin, ,-amyrinacetate, lupeol, lupeolacetate, ,-sitosterol and stigmasterol, and the fatty acids oleic acid, linoleic acid, palmitic acid and stearic acid were also present in the lipophilic extract. [source]

The structural elucidation of a novel iridoid derivative from Tachiadenus longiflorus (Gentianaceae) using the LSD programme and quantum chemical computations

PHYTOCHEMICAL ANALYSIS, Issue 2 2006
D. A. Mulholland
Abstract Oleanolic acid, scoparone, scopoletin and a novel iridoid derivative, angelone, were isolated from Tachiadenus longiflorus (Gentianaceae). The structure of angelone was determined from NMR data, given as input to the Logic for Structure Determination Programme, and was finally confirmed by comparison of experimental 13C-NMR chemical shifts with those obtained by quantum mechanical calculations. Copyright © 2005 John Wiley & Sons, Ltd. [source]

Enrichment of pomace olive oil in triterpenic acids during storage of "Alpeorujo" olive paste

EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, Issue 12 2008
Aranzazu García
Abstract Triterpenic acids are natural compounds present in plants and foods with beneficial properties for human health and thus they are desirable in the food, cosmetics and pharmaceutical industries. Pomace olive is considered a good source of these substances. In this study, oleanolic and maslinic acids were found to be the main triterpenic acids identified in pomace olive oil obtained from stored "Alpeorujo". Determination of the two acids was achieved by a new procedure that consists of extracting the acids from the oil with a mixture of methanol/ethanol, and then separating and quantifying them by HPLC. Results showed that their concentration increased up to 16,g/kg of oil during storage of the pomace in large ponds for 7,months. The concentration of both triterpenic acids was similar in the pomace olive oil obtained by using the centrifugation system. By contrast, a much lower concentration of maslinic than oleanolic acid was detected in pomace olive oils obtained by solvent extraction from the previously centrifugated "Alpeorujo" paste. These triterpenic acids also contributed to the acidity of the crude oil. Likewise, the oil of the pomace paste was enriched in other substances such as 4-ethylphenol and aliphatic alcohols during the storage of the paste in large ponds. Consequently, crude pomace olive oil can be considered a good source of triterpenic acids when obtained from a stored olive paste. [source]

Oleanane Saponins from Rhizome of Anemone raddeana

HELVETICA CHIMICA ACTA, Issue 1 2010
Li Fan
Abstract Two new oleanolic acid-type triterpenoid saponins, raddeanosides R22 and R23 (1 and 2, resp.), together with four known saponins were isolated from the rhizome of Anemone raddeanaRegel. The structures of the new compounds were elucidated as oleanolic acid 3- O - , - D -glucopyranosyl(1,2)[, - D -glucopyranosyl(1,4)]- , - L -arabinopyranoside (1) and oleanolic acid 3- O - , - L -arabinopyranosyl(1,3)- , - L -rhamnopyranosyl(1,2)[, - D -glucopyranosyl(1,4)]- , - L -arabinopyranoside (2). The four known compounds were identified as oleanolic acid 3- O - , - L -arabinopyranoside (3), oleanolic acid 3- O - , - D -glucopyranosyl(1,4)- , - L -arabinopyranoside (4), hederasaponin B (5), and hederacholchiside E (6) on the basis of chemical and spectral evidences. Compound 4 is reported for the first time from the Anemone genus, while the other three known compounds have been already found in this plant. [source]

Withanolides from Withania adpressa

HELVETICA CHIMICA ACTA, Issue 2 2007
Hasna Abdeljebbar, Lalla
Abstract From the leaves of Withania adpressa, a plant endemic to Sahara of Morocco and Algeria, the novel steroidal lactone (22R)-14,,15,,17,,20, -tetrahydroxy-1-oxowitha-2,5,24-trien-26,22-olide (=,(15S,17S)-14,15,17,20-tetrahydroxy-22,26-epoxyergosta-2,5,24-triene-1,26-dione; 1), was isolated, along with three known compounds, withanolides F (2), J (3), and oleanolic acid. Their structures were mainly solved by in-depth 1D- and 2D-NMR (including ADEQUATE) experiments, as well as by HR-MS analyses and chemical evidence. [source]

Treatment of actinic keratoses with birch bark extract: a pilot study

JOURNAL DER DEUTSCHEN DERMATOLOGISCHEN GESELLSCHAFT, Issue 2 2006
Constance Huyke
aktinische Keratosen; Betulinsäure; Betulin; Oleanolsäure Summary Background: Birch bark contains a variety of apoptosis-inducing and anti-inflammatory substances such as betulinic acid, betulin, oleanolic acid and lupeol. Therefore, birch bark extract may be effective in the treatment of actinic keratoses. To address this issue, a pilot study using a standardized birch bark ointment was performed. Methods: Twenty-eight patients with actinic keratoses were enrolled in this prospective, non-randomized pilot study. Fourteen patients were treated with birch bark ointment only; fourteen patients received a combination therapy with cryotherapy and birch bark ointment. Treatment response was assessed clinically after two months. Results: Clearing of more than 75 % of the lesions was seen in 79 % of the patients treated with birch bark ointment monotherapy. The response rate of the combined treatment modality was 93 %. Therapy with birch bark ointment was well tolerated. Conclusion: In this pilot study, a standardized birch bark extract was effective in the treatment of actinic keratoses. This therapy is easy to perform and it has no side effects. Birch bark ointment may be a new therapeutic option for actinic keratoses. Zusammenfassung Hintergrund: Birkenkork ist reich an Triterpenen (Betulin, Betulinsäure, Oleanolsäure, Lupeol, Erythrodiol), für die Apoptose induzierende und antientzündliche Wirkungen beschrieben sind. Deshalb könnte sich ein Extrakt aus Birkenkork für die Therapie von aktinischen Keratosen eignen. Mit der hier untersuchten Birkenkork-Creme liegt erstmals eine galenische Formulierung vor (Birkenkorkextrakt, pflanzliche Öle, Wasser), in der die Wirkstoffe des Birkenkorks in therapeutisch ausreichender Menge vorhanden sind. Methoden: Im Rahmen der prospektiven, nicht randomisierten Pilotstudie wurden 28 Patienten mit aktinischen Keratosen behandelt. 14 Patienten erhielten eine Creme mit Birkenkorkextrakt als Monotherapie, 14 Patienten wurden zusätzlich kryotherapeutisch behandelt. Die Birkenkork-Creme wurde von den Patienten zweimal täglich aufgetragen. Das klinische Ansprechen wurde nach zwei Monaten erfasst. Ergebnisse: Bei Behandlung mit Birkenkorkextrakt als Monotherapie zeigten 79 % der Patienten nach einem Beobachtungszeitraum von zwei Monaten eine klinische Abheilung von über 75 % der Läsionen. Bei der Kombinationsbehandlung mit Kryotherapie kam es bei 93 % der Patienten zu einem Ansprechen auf die Behandlung. Die Verträglichkeit der Birkenkork-Creme war in allen Fällen sehr gut. Schlussfolgerung: Im Rahmen dieser Pilotstudie zeigte die lokale Anwendung eines standardisierten Birkenkorkextraktes eine gute Wirksamkeit bei der Behandlung aktinischer Keratosen. Die Anwendung ist einfach und die Verträglichkeit sehr gut. Deshalb stellt Birkenkorkextrakt eine interessante neue Therapieoption für aktinische Keratosen dar. [source]

Behandlung aktinischer Keratosen mit Birkenkorkextrakt: Eine Pilotstudie

Antioxidative and Anti-Inflammatory Protection of Oleanolic Acid and Ursolic Acid in PC12 Cells

Apoptosis inducing activity of viscin, a lipophilic extract from Viscum album L.

1H and 13C NMR spectral data of new saponins from Cordia piauhiensis

MAGNETIC RESONANCE IN CHEMISTRY, Issue 8 2007
Renata P. Santos
Abstract Two new bidesmoside triterpenoid saponins were isolated from stems of Cordia piauhiensis. Their structures, characterized as 3- O -,- L -rhamnopyranosyl-(1 , 2)-,- D -glucopyranosyl pomolic acid 28- O -,- D -glucopyranosyl ester (1) and 3- O -,- L -rhamnopyranosyl-(1 , 2)-,- D -glucopyranosyl oleanolic acid 28- O -,- D -glucopyranosyl-(1 , 6)-,- D -glucopyranosyl ester (2), were unequivocally established after extensive NMR (1H, 13C, DEPT 135 , COSY, HSQC, HMBC, TOCSY, and NOESY) studies. Copyright © 2007 John Wiley & Sons, Ltd. [source]

Characterization of two minor saponins from Cordia piauhiensis by 1H and 13C NMR spectroscopy

MAGNETIC RESONANCE IN CHEMISTRY, Issue 6 2005
Renata P. Santos
Abstract A careful NMR analysis with full assignment of the 1H and 13C spectral data for two minor saponins isolated from stems of Cordia piauhiensis is reported. These saponins were isolated by high-performance liquid chromatography and characterized as 3,- O -[,- L -rhamnopyranosyl-(1 , 2)-,- D -glucopyranosyl]pomolic acid 28- O -[,- D -glucopyanosyl-(1 , 6)-,- D -glucopyranosyl] ester (1) and 3,- O -[,- L -rhamnopyranosyl-(1 , 2)-,- D -glucopyranosyl]oleanolic acid 28- O -[,- D -xylopyranosyl-(1 , 2)-,- D -glucopyanosyl-(1 , 6)-,- D -glucopyranosyl] ester (2). Their structures were established using a combination of 1D and 2D (1H, 1H-COSY, TOCSY, NOESY, gs -HMQC and gs -HMBC) NMR techniques, electrospray ionization mass spectrometry and chemical evidence. Copyright © 2005 John Wiley & Sons, Ltd. [source]

Complete assignments of 1H and 13C NMR resonances of oleanolic acid, 18,-oleanolic acid, ursolic acid and their 11-oxo derivatives

MAGNETIC RESONANCE IN CHEMISTRY, Issue 8 2003
Werner Seebacher
Abstract Complete assignments of 1H and 13C NMR chemical shifts for oleanolic acid, 18,-oleanolic acid, ursolic acid and their 11-oxo derivatives based on 1H, 13C, 2D DQF-COSY, NOESY, HSQC, HMBC and HSQC-TOCSY experiments were achieved. Copyright © 2003 John Wiley & Sons, Ltd. [source]

Recent developments in anti-inflammatory natural products

MEDICINAL RESEARCH REVIEWS, Issue 5 2009
Raju Gautam
Abstract Many of the inflammatory diseases are becoming common in aging society throughout the world. The clinically used anti-inflammatory drugs suffer from the disadvantage of side effects and high cost of treatment (in case of biologics). Alternative to these drugs are traditional medicines and natural products, which offer a great hope in the identification of bioactive lead compounds and their development into drugs for treating inflammatory diseases. Since ancient times traditional medicines and phytopharmaceuticals are being used for the treatment of inflammatory and other disorders. The present review article describes anti-inflammatory natural products derived from plants and marine sources reported during last decade. The compounds described belong to different chemical classes such as alkaloids, steroids, terpenoids, polyphenolics, phenylpropanoids, fatty acids and lipids, and various miscellaneous compounds. The attempt is also being made to enumerate the possible leads, e.g. curcumin, resveratrol, baicalein, boswellic acid, betulinic acid, ursolic acid, and oleanolic acid, for further development with the help of structure,activity relationship (SAR) studies and their current status. In addition SAR studies carried out on the anti-inflammatory activity of flavonoid compounds and clinical studies performed on anti-inflammatory natural products are also discussed. © 2009 Wiley Periodicals, Inc. Med Res Rev, 29, No. 5, 767,820, 2009 [source]

Bioassay-guided fractionation of lemon balm (Melissa officinalis L.) using an in vitro measure of GABA transaminase activity

PHYTOTHERAPY RESEARCH, Issue 8 2009
Rosalie Awad
Abstract A novel pharmacological mechanism of action for the anxiolytic botanical Melissa officinalis L. (lemon balm) is reported. The methanol extract was identified as a potent in vitro inhibitor of rat brain GABA transaminase (GABA-T), an enzyme target in the therapy of anxiety, epilepsy and related neurological disorders. Bioassay-guided fractionation led to the identification and isolation of rosmarinic acid (RA) and the triterpenoids, ursolic acid (UA) and oleanolic acid (OA) as active principles. Phytochemical characterization of the crude extract determined RA as the major compound responsible for activity (40% inhibition at 100 µg/mL) since it represented approximately 1.5% of the dry mass of the leaves. Synergistic effects may also play a role. Copyright © 2009 John Wiley & Sons, Ltd. [source]

Chemical study of triterpenoid resinous materials in archaeological findings by means of direct exposure electron ionisation mass spectrometry and gas chromatography/mass spectrometry

RAPID COMMUNICATIONS IN MASS SPECTROMETRY, Issue 11 2006
Francesca Modugno
A systematic study of standard triterpenes (, -amyrine, oleanolic acid, betulin, lupeol, betulinic acid and lupenone) and of raw resinous materials (frankincense resin, mastic resin and birch bark pitch) was performed using direct exposure electron ionisation mass spectrometry (DE-MS) and gas chromatography/mass spectrometry (GC/MS). DE-MS provides a mass spectral fingerprint of organic materials in a few minutes which highlights the compounds that are the main components in the sample. The application of principal component analysis (PCA) on DE-MS data in the mass ranges m/z 181,260 and m/z 331,500, corresponding to the fragmentation of triterpenoid molecules, enabled us to distinguish between different triterpenoid materials such as mastic resin, frankincense resin and birch bark pitch, and to graphically plot the resinous substances in three separate clusters, retaining 89% of the total variance. GC/MS analysis of the same materials has permitted us to elucidate in detail the molecular composition and to identify minor components and species that act as markers of the degradation undergone by the materials. The paper also reports the results for the organic residues contained in an Egyptian censer (5th,7th century AD) which was recovered in the excavation of the Necropolis of Antinoe (Egypt), and for the hafting material found on a Palaeolithic tool recovered at the site of Campitello (Arezzo, Tuscany), dating back to the Mid-Pleistocene period. Although DE-MS was found to be a fast analytical tool, it failed to give any information on the presence of less abundant compounds when applied to mixtures of different materials: only mastic resin was found in the residues from the Roman censer, whereas GC/MS analysis identified the presence of a vegetable oil from Brassicaceae seeds and Pinaceae resin. Birch bark pitch as a pure material was identified in the sample from the Palaeolithic flint flake using both procedures. Copyright © 2006 John Wiley & Sons, Ltd. [source]

Determination of oleanolic acid, ursolic acid and amygdalin in the flower of Eriobotrya japonica Lindl. by HPLC

BIOMEDICAL CHROMATOGRAPHY, Issue 7 2007
Chunhua Zhou
Abstract Simple and accurate HPLC methods were developed for the determination of oleanolic acid (OA), ursolic acid (UA) and amygdalin in loquat (Eriobotrya japonica Lindl.) flower, which is commonly used for the treatment of various diseases as a traditional Chinese medicine. HPLC assay was performed on a reversed-phase C18 column and all three compounds were detected at 210 nm with a flow rate of 1.0 mL/min. The mobile phase consisted of methanol (A) and 0.03 mol/L phosphate buffer (pH 2.8) (B) with a ratio of 88:12 (A:B, v/v) for simultaneous detection of OA and UA, and 25:75 (A:B, v/v) for detection of amygdalin. The established methods showed good precision and accuracy with overall intra-day and inter-day variation of 0.99,3.55 and 1.05,4.05%, respectively, and overall recoveries of 97.37,99.32% for the three compounds. Application of these methods to determine the OA, UA and amygdalin contents in loquat flower showed that cultivar had a minor effect on the contents of all three compounds, with average amounts of 0.38,0.51 mg OA/g dry weight (DW), 2.15,2.68 mg UA/g DW and 1.23,1.56 mg amygdalin/g DW among five loquat cultivars tested. However, developmental stages and flower tissues showed significant effect on the contents of all three bioactive components. Copyright © 2007 John Wiley & Sons, Ltd. [source]