Disease relevance of OLEANOLIC ACID

• Results obtained show that oleanolic acid inhibits the HIV-1 replication in all the cellular systems used (EC50 values: 22.7 microM, 24.6 microM and 57.4 microM for in vitro infected PBMC, naturally infected PBMC and M/M, respectively) [1].
• Compounds, oleanolic acid, and 6'-(beta-sitosteryl-3- O-beta- D-glucopyranosidyl) pentadecanoate showed marginal cytotoxicity against Hep G2 cells (human liver cancer cells) with IC50 values of 14.4, 17.4, 4.9, 8.0, and 9.2 microg/mL, respectively [2].
• The highest cicatrizant activity in mice was obtained by applying 40 microg of oleanolic acid per gram of body weight [3].
• Effects of oleanolic acid glycosides on gastrointestinal transit and ileus in mice [4].
• Of the isolated compounds, 3-oxotirucalla-7, 24-dien-21-oic acid (2), oleanolic acid (4), and 6 were found to be inhibitory substances against human immunodeficiency virus (HIV-1) protease, with their 50% inhibitory concentrations (IC(50)) being 20, 10, and 70 microg/mL, respectively [5].

Psychiatry related information on OLEANOLIC ACID

• The active principles of the extract were isolated and purified by repeated column chromatography and their structures were identified as oleanolic acid glycosides known as momordin I, Id, and Ie [6].

High impact information on OLEANOLIC ACID

• A series of synthetic triterpenoid (TP) analogues of oleanolic acid are powerful inhibitors of cellular inflammatory processes such as the induction by IFN-gamma of inducible nitric oxide synthase (iNOS) and of cyclooxygenase 2 in mouse macrophages [7].
• We investigated the effect on cell proliferation and apoptosis in HT-29 cells of an extract from the skin of olives composed of pentacyclic triterpenes with the main components maslinic acid (73.25%) and oleanolic acid (25.75%) [8].
• Phytocomponents of triterpenoids, oleanolic acid and ursolic acid, regulated differently the processing of epidermal keratinocytes via PPAR-alpha pathway [9].
• After an intraperitoneal injection into the fasting Wistar rats for 90 min, oleanolic acid decreased the plasma glucose in a dose-dependent manner in parallel to an increase of plasma levels of insulin as well as C-peptide [10].
• Release of acetylcholine to raise insulin secretion in Wistar rats by oleanolic acid, one of the active principles contained in Cornus officinalis [10].

Chemical compound and disease context of OLEANOLIC ACID

• 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 [11].
• Effects of pharmacological preconditioning by emodin/oleanolic acid treatment and/or ischemic preconditioning on mitochondrial antioxidant components as well as the susceptibility to ischemia-reperfusion injury in rat hearts [12].
• 3beta-Hydroxyolean-12-en-27-oic acid (1), a biologically active, pentacyclic triterpenoid isolated from the rhizomes of Astilbe chinensis, was found to be considerably more cytotoxic toward human colorectal carcinoma (COLO-205) and human cervical squamous carcinoma (HeLa) cells than its congener oleanolic acid (4) [13].
• A gene for cytochrome P450 (moxA) from Nonomuraea recticatena, coexpressed with camAB for pseudomonad redox partners in Escherichia coli, hydroxylated oleanolic acid to produce queretaroic acid [14].
• Liver damage was assessed by serum activities of alanine aminotransferase and sorbitol dehydrogenase, as well as by histopathological examination. alpha-Hederin, ursolic acid, and oleanolic acid markedly decreased the toxicity produced by all three hepatotoxicants [15].

Biological context of OLEANOLIC ACID

• Inhibitory effect of oleanolic acid on 12-O-tetradecanoylphorbol-13-acetate-induced gene expression in mouse skin [16].
• Preliminary structure-activity relationships of the oleanolic acid derivatives are discussed [17].
• Structure-related inhibitory activity of oleanolic acid glycosides on gastric emptying in mice [18].
• In the report presented, antiproliferative effects and leukemia cell growth and apoptosis modulating activities of ursolic acid (UA) and oleanolic acid (OA) were investigated [19].
• In vivo wound-healing activity of oleanolic acid derived from the acid hydrolysis of Anredera diffusa [3].

Anatomical context of OLEANOLIC ACID

• In both cell compartments studied 37% of total cellular oleanolic acid were accumulated, 0.6% occurring as free oleanolic acid (only in vacuoles) [20].
• The contents of oleanolic acid and its 3-0-glucuronide derivatives as well as of 3-0-glucoside derivatives were determined in vacuoles prepared from protoplasts and cell walls obtained from cells of Calendula officinalis leaves [20].
• Thus, oleanolic acid caused transformation of erythrocytes into stomatocytes in the concentration range where the in vitro antiplasmodial activity was observed [21].
• Five new oleanolic acid glycosides from Achyranthes bidentata with inhibitory activity on osteoclast formation [22].
• Distribution of oleanolic acid glycosides in vacuoles and cell walls isolated from protoplasts and cells of Calendula officinalis leaves [20].

Associations of OLEANOLIC ACID with other chemical compounds

• The triterpenes ursolic acid, oleanolic acid and gypsogenic acid were active against blood trypomastigote forms of Trypanosoma cruzi [23].
• Six triterpenoids, chiisanogenin, chiisanoside, ursolic acid, oleanolic acid, beta-sitosterol and daucosterol, were isolated as the platelet anti-aggregating components from the leaves of Acanthopanax senticosus and the fruits of A. sessiliflorus [24].
• Glucuronide Saponins of Oleanolic Acid from Achyranthes fauriei Roots [25].
• Pectin administered to Uncaria tomentosa cell suspension cultures, was found to increase the production of triterpene acids (ursolic and oleanolic acid), however, neither growth nor sterol accumulation were affected [26].
• It has been found that the water solubilities of saikosaponins, the active principles of Bupleuri radix, are greatly increased in the presence of ginsenoside-Ro, the glucuronide bisdesmoside of oleanolic acid of Ginseng [27].

Gene context of OLEANOLIC ACID

• Oleanolic acid was without effect on both the production of NO and secretion of TNF-alpha [28].
• The MeOH-soluble fraction of the water extract of Catharanthus roseus from Indonesia, having shown potent inhibitory activity on the metabolism mediated by CYP2D6, was subjected to activity-guided isolation to yield two triterpenes, ursolic acid (1) and oleanolic acid (2), and three alkaloids, vindoline (3), ajmalicine (4), and serpentine (5) [29].
• Cytokine-mediated induction of metallothionein in Hepa-1c1c7 cells by oleanolic acid [30].
• Although oleanolic acid and ursolic acid of the triterpenoids did not significantly affect the proliferation of PBMC, they exhibited a strong stimulation of IFN-gamma secretion [31].
• Hederacolchisid A1, a new oleanolic acid monodesmoside, isolated from Hedera colchica K [32].

Analytical, diagnostic and therapeutic context of OLEANOLIC ACID

• All the oleanolic acid glycosides inhibited the formation of osteoclast-like multinucleated cells (OCLs) induced by 1alpha,25(OH)2D3 in a co-culture assay system [22].
• A systematic study of standard triterpenes (alpha-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) [33].
• Determination of oleanolic acid in human plasma and study of its pharmacokinetics in Chinese healthy male volunteers by HPLC tandem mass spectrometry [34].
• 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 [35].
• Differential scanning calorimetry and X-ray diffraction studies indicated that oleanolic acid was present in an amorphous state in the lyophilized nanosuspensions [36].

References