Oleanoic acid

The research aims to identify the inhibitory potential of natural dietary phytochemicals against non-insulinotropic target protein alpha-glucosidase and its possible implications to diabetes mellitus type 2. A data set of sixteen plant-derived dietary molecules viz., 4,5-dimethyl-3-hydroxy-2(5H)-furanone, apigenin, bromelain, caffeic acid, cholecalciferol, dihydrokaempferol 7-o-glucopyranoside, galactomannan, genkwanin, isoimperatorin, luteolin, luteolin 7-o-glucoside, neohesperidin, oleanoic acid, pelargonidin-3-rutinoside, quercetin, and quinic acid were taken to accomplish molecular docking succeeded by their comparison with known inhibitors including acarbose, miglitol, voglibose, emiglitate, and 1-deoxynojirimycin...

To develop new potential agents against Chlamydia trachomatis among oleanane type triterpenoids the synthesis, spectral and X-ray analysis as well as antimicrobial screening of C-12 oxygen and nitrogen derivatives of erythrodiol is presented. The reduction of methyl 3β-acetoxy-12-oxo-oleanoate with LiAlH4 led to isomeric erythrodiol 12β- and 12α-hydroxy-derivatives, their stereochemistry with respect to the position of hydroxyl-group at C-12 was determined based on the multiplets splitting patterns, the magnitude of the spin-spin interaction, and NOESY interactions...

Spermacoce verticillata (L.) G. Mey. is commonly used in the folk medicine by various cultures to manage common diseases. Herein, the chemical and biological profiles of S. verticillata were studied in order to provide a comprehensive characterization of bioactive compounds and also to highlight the therapeutic properties. The in vitro antioxidant activity using free-radical scavenging, phosphomolybdenum, ferrous-ion chelating and reducing power assays, and the inhibitory activity against key enzymes such as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), tyrosinase, α-amylase and α-glucosidase of S...

Phytochemical study of Uvaria comperei afforded an alkaloid, 8,9-dimethoxy-5 H -phenanthridin-6-one ( 1 ), isolated and characterised (assignment of 1 H and 13 C NMR) for the first time from a natural source along with two flavonoids, (2S)-5-hydroxy-7,8-dimethoxyflavanone ( 2 ) and (2S)-7-hydroxy-5-methoxy-6,8-dimethylflavone ( 3 ). Clethric acid ( 4 ), oleanoic acid ( 5 ), β-sitosterol 3-O-β-D-glucopyranoside ( 9 ), β-sitosterol palmitate ( 6 ) and a mixture of stigmasterol ( 7 ) and β-sitosterol ( 8 ) were isolated from Oxyanthus unilocularis ...

The stem bark of Ancistrocarpus densispinosus Oliv. exhibited triterpenoids, including the rare fernane-type, fern-9(11)-ene-2α,3β-diol ( 1 ) a possible chemotaxonomically distinct biomolecule for the genus. Other triterpenoids that were isolated from this plant include the ursane-type ursolic acid ( 2 ) and corosolic acid ( 3 ), friedelane-type friedelin ( 4 ) and canophyllol ( 5 ), lupane-type lupeol ( 6 ), betulin ( 7 ), betulinic acid ( 8 ) and hennadiol ( 9 ), oleanoic acid ( 10 ), maslinic acid ( 11 ) and taraxerol ( 12 ) and three sterols...

An ultra-high-performance liquid chromatography-high-resolution mass spectrometry based profiling of a purified MeOH extract (PME) from the roots of Chenopodium bonus-henricus L. (Amaranthaceae) tentatively identified 15 saponins of six sapogenins. The PME exerts hepatoprotective and antioxidant activities comparable to those of flavonoid complex silymarin in in vitro (1 and 10 μg/mL) and in vivo (200 mg/kg/daily for 7 days) models of hepatotoxicity, induced by CCl4. The main constituents of PME, respectively saponins bonushenricoside A (1), 3-O-β-D-glucuronopyranosyl-bayogenin-28-O-β-D-glucopyranosyl ester (2), 3-O-β-D-glucuronopyranosyl-medicagenic acid-28-O-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl ester (3), 3-O-β-D-glucuronopyranosyl-2β-hydroxygypsogenin-28-O-β-D-glucopyranosyl ester (4), 3-O-α-L-rabinopyranosyl-bayogenin-28-O-β-D-glucopyranosyl ester (6) and bonushenricoside B (8) (3 μg/mL each), compared to silymarin (5 and 50 μg/mL), significantly reduced the cellular damage caused by CCl4 in rat hepatocytes, preserved cell viability and glutathione level, decreased lactate dehydrogenase leakage and reduced lipid damage...

Methyl 2-cyano-3,12-dioxo-18β-olean-1,9(11)-dien-30-oate (CDODO-Me, 10d) derived from glycyrrhetinic acid and methyl-2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO-Me) derived from oleanoic acid are potent apoptosis inducers developed to clinical trials. Both compounds have high affinity for reduced  glutathione (GSH), which needs to be overcome to improve their target selectivity. We generated a new 10d analogue methyl 2-cyano-3-oxo-18β-olean-1,9(11), 12-trien-30-oate (COOTO, 10e), which retains high apoptosis inducing ability, while displaying decreased affinity for GSH, and explored the acting targets...

In this study, an on-line supercritical fluid extraction (SFE) and supercritical fluid chromatography (SFC) method was developed for the rapid determination of oleanoic acid and ursolic acid in Chaenomelis Fructus. After optimization of the conditions, the two triterpenoid acids was obtained by SFE using 20% methanol as a modifier at 35°C in 8 min. They were resolved on a Shim-pack UC-X Diol column (4.6 × 150 mm, 3 μm) in 14 min (0 - 10 min, 5 - 10%; 10 - 14 min, 10% methanol in CO2 ) with a backpressure of 15 MPa at 40°C...

INTRODUCTION: The genus Quassia is a promising source of secondary metabolites with biological potential including antimalarial and cytotoxic activities. Limited data are available on the phytochemistry and pharmacology of Quassia silvestris Cheek & Jongkind, a Cameroonian medicinal plant used to treat various ailments. OBJECTIVES: To carry out the bioassay-guided fractionation and LC-HR-ESI-MS analyses of the leaves extract from Q. silvestris; to purify the active fractions and isolate the major compounds using different chromatographic and spectroscopic methods...

Nine triterpenes compounds were isolated from the male flowers of Eucommia ulmoides by recrystallization and chromatographic techniques over silica gel, Sephadex LH-20, and RP-18 gel. Their chemical structures were identified on the basis of spectral analysis and as 3-oxo-12-en-ursane-28-O-α-L-arabinofuranosyl (1 --> 6) -β-D-glucopyranoside (1), 2α, 3β-dihydroxyurs-12-en-28-oic acid(28 --> 1) -β-D-glucopyranosyl ester (2), ursolic acid (3), α-amyrin (4), uvaol (5), ursolic acid acetate (6), 3-O-acetate oleanoic acid (7), betulinic acid (8), and betulinol (9)...

In this study, we assessed the main bioactive compounds of a broad apple germplasm collection, composed by 247 accessions of wild (97) and domesticated (150) species. Among the stilbenes, trans- and cis-piceid were found to be ubiquitary components of both wild and cultivated apples. Apple was suggested to be the second dietary source of resveratrols. Results confirmed that the selection pressure of breeding and domestication did not uniformly affect all the phytochemicals contained in apples. For instance, organic acids (malic and ascorbic acid) and some phenolics (stilbenes, hydroxycinnamic acids, and dihydrochalcones) were significantly influenced by selection, while some relevant flavonoids (flavonols and flavan-3-ols) and triterpenoids (ursolic, oleanolic, and betulinic acids) were not...

Methyl triterpenoates derived from oleanolic, ursolic, betulinic, glycyrrhetinic, platanic, or maslinic acid were converted into their corresponding sulfamates and carbamoylsulfamates. The sulfamates were screened in photometric sulforhodamine assays for cytotoxic activity employing several human tumor cell lines. Many of the compounds showed EC50 values in one-digit μM concentration. Of special interest seems methyl (3β) 3-(aminosulfonyloxy)-11-oxo-oleanoate (18) showing good cytotoxicity for the human adenocarcinomic alveolar basal epithelial cell line A549 while being less toxic for non-malignant NIH 3T3 mouse fibroblasts...

Ischemic brain injury is a dynamic process involving oxidative stress, inflammation, cell death and the activation of endogenous adaptive and regenerative mechanisms depending on the activation of transcription factors such as hypoxia-inducible factor 1-alpha. Accordingly, we have previously described a new focal hypoxia model by direct intracerebral cobalt chloride injection. In turn, oleanolic acid, a plant-derived triterpenoid, has been extensively used in Asian countries for its anti-inflammatory and anti-tumor properties...

OBJECTIVE: To optimize the synthetic pathway and fermentation process of yeast cell factories for production of oleanoic acid. METHOD: Using the DNA assembler method, one copy of Glycyrrhiza glabra beta-amyrin synthase (GgbAS), Medicago truncatula oleanolic acid synthase (MtOAS) and Arabidopsis thaliana cytochrome P450 reductase 1 (AtCPR1) genes were introduced into Saccharomyces cerevisiae strain BY-OA, resulting in strain BY-20A. YPD medium with different glucose concentration were then used to cultivate strain BY-2OA...

Postharvest heat treatments (hot water or hot air treatment) may be applied to horticultural crops to control fungal diseases, insect infestation and to reduce chilling injury in cultivars susceptible to low storage temperatures. The present study investigated the influence of hot water (53 degrees C for 60s) and hot air treatment (38 degrees C for 24h) applied to two typical Sardinian apple varieties, cvs. Miali and Caddina, on the composition of the lipophilic extracts of the peel as well as on the antioxidant activity of ethanolic extracts of both peel and pulp...

BACKGROUND: It is well known that fluorescent labeling has recently become a major research tool in molecular and cellular biology for demonstrating therapeutic mechanisms and metabolic pathways. However, few studies have reported the use of fluorescent labeling of natural products. METHODS: We recently explored the boron 2-(2'-pyridyl) imidazole (BOPIM) derivative analogs, which are highly fluorescent, non-aggregated, and nontoxic. In the present study, the natural product oleanolic acid (OA) was functionalized and labeled with BOPIM, thus yielding a highly fluorescent probe, the comparison of cardioprotective effects of labeled and unlabeled OAs with BOPIM on primary neonatal rat cardiomyocytes with hypoxia/reoxygenation (H/R) injury were investigated...

Although postharvest quality of fruit is greatly affected by cuticle composition, structure, and properties, very few published studies have analyzed fruit cuticle composition from a postharvest perspective. In this work, the chemical composition of waxes and cutin, major cuticular components, was analyzed in fruit cuticle samples isolated from a melting ('October Sun') and a nonmelting ('Jesca') peach (Prunus persica L. Batsch.) cultivar at harvest and after a simulated shelf-life period of 5 days at 20 °C...

Apple peel contains numerous phytochemicals, many of which show bioactivity. This study investigated the identity of triterpenoid compounds contained in ethanolic extracts of peel from seven apple cultivars. Using HPLC-ESI-QTOF-HRMS, accurate mass information was obtained for 43 compounds, and chemical identity was inferred from the calculated elemental composition, fragment masses, ms/ms, and a limited set of authentic standards. Compounds were identified as triterpene acids and tentatively identified as ursenoic (or oleanoic) acid derivatives containing hydroxyl, oxo, and coumaroyloxy groups...

OBJECTIVE: To isolate and identify the chemical constituents from the active section with lowering blood sugar of agrimony. METHODS: The compounds were separated by repeated silica gel, polyamide and HPLC chromatographies. The structures of compounds isolated were identified by analysis of their spectral data and chemical peoperties. RESULTS: Nine compounds were isolated from the active section with lowering blood sugar of agrimony and their structures were identified as oleanoic acid (1), ursolic acid (2), 19alpha-hydroxy ursolic acid (3), tormentic acid (4), apigenin (5) , luteolin (6), kaempferol (7), 3,3'-di-O-methyl ellagic acid (8), kaempferol-7-O-alpha-L-rhamnoside (9)...

Flowing oil covered the Gulf like a blanket, but while no attempts so far had been effective at controlling the oil spill, treatments that do work to improve symptoms, prevent disability and offer an improved quality of life were discussed during the meeting on respiratory tract diseases. Within the same context of pollution by human activity, it is interesting to know that retreatment with anacardic acids reduced lung inflammation upon exposure to diesel exhaust particles in experimental animals (Carvalho, A...