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Oleanoic acid

Ping Gong, Kun Li, Ying Li, Dan Liu, Linxiang Zhao, Yongkui Jing
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...
May 24, 2018: Cell Death & Disease
Xiaotian Zhang, Feng Ji, Yueqi Li, Tian He, Ya Han, Daidong Wang, Zongtao Lin, Shizhong Chen
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...
2018: Analytical Sciences: the International Journal of the Japan Society for Analytical Chemistry
Michel Feussi Tala, Ferdinand Mouafo Talontsi, Guang-Zhi Zeng, Hippolyte Kamdem Wabo, Michael Spiteller, Ning-Hua Tan, Pierre Tane
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...
May 2017: Phytochemical Analysis: PCA
Yan-Xia Ding, Teng-Yu Wang, Yao-Wen Zhang, Yu-Mei Huang, Lin Ma, Dong-dong Li, De-Qiang Dou, Qin Li
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)...
November 2014: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Brian Farneti, Domenico Masuero, Fabrizio Costa, Pierluigi Magnago, Mickael Malnoy, Guglielmo Costa, Urska Vrhovsek, Fulvio Mattivi
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...
March 18, 2015: Journal of Agricultural and Food Chemistry
Sven Sommerwerk, Lucie Heller, René Csuk
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...
January 2015: Archiv der Pharmazie
Laura Caltana, Damián Rutolo, María Luisa Nieto, Alicia Brusco
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...
December 2014: Neurochemistry International
Dong Wang, Bei-Bei Wang, Yi Liu, Ming-Yu Shi, Dong-Guang Xiao, Lu-Qi Huang, Zhu-Bo Dai, Xue-Li Zhang
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...
July 2014: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
M L Ciavatta, M Gavagnin, M Serra, D Sanna, A Palma, A Barberis, M Schirra, A Fadda
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...
2013: Communications in Agricultural and Applied Biological Sciences
Sa Wang, Hai-bo He, Shu-zhang Xiao, Jun-zhi Wang, Cai-hong Bai, Na Wei, Kun Zou
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...
August 2014: Pharmacological Reports: PR
Burcu Belge, Montserrat Llovera, Eva Comabella, Jordi Graell, Isabel Lara
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...
April 16, 2014: Journal of Agricultural and Food Chemistry
Tony K McGhie, Sébastien Hudault, Rona C M Lunken, John T Christeller
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...
January 11, 2012: Journal of Agricultural and Food Chemistry
You-sheng Cehn, Kun Zhang, Su-qing Zhao, Jian-hong Zhang
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)...
May 2010: Zhong Yao Cai, Zhongyaocai, Journal of Chinese Medicinal Materials
X Rabasseda
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...
August 2010: Drugs of Today
Pu Liu, Ruixue Deng, Hongquan Duan, Weiping Yin
OBJECTIVE: To study the chemical constituents of Phlomis umbrosa. METHOD: Chemical constituents were isolated by repeated column chromatography (Toyopearl HW-40C and preparative HPLC). The structures were elucidated on the basis of spectral data analysis. RESULT: Thirteen compounds were identified as oleanolic acid (1), corosolic acid (2), hederagenin (3), arjunolic acid (4), belleric acid (5), 3beta-hydroxy-29-al-12-en-28-oleanoic acid (6), butyrospermol (7), beta-sitosterol (8), daucosterol (9), caffeic acid (10), vanillic acid (11), p-hydroxy-benzoic acid (12), 3, 4-dihydroxy-benzoic acid (13)...
April 2009: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
Victor Kuete, Frédéric Nana, Bathélémy Ngameni, Armelle Tsafack Mbaveng, Félix Keumedjio, Bonaventure Tchaleu Ngadjui
AIM OF THE STUDY: This study was designed to investigate the antimicrobial activities of the methanol extracts from the stem bark of Ficus ovata (FOB), fractions (FOB1-6) and compounds isolated following bio-guided fractionation [3-friedelanone (1), taraxeryl acetate (2), betulinic acid (3), oleanoïc acid (4), 2-hydroxyisoprunetin (5), 6,7-(2-isopropenyl furo)-5,2,4-trihydroxyisoflavone (6), Cajanin (7) and protocatechuic acid (8)]. MATERIALS AND METHODS: The micro-dilution method was used for the determination of the minimal inhibition concentration (MIC) and the minimal microbicidal concentration (MMC) against fungi (two species), gram-positive (three species) and gram-negative bacteria (five species)...
July 30, 2009: Journal of Ethnopharmacology
Mário Geraldo de Carvalho, Lucilene Faustina de Oliveira Cândido, Patrícia Miranda da Costa, Ildomar Alves do Nascimento, Raimundo Braz-Filho
From the leaves and wood of Licania arianeae, ten known compounds were isolated and identified. They belong to pharmacological active triterpenes acids, including three oleanoic acids, five ursane acids, and two triterpenes saponin acids. Their structures were established by analysis of infrared, mass spectrometry, and nuclear magnetic resonance spectral data of natural triterpenes and of methyl acetyl derivatives.
July 2008: Journal of Natural Medicines
Luis C Scalon Cunha, Márcio L Andrade e Silva, Niege A J Cardoso Furtado, Adriana H C Vinhólis, Carlos H Martins, Ademar A da Silva Filho, Wilson R Cunha
Triterpene acids (ursolic, oleanoic, gypsogenic, and sumaresinolic acids) isolated from Miconia species, along with a mixture of ursolic and oleanolic acids and a mixture of maslinic and 2-a-hydroxyursolic acids, as well as ursolic acid derivatives were evaluated against the following microorganisms: Streptococcus mutans, Streptococcus mitis, Streptococcus sanguinis, Streptococcus salivarius, Streptococcus sobrinus, and Enterococcus faecalis, which are potentially responsible for the formation of dental caries in humans...
September 2007: Zeitschrift Für Naturforschung. C, A Journal of Biosciences
David Cáceres-Castillo, Gonzalo J Mena-Rejón, Roberto Cedillo-Rivera, Leovigildo Quijano
Stem bark of Hippocratea excelsa afforded six pentacyclic triterpenes, five oleanane and one ursane types. They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21beta-dihydroxy-olean-9(11),12-diene (5), 3alpha,21beta-dihydroxy-olean-12-ene (6) and 3alpha,21beta-dihydroxy-11alpha-methoxy-urs-12-ene, isolated as its diacetate derivative (7), as well as 3alpha,21beta-dihydroxy-olean-12-ene (1) previously isolated from the root bark...
February 2008: Phytochemistry
Jin Tatsuzaki, Masahiko Taniguchi, Kenneth F Bastow, Kyoko Nakagawa-Goto, Susan L Morris-Natschke, Hideji Itokawa, Kimiye Baba, Kuo-Hsiung Lee
Esterification of glycyrrhetinic acid (GA) with dehydrozingerone (DZ) resulted in a novel cytotoxic GA-DZ conjugate. Based on this exciting finding, we conjugated eleven different DZ analogs with GA or other triterpenoids, including oleanoic acid (OA) or ursolic acid (UA). In an in vitro anti-cancer assay using nine different human tumor cell lines, most of the GA-DZ conjugates showed significant potency. Particularly, compounds 5, 29, and 30 showed significant cytotoxic effects against LN-Cap, 1A9, and KB cells with ED(50) values of 0...
September 15, 2007: Bioorganic & Medicinal Chemistry
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