Journal articles: 'Oleanic acid'

1

Carvalho, Luis, and J. Seita. "A New Oleanic Acid Derivative fromSecurinega tinctoria." Planta Medica 59, no. 04 (August 1993): 369–72. http://dx.doi.org/10.1055/s-2006-959704.

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Nie, Xu-Liang, Zhong-Ping Yin, and Xin-Chen Shang-Guan. "Crystal structure of benzyl-2-oxo-oleanic acid, C37H52O4." Zeitschrift für Kristallographie - New Crystal Structures 229, no. 4 (December 1, 2014): 473–75. http://dx.doi.org/10.1515/ncrs-2014-0162.

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Su, Dan, Yu-qiao Gao, Wei-bo Dai, Ying Hu, Yan-fen Wu, and Quan-xi Mei. "Helicteric Acid, Oleanic Acid, and Betulinic Acid, Three Triterpenes fromHelicteres angustifoliaL., Inhibit Proliferation and Induce Apoptosis in HT-29 Colorectal Cancer Cells via Suppressing NF-κB and STAT3 Signaling." Evidence-Based Complementary and Alternative Medicine 2017 (2017): 1–8. http://dx.doi.org/10.1155/2017/5180707.

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Colorectal cancer (CRC) is one of the most common malignancies and most frequent cause of cancer death worldwide. The activation of both NF-κB and STAT3 signaling and the crosstalk between them play an important role in colorectal tumor.Helicteres angustifoliaL. is a type of commonly used Chinese medicinal herb and possesses a wide variety of biological activities. In the present study, we investigate the effects of three triterpenes fromH. angustifolia(HT) such as helicteric acid (HA), oleanic acid (OA), and betulinic acid (BA), on inhibiting CRC progression. Our results showed that HT extracts could decrease proliferation and induce apoptosis in HT-29 colorectal cancer cells. Moreover, HT extracts could suppress LPS-triggered phosphorylation of IKK, IκB, and NF-κB, attenuate IL-6-induced phosphorylation of JAK2 and STAT3, and suppress the expression of c-Myc, cyclin-D1, and BCL-xL, the downstream gene targets of NF-κB and STAT3. Therefore, HT extracts showed potent therapeutic and antitumor effects on CRC via inhibiting NF-κB and STAT3 signaling.

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Sogno, I., N. Vannini, G. Lorusso, R. Cammarota, D. M. Noonan, and A. Albini. "P12 Anti-angiogenic activity of a novel class of chemopreventive compounds, oleanic acid terpenoids." European Journal of Cancer Supplements 6, no. 3 (March 2008): 45. http://dx.doi.org/10.1016/s1359-6349(08)70244-1.

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Alvarado, Helen L., Ana C. Calpena, María L. Garduño-Ramírez, Raúl Ortiz, Consolación Melguizo, José C. Prados, and Beatriz Clares. "Nanoemulsion Strategy for Ursolic and Oleanic Acids Isolates from Plumeria Obtusa Improves Antioxidant and Cytotoxic Activity in Melanoma Cells." Anti-Cancer Agents in Medicinal Chemistry 18, no. 6 (November 12, 2018): 847–53. http://dx.doi.org/10.2174/1871520618666180111151846.

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Background: Triterpenoids are an important class of natural bioactive products present in many medicinal plants. Objective: The aim of present study is to investigate the antioxidant and anticarcinogenic potential of Oleanolic Acid (OA) and Ursolic Acid (UA) on B16 murine melanoma cell line isolated from Plumeria obtusa, free and loaded in a nanoemulsion (NEm) system. Methods: The nanoemulsion was characterized by dynamic light scattering, transmission electron microscopy. The viscosity was also evaluated. The antioxidant activity was determined by the reduction of 2,2-diphenyl-2- picrylhydrazyl (DPPH) free radical. In vitro proliferation studies were determined using the sulforhodamine-B method. Results: OA/UA natural mixture exhibited high percentage of inhibition of DPPH (86.06% and 85.12%, with and without irradiation). Percentages of inhibition higher than 85% in samples with and without ultraviolet irradiation were recorded when loaded in the NEm system. The natural mixture incorporated into the NEm showed cytotoxic activity from 2.9 µM, whereas the free compounds from 17.4 µM. Conclusion: We conclude that these pentacyclic triterpenes loaded in a NEm system could be considered as a new potential tool for further investigation as anticancer agents.

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Castellano, Leonardo, Rosabel S. de Correa, Eduardo Martínez, and Jose´ S. Calderon. "Oleanane Triterpenoids from Cedrela montana (Meliaceae)." Zeitschrift für Naturforschung C 57, no. 7-8 (August 1, 2002): 575–78. http://dx.doi.org/10.1515/znc-2002-7-804.

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Two new oleanane-type triterpenes, characterized as 3-oxo-11α,12α-epoxy-oleanan-28,13β- olide and 3-oxo-olean-11-en-28,13β-olide , were isolated from the fruits and seeds of Cedrela montana (Meliaceae). In addition, the known compounds oleanonic acid , a mixture of β-sitosterol and stigmasterol, and the limonoid photogedunin were also isolated. The structures of the new compounds were established by spectroscopic methods, including 2D NMR.

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Li, Sumei, Xiuhua Jia, Xintian Shen, Zhuwen Wei, Zhiyan Jiang, Yixian Liao, Yiming Guo, Xiaojun Zheng, Guohua Zhong, and Gaopeng Song. "Structure-activity relationships of 3-O-β-chacotriosyl oleanic acid derivatives as entry inhibitors for highly pathogenic H5N1 influenza virus." Bioorganic & Medicinal Chemistry 25, no. 16 (August 2017): 4384–96. http://dx.doi.org/10.1016/j.bmc.2017.06.025.

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8

Cunha, Luis C. Scalon, Márcio L. Andrade e. Silva, Niege A. J. Cardoso Furtado, Adriana H. C. Vinhólis, Carlos H. Gomes Martins, A. da Silva Filho, and Wilson R. Cunha. "Antibacterial Activity of Triterpene Acids and Semi-Synthetic Derivatives against Oral Pathogens." Zeitschrift für Naturforschung C 62, no. 9-10 (October 1, 2007): 668–72. http://dx.doi.org/10.1515/znc-2007-9-1007.

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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-α-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. The microdilution method was used for the determination of the minimum inhibitory concentration (MIC) during the evaluation of the antibacterial activity. All the isolated compounds, mixtures, and semi-synthetic derivatives displayed activity against all the tested bacteria, showing that they are promising antiplaque and anticaries agents. Ursolic and oleanolic acids displayed the most intense antibacterial effect, with MIC values ranging from 30 μg/mL to 80 μg/mL. The MIC values of ursolic acid derivatives, as well as those obtained for the mixture of ursolic and oleanolic acids showed that these compounds do not have higher antibacterial activity when compared with the activity observed with either ursolic acid or oleanolic acid alone. With regard to the structure-activity relationship of triterpene acids and derivatives, it is suggested that both hydroxy and carboxy groups present in the triterpenes are important for their antibacterial activity against oral pathogens.

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Joshi, Prashant, Omprakash Tanwar, Sujit Rambhade, Mukesh Bhaisare, and Deepti Jain. "2-D QSAR studies of steroidal natural products oleanic acid and their semisynthetic derivatives as potent protein tyrosine phosphatase 1B inhibitors." Medicinal Chemistry Research 21, no. 3 (January 7, 2011): 351–61. http://dx.doi.org/10.1007/s00044-010-9529-5.

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10

Hu, Yufang, Zhaohui Zhang, Jiaxing Li, Huabin Zhang, Lijuan Luo, and Shouzhuo Yao. "Electrochemical imprinted sensor for determination of oleanic acid based on poly (sodium 4-styrenesulfonate-co-acrylic acid)-grafted multi-walled carbon nanotubes-chitosan and cobalt hexacyanoferrate nanoparticles." Biosensors and Bioelectronics 31, no. 1 (January 2012): 190–96. http://dx.doi.org/10.1016/j.bios.2011.10.016.

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11

Hong, Yong-Deog, Dae-Sung Yoo, Mi-Hee Nam, Hyeon-Chung Kim, Si-Jun Park, Song-Seok Shin, Jong-Woo Cheon, and Young Ho Park. "Excellent Anti-aging Effects of Ursolic acid and Oleanolic acid Present in Ligustrum lucidum." Journal of the Society of Cosmetic Scientists of Korea 38, no. 2 (June 30, 2012): 181–87. http://dx.doi.org/10.15230/scsk.2012.38.2.181.

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12

Hu, Yong Nan, Qing Wang, Yu Ming Sun, Xiao Hui Li, Xin Yi Che, and Hai Hong Zhang. "Studies on In Vitro Release Performance of Hydrophilic Drugs and Lipophilic Drugs in Amphiphilic SIS-Based Hot-Melt Pressure Sensitive Adhesives." Applied Mechanics and Materials 395-396 (September 2013): 389–98. http://dx.doi.org/10.4028/www.scientific.net/amm.395-396.389.

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In order to fabricate a kind of amphiphilic hot-melt pressure sensitive adhesives (HMPSAs) suitable for transdermal drug delivery systems (TDDS) of natural medicines, SIS-based hot-melt pressure sensitive adhesives were modified by a melt-blending method, in which a kind of hydrophilic poly (ethyl acrylate-co-methyl methacrylate-co-trimethylammonioethyl methacrylate chloride) (RLPO) and polyethylene glycol 2000 (PEG2000) were utilized. Functional RLPO and its plasticizer PEG2000 worked as a hydrophilic skeleton of amphiphilic HMPSAs. SEM and FT-IR results indicated that RLPO and SIS were partially compatible with each other through n-π complex between the n electrons of the carbonyl group of RLPO and the π electrons of the benzene rings of SIS and their compound had a good thermal stability. The phase microscope images showed that PEG could improve the compatibility between RLPO phase and SIS phase. As the ratio of SIS/RLPO/PEG equaled to 1/2/1.6, their compounds obtained bi-continuous structures. Geniposide (logP<0) and oleanic acid (logP=9.0) were chosen as representatives of hydrophilic drugs and lipophilic drugs, respectively. It was observed that both hydrophilic drugs and lipophilic drugs had a continuous release in the optimized amphiphilic HMPSAs. In addition, the release behavior of hydrophilic geniposide could be controlled by adjusting the ratio of RLPO to PEG.

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13

Zhang, Chen, Fang Li, Si-Xi Wang, Zhao-Sheng Liu, and Haji Akber Aisa. "Molecularly imprinted polymers prepared using a porogenic solvent of an ionic liquid and a macromolecular crowding agent and their application in purification of oleanic acid." Analytical Methods 7, no. 24 (2015): 10256–65. http://dx.doi.org/10.1039/c5ay01960e.

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A strategy to increase the affinity of molecularly imprinted polymers (MIPs) using a novel porogenic solvent was described based on the cooperative effect of ionic liquids and macromolecular crowding agents.

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14

Kim, Saeng-Gon, Min-Jung Kim, Dong-Chun Jin, Soon-Nang Park, Eu-Gene Cho, Marcelo Oliveira Freire, Sook-Jin Jang, Young-Jin Park, and Joong-Ki Kook. "Antimicrobial Effect of Ursolic Acid and Oleanolic Acid against Methicillin-Resistant Staphylococcus aureus." Korean Journal of Microbiology 48, no. 3 (September 30, 2012): 212–15. http://dx.doi.org/10.7845/kjm.2012.029.

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15

Sime, Patricia J. "The Antifibrogenic Potential of PPARγ Ligands in Pulmonary Fibrosis." Journal of Investigative Medicine 56, no. 2 (February 1, 2008): 534–38. http://dx.doi.org/10.2310/jim.0b013e31816464e9.

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Pulmonary fibrosis is characterized by the accumulation of fibroblasts, myofibroblasts, collagen, and other extracellular matrix proteins in the interstitium of the lung, with subsequent scarring and destruction of the alveolar capillary interface. In some cases, pulmonary fibrosis is preceded by lung inflammation and can be treated with anti-inflammatory therapies. However, idiopathic pulmonary fibrosis is characterized by a relative paucity of underlying inflammation and currently has no effective treatment. There is increasing evidence that the transcription factor peroxisome proliferator-activated receptor (PPAR) γ plays an important role in controlling cell differentiation and that PPARγ ligands can modify inflammatory and fibrotic responses. Peroxisome proliferator-activated receptor γ ligands, including the thiazolidinedione class of antidiabetic drugs and novel triterpenoid compounds derived from oleanic acid, inhibit TGF-β-stimulated profibrotic differentiation of lung fibroblasts in vitro and reduce lung scarring in animal models of fibrosis. The mechanism of action of the PPARγ ligands is under investigation but seems to involve both PPARγ-dependent and PPARγ-independent pathways. These in vitro and in vivo data highlight the potentially exciting role of PPARγ ligands as novel therapies for fibrosis of the lung and other organ systems prone to scarring. Many of the synthetic PPARγ ligands are orally active, and several are currently available and Food Drug Administration approved for use in therapy of type 2 diabetes. Further research is urgently required to more clearly elucidate the mechanism of action of these drugs and to develop more potent antifibrotic agents for patients with scarring diseases for whom there are currently few effective therapies.

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El Hazzam, Khadija, Jawhar Hafsa, Mansour Sobeh, Manal Mhada, Moha Taourirte, Kamal EL Kacimi, and Abdelaziz Yasri. "An Insight into Saponins from Quinoa (Chenopodium quinoa Willd): A Review." Molecules 25, no. 5 (February 27, 2020): 1059. http://dx.doi.org/10.3390/molecules25051059.

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Saponins are an important group found in Chenopodium quinoa. They represent an obstacle for the use of quinoa as food for humans and animal feeds because of their bitter taste and toxic effects, which necessitates their elimination. Several saponins elimination methods have been examined to leach the saponins from the quinoa seeds; the wet technique remains the most used at both laboratory and industrial levels. Dry methods (heat treatment, extrusion, roasting, or mechanical abrasion) and genetic methods have also been evaluated. The extraction of quinoa saponins can be carried out by several methods; conventional technologies such as maceration and Soxhlet are the most utilized methods. However, recent research has focused on technologies to improve the efficiency of extraction. At least 40 saponin structures from quinoa have been isolated in the past 30 years, the derived molecular entities essentially being phytolaccagenic, oleanolic and serjanic acids, hederagenin, 3β,23,30 trihydroxy olean-12-en-28-oic acid, 3β-hydroxy-27-oxo-olean-12en-28-oic acid, and 3β,23,30 trihydroxy olean-12-en-28-oic acid. These metabolites exhibit a wide range of biological activities, such as molluscicidal, antifungal, anti-inflammatory, hemolytic, and cytotoxic properties.

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17

Kinuthia, Esther W., Moses K. Langat, Elizabeth M. Mwangi, and Peter K. Cheplogoi. "Constituents of Kenyan Gardenia Volkensii." Natural Product Communications 7, no. 1 (January 2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700106.

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A new triterpenoid, 3-oxo-22α-hydroxy-olean-12-en-28-oic acid (1), oleanolic acid (2) and a known iridoid, 10-hydroxy-1-oxo-7-iriden-11-oic acid methyl ester (3) have been isolated from the dichloromethane extract of the dried seeds of Gardenia volkensii. Their structures were established by 1D and 2D NMR spectroscopic and MS methods.

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18

Vasconcelos, Maria Anita L., Vanessa A. Royo, Daniele S. Ferreira, Antonio E. Miller Crotti, Márcio L. Andrade e Silva, José Carlos T. Carvalho, Jairo Kenupp Bastos, and Wilson R. Cunha. "In vivo Analgesic and Anti-Inflammatory Activities of Ursolic Acid and Oleanoic Acid from Miconia albicans (Melastomataceae)." Zeitschrift für Naturforschung C 61, no. 7-8 (August 1, 2006): 477–82. http://dx.doi.org/10.1515/znc-2006-7-803.

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The aim of this work was to use in vivo models to evaluate the analgesic and anti-inflammatory activities of ursolic acid (UA) and oleanoic acid (OA), the major compounds isolated as an isomeric mixture from the crude methylene chloride extract of Miconia albicans aerial parts, in an attempt to clarify if these compounds are responsible for the analgesic properties displayed by this plant. Ursolic acid inhibited abdominal constriction in a dose-dependent manner, and the result obtained at a content of 40 mg kg-1 was similar to that produced by administration of acetylsalicylic acid at a content of 100 mg kg-1. Both acids reduced the number of paw licks in the second phase of the formalin test, and both of them displayed a significant anti-inflammatory effect at a content of 40 mg kg-1. It is noteworthy that the administration of the isolated mixture, containing 65% ursolic acid/35% oleanolic acid, did not display significant analgesic and anti-inflammatory activities. On the basis of the obtained results, considering that the mixture of UA and OA was poorly active, it is suggested that other compounds, rather than UA and OA, should be responsible for the evaluated activities in the crude extract, since the crude extract samples displayed good activities.

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Yang, Ke Di, Yue Juan Li, Li Ge, and Zu Zeng Qin. "Isolation of Triterpenoids from Catunaregam spinosa." Advanced Materials Research 236-238 (May 2011): 1731–37. http://dx.doi.org/10.4028/www.scientific.net/amr.236-238.1731.

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Investigation on the antifeedant activity and toxicity of Catunaregam Spinosa (Rubiaceae)fruits revealed that the n-butanol fraction from methanolic extractof Catunaregam Spinosa fruits showed effective antifeedant activity and toxicity against the larvae of Pieris rapae and Plutella xylostella. Continued chemical investigation on the n-butanol fraction yielded five triterpenoids. Use of NMR, MS and sugar analysis gave structures of three triterpenoid saponins with branched monosaccharide chain as 3-O-[β-D-glucopyranosyl-(1→3)-β-D-6-O-methyl-glucuronopyranosyl oxy]-2β-hydroxy-olean-12-en-28-oic acid (1), 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyran -osyl]-olean-12-en-28-oic acid (2), 3-O-[β-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl- (1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-12-en-28-oic acid (3), and along with triterpenoids as Oleanolic acid (4), 3β,23-dihydroxy-olean-12-ene-28-oic acid (5), respectively.

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20

Spivak, Anna, Darya Nedopekina, Lilya Dzhemileva, and Rezeda Khalitova. "C-28 Esters of Triterpenoid Acids Bearing Tris(hydroxymethyl)aminomethane: Synthesis and Anticancer/Antimicrobial Activity." Proceedings 41, no. 1 (November 14, 2019): 45. http://dx.doi.org/10.3390/ecsoc-23-06493.

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Widespread secondary plant metabolites (betulinic, ursolic, and oleanolic acids) are promising scaffolds for the discovery of new drugs. Among the many semi-synthetic derivatives of lupane triterpenoids known today, the anticancer agent C-28 ester of betulinic acid with tris(hydroxymethyl)aminomethane (NVX-207) has been actively studied. This betulinic acid derivative, which has shown significant antitumor activity in vitro and in vivo against various malignant tumors, is a candidate drug. It is known that modification of the structure of the triterpenoid skeleton can lead to significant changes in biological properties. In this regard, we have synthesized C-28 esters of ursolic and oleanolic acids and C20-29 hydrogenated betulinic acid bearing tris(hydroxymethyl)aminomethane (TRIS), and transformed them into guanidinium salts by guanylation of the primary amino group in a branched ester fragment under the action of 1H-pyrazole-1-carboxamidine hydrochloride. The obtained compounds were tested in in vitro experiments on three human cancer cell lines. The presence of the TRIS-fragment in the triterpenoid conjugates markedly enhanced the cytotoxic action as compared to the parent compounds, dihydrobetulinic, ursolic, and oleanolic acids (IC50 values 2.8–7.6 μM for Jurkat cells and 1.1–6.8 μM for U937 cells), while the correlation between the cytotoxic activity and the chemical structure of the triterpenoid skeleton was not observed. Extended biological testing of these triterpenoids by using flow cytometry analysis showed that antitumor activity of compounds is caused by apoptotic processes and induction of cell cycle arrest in the S-phase. New triterpenoids were also tested for their antimicrobial activity against the growth of four bacterial strains (Escherichia coli, Acinetobacter baumannii, Pseudomonas aeruginosa, and Staphylococcus aureus (MRSA)) and two fungal strains (Candida albicans and Cryptococcus neoformans). The TRIS-dihydrobetulinic acid conjugate and its guanidinium derivative did not exhibit antimicrobial properties. The corresponding ursane and oleane-skeleton pentacyclic tritrerpenoids showed good bacteriostatic activity against methicillin-resistant S. aureus (MICs 4 and 32 μg/mL) and excellent antifungal effect against Cryptococcus neoformans and Candida albicans (MICs 4 and 0.25 μg/mL).

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21

Basir, Dasril, Julinar Julinar, Eva Agustriana, and Budi Untari. "Oxidation and Acetylation of Ursolic and Oleanolic Acids Isolated from Fragraea fragrans fruits; Antiproliferation of P388 Leukemia Cells." Indonesian Journal of Chemistry 14, no. 3 (October 30, 2014): 269–76. http://dx.doi.org/10.22146/ijc.21238.

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An interesting natural product chemistry aspect of Fragraea fragrans is that their fruits are richness with ursolic acid and its isomer oleanolic acid (3.05% of dried powder). As our continuous work on these inseparable structural isomeric triterpenes, this paper reports that 51.0% of inseparable 3-oxo-ursolic[3-oxo-oleanolic] acids and 48.6% of inseparable 3-acethyl-ursolic [3-acethyl-oleanolic] acids have already been made from those triterpenes as starting materials of the oxidized and acetylated compounds and evaluated their activity against P388 leukemia cells. The activity of 3-oxo-ursolic [3-oxo-oleanolic] acids with IC50 = 18.6 µg/mL exhibited three-fold more potent against P388 leukemia cell proliferations compared to ursolic [oleanolic] acids with IC50 = 53.5 µg/mL; while the 3-acethyl-ursolic [3-acethyl-oleanolic] acids with IC50 = 37.9 µg/mL showed two-fold more potent then their parent triterpenes (IC50 = 53.5 µg/mL) in the inhibition of P388 leukemia cell growth.

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Benayache, Feryal, Massimiliano D'Ambola, Roberta Cotugno, Massika Chaouche, Samir Benayache, Fadila Benayache, Alessandra Braca, and Nunziatina De Tommasi. "A New Triterpene Glucoside from Genista numidica." Natural Product Communications 13, no. 9 (September 2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300902.

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A new oleanolic acid triterpene glucoside, 3- O-β-D-glucopyranosyl-3β,21β,28-trihydroxy-olean-12-en-27-oic acid (1), has been isolated together with twelve known compounds from the chloroform and ethyl acetate extracts of Genista numidica Spach (Fabaceae) aerial parts. The structures were elucidated by spectroscopic and spectrometric analyses, mainly 1D-, 2D-NMR and MS data, and comparison with the literature. The antiproliferative activity of isolates was investigated on Jurkat, HeLa, and MCF7 cell lines. The most active triterpene, 3- O-β-D-glucopyranosyl-olean-12-en-3β,27,28,29-tetraol, showed activity in all cell lines. Further studies revealed that this compound induced in HeLa cells a cytostatic response.

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KUREK, ANNA, KATARZYNA MARKOWSKA, ANNA M. GRUDNIAK, WIRGINIA JANISZOWSKA, and KRYSTYNA I. WOLSKA. "The Effect of Oleanolic and Ursolic Acids on the Hemolytic Properties and Biofilm Formation of Listeria monocytogenes." Polish Journal of Microbiology 63, no. 1 (2014): 21–25. http://dx.doi.org/10.33073/pjm-2014-003.

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Oleanolic acid and ursolic acid are pentacyclic triterpenoids isolated from a variety of medicinal plants, which have antibacterial activity. Listeria monocytogenes is a Gram-positive facultative pathogen, being the causative agent of listeriosis. The present study was carried out to evaluate the in vitro effect of sub-inhibitory concentrations of both triterpene acids on the pathogenicity determinants of L. monocytogenes: their hemolytic activity and biofilm forming ability. Oleanolic and ursolic acids inhibited listeriolysin O activity without influencing toxin secretion. Biofilm formation, and the viability of L. monocytogenes cells in biofilms was diminished by both compounds. Thus, both acids affected L. monocytogenes virulence. It was also demonstrated that oleanolic acid bound to the peptidoglycan of L. monocytogenes and this interaction was influenced by teichoic acids.

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Yoon, Yo-Han, and Kyoung-Hee Choi. "Identification of Inhibitory Effect on Streptococcus mutans by Oleanolic Acid." Journal of Life Science 20, no. 3 (March 30, 2010): 321–25. http://dx.doi.org/10.5352/jls.2010.20.3.321.

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Attard, Everaldo, and Henrietta Attard. "The Potential Angiotensin-Converting Enzyme Inhibitory Activity of Oleanolic Acid in the Hydroethanolic Extract of Crataegus monogyna Jacq." Natural Product Communications 1, no. 5 (May 2006): 1934578X0600100. http://dx.doi.org/10.1177/1934578x0600100507.

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The hydroethanolic extract of Crataegus monogyna was studied for its chemical constitution and angiotensin-converting enzyme (ACE) inhibitory activity. The extract contained triterpenic acids, flavonoids and coumarins. The ACE inhibitory activity was studied using captropril, as a control drug, and oleanolic acid, as a constituent of the hydroethanolic extract and a member of the triterpenic acid group. The hydroethanolic extract and oleanolic acid showed higher IC50 values (335.00 μg/mL and 3.61 μM, respectively) in comparison to captopril (46.9 nM). However, these results indicate the anti-ACE activity of oleanolic acid and the triterpenic acids, which has not been demonstrated earlier for hawthorn extracts. In previous studies, the ACE inhibitory activity of C. monogyna extracts was always attributed to flavonoids and proanthocyanidins.

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Mučaji, P., and M. Nagy. "Contribution to the TLC separation of ursolic and oleanolic acid mixture." Acta Facultatis Pharmaceuticae Universitatis Comenianae 58, no. 1 (January 1, 2011): 56–61. http://dx.doi.org/10.2478/v10219-011-0006-0.

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Contribution to the TLC separation of ursolic and oleanolic acid mixtureThe aim of the study was to develop a rapid, simple, effective and reproducible TLC method for separation of a naturally occurring mixture of ursolic and oleanolic acids. Because of the similarity of chemical structures,in situderivatisation by iodine was necessary to separate these triterpenic acids. Separation was achieved on silica gel plates. After derivatisation, a chromatographic plate was developed with the mobile phase consisting of light petrol, ethyl acetate and acetone (8.2:1.8:0.1, v/v/v) following visualisation by spraying with sulphuric acid in diethylether (25%, v/v) and heating to 120°C for 5 min. The method used enabled chromatographical differentiation of ursolic and oleanolic acid mixtures in all tested mutual ratios.

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27

Kuroda, Minpei, Taku Aoshima, Mitsue Haraguchi, Maria Cláudia Marx Young, Hiroshi Sakagami, and Yoshihiro Mimaki. "New Oleanane Glycosides from the Roots of Gomphrena macrocephala." Natural Product Communications 1, no. 6 (June 2006): 1934578X0600100. http://dx.doi.org/10.1177/1934578x0600100601.

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Six new (1–6) and one known (7) oleanane glycosides have been isolated from the roots of Gomphrena macrocephala. On the basis of 1D- and 2D-NMR spectroscopic data and the results of hydrolysis, the structures of 1–6 were determined to be 3β-[(O-β-D-glucuronopyranosyl)oxy]oleana-11,13-dien-28-oic acid (1), 3β-[(O-β-D-galactopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl)oxy]oleana-11,13-dien-28-oic acid (2), 3β-[(O-β-D-glucuronopyranosyl)oxy]oleana-9,12-dien-28-oic acid β-D-glucopyranosyl ester (3), 3β-[(O-β-D-galactopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl)oxy]oleana-9,12-dien-28-oic acid β-D-glucopyranosyl ester (4), 3β-[(O-β-D-galactopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl)oxy]-11-oxo-olean-12-en-28-oic acid β-D-glucopyranosyl ester (5), and 3β-[(O-β-D-galactopyranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl)oxy]-11α-hydroxyolean-12-en-28-oic acid β-D-glucopyranosyl ester (6), respectively. Although 1–7 did not show apparent cytotoxicity against human oral squamous cell carcinoma (HSC-2) cells and normal human pulp cells (HPC), the aglycones 1a and 3a of 1 and 3 exhibited tumor-specific cytotoxicity against HSC-2 cells, and the IC50 value of 3a against HSC-2 cells was almost equal to that of etoposide, used as a positive control.

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Mukherjee, Tulika, Tapas Sarkar, Piyali Paul, Ajit K. Chakraborty, Parasuraman Jaisankar, and Siba Brata Mukhopadhyay. "Putralone, a Novel 10α-Hydroxy-25-nor D:A Friedo-Oleanane Triterpenoid from Putranjiva Roxburghii." Natural Product Communications 7, no. 4 (April 2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700424.

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Chemical investigation of the leaves of Putranjiva roxburghii has resulted in the isolation of two new triterpenoids, putralone, a novel 10α-hydroxy-25-nor D:A friedo-olean-9(11)-en-3 one and 3β-acetoxy-cycloart-24-en-23-one, along with a rare hopanoid, adian-5-en-3β,29-diol. Other known triterpenoids isolated from this plant are 3β-acetoxy-adian-5-ene, putrol, putrone, putranjivadione, roxburghonic acid, friedelin, friedlan-3α-ol, oleanolic acid and erythrodiol. Interestingly, putralone is the first example of a naturally occurring nor friedo-oleanane triterpenoid having a hydroxyl functionality at the C-10 position.

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Hossain, Rashadul, Rajia Sultana, Aychout Adhikari, Muhammad Iqbal Choudhary, Yusuff Ali, and Shahed Zaman. "New Ursane Triterpene from the Fruits of Terminalia arjuna." Natural Product Communications 9, no. 3 (March 2014): 1934578X1400900. http://dx.doi.org/10.1177/1934578x1400900323.

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A new ursane triterpene, torment (2 α,3 β,19 α-trihydroxyurs-12-en) (1), was isolated from the fruits of Terminalia arjuna along with four known ursane and oleane triterpenes. The structures were established on the basis of extensive NMR (1D & 2D) and MS (EI & ESI) studies. Tormentic acid (2), 19α-hydroxy asiatic acid (3) and olean-12-en-2 α,3 β-diol (4) were isolated for the first time from this species. Compounds 1 and 2 lacked significant enzyme inhibition, cytotoxicity, immunomodulatory and antiglycation activities.

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Castrejón-Jiménez, Nayeli Shantal, Kahiry Leyva-Paredes, Shantal Lizbeth Baltierra-Uribe, Juan Castillo-Cruz, Marcia Campillo-Navarro, Alma Delia Hernández-Pérez, Alexandra Berenice Luna-Angulo, et al. "Ursolic and Oleanolic Acids Induce Mitophagy in A549 Human Lung Cancer Cells." Molecules 24, no. 19 (September 23, 2019): 3444. http://dx.doi.org/10.3390/molecules24193444.

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Ursolic and oleanolic acids are natural isomeric triterpenes known for their anticancer activity. Here, we investigated the effect of triterpenes on the viability of A549 human lung cancer cells and the role of autophagy in their activity. The induction of autophagy, the mitochondrial changes and signaling pathway stimulated by triterpenes were systematically explored by confocal microscopy and western blotting. Ursolic and oleanolic acids induce autophagy in A549 cells. Ursolic acid activates AKT/mTOR pathways and oleanolic acid triggers a pathway independent on AKT. Both acids promote many mitochondrial changes, suggesting that mitochondria are targets of autophagy in a process known as mitophagy. The PINK1/Parkin axis is a pathway usually associated with mitophagy, however, the mitophagy induced by ursolic or oleanolic acid is just dependent on PINK1. Moreover, both acids induce an ROS production. The blockage of autophagy with wortmannin is responsible for a decrease of mitochondrial membrane potential (Δψ) and cell death. The wortmannin treatment causes an over-increase of p62 and Nrf2 proteins promote a detoxifying effect to rescue cells from the death conducted by ROS. In conclusion, the mitophagy and p62 protein play an important function as a survival mechanism in A549 cells and could be target to therapeutic control.

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Choi, Kyoung-Hee, Sejeong Kim, and Yohan Yoon. "Antimicrobial Activity of Oleanolic Acid for Foodborne Bacteria." Journal of Food Hygiene and Safety 30, no. 1 (March 30, 2015): 98–102. http://dx.doi.org/10.13103/jfhs.2015.30.1.98.

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Sommerwerk, Sven, Lucie Heller, Immo Serbian, and René Csuk. "Straightforward partial synthesis of four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids from oleanolic acid." Tetrahedron 71, no. 45 (November 2015): 8528–34. http://dx.doi.org/10.1016/j.tet.2015.09.037.

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Pollier, Jacob, and Alain Goossens. "Oleanolic acid." Phytochemistry 77 (May 2012): 10–15. http://dx.doi.org/10.1016/j.phytochem.2011.12.022.

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Singh, G. B., S. Singh, and S. Bani. "Oleanolic Acid." Drugs of the Future 19, no. 5 (1994): 450. http://dx.doi.org/10.1358/dof.1994.019.05.248615.

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35

Kang, Hyung Seok, Ji-Eun Park, Young-Jin Lee, Ih-Seop Chang, Yong-Il Chung, and Giyoong Tae. "Preparation of Liposomes Containing Oleanolic Acid via Micelle-to-Vesicle Transition." Journal of Nanoscience and Nanotechnology 7, no. 11 (November 1, 2007): 3944–48. http://dx.doi.org/10.1166/jnn.2007.099.

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Micelle-to-vesicle transition method was used to make liposomes containing oleanolic acid. First, the solubilization of potassium salt of oleanolic acid at basic condition by micelle formation was confirmed. Using the soluble state of oleanolic acid at basic condition, liposomes containing oleanolic acid was prepared by adjusting pH. After making homogeneous aqueous mixture of potassium salt of oleanolic acid and lecithin in basic condition, the solution was neutralized to produce the lecithinbased liposomes that contain oleanolic acid inside the lipid bilayers. The optimal loading of oleanolic acid to lecithin (about 25 mole%) was found to exist to produce liposomal suspension of small size without homogenization step. Electron microscopy and dynamic light scattering studies showed that the narrowly distributed, reconstituted oleanolic acid-containing liposomes were prepared without severe mechanical treatment.

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36

Palu, Doreen, Ange Bighelli, Joseph Casanova, and Mathieu Paoli. "Identification and Quantitation of Ursolic and Oleanolic Acids in Ilex aquifolium L. Leaf Extracts Using 13C and 1H-NMR Spectroscopy." Molecules 24, no. 23 (December 3, 2019): 4413. http://dx.doi.org/10.3390/molecules24234413.

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Leaves of Ilex aquifolium L. have been used for their therapeutic properties. In previous studies, components contained in the leaves were first isolated by various chromatographic techniques. Then, quantitation of oleanolic and ursolic acids, which are responsible for the biological and therapeutic activities of the plant, was performed by HPLC, HPTLC, and somewhat by GC-MS. Our objective was to develop a simple method that allows the identification of compounds contained in the leaves of Corsican I. aquifolium and to quantify ursolic and oleanolic acids. Leaves were successively extracted with hexane and dichloromethane. The extracts were chromatographed on silica gel and the fractions of column chromatography submitted to 13C-NMR analysis, following a computerized method developed in the laboratory. 13C-NMR allowed the identification of various triterpenes including ursolic acid and oleanolic acid. Quantitation of both acids was achieved, for the first time, by 1H-NMR after validation of the method (accuracy, precision, linearity, limit of detection and limit of quantitation). Ursolic and oleanolic acids accounted for 55.3% and 20.8% of the dichloromethane extract, respectively. This represents 1.3% and 0.5% of the mass of dried leaves. 1H-NMR spectroscopy appeared as a powerful tool for a rapid quantitation of biologically active compounds from I. aquifolium.

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Feng, Anjie, Shanjing Yang, Yue Sun, Li Zhang, Fumin Bo, and Lingjun Li. "Development and Evaluation of Oleanolic Acid Dosage Forms and Its Derivatives." BioMed Research International 2020 (November 25, 2020): 1–16. http://dx.doi.org/10.1155/2020/1308749.

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Oleanolic acid is a pentacyclic triterpenoid compound that exists widely in medicinal herbs and other plants. Because of the extensive pharmacological activity, oleanolic acid has attracted more and more attention. However, the structural characteristics of oleanolic acid prevent it from being directly made into new drugs, which limits the application of oleanolic acid. Through the application of modern preparation techniques and methods, different oleanolic acid dosage forms and derivatives have been designed and synthesized. These techniques can improve the water solubility and bioavailability of oleanolic acid and lay a foundation for the new drug development. In this review, the recent progress in understanding the oleanolic acid dosage forms and its derivatives are discussed. Furthermore, these products were evaluated comprehensively from the perspective of characterization and pharmacokinetics, and this work may provide ideas and references for the development of oleanolic acid preparations.

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Misra, Suniti, Ashis K. Dutta, A. Choudhury, and Amitabha Ghosh. "Oxidation of oleanolic acid ofAvicennia officinalis leaves to oleanonic acid in the natural environment of Sunderban mangrove ecosystem." Journal of Chemical Ecology 11, no. 3 (March 1985): 339–42. http://dx.doi.org/10.1007/bf01411420.

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Claro-Cala, Carmen Maria, Jose Carlos Quintela, Marta Pérez-Montero, Javier Miñano, María Alvarez de Sotomayor, María Dolores Herrera, and Rosalía Rodríguez-Rodríguez. "Pomace Olive Oil Concentrated in Triterpenic Acids Restores Vascular Function, Glucose Tolerance and Obesity Progression in Mice." Nutrients 12, no. 2 (January 26, 2020): 323. http://dx.doi.org/10.3390/nu12020323.

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Pomace olive oil, an olive oil sub-product, is a promising source of bioactive triterpenoids such as oleanolic acid and maslinic acid. Considering the vascular actions of pomace olive oil and the potential effects of the isolated oleanolic acid on metabolic complications of obesity, this study investigates for the first time the dietary intervention with a pomace olive oil with high concentrations of the triterpenic acids (POCTA), oleanolic and maslinic acid, during diet-induced obesity in mice. The results demonstrate that obese mice, when switched to a POCTA-diet for 10 weeks, show a substantial reduction of body weight, insulin resistance, adipose tissue inflammation, and particularly, improvement of vascular function despite high caloric intake. This study reveals the potential of a functional food based on pomace olive oil and its triterpenic fraction against obesity progression. Our data also contribute to understanding the health-promoting effects attributable to the Mediterranean diet.

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M, Resende, C., Barreto A. S, Pinto, P. R., Nascimento C. C. H. C, Vasconcelos, S. D. D. De, Azevedo, L. A.C., Stephens P. R. S., et al. "TERPENOIDS AND PHYTOSTEROLS ISOLATED FROM PLUMERIA RUBRA L., FORM ACUTIFOLIA (AIT) WOODSON AND ITS FUNGUS PARASITE COLESPORIUM PLUMERIAE." Asian Journal of Pharmaceutical Research and Development 6, no. 6 (December 12, 2018): 15–22. http://dx.doi.org/10.22270/ajprd.v6i6.428.

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The hexane and ethyl acetate extracts of the leaves from Plumeria rubra L., form acutifolia (Ait) Woodson and the methanolic extract from the fungus Coleosporium plumeriae Pat. were analized by high resolution gas chromatography (HRGC) and by high resolution gas chromatography coupled to mass spectrometes (GC-MS). The identification of the chemical constituintes is these extracts has been made by the automatic comparison of the mass spectra obtained standards within the NBS, Wiley and Wiley 275T librarys supplied with the mass spectrometer and by analized of the principal fragmentations. Phytochemical studies of the hexane and ethyl acetate extracts of the leaves showed nine terpenoids (5-ergosten-3b-ol, 5,22-stigmastadien-3b-ol, 4-stigmasten-3-one, 5-stigmasten-3b-ol, 12-ursen-3b-ol, 12-oleanen-3b-ol, 12-oleanen-3-one-28-oic acid, ursolic acid and 3b-acetoxy-12-oleanen-28-oic acid). The compounds 5-ergosten-3b-ol, 4-stigmasten-3-one, 12-oleanen-3-one-28-oic acid, ursolic acid and 3b-acetoxy-12-oleanen-28-oic acid have been described for the first time from Plumeria rubra L., forma acutifolia (Ait) Woodson. From the methanolic extract of spores of the fungus Coleosporium plumeriae Pat were isolated 5-stigmasten-3b-ol, methyl esters of long chain fatty acids (C18:0, principally) and one aromatic compound, N-methyl toluenesulfonamide. No previous phytochemical studies of this fungus have been reported.

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Khera, Smriti, Gloria Montenegro, and Barbara Timmermann. "Phytochemical Investigations of an Antitubercular Extract of Chilean Myrcianthes coquimbensis and Related Populations." Natural Product Communications 2, no. 10 (October 2007): 1934578X0700201. http://dx.doi.org/10.1177/1934578x0700201002.

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The CH2Cl2-MeOH (1:1) extract of a Chilean plant Myrcianthes coquimbensis (Barnéoud) Landrum et Grifo was found to inhibit the growth of Mycobacterium tuberculosis by 73% at a concentration of 50 μg/mL. The bioassay guided separation of this extract led to the isolation of a new monoterpene (1 S,3 S,4 R)-1-methyl-4-(1-methylethenyl)-1,3-cyclohexanediol (3β-hydroxy- cis-β-terpineol, 1), along with oleanolic acid, 3β-caffeoyl-olean-12-en-28-oic acid, trans-(+)-sobrerol, epi-catechin, and catechin. The structure of 1 was determined by GC/MS, and 1D and 2D NMR spectroscopic experiments, and its absolute configuration was established by Mosher's esterification. The antitubercular activities of all isolates were evaluated using the microplate alamar blue assay (MABA). Oleanolic acid was determined to be active with an MIC value of 65.04 μM in MABA and low cytotoxicity to African green monkey vero cells, with an IC50 value of >224.5 μM, whereas all other isolates were inactive. The CH2Cl2-MeOH (1:1) extracts of two additional populations of M. coquimbensis procured from different regions in Chile have also been analyzed by LC/MS and the compounds isolated have been identified in these extracts based on retention time, observed LC/MS parent ion, and MS/MS fragmentation pattern.

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42

Geană, Elisabeta-Irina, Corina Teodora Ciucure, Roxana Elena Ionete, Alexandru Ciocârlan, Aculina Aricu, Anton Ficai, and Ecaterina Andronescu. "Profiling of Phenolic Compounds and Triterpene Acids of Twelve Apple (Malus domestica Borkh.) Cultivars." Foods 10, no. 2 (January 28, 2021): 267. http://dx.doi.org/10.3390/foods10020267.

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Apple (Malus domestica Borkh.), a popular and widely cultivated fruit world-wide, contains bioactive compounds responsible for their health benefits. Here we report the amounts of some bioactive compounds: two major triterpenes (oleanolic and ursolic acids) and polyphenols (phenolic acids, flavan-3-ols, flavonoids and t-resveratrol), together with bioactive properties of twelve apple cultivars measured by chromatographic and spectrophotometric methods. Significant variations were found comparing the bioactive potential of the investigated cultivars. High contents of phenolic acids were identified in the Montuan, Golden Delicious and Cretesc cultivars, while the most flavonoid dominant was the Richard cultivar. Starkrimson, Jonatan, Beliy Naliv and Richard cultivars present higher antioxidant capacity. Oleanolic acid ranged from 11 to 83 mg/g apple extract, while ursolic acid ranged from 55 to 436 mg/g apple extract, with higher amounts in Richard and Montuan cultivars. Principal component analysis (PCA) and hierarchical cluster analysis (HCA) allowed the discrimination of apple cultivars depending on polyphenolic and triterpene acids composition. Caffeic acid, gallic acid and epicatechin were identified as the main bioactive compounds in Starkrimson, Jonathan, Beliy Naliv and Richard cultivars, while ursolic and oleanolic acids were identified in high amounts in Richard, Montuan, Golden Delicious, Idared and Beliy Naliv apple cultivars. The results obtained in this study will contribute to the understanding of the bioactive composition of apples as well as the importance of their capitalization to obtain value-added products that promote human health.

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Kim, Se-Won, Chang-Ho Lee, Hee-Kung Jung, Sung-Sin Jo, Hong-Ki Lee, and Yong-Soon Park. "Effects of Oleanolic Acid and its Derivatives on the Differentiation of MC3T3-E1 Osteoblastic Cell." Korean Journal of Medicinal Crop Science 19, no. 6 (December 30, 2011): 491–500. http://dx.doi.org/10.7783/kjmcs.2011.19.6.491.

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Yang, J., J. W. Quail, and Z. Jia. "Succinyl Oleanolic Acid." Acta Crystallographica Section C Crystal Structure Communications 53, no. 3 (March 15, 1997): 349–51. http://dx.doi.org/10.1107/s0108270196013923.

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Dohnal, Barbara. "Investigations on some metabolites of Tecoma stans Juss. callus tissue. Part III. Chromatographical search for iridoids, phenolic acids, terpenoids and sugars." Acta Societatis Botanicorum Poloniae 46, no. 2 (2015): 187–99. http://dx.doi.org/10.5586/asbp.1977.015.

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Tissus cultures of <i>Tecoma stans</i> Juss. cultivated on modified Murashige-Skoog medium (RT-k) were phytochemically analysed by means of chromatographical methods (PC, TLC). The following products were found as metabolites: phenolic acids - chlorogenics, caffeic, ferulic, vanillic, o-coumaric and sinapic; steroids - β-sitosterol; triterpenes - ursolic and oleanolic acids, α-amyrine; sugars - glucose, fructose, sucrose, xylose. Meso-inositol was isolated in 0.8% yield. In intact plant leaves, some differences concerning the content and/or number of individual compounds were observed, namely: lack of sinapic acid and occurrence of p-coumaric acid, lower content of β-sitosterol, lack of oleanolic acid, occurrence of β-amyrine and of one unidentified triterpenoid, lack of xylose, occurrence of maltose, raffinose, and stachiose. The level of mesoinositol inn leaves was distincly lower than in the callus tissues. Neither in callus tissues nor in leaves iridoid glycosides were found.

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Spivak, Anna, Rezeda Khalitova, Darya Nedopekina, Lilya Dzhemileva, Milyausha Yunusbaeva, Victor Odinokov, Vladimir D’yakonov, and Usein Dzhemilev. "Synthesis and Evaluation of Anticancer Activities of Novel C-28 Guanidine-Functionalized Triterpene Acid Derivatives." Molecules 23, no. 11 (November 16, 2018): 3000. http://dx.doi.org/10.3390/molecules23113000.

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Triterpene acids, namely, 20,29-dihydrobetulinic acid (BA), ursolic acid (UA) and oleanolic acid (OA) were converted into C-28-amino-functionalized triterpenoids 4–7, 8a, 15, 18 and 20. These compounds served as precursors for the synthesis of novel guanidine-functionalized triterpene acid derivatives 9b–12b, 15c, 18c and 20c. The influence of the guanidine group on the antitumor properties of triterpenoids was investigated. The cytotoxicity was tested on five human tumor cell lines (Jurkat, K562, U937, HEK, and Hela), and compared with the tests on normal human fibroblasts. The antitumor activities of the most tested guanidine derivatives was lower, than that of corresponding amines, but triterpenoids with the guanidine group were less toxic towards human fibroblasts. The introduction of the tris(hydroxymethyl)aminomethane moiety into the molecules of triterpene acids markedly enhanced the cytotoxic activity of the resulting conjugates 15, 15c, 18b,c and 20b,c irrespective of the triterpene skeleton type. The dihydrobetulinic acid amine 15, its guanidinium derivative 15c and guanidinium derivatives of ursolic and oleanolic acids 18c and 20c were selected for extended biological investigations in Jurkat cells, which demonstrated that the antitumor activity of these compounds is mediated by induction of cell cycle arrest at the S-phase and apoptosis.

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Rashmi, Rameshwar Dayal, and Akito Nagatsu. "Three Oleanolic Acid Glycosides from the Seeds of Achyranthes aspera." Natural Product Communications 2, no. 7 (July 2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200704.

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From the seeds of Achyranthes aspera three triterpenoid glycosides were isolated and their structures elucidated on the basis of NMR spectroscopic, mass spectrometric and degradative studies as α-L-rhamnopyranosyl-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-oleanolic acid, α-L-rhamnopyranosyl-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-oleanolic acid-28- O-β-D-glucopyranoside and α-L-rhamnopyranosyl-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-oleanolic acid-28- O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside.

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48

Jung, Suhan, Sanghoon Lee, and Kwang Suk Ko. "Effects of Oleanolic Acid and Hederagenin on Acute Alcohol-Induced Hepatotoxicity in Mice." Journal of the Korean Society of Food Science and Nutrition 45, no. 3 (March 31, 2016): 307–12. http://dx.doi.org/10.3746/jkfn.2016.45.3.307.

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Froelich, Anna, and Andrzej K. Gzella. "Oleanolic acid ethanol monosolvate." Acta Crystallographica Section E Structure Reports Online 66, no. 11 (October 9, 2010): o2790. http://dx.doi.org/10.1107/s1600536810039929.

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Zhao, Dapeng, and Zhongqiu Luan. "Oleanolic Acid Attenuates Renal Fibrosis through TGF-β/Smad Pathway in a Rat Model of Unilateral Ureteral Obstruction." Evidence-Based Complementary and Alternative Medicine 2020 (March 30, 2020): 1–8. http://dx.doi.org/10.1155/2020/2085303.

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Renal fibrosis is a common final pathological process in the progression of kidney disease. Oleanolic acid is a bioactive pentacyclic triterpenoid and is widely found in medicinal herbs around the world. In this study, we explored the effect of oleanolic acid on renal fibrosis and the underlying molecular mechanisms by using a rat model of unilateral ureteral obstruction (UUO). Male Sprague-Dawley rats were orally administered with oleanolic acid (6 mg/kg/d) or vehicle (olive oil) for 21 days after the UUO surgery. Upon termination, urine and blood were collected for renal function analysis, and kidneys were harvested for pathological analysis by using hematoxylin-eosin and Masson trichrome staining. Changes of extracellular matrix mRNA expressions and TGF-β/Smad signaling in the kidneys were also determined. As a result, oleanolic acid significantly reduced the kidney index, the level of serum creatinine and blood urea nitrogen, and the urinary level of microalbumin, α1-microglobulin, and N-acetyl-β-glucosaminidase. Masson trichrome staining showed significantly less collagen deposition in the UUO rats with oleanolic acid treatment. Diminished mRNA expressions of collagen I, collagen III, fibronectin, and α-SMA in the kidney tissues were observed after the treatment. Oleanolic acid led to decreased protein expressions of TGF-β, TGF-β receptor I, and TGF-β receptor II, as well as the phosphorylation of Smad2. Our current study suggested that oleanolic acid could be a complementary and alternative therapy for renal fibrosis potentially by targeting the TGF-β/Smad pathway.

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Journal articles on the topic 'Oleanic acid'

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