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ursolic acid

Helen L Alvarado, Ana C Calpena, Maria L Garduno-Ramirez, Raul Ortiz, Consolacion Melguizo, Jose M Prados, Beatriz Clares
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. METHOD: The nanoemulsion was characterized by dynamic light scattering, transmission electron microscopy...
January 11, 2018: Anti-cancer Agents in Medicinal Chemistry
Jing Miao, Xia Li, Chengcheng Zhao, Xiaoxiao Gao, Ying Wang, Wenyuan Gao
Chaenomeles is an important source for food industry in China, and its planting area is expanding year by year. This study was conducted to evaluate different varieties of Chaenomeles by comparing the chemical compositions, antioxidant activity and α-glucosidase inhibitory activity of peels and fleshes from twelve varieties of Chaenomeles. In the results, peels of Chaenomeles contain more phenolics, flavonoids and triterpenes, and show better antioxidant activity and α-glucosidase inhibitory activity than their fleshes...
May 15, 2018: Food Chemistry
Simone Tasca Cargnin, Andressa Finkler Staudt, Patrícia Medeiros, Daniel de Medeiros Sol Sol, Ana Paula de Azevedo Dos Santos, Fernando Berton Zanchi, Grace Gosmann, Antonio Puyet, Carolina Bioni Garcia Teles, Simone Baggio Gnoatto
In this report, we describe the semisynthesis of two series of ursolic and betulinic acid derivatives through designed by modifications at the C-3 and C-28 positions and demonstrate their antimalarial activity against chloroquine-resistant P. falciparum (W2 strain). Structural modifications at C-3 were more advantageous to antimalarial activity than simultaneous modifications at C-3 and C-28 positions. The ester derivative, 3β-butanoyl betulinic acid (7b), was the most active compound (IC50 = 3.4 µM) and it did not exhibit cytotoxicity against VERO nor HepG2 cells (CC50 > 400 µM), showing selectivity towards parasites (selectivity index > 117...
December 29, 2017: Bioorganic & Medicinal Chemistry Letters
Vladimir Morocho, Andrea Valle, Jessica García, Gianluca Gilardoni, Luis Cartuche, Alírica I Suárez
The phytochemical investigation of both volatile and fixed metabolites of Clinopodium taxifolium (Kunth) Govaerts (Lamiaceae) was performed for the first time. It allowed the isolation and characterization of the essential oil and six known compounds: carvacrol (1), squalane (2), uvaol (3), erythrodiol (4), ursolic acid (5), and salvigenin (6). Their structures were identified and characterized by Nuclear Magnetic Resonance (NMR) and Gas Chromatography coupled to Mass Spectroscopy (GC-MS), and corroborated by literature...
January 11, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Yu Tian, Zhonghao Sun, Wenqian Wang, Hai Shang, Baoqi Wang, Di Deng, Guoxu Ma, Haifeng Wu, Nailiang Zhu, Xudong Xu, Guibo Sun, Xiaobo Sun
A series of novel oleanolic acid 3-O-β-d-glucuronopyranoside derivatives have been designed and synthesized. Biological evaluation has indicated that some of the synthesized compounds exhibit moderate to good activity against H₂O₂-induced injury in rat myocardial cells (H9c2). Particularly, derivative 28-N-isobutyl ursolic amide 3-O-β-d-galactopyranoside (8a) exhibited a greater protective effect than the positive control oleanolic acid 3-O-β-d-glucuronopyranoside, indicating that it possesses a great potential for further development as a cardiovascular disease modulator by structural modification...
January 10, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Jean J K Bankeu, Stéphanie Madjouka, Guy R T Feuya, Yannick S F Fongang, Sadaf Siddiqui, Iftikhar Ali, Lateef Mehreen, Bruno N Lenta, Sammer Yousuf, Didérot T Noungoué, Augustin S Ngouela, Muhammad S Ali
Phytochemical investigation of dichloromethane neutral phase of stem bark of Nauclea pobeguinii led to the isolation of a new monoterpene indole alkaloid, pobeguinine 1 along with 14 known compounds including (-)-naucleofficine D (2a), (+)-naucleofficine D (2b), naucleidinal (3), quafrinoic acid (4), betulinic acid (5), ursolic acid (6), quinovic acid (7), quinovic acid 3-O-α-L-rhamnopyranoside (8a), quinovic acid 3-O-β-D-fucopyranoside (8b), β-sitosterol (9), β-sitosterol 3-O-β-D-glucopyranoside (10), benzoic acid (11), lacceroic acid (12) and n-heptacosane (13)...
January 10, 2018: Zeitschrift Für Naturforschung. C, A Journal of Biosciences
Tingjun Ren, Zhongqi Xu
In this study, a capillary zone electrophoresis (CZE) method was first developed to identify three microconstituents of isomeric pentacyclic triterpene acids (PTAs including oleanolic acid (OA), ursolic acid (UA) and betulinic acid (BA)) in Forsythiae Fructus (FF). The baseline separation of PTAs by CZE were eventually achieved in a background electrolyte (BGE) containing 50.0 mmol/L borax and 0.5 mmol/L β-cyclodextrin (β-CD) at pH 9.5 within 13.0 min. Herein, it was not only the compositions of BGE were detail investigated for rapid and good separation, but also the binding ratio and the equilibrium constants (K) for OA, UA and BA with β-CD was estimated by double reciprocal equation to well understand the separation mechanism...
January 5, 2018: Electrophoresis
Haibo Wu, Tingting Liu, Yuxuan Lian, Wenshu Wang
Two new eremophilenolides, ligushicins A (1) and B (2), and two known compounds including β-sitosterol and ursolic acid were isolated from Ligulariopsis shichuana. The structures of new compounds were established on the basis of 1D and 2D NMR data and HRESIMS data interpretation. The absolute configuration of new compounds was assigned by ECD spectroscopy, and that of ligushicins A (1) was confirmed by X-ray diffraction analysis. The antifungal and antifeedant activities of new compounds were evaluated against four plant pathogenic fungi and third-instar larvae of Plutella xylostella, respectively...
December 27, 2017: Natural Product Research
Lucy Catteau, Nathalie T Reichmann, Joshua Olson, Mariana G Pinho, Victor Nizet, Françoise Van Bambeke, Joëlle Quetin-Leclercq
Combining antibiotics with resistance reversing agents is a key strategy to overcome bacterial resistance. Upon screening antimicrobial activities of plants used in traditional medicine, we found that a leaf dichloromethane extract from the shea butter tree (Vitellaria paradoxa) had antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) with further evidence of synergy when combined with β-lactams. Using HPLC-MS, we identified ursolic (UA) and oleanolic acids (OA) in leaves and twigs of this species, and quantified them by HPLC-UV as the major constituents in leaf extracts (21% and 6% respectively)...
December 16, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Belma Hasdemir, Ozlem Sacan, Hasniye Yasa, Hatice B Kucuk, Ayse S Yusufoglu, Refiye Yanardag
Fifteen novel aryl, substituted aryl and heteroaryl γ-hydroxy- (2a-e), γ-methoxyimino- (3a-e), and γ-benzyloxyimino- (4a-e) butyric acid methyl esters were investigated for their enzyme inhibition, and the synthesis of 10 compounds (3a-e, 4a-e) is given in this study. The other five compounds (2a-e) were synthesized before in another study. Compounds 3a-e and 4a-e were synthesized in this work as original compounds and characterized by 1 H and 13 C NMR, IR, mass, and elemental analyses. Their (E/Z)-isomerisation ratios were analyzed by 1 H and 13 C NMR...
December 18, 2017: Archiv der Pharmazie
Chao Wen, Dongshan Wang, Xing Li, Tao Huang, Cheng Huang, Kaifeng Hu
The anti-hyperlipidemic effects of crude crabapple extracts derived from Malus 'Red jade', Malus hupehensis (Pamp.) Rehd. and Malus prunifolia (Willd.) Borkh. were evaluated on high-fat diet induced obese (HF DIO) mice. The results revealed that some of these extracts could lower serum cholesterol levels in HF DIO mice. The same extracts were also parallelly analyzed by LC-MS in both positive and negative ionization modes. Based on the pharmacological results, 22 LC-MS variables were identified to be correlated with the anti-hyperlipidemic effects using partial least square discriminant analysis (PLS-DA) and independent samples t-test...
December 2, 2017: Journal of Pharmaceutical and Biomedical Analysis
Lan Li, Yu Hou, Jing Yu, Yulin Lu, Li Chang, Meiping Jiang, Xingrao Wu
Objective: This study was designed to investigate the effect of combination of ursolic acid (UA) with cisplatin (DDP) on cervical cancer cell proliferation and apoptosis. Methods: The mRNA and protein expressions of nuclear factor-kappa B (NF-κB) p65 in cervical cancer cells were examined using RT-PCR and western blot. MTT and colony formation assays were performed to examine the DDP toxicity and the proliferation ability of cervical cancer cells. Cell morphology was observed by means of Hoechst33258 and transmission electron microscopy (TEM)...
November 14, 2017: Oncotarget
Guirong Zheng, Zhichun Shen, Aixiao Xu, Kai Jiang, Pengyu Wu, Xiang Yang, Xian Chen, Jingwei Shao
The anticancer properties of ursolic acid (UA) and metformin (Met) have been well demonstrated. However, whether these compounds can act synergistically to prevent and treat cancer is not known. We present in this study, the synergism between UA and Met, and that of a new codrug made of UA and Met (UA-Met) against several cancer cell lines. The combination of high concentration of UA (25, 50, 75, 100 μM) and Met (5, 10, 20, 40 mM) resulted in synergetic cytotoxicity on MDA-MB-231 and MCF-7 cells (CI < 0...
December 11, 2017: Journal of Agricultural and Food Chemistry
Xiaoyan Liao, Fangli Hu, Zilin Chen
Ripe O. fragrans fruit is composed of purple peels, green pulps and light brown seeds. Since the biological effects such as antioxidative activities and platelet-aggregation inhibition are related to the phenolic compounds and flavonoids in O. fragrans fruits, these components have a great potential as functional food ingredient. In the work, active components in O. fragrans fruits extraction were investigated by HPLC-ESI-MS/MS. A total of twenty-eight compounds were identified and sixteen components were first discovered in O...
December 9, 2017: Journal of Agricultural and Food Chemistry
Roseane Leandra da Rosa, Luciane Ângela Nottar Nesello, Luisa Nathalia Bolda Mariano, Lincon Bordignon Somensi, Adriana Campos, Ana Myrelle Pinheiro, Sabrina Costa, Marjana Rial, Mariana Tozzo, Valdir Cechinel-Filho, Sérgio Faloni de Andrade, Luísa Mota Da Silva
According to the Brazilian folk medicine, the leaves of Plinia edulis (Vell.) Sobral (Myrtaceae), known as cambuca, are indicated in the treatment of gastric disorders. Infusions of P. edulis leaves were previously demonstrated to contain both maslinic (MA) and ursolic acids (UA). Both triterpenes have also been identified in the methanolic extract of peels from P. edulis fruit (MEPPE); however, the antiulcer effects of MEPPE have not yet been studied. This study therefore evaluates the gastroprotective potential of MEPPE, MA, and UA using ethanol/HCl- and indomethacin-induced gastric ulcers in mice...
December 5, 2017: Naunyn-Schmiedeberg's Archives of Pharmacology
Lina María Preciado, Paola Rey-Suárez, Isabel Cristina Henao, Jaime Andrés Pereañez
Betulinic acid (BA), Oleanolic acid (OA) and Ursolic acid (UA), are pentacyclic triterpenoids with widespread occurrence throughout the plant kingdom, these compounds are widely recognized by their pharmacological and biological properties, such as, anti-tumoral, anti-inflammatory, anti-microbial and hepatoprotective activity. In this work we determined the inhibitory ability of these compounds on the enzymatic, hemorrhagic, myotoxic and edema-inducing activities of Batx-I, a P-I metalloproteinase isolated from Bothrops atrox venom...
December 1, 2017: Chemico-biological Interactions
Alessia Lodi, Achinto Saha, Xiyuan Lu, Bo Wang, Enrique Sentandreu, Meghan Collins, Mikhail G Kolonin, John DiGiovanni, Stefano Tiziani
High-throughput screening of a natural compound library was performed to identify the most efficacious combinatorial treatment on prostate cancer. Ursolic acid, curcumin and resveratrol were selected for further analyses and administered in vivo via the diet, either alone or in combination, in a mouse allograft model of prostate cancer. All possible combinations of these natural compounds produced synergistic effects on tumor size and weight, as predicted in the screens. A subsequent untargeted metabolomics and metabolic flux analysis using isotopically labeled glutamine indicated that the compound combinations modulated glutamine metabolism...
2017: NPJ Precision Oncology
Hyun Seok Bang, Dae Yun Seo, Young Min Chung, Do Hyung Kim, Sam-Jun Lee, Sung Ryul Lee, Hyo-Bum Kwak, Tae Nyun Kim, Min Kim, Kyoung-Mo Oh, Young Jin Son, Sanghyun Kim, Jin Han
Ursolic acid (UA) supplementation was previously shown to improve skeletal muscle function in resistance-trained men. This study aimed to determine, using the same experimental paradigm, whether UA also has beneficial effects on exercise-induced skeletal muscle damage markers including the levels of cortisol, B-type natriuretic peptide (BNP), myoglobin, creatine kinase (CK), creatine kinase-myocardial band (CK-MB), and lactate dehydrogenase (LDH) in resistance-trained men. Sixteen healthy participants were randomly assigned to resistance training (RT) or RT+UA groups (n=8 per group)...
November 2017: Korean Journal of Physiology & Pharmacology
Robson Xavier Faria, Leandro Machado Rocha, Eloísa Portugal Barros Silva Soares Souza, Fernanda Borges Almeida, Caio Pinho Fernandes, José Augusto Albuquerque Santos
Schistosomiasis is promoted for species from Schistosoma genus affecting over 200 million people worldwide. Molluscicides are an efficient method to control this disease, being able to reduce intermediate host snail Biomphalaria glabrata number. In function of resistance cases using niclosamide, natural products are promisors to discover new drugs. Manilkara subsericea is endemic to Brazilian sandbanks of Rio de Janeiro State and wide ranges of biological activities. However, there is no studies evaluating its effects as molluscicidal agent...
November 30, 2017: Acta Tropica
Chao-Min Wang, Kuei-Lin Yeh, Shang-Jie Tsai, Yun-Lian Jhan, Chang-Hung Chou
(1) Background: In China and South Asia, Alstonia scholaris (Apocynaceae) is an important medicinal plant that has been historically used in traditional ethnopharmacy to treat infectious diseases. Although various pharmacological activities have been reported, the anti-lung cancer components of A. scholaris have not yet been identified. The objective of this study is to evaluate the active components of the leaf extract of A. scholaris, and assess the anti-proliferation effects of isolated compounds against non-small-cell lung carcinoma cells; (2) Methods: NMR was used to identify the chemical constitutes isolated from the leaf extract of A...
December 1, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
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