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A review of structural modification and biological activities of oleanolic acid

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Chinese Journal of Natural Medicines 2024年第1期22卷 15-30页

作者： YANG Huali DENG Minghui JIA Hongwei ZHANG Kaicheng LIU Yang CHENG Maosheng XIAO Wei State Key Laboratory of New-tech for Chinese Medicine Pharmaceutical Process Jiangsu Kanion Pharmaceutical Co.Ltd.Lianyungang 222001China Key Laboratory of Structure-Based Drug Design&Discovery of Ministry of Education School of Pharmaceutical EngineeringShenyang Pharmaceutical UniversityShenyang 110016China

oleanolic acid(OA),a pentacyclic triterpenoid,exhibits a broad spectrum of biological activities,including antitumor,antiviral,antibacterial,anti-inflammatory,hepatoprotective,hypoglycemic,and hypolipidemic *** its initial isolation and identification,numerous studies have reported on the structural modifications and pharmacological activities of OA and its *** this,there has been a dearth of comprehensive reviews in the past two decades,leading to challenges in subsequent research on *** on the main biological activities of OA,this paper comprehensively summarized the modification strategies and structureactivity relationships(SARs)of OA and its derivatives to provide valuable reference for future investigations into OA.

关键词： oleanolic acid Derivatives Pentacyclic triterpenoid Structural modification Biological activities

The natural sources,extraction,and nephroprotective function of oleanolic acid and ursolic acid:a review

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Food and Health 2024年第3期6卷 20-32页

作者： Wen-Ying Chen Hong-Wei Wang Song Yao Yao Zhou Shuang-Chao Liu Xiao Li Shen School of Public Health Zunyi Medical UniversityZunyi 563000GuizhouChina Key Laboratory of Maternal&Child Health and Exposure Science of Guizhou Higher Education Institutes Zunyi 563000GuizhouChina

oleanolic acid(OA)and ursolic acid(UA)are commonly present in the cuticular wax of many edible fruits and medicinal *** and UA belong to the group of bioactive pentacyclic triterpenoids,exhibiting a wide range of beneficial effects including protection for the kidneys,liver,heart,gastrointestinal tract,and spinal ***,OA and UA exhibit antioxidant,anti-ferroptotic,anti-apoptotic,anti-inflammatory,anti-tumor,anti-viral,anti-diabetic,anti-microbial,anti-parasitic,analgesic,wound-healing,hypolipidemic,and hypoglycemic properties,often without notable side *** to the extensive array of their positive functions,it is not feasible to thoroughly cover all aspects in this ***,the primary focus lies on reviewing the natural sources,extraction,and nephroprotective properties of OA and *** summarize,current literatures highlight the nephroprotective mechanisms of OA and UA,primarily involving inhibiting oxidative stress,endoplasmic reticulum stress,glycative stress,dyslipidemia,inflammation,apoptosis,pyroptosis,and renal fibrosis,promoting diuresis,as well as fine-tuning autophagy.

关键词： oleanolic acid ursolic acid natural sources nephroprotective nephrotoxicity

Design and semisynthesis of oleanolic acid derivatives as VEGF inhibitors:Inhibition of VEGF-induced proliferation,angiogenesis,and VEGFR2 activation in HUVECs

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Chinese Journal of Natural Medicines 2022年第3期20卷 229-240页

作者： MENG Ning XIE Hong-Xu HOU Jia-Rong CHEN Yan-Bin WU Meng-Jun GUO Yue-Wei JIANG Cheng-Shi School of Biological Science and Technology University of JinanJinan 250022China State Key Laboratory ofDrug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China

Angiogenesis inhibitors targeting the VEGF signaling pathway are developed into drugs for the treatment of vaious diseases,such as cancer,rheumatoid arthritis,and age-related macular *** studies have revealed that oleanolic acid(OA),a natural pentacyclic triterpenoid,inhibited the VEGF/VEGFR2 signaling pathway and angiogenesis in HUVECs,which may represent an attractive VEGF *** this paper,rational structural modification towards OA was performed in order to improve its inhibitory effects aganist VEGF and anti-angiogenesis *** a result,a series of novel OA derivatives,possessingα,β-unsat-urated ketone system in ring A and amide functional group at C-28,were prepared and evaluated for cytotoxicity and their ability to inhibit VEGF-induced abnormal proliferation of *** results showed that two promising derivatives,OA-1 and OA-16,exhibited no in vitro cytotoxicity against HUVECs but showed more potent inhibitory activity against VEGF-induced proliferation and angiogenesis in HUVECs,compared with *** results of Western blot indicated that OA-1 and OA-16 inhibited VEGF-induced VE-GFR2 ***,small interfering RNA experiments were performed to confirm that both compounds inhibited VEGF-induced angiogenesis via ***,the present study resulted in the discovery of new promising OA-inspired VEGF inhibitors,which can serve as potential lead compounds for the treatment of angiogenesis-related diseases.

关键词： oleanolic acid Structural modification VEGF inhibitor VEGFR2 Angiogenesis

oleanolic acid attenuates liver ischemia reper-fusion injury by HO-1/Sesn2 signaling pathway

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Hepatobiliary & Pancreatic Diseases International 2016年第5期15卷 519-524页

作者： Bao-Bin Hao Xiong-Xiong Pan Ye Fan Ling Lu Xiao-Feng Qian Xue-Hao Wang Feng Zhang Jian-Hua Rao Department of Liver Surgery First Affiliated Hospital of Nanjing Medical UniversityKey Laboratory of Living Donor Liver Transplantation of Ministry of Public HealthNanjing 210029China

BACKGROUND: Ischemia reperfusion injury (IRI) is unavoid-able in liver transplantation and hepatectomy. The present study aimed to explore the possible mechanism and the effect of oleanolic acid (OA) in hepatic IRI. METHODS: Mice were randomly divided into 6 groups based on different treatment. IRI model: The hepatic artery, portal vein, and bile duct to the left and median liver lobes (70% of the liver) were occluded with an atraumatic bulldog clamp for 90 minutes and then the clamp was removed for reperfusion. The mice were sacriifced 6 hours after reperfusion, and blood and liver tissues were collected. Liver injury was evaluated by biochemical and histopathologic examinations. The expressions of Sesn2, PI3K, Akt and heme oxygenase-1 (HO-1) were mea-sured with quantitative real-time RT-PCR and Western blotting. RESULTS: The serum aminotransferases level and scores of he-patic histology were increased after reperfusion. The increase was attenuated by pretreatment with OA (P CONCLUSIONS: Our results demonstrate that OA can attenu-ate hepatic IRI. The protective mechanism may be related to the OA-induced HO-1/Sesn2 signaling pathway.

关键词： oleanolic acid liver injury ischemia reperfusion HO-1 Sesn2

oleanolic acid:a promising neuroprotective agent for cerebral ischemia

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Neural Regeneration Research 2015年第4期10卷 540-541页

作者： Caltana Laura Nieto María Luisa Brusco Alicia Instituto de Biología Celulary Neurociencia IBCN(UBA-CONICET)Buenos AiresArgentina Instituto Biologíay Genética Molecular CSIC-UVAValladolidSpain

Stroke is considered the most common and severely disabling neurological disease. It is one of the leading causes of death after heart disease and cancer, causing 10% deaths worldwide and involving risk factors such as smoking, obesity and nutritional disbalance. Disability affects 75% of stroke survivors through severe mental and/or physical impairment depending on the affected brain area （Go et al., 2014）.

关键词： acid oleanolic acid

A Self-assembled Nanoparticle Platform Based on Amphiphilic oleanolic acid Polyprodrug for Cancer Therapy

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Chinese Journal of Polymer Science 2020年第8期38卷 819-829,I0006页

作者： Ying-Sa Wang Gui-Liang Li Shang-Bin Zhu Fan-Chen Jing Run-Dong Liu Sai-Sai Li Jing He Jian-Du Lei Beijing Key Laboratory of Lignocellulosic Chemistry Engineering Research Center of Forestry Biomass Materials and Bioenergy(Ministry of Education)Beijing Forestry UniversityBeijing 100083China

oleanolic acid(OA)is a pentacyclic triterpenoid compound with extensive biological effects,such as anti-inflammatory and anticancer ***,the application of OA in chemotherapy is hampered by its poor solubility and severe adverse *** solve the problems,we developed a self-assembled nanoparticle platform based on amphiphilic oleanolic acid polyprodrug,poly[oligo(ethylene glycol)methyl ether methacrylate]-b-poly(oleanolic acid methacrylate)(POEGMA-b-POAMA),encapsulating 10-hydroxycamptothecin(HCPT)to achieve efficient cancer *** polyprodrug was prepared via reversible addition-fragmentation chain transfer polymerization(RAFT),and could selfassemble to prepare POEGMA-b-POAMA/HCPT nanoparticles(NPs).The obtained nanoparticles exhibited appropriate particle size,excellent drug stability,good drug loading capacity,and high drug loading *** vitro drug release indicated that the drug release was prolonged to 132 *** POEGMA-b-POAMA/HCPT NPs enhanced cell cytotoxicity in 4T1 cells and MCF-7 cells and could be efficiently uptaken by 4T1 ***,in vivo antitumor efficiency showed that the POEGMA-b-POAMA/HCPT NPs had great antitumor efficiency with considerably low adverse effects in the treatment of the 4T1 mouse breast tumor xenograft ***,POEGMA-b-POAMA/HCPT NPs provide great potential as a platform for drug delivery applications.

关键词： Self-assemble Nanoparticle oleanolic acid Amphiphilic polyprodrug Drug delivery

Synthesis of Two Natural oleanolic acid Saponins

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Chinese Journal of Chemistry 2006年第4期24卷 509-517页

作者：李春霞臧静王鹏张秀丽管华诗李英霞 Key Laboratory of Marine Drugs of the Ministry of Education of China Institute of Marine Drug and Food Ocean University of China Qingdao Shandong 266003 China

3-O-[β-D-Glucopyranosyl-（1→3）-α-L-arabinopyranosyl]-oleanolic acid-28-O-[β-D-glucopyranosyl] ester 1 was synthesized concisely by a convergent strategy. Using stepwise fashion for the synthesis of saponin 2, 3-O-{[β-D-glucopyranosyl-（1→2）]-[α-L-arabinopyranosyl-（1→3）]-α-L-arabinopyranosyl）-oleanolic acid-28-O-（β- D-glucopyranosyl） ester, an abnormal phenomenon, that the terminal arabinosyl residue took the ^1C4 conformation instead of typical ^4C1 form, was observed. Deprotection or heating could not resume the normal conformation, which resulted in the product of 2＇ not 2.

关键词： oleanolic acid saponin glycosylation conformation synthesis

Efficacy of quercetin, oleanolic acid, icariin on apoptosis and mitogen-activated protein kinases signaling pathways in hippocampal neurons of Sprague-Dawley rats cultured with high glucose medium

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Journal of Traditional Chinese Medicine 2021年第5期41卷 732-738页

作者： YAN Bin WANG Jingbo TIAN Guoqing Department of Traditional Chinese Medicine Peking Union Medical College HospitalChinese Academy of Medical SciencesBeijing 100730China

OBJECTIVE:To investigate the effect of quercetin,oleanolic acid,icariin and their compatibility on the apoptosisofhippocampalneuronsof Sprague-Dawley(SD)rats cultured with high glucose medium and the possible ***:The extracts were purchased from China Food and Drug Control Institute and *** was obtained from newborn 24 h SD *** culturing the hippocampus in different medium for 72 h,flow cytometry was used to detect the apoptosis of hippocampal neurons,and Western blot was utilized to test the expressions of p-p38,p38,p-c-Jun N-terminal kinase(JNK)and ***:Compared with the control group(CG),the neuronal apoptosis rate and the ratios of p-p38/p38 and p-JNK/JNK were significantly increased in the high glucose group(GG)(Poleanolic acid and icariin can alleviate the apoptosis of hippocampus neurons,reduce the phosphorylation of p38 and JNK in p38 mitogen-activated protein kinases and JNK signaling *** the efficacy of the three drugs in combination with each other can be strengthened.

关键词： glucose hippocampus quercetin oleanolic acid icariin mitogen-activated protein kinases

oleanolic acid isolated from ethanolic extract of Phytolacca decandra induces apoptosis in A375 skin melanoma cells: drug-DNA interaction and signaling cascade

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Journal of Integrative Medicine 2014年第2期12卷 102-114页

作者： Samrat Ghosh Kausik Bishayee Anisur Rahman Khuda-Bukhsh Cytogenetics and Molecular Biology Laboratory Department of ZoologyUniversity of Kalyani

OBJECTIVE： oleanolic acid （OA） has been reported to have anticancer effects, but the extent of its cytotoxicity, its ability to interact with nuclear DNA, its action against skin melanoma, as well as the molecular mechanism of its action against cell proliferation and in support of cell death are still unexplored. This led us to examine the efficacy of OA, a bioactive compound isolated from Phytolacca decandra, on these issues in the present investigation. METHODS： Studies related to analyses of cell viability, drug-DNA interaction, cell proliferation, cell cycle and epidermal growth factor receptor （EGFR） activity were performed. To investigate whether cells undergo apoptosis, studies like fluorescence microscopy, poly （ADP-ribose） polymerase （PARP） degradation, annexin V-fluorescein isothiocyanate/propidium iodide assay, alteration in mitochondrial membrane potential and activity of some relevant signaling proteins were performed. RESULTS： OA displayed a minimal and negligible cytotoxic effect on normal HaCaT cells （skin keratinocytes） and peripheral blood mononuclear cells but by contrast it reduced A375 cell viability significantly. OA interacted with nuclear DNA quickly after exposure. It acted as an anti- proliferative agent. It suppressed EGFR activity. OA administration led the cells to mitochondria- dependent caspase 3-mediated apoptosis. CONCLUSION： OA interacts with cellular DNA, inhibits proliferation possibly through modulating EGFR activity and induces mitochondria-dependent caspase 3-mediated apoptosis in A375 cells which would qualify it as a potent anticancer agent.

关键词： oleanolic acid skin melanoma drug-DNA interaction proliferation epidermal growth factor receptor apoptosis