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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

ursolic acid inhibits proliferation and induces apoptosis of HT-29 colon cancer cells by inhibiting the EGFR/MAPK pathway

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Journal of Zhejiang University-Science B(Biomedicine & Biotechnology) 2009年第9期10卷 668-674页

作者： Jian-zhen SHAN Yan-yan XUAN Shu ZHENG Qi DONG Su-zhan ZHANG Department of Traditional Chinese Medicine the Second Affiliated Hospital School of Medicine Zhejiang University Hangzhou 310009 China Cancer Institute School of Medicine Zhejiang University Hangzhou 310009 China

Objective： To investigate the effects ofursolic acid on the proliferation and apoptosis of human HT-29 colon cancer cells. Methods： 3-（4,5-dimethylthiazol-2-yl）-2,5-diphenyltetrazolium bromide （MTT） and flow cytometry assays were performed to evaluate the effects of ursolic acid on the growth and apoptosis of HT-29 cells. Western blot analysis was applied to investigate the inhibitory efibcts of ursolic acid on the phosphorylation of the epidermal growth factor receptor （EGFR）, extracellular signal-regulated kinase （ERK）, c-Jun N-terminal kinase （JNK）, and p38 mitogen-activated protein kinase （p38 MAPK）, and the activity of B cell leukemia-2 （Bcl-2）, B cell leukemia-xL （Bcl-xL）, caspase-3, and caspase-9. Results： ursolic acid inhibited the growth of HT-29 cells in dose- and time-dependent manners. The median inhibition concentration （IC50） values for 24, 48, and 72 h treatment were 26, 20, and 18 pmol/L, respectively. The apoptotic rates of 10, 20, and 40 μmol/L ursolic acid treatments for 24 h were 5.74%, 14.49%, and 33.05%, and for 48 h were 9%, 21.39%, and 40.49%, respectively. ursolic acid suppressed the phosphorylation of EGFR, ERK1/2, p38 MAPK, and JNK, which is well correlated with its growth inhibitory effect. 10, 20, and 40 μmol/L ursolic acid significantly inhibited the proliferation of EGF-stimulated HT-29 cells （P〈0.05）. Cell proliferation was most significantly inhibited when treated with 10 and 20 μmol/L ursolic acid combined with 200 nmol/L AG 1478 or 10 μmol/L U0126 （P〈0.01）. Besides, it also down-regulated the expression of Bcl-2 and Bcl-xL and activated caspase-3 and caspase-9. Conclusion： ursolic acid induces apoptosis in HT-29 cells by suppressing the EGFR/MAPK pathway, suggesting that it may be a potent agent for the treatment of colorectal cancer.

关键词： Colon cancer ursolic acid Epidermal growth factor receptor (EGFR) Mitogen-activated protein kinase (MAPK) Apoptosis

ursolic acid induces neural regeneration after sciatic nerve injury

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Neural Regeneration Research 2013年第27期8卷 2510-2519页

作者： Biao Liu Yan Liu Guang Yang Zemin Xu Jiajun Chen Department of Hand Surgery China-Japan Union Hospital of Jilin University Department of Neurology China-Japan Union Hospital of Jilin University

In this study, we aimed to explore the role of ursolic acid in the neural regeneration of the injured sciatic nerve. BALB/c mice were used to establish models of sciatic nerve injury through unilateral sciatic nerve complete transection and microscopic anastomosis at 0.5 cm below the ischial tuber-osity. The successful y generated model mice were treated with 10, 5, or 2.5 mg/kg ursolic acid via intraperitoneal injection. Enzyme-linked immunosorbent assay results showed that serum S100 protein expression level gradual y increased at 1-4 weeks after sciatic nerve injury, and significantly decreased at 8 weeks. As such, ursolic acid has the capacity to significantly increase S100 protein expression levels. Real-time quantitative PCR showed that S100 mRNA expression in the L 4-6 segments on the injury side was increased after ursolic acid treatment. In addition, the muscular mass index in the soleus muscle was also increased in mice treated with ursolic acid. Toluidine blue staining revealed that the quantity and average diameter of myelinated nerve fibers in the injured sciatic nerve were significantly increased after treatment with ursolic acid. 10 and 5 mg/kg of ursolic acid produced stronger effects than 2.5 mg/kg of ursolic acid. Our findings indicate that ursolic acid can dose-dependently increase S100 expression and promote neural regeneration in BALB/c mice fol owing sciatic nerve injury.

关键词： neural regeneration traditional Chinese medicine ursolic acid triterpenoid sciatic nerve peripheralnerve injury S100 muscular atrophy nerve myelin sheath grants-supported paper neuroregeneration

ursolic acid induces human hepatoma cell line SMMC-7721 apoptosis via p53-dependent pathway

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Chinese Medical Journal 2010年第14期123卷 1915-1923页

作者： YU Yan-xia GU Zhen-lun YIN Jiang-lin CHOU Wen-hsien KWOK Chi-yi QIN Zheng-hong LIANG Zhong-qin Soochow Institute of Chinese Materia Medica Suzhou Suzhou Jiangsu 215007 China Department of Pharmacy Nanjing Medical University Affiliated Suzhou Hospital Suzhou Jiangsu 215002 China Department of Pharmacology Soochow University School of Medicine Suzhou Jiangsu 215123 China

Background ursolic acid （UA） is a ubiquitous molecule in the plant kingdom with specific anticancer effects that have been shown in vitro and in vivo. Although UA can inhibit the proliferation of liver cancer cells and induce apoptosis of many types of tumor cells, the molecular mechanism of its anti-hepatoma activity is still not well defined. The objective of this study was to investigate the inhibitory effect and mechanisms of UA on the human hepatoma cell line SMMC-7721. Methods After treatment with UA, the growth inhibition of SMMC-7721 cells was assessed by MTT assay. Cells were also evaluated by flow cytometric analysis, Wright-Giemasa staining, Hoechst 33258 staining and transmission electron microscope after they were induced by UA. DNA microarray technology was used to investigate the gene expression pattern of SMMC-7721 cells exposed to UA 40 pmol/L. The molecular mechanism of cells death was analyzed by real-time RT-PCR and Western blotting. Results The proliferation of SMMC-7721 cells was significantly inhibited in a dose- and time-dependent manner after UA treatment. UA induced cell cycle arrest and apoptosis. The DNA microarray analysis indicated that 64 genes were found to be markedly up- or down-expressed, including GDF15, SOD2, ATF3, and fos. The result of Western blotting showed the apoptotic proteins p53 and Bax were up-regulated while the anti-apoptotic protein Bcl-2 was down-regulated. Real-time RT-PCR confirmed UA could up-regulate the mRNA expressions of GDF15, SOD2, ATF3 and down-regulate the mRAN expression of fos. Meanwhile these effects were partly blocked by pretreatment with the p53 inhibitor Pft-a. Conclusion Activation of the p53 pathway is involved in UA inhibition of SMMC-7721 human hepatocellular carcinoma cell growth and induction of apoptosis.

关键词： ursolic acid SMMC-7721 cells p53

ursolic acid sensitized colon cancer cells to chemotherapy under hypoxia by inhibiting MDR1 through HIF-1α

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Journal of Zhejiang University-Science B(Biomedicine & Biotechnology) 2016年第9期17卷 672-682页

作者： Jian-zhen SHAN Yan-yan XUAN Qi ZHANG Jian-jin HUANG Department of Medical Oncology the Second Affiliated HospitalSchool of MedicineZhejiang University Cancer Institute of Zhejiang University Key Laboratory of Cancer Prevention and InterventionChina National Ministry of Education Department of General Surgery the Second Affiliated HospitalSchool of MedicineZhejiang University

Objective： To explore the efficacy of ursolic acid in sensitizing colon cancer cells to chemotherapy under hypoxia and its underlying mechanisms. Methods： Three colon cancer cell lines （RKO, LoVo, and SW480） were used as in vitro models. 5-Fluorouracil （5-FU） and oxaliplatin were used as chemotherapeutic drugs. Cell viability and apoptosis were tested to evaluate the sensitivity of colon cancer cells to chemotherapy. The transcription and ex- pression levels of hypoxia-inducible factor-1α （HIF-1α）, multidrug resistance gene 1 （MDR1）, and vascular endothelial growth factors （VEGF） were assessed by quantitative real-time polymerase chain reaction （qRT-PCR） and im- munoblotting. Cycloheximide and MG132 were used to inhibit protein synthesis and degradation, respectively. In vitro tube formation assay was used to evaluate angiogenesis. Results： We demonstrated the chemosensitizing effects of ursolic acid with 5-FU and oxaliplatin in three colon cancer cell lines under hypoxia. This effect was correlated to its inhibition of MDR1 through HIF-la. Moreover, ursolic acid was capable of inhibiting HIF-1α accumulation with little effects on its constitutional expression in normoxia. In addition, ursolic acid also down-regulated VEGF and inhibited tumor angiogenesis. Conclusions： ursolic acid exerted chemosensitizing effects in colon cancer cells under hypoxia by inhibiting HIF-la accumulation and the subsequent expression of the MDR1 and VEGF.

关键词： ursolic acid Colon cancer Hypoxia-inducible factor-1α (HIF-1α) Multidrug resistance gene 1 (MDR1) Drug resistance

ursolic acid synergistically enhances the therapeutic effects of oxaliplatin in colorectal cancer

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Protein & Cell 2016年第8期7卷 571-585页

作者： Jianzhen Shan Yanyan Xuan QiZhang Chunpeng Zhu Zhen Liu Suzhan Zhang Department of Medical Oncology The Second Affiliated Hospital Zhejiang University School of Medicine Hangzhou 310009 China Cancer Institute of Zhejiang University School of Medicine Hangzhou 310009 China Department of Hepatobiliary and Pancreatic Surgery The Second Affiliated Hospital Zhejiang University School of Medicine Hangzhou 310009 China Department of Gastroenterology The Second Affiliated Hospital Zhejiang University School of Medicine Hangzhou 310009 China

Oxaliplatin is a key drug in chemotherapy of colorectal cancer （CRC）. However, its efficacy is unsatisfied due to drug resistance of cancer ceils. In this study, we tested whether a natural agent, ursolic acid, was able to enhance the efficacy of oxaliplatin for CRC. Four CRC cell lines including SW480, SW620, LoVo, and RKO were used as in vitro models, and a SW620 xenograft mouse model was used in further in vivo study. We found that ursolic acid inhibited proliferation and induced apoptosis of all four cells and enhanced the cytotoxicity of oxaliplatin. This effect was associated with down-regulation of Bcl-xL, Bcl-2, survivin, activation of caspase-3, 8, 9, and inhibition of KRAS expression and BRAF, MEKll2, ERK1/2, p-38, JNK, AKT, IKKa, IKBa, and p65 phosphorylation of the MAPK, PI3K/AKT, and NF-KB signaling pathways. The two agents also showed synergistic effects against tumor growth in vivo. In addition, ursolic acid restored liver function and body weight of the mice treated with oxaliplatin. Thus, we concluded that ursolic acid could enhance the therapeutic effects of oxaliplatin against CRC both in vitro and in vivo, which offers an effective strategy to minimize the burden of oxaliplatin-induced adverse events and provides the groundwork for a new clinical strategy to treat CRC.

关键词： ursolic acid colorectal cancer oxaliplatin,signaling pathways

ursolic acid Inhibits T-Cell Activation through Modulating Nuclear Factor-κB Signaling

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Chinese Journal of Integrative Medicine 2012年第1期18卷 34-39页

作者：曾光陈疆梁清华游万辉吴汉军熊新贵 Institute of Integrative Medicine Xiangya HospitalCentral South University Telemedicine Centre Xiangya HospitalCentral South University

Objective： To investigate the effects of ursolic acid （UA） on T-cell proliferation and activation, as well as to examine its effect on nuclear factor- κ B （NF- κ B） signaling pathway in T cells. Methods： T-cells isolated from BALB/c mice were incubated with UA at concentrations ranging from 5-30μmol/L in the presence of phorbol 12-myristate 13-acetate （PMA） or PMA plus ionomycin. The proliferation of T cells was measured by the MIF assay. The expressions of CD69, CD25, and CD71 on T-cell surface were analyzed using flow cytometry. The level of interleukin-2 （IL-2） in the culture supernatant of activated T cells was quantified by enzyme-linked immunosorbent assay （ELISA）. The level of phosphorylated I κ B-α （p-I κ B-α ） in total protein and p65, a subunit of NF- κ B, nuclear translocation were measured by Western blot analysis. Results： UA in a dose-dependent manner significantly decreased the proliferation and inhibited the surface expressions of CD69, CD25, and CD71 in murine T lymphocytes upon in vitro activation （P〈0.01）. Significant reduction of IL-2 production was found in activated T cells treated with UA （P〈0.01）. The PMA-induced increase in p-I κ B-α protein was inhibited, and nuclear translocation of p65 from the cytoplasm was blocked by UA. Conclusion： UA is a potent inhibitor for T cell activation and proliferation; these effects are associated with the inhibition of NF- κ B signaling pathway.

关键词： ursolic acid T-cell activation CD69 CD25 CD71 nuclear factor- κ B

Discovery of novel ursolic acid derivatives as effective antimicrobial agents through a ROS-mediated apoptosis mechanism

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Frontiers of Chemical Science and Engineering 2023年第12期17卷 2101-2113页

作者： Yihong Yang Siyue Ma Ting Li Jingjing He Shitao Liu Hongwu Liu Jiaojiao Zhang Xiang Zhou Liwei Liu Song Yang National Key Laboratory of Green Pesticide Key Laboratory of Green Pesticide and Agricultural Bioengineering(Ministry of Education)Center for R&D of Fine Chemicals of Guizhou UniversityGuiyang 550025China

In response to the reduction of food production and economic losses caused by plant bacterial diseases, it is necessary to develop new, efficient, and green pesticides. Natural products are rich and sustainable source for the development of new pesticides due to their low toxicity, easy degradation, and eco-friendliness. In this study, we prepared three series of ursolic acid derivatives and assessed their antibacterial ability. Most target compounds exhibited outstanding antibacterial activities. Among them, the relative optimal EC50 values of Xanthomonas oryzae pv. oryzae and Xanthomonas axonopodis pv. citri were 2.23 (A17) and 1.39 (A16) μg·mL^(-1), respectively. The antimicrobial mechanism showed that compound A17 induced an excessive accumulation and production of reactive oxygen species in bacteria and damaged the cell membrane integrity to kill bacteria. More interestingly, the addition of low concentrations of exogenous hydrogen peroxide enhanced the antibacterial efficacy of compound A17 against Xanthomonas oryzae pv. oryzae. These entertaining results suggested that compound A17 induced an apparent apoptotic behavior in the tested bacteria. Overall, we developed the promising antimicrobial agents that destroyed the redox system of phytopathogenic bacteria, further demonstrating the unprecedented potential of ursolic acid for agricultural applications.

关键词： ursolic acid antibacterial activities reactive oxygen species apoptosis

Synthesis of an ursolic acid Saponin with N-Acetylglucosamine-containing Trisaccharide Residue

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Chinese Journal of Chemistry 2006年第10期24卷 1421-1426页

作者：王鹏李春霞王广法李英霞 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

The focus of this work is the synthesis of an ursolic acid saponin with an N-acetylglucosamine-containing trisaccharide residue. Therefore, ursolic acid 3-yl α-L-arabinopyranosyl-（1→2）-α-L-arabinopyranosyl-（1→6）-2- acetamido-2-deoxy-β-D-glucopyranoside （1） was concisely synthesized in convergent synthesis with 48.0% overall yield. The structure of saponin 1 was confirmed by ^1H NMR, ^13C NMR and mass spectra.

关键词： ursolic acid saponin N-acetylglucosamine glycosylation synthesis