齐墩果酸及其衍生物的研究进展
Advances in Studies on Oleanolic Acid and Derivatives
摘要: 齐墩果酸属于五环三萜类化合物，具有多种生物学活性。其药理作用不断被发现，且临床应用及结构改造逐渐深入，展现出广泛的应用前景。因此，现将齐墩果酸的药理作用及其结构修饰研究进展进行综述。
Abstract: Oleanolic acid belongs to pentacyclic triterpenes which has diverse biological activities. Its pharmacological effects continue to be found, and the studies of clinical application and structure modification are developed increasingly, showing a wide respect of applications. In this regard, gives a summary of the studies on pharmacological effects and structure modification of Oleanolic acid.
文章引用：孟艳秋, 赵娜, 聂慧慧, 邹超. 齐墩果酸及其衍生物的研究进展[J]. 世界肿瘤研究, 2012, 2(1): 1-8. http://dx.doi.org/10.12677/wjcr.2012.21001

参考文献

[1] Y. J. Chen, J. Liu, X. L.Yang, et al. Oleanolic acid nanosus pre- paration, in vitro characterization and enhanced hep-at protective effect. Journal of Pharmacy and Pharmacology, 2005, 57(2): 259- 264.
[2] H. G. Jeong. Inhibition of cytochrome P450 2E1 expression by Oleanolic acid: Hepatoprotective effects against carbon tetra- chloride-induced hepatic injury. Toxicology Letters, 1999, 105(3): 215-222.
[3] M. Yoshikawa and H. Matsuda. Antidiabetogenic activity of Oleanolic acid glycosides from medicinal foodstuffs. Biofactors, 2000, 13(1-4): 231-237.
[4] Z. Ovesna, A. Vachalkova, K. Horvathova, et a1. Pentacyclic triterpenoic acids: New chemoprotective compounds. Neoplasma, 2004, 51(5): 327-333.
[5] B. B. Aggarwal, Y. Takada, O. V. Oommen. From chemopreven- tion to chemotherapy: common targets and common goals. Expert Opinion on Investigational Drugs, 2004, 13(10): 1327-1338.
[6] F. A. Resende, C. A. M. de An-drade Barcala, M. C. da Silva Faria, et a1. Antimutagenicity of ursolicacid and Oleanolic acid against doxorubicin induced clastogenesis in Balb/c mice. Life Sciences, 2006, 79(13): 1268-1273.
[7] 杜瑜, 李焕德. 齐墩果酸的研究进展[J]. 中国药房, 2006, 17(4): 304-306.
[8] S. Marquina, N. Maldonado, M. L. Garduño-Ramírez, et al. Bio- active Oleanolic acid saponins and other constituents from the roots of Viguiera decurrens. Phytochemistry, 2001, 56(1): 93-97.
[9] Y. Kashiwada, H. K. Wang, T. Nagao, et al. Anti-AIDS agents 30 anti-HIV activity of Oleanolic acid, pomolic acid, and struc- turally related triterpenoids. Journal of Natural Products, 1998, 61(9): 1090-1095.
[10] C. M. Ma, N. Nakamura, M. Hattori, et al. Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia. Journal of Natural Products, 2000, 63(2): 238-242.
[11] 宫新江, 丁虹, 邱银生等. 齐墩果酸抗环磷酰胺所致大鼠肝细胞损伤作用[J]. 医药导报, 2006, 25(11): 1114-1116.
[12] 张杰, 许仄平, 孙宏斌等. 大鼠肝脏缺血–再灌注损伤时齐墩果酸对氧自由基的影响[J]. 临床麻醉学杂志, 2009, 25(5): 428-430.
[13] R. R. Ortiz-Andrade, S. García-Jiménez, P. Castillo-España, et al. α-Glucosidase inhibitory activity of the methanolic extract from Tournefortia hartwegiana: An anti-hyperglycemic agent. Journal of Ethnopharmcology, 2007, 109(1): 48-53.
[14] N. H. Buus, N. C. Hansson, R. Rodriguez-Rodriguez, et al. Antia- therogenic effects of Oleanolic acid in apolipoprotein E knockout mice. European Journal of Pharmacology, 2011, 670 (2-3): 519-526.
[15] 殷峻, 胡仁明, 陈名道等. 小檗碱、齐墩果酸和大蒜新素对糖代谢作用的体外研究[J]. 北京中医药大学学报, 2003, 26(2): 36-39.
[16] Z. Ovesna, A. Vachalkova, K. Horvatova, et a1. Pentacyclic triterpenoic acids: New chemoprotective compounds. Minireview Neoplasma, 2004, 51(5): 327-333.
[17] 黄炜, 黄济群, 张东方等. 甘草酸、18β-甘草次酸、熊果酸和齐墩果酸抗人癌细胞侵袭作用及其机理的研究. 中国中医药科技, 2003, 10(6): 349-350.
[18] 卫小红, 邵杰, 王军辉, A. Thaku. 齐墩果酸诱导人肺腺癌细胞A54凋亡及其与细胞内钙离子的关系[J]. 同济大学学报(医学版), 2009, 30(5): 19-23.
[19] 张红霞, 李鸿梅, 陈东等. 齐墩果酸诱导人白血病HL-60细胞凋亡及细胞周期阻滞[J]. 中国病理生理杂志, 2008, 24(10): 1909-1911.
[20] 黄炜, 吴其年, 黄敏珊等. 五环三萜类单体诱导人乳腺癌细胞凋亡的研究[J]. 中华中医药学刊, 2008, 26(7): 1566-1568.
[21] 吴勃岩, 高明, 徐绍娜. 女贞子有效成分齐墩果酸对S180荷瘤小鼠抑瘤作用及存活时间的影响[J]. 中医药信息, 2010, 21(1): 37-38.
[22] 李鸿梅, 李雪岩, 蔡德福等. 齐墩果酸对顺铂耐药胃癌SGC-7901细胞增殖的影响及其机制研究[J]. 中国药理学通报, 2009, 25(10): 1334-1337.
[23] Y. Fujiwara, Y. Komohara, R. Kudo, et al. Oleanolic acid inhibits macrophage differentiation into the M2 phenotype and glioblastoma cell proliferation by suppressing the activation of STAT3. Oncology Reports, 2011, 26(6): 1533-1537.
[24] R. Rodriguez-Rodriguez and M. D. Herrera. Pomace olive oil improves endothelial function in spontaneously hypertensive rats by increasing endothelial nitric oxide synthase expression. American Journal of Hypertension, 2007, 7(20): 728-734.
[25] S. S. Bachhav, S. D. Patil, M. S. Bhutada, et al. Oleanolic acid prevents glucocorticoid-induced hypertension in rats. Phyto- therapy Research, 2011, 25(10): 1435-1439.
[26] J. C. Steele, D. C. Warhurst, G. C. Kirby, et a1. In Vitro and in Vivo evaluation of betulinic acid as an ant malaria1. Phytothe- rapy Research, 1999, 13(2): 115-119.
[27] 范玉玲, 崔福德, 杨明世等. 齐墩果酸和齐酞酸钠对二甲苯引起的小鼠耳肿胀抑制作用的研究[J]. 中西医结合心脑血管病, 2002, 18(6): 37-38.
[28] E. M. Giner-larza, S. Manez, M. C. Recio, et al. Oleanonic acid, a 3-oxotriterpene trom Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity. European Journal of Pharma- cology, 2001, 428(1): 137-143.
[29] F. Mengoni, M. Lichtner and L. Battinelli. Anti-HIV activity of Oleanolic acid on infected human mononuclear cells. Planta Medica, 2002, 68(2): 111-114.
[30] Q. Bian, S. F. Liu, J. H. Huang, et al. Oleanolic acid exerts an osteoprotective effect in ovariectomy-induced osteoporotic rats and stimulates the osteoblastic differentiation of bone mesen- chymal stem cells in vitro. Menopause, 2011.
[31] T. Honda, B. V. Rounds, G. W. Gribble, et al. Design and synthesis of 2-cyano-3, 12-dioxoolean-1, 9-dien-28-oic acid, a novel and highly active inhibitor of oxide production in mouse macrophages. Bioorganic & Medicinal Chemistry Letters, 1998, 8(19): 2711-2714.
[32] N. Suh, Y. Wang, T. Honda, et al. A novel synthetic oleanane triterpenoid, 2-cyano-3, 12-dioxooleana-1, 9-dien-28-oic-acid, with potent differentiating, anti-proliferative, and anti-inflamma- tory activity. Cancer Research, 1999, 59(2): 336-341.
[33] T. Honda, T. Janosik, Y. Honda, et al. Design, synthesis, and biological evaluation of biotin conjugates of 2-cyano-3, 12-dio- xooleana-1, 9(11)-dien-28-oic acid for the isolation of the protein targets. Journal of Medicinal Chemistry, 2004, 47(20): 4923- 4932.
[34] T. Honda, Y. Honda, F. G. Favaloro, et al. A novel dicyano- triterpenoid, 2-cyano-3, 12-dioxooleana-1, 9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production. Bioorganic & Medicinal Chemistry Letters, 2002, 12(7): 1027-1030.
[35] 汤杰, 李佳, 王博等. 山楂酸衍生物及其制备和应用[P]. 中国专利: 200910055852. X, 2010-01-06.
[36] Y. Wei, C. M. Ma and M. Hattori. Synthesis and evaluation of A-seco typetriterpenoids for anti-HIV-1 protease activity. Euro- pean Journal of Medicinal Chemistry, 2009, 44(10), 4112-4120.
[37] 张奕华, 丁晔, 赖宜生等. 一类五环三萜-13,28-内酯化合物、其制备方法和用途[P]. 中国专利: 201010580457.8, 2011- 06-11.
[38] Y. Zhang, J. X. Li, J. W. Zhao, et al. Synthesis and activity of Oleanolic acid derivatives, a novel class of inhibitors of osteoclast formation. Bioorganic & Medicinal Chemistry Letters, 2005, 15(6): 1629-1632.
[39] W. Xu, L. Z. Liu, M. Loizidou, et al. The role of nitric oxide in cancer. Cell Research, 2002, 12(5-6): 311-320.
[40] L. Chen, Y. H. Zhang, X. W. Kong, et al. Synthesis and biological evaluation of nitric oxide-releasing derivatives of Oleanolic acid as inhibitors of HepG2 cell apoptosis. Bioorganic & Medicinal Chemistry Letters, 2007, 17(11): 2979-2982.
[41] L. Chen, Y. H. Zhang, X. W. Kong, et al. Design, synthesis and anti-hepatocellular carcinoma activity of nitric oxide-releasing derivatives of Oleanolic acid. Journal of Medicinal Chemistry, 2008, 51(15): 4834-4838.
[42] 陈莉, 孟飞, 王志凤等. 硝酸酯类NO供体型齐墩果酸衍生物的合成及抗肿瘤活性[J]. 中国药科大学学报, 2010, 41(6): 487-492.
[43] 陈秀英, 季晖, 张奕等. 一氧化氮供体型齐墩果酸衍生物ZCⅡ2对早期实验性肝纤维化的保护作用[J]. 中国临床药理学与治疗学, 2005, 10(11): 1261-1265.
[44] S. Qian, H. J. Li, Y. Chen, et al. Synthesis and Biological Evaluation of Oleanolic Acid Derivatives as Inhibitors of Protein Tyrosine Phosphatase 1B. Journal of Natural Products, 2010, 73(11): 1743-1750,
[45] 郭甜甜. 齐墩果酸皂苷的合成和生物活性评价以及羟基喜树碱缀合物的设计[D]. 中国海洋大学, 2010.
[46] Y. Q. Hua, Z. Y. Zhang, J. X. Li, et al. Oleanolic acid derivative Dex-OA has potent anti-tumor and anti-metastatic activity on osteosarcoma cells in vitro and in vivo. Investigational New Drugs, 2011, 29(2): 258-269.
[47] 闫茂才. 齐墩果酸衍生物的设计、合成与生物活性研究[D].沈阳药科大学, 2008.
[48] D. Huang, Y. Ding, Y. Li, et al. Antitumor activity of a 3-oxo derivative of Oleanolic acid. Cancer Letters, 2006, 23(2): 289- 296.
[49] 孙华, 胡春, 方唯硕. 3-氧代齐墩果酸氨基酸偶联物的合成、水溶性的测定及抗肿瘤活性研究[J]. 中国药物化学杂志, 2008, 18(11): 11-15.

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