积雪草酸药理作用及其衍生物的研究进展
Research Progress on Pharmacological Effects of Asiatic Acid and Its Derivatives

作者: 孟艳秋 , 鹿学宇 , 汤 义 , 曹 佳 , 刘立伟 :沈阳化工大学,辽宁 沈阳;

关键词: 积雪草酸积雪草酸衍生物药理作用结构修饰Asiatic Acid Asiatic Acid Derivatives Pharmacological Effects Structural Modification

摘要:
积雪草酸是一种乌苏烷型五环三萜酸,主要来源于伞形科植物积雪草。研究发现积雪草酸具有抗炎护肤、保肝、抑菌、抗抑郁、降血糖、抗肿瘤等药理作用。本文对积雪草酸的药理活性及结构修饰的研究进展进行综述并进行展望。

Abstract: Asiatic acid is a type of pentacyclic triterpene acid from Centella asiatica. It has been found that Asiatic acid has various of pharmacological effects, such as anti-inflammatory, hepatoprotective, antibacterial, anti-depressant, hypoglycemia, antitumor and so on. In this paper, the research progress of pharmacological activity of asiatic acid and its structural modification has been re-viewed and forecasted.

文章引用: 孟艳秋 , 鹿学宇 , 汤 义 , 曹 佳 , 刘立伟 (2015) 积雪草酸药理作用及其衍生物的研究进展。 合成化学研究, 3, 75-83. doi: 10.12677/SSC.2015.34012

参考文献

[1] 冯旭, 郭飞飞, 赵龙, 等. 积雪草酸药理作用及其结构修饰的研究进展[J]. 中草药, 2014, 45(7): 1037-1042.

[2] 刘华清, 许青云, 王天麟. 积雪草酸的研究进展[J]. 中国野生植物资源, 2014, 33(4): 30-33.

[3] Li, Y., Yang, F., Yuan, M.X., Jiang, L.J., Yuan, L., Zhang, X.W., et al. (2015) Synthesis and Evaluation of Asiatic Acid Derivatives as Anti-Fibrotic Agents: Structure/Activity Studies. Steroids, 96, 44-49. http://dx.doi.org/10.1016/j.steroids.2014.11.001

[4] Chasseaud, L.F., Fry, B.J., Hawkins, D.R., Lewis, J.D., Sword, I.P., Taylor, T., et al. (1971) Metabolism of Asiatic Acid, Madeeassic Acid and Asiatieoside in Rat. Arzneimittel-Forschung, 21, 1379-1384.

[5] Lee, Y.S., Jin, D.Q., Beak, S.M., Lee, E.S. and Kim, J.A. (2003) Inhibition of Ultraviolet-A-Modulated Signaling Pathways by Asiatic Acid and Ursolic Acid in HaCaT Human Keratinocytes. European Journal of Pharmacology, 476, 173-178. http://dx.doi.org/10.1016/S0014-2999(03)02177-0

[6] Maquart, F.X., Chastang, F., Simeon, A., Birembaut, P., Gillery, P. and Wegrowski, Y. (1999) Triterpenes from Centella asiatica Stimulate Extracellular Matrix Accumulation in Rat Experimental Wounds. European Journal of Dermatology, 9, 289-296.

[7] Masoko, P., Picard, J., Howard, R.L., Mampuru, L.J. and Eloff, J.N. (2010) In Vivo Antifungal Effect of Combretum and Terminalia Species Extracts on Cutaneous Wound Healing in Immunosuppressed Rats. Pharmaceutical Biology, 48, 621-632. http://dx.doi.org/10.3109/13880200903229080

[8] Li, T.J., Li, B., Qin, Y., et al. (2004) The Application of Asiatic Acid and Its Derivatives in the Preparation of Antidepressants. CN: 1543964.

[9] Yang, J., Chen, H., Zhang, L., Wang, Q. and Lai, M.-X. (2010) Anti-Diabetic Effect of Standardized Extract of Potentilla discolor Bunge and Identification of Its Active Components. Drug Development Research, 71, 127-132.

[10] 方春钱, 高静, 周军, 等. 积雪草酸对糖尿病大鼠心脏及其线粒体的保护作用[J]. 江苏大学学报: 医学版, 2010, 20(2): 157-165.

[11] Thuong, P.T., Jin, W.Y., Lee, J.P., Seong, R.S., Lee, Y.-M., Seong, Y.H., et al. (2005) Inhibitory Effect on TNF-Al- pha-Induced IL-8 Production in the HT29 Cell of Constituents from the Leaf and Stem of Weigela subsessilis. Archives of Pharmacal Research, 28, 1135-1141. http://dx.doi.org/10.1007/BF02972975

[12] Nguyen, X.N., Bui, H.T., Tran, H.Q., et al. (2011) A New Ursane-Type Triterpenoid Glycoside from Centella asiatica Leaves Modulates the Production of Nitric Oxide and Secretion of TNF-Alpha in Activated RAW 264.7 Cells. Bioorganic & Medicinal Chemistry Letters, 21, 1777-1781. http://dx.doi.org/10.1016/j.bmcl.2011.01.066

[13] Gohil, K.J., Patel, J.A. and Gajjar, A.K. (2010) Pharmacological Review on Centella asiatica: A Potential Herbal Cure-All. Indian Journal of Pharmaceutical Sciences, 72, 546-556. http://dx.doi.org/10.4103/0250-474X.78519

[14] Chong, N.J. and Aziz, Z. (2013) A Systematic Review of the Efficacy of Centella asiatica for Improvement of the Signs and Symptoms of Chronic Venous Insufficiency. Evidence-Based Complementary and Alternative Medicine, 2013, Article ID: 627182. http://dx.doi.org/10.1155/2013/627182

[15] 崔福贵. 积雪草酸衍生物在制备防治心、脑血管疾病的药物中的用途[P]. CN: 1582946A, 2005-2-23.

[16] Hsu, Y.-L., Kuo, P.-L., Lin, L.-T. and Lin, C.-C. (2005) Asiatic Acid, a Triterpene, Induces Apoptosis and Cell Cycle Arrest through Activation of Extracellular Signal-Regulated Kinase and p38 Mitogen-Activated Protein Kinase Pathways in Human Breast Cancer Cells. Journal of Pharmacology and Experimental Therapeutics, 313, 333-344. http://dx.doi.org/10.1124/jpet.104.078808

[17] Park, B.C., Bosire, K.O., Lee, E.S., Lee, Y.S. and Kim, J.-A. (2005) Asiatic Acid Induces Apoptosis in SK-MEL-2 Human Melanoma Cells. Cancer Letters, 218, 81-90. http://dx.doi.org/10.1016/j.canlet.2004.06.039

[18] Huang, Y.H., Zhang, S.H., Zhen, R.X., Xu, X.-D. and Zhen, Y.-S. (2004) Asiaticoside Inducing Apoptosis of Tumor Cells and Enhancing Anti-Tumor Activity of Vincristine. Chinese Journal of Cancer, 23, 1599-1604.

[19] 李萍, 丁建花, 顾兵, 等. 积雪草苷对实验大鼠乳腺增生的防治[J]. 南京医科大学学报(自然科学版), 2002, 22(6): 470-473.

[20] Lee, Y.S., Jin, D.-Q., Kwon, E.J., Park, S.H., Lee, E.-S., Jeong, T.C., et al. (2002) Asiatic Acid, a Triterpene, Induces Apoptosis through Intracellular Ca2+ Release and Enhance Expression of p53 in HepG2 Human Hepatoma Cells. Cancer Letters, 186, 83-91. http://dx.doi.org/10.1016/S0304-3835(02)00260-4

[21] 孙宏斌, 张丽颖, 柳军. 熊果烷型五环三萜氨基酸衍生物、其制备方法及其医药用途[P]. 中国专利: CN101337984A, 2009-01-07.

[22] Jew, S.S., Park, H.G. and Kim, H.D. (1998) Preparation of Asiatic Acid Derivatives Having Modified A-Ring as Anticancer and Liver-Protecting Agents. WO: 98/23575.

[23] 陈海生. 有机酸铂盐及其制备方法和在制备抗癌药物中的应用[P]. 中国专利: CN101289467A, 2008-10-22.

[24] 张蓉仙, 朱禹, 郭文洁, 等. 线粒体靶向的积雪草酸稀土配合物的合成及抗肿瘤活性[J]. 化学试剂, 2009, 31(12): 961-963.

[25] 姚其正, 李晶晶, 李耐三. 具有抗肿瘤作用的13-正-辛基小蘗碱新氧生物[P]. 中国专利: CN101012227A, 2007- 08-08.

[26] Finlay, H.J., Honda, T., Gribble, G.W., Danielpour, D., Benoit, N.E., Suh, N., et al. (1997) Novel A-Ring Cleaved Analogs of Oleanolic and Ursolic Acids which Affect Growth Regulation in NRP.152 Prostate Cells. Bioorganic & Medicinal Chemistry Letters, 7, 1769-1772.

[27] Li, J.-F., Huang, R.-Z., Yao, G.-Y., Ye, M.-Y., Wang, H.-S., Pan, Y.-M., et al. (2014) Synthesis and Biological Evaluation of Novel Aniline-Derived Asiatic Acid Derivatives as Potential Anticancer Agents. European Journal of Medicinal Chemistry, 86, 175-179. http://dx.doi.org/10.1016/j.ejmech.2014.08.003

[28] 薛箐, 王楠, 孟艳秋. 积雪草酸衍生物的合成及抗肿瘤活性的研究[J]. 沈阳化工大学学报, 2014, 28(1): 24-31.

[29] 孟艳秋, 张良峰, 张译, 等. 积雪草酸衍生物的合成及抗肿瘤活性研究[J]. 化学通报, 2015, 78(4): 358-363.

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