Advances in the Synthesis and Biological Activities of Ocotillol-Type Saponins

doi:10.6023/cjoc201510022

Abstract

Ocotillol-type saponins are a kind of tetracyclic triterpenoid ginsenoside with a tetrahydrofuran ring in the side chain. Ocotillol-type saponins mainly exist in panax plants and possess anti-inflammatory, antibacterial, morphine-antagonis- tic, neuroprotective, cardioprotective effects, etc. There are less ocotillol-type saponins in natural plants. Recently, many studies on the semi-synthesis, absolute configuration confirmation using X-ray diffraction, effect of anti-myocardial ischemic and metabolism of 20(S)-ocotillol-type saponins have been reported. It was found that 24R-epimer and 24S-epimer had stereoselectivity in anti-ischemic effect and pharmacokinetics. In this paper, the advances of the separation, synthesis, absolute configuration confirmation, pharmacological activity, metabolism of ocotillol-type saponins are reviewed.

Key words: ocotillol-type ginsenoside, synthesis, absolute configuration confirmation, biological activities, metabolism

Cite this article

Xu Yangrong, Wang Wenzhi, Yang Jingjing, Li Xinli, Meng Qingguo. Advances in the Synthesis and Biological Activities of Ocotillol-Type Saponins[J]. Chin. J. Org. Chem., 2016, 36(4): 724-735.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Tanaka, O.; Yahara, S. Phytochemistry 1978, 17, 1353.
[2] Li, X.-G.; Zhang, L.-X.; Meng, X.-Y.; Hou, J.-R.; Zhang, J. J. Jilin Agric. Univ. 2006, 27, 645 (in Chinese). (李向高, 张连学, 孟祥颖, 侯集瑞, 张晶, 吉林农业大学学报, 2006, 27, 645.)
[3] Li, Y.-X.; Liu, S.-F.; Wang, X.-N. Chin. Tradit. Herb. Drugs 1995, 26, 540 (in Chinese). (李义侠, 刘淑芬, 王晓霓, 中草药, 1995, 26, 540.)
[4] Chen, S.; Staba, E.; Taniyasu, S.; Kasai, R.; Tanaka, O. Planta Med. 1981, 42, 406.
[5] Ma, X.-Y.; Shao, C.-J.; Xu, J.-D. Gin. Res. 1991, 4, 9 (in Chinese). (马兴元, 邵春杰, 徐景达, 人参研究, 1991, 4, 9.)
[6] Ma, S.-G.; Jiang, Y.-T.; Song, S.-J.; Wang, Z.-H.; Bai, J.; Xu, S.-X.; Liu, K. Acta Pharm. Sin. 2005, 40, 924 (in Chinese). (马双刚, 姜永涛, 宋少江, 王振华, 白景, 徐绥绪, 刘珂, 药学学报, 2005, 40, 924.)
[7] Liu, J.-P.; Wang, F.; Li, P.-Y.; Lu, D. Nat. Prod. Res. 2012, 26, 731.
[8] Han, L.; Lin, M.-Y.; Zheng, Q.; Liu, H.-Y.; Liu, H.-Y.; Dong, G.; Liu, J.-P.; Li, P.-Y. Nat. Prod. Res. 2014, 28, 935.
[9] Morita, T.; Kasai, R.; Tanaka, O.; Zhou, J.; Yang, T.-R.; Shoji, J. Chem. Pharm. Bull. 1982, 30, 4341.
[10] Zou, K.; Zhu, S.; Tohda, C.; Cai, S.; Komatsu, K. J. Nat. Prod. 2002, 65, 346.
[11] Tanaka, O.; Morita, T.; Kasai, R.; Kinouchi, J.; Sanada, S.; Ida, Y.; Shoji, J. Chem. Pharm. Bull. 1985, 33, 2323.
[12] Namba, T.; Matsushige, K.; Morita, T.; Tanaka, O. Chem. Pharm. Bull. 1986, 34, 730.
[13] Morita, T.; Kong, Y.-C.; But, P. P.-P.; Ng, K.-H.; Yip, T.-T.; Kasai, R.; Tanaka, O. Chem. Pharm. Bull. 1986, 34, 4368.
[14] Nguyen, M.; Nguyen, T.; Kasai, R.; Ito, A.; Yamasaki, K.; Tanaka, O. Chem. Pharm. Bull. 1993, 41, 2010.
[15] Duc, N. M.; Kasai, R.; Ohtani, K.; Ito, A.; Nham, N. T.; Yamasaki, K.; Tanaka, O. Chem. Pharm. Bull. 1994, 42, 115.
[16] Meng, Q.-G.; Liu, L.-D.; Guo, H.-M.; Bi, Y.; Wang, L. Acta Crystallogr., Sect. E Struct. Rep. Online 2010, 66, o3210.
[17] Wang, C.-C. M.S. Thesis, Jilin University, Jilin, 2011 (in Chinese). (王晨晨, 硕士论文, 吉林大学, 吉林, 2011.)
[18] Liu, J.-P. Ph.D. Dissertation, Shenyang Pharmaceutical University, Shenyang, 2005 (in Chinese). (刘金平, 博士论文, 沈阳药科大学, 沈阳, 2005.)
[19] Vilotijevic, I.; Jamison, T. F. Angew. Chem., Int. Ed. Engl. 2009, 48, 5250.
[20] Koert, U.; Wagner, H.; Matthias, S. Tetrahedron Lett. 1994, 35, 7629.
[21] Nacro, K.; Baltas, M.; Zedde, C.; Gorrichon, L.; Jaud, J. Tetrahedron 1999, 55, 5129.
[22] Vilotijevic, I.; Jamison, T. F. Mar. Drugs 2010, 8, 763.
[23] Dai, L. M. S. Thesis, Jilin University, Jilin, 2010 (in Chinese). (戴璐, 硕士论文, 吉林大学, 吉林, 2010).
[24] Tian, X. M. S. Thesis, Jilin University, Jilin, 2012 (in Chinese). (田旭, 硕士论文, 吉林大学, 吉林, 2012.)
[25] Ren, Y.-Y. M.S. Thesis, Jilin University, Jilin, 2012 (in Chinese). (任媛媛, 硕士论文, 吉林大学, 吉林, 2012.)
[26] Meng, Q.-G.; Bi, Y.; Wang, L.; Jiang, N.-C.; Jiang, Y.-T.; Zhang, J.-F.; Yi, S.-T.; Sun, H.-J. Lett. Org. Chem. 2011, 8, 682.
[27] Zhang, L.; Guo, H.-M.; Li, W.-J.; Gao, Y.-J.; Meng, Q.-G. Acta Crystallogr., Sect. E Struct. Rep. Online 2011, 67, 846.
[28] Meng, Q.-G.; Tan, W.-J.; Hou, G.-G.; Zhang, X.-Y.; Hu, X.-Y.; Yang, F.; Bai, G.-J.; Zhu, W.-W.; Cai, Y.; Bi, Y. J. Mol. Struct. 2013, 1054, 1.
[29] Bi, Y.; Tian, J.; Wang, L.; Zhao, F.-L.; Zhang, J.-F.; Wang, N.; Sun, H.-J.; Meng, Q.-G. J. Med. Plants Res. 2011, 5, 2424.
[30] Wang, T.; Meng, Q.-G; Zhang, J.-F; Bi, Y.; Jiang, N.-C. Fitoterapia 2010, 81, 783.
[31] Bi, Y.; Tian, J.-W.; Ji, C.; Zhang, J.-F.; Wang, N.; Jiang, N.-C.; Sun, H.-J.; Meng, Q.-G. J. Med. Plants Res. 2011, 5, 6731.
[32] Bi, Y.; Wang, T.; Meng, Q.-G.; Zhang, J.-F.; Wang, L.; Li, Q.; Zhao, F.-L.; Sun, H.-J. Rec. Nat. Prod. 2012, 6, 24.
[33] Gao, L.-S.; Li, N.; Li, X. J. Shenyang Pharm. Univ. 2007, 24, 552 (in Chinese). (高璐莎, 李宁, 李铣, 沈阳药科大学学报, 2007, 24, 552.)
[34] Huang, Y.; Li, N.; Li, X.; Gao, L.-S.; Meng, D.-L. Acta Pharm. Sin. 2008, 43, 277 (in Chinese). (黄媛, 李宁, 李铣, 高璐莎, 孟大利, 药学学报, 2008, 43, 277.)
[35] Li, L.; Chen, X.-Y.; Li, D.; Zhong, D.-F. Drug Metab. Dispos. 2011, 39, 472.
[36] Zhang, G.-H.; Ma, C.-H.; Zhang, J.-J.; Chen, J.-W.; Tang, Q.-Y.; He, M.-H.; Xu, X.-Z.; Jiang, N.-H.; Yang, S.-C. BMC Genomics 2015, 16, 159.
[37] Li, Z.; Wu, C.-F.; Pei, G.; Guo, Y.-Y.; Li, X. Pharmacol., Biochem. Behav. 2000, 66, 595.
[38] Li, Z.; Xu, N.-J.; Wu, C.-F.; Xiong, Y.; Fan, H.-P.; Zhang, W.-B.; Sun, Y.; Pei, G. NeuroReport 2001, 12, 1453.
[39] Zhu, D. M. S. Thesis, Shenyang Pharmaceutical University, Shenyang, 2004 (in Chinese). (朱丹, 硕士论文, 沈阳药科大学, 沈阳, 2004.)
[40] Hao, Y.; Yang, J.-Y.; Wu, C.-F.; Wu, M.-F. Pharmacol., Biochem. Behav. 2007, 86, 660.
[41] Li, Z.; Guo, Y.; Wu, C.-F; Li, X.; Wang, J.-H. J. Pharm. Pharmacol. 1999, 51, 435.
[42] Wu, C.-F.; Liu, Y.-L.; Song, M.; Liu, W.; Wang, J.-H.; Li, X.; Yang, J.-Y. Pharmacol., Biochem. Behav. 2003, 76, 103.
[43] Wang, J.-Y.; Yang, J.-Y.; Wang, F.; Fu, S.-Y.; Hou, Y.; Jiang, B.; Ma, J.; Song, C.; Wu, C.-F. J. Evidence-Based Complementary Altern. Med. 2013, 2013.
[44] Wang, C.-M.; Liu, M.-Y.; Wang, F.; Wei, M.-J.; Wang, S.; Wu, C.-F.; Yang, J.-Y. Pharmacol., Biochem. Behav. 2013, 106, 57.
[45] Wang, Z.-J.; Sun, L.; Peng, W.; Ma, S.; Zhu, C.; Fu, F.; Heinbockel, T. Neuroscience 2011, 195, 1.
[46] Wang, X.-X.; Wang, C.-M.; Wang, J.-M.; Zhao, S.-Q.; Zhang, K.; Wang, J.-M.; Zhang, W.; Wu, C.-F.; Yang, J.-Y. Neuropharmacology 2014, 79, 642.
[47] Yu, C.; Fu, F.-H.; Jiang, Y.-T.; Yu, X.; Zhu, M.; Han, B. Chin. Tradit. Herb. Drugs 2007, 38, 576 (in Chinese). (于晨, 傅风华, 姜永涛, 于昕, 朱梅, 韩冰, 中草药, 2007, 38, 576.)
[48] Liu, J.-P.; Zhao, C.-F.; Li, P.-Y.; Li, X. J. Jilin Univ. (Med. Ed.) 2006, 32, 64 (in Chinese). (刘金平, 赵春芳, 李平亚, 李铣, 吉林大学学报(医学版), 2006, 32, 64.)
[49] Yu, C.; Fu, F.-H,; Yu, X.; Zhu, M. J. Mol. Cell. Cardiol. 2007, 42, S215.
[50] Jin, X.; Shen, W.-Z.; Jin, L.-F.; Jia, J.-Y.; Li, X.-F.; Wang, X.-L.; Di, X.; Zhang, H.-J.; Li, P.-Y. J. Jilin Univ. (Med. Ed.) 2013, 39(6), 1164 (in Chinese). (金鑫, 沈卫章, 金立方, 贾姣源, 李小丰, 王秀丽, 邸鑫, 张红娟, 李平亚, 吉林大学学报(医学版), 2013, 39(6), 1164.)
[51] Fu, X.-Y.; Kong, L.; Tang, M.; Zhang, J.-Q.; Zhou, X.-Y,; Li, G.; Wang, H.-B.; Fu, F.-H. Mol. Med. Rep. 2014, 9, 360.
[52] Zhao, B.; Fu, F.-H.; Wei, X.-B.; Chen, L.; Zhang, Y.-M. Chin. Pharmacol. Bull. 2008, 24, 87 (in Chinese). (赵冰, 傅风华, 魏欣冰, 陈琳, 张岫美, 中国药理学通报, 2008, 24, 87.)
[53] Liu, J.-P.; Lu, D.; Zhao, Y.; Li, P.-Y.; Li, X. J. Asian Nat. Prod. Res. 2007, 9, 103.
[54] Lee, S.-Y.; Jeong, J.-J.; Le, T. H. V.; Eun, S.-H.; Nguyen, M. D.; Park, J. H.; Kim, D.-H. J. Agric. Food Chem. 2015, 63, 7024.
[55] Jeong, J.-J.; Van Le, T.-H.; Lee, S.-Y.; Eun, S.-H.; Nguyen, M.-D.; Park, J.-H.; Kim, D.-H. Int. Immunopharmacol. 2015, 28, 700.
[56] Bi, Y.; Ma, C.; Zhang, H.-Y.; Zhou, Z.-W.; Yang, J.; Zhang, Z.-L.; Meng, Q.-G.; Lewis, P. J.; Xu, J.-Y. Chem. Biol. Drug Des. 2014, 84, 489.
[57] Bi, Y.; Ma, C.; Zhou, Z.-W.; Zhang, T.-T.; Zhang, H.-Y.; Zhang, X.-C.; Lu, J.; Meng, Q.-G.; Lewis, P. J.; Xu, J.-Y. Rec. Nat. Prod. 2015, 9.
[58] Bi, Y.; Yang, J.; Ma, C.; Liu, Z.-Y.; Zhang, T.-T.; Zhang, X.-C. Lu, J.; Meng, Q.-G. Pharmazie 2015, 70, 213.
[59] Bi, Y.; Yang, X.; Zhang, T.-T.; Liu, Z.-Y.; Zhang, X.-C.; Lu, J.; Cheng, K.-G.; Xu, J.-Y.; Wang, H.-B.; Lv, G.-Y.; Lewis, P. J.; Meng, Q.-G.; Ma, C. Eur. J. Med. Chem. 2015, 101, 71.
[60] Zhou, Z.; Ma, C.; Zhang, H.-Y.; Bi, Y.; Chen, X.; Tian, H.; Xie, X.-N.; Meng, Q.-G.; Lewis, P. J.; Xu, J.-Y. Eur. J. Med. Chem. 2013, 68, 444.
[61] Konoshima, T.; Takasaki, M.; Ichiishi, E.; Murakami, T.; Tokuda, H.; Nishino, H.; Duc, N. M.; Kasai, R.; Yamasaki, K. Cancer Lett. 1999, 147, 11.
[62] Yamasaki, K. Pharm. Biol. 2000, 38, 16.
[63] Wang, H.-B.; Yu, P.-F.; Bai, J.; Zhang, J.-Q.; Kong, L.; Zhang, F.-X.; Du, G.-Y.; Pei, S.; Zhang, L.; Jiang, Y.-T.; Tian, J.-W.; Fu, F.-H. J. Evidence-Based Complementary Altern. Med. 2013, 2013.
[64] Van Le, T. H.; Lee, S. Y.; Kim, T. R.; Kim, J. Y.; Kwon, S. W.; Nguyen, N. K.; Park, J. H.; Nguyen, M. D. J. Ginseng Res. 2014, 38, 154.
[65] Van Le, T. H.; Lee, S. Y.; Lee, G. J.; Nguyen, N. K.; Park, J. H.; Nguyen, M. D. J. Gineng Res. 2015, 39, 274.
[66] Ma, L.-Y.; Yang, X.-W. Phytochem. Lett. 2015, 13, 406.
[67] Wang, J.-H.; Li, X. Acta Pharm. Sin. 2001, 36, 427 (in Chinese). (王金辉, 李铣, 药学学报, 2001, 36, 427.)
[68] Zhao, C.-F.; Liu, J.-P.; Zhao, Y.; Li, P.-Y. China J. Chin. Mater. Med. 2008, 33, 432 (in Chinese). (赵春芳, 刘金平, 赵岩, 李平亚, 中国中药杂志, 2008, 33, 432.)
[69] Wu, X.-M.; Wang, L.; Ni, Y.-Y.; Wang, H.; Wang, W.-Y.; Meng, Q.-G. China J. Chin. Mater. Med. 2014, 39, 1306 (in Chinese). (吴祥猛, 王莉, 倪莹莹, 王慧, 王文艳, 孟庆国, 中国中药杂志,2014, 39, 1306.)
[70] Wang, W.-Y.; Wu, X.-M.; Wang, L.; Meng, Q.-G.; Liu, W.-H. PLoS One 2014, 9, e98887.
[71] Wang, W.-Y.; Wang, L.; Wu, X.; Xu, L.; Meng, Q.-G.; Liu, W.-H. Chirality 2015, 27, 170.
[72] Wang, W.-Y.; Ni, Y.-Y.; Wang, L.; Che, X.; Liu, W.-H.; Meng, Q.-G. Xenobiotica 2014, 45, 385.

Ocotillol型皂苷的合成与生物活性研究进展