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化学进展 2011, Vol. 23 Issue (01): 181-191 前一篇   后一篇

• 综述与评论 •

三萜骨架功能分子

胡君1, 巨勇1,2   

  1. 1. 清华大学化学系 生命有机磷化学及化学生物学教育部重点实验室 北京 100084;
    2. 兰州大学功能有机分子化学国家重点实验室 兰州 730000
  • 收稿日期:2010-06-01 修回日期:2010-08-01 出版日期:2011-01-20 发布日期:2011-09-02
  • 作者简介:e-mail:juyong@mail.tsinghua.edu.cn
  • 基金资助:

    国家自然科学基金项目(No.20772071,20972086)和高等学校博士点基金项目(No.20090002110060)资助

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Novel Functional Molecules Containing Triterpenoid Units

Hu Jun1, Ju Yong1,2   

  1. 1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China;
    2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2010-06-01 Revised:2010-08-01 Online:2011-01-20 Published:2011-09-02

具有独特立体结构的三萜化合物是一类重要的生物活性天然产物,在消炎、降血脂、保肝护肾、抗菌、抗肿瘤、抗真菌等方面有着重要药用价值。利用其独特手性结构、亲脂性、生物活性以及生物相容性等特性,设计合成新型功能分子,可作为药物载体,发挥其识别功能以及用于医用材料等方面具有重要的作用。本文介绍了近年来以三萜为骨架设计合成的新型功能分子在离子、分子识别和自组装性能方面研究现状及其潜在的应用前景。

关键词： 三萜, 手性骨架, 功能分子, 识别, 自组装

Triterpenoids, which mainly comes from natural medicinal plants, is used for the treatment of anti-inflammation, anti-virus, anti-tumor, anti-bacteria and anti-fungal activities. Due to the characteristic stereostructure, hydrophobic property, biological activity and biocompatibility, to design and synthesize new functional molecules with triterpenoid chiral skeleton is significant in the potential drug delivery, molecular recognition and medicinal materials, etc. In this review, the recent development of the functional molecules containing triterpenoid units are briefly summarized in the bioactivities, recognition and self-assembly.

Key words: triterpenoid, chiral skeleton, functional molecules, recognition, self-assembly

中图分类号: 

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[1] 张本印(Zhang B Y), 王环(Wang H), 沈建伟(Shen J W), 杨晓艳(Yang X Y), 罗晓东(Luo X D), 张晓峰(Zhang X F). 化学进展(Progress in Chemistry), 2010, 22(5): 877—887
[2] Wang C H, Levis G B S, Lee E B, Levis W R, Lee D W, Kim B S, Park S Y, Park E. Int. Immunopharmacol., 2004, 4: 1039—1049
[3] Zhang H J, Lu Z Z, Tan G T, Qiu S X, Farnsworth N R, Pezzuto J M, Fong H H S. Tetrahedron Lett., 2002, 43: 973—977
[4] Dini I, Schettino O, Simioli T, Dini A. J. Agr. Food. Chem., 2001, 49: 741—746
[5] Hirooka M, Kaji E, Zen S. Yakugaku Zasshi, 1990, 110: 958—963
[6] Janiszowka W, Wilkomirski B, Kasprzyk Z. Pol. J. Chem., 1988, 62: 403—407
[7] Sun J S, Han X W, Yu B. Org. Lett., 2005, 7: 1935—1938
[8] Lichtenthaler H K. Annu. Rev. Plant Physiol. Plant Mol. Biol., 1999, 50: 47—65
[9] Szakiel A, Grzelak A, Dudek P, Janiszowska W. Plant Physiol. Biochem., 2003, 41: 271—275
[10] Tezuka Y, Honda K, Banskota A H, Thet M M, Kadota S. J. Nat. Prod., 2000, 63: 1658—1664
[11] Abdel-Kader M, Hoch J, Berger J M, Evans R, Miller J S, Wisse J H, Mamber S W, Dalton J M, Kingston D G I. J. Nat. Prod., 2001, 64: 536—539
[12] Sun J S, Han X W, Yu B. Carbohyd. Res., 2003, 338: 827—833
[13] Wang P, Wang J, Guo T T, Li Y X. Carbohyd. Res., 2010, 345: 607—620
[14] Verma P, Mukhopadhyay B. Carbohyd. Res., 2009, 344: 2554—2558
[15] Rajput V K, Mukhopadhyay B. J. Org. Chem., 2008, 73: 6924—6927
[16] Gauthier C, Legault J, Pichette A. Mini. Rev. Org. Chem., 2009, 6: 321—344
[17] Marciani D J, Press J B, Reynolds R C, Pathak A K, Pathak V, Gundy L E, Farmer J T, Koratich M S, May R D. Vaccine, 2000, 18: 3141—3151
[18] Zhang Y, Li J X, Zhao J W, Wang S Z, Pan Y, Tanaka K, Kadota S. Bioorg. Med. Chem. Lett., 2005, 15: 1629—1632
[19] Hichri F, Ben J H, Cheriaa J, Jegham S, Mighri Z. C. R. Chim., 2003, 6: 473—483
[20] Honda T, Rounds B V, Bore L, Favaloro F G, Suh N, Wang Y P, Sporn M B, Gribble G W. J. Med. Chem., 2000, 43: 4233—4246
[21] Honda T, Honda Y, Favaloro F G, Suh N, Place A E, Rendi M H, Sporn M B. Bioorg. Med. Chem. Lett., 2002, 12: 1027—1030
[22] Honda T, Janosik T, Honda Y, Han J, Liby K T, Williams C R, Couch R D, Anderson A C, Sporn M B, Gribble G W. J. Med. Chem., 2004, 47: 4923—4932
[23] Honda T, Gribble G W, Suh N, Finlay H J, Rounds B V, Bore L, Favaloro F G, Wang Y P, Sporn M B. J. Med. Chem., 2000, 43: 1866—1877
[24] Honda Y, Honda T, Roy S, Gribble G W. J. Org. Chem., 2003, 68: 4991—4993
[25] Wen X A, Sun H B, Liu J, Wu G Z, Zhang L Y, Wu X M, Ni P Z. Bioorg. Med. Chem. Lett., 2005, 15: 4944—4948
[26] Wen X A, Zhang P, Liu J, Zhang L Y, Wu X M, Ni P Z, Sun H B. Bioorg. Med. Chem. Lett., 2006, 16: 722—726
[27] Finlay H J, Honda T, Gribble G W. ARKIVOC, 2002, 38—46
[28] Chen J, Liu J, Zhang L Y, Wu G Z, Hua W Y, Wu X M, Sun H B. Bioorg. Med. Chem. Lett., 2006, 16: 2915—2919
[29] Flekhter O B, Boreko E I, Nigmatullina L R, Pavlova N I, Medvedeva N I, Nikolaeva S N, Tret'yakova E V, Savinova O V, Baltina L A, Karachurina L T, Galin F Z, Zarudii F S, Tolstikov G A. Pharm. Chem. J., 2004, 38: 148—152
[30] Parra-Delgado H, Ramírez-Apan T, Martínez-Vázquez M. Bioorg. Med. Chem. Lett., 2005, 15: 1005—1008
[31] Parra-Delgado H, Compadre C M, Ramírez-Apan T, Munoz-Fambuena M J, Compadre R L, Ostrosky-Wegman P, Martinez-Vazquez M. Bioorg. Med. Chem., 2006, 14: 1889—1901
[32] Rounds W D, Eaton J T, Urbanowicz J H, Gribble G W. Tetrahedron Lett., 1988, 50: 6557—6560
[33] Caldwell C G, Franzblau S G, Suarez E, Timmermann B N. J. Nat. Prod., 2000, 63: 1611—1614
[34] Finlay H J, Honda T, Gribble G W, Danielpour D, Benoit N E, Suh N, Williams C, Sporn M B. Bioorg. Med. Chem. Lett., 1997, 7: 1769—1772
[35] Sejbal J, Homolova M, Tislerova I, Krecek V. Collect. Czech. Chem. Commun., 2000, 65: 1339—1356
[36] Shirota O, Tamemura T, Morita H, Takeya K. Itokawa H. J. Nat. Prod., 1996, 59: 1072—1075
[37] García-Granados A, Melguizo E, Parra A, Simeo Y, Viseras B, Dobado J A, Molina J, Arias J M. J. Org. Chem., 2000, 65: 8214—8223
[38] García-Granados A, López P E, Melguizo E, Moliz J N, Parra A, Simeo Y, Dobado J A. J. Org. Chem., 2003, 68: 4833—4844
[39] Medvedeva N I, Flekhter O B, Tretyakova E V, Galin F Z, Baltina L A, Spirikhin L V, Tolstikov G A. Russ. J. Org. Chem., 2004, 40: 1092—1097
[40] Medvedeva N I, Flekhter O B, Baltina L A, Galin F Z, Tolstikov G A. Chem. Nat. Compd., 2004, 40: 247—249
[41] 胡君(Hu J), 吴洋(Wu Y), 赵长崎(Zhao C Q), 巨勇(Ju Y). 高等学校化学学报(Chem. J. Chinese Universities), 2010, 31: 1762—1768
[42] García-Granados A, Dueňas J, Melguizo E, Moliz J N, Parra A, Perez F L, Dobado J A, Molina J. J. Chem. Res. S, 2000, 211—212
[43] García-Granados A, López P E, Melguizo E, Parra A, Simeo Y. Tetrahedron Lett., 2003, 44: 6673—6677
[44] García-Granados A, López P E, Melguizo E, Parra A, Simeo Y. Tetrahedron, 2004, 60: 1491—1503
[45] Assefa H, Nimrod A, Walker L, Sindelar R. Bioorg. Med. Chem. Lett., 1999, 9: 1889—1894
[46] Assefa H, Nimrod A, Walker L, Sindelar R. Bioorg. Med. Chem. Lett., 2001, 11: 1619—1623
[47] Davis A P, Perry J J, Williams R P. J. Am. Chem. Soc., 1997, 119: 1793—1974
[48] Rai R, Khatri V K, Pandey P S. Supramol. Chem., 2004, 16: 581—585
[49] Rai R, Pandey P S. Bioorg. Med. Chem. Lett., 2005, 15: 2923—2925
[50] Khatri V K, Upreti S, Pandey P S. Org. Lett., 2006, 8: 1755—1758
[51] Chattopadhyay P, Pandey P S. Tetrahedron, 2006, 62: 8620—8624
[52] Chahar M, Upreti S, Pandey P S. Tetrahedron, 2007, 63: 171—176
[53] Khatri V K, Chahar M, Pavani K, Pandey P S. J. Org. Chem., 2007, 72: 10224—10226
[54] Chattopadhyay P, Pandey P S. Tetrahedron Lett., 2008, 49: 4640—4643
[55] Kumar A, Pandey P S. Org. Lett., 2008, 10: 165—168
[56] Chahar M, Pandey P S. Tetrahedron, 2008, 64: 6488—6493
[57] Chattopadhyay P, Nagpal R, Pandey P S. Aust. J. Chem., 2008, 61: 216—222
[58] Kumar A, Pandey P S. Tetrahedron Lett., 2009, 50: 5842—5845
[59] Bonar-Law R P, Davis A P, Dorgan B J. Tetrahedron, 1993, 49: 9855—9866
[60] Bonar-Law R P, Davis A P, Murray B A. Angew. Chem. Int. Ed., 1990, 29: 1407—1408
[61] Bhattarai K M, Bonar-Law R P, Davis A P. J. Chem. Soc. Chem. Commun., 1992, 752—754
[62] Davis A P, Gilmer J F, Perry J J. Angew. Chem. Int. Ed., 1996, 35: 1312—1315
[63] Mckenna J, Mckenna J M, Thornthwaite D W. J. Chem. Soc. Chem. Commun., 1977, 809—811
[64] Borrows C J, Saute R A. J. Inclusion. Phenom., 1987, 5: 117—121
[65] Segura M, Alcazar V, Prados P, de Mendoza J. Tetrahedron, 1997, 53: 13119—13128
[66] Ahera N G, Pore V S, Patil S P. Tetrahedron, 2007, 24: 12927—12934
[67] Zhang Z, Ju Y, Zhao Y F. Chem. Lett., 2007, 36: 1450—1451
[68] Joachimiak R, Paryzek Z. J. Inclusion. Phenom., 2004, 49: 4600—4606
[69] Maitra U, Dsouza L J. J. Chem. Soc. Chem. Commun., 1994, 2793—2795
[70] Maitra U, Rao P, Kumar P, Balasubramanian R, Mathew L. Tetrahedron Lett., 1998, 39: 3255—3258
[71] Ghosh S, Choudhury A R, Guru Row T N, Maitra U. Org. Lett., 2005, 7: 1441—1444
[72] Chahar M, Upreti S, Pandey P S. Tetrahedron, 2007, 63: 171—176
[73] Li Y, Li G T, Wang X Y, Lin C X, Zhang Y H, Ju Y. Chem. Eur. J., 2008, 14: 10331—10339
[74] Turkmen Z, Klymchenko A S, Oncul S, Duportail G, Topcu G, Demchenko A P. J. Biochem. Biophy. Meth., 2005, 64: 1—18
[75] Korovin A V, Tkachev A V. Russ. Chem. Bull., 2001, 50: 304—310
[76] Adams M M, Damani P, Perl N R, Won A, Hong F, Livingston P O, Ragupathi G, Gin D Y. J. Am. Chem. Soc., 2010, 132: 1939—1945
[77] Bhakuni R S, Shukla Y N, Tripathi A K, Prajapati V, Kumar S. Phytother. Res., 2002, 16: S68—S70
[78] Bag B G, Pramanik R S, Maity G C. Supramol. Chem., 2005, 17: 297—302
[79] Bag B G, von Kiedrowski G. Angew. Chem. Int. Ed., 1999, 38: 3713—3714
[80] Hu J, Zhang M, Yu L B, Ju Y. Bioorg. Med. Chem. Lett., 2010, 20: 4342—4345
[81] Hu J, Zhang M, Yu L B, Ju Y. Soft Matter, 2011, DOI: 10.1039/COSMO1392G
[82] Chattopadhyay P, Pandey P S. Bioorg. Med. Chem. Lett., 2007, 17: 1553—1557
[83] Bag B G, Maity G C, Pramanik S R. Supramol. Chem., 2005, 17: 383—385
[84] Bag B G, Maity G C, Dinda S K. Org. Lett., 2006, 8: 5457—5460
[85] Bag B G, Maity G C, Pramanik S R. Pramana, 2005, 65: 925—929
[86] Bag B G, Dinda S K, Dey P P, Mallia V A, Weiss R G. Langmuir, 2009, 25: 8663—8671
[87] Hu J, Zhang M, Ju Y. Soft Matter, 2009, 5: 4971—4974
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三萜骨架功能分子