中文
Earlier issues
Announcement
More
Progress in Chemistry 2011, Vol. 23 Issue (01): 181-191 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
PDF ( 1396 ) Cited
Export

EndNote

Ris

BibTeX

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

CLC Number: 

[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
[1] Liangchun Li, Renlin Zheng, Yi Huang, Rongqin Sun. Self-Sorting Assembly in Multicomponent Self-Assembled Low Molecular Weight Hydrogels [J]. Progress in Chemistry, 2023, 35(2): 274-286.
[2] Liqing Li, Minghao Zheng, Dandan Jiang, Shuxin Cao, Kunming Liu, Jinbiao Liu. Colorimetric and Fluorescent Probes Based on the Oxidation of o-Phenylenediamine for the Detection of Bio-Molecules [J]. Progress in Chemistry, 2022, 34(8): 1815-1830.
[3] Meng Wang, He Song, Yewen Li. Three Dimensional Self-Assembled Blue Phase Liquid Crystalline Photonic Crystal [J]. Progress in Chemistry, 2022, 34(8): 1734-1747.
[4] Hang Yin, Zhi Li, Xiaofeng Guo, Anchao Feng, Liqun Zhang, San Hoa Thang. Selection Principle of RAFT Chain Transfer Agents and Universal RAFT Chain Transfer Agents [J]. Progress in Chemistry, 2022, 34(6): 1298-1307.
[5] Tianyu Zhou, Yanbo Wang, Yilin Zhao, Hongji Li, Chunbo Liu, Guangbo Che. The Application of Aqueous Recognition Molecularly Imprinted Polymers in Sample Pretreatment [J]. Progress in Chemistry, 2022, 34(5): 1124-1135.
[6] Hong Li, Xiaodan Shi, Jieling Li. Self-Assembled Peptide Hydrogel for Biomedical Applications [J]. Progress in Chemistry, 2022, 34(3): 568-579.
[7] Yuling Liu, Tengda Hu, Yilian Li, Yang Lin, Borsali Redouane, Yingjie Liao. Fast Self-Assembly Methods of Block Copolymer Thin Films [J]. Progress in Chemistry, 2022, 34(3): 609-615.
[8] Dan Zhao, Changtao Wang, Lei Su, Xueji Zhang. Application of Fluorescence Nanomaterials in Pathogenic Bacteria Detection [J]. Progress in Chemistry, 2021, 33(9): 1482-1495.
[9] Chunping Ren, Wen Nie, Junqiang Leng, Zhenbo Liu. Reactive Fluorescent Probe for Hypochlorite [J]. Progress in Chemistry, 2021, 33(6): 942-957.
[10] Yena Feng, Shuhe Liu, Shubo Zhang, Tong Xue, Honglin Zhuang, Anchao Feng. Preparation of SiO2/Polymer Nanocomposites Based on Polymerization-Induced Self-Assembly [J]. Progress in Chemistry, 2021, 33(11): 1953-1963.
[11] Chuxuan Yan, Qinglin Li, Zhengqi Gong, Yingzhi Chen, Luning Wang. Organic Semiconductor Nanostructured Photocatalysts [J]. Progress in Chemistry, 2021, 33(11): 1917-1934.
[12] Han Zhang, Jiawang Ding, Wei Qin. Recent Advances in Peptide-Based Electrochemical Biosensor [J]. Progress in Chemistry, 2021, 33(10): 1756-1765.
[13] Kaiyu Zhang, Guowei Gao, Yansheng Li, Yu Song, Yongqiang Wen, Xueji Zhang. Development and Application of DNA Hydrogel in Biosensing [J]. Progress in Chemistry, 2021, 33(10): 1887-1899.
[14] Zixuan Wang, Yuefei Wang, Wei Qi, Rongxin Su, Zhimin He. Design, Self-Assembly and Application of DNA-Peptide Hybrid Molecules [J]. Progress in Chemistry, 2020, 32(6): 687-697.
[15] Dan-Wei Zhang, Hui Wang, Zhan-Ting Li. Macromolecular and Supramolecular Helical Tubes: Synthesis and Functions [J]. Progress in Chemistry, 2020, 32(11): 1665-1679.