English
往期目录
新闻公告
More
化学进展 2009, Vol. 21 Issue (0708): 1500-1506 前一篇   后一篇

• 综述与评论 •

白藜芦醇结构修饰及药理活性

刘华臣1,2,董爱君2,3,高春梅2,蒋宇扬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. 清华大学深圳研究生院广东省重点化学生物学实验室 |深圳 518055|3. 清华大学生物科学与技术系 |北京 100084)
  • 收稿日期:2008-09-15 修回日期:2008-12-08 出版日期:2009-08-24 发布日期:2009-06-30
  • 通讯作者: 蒋宇扬 E-mail:jiangyy@sz.tsinghua.edu.cn
  • 基金资助:

    863项目;973项目;国家自然科学基金

下载PDF ( 2844 ) 引用
导出 被引次数 ( 10 | 3 )

Structure Modification of Resveratrol and Pharmacological Activity

Liu Huachen1,2 ; |Dong Aijun2,3 ; |Gao Chunmei2 ; |Jiang Yuyang1,2*   

  1. ( 1.Key Laboratory of Bioorganic Phosphorus Chemistry &|Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, China|2.The Key Laboratory of Chemical Biology, Guangdong Province, Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, China|3.Department of Biological Science and Biotechnology, Tsinghua University, Beijing 100084, China )
  • Received:2008-09-15 Revised:2008-12-08 Online:2009-08-24 Published:2009-06-30
  • Contact: Jiang Yuyang E-mail:jiangyy@sz.tsinghua.edu.cn

从自然界中寻找活性先导化合物,再进行结构修饰,以提高化合物的活性和降低毒性是目前创新药物的一条重要思路。白藜芦醇是在葡萄等植物中广泛存在的植物抗毒素，对人类目前的疾病如肿瘤、心血管疾病、神经退化性疾病和病毒感染等具有良好的预防作用，是一种具有开发潜力的先导化合物。近年来越来越多的科学家对其进行结构改造以得到高活性化合物，例如对双键、苯环的修饰。本文就目前对白藜芦醇修饰及其药理活性进行阐述和讨论。

关键词： 白藜芦醇, 药理活性, 构效关系

In order to improve activity and decrease toxicity, searching for lead compounds with biological activity existed in the nature and modifying theirs structure is an important means of innovation new drugs. Resveratrol, a phytoalexin isolated from grapes and other plants, is well-known for its potent chemopreventive properties towards the most severe contemporary human diseases, such as cancer, vascular disease, neurodegenerative pathologies and viral infection, etc. In recent years, more and more scientists modify the double bond or benzene ring of resveratrol to get higher active, lower toxicity derivates. In this paper, the structure-activity relationships and pharmacological properties of the resveratrol derivatives as a potent chemopreventive agent are reviewed and discussed. 　　

Contents
1 Anti-tumor activity of resveratrol
2 Structure modification of resveratrol
2.1 Structure modification of resveratrol on ethylenic bond
2.2 Structure modification of resveratrol on benzene ring
3 Conclusion

Key words: resveratrol, pharmacological activity, structure-activity relationships

中图分类号: 

()

[ 1 ] 　Sanders T H , McMichael R W, Hendrix KW, et al . J . Agric. Food Chem. , 2000 , 48 : 1243 —1246
[ 2 ] 　Lyons M M, Yu C , Toma R B , et al . J . Agric. Food Chem. ,2003 , 51 : 5867 —5870
[ 3 ] 　Ibern M, Roig-Perez S , Lamuela R M, et al . J . Agric. Food Chem. , 2000 , 48 : 6352 —6354
[ 4 ] 　Gerogiannaki C M, Athanasopoulos P , Kyriakidis N , et al . Food Control , 2006 , 17 : 700 —706
[ 5 ] 　Counet C , Callemien D , Collin S. Food Chem. , 2006 , 98 : 649 —657
[ 6 ] 　Bavaresco L , Vezzulli S , Civardi S , et al . J . Agric. Food Chem. ,2008 , 56 : 2085 —2089
[ 7 ] 　Sobolev V S. J . Agric. Food Chem. , 2008 , 56 : 1949 —1954
[ 8 ] 　Zhang Y, Li S Z, Li J , et al . J . Am. Chem. Soc. , 2006 , 128 :13030 —13031
[ 9 ] 　Howitz KT, Bitterman KJ , Cohen H Y, et al . Nature , 2003 , 425 :191 —196
[10 ] 　Ener GS , Toklu H Z, Ehirli A O , et al . Hepatol . Res. , 2006 , 35 :62 —68
[11 ] 　Chan W H , Chang Y J . Toxicol . Lett . , 2006 , 161 : 1 —9
[12 ] 　Li Y, Cao Z, Zhu H. Pharmacol . Res. , 2006 , 53 : 6 —15
[13 ] 　Cengiz A , Hale K, Aysun B K, et al . J . Surg. Res. , 2005 , 127 :112 —117
[14 ] 　Kerem Z, Regev S G, Flaishman MA , et al . J . Nat . Prod. , 2003 ,66 : 1270 —1272
[15 ] 　Cignarella A , Minici C , Bolego C , Bolego I , Pelosl V , Puglisi L ,Gaion RM. ⅪⅤInternational Symposiumon Atherosclerosis , Rome :Elsevier , 2006. 18 —22
[16 ] 　Horn T L , Cwik M J , Morrissey R L , et al . Food and Chem.Toxicol . , 2007 , 45 : 55 —63
[17 ] 　张宝红(Zhang B H) . 现代医院(Modern Hospital ) , 2008 , 8(3) : 66 —68
[18 ] 　李旭波(Li X B) , 谢人明(Xie R M) . 西部药学(Pharmacy of West China) , 2007 , 4 (1) : 37 —39
[19 ] 　Liu H , Dong A , Gao C , et al . Bioorg. Med. Chem. , 2008 , 16 :10013 —10021
[20 ] 　Surh Y J . Nat . Rev. Cancer , 2003 , 3 : 768 —780
[21 ] 　Jang M, Cai L , Udeani GO , et al . Science , 1997 , 275 : 218 —220
[22 ] 　Kelloff GJ , Crowell J A , Steele V E , et al . J . Nutr. , 2000 , 130 :467S —471S
[23 ] 　Gusman J , Malonne H , Atasst G, et al . Carcinogenesis , 2001 , 22 :1111 —1117
[24 ] 　Fontecave M, Lepoivre M, Elleingand E , et al . FEBS Lett . , 1998 ,421 : 277 —279
[25 ] 　Sun N J , Woo S , Cassady J M, et al . J . Nat . Prod. , 1998 , 61 :362 —366
[26 ] 　Kotha S , Jiang C W, Pedro M, et al . J . Biol . Chem. , 1998 , 273 :21875 —21882
[27 ] 　Suenaga F , Hatsushika K, Takano S , et al . FEBS Lett . , 2008 ,582 : 586 —590
[28 ] 　Kalra N , Roy P , Prasad S , et al . Life Sci . , 2008 , 82 : 348 —358
[29 ] 　Godichaud S , Si2Tayeb K, AugUN , et al . Int . J . Biochem. &Cell Biol . , 2006 , 38 : 629 —637
[30 ] 　Wang S , Wang X, Yan J , et al . Eur. J . Pharmacol . , 2007 , 567 :26 —35
[31 ] 　Notas G, Nifli A P , Kampa M, et al . Biochimica et Biophysica Acta , 2006 , 1760 : 1657 —1666
[32 ] 　Rakici O , Kiziltepe U , Coskun B , et al . Int . J . Cardiol . , 2005 ,105 : 209 —215
[33 ] 　Chander V , Chopra K. J . Surg. Res. , 2006 , 133 : 129 —135
[34 ] 　Garvina S , llingerb K O , Dabrosin C , et al . Cancer Lett . , 2006 ,231 : 113 —122
[35 ] 　Shimizu T, Nakazato J , Xian M J , et al . Biochem. Pharmacol . ,2006 , 71 : 742 —750
[36 ] 　Dolfini E , Roncoroni L , Dogliotti E. Cancer Lett . , 2007 , 249 :143 —147
[37 ] 　Pettit G R , Grealish M P , Jung M K, et al . J . Med. Chem. , 2002 ,45 : 2534 —2542
[38 ] 　Roberti M, Pizzirani D , Simoni D , et al . J . Med. Chem. , 2003 ,46 : 3546 —3554
[39 ] 　Cardile V , Lombardo L , Spatafora C , et al . Bioorganic Chemistry ,2005 , 33 : 22 —33
[40 ] 　Kageura T, Matsuda H , Morikawa T, et al . Bioorg. Med. Chem. ,2001 , 9 : 1887 —1893
[41 ] 　Simoni D , Roberti M, Invidiata F P , et al . Bioorg. Med. Chem.Lett . , 2006 , 16 : 3245 —3248
[42 ] 　Roberti M, Pizzirani D , Simoni D , et al . J . Med. Chem. , 2003 ,46 : 3546 —3554
[43 ] 　Pettit GR , Grealish M P , JungM K, et al . J . Med. Chem. , 2002 ,45 : 2534 —2542
[44 ] 　朱玉松(Zhu YS) , 罗世能(Luo S N) , 沈永嘉(Shen YJ ) 等. 有机化学(Chinese Journal of Organic Chemistry) , 2006 , 26 : 958 —962
[45 ] 　Solladie G, Pasturel J Y, Maignan J . Tetrahedron , 2003 , 59 :3315 —3321
[46 ] 　Panzella L , Lucia M D , Amalfitano C , et al . J . Org. Chem. ,2006 , 71 : 4246 —4254
[47 ] 　Tsai W J , Shiao Y J , Lin S J , et al . Bioorg. Med. Chem. Lett . ,2006 , 16 : 4440 —4443
[48 ] 　Lin S J , Shiao Y J , Chid C W, et al . Bioorg. Med. Chem. Lett . ,2004 , 14 : 1173 —1176
[49 ] 　Roberti M, Pizzirani D , Recanatini M, et al . J . Med. Chem. ,2006 , 49 : 3012 —3018
[50 ] 　Minutolo F , Sala G, Bagnacani A , et al . J . Med. Chem. , 2005 ,48 : 6783 —6786
[51 ] 　Song S , Lee H , Jin Y, et al . Bioorg. Med. Chem. , 2006 , 17 :461 —464
[52 ] 　Kim S , Ko H , Park J E , et al . J . Med. Chem. , 2002 , 45 : 160 —164
[53 ] 　Mu F , Hamel E , Lee D J , et al . J . Med. Chem. , 2003 , 46 :1670 —1682
[54 ] 　Zhou H B , Comninos J S , Stossi F , et al . J . Med. Chem. , 2005 ,48 : 7261 —7274
[55 ] 　Pagliai F , Pirali T, Grosso E D , et al . J . Med. Chem. , 2006 , 49 :467 —470
[56 ] 　Qu W, Kung M P , Hou C , et al . J . Med. Chem. , 2007 , 50 :3380 —3387
[57 ] 　Tron G C , Pagliai F , Grosso E D , et al . J . Med. Chem. , 2005 ,48 : 3260 —3268
[58 ] 　Pirali T, Busacca S , Beltrami L , et al . J . Med. Chem. , 2006 , 49 :5372 —5376
[59 ] 　Wang L , Woods K W, Li Q , et al . J . Med. Chem. , 2002 , 45 :1697 —1711
[60 ] 　Kim Y, Nam N H , You Y J , et al . Bioorg. Med. Chem. Lett . ,2002 , 12 : 719 —722
[61 ] 　Nam N H , Kim Y, You Y J , et al . Bioorg. Med. Chem. Lett . ,2002 , 12 : 1955 —1958
[62 ] 　Fuji K, Morimoto T, Tsutsumi K. Chem. Commun. , 2005 , 26 :3295 —3297
[63 ] 　Vilar S , Quezada E , Santana L , et al . Bioorg. Med. Chem. Lett . ,2006 , 16 : 257 —261
[64 ] 　Mortimer C G, Wells G, Crochard J P , et al . J . Med. Chem. ,2006 , 49 : 179 —185
[65 ] 　Russell W R , Scobbie L , Chesson A. Bioorg. Med. Chem. , 2005 ,13 : 2537 —2546
[66 ] 　Qin C X, Chen X, Hughes R A , et al . J . Med. Chem. , 2008 , 51 :1874 —1884
[67 ] 　Li W, Li H , Li Y, et al . Angew. Chem. Int . Ed. , 2006 , 45 :7609 —7611
[68 ] 　Nicolaou K C , Lister T, Denton R M, et al . Angew. Chem. Int .Ed. , 2007 , 46 : 7501 —7505
[69 ] 　Vessières A , Top S , Pigeon P , et al . J . Med. Chem. , 2005 , 48 :3937 —3940
[70 ] 　Mai A , Cheng D , Bedford M T, et al . J . Med. Chem. , 2008 , 51 :2279 —2290
[71 ] 　Reddy M V R , Mallireddigari M R , Cosenza S C , et al . J . Med.Chem. , 2008 , 51 : 86 —100
[72 ] 　Pandit B , Sun Y, Chen P , et al . Bioorg. Med. Chem. , 2006 , 14 :6492 —6501
[73 ] 　Jung J C , Jang S , Lee Y, et al . J . Med. Chem. , 2008 , 51 :4054 —4058
[74 ] 　Liou J P , Chang CW, Song J S , et al . J . Med. Chem. , 2002 , 45 :2556 —2562
[75 ] 　Eddarir S , Abdelhadib Z, Rolandoa C. Tetrahedron Lett . , 2001 ,42 : 9127 —9130
[76 ] 　Huang X F , Ruan B F , Wang X T, et al . Eur. J . Med. Chem. ,2007 , 42 : 263 —267
[77 ] 　Hauss F , Liu J W, Michelucci A , et al . Bioorg. Med. Chem.Lett . , 2007 , 17 : 4218 —4222
[78 ] 　Zhang W, Go ML. Eur. J . Med. Chem. , 2007 , 42 : 841 —850
[79 ] 　丁宁(Ding N) , 李英霞(Li Y X) , 褚世栋(Zhu S D) . 有机化学(Chinese Journal of Organic Chemistry) , 2004 , 24 : 898 —901
[80 ] 　Matsuoka A , Kodama Y, Fukuhara K, et al . Food Chem. Toxicol . ,2008 , 46 : 1125 —1130
[81 ] 　Fukuhara K, Nakanishi I , Matsuoka A , et al . Chem. Res.Toxicol . , 2008 , 21 : 282 —287
[82 ] 　Su B N , Cuendet M, Hawthorne M E , et al . J . Nat . Prod. , 2002 ,65 : 163 —169
[83 ] 　Heynekamp J J , Weber W M, Hunsaker L A , et al . J . Med.Chem. , 2006 , 49 : 7182 —7189
[84 ] 　Lion C J , Matthews C S , Stevens M F G, et al . J . Med. Chem. ,2005 , 48 : 1292 —1295
[85 ] 　Murias M, Handle N , Erker T. Bioorg. Med. Chem. , 2004 , 12 :5571 —5578
[86 ] 　Chen G, Shan W, Wu Y L , et al . Chem. Pharm. Bull . , 2005 ,53 : 1587 —1590
[87 ] 　Botella L , Nà jera C. Tetrahedron , 2004 , 60 : 5563 —5570
[88 ] 　Qu W, Kung M P , Hou C , et al . J . Med. Chem. , 2007 , 50 :2157 —2165
[89 ] 　Andrus MB , Liu J . Tetrahedron Lett . , 2006 , 47 : 5811 —5814
[90 ] 　De Medina P , Casper R , Savouret J F , et al . J . Med. Chem. ,2005 , 48 : 287 —291
[91 ] 　Lee HJ , Seo J W, Lee B H , et al . Bioorg. Med. Chem. Lett . ,2004 , 14 : 463 —466
[92 ] 　Chang S , Na Y, Shin H J , et al . Tetrahedron Lett . , 2002 , 43 :7445 —7448
[93 ] 　Wang J X, Fu Y, Hu Y. Angew. Chem. Int . Ed. , 2002 , 41 :2757 —2760
[1] 武江洁星, 魏辉. 浅谈纳米酶的高效设计策略[J]. 化学进展, 2021, 33(1): 42-51.
[2] 闫新, 李意羡, 贾月梅, 俞初一. 糖苷化的亚氨基糖:分离、合成与生物活性[J]. 化学进展, 2019, 31(11): 1472-1508.
[3] 李意羡, 贾月梅, 俞初一. 氟代亚氨基糖的合成与糖苷酶抑制活性[J]. 化学进展, 2018, 30(5): 586-600.
[4] 朱燕燕, 岳宗洋, 边文, 刘瑞林, 马晓迅, 王晓东. 六铝酸盐结构及其在高温反应中的应用[J]. 化学进展, 2018, 30(12): 1992-2002.
[5] 代天志, 孙德群. 抗TB活性化合物的研究[J]. 化学进展, 2018, 30(11): 1784-1802.
[6] 刘如沁, 索志荣, 何乃珍, 陈爽, 黄明. 偶氮桥联二呋咱:合成及其分子结构-熔点的构效关系[J]. 化学进展, 2017, 29(5): 476-490.
[7] 胡代花, 陈旺, 王永吉. 活性维生素D3类似物的合成及构效关系研究[J]. 化学进展, 2016, 28(6): 839-859.
[8] 宋钊宁, 冯翔, 刘熠斌, 杨朝合, 周兴贵. 丙烯直接气相临氢环氧化催化剂结构调控和催化剂构-效关系研究进展[J]. 化学进展, 2016, 28(12): 1762-1773.
[9] 郭键, 贺耘, 叶新山. 唾液酸转移酶抑制剂的设计与发现[J]. 化学进展, 2016, 28(11): 1712-1720.
[10] 赵丽君, 雷鸣. 甲状腺结合前清蛋白的理论研究[J]. 化学进展, 2014, 26(01): 193-202.
[11] 童敏曼, 赵旭东, 解丽婷, 刘大欢*, 阳庆元, 仲崇立*. 金属-有机骨架材料用于废水处理[J]. 化学进展, 2012, (9): 1646-1655.
[12] 张鹭 侯玉霞 袁会珠 覃兆海. 复合物Ⅲ抑制剂型杀菌剂——结构类型和作用机理*[J]. 化学进展, 2010, 22(09): 1852-1868.
[13] 李征 李援朝. 结构多样性与构效关系——雷公藤新药研究与开发[J]. 化学进展, 2009, 21(12): 2483-2491.
[14] 张锁江 姚晓倩 刘晓敏. 离子液体构效关系及应用*[J]. 化学进展, 2009, 21(11): 2465-2473.
[15] 刘幸海,董卫莉,张传玉,王宝雷,马翼,李正名. KARI酶及其抑制剂[J]. 化学进展, 2008, 20(11): 1788-1797.
阅读次数
全文


摘要

白藜芦醇结构修饰及药理活性