中文
Earlier issues
Announcement
More
Progress in Chemistry 2012, Vol. 24 Issue (04): 545-555 Previous Articles   Next Articles

• Review •

Biomimetic Synthesis of Oligostilbenes

Li Wenling, Zang Peng, Li Hongfu, Yang Shixia   

  1. School of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, China
  • Received: Revised: Online: Published:
PDF ( 1335 ) Cited
Export

EndNote

Ris

BibTeX

Natural oligostilbenes are a class of plant polyphenols widely distributed in nature, and have received considerable attention in the chemical and biological fields because of their structural complexity as well as their diverse bioactivities. These oligomers and their derivatives are potentially useful leading compounds for drug development. Further investigations of structure-activity of oligostilbenes to screen active drugs were limited for their scarce availability in natural raw materials. Biosynthetic strategies towards these oligomers are studied widely and intensively by a number of chemists in recent years and has been a hot research topic. In this paper, the progress in the studies on the biomimetic synthesis of oligostilbenes over the past thirty years is reviewed in detail, including oxidative coupling reactions catalyzed by enzymes or metallic oxidants in various reaction mediums, isomerization under UV irradiation and cyclization induced by several strong acids. Diverse complex molecular architectures of oligostilbenes are thus constructed from a wide array of stilbene precursors through biomimetic routes. The future synthetic trend of oligostilbenes is also prospected.
Contents
1 Introduction
2 Biomimetic synthesis of oligostilbenes
2.1 Enzyme induced oxidative coupling reactions
2.2 Photochemical isomerization of oligostilbenes
2.3 Metallic oxidants catalyzed oligomerization
2.4 Cyclic dimerization catalyzed by acids
3 Conclusions and outlook
Key words: oligostilbenes, enzyme catalysis, biomimetic synthesis, oxidative coupling, isomerization

CLC Number: 

[1] 李娜 (Li N), 李小妹 (Li X M), 黄开胜 (Huang K S), 林茂(Lin M). 药学学报 (Acta Pharm. Sin.), 2001, 36: 944-950
[2] 李小妹 (Li X M), 李娜 (Li N), 黄开胜(Huang K S), 林茂(Lin M). 药学学报(Acta Pharm. Sin.), 2002, 37: 69-74
[3] Shen T, Wang X N, Lou H X. Nat. Prod. Rep., 2009, 26: 916-935
[4] Sotheeswaran S, Pasupathy V. Phytochemistry, 1993, 32: 1083-1092
[5] Lin M, Yao C S. Stud. Nat. Prod. Chem., 2006, 33: 601-644
[6] Langcake P, Pryce R J. Phytochemistry, 1977, 16: 1193-1196
[7] Langcake P, Pryce R J. J. Chem. Soc. Chem. Commun., 1977, 208-210
[8] Donnelly D M X, Murphy F G. J. Chem. Soc. Perkin Trans 1, 1987, 2719-2722
[9] Cichewicz R H, Kouzi S A, Hamann M T. J. Nat. Prod., 2000, 63: 29-33
[10] Nicotra S, Cramarossa M R, Mucci A, Pagnoni U M, Riva S, Forti L. Tetrahedron, 2004, 60: 595-600
[11] Takaya Y, Terashima K, Ito J, He Y H, Tateoka M, Yamaguchi N, Niwa M. Tetrahedron, 2005, 61: 10285-10290
[12] 李文玲(Li W L), 何侃侃(He K K), 李瀛(Li Y), 侯自杰(Hou Z J). 化学学报(Acta Chim. Sin.), 2005, 63: 1607-1612
[13] Ponzoni C, Beneventi E, Cramarossa M R, Raimondi S, Trevisi G, Pagnoni U M, Riva S, Forti L. Adv. Synth. Catal., 2007, 349: 1497-1506
[14] Li W L, Li H, Li Y, Hou Z J. Angew. Chem. Int. Ed., 2006, 45: 7609-7611
[15] Ito J, Niwa M. Tetrahedron, 1996, 52: 9991-9998
[16] Takaya Y, Yan K X, Terashima K, He Y H, Niwa M. Tetrahedron, 2002, 58: 9265-9271
[17] He Y H, Takaya Y, Terashima K, Niwa M. Heterocycles, 2006, 68: 93-100
[18] He S, Wu B, Pan Y J, Jiang L Y. J. Org. Chem., 2008, 73: 5233-5241
[19] Ito J, Gobaru K, Niwa M. Tetrahedron, 1998, 54: 6651-6660
[20] Baba K, Kido T, Kozawa M. Phytochemistry, 1994, 36: 1509-1513
[21] Kawabata J, Mishima M, Kurihara H. Phytochemistry, 1995, 40: 1507-1510
[22] Huang K S, Lin M, Wang Y H. Chin. Chem. Lett., 2000, 11: 1061-1062
[23] Zhou L X, Lin M. Chin. Chem. Lett., 2000, 11: 515-516
[24] 周立新(Zhou L X), 林茂(Lin M). 药学学报(Acta Pharm. Sin.), 2000, 35: 669-674
[25] Yao C S, Zhou L X, Lin M. Chem. Pharm. Bull., 2004, 52(2): 238-243
[26] Thomas N F, Lee K C, Paraidathathu T, Weber J F F, Awang K, Rondeau D, Richomme P. Tetrahedron, 2002, 58: 7201-7206
[27] Sako M, Hosokawa H, Ito T, Tinuma M. J. Org. Chem., 2004, 69: 2598-2600
[28] Takaya Y, Terashima K, Ito J, He Y H, Tateoka M, Yamaguchi N, Niwa M. Tetrahedron, 2005, 61: 10285-10290
[29] Velu S S, Buniyamin I, Ching L K, Feroz F, Noorbatcha I, Gee L C, Awang K, Wahab I A, Weber J F F. Chem. Eur. J., 2008, 14: 11376-11384
[30] Li W L, Li H F, Luo Y L, Yang Y H, Wang N. Synlett, 2010, 8: 1247-1250
[31] Li W L, Luo Y L, Li H F, Zang P, Han X Q. Synthesis, 2010, 22: 3822-3826
[32] Samaraweera U, Sotheeswaran S, Sultanbawa M U S. Phytochemistry, 1982, 21: 2585-2587
[33] Korhammer S, Reniero F, Mattivi F. Phytochemistry, 1995, 38: 1501-1504
[34] Aguirre J M, Alesso E N, Iglesias G Y M. J. Chem. Soc. Perkin Trans.1, 1999, 1353-1358
[35] Li X M, Huang K S, Lin M, Zhou L X. Tetrahedron, 2003, 59: 4405-4413
[36] Li X C, Ferreira D. Tetrahedron, 2003, 59: 1501-1507
[37] Takaya Y, Yan K X, Terashima K J, Ito J, Niwa M. Tetrahedron, 2002, 58: 7259-7265
[38] Takaya Y, Yan K X, Terashima K, He H Y, Niwa M. Tetrahedron, 2002, 58: 9265-9271
[39] Snyder S A, Breazzano S P, Ross A G, Lin Y Q, Zografos A L. J. Am. Chem. Soc., 2009, 131: 1753-1765
[40] Snyder S A, Zografos A L, Lin Y Q. Angew. Chem. Int. Ed., 2007, 46: 8186-8191
[41] Jeffrey J L, Sarpong R. Tetrahedron Lett., 2009, 50: 1969-1972
[42] Nicolaou K C, Wu T R, Kang Q, Chen D Y K. Angew. Chem. Int. Ed., 2009, 48: 3440-3443
[43] Kim I, Choi J. Org. Biomol. Chem., 2009, 7: 2788-2795
[44] Nicolaou K C, Kang Q, Wu T R, Lim C S, Chen D Y K. J. Am. Chem. Soc., 2010, 132: 7540-7548
[45] Snyder S A, Sherwood T C, Ross A G. Angew. Chem. Int. Ed., 2010, 49: 5146-5150
[1] Kelong Fan, Lizeng Gao, Hui Wei, Bing Jiang, Daji Wang, Ruofei Zhang, Jiuyang He, Xiangqin Meng, Zhuoran Wang, Huizhen Fan, Tao Wen, Demin Duan, Lei Chen, Wei Jiang, Yu Lu, Bing Jiang, Yonghua Wei, Wei Li, Ye Yuan, Haijiao Dong, Lu Zhang, Chaoyi Hong, Zixia Zhang, Miaomiao Cheng, Xin Geng, Tongyang Hou, Yaxin Hou, Jianru Li, Guoheng Tang, Yue Zhao, Hanqing Zhao, Shuai Zhang, Jiaying Xie, Zijun Zhou, Jinsong Ren, Xinglu Huang, Xingfa Gao, Minmin Liang, Yu Zhang, Haiyan Xu, Xiaogang Qu, Xiyun Yan. Nanozymes [J]. Progress in Chemistry, 2023, 35(1): 1-87.
[2] Yiqiang Liu, Yimei Qiu, Xing Tang, Yong Sun, Xianhai Zeng, Lu Lin. Glucose Isomerization into Fructose by Chemocatalytic Route [J]. Progress in Chemistry, 2021, 33(11): 2128-2137.
[3] Zhiyong Li, Ying Feng, Huiyong Wang, Xiaoqing Yuan, Yuling Zhao, Jianji Wang. Structure and Performance Modulation of Photo-Responsive Ionic Liquids [J]. Progress in Chemistry, 2019, 31(11): 1550-1559.
[4] Chen Mao Weng Yue Lei Aiwen. Asymmetric Cycloisomerization of 1,n-Enynes Catalyzed by Transition Metals [J]. Progress in Chemistry, 2010, 22(07): 1341-1352.
[5] Lu Yuhua Song Feijie Jia Xueshun Liu Yuanhong. Transition Metal-Catalyzed Synthesis of Furan Derivatives [J]. Progress in Chemistry, 2010, 22(01): 58-70.
[6] Li Xuqin Liu An. Inspiration from Protecting-Group-Free Synthesis [J]. Progress in Chemistry, 2010, 22(01): 81-90.
[7] Yang Yang Zheng Wen Cheng Dangguo Chen Fengqiu Zhan Xiaoli. The Application of in Situ FT-IR in the Research of Methane Oxidation [J]. Progress in Chemistry, 2009, 21(10): 2205-2211.
[8] Liang Jun|Wang Fuping*. Hydroisomerization of n-Alkane [J]. Progress in Chemistry, 2008, 20(04): 457-463.
[9] Linhui Tong Runhua Lu Yoshihisa Inoue Inoue . Asymmetric Photochemistry with Native and Modified Cyclodextrins [J]. Progress in Chemistry, 2006, 18(05): 533-541.
[10] Wang Hua,Liu Zhongmin*. Progress in Direct Conversion of Methane [J]. Progress in Chemistry, 2004, 16(04): 593-.
[11] Zhuang Yunlong,Yuan Yiguang,Zhang Rongliang. The Progress of Photoisomerizable Intellectual Biological Switches [J]. Progress in Chemistry, 2001, 13(04): 276-.
[12] Mao Chuanbin,Li Hengde,Cui Fuzhai,Feng Qingling,Wang Hao. Biomimetic Synthesis of Inorganic Materials [J]. Progress in Chemistry, 1998, 10(03): 246-.
[13] Xie Yuchun,Liu Huizhou,Chen Jiayong. Enzyme Catalyzed Chiral Resolution Process in Organic Solvent [J]. Progress in Chemistry, 1997, 9(03): 291-.
[14]

Wu Shikang

. Advances in the Research of Molecular Fluorescent Signal and Photocontrol Molecular Switching Devices [J]. Progress in Chemistry, 1994, 6(04): 301-.
Viewed
Full text


Abstract

Biomimetic Synthesis of Oligostilbenes