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2014 , Vol. 34 >Issue 8: 1692 - 1698

DOI: https://doi.org/10.6023/cjoc201402034

研究简报

异脱落酸的合成及植物生长调节活性

  • 韩小强 ,
  • 万川 ,
  • 杨冬燕 ,
  • 杜士杰 ,
  • 袁小勇 ,
  • 肖玉梅 ,
  • 覃兆海
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  • 中国农业大学理学院应化系 北京 100193

收稿日期: 2014-02-27

  修回日期: 2014-03-24

  网络出版日期: 2014-04-10

基金资助

国家自然科学基金（No.20972184）和国家高技术研究发展计划（No.2011AA10A206）资助项目

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Synthesis and Plant Growth Regulating Activities of iso-Abscisic Acid

  • Han Xiaoqiang ,
  • Wan Chuan ,
  • Yang Dongyan ,
  • Du Shijie ,
  • Yuan Xiaoyong ,
  • Xiao Yumei ,
  • Qin Zhaohai
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  • Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received date: 2014-02-27

  Revised date: 2014-03-24

  Online published: 2014-04-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 20972184) and the National Hi-Tech Research and Development Program of China (No. 2011AA10A206).

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摘要

通过空间位阻影响的选择性亲核加成、碳碳叁键的选择性还原以及Dess-Martin氧化和Lindgren氧化等反应合成了异脱落酸（11），同时还得到了2'，3'-二氢异脱落酸（12）、异炔酸（13）和异脱落酸内酯（14），经手性制备液相色谱分离得到了异脱落酸的两个对映异构体（+）-11和（-）-11. 以脱落酸（ABA）为对照，对异脱落酸类似物进行了植物生长调节活性测试，结果表明：异脱落酸（+）-11的活性略低于天然脱落酸，而（-）-11只具有很弱的活性；2'，3'-二氢异脱落酸（12）具有较低的活性，说明六元环上的双键是保持脱落酸活性的必需结构. 对比四种生测模式，异脱落酸类似物对莴苣种子萌发的效果最好.

关键词： 植物激素; 异脱落酸; 合成; 生物活性

本文引用格式

韩小强 , 万川 , 杨冬燕 , 杜士杰 , 袁小勇 , 肖玉梅 , 覃兆海 . 异脱落酸的合成及植物生长调节活性[J]. 有机化学, 2014 , 34(8) : 1692 -1698 . DOI: 10.6023/cjoc201402034

Abstract

The iso-abscisic acid (iso-ABA) analogs 11, 12, 13 and 14 were synthesized via regioselective addition of acetylides to enediones, selective reduction, Dess-Martin oxidation and Lindgren oxidation. The racemic mixtures 11 were resolved by chiral HPLC. These iso-ABA analogs and ABA were tested for their inhibitory activity in four bioassays. (+)-iso-ABA 11 exhibited high ABA-like activity, including the ability to effectively inhibit seed germination and seedling growth. The analogs 12, 13, 14 were also prepared and biological activities were investigated. Comparison of four bioassays, the iso-abscisic acid analogs had better activity in lettuce seed germination.

Key words： phytohormone; iso-abscisic acid analogs; synthesis; biological activities

参考文献

[1] Ohkuma, K.; Lyon, J. L.; Addicott, F. T.; Smith, O. E. Science 1963, 142, 1592.
[2] (a) Paton, D. M.; Dhawan, A. K.; Willing, R. R. Plant Physiol. 1980, 66, 254.
(b) Addicott, F. T.; Cams, H. R. In History and Introduction, Ed.: Addicott, F. T., Praeger Scientific, New York 1983, pp. 1～21.
(c) Chen, H. H.; Li, P. H.; Brenner, M. Plant Physiol. 1983, 71, 362.
(d) Li, Y.; Walton, D. C. Plant Physiol. 1987, 85, 910.
(e) Gusta, L. V.; O'Conner, J.; Reaney, M. Plant Growth Subst. 1988, 13, 531.
(f) Gusta, L. V.; O'Conner, J. B.; Laford, G. P. Plant Sci. 1994, 74, 63.
[3] (a) Zeevaart, J. A. D.; Creelman, R. A. Ann. Rev. Plant Physiol. Plant Mol. Biol. 1988, 39, 439.
(b) Davies, W. J.; Jones, H. G. Abscisic Acid, BIOS Scientific Publishers, Oxford, 1991.
[4] Todoroki, Y.; Hirai, N.; Koshimizu, K. Biotechnol. Biochem. 1994, 58, 707.
[5] (a) Balko, T. W.; Fields, S. C.; Webster, J. D. Tetrahedron Lett. 1999, 40, 6347.
(b) Kim, B. T.; Mina, Y. K.; Asamic, T.; Parka, N. K.; Jeongb, I. H.; Choa, K. Y.; Yoshida, S. Bioorg. Med. Chem. Lett. 1995, 5, 27.
[6] (a) Todoroki, Y.; Nakano, S.; Arai, S.; Hirai, N.; Ohigashi, H. Biosci. Biotechnol. Biochem. 1997, 61, 2043.
(b) Rose, P. A.; Cutler, A. J.; Irvine, N. M.; Shaw, A. C.; Squires, T. M.; Loewen, M. K.; Abrams, S. R. Bioorg. Med. Chem Lett. 1997, 7, 2543.
[7] Nyangulu, J. M.; Nelson, K. M.; Rose, P. A.; Gai, Y.; Loewen, M.; Lougheed, B.; Quail, J. W.; Culter, A. J.; Abrams, S. R. Org. Biomol. Chem. 2006, 4, 1400.
[8] Kim, B. T.; Min, Y. K.; Asami, T. Tetrahedron Lett. 1997, 38, 1797.
[9] Asami, T.; Kim, B. T.; Morita, K.; Abe, T.; Soh, C. H.; Murofushi, N.; Yoshida, S. Biosci. Biotechnol. Biochem. 1992, 56, 2089.
[10] Asami, T.; Yoshida, S. Heterocycles 1994, 38, 2739.
[11] Liu, W. J.; Han, X. Q.; Xiao, Y. M.; Fan, J. L.; Zhang, Y. Z.; Lu, H. Z.; Wang, M. A.; Qin, Z. H. Phytochemistry 2013, 96, 72.
[12] Todoroki, Y.; Nakano, S.; Hirai, N.; Ohigashi, H. Tetrahedron 1996, 52, 8081.
[13] Rose, P. A.; Abrams, S. R.; Gusta, L. V. Phytochemistry 1992, 31, 1105.
[14] Nakano, S.; Todoroki, Y.; Hirai, N.; Ohigashi, H. Biosci. Biotechnol. Biochem. 1995, 59, 1699.
[15] Todoroki, Y.; Nakano, N.; Hirai, N.; Mitsui, T.; Ohigashi, H. Biosci. Biotechnol. Biochem. 1997, 61, 1872.
[16] Todoroki, Y.; Hirai, N.; Koshimizu, K. Phytochemistry 1995, 40, 633.
[17] Rose, P. A.; Lei, B.; Shaw, A. C.; Barton, D.; Walker-Simmons, M. K.; Abrams, S. R. Phytochemistry 1996, 41, 1251.
[18] Han, X. Q.; Wan, C.; Yang, D. Y.; Yuan, X. Y.; Du, S. J.; Xiao, Y. M.; Qin, Z. H. Molecules 2013, 18, 10776.
[19] Uchiyama, M.; Ozawa, H.; Takuma, K.; Matsumoto, Y.; Yonehara, M.; Hiroya, K.; Sakamoto, T. Org. Lett. 2006, 8, 5517.
[20] Morris, C. F.; Anderberg, R. J.; Goldmark, P. J.; Walker-Simmons, M. K. Plant Physiol. 1991, 95, 814.
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