油菜素内酯的首个非甾体模拟物的设计、合成及生物活性

Design, synthesis, and bioactivity of the first nonsteroidal mimetics of brassinolide.

作者信息

Andersen D L, Back T G, Janzen L, Michalak K, Pharis R P, Sung G C

机构信息

Department of Chemistry and Department of Biological Sciences, University of Calgary, Calgary, Alberta, Canada, T2N 1N4.

出版信息

J Org Chem. 2001 Oct 19;66(21):7129-41. doi: 10.1021/jo015832+.

DOI:10.1021/jo015832+

PMID:11597241

Abstract

Ten novel compounds, each consisting of two subunits and a linker, were designed with the aid of molecular modeling to resemble the natural steroidal phytohormone brassinolide. The mimetics were synthesized and subjected to the rice leaf lamina inclination bioassay to test for brassinosteroid activity. Most of the mimetics displayed very weak or no bioactivity, but two were strongly active when coapplied with the auxin indole-3-acetic acid (IAA), which synergizes the activity of brassinosteroids. Thus, 1-(4,6 alpha,7 alpha-trihydroxy-5,6,7,8-tetrahydronaphthyl)-2-(6 alpha',7 alpha'-dihydroxy-5',6',7',8'-tetrahydronaphthyl)ethyne (4) and (E)-1,2-bis[trans-(4a alpha,8a beta)-4-oxo-6 alpha,7 alpha-dihydroxy-4a,5,6,7,8,8a-hexahydro-(3H)-naphthyl]ethylene (11) showed exceptional activity at doses as low as 0.01 ng and 0.001 ng/plant, respectively. These compounds are the first biologically active nonsteroidal brassinolide mimetics.

摘要

借助分子模拟设计了10种新型化合物，每种化合物由两个亚基和一个连接体组成，以模拟天然甾体植物激素油菜素内酯。合成了这些模拟物，并进行水稻叶片倾斜生物测定以测试油菜素内酯活性。大多数模拟物表现出非常弱的生物活性或无生物活性，但有两种与生长素吲哚 - 3 - 乙酸（IAA）共同施用时具有强活性，IAA可增强油菜素内酯的活性。因此，1 - （4,6α，7α - 三羟基 - 5,6,7,8 - 四氢萘基） - 2 - （6α'，7α' - 二羟基 - 5'，6'，7'，8' - 四氢萘基）乙炔（4）和（E） - 1,2 - 双[反式 - （4aα，8aβ） - 4 - 氧代 - 6α，7α - 二羟基 - 4a，5,6,7,8,8a - 六氢 - （3H） - 萘基]乙烯（11）分别在低至0.01 ng和0.001 ng/株的剂量下表现出优异的活性。这些化合物是首批具有生物活性的非甾体油菜素内酯模拟物。