O-酰基化丝氨酸的合成及其对樱桃番茄乙烯合成量和果实硬度的影响
投稿时间:2017-04-17      点此下载全文 HTML
引用本文:胡堂路,王春燕,谭伟明,于春欣,刘少金,李召虎,段留生,等.O-酰基化丝氨酸的合成及其对樱桃番茄乙烯合成量和果实硬度的影响[J].农药学学报,2017,19(6):688-693.
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作者单位E-mail
胡堂路 中国农业大学 农学院/教育部植物生长调节剂工程研究中心, 北京 100193  
王春燕 中国农业大学 农学院/教育部植物生长调节剂工程研究中心, 北京 100193  
谭伟明 中国农业大学 农学院/教育部植物生长调节剂工程研究中心, 北京 100193  
于春欣 中国农业大学 农学院/教育部植物生长调节剂工程研究中心, 北京 100193  
刘少金 中国农业大学 农学院/教育部植物生长调节剂工程研究中心, 北京 100193  
李召虎 中国农业大学 农学院/教育部植物生长调节剂工程研究中心, 北京 100193  
段留生 中国农业大学 农学院/教育部植物生长调节剂工程研究中心, 北京 100193 duanlsh@cau.edu.cn 
基金项目:高等学校博士学科点专项科研基金(20130008130005)
中文摘要:通过L-丝氨酸与不同的酰氯在室温下反应,合成了8个未见文献报道的乙烯合成抑制剂O-酰基化丝氨酸(2a~2h),其结构通过核磁共振氢谱、碳谱及高分辨质谱确证。以氨乙氧乙烯基甘氨酸(aminoethoxyvinylglycine,AVG)为阳性对照,测定了目标化合物对樱桃番茄Lycopersivon esculentum Mill.乙烯合成量和果实硬度的影响,同时运用分子对接的方法分析了目标化合物与番茄1-氨基环丙烷羧酸(1-aminocyclopropane-1-carboxylic acid, ACC)合成酶(ACS, 1IAY)可能的结合模式。结果显示:大部分目标化合物具有延缓樱桃番茄果实软化和抑制乙烯合成的作用,其中化合物2c2h效果较为突出。用2c2h处理番茄后第5天,与空白对照相比,果实硬度分别提高27.62%和40.04%,均与AVG处理无显著性差异;2c2h对乙烯合成量的抑制率分别达71.89%和53.28%,其中2c处理的抑制效果显著优于AVG处理。分子对接方法分析结果表明:化合物2c与番茄ACS酶活性空腔的氨基酸残基有较好的相互作用,2c的羧基可与Ala54和Arg412的氨基形成氢键,从而占据ACS酶的活性空腔。O-酰基化丝氨酸类化合物结构简单,容易获取,对乙烯合成抑制剂的开发具有推动作用。
中文关键词:O-酰基化丝氨酸  樱桃番茄  乙烯合成抑制剂  果实硬度  氨乙氧乙烯基甘氨酸(AVG)  1-氨基环丙烷羧酸合成酶
 
Synthesis of O-acylatedserine and its effect on ethylene synthesis and fruit firmness of cherry tomato
Abstract:The eight novel inhibitors of ethylene biosynthesis were synthesized from L-serine reactions with acyl chlorides at room temperature, and their structures were confirmed by 1H and 13C NMR and HRMS. Fruit firmness and ethylene production were measured after cherry tomato (Lycopersivon esculentum Mill.) were treated with O-acylatedserines and aminoethoxyvinylglycine (AVG). Furthermore, the probable binding mode of (1-aminocyclopropane-1-carboxylic acid, ACC) synthase(ACS enzyme,1IAY) and target compound was analyzed using Molecular Docking method. The results showed most of the target compounds is able to delay cherry tomato fruit softening and inhibit ethylene biosynthesis. The effects of compounds 2c and 2h were more prominent, and the fruit firmness was increased by 27.62% and 40.04%, respectively, compared with the blank control on the 5th day after the treatment, and there was no significant difference with AVG treatment. 2c and 2h inhibited the synthesis of ethylene by 71.89% and 53.28% compared with the blank control, respectively. And the inhibition effect of 2c treatment was significantly higher than that of AVG. Analysis result of Molecular Docking method indicated that 2c showed strong interactions with tomatos ACC, and the carboxyl group of 2c could form hydrogen bonds with the amino groups of Ala54 and Arg412, thus occupying the active cavity of ACS enzyme. This type of compound has a simple structure and is easy to obtain and contributes to the development of ethylene synthesis inhibitors.
Key words:O-acylatedserines  cherry tomato  inhibitor of ethylene synthesis  fruit firmness  aminoethoxyvinylglycine(AVG)  ACS enzyme
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