CN114539354B - 一种杀线虫环肽化合物及其制备方法 - Google Patents
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Abstract
本发明公开了一种杀线虫环肽化合物及其制备方法和用途，所述环肽由9个氨基酸构成，其序列为cyclo(CKLPFLIPC)，其中两个Cys形成二硫键后成环。该环肽的分子式为C49H78N10O10S2，分子量为1031.34。本发明还涉及包含该杀线虫环肽制备方法和杀线虫用途。本发明所述杀线虫环肽采用固相合成法制备得到。杀线虫活性测试表明，本发明所述环肽对秀丽隐杆线虫致死率较为显著，可用于开发杀线虫药物。
Description
技术领域
本发明涉及农化与医药技术领域，具体涉及一种环肽化合物及其制备方法以及该化合物在杀线虫活性方面的应用。
背景技术
现在世界上已经发现的植物寄生线虫有 200 余属，5000 多种，在自然界中分布很广。许多植物寄生线虫生活于植物根际土壤中，除少数在茎、叶上产生典型症状外，大多数危害地下部，发病初期地上部没有明显症状。线虫危害有逐年加重的趋势，成为影响农业生产的重要因素。根结线虫病侵染农作物达数百种以上，大田作物、蔬菜、果树、花卉、药用植物等几乎每种作物均可受到侵染。根结线虫以二龄幼虫侵染植物根部，雌虫身体部分或全部的进入根部组织，然后逐渐膨大呈球形或椭圆形，最终形成胶质的卵囊，卵囊中的卵可以在恶劣环境中长期存活，在适宜的环境条件下即可以发育成二龄幼虫进行侵染。
植物寄生线虫通常采用化学杀线虫剂进行防治。防治线虫的药剂，称作杀线虫剂，简称杀线剂（Nematicides）。常见的杀线剂有熏蒸剂和触杀性杀线剂两类。现有化学杀线剂多为剧毒农药，有的杀线剂被发现有致畸、致癌等剧毒作用，其中一部分已从市场上淘汰（被撤销商标停用）或正在被重新审查，如溴甲烷；或因用量大，成本高，只能用于高价值的作物。因此，寻找新类型高效杀线剂迫在眉睫。
多肽类化合物一直以来都是活性药物研究的重要对象，在具有生物活性的天然产物、合成药物中广泛存在，生物体内也存在可与之结合的多样靶点。因此，本发明利用特定氨基酸序列合成新类型具杀线虫活性的环肽类化合物，不仅在有效药物的设计上具有重要指导意义，对于设计合成新类型杀线虫剂也具有先导价值。
发明内容
本发明提供了一种杀线虫环肽，所述环肽的氨基酸序列为cyclo(CKLPFLIPC)，其中两个Cys形成二硫键。该环肽的分子式为C49H78N10O10S2，分子量为1031.34，通过高效液相色谱法进行纯化后，其纯度可达到95%以上。
本发明公开了所述环肽的制备方法，本发明方法采用固相合成法来制备。所述固相合成法可通过以下措施达到：采用Fmoc保护策略，选取树脂作为载体，Trt（三苯甲基）作为半胱氨酸巯基保护基，将所述环肽的C端（羧基端）采用Fmoc-Cys(Trt)-OH以共价键形式连接到树脂上，洗涤然后脱掉Fmoc保护基，按照所述环肽氨基酸序列CKLPFLIPC的顺序，重复上述步骤进行偶联和脱Fmoc，每接完1个氨基酸以后，用试剂进行检测，显色反应为阴性则进入下一个偶联循环，否则重复偶联步骤。完成偶联后，切去树脂及将Trt脱保护后得多肽粗品，利用高效液相色谱法进一步纯化，再使两个Cys形成二硫键成环。最后再次利用高效液相色谱法纯化得到纯度大于95%的环肽产物。
本发明提供了所述环肽在杀线虫活性方面的应用。所述环肽在0.1-0.3 mg/ml浓度范围内，24小时后，对秀丽隐杆线虫致死率为3.67%-84.92%，其半数致死浓度LC50为0.27mg/mL。
与现有技术相比，本发明具有以下的优点和技术效果：本发明首次合成了该杀线虫环肽，并且测定了该环肽的杀线虫活性，所述环肽具有较好的杀线虫活性。
附图说明
图1 杀线虫环肽cyclo(CKLPFLIPC)的HPLC图。
图2 杀线虫环肽cyclo(CKLPFLIPC)的MS图。
图3 杀线虫环肽cyclo(CKLPFLIPC)不同浓度处理对秀丽隐杆线虫的效应：A为阴性对照；B~F为杀线虫环肽cyclo(CKLPFLIPC)不同浓度处理，分别为0.10、0.15、0.20、0.25和0.30 mg/mL。
实施例
本发明的具体实施方式结合以下实施例来说明，但本发明并不限于以下实施例。
1、杀线虫环肽的固相合成
在本发明所述的杀线虫环肽的固相合成过程中，采用Fmoc保护策略，称取树脂（1g，0.72 mmol/g）于25 ml 固相反应器中，用15 ml CH2Cl2 溶胀2 h。称取Fmoc-Cys(Trt)-OH（1.00 g，1.70 mmol）、HBTU（0.64 g ，1.70 mmol）、HOBT（0.23 g，1.70 mmol）溶于15 mlDMF中，加入DIEA（1.40 ml，8.50 mmol）活化后加入固相反应器中，在室温下摇床震荡反应3h。用10%哌嗪和含10%乙醇的DMF除去Fmoc保护基后，按照所述环肽氨基酸序列CKLPFLIPC的顺序，重复上述步骤进行偶联和脱Fmoc，每接完1个氨基酸以后，用Kaiser试剂检测，脯氨酸（Pro）用溴酚蓝法检测，显色反应为阴性则进入下一个偶联循环，否则重复偶联步骤。完成偶联后，称取多肽树脂放入反应瓶中，按照1 g树脂5 ml裂解剂的比例配置裂解液，用90%v/v三氟乙酸、5%v/v硫代茴香醚、3%v/v 1,2-乙二硫醇和2%v/v茴香醚的混合物裂解3 h后抽滤，滤液加入大量的冰乙醚中析出白色絮状沉淀，离心后真空干燥得到相应的粗肽。利用高效液相色谱法纯化后（C18色谱柱。高效液相条件：流动相A为水（含体积分数为 0.1%的TFA），B为水∶乙腈（1∶9，V/V，含体积分数为0.1%的TFA）；洗脱程序：0～30 min，10%B～85%B；流速为1 ml/min；柱温：35℃；检测波长230 nm），将其溶于50%乙醇/水（1 ml）中，缓慢滴加10 mmol/L的I2/乙醇（30 μl），搅拌5 min，HPLC监测原料峰消失（色谱条件同上），说明氧化成环完成。最后再次利用反相高效液相色谱法纯化，冻干得到纯度大于95%的环肽产物。
2、所述环肽杀线虫活性测定
对所述环肽采用浸虫法测定抑制秀丽隐杆线虫试验，其致死效应见表1。由表1可知，所述环肽在0.1-0.3 mg/ml浓度范围内，24小时后，对秀丽隐杆线虫致死率为3.67%-84.92%，其半数致死浓度LC50为0.27 mg/mL。
表1. 杀线虫环肽不同浓度处理对秀丽隐杆线虫的致死效应
Claims (3)
1.一种杀线虫环肽，其特征在于，所述环肽的氨基酸序列为cyclo(CKLPFLIPC)，其中两个Cys形成二硫键。
2.一种制备权利要求1中所述杀线虫环肽的方法，其特征在于，采用固相合成法来制备所述环肽。
3.权利要求1中所述杀线虫环肽制备杀秀丽隐杆线虫药物的应用。
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