CN116554184A - 一种新倍半萜生物碱化合物及其制备方法与应用 - Google Patents
一种新倍半萜生物碱化合物及其制备方法与应用 Download PDFInfo
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Abstract
本发明公开了一种新倍半萜生物碱化合物及其制备方法与应用。本发明公开的新倍半萜生物碱化合物对中药材仓储害虫赤拟谷盗具有显著拒食作用,可有效防治中药材仓储害虫。拒食实验结果显示:本发明新倍半萜生物碱来源丰富,制备工艺简单,生产成本低,其拒食活性与阳性对照川楝素相当,对中药材仓储害虫的拒食效果显著,有望开发成绿色生物拒食剂。
Description
本申请得到国家自然科学基金青年项目的支持,项目编号:82003887。
技术领域
本发明属于中药化学领域,特别是涉及一种新倍半萜生物碱及其制备方法,本发明还涉及所述化合物在中药材仓储害虫防治中的应用。
背景技术
近年来,中药资源产业链上游研究进展迅速,尤其是在中药资源调查、中药资源开发与保护、活性成分解析及其生物合成、中药材生态种植等方面取得了众多成果。然而,其下游研究,尤其是生产后加工和仓储管理方面研究薄弱,造成了中药资源的巨大浪费,据统计,70%以上的中药材在储存及流通过程中容易遭受虫害,每年造成的经济损失超过数十亿元。作为中药材储藏期的优势种群,赤拟谷盗对中药材的危害极大,严重影响药材质量。目前防治中药材仓储害虫的主要方法是化学熏蒸法,但由于该方法的长期使用已经在使用剂量及害虫耐药性上产生了恶性循环,使得中药材仓储害虫防治工作变得更加举步维艰。因此,开发一种高效、绿色、健康的防治中药材仓储害虫的化合物具有重要意义。
倍半萜生物碱是一类小分子化合物,可从雷公藤属、石斛属、花椒属等中分离得到,文献报道该类生物碱具有抗病毒、抗肿瘤、免疫调节、神经保护等多种生物活性。发明者对川陕花椒根皮的甲醇提取物进行化学成分研究,分离出如式Ⅰ所示的新倍半萜生物碱。经抗虫活性筛选首次发现该化合物对中药材仓储害虫赤拟谷盗具有显著的拒食活性。表明该新倍半萜生物碱进一步有可能开发成新型拒食药物。
本发明的有益效果与意义在于:本发明的倍半萜生物碱是从药用植物川陕花椒中得到,药食同源,种质资源丰富,具备环境友好的绿色条件,植物资源具备可持续性开发的特点,同时,对于从药用植物资源中发掘新药具有重要的实践和指导意义。
发明内容
本发明的目的在于提供一种新倍半萜生物碱在制备防治中药材仓储害虫中的用途。
本发明的另一目的在于提供一种新的倍半萜生物碱。
本发明的另一目的在于提供该倍半萜生物碱的制备方法。
为实现上述目的,本发明公开的技术内容如下:
一种新倍半萜生物碱化合物,具有式Ⅰ所示结构:
本发明进一步公开了倍半萜生物碱的制备方法,其特征在于按如下步骤进行:
(1)取川陕花椒新鲜根皮,粉碎后置于锥形瓶中,料液的重量/体积比1:10,加入甲醇,超声3次,30min/次,减压抽滤,合并滤液并减压浓缩至浸膏,制备甲醇提取物;
(2)取上述甲醇提取物139g,经正相硅胶柱层析,采用石油醚-乙酸乙酯梯度洗脱分段,并进行TLC检查,合并相同组分,回收溶剂,获得6个馏分段,采用石油醚-乙酸乙酯体积比40:1馏分段经正相硅胶柱层析分离,制备得到倍半萜生物碱。
本发明同时也公开了式Ⅰ倍半萜生物碱在制备用于中药材仓储害虫拒食方面的用途;所述的中药材仓储害虫拒食指的是对仓储害虫赤拟谷盗的拒食。实验结果显示:随着浓度的升高,新倍半萜生物碱对仓储害虫赤拟谷盗的拒食活性逐渐增强,呈剂量依赖性。其半数有效浓度为64.21ppm,与阳性对照效果相当,甚至低于阳性对照,拒食效果显著。
本发明更加详细的描述如下:
本发明提供新倍半萜生物碱化合物的制备方法,包括如下步骤:
(1)取川陕花椒新鲜根皮,粉碎后置于锥形瓶中,料液的重量/体积比1:10,加入甲醇,超声3次,30min/次,减压抽滤,合并滤液并减压浓缩至浸膏,制备甲醇提取物;
(2)取上述甲醇提取物139g,经正相硅胶柱层析,采用石油醚-乙酸乙酯(60:1、40:1、20:1、10:1、5:1、2:1、1:1)梯度洗脱分段,并进行TLC检查,合并相同组分,回收溶剂,获得6个馏分段,采用石油醚-乙酸乙酯体积比40:1馏分段经正相硅胶柱层析分离,制备得出半萜生物碱化合物。
本发明主要考察了一种新倍半萜生物碱及其的制备方法和其对中药材仓储害虫赤拟谷盗的拒食新用途。重点是发现该倍半萜生物碱为新化合物且对中药材仓储害虫具有显著拒食效果的新用途,发明的难点在于该倍半萜生物碱的丰富原料来源、制备工艺及显著拒食效果的发现。
本发明公开的新倍半萜生物碱的制备方法和防治中药材仓储害虫的效果与现有技术相比所具有的积极效果在于:
1、本发明新倍半萜生物碱来源丰富,制备工艺简单,生产成本低。
2、本发明新倍半萜生物碱对中药材仓储害虫赤拟谷盗具有显著拒食活性,可以应用在中药材仓储害虫的防治方面。有望开发成绿色生物拒食剂。
3、本发明新倍半萜生物碱具有高效、低成本、绿色安全的特性,有望开发成绿色拒食剂。
附图说明
图1:新倍半萜生物碱(式I)对赤拟谷盗拒食活性的半数有效浓度(EC50)。
具体实施方式
下面通过具体的实施方案叙述本发明。除非特别说明,本发明中所用的技术手段均为本领域技术人员所公知的方法。另外,实施方案应理解为说明性的,而非限制本发明的范围,本发明的实质和范围仅由权利要求书所限定。对于本领域技术人员而言,在不背离本发明实质和范围的前提下,对这些实施方案中的物料成分和用量进行的各种改变或改动也属于本发明的保护范围。本发明所用原料资源丰富可采集,所用试剂均有市售。
实施例1:甲醇提取物制备
取川陕花椒新鲜根皮,粉碎后置于锥形瓶中,料液比1:10加入甲醇,超声3次,30min/次,减压抽滤,合并滤液并减压浓缩至浸膏,制备甲醇提取物待用。
实施例2
新倍半萜生物碱(式I)
取川陕花椒根皮甲醇提取物139g,经正相硅胶柱层析,采用石油醚-乙酸乙酯梯度洗脱分段,并进行TLC检查,合并相同组分,回收溶剂,获得6个馏分段,石油醚-乙酸乙酯40:1)馏分段经正相硅胶柱层析分离,得到新倍半萜生物碱3.55g。
实施例3
新倍半萜生物碱(式I)结构鉴定
新倍半萜生物碱(式I),无色针状结晶,易溶于三氯甲烷,日光下喷改良的碘化铋钾显橙色斑点,判断该化合物为生物碱类化合物,HR-ESI-MS(m/z)谱中,分子离子峰552.3153[M+H]+获知该化合物的分子量为551.3036,核磁信息(1D-NMR,2D-NMR)如表1确定分子组成为C36H41NO4。
表1. 新倍半萜生物碱的核磁信息
实施例4
新倍半萜生物碱(式I)拒食活性
实验方法:使用万分之一分析天平精密称量样品约2 mg,加入适量无水乙醇配制母液(浓度为1 mg/mL),加纯净水定容至2 mL,分别稀释成终浓度为80、400、2000 ppm的溶液。称取0.4 g面粉加入到配液中,不断搅拌至形成均匀。空白对照用同等质量的面粉与2mL纯净水混匀。切去1000 μL移液枪枪头至形成直径为0.5 cm的枪头备用,每个浓度吸取200 μL,滴加在一次性洁净培养皿上,自然晾干形成面饼,每个浓度做6个面饼,然后将面饼放置在培养箱中平衡水分;选择20头羽化一周左右的成虫作为供试仓虫,放入玻璃瓶置于培养箱中,培养箱温度控制在29±1°C,相对湿度控制在75±5%,对试虫进行24 h饥饿处理。实验过程中,分别称量并记录空瓶的重量、加入面饼后瓶的重量及加入20头试虫后的总重量,置于培养箱中培养。3天后,依次称量总瓶重,去虫后瓶与面饼的重量,每个浓度设置5个平行实验,计算拒食率。公式如下:
C:对照组面饼消耗量(mg);T:处理组面饼消耗量(mg)。
通过IBM SPSS 20.0统计软件计算Concentration for 50% of Maximal Effect(EC50)。
实验结果:
拒食实验结果显示(见附图1,I为新倍半萜生物碱;Ctrl为阳性对照川楝素),本发明新倍半萜生物碱来源丰富,制备工艺简单,且对常见中药材仓储害虫赤拟谷盗具有显著的拒食效果,其拒食活性与阳性对照川楝素相当。
在详细说明的较佳实施例之后,熟悉该项技术人士可清楚地了解,在不脱离上述申请专利范围与精神下可进行各种变化与修改,凡依据本发明的技术实质对以上实施例所作任何简单修改、等同变化与修饰,均属于本发明技术方案的范围。且本发明亦不受说明书中所举实例实施方式的限制。
Claims (3)
1.一种新倍半萜生物碱化合物,具有式Ⅰ所示结构:
。
2.权利要求1所述倍半萜生物碱的制备方法,其特征在于按如下步骤进行:
(1)取川陕花椒新鲜根皮,粉碎后置于锥形瓶中,料液的重量/体积比1:10,加入甲醇,超声3次,30min/次,减压抽滤,合并滤液并减压浓缩至浸膏,制备甲醇提取物;
(2)取上述甲醇提取物139g,经正相硅胶柱层析,采用石油醚-乙酸乙酯分为60:1、40:1、20:1、10:1、5:1、2:1、1:1分段梯度洗脱,并进行TLC检查,合并相同组分,回收溶剂,获得6个馏分段,采用石油醚-乙酸乙酯体积比40:1馏分段经正相硅胶柱层析分离,制备倍半萜生物碱。
3.权利要求1所述式Ⅰ倍半萜生物碱在用于中药材仓储害虫拒食方面的用途;所述的中药材仓储害虫拒食指的是对仓储害虫赤拟谷盗的拒食。
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