CN115918668B - 倍半萜内酯作抗烟草花叶病毒药物的应用及其制备方法 - Google Patents
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Abstract
本发明公开了一种倍半萜内酯作抗烟草花叶病毒药物的应用及其制备方法，所述倍半萜内酯应用于制备抗烟草花叶病毒产品。本发明在对薇甘菊进行综合治理的基础上，探索及应用相关的活性物质，将其变废为宝，变害为利，也是防控的一条重要途径。本发明首次发现薇甘菊中倍半萜类化合物具有抗TMV活性，丰富抗TMV化合物结构的多样性，研究成果进一步丰富了薇甘菊的生物活性谱，发掘了薇甘菊在植物源抗病毒药物方面的潜能。
Description
技术领域
本发明涉及农药技术领域，具体为一种倍半萜内酯作抗烟草花叶病毒药物的应用及其制备方法。
背景技术
植物病毒病是农业生产中常见的一种病害，被称为“植物癌症”。烟草花叶病毒(TMV)是最具代表性的植物病毒。该病毒寄主范围广泛，高发于茄科植物中，最容易危害烟草和番茄，并引起重大病害。TMV侵染植物后叶片呈花叶或坏死斑，造成植株畸形、矮化，甚至死亡，导致农作物大幅度减产,品质降低。植物源活性物质具有低毒、低成本、对环境友好等特点。
薇甘菊(MikaniamicranthaH.B.K)为菊科(Asteraceae)假泽兰属(Mikania)，作为一种外来入侵物种，其生长和传播蔓延速度极快，攀援能力强，通过缠绕、覆盖影响其他植物的光合作用，最终致使被其覆盖的植物死亡，对入侵地的农林业生产、生态环境和生物多样性造成严重的破坏，危害性极大。薇甘菊含有倍半萜、二萜、黄酮、酚酸、木脂素、甾体等丰富的化学成分，具有调节植物生长、抗菌、抗癌、抗炎、杀虫等作用。但是，迄今为止，未见有从薇甘菊中提取分离倍半萜类化合物抗烟草花叶病毒的报道。
发明内容
针对以上问题，本发明提供了一种倍半萜内酯作抗烟草花叶病毒药物的应用及其制备方法，本发明提供的倍半萜类化合物的抗烟草花叶病毒活性好，对烟草花叶病毒侵染寄主具有良好的保护作用，能抑制病毒在烤烟K326中增殖的作用。
根据本发明的目的，本发明提供一种倍半萜内酯作抗烟草花叶病毒药物的应用，所述倍半萜内酯应用于制备抗烟草花叶病毒产品。
进一步地，所述倍半萜内酯为从薇甘菊中提取分离的倍半萜内酯。
进一步地，所述倍半萜内酯的浓度为50μg/mL。
根据本发明的另一个目的，本发明提供一种倍半萜内酯的制备方法，包括如下步骤：
S1，薇甘菊地上部分干燥粉碎，甲醇回流提取三次，每次30L，每次3h，用旋转蒸发仪浓缩得到甲醇提取物；
S2，将所得甲醇提取物溶于水，依次用乙酸乙酯、正丁醇萃取，通过减压浓缩得到乙酸乙酯萃取物、正丁醇萃取物；
S3，乙酸乙酯萃取物经硅胶200～300目柱色谱分离，用石油醚-丙酮体系为洗脱剂进行梯度洗脱，经TLC检测，得到Fr1～Fr5共5个不同馏分；
S4，Fr4经MCI除色素后，经硅胶200-300目柱色谱分离，用三氯甲烷-丙酮200:1～1:1洗脱，分成7个亚部分，分别为Fr4-1～Fr4-7，其中Fr4-1经重结晶析出白色晶体，为化合物1，Fr4-4经液相色谱柱乙腈：水50:50分离纯化为白色针状结晶，为化合物2；正丁醇萃取物经大孔树脂，乙醇-水梯度洗脱，浓缩得到Fr1～Fr5共5个不同馏分，Fr3经正相硅胶200～300目柱层析后，Fr3-1用石油醚-乙酸乙酯15:1～1:1梯度洗脱，纯化得无色油状物，为化合物3。
进一步地，所述化合物的1的分子式为
所述化合物的2的分子式为
所述化合物的3的分子式为
本发明的有益效果是：
本发明在对薇甘菊进行综合治理的基础上，探索及应用相关的活性物质，将其变废为宝，变害为利，也是防控的一条重要途径。本发明首次发现薇甘菊中倍半萜类化合物具有抗TMV活性，丰富抗TMV化合物结构的多样性，研究成果进一步丰富了薇甘菊的生物活性谱，发掘了薇甘菊在植物源抗病毒药物方面的潜能。
附图说明
图1为本发明薇甘菊中的倍半萜内酯对TMV侵染的保护效应对照图；
图2为本发明薇甘菊中的倍半萜内酯间接ELISA法检测结果图。
具体实施方式
下面将结合本发明实施例，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例1
一种倍半萜内酯作抗烟草花叶病毒药物的应用，倍半萜类化合物的抗烟草花叶病毒活性好，对烟草花叶病毒侵染寄主具有良好的保护作用，能抑制病毒在烤烟K326中增殖的作用。
2、下列结构式所示的倍半萜内酯在制备抗烟草花叶病毒药物中的应用，
该倍半萜内酯为从薇甘菊中提取分离的倍半萜内酯。
该倍半萜内酯化合物由下述方法获得：薇甘菊地上部分(13.05kg)干燥粉碎，甲醇回流提取3次，每次30L，每次3h，用旋转蒸发仪浓缩得到甲醇提取物。将所得提取物溶于水，依次用乙酸乙酯、正丁醇萃取，通过减压浓缩得到乙酸乙酯萃取物、正丁醇萃取物。乙酸乙酯萃取物经硅胶(200～300目)柱色谱分离，用石油醚-丙酮(1:0～0:1)体系为洗脱剂进行梯度洗脱，经TLC检测，得到Fr1～Fr5共5个不同馏分。Fr4(26.59g)经MCI除色素后，经硅胶(200～300目)柱色谱分离，用三氯甲烷～丙酮(200:1～1:1)洗脱，分成7个亚部分，分别为Fr4-1～Fr4-7，其中Fr4-1经重结晶析出白色晶体，为化合物1(171.20mg)，Fr4-4经液相色谱柱乙腈：水(50:50)分离纯化为白色针状结晶，为化合物2(93.00mg)。正丁醇萃取物经大孔树脂，乙醇-水(0:95-95:0)梯度洗脱，浓缩得到Fr1～Fr5共5个不同馏分，Fr3(30.68g)经正相硅胶(200～300目)柱层析后，Fr3-1用石油醚-乙酸乙酯(15:1～1:1)梯度洗脱，纯化得无色油状物，为化合物3(7.80mg)。
该薇甘菊中的倍半萜内酯应用于抗烟草花叶病毒中。该倍半萜内酯应用于制备抗烟草花叶病毒产品中，其活性成分为薇甘菊中的倍半萜内酯。所述病毒为烟草花叶病毒。上述薇甘菊中的倍半萜内酯的浓度为50μg/mL。
实施例2甘菊中的倍半萜内酯抗烟草花叶病毒作用试验方法和结果：
1实验方法
采用活体半叶枯斑法测定。挑选健康长势一致的5～6叶期的心叶烟，株挑选叶龄和叶片大小相似的3片上部叶片，供试化合物用无菌水稀释为50μg/mL，每片叶子的一半均匀施药200μL作为处理，另一半用相同浓度的DMSO处理作为对照，6h后每片叶子摩擦接种TMV200μL。接种10min后用蒸馏水将金刚砂洗净，将烟苗放在无虫温室中培养，3～4d后待枯斑症状明显时，统计试验结果，并按公式“抑制率(％)＝[(对照平均枯斑数-处理平均枯斑数)/对照平均枯斑数]×100％”计算抑制率。
2实验结果
先施药结果表明(表1、图1)，图1薇甘菊中的倍半萜内酯对TMV侵染的保护效应，左半叶为处理，右半叶为对照。
图2薇甘菊中的倍半萜内酯间接ELISA法检测结果，为接种TMV后5d普通烟叶圆片中烟草花叶病毒蛋白衣壳的累积情况。
在浓度为50μg/mL时，化合物1具有显著的烟草花叶病毒抑制作用，抑制率高达61.87％，显著高于阳性对照药宁南霉素，对TMV的半数抑制浓度(IC50)为33.80μg/mL；化合物3抗TMV活性与宁南霉素相当，IC50为45.76μg/mL；表明薇甘菊中的倍半萜内酯能诱导烟草获得植物系统抗性抵御病毒侵染。
表1薇甘菊中的倍半萜内酯对TMV侵染的保护作用
实施例3
薇甘菊中的倍半萜内酯抑制病毒增殖活性测定方法和结果：
1实验方法
采用叶圆片法测定。挑选健康长势一致的普通烟，喷施50μg/mL的化合物作为处理；喷施50μL/mLDMSO溶液作为对照；喷施宁南霉素的为阳性对照药。施药24h后每株烟挑选1片中上部叶片且摩擦接种TMV，10min后将金刚砂洗净，放无虫温室培养，接种TMV后5d打直径为1cm的圆片，每片叶片取10个圆片放于离心管，保存在-70℃冰箱，每个处理重复3次，用ELISA法测定OD405值，以喷施50μL/mLDMSO溶液，接种TMV的烟苗作为对照、不接种TMV的烟苗作为阴性对照，其中以处理OD405值/阴性对照OD405值＞2.1作为阳性判断的标准。
2实验结果
采用普通烟叶圆片法结合间接ELISA法检测了薇甘菊中的倍半萜内酯处理后普通烟叶圆片中烟草花叶病毒蛋白衣壳的累积情况。由图2可知，图2薇甘菊中的倍半萜内酯间接ELISA法检测结果，为接种TMV后5d普通烟叶圆片中烟草花叶病毒蛋白衣壳的累积情况。处理OD405值/阴性对照OD405值均小于2.1，即薇甘菊中的倍半萜内酯的间接ELISA检测结果均表现为阴性，说明薇甘菊中的倍半萜内酯均具有抑制TMV增殖的活性。其中，化合物2和化合物3抑制TMV增殖的活性相当于阳性药剂宁南霉素，能抑制TMV在烤烟K326中增殖。
本发明提供薇甘菊(MikaniamicranthaH.B.K)中的倍半萜内酯在制备抗烟草花叶病毒药物中的应用。试验结果证明，此类化合物能诱导烟草获得植物系统抗性抵御病毒侵染，显著抑制TMV对寄主的初侵染，从而减少病毒进入寄主细胞并进一步复制和增殖的机会，起到对寄主保护的作用；对TMV侵染的抑制率优于或相当于市售抗病毒农药宁南霉素，且其作用于TMV外壳蛋白，进而起到抑制病毒在烤烟K326中增殖的作用。
最后应说明的是：以上各实施例仅用以说明本发明的技术方案，而非对其限制；尽管参照前述各实施例对本发明进行了详细的说明，本领域的普通技术人员应当理解：其依然可以对前述各实施例所记载的技术方案进行修改，或者对其中部分或者全部技术特征进行等同替换；而这些修改或者替换，并不使相应技术方案的本质脱离本发明各实施例技术方案的范围。
Claims (1)
1.倍半萜内酯作抗烟草花叶病毒药物的应用，其特征在于，所述倍半萜内酯应用于制备抗烟草花叶病毒产品；所述倍半萜内酯为从薇甘菊中提取分离的倍半萜内酯；所述倍半萜内酯的浓度为50μg/mL；
所述倍半萜内酯的分子式为：
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