植物源病毒抑制剂VFB活性成分研究及抗TMV植物样品筛选
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摘要
从植物中寻找抗病毒活性物质是目前植物病毒抑制剂创制和开发的重要方向。为了给新型植物源病毒抑制剂的开发提供线索和理论依据，本论文主要进行了以下三个方面的研究：一是采用现代分离技术，结合活性跟踪对植物源病毒抑制剂VFB中活性成分进行了分离、纯化和结构鉴定；二是采用半叶枯斑法、整株法和漂浮叶圆片法较为系统的评价了我国西北地区74科214种313个植物样品乙醇提取物的抗TMV活性；三是以筛选出的植物样品为材料，初步研究了其对VFB水剂抗病毒活性的增效作用，得出了以下主要研究结果：
1．采用活性跟踪法从VFB中分离得到了15个化合物，最终鉴定出其中12个化合物的化学结构，分别为：3,4,5-三羟基-苯甲酸甲酯（Methyl gallate）、β-谷甾醇（β-Sitosterol）、7-甲基香豆素（7-methoxycoumarin）、β-香树酯醇（β-Amyrin）、大黄素（Emodin）、甘草素（Liquiritigenin）、熊果酸（Ursolic Acid）、牛蒡子苷（Arctiin）、4-[（2S,3R,4S）-4-[（S）-（3,4-二甲氧苯基）羟甲基]四氢-3-（羟甲基）-2-呋喃基]-2-甲氧苯基（4-[（2S,3R,4S）-4-[（S）-（3,4-dimethoxyphenyl）hydroxymethyl]tetrahydro-3-（hydroxymethyl）-2-furanyl]-2-methoxyphenyl）、槲皮素（Quercetin）、5-(3′,4′-二甲氧基苯基)-3-（β-（3′,4′-二甲氧基苯基）-α-羟基）-2H呋喃-4-羟基-4甲基-β-D-吡喃葡萄糖苷（5-(3′,4′-dimethoxyphenyl)-3-（β-（3′,4′-dimethoxyphenyl）-α-hydroxy）-2Hfuran-4-hydroxy-4methyl--β-D-glucopyranoside）和2-羰基-3-(3′,4′-二羟苯乙基)-5H-呋喃-4-（4′-对甲氧基苯乙基-3′-O-α-L-吡喃鼠李糖基(1-2)-β-D-吡喃葡萄糖苷（2-oxo-3-(3',4'-dihydroxyphenylethyl)-5H-furan-4-（4'-p-methoxyphenylethyl-3'-O-α-L-rhamnylpyranylo-syl (1-2)-β-D-glucopyranoside），其余3个化合物的化学结构有待进一步鉴定。
2．采用半叶枯斑法和漂浮叶圆片法系统的研究了15个化合物对TMV的抑制活性，结果表明，在1mg/mL的剂量下，甘草素和熊果酸在不同寄主上对TMV病毒粒体均有很好的抑制活性，甘草素和熊果酸既能强烈的体外钝化TMV病毒粒子，其钝化效果分别为54.20%和41.00%；又能较好的预防TMV对寄主的侵染，其抑制率分别为48.52%和45.73%；且对TMV在普通烟植株内的增殖有一定的抑制作用，其抑制率均在33.00%以上，故推断甘草素和熊果酸可能为植物源病毒抑制剂VFB中主要抗病毒活性物质。
3．采用半叶枯斑法测试了313个供试植物样品95%乙醇提取物对TMV病毒粒体的体外抑制作用，发现有27个科48种54个植物粗提物对TMV具有良好的体外钝化活性，其抑制率均在50%以上。在此基础上，采用整株法和漂浮叶圆片法进一步测定了这54个样品对TMV预防和增殖的抑制活性，其中仅有宽果红景天、糯米条、粗榧、牛心朴子草、臭椿和雷丸等6种样品能有效的抑制TMV的侵染和增殖，其抑制率均在50%以上。综合分析认为，宽果红景天、糯米条、粗榧、牛心朴子草、臭椿和雷丸6种样品的抗TMV作用显著，其抗植物病毒活性值得进一步研究。
4．初步研究了宽果红景天、糯米条、粗榧、牛心朴子草、臭椿和雷丸6种植物提取物对VFB水剂抗病毒活性的增效作用，结果表明雷丸提取物对VFB水剂表现出明显的增效作用。
植物中具抗植物病毒活性的物质含量丰富、种类繁多，其结构独特，且相互之间存在着极其复杂的互作关系。因此，植物界是发现低毒、低残留、高效及环境和谐的新抗病毒剂和新抗病毒化合物的最好的自然资源宝库。本试验研究结果对我国植物资源的合理开发利用及开发自主知识产权的农药都具有一定的理论意义和应用价值。
Direct selection of anti-viral compounds from plants is an important approach in novelantiviral agents development. To provide new materials and theoretical basis for exploitationof antiviral agents from plant resource, this research has been conducted mainly on thefollowing three aspects: the active ingredients were isolated from the botanical antiviral agentVFB by bioassay-guided fractionation modern separation technology, and identifiedpredominantly on the basis of nuclear magnetic resonance(NMR) data; the ethanol extracts of313plants（belonging to214plant species of74families）growing in the northwestern Chinawere evaluated by local lesion and leaf-disc methods to see whether the plants are with orwithout anti-TMV activity; Extracts of the plants screened out were used as experimentalmaterial for preliminary study of the synergistic effect to VFB. The main results andconclusions are shown as follows:
1.15compounds were isolated from the botanical antiviral agent VFB based onbioassay-guided fractionation, and the chemical structures of12compounds were identifiedby comparison of their MS and NMR data with those reported in the literature. Thosechemicals include Methyl gallate, β-Sitosterol,7-methoxycoumarin, β-Amyrin, Emodin,Liquiritigenin, Ursolic Acid, Arctiin,4-[(2S,3R,4S)-4-[(S)-(3,4-dimethoxyphenyl)hydroxymethyl]tetrahydro-3-(hydroxymethyl)-2-furanyl]-2-methoxyphenyl, Quercetin,5-(3′,4′-dimethoxyphenyl)-3-(β-(3′,4′-dimethoxyphenyl)-α-hydroxyl)-2Hfuran-4-hydroxy-4methyl-β-D-glucopyranoside and2-oxo-3-(3',4'-dihydroxyphenylethyl)-5H-furan-4-(4'-p-methoxyphenylethyl-3'-O-α-L-rhamnylpyranylosyl (1-2)-β-D-glucopyranoside. Chemicalstructures of the remaining3compounds needed further confirmation.
2. The anti-tobacco mosaic virus (TMV) activity of15compounds was tested by locallesion and leaf-disc methods, and the results indicated that the glycyrrhizin and ursolic acidshowed a significant inhibitory activity against TMV on different host species at aconcentration of1mg/mL. Those two compounds could strongly inactivate TMV in vitro, andthe inhibition rate of necrotic local lesions could reach54.20%and41.00%, respectively; theyalso had a good preventive effect on TMV infection to N. glutinosa, and the preventive effect rates were48.52%and45.73%, respectively; and they also showed certain activities ininhibiting multiplication of the TMV with inhibition rates of more than33.00%. It can beconcluded that the glycyrrhizin and ursolic acid were main antiviral compounds of VFB.
3. The anti tobacco mosaic virus (TMV) activity of95%ethanol extracts from313plantswere screened by the half-leaf method.54plant samples belonging to48plant species of27families showed a significant inhibitory activity against TMV in vitro, with inhibition rates ofmore than50%. Based on the result, the activity of54plant extract on infection andreplication was further determined by the whole-leaf and leaf-disc methods. Among them,extracts from six species [Rhodiola eurycarpa (Frod.) S. H. Fu, Abelia chinensis R. Br.,Cephalotaxus sinensis (Rehder et E. H. Wilson) H. L. Li, Cynanchum komarovii Al.,Ailanthus altissima (Mill.) Swingle and Polyporus mylittae Cook.et Mass] predominantlyinhibited both infection and viral replication with inhibition rates of over50%, which neededto be further studied.
4. In terms of synergistic effect to VFB, the preliminary study of six plants′extracts[Rhodiola eurycarpa (Frod.) S. H. Fu, Abelia chinensis R. Br., Cephalotaxus sinensis (Rehderet E. H. Wilson) H. L. Li, Cynanchum komarovii Al., Ailanthus altissima (Mill.) Swingle andPolyporus mylittae Cook.et Mass] indicated that extract of Polyporus mylittae Cook.et Massshowed an significant synergistic activity to VFB.
Abundant plants having anti-viral activity widely exist in nature. The types of secondarymetabolism products produced by those plants are plentiful and the structures of theseproducts are usually unique. Furthermore, complicated interactions between different plantshave been found through researches. Therefore, plants are the best natural resources to findnew and environmentally friendly anti-viral agents and compounds with low toxicity, lowresidue and high efficiency. It has both practical and theoretical significance in the rationaldevelopment and utilization of natural plant resources in China, as well as in the developmentof independent intellectual property rights of pesticides.
1．采用活性跟踪法从VFB中分离得到了15个化合物，最终鉴定出其中12个化合物的化学结构，分别为：3,4,5-三羟基-苯甲酸甲酯（Methyl gallate）、β-谷甾醇（β-Sitosterol）、7-甲基香豆素（7-methoxycoumarin）、β-香树酯醇（β-Amyrin）、大黄素（Emodin）、甘草素（Liquiritigenin）、熊果酸（Ursolic Acid）、牛蒡子苷（Arctiin）、4-[（2S,3R,4S）-4-[（S）-（3,4-二甲氧苯基）羟甲基]四氢-3-（羟甲基）-2-呋喃基]-2-甲氧苯基（4-[（2S,3R,4S）-4-[（S）-（3,4-dimethoxyphenyl）hydroxymethyl]tetrahydro-3-（hydroxymethyl）-2-furanyl]-2-methoxyphenyl）、槲皮素（Quercetin）、5-(3′,4′-二甲氧基苯基)-3-（β-（3′,4′-二甲氧基苯基）-α-羟基）-2H呋喃-4-羟基-4甲基-β-D-吡喃葡萄糖苷（5-(3′,4′-dimethoxyphenyl)-3-（β-（3′,4′-dimethoxyphenyl）-α-hydroxy）-2Hfuran-4-hydroxy-4methyl--β-D-glucopyranoside）和2-羰基-3-(3′,4′-二羟苯乙基)-5H-呋喃-4-（4′-对甲氧基苯乙基-3′-O-α-L-吡喃鼠李糖基(1-2)-β-D-吡喃葡萄糖苷（2-oxo-3-(3',4'-dihydroxyphenylethyl)-5H-furan-4-（4'-p-methoxyphenylethyl-3'-O-α-L-rhamnylpyranylo-syl (1-2)-β-D-glucopyranoside），其余3个化合物的化学结构有待进一步鉴定。
2．采用半叶枯斑法和漂浮叶圆片法系统的研究了15个化合物对TMV的抑制活性，结果表明，在1mg/mL的剂量下，甘草素和熊果酸在不同寄主上对TMV病毒粒体均有很好的抑制活性，甘草素和熊果酸既能强烈的体外钝化TMV病毒粒子，其钝化效果分别为54.20%和41.00%；又能较好的预防TMV对寄主的侵染，其抑制率分别为48.52%和45.73%；且对TMV在普通烟植株内的增殖有一定的抑制作用，其抑制率均在33.00%以上，故推断甘草素和熊果酸可能为植物源病毒抑制剂VFB中主要抗病毒活性物质。
3．采用半叶枯斑法测试了313个供试植物样品95%乙醇提取物对TMV病毒粒体的体外抑制作用，发现有27个科48种54个植物粗提物对TMV具有良好的体外钝化活性，其抑制率均在50%以上。在此基础上，采用整株法和漂浮叶圆片法进一步测定了这54个样品对TMV预防和增殖的抑制活性，其中仅有宽果红景天、糯米条、粗榧、牛心朴子草、臭椿和雷丸等6种样品能有效的抑制TMV的侵染和增殖，其抑制率均在50%以上。综合分析认为，宽果红景天、糯米条、粗榧、牛心朴子草、臭椿和雷丸6种样品的抗TMV作用显著，其抗植物病毒活性值得进一步研究。
4．初步研究了宽果红景天、糯米条、粗榧、牛心朴子草、臭椿和雷丸6种植物提取物对VFB水剂抗病毒活性的增效作用，结果表明雷丸提取物对VFB水剂表现出明显的增效作用。
植物中具抗植物病毒活性的物质含量丰富、种类繁多，其结构独特，且相互之间存在着极其复杂的互作关系。因此，植物界是发现低毒、低残留、高效及环境和谐的新抗病毒剂和新抗病毒化合物的最好的自然资源宝库。本试验研究结果对我国植物资源的合理开发利用及开发自主知识产权的农药都具有一定的理论意义和应用价值。
Direct selection of anti-viral compounds from plants is an important approach in novelantiviral agents development. To provide new materials and theoretical basis for exploitationof antiviral agents from plant resource, this research has been conducted mainly on thefollowing three aspects: the active ingredients were isolated from the botanical antiviral agentVFB by bioassay-guided fractionation modern separation technology, and identifiedpredominantly on the basis of nuclear magnetic resonance(NMR) data; the ethanol extracts of313plants（belonging to214plant species of74families）growing in the northwestern Chinawere evaluated by local lesion and leaf-disc methods to see whether the plants are with orwithout anti-TMV activity; Extracts of the plants screened out were used as experimentalmaterial for preliminary study of the synergistic effect to VFB. The main results andconclusions are shown as follows:
1.15compounds were isolated from the botanical antiviral agent VFB based onbioassay-guided fractionation, and the chemical structures of12compounds were identifiedby comparison of their MS and NMR data with those reported in the literature. Thosechemicals include Methyl gallate, β-Sitosterol,7-methoxycoumarin, β-Amyrin, Emodin,Liquiritigenin, Ursolic Acid, Arctiin,4-[(2S,3R,4S)-4-[(S)-(3,4-dimethoxyphenyl)hydroxymethyl]tetrahydro-3-(hydroxymethyl)-2-furanyl]-2-methoxyphenyl, Quercetin,5-(3′,4′-dimethoxyphenyl)-3-(β-(3′,4′-dimethoxyphenyl)-α-hydroxyl)-2Hfuran-4-hydroxy-4methyl-β-D-glucopyranoside and2-oxo-3-(3',4'-dihydroxyphenylethyl)-5H-furan-4-(4'-p-methoxyphenylethyl-3'-O-α-L-rhamnylpyranylosyl (1-2)-β-D-glucopyranoside. Chemicalstructures of the remaining3compounds needed further confirmation.
2. The anti-tobacco mosaic virus (TMV) activity of15compounds was tested by locallesion and leaf-disc methods, and the results indicated that the glycyrrhizin and ursolic acidshowed a significant inhibitory activity against TMV on different host species at aconcentration of1mg/mL. Those two compounds could strongly inactivate TMV in vitro, andthe inhibition rate of necrotic local lesions could reach54.20%and41.00%, respectively; theyalso had a good preventive effect on TMV infection to N. glutinosa, and the preventive effect rates were48.52%and45.73%, respectively; and they also showed certain activities ininhibiting multiplication of the TMV with inhibition rates of more than33.00%. It can beconcluded that the glycyrrhizin and ursolic acid were main antiviral compounds of VFB.
3. The anti tobacco mosaic virus (TMV) activity of95%ethanol extracts from313plantswere screened by the half-leaf method.54plant samples belonging to48plant species of27families showed a significant inhibitory activity against TMV in vitro, with inhibition rates ofmore than50%. Based on the result, the activity of54plant extract on infection andreplication was further determined by the whole-leaf and leaf-disc methods. Among them,extracts from six species [Rhodiola eurycarpa (Frod.) S. H. Fu, Abelia chinensis R. Br.,Cephalotaxus sinensis (Rehder et E. H. Wilson) H. L. Li, Cynanchum komarovii Al.,Ailanthus altissima (Mill.) Swingle and Polyporus mylittae Cook.et Mass] predominantlyinhibited both infection and viral replication with inhibition rates of over50%, which neededto be further studied.
4. In terms of synergistic effect to VFB, the preliminary study of six plants′extracts[Rhodiola eurycarpa (Frod.) S. H. Fu, Abelia chinensis R. Br., Cephalotaxus sinensis (Rehderet E. H. Wilson) H. L. Li, Cynanchum komarovii Al., Ailanthus altissima (Mill.) Swingle andPolyporus mylittae Cook.et Mass] indicated that extract of Polyporus mylittae Cook.et Massshowed an significant synergistic activity to VFB.
Abundant plants having anti-viral activity widely exist in nature. The types of secondarymetabolism products produced by those plants are plentiful and the structures of theseproducts are usually unique. Furthermore, complicated interactions between different plantshave been found through researches. Therefore, plants are the best natural resources to findnew and environmentally friendly anti-viral agents and compounds with low toxicity, lowresidue and high efficiency. It has both practical and theoretical significance in the rationaldevelopment and utilization of natural plant resources in China, as well as in the developmentof independent intellectual property rights of pesticides.
引文
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