羌活提取物减轻乙草胺对水稻药害的作用研究
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摘要
乙草胺是一种活性高、价格低,应用非常广泛的除草剂,但是因为其易对水稻产生药害的原因而在稻田受到了限制。开发乙草胺的安全剂是解决药害扩大应用范围的一条有效途径。
中药材羌活(Rhizoma et Radix Notopterygii),为常用的中药之一。笔者所在的课题组曾对上百种植物材料进行筛选,发现羌活具有减轻乙草胺对水稻幼苗伤害的作用。本论文在前期研究的基础上采用索氏提取法提取羌活获得粗提物,先通过硅胶柱层析初步分离富集活性成分,经过活性追踪确定活性组分,然后用高速逆流色谱法(HSCCC)对确定的活性组分进行进一步的分离得到单体化合物,通过核磁共振等方法对单体化合物进行结构鉴定；确定其活性,初步研究其作用机理。主要研究结果如下：
1羌活粗提物解除乙草胺对水稻药害作用的效果
室内生测试验表明,水稻幼苗对乙草胺非常敏感,0.025mg/kg的乙草胺能够显著的抑制水稻幼苗的生长。在乙草胺质量浓度为0.025mg/kg条件下,当羌活提取物质量浓度为1.25、2.50、6.25和12.50mg/kg时,对水稻幼苗有较好的保护效果,株高分别为对照的78.5%、95.1%、96.6%、88.5%：株鲜重分别为对照的83.4%、98.6%、95.5%、96.9%；但是随着剂量进一步升高,羌活提取物对水稻的保护作用开始减弱。
室外盆栽试验表明,7.5g/hm2和15g/hm2的乙草胺对水稻株高和分蘖都有抑制作用,影响到水稻整个生育期；添加羌活提取物能明显的减轻乙草胺对水稻的伤害。3750g/hm2的羌活提取物和乙草胺的组合处理能使水稻的株高和分蘖数完全恢复到对照水平：不同处理间水稻剑叶长、剑叶宽和穗长均没有明显差别；羌活提取物和乙草胺的组合使用能明显减少产量的损失；单用羌活提取物的水稻与对照相比各生理指标没有显著差异。
2羌活主要功能成分的分离纯化
采用硅胶柱层析和高速逆流色谱相结合的方法分离纯化羌活提取物。粗提物先经硅胶柱层析分离,以石油醚和乙酸乙酯作为淋洗剂进行梯度洗脱,经点薄层板合并后共得到21个流分。组分Q5再经过HSCCC分离,以正己烷-醋酸乙酯-甲醇-水(5：5：4：5)为溶剂系统,上相为固定相,下相为流动相：结果经过HSCCC分离后,从300mg Q5样品中一次性分离得到三个组分Ⅰ(25.6mg),Ⅱ (36.1mg),Ⅲ(37.6mg)：经HPLC初步检测,组分Ⅰ为两种化合物的混合物,组分Ⅱ,Ⅲ为单体。
3活性成分的结构鉴定
经HPLC检测,发现两种单体化合物的纯度分别达到98.7%和99.1%,符合进一步鉴定的条件,经显色反应初步判定均为香豆素类化合物。经气-质及核磁共振氢谱、碳谱鉴定化合物的结构,确认化合物1和化合物2分别为异茴芹内酯(Isopimpinellin)和佛手柑内酯(Bergapten),分子量分别为246和216,两者结构相似,都属于呋喃香豆素类化合物。
4不同分离阶段组分的活性追踪试验
通过室内解毒生物测定对不同分离阶段羌活提取物进行了活性追踪,主要测定了硅胶柱层析分离物Q1～Q21,高速逆流色谱分离产物组分Ⅰ、Ⅱ、Ⅲ、和单体化合物Bergapten对水稻上乙草胺的解毒效果。
通过对硅胶柱层析获得的21个组分进行室内解毒生测试验,发现一个能明显缓解乙草胺对水稻药害作用的组分Q5,因此选择Q5作为进一步分离纯化的原材料。
经过HSCCC分离得到3个组分Ⅰ、Ⅱ、Ⅲ,将这3个组分进行室内解毒试验发现,当分离物的浓度为5mg/L时,组分Ⅰ、组分Ⅱ和组分Ⅲ对水稻上乙草胺均有一定的解毒效果,且以组分Ⅲ的解毒效果最佳。
单体化合物Bergapten对水稻上的乙草胺具有明显的解毒效果。在土壤基质,1.25-10mg/L的Bergapten与乙草胺混合处理的水稻幼苗株高与乙草胺对照相比均有显著差异,以5mg/L的Bergapten解毒效果较佳。进一步在琼脂基质中试验发现,0.1-5mg/L范围内的Bergapten对水稻上乙草胺均有一定的解毒作用,但是解毒效果随着安全剂的浓度降低而减弱。同时,通过室内生测试验表明,Bergapten对乙草胺的除草效果没有影响。
5羌活提取物减轻乙草胺对水稻药害的机理研究
羌活提取物能提高水稻GSTs活性,增强对除草剂的解毒能力。当羌活粗提物浓度在2.5～25mg/L的范围内时,水稻幼苗地上部分的GSTs活性能够被显著地诱导增强,并且随着浓度的升高而提高。与此对应的是,在此剂量范围内,羌活粗提物对乙草胺有较好的解毒效果。而从羌活中分离的单体化合物Bergapten,在其解毒剂量1.25～5mg/L范围内,也能够诱导水稻体内GSTs的活性显著增强。进一步通过离体试验证明,水稻GSTs能促进对乙草胺的降解作用。
The herbicide actochlor is commonly used all over the world because of its high activity and low cost, but it is limited in rice field because its phytotoxicity to rice. It is an effective way for sovling the phytotoxicity and expanding application areas of acetochlor to develop antidote of acetochlor.
The traditional Chinese medicine Rhizoma et Radix Notopterygii refers to the dried rhizome and root of Notopterygium incisum Ting ex H. T. Chang or N. forbesii Boiss or the mixture of both plants, which is one of the commonly used Chinese Herbal Medicine. Our research group found that the extract isolated from Rhizoma et Radix Notopterygii could reducing the phytotoxicity of acetochlor (2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide) to rice by screening97plant materials. Based on the previous study, the Rhizoma et Radix Notopterygii was extracted with ethanol in a Soxhlet extractor, the crude extract of Rhizoma et Radix Notopterygii was preliminarily separated by silica gel chromatography (CC) and the target compounds was enriched, the active constituent was fixed by bioassay-guided investigation, then high-speed count-current chromatography (HSCCC) was used to isolate and purify the monomeric compounds; the structure was identified and the acivity was determined; Finally, mechanism of action of active compounds as safeners was preliminarily studied. The main research results obtained are as follows:
1Protective effect of crude extract of Rhizoma et Radix Notopterygii to rice
Laboratory bioassay showed that rice seedlings grown under controlled environmental conditions were very sensitive to acetochlor, the growth of rice seedling was significantly inhibited by acetochlor at dose of0.025mg/kg. On the premise that the acetochlor dose was0.025mg/kg, crude extract at the dose of1.25,2.50,6.25, and12.5mg/kg showed preferable protection effect to rice, the shoot heights of rice seeding were78.5%,95.1%,96.6%,88.5%that of the control, respectively; and the plant fresh weight were83.4%,98.6%,95.5%,96.9%that of the control, respectively. However, the protection effect decreased as the dosage further increased.
Outdoor pot experiments verified that acetochlor at ratio of7.5g/hm or15g/hm2obviously inhibited the plant height and tiller number during entire period of rice growth. Crude extract of Rhizoma et Radix Notopterygii could obviously reduce the injury of acetochlor to rice. The plant height and tiller number of rice could totally recover by adding crude extract at a dose of3750g/hm2. There no significant difference between different treatments on the lenth of flag leaf, the width of flag leaf and the ear lenth of rice; the combination of crude extract and acetochlor could mitigate the loss of production of rice; Besides, the physiological indices had no significant difference between the application of crude extract alone and control.
2Separation and purification of active compounds from extract of Rhizoma et Radix Notopterygii
Column chromatography (CC) combined with high-speed count-current chromatography (HSCCC) were used to isolate and purify the extract of Rhizoma et Radix Notopterygii. The crude extract of Rhizoma et Radix Notopterygii was preliminarily separated by silica gel chromatography and and successively eluted with petroleum ether: ethyl acetate. Column fractions were analyzed by TLC and fractions with similar TLC patterns were pooled, twenty one fractions were obtained. Then the fraction Q5was further separated by HSCCC with two phase solvent systems composed of N-hexane-ethyl acetate-methanol-water (5:5:4:5). The upper phase was used as the stationary phase and the lower phase as the mobile phase. After separated by HSCCC, three compositions I (25.6mg),11(36.1mg) and Ⅲ(37.6mg) were obtained from300mg of the Q5sample. The purities determined by HPLC showed that fration I was a mixture of two compounds, fraction Ⅱ and Ⅲ were purity compounds.
3Identification of active compounds
The content was detected with HPLC method, results showed that the relative content of the compound1and compound2were99.1%and98.7, respectively; they are eligible to further identification. Color reaction preliminarily established them belong to coumarins. Their structures were further identified by1H-NMR,13C-NMR spectra and GC-MS. Finally, the compound1and compound2were established as Bergapten and Isopimpinellin, corresponding to the molecule weight of216and246, respectively. The two compounds have similar structures and both belong to furocoumarin.
4Activity tracing test of fraction from different saparation period
The detoxication activities of fractions on each isolation stage were analysized by laboratory bioassay. Twenty one fractions obtained by CC, three fractions obtained by HSCCC and the compound Bergapten were tested for their detoxication activities to acetochlor on rice.
Laboratory bioassay showed that the fraction Q5which was one of the twenty one fractions obtained by CC could significantly reduce the injury of acetochlor to rice, so the fraction Q5was selected for further isolation and purification.
The fraction Q5was applied to HSCCC and yield three fractions Ⅰ,Ⅱ, Ⅲ. Laboratory detoxication activity bioassay showed that all the three fractions had detoxication capacity to acetochlor on rice at the concentration of5mg/L, but fraction Ⅲ exhibited the best detoxication effect.
Bergapten could obviously reduce the injury of acetochlor to rice. In soil culture, the plant height of rice shoots treated with Bergapten in the range from1.25mg/L to10mg/L combined with acetochlor had significantly difference compared with acetochlor control; Bergapten at the concentration of5mg/L exhibited the best detoxication effect. In agar culture, the Bergapten concentration in the range from0.1mg/L to5mg/L all had protection effect to rice, but the detoxcation effect decreased with the reducing of the concentration. At the same time, laboratory bioassay showed that Bergapten had no influence on the effect of weed control of acetochlor.
5Study on mechanism of extract of Rhizoma et Radix Notopterygii protecting rice against acetochlor
Extract of Rhizoma et Radix Notopterygii could increase the ability for rice plants to detoxify acetochlor by raising GST activities. When the concentration of crude extract was ranging from2.5to25mg/L, GST activities in rice shoots were significantly increased with increasing concentration, positively correlated to the protection effect of rice shoots. When the concentration of Bergapten was ranging from1.25to5mg/L, GST activities in rice shoots were increased significantly too. Further study in vitro showed that the CSTs isolated form rice shoots could promote the degration of acetochlor.
中药材羌活(Rhizoma et Radix Notopterygii),为常用的中药之一。笔者所在的课题组曾对上百种植物材料进行筛选,发现羌活具有减轻乙草胺对水稻幼苗伤害的作用。本论文在前期研究的基础上采用索氏提取法提取羌活获得粗提物,先通过硅胶柱层析初步分离富集活性成分,经过活性追踪确定活性组分,然后用高速逆流色谱法(HSCCC)对确定的活性组分进行进一步的分离得到单体化合物,通过核磁共振等方法对单体化合物进行结构鉴定；确定其活性,初步研究其作用机理。主要研究结果如下：
1羌活粗提物解除乙草胺对水稻药害作用的效果
室内生测试验表明,水稻幼苗对乙草胺非常敏感,0.025mg/kg的乙草胺能够显著的抑制水稻幼苗的生长。在乙草胺质量浓度为0.025mg/kg条件下,当羌活提取物质量浓度为1.25、2.50、6.25和12.50mg/kg时,对水稻幼苗有较好的保护效果,株高分别为对照的78.5%、95.1%、96.6%、88.5%：株鲜重分别为对照的83.4%、98.6%、95.5%、96.9%；但是随着剂量进一步升高,羌活提取物对水稻的保护作用开始减弱。
室外盆栽试验表明,7.5g/hm2和15g/hm2的乙草胺对水稻株高和分蘖都有抑制作用,影响到水稻整个生育期；添加羌活提取物能明显的减轻乙草胺对水稻的伤害。3750g/hm2的羌活提取物和乙草胺的组合处理能使水稻的株高和分蘖数完全恢复到对照水平：不同处理间水稻剑叶长、剑叶宽和穗长均没有明显差别；羌活提取物和乙草胺的组合使用能明显减少产量的损失；单用羌活提取物的水稻与对照相比各生理指标没有显著差异。
2羌活主要功能成分的分离纯化
采用硅胶柱层析和高速逆流色谱相结合的方法分离纯化羌活提取物。粗提物先经硅胶柱层析分离,以石油醚和乙酸乙酯作为淋洗剂进行梯度洗脱,经点薄层板合并后共得到21个流分。组分Q5再经过HSCCC分离,以正己烷-醋酸乙酯-甲醇-水(5：5：4：5)为溶剂系统,上相为固定相,下相为流动相：结果经过HSCCC分离后,从300mg Q5样品中一次性分离得到三个组分Ⅰ(25.6mg),Ⅱ (36.1mg),Ⅲ(37.6mg)：经HPLC初步检测,组分Ⅰ为两种化合物的混合物,组分Ⅱ,Ⅲ为单体。
3活性成分的结构鉴定
经HPLC检测,发现两种单体化合物的纯度分别达到98.7%和99.1%,符合进一步鉴定的条件,经显色反应初步判定均为香豆素类化合物。经气-质及核磁共振氢谱、碳谱鉴定化合物的结构,确认化合物1和化合物2分别为异茴芹内酯(Isopimpinellin)和佛手柑内酯(Bergapten),分子量分别为246和216,两者结构相似,都属于呋喃香豆素类化合物。
4不同分离阶段组分的活性追踪试验
通过室内解毒生物测定对不同分离阶段羌活提取物进行了活性追踪,主要测定了硅胶柱层析分离物Q1～Q21,高速逆流色谱分离产物组分Ⅰ、Ⅱ、Ⅲ、和单体化合物Bergapten对水稻上乙草胺的解毒效果。
通过对硅胶柱层析获得的21个组分进行室内解毒生测试验,发现一个能明显缓解乙草胺对水稻药害作用的组分Q5,因此选择Q5作为进一步分离纯化的原材料。
经过HSCCC分离得到3个组分Ⅰ、Ⅱ、Ⅲ,将这3个组分进行室内解毒试验发现,当分离物的浓度为5mg/L时,组分Ⅰ、组分Ⅱ和组分Ⅲ对水稻上乙草胺均有一定的解毒效果,且以组分Ⅲ的解毒效果最佳。
单体化合物Bergapten对水稻上的乙草胺具有明显的解毒效果。在土壤基质,1.25-10mg/L的Bergapten与乙草胺混合处理的水稻幼苗株高与乙草胺对照相比均有显著差异,以5mg/L的Bergapten解毒效果较佳。进一步在琼脂基质中试验发现,0.1-5mg/L范围内的Bergapten对水稻上乙草胺均有一定的解毒作用,但是解毒效果随着安全剂的浓度降低而减弱。同时,通过室内生测试验表明,Bergapten对乙草胺的除草效果没有影响。
5羌活提取物减轻乙草胺对水稻药害的机理研究
羌活提取物能提高水稻GSTs活性,增强对除草剂的解毒能力。当羌活粗提物浓度在2.5～25mg/L的范围内时,水稻幼苗地上部分的GSTs活性能够被显著地诱导增强,并且随着浓度的升高而提高。与此对应的是,在此剂量范围内,羌活粗提物对乙草胺有较好的解毒效果。而从羌活中分离的单体化合物Bergapten,在其解毒剂量1.25～5mg/L范围内,也能够诱导水稻体内GSTs的活性显著增强。进一步通过离体试验证明,水稻GSTs能促进对乙草胺的降解作用。
The herbicide actochlor is commonly used all over the world because of its high activity and low cost, but it is limited in rice field because its phytotoxicity to rice. It is an effective way for sovling the phytotoxicity and expanding application areas of acetochlor to develop antidote of acetochlor.
The traditional Chinese medicine Rhizoma et Radix Notopterygii refers to the dried rhizome and root of Notopterygium incisum Ting ex H. T. Chang or N. forbesii Boiss or the mixture of both plants, which is one of the commonly used Chinese Herbal Medicine. Our research group found that the extract isolated from Rhizoma et Radix Notopterygii could reducing the phytotoxicity of acetochlor (2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methyl-phenyl)-acetamide) to rice by screening97plant materials. Based on the previous study, the Rhizoma et Radix Notopterygii was extracted with ethanol in a Soxhlet extractor, the crude extract of Rhizoma et Radix Notopterygii was preliminarily separated by silica gel chromatography (CC) and the target compounds was enriched, the active constituent was fixed by bioassay-guided investigation, then high-speed count-current chromatography (HSCCC) was used to isolate and purify the monomeric compounds; the structure was identified and the acivity was determined; Finally, mechanism of action of active compounds as safeners was preliminarily studied. The main research results obtained are as follows:
1Protective effect of crude extract of Rhizoma et Radix Notopterygii to rice
Laboratory bioassay showed that rice seedlings grown under controlled environmental conditions were very sensitive to acetochlor, the growth of rice seedling was significantly inhibited by acetochlor at dose of0.025mg/kg. On the premise that the acetochlor dose was0.025mg/kg, crude extract at the dose of1.25,2.50,6.25, and12.5mg/kg showed preferable protection effect to rice, the shoot heights of rice seeding were78.5%,95.1%,96.6%,88.5%that of the control, respectively; and the plant fresh weight were83.4%,98.6%,95.5%,96.9%that of the control, respectively. However, the protection effect decreased as the dosage further increased.
Outdoor pot experiments verified that acetochlor at ratio of7.5g/hm or15g/hm2obviously inhibited the plant height and tiller number during entire period of rice growth. Crude extract of Rhizoma et Radix Notopterygii could obviously reduce the injury of acetochlor to rice. The plant height and tiller number of rice could totally recover by adding crude extract at a dose of3750g/hm2. There no significant difference between different treatments on the lenth of flag leaf, the width of flag leaf and the ear lenth of rice; the combination of crude extract and acetochlor could mitigate the loss of production of rice; Besides, the physiological indices had no significant difference between the application of crude extract alone and control.
2Separation and purification of active compounds from extract of Rhizoma et Radix Notopterygii
Column chromatography (CC) combined with high-speed count-current chromatography (HSCCC) were used to isolate and purify the extract of Rhizoma et Radix Notopterygii. The crude extract of Rhizoma et Radix Notopterygii was preliminarily separated by silica gel chromatography and and successively eluted with petroleum ether: ethyl acetate. Column fractions were analyzed by TLC and fractions with similar TLC patterns were pooled, twenty one fractions were obtained. Then the fraction Q5was further separated by HSCCC with two phase solvent systems composed of N-hexane-ethyl acetate-methanol-water (5:5:4:5). The upper phase was used as the stationary phase and the lower phase as the mobile phase. After separated by HSCCC, three compositions I (25.6mg),11(36.1mg) and Ⅲ(37.6mg) were obtained from300mg of the Q5sample. The purities determined by HPLC showed that fration I was a mixture of two compounds, fraction Ⅱ and Ⅲ were purity compounds.
3Identification of active compounds
The content was detected with HPLC method, results showed that the relative content of the compound1and compound2were99.1%and98.7, respectively; they are eligible to further identification. Color reaction preliminarily established them belong to coumarins. Their structures were further identified by1H-NMR,13C-NMR spectra and GC-MS. Finally, the compound1and compound2were established as Bergapten and Isopimpinellin, corresponding to the molecule weight of216and246, respectively. The two compounds have similar structures and both belong to furocoumarin.
4Activity tracing test of fraction from different saparation period
The detoxication activities of fractions on each isolation stage were analysized by laboratory bioassay. Twenty one fractions obtained by CC, three fractions obtained by HSCCC and the compound Bergapten were tested for their detoxication activities to acetochlor on rice.
Laboratory bioassay showed that the fraction Q5which was one of the twenty one fractions obtained by CC could significantly reduce the injury of acetochlor to rice, so the fraction Q5was selected for further isolation and purification.
The fraction Q5was applied to HSCCC and yield three fractions Ⅰ,Ⅱ, Ⅲ. Laboratory detoxication activity bioassay showed that all the three fractions had detoxication capacity to acetochlor on rice at the concentration of5mg/L, but fraction Ⅲ exhibited the best detoxication effect.
Bergapten could obviously reduce the injury of acetochlor to rice. In soil culture, the plant height of rice shoots treated with Bergapten in the range from1.25mg/L to10mg/L combined with acetochlor had significantly difference compared with acetochlor control; Bergapten at the concentration of5mg/L exhibited the best detoxication effect. In agar culture, the Bergapten concentration in the range from0.1mg/L to5mg/L all had protection effect to rice, but the detoxcation effect decreased with the reducing of the concentration. At the same time, laboratory bioassay showed that Bergapten had no influence on the effect of weed control of acetochlor.
5Study on mechanism of extract of Rhizoma et Radix Notopterygii protecting rice against acetochlor
Extract of Rhizoma et Radix Notopterygii could increase the ability for rice plants to detoxify acetochlor by raising GST activities. When the concentration of crude extract was ranging from2.5to25mg/L, GST activities in rice shoots were significantly increased with increasing concentration, positively correlated to the protection effect of rice shoots. When the concentration of Bergapten was ranging from1.25to5mg/L, GST activities in rice shoots were increased significantly too. Further study in vitro showed that the CSTs isolated form rice shoots could promote the degration of acetochlor.
引文
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