川芎提取物解除精异丙甲草胺对水稻药害的研究
摘要
从植物中寻找具有生物活性的化合物,直接将其开发成为新农药,或者间接把这些活性物质当做先导化合物,进行结构修饰开发出生物活性更高的化合物,是目前农药研发的一条重要途径,也是新农药创制的研究热点。
伞形科植物川芎(Ligusticum chuanxiong)根茎是重要的传统中药,能够活血化瘀,治疗心血管、脑血管疾病、头痛和月经失调等疾病。本实验室经过多年的研究证实川芎具有解除酰胺类除草剂对水稻药害的作用,本论文在前人的研究基础上采用CO2超临界流体萃取法(CO2-SFE)提取川芎解除精异丙甲草胺对水稻药害的有效成分,通过高速逆流色谱法(HSCCC)一步分离获得活性成分,对其进行了结构鉴定和活性测定,并初步研究其作用机理。为活性成分的开发应用提供了必要的实验基础。获得的主要研究成果如下：
1川芎解除精异丙甲草胺对水稻药害的有效成分提取
CO2-SFE提取川芎活性成分,优化CO2-SFE萃取条件,优化条件为：萃取温度70℃、萃取压力35MPa、萃取时间2.5h和提取率4.45%。以Z-藁本内酯和洋川芎内酯A为指标,对川芎提取物进行质量控制,提取物中洋川芎内酯A和Z-藁本内酯的含量为17.85%和40.58%。
2川芎提取物室内和田间生物活性测定
室内生物测定表明提取物明显缓解精异丙甲草胺对水稻药害。提取物在琼脂培养基中能够完全恢复除草剂对水稻株高的抑制,对根长的恢复接近对照水平；在土壤基质培养中对株高的恢复接近对照水平。
提取物的田间试验表明60g/hm2和90g/hm2精异丙甲草胺对水稻有明显的抑制作用,影响水稻整个生育期。川芎提取物能够很好的缓解除草剂的伤害作用,对60g/hm2除草剂的伤害可以完全恢复到空白处理的水平；对90g/hm2除草剂的恢复作用下降；过量的提取物反而对水稻有伤害作用,影响对水稻的恢复作用；对照安全剂解草啶对水稻的解毒效果一般。测产结果证明240g/hm2提取物和60g/hm2除草剂组合处理的产量最高,空白处理因为受杂草的影响,产量减少。
稗草防效调查结果表明2个除草剂用量对禾本科杂草防效很好,低剂量除草剂的防效接近90%,高剂量除草剂的防效95%左右,2个时间点内稗草防效稳定。提取物和解草啶对除草剂的防效没有显著的影响。
3川芎提取物中生物活性成分的分离与鉴定
提取物四个主要成分对应的目标峰1-4的K值在溶剂体系正己烷-乙酸乙酯-乙醇-水[5：4：3：2(v/v)]中分别为0.18、0.50、2.01和3.40。经HSCCC分离获得四个主要成分,其中目标峰1和2经过HPLC或者GC-MS检测,纯度没有达到结构鉴定的要求,另外两个目标峰3和4经NMR鉴定确认为Z-藁本内酯和洋川芎内酯A,分子量分别为190和192。两者结构极为相似,只有C8和C9之间双键和单键之差,两者属于苯酞类化合物。
4室内生物活性测定
Z-藁本内酯明显缓解精异丙甲草胺对水稻药害。其在琼脂培养基中能够完全恢复除草剂对水稻株高的抑制,对根长的恢复接近对照水平；其在土壤基质培养中对株高的恢复接近对照水平。洋川芎内酯A在两种培养方式中对水稻的恢复作用一般。
5活性成分Z-藁本内酯解除精异丙甲草胺对水稻药害的机理研究
藁本内酯提高GST活性,增强植物对除草剂的解毒代谢能力,恢复除草剂对水稻的抑制作用。除草剂对水稻根和茎叶GST活性的影响与空白处理无明显差异,能够抑制水稻生长。Z-藁本内酯的解毒处理后,随着Z-藁本内酯浓度增大,根和茎叶的GST活性随之提高,水稻幼苗根和茎叶的恢复率也随之提高；当浓度为4mg/L,根和茎叶的GST活性分别是空白处理11倍和5倍左右,水稻幼苗的恢复率达到最大值；当浓度大于4mg/L,GST活性基本保持不变,此时对水稻幼苗恢复作用下降。
经Real-time PCR分析,水稻OsGSTU2基因的mRNA在空白处理、除草剂处理和除草剂与Z-藁本内酯组合处理中呈现差异表达。经除草剂和Z-藁本内酯组合处理,水稻OsGSTU2基因的mRNA表达量大于除草剂处理和清水处理。
Currently, it is an important way for development of pesticides that chemical compounds obtained from natural product are directly developed as new pesticides or structurally modified in an attempt to develop new compounds with higher activities.
L. chuanxiong belonged to Apiaceae is well-known in Traditional Chinese Medicine, which disperses blood stasis and is used extensively for the treatments of cardiovascular and cerebrovascular diseases, headache and menstrual disorders. It is also proved that L. chuanxiong could reverse the effect on rice caused by chloroacetamides in our lab. Hence, purpose of this paper was to obtain extract from L. chuanxiong by CO2-SFE and separate active compounds from the extract by HSCCC, which could protect rice from the injury of S-metolachlor. Finally, mode of action of active compounds as saferners was studied.
1Active extract from L. chuanxiong by CO2-SFE.
Extract was achieved to4.45%in extraction ratio by CO2-SFE under optimized condtions. The optimized process was to extract L. chuanxiong under temperature of70℃and pressure of35MPa for2.5h. Furthermore, the quality control of extract was conducted in terms of main active compounds Z-ligustilide and senkyunolide A, which were quantified by17.85%and40.58%respectively.
2Laboratory or field determination of activities of extract from L. chuanxiong.
In laboratory experiment, extract significantly protected rice from the damage of S-metolachlor. The level of Shoots height was totally recovered to that of the untreated and the level of roots length was close to that of the untreated after extract treatment in agar medium. Meanwhile, the level of shoots height was close to that of the untreated after extract treatment in soil-based medium.
The results of field experiments verified that S-metolachlor at ratio of60g/hm2or90g/hm2obviously inhibited the rice growth during entire period of rice growth. Extract could totally reverse the effect which caused by S-metolachlor at60g/hm2, with the reduced capability of reversing the effect on rice caused by S-metolachlor at90g/hm2. In contrast, overdose of extract could produce harm to rice. Results of the final rice yields verified that the highest rice yield was achieved after the detoxification of60g/hm2metolachlor by240g/hm2extact. and less achieved from the untreated due to the competitive growth of weeds.
Results demonstrated S-metolachlor effectively controlled barnyard grass with90%at60g/hm2and95%at90g/hm2in control efficacy. Extract and feclorim didn't significantly influenced barnyard grass control.
3Separation and identification of active compounds from extract
The targeted peaks1-4from extract was separated in a run of HSCCC by the appropriate solvent system which was n-hexane/ethyl acetate/ethanol/water [5:4:3:2(v/v)], corresponding to the K values of0.18,0.50,2.01and3.40separately. Among the compounds1-4, compounds1and2needed for further purification after analysis of HPLC and GC-MS. The other compounds3and4were identified as Z-ligustilide and senkyunolide A, corresponding to the molecule weight of190and192, respectively. The slight difference was found between C8and C9in bonding of compounds3and4which both belong to phthalide.
4Bioassay of separated compounds.
In laboratory experiment, protective effect on rice by Z-ligustilide was better than that by senkyunolide A. The level of shoots height was totally recovered to that of the untreated and the level of roots length was close to that of the untreated after Z-ligustilide treatment in agar medium. Meanwhile, the level of shoots height was close to that of the untreated after extract treatment in soil-based medium.
5Mode of action of Z-ligustilide protecting rice against S-metolachlor.
Z-ligustilide could enhance the ability for rice plants to detoxify S-metolachlor by increasing GST activities in plants, subsequently leading to reversion of effect on rice cause by S-metolachlor. GST activities in roots or shoots from S-metolachlor-treated rice seedlings presented no significant difference from the untreated control, while rice growth was severly inhibited by S-metolachlor. After detoxification of herbicide by Z-ligustilide ranging from1-4mg/L, GST activities of roots and shoots were increased, positively correlated to recoveries in roots and shoots. However, GST activities in roots or shoots maintained the highest level after detoxification treatment of more than4mg/L Z-ligustilide, on the contrary, recoveries in roots and shoots were reduced.
Further study was focused on mRNA of OsGSTU2in rice roots and shoots analyzed by Real-time PCR. Results showed that there were significant difference in expression level of OsGSTU2mRNA in roots and shoots between the untreated, the S-metolachlor-treated and combined treatment, suggesting expression level of OsGSTU2mRNA was positively correlated to GST activities.
伞形科植物川芎(Ligusticum chuanxiong)根茎是重要的传统中药,能够活血化瘀,治疗心血管、脑血管疾病、头痛和月经失调等疾病。本实验室经过多年的研究证实川芎具有解除酰胺类除草剂对水稻药害的作用,本论文在前人的研究基础上采用CO2超临界流体萃取法(CO2-SFE)提取川芎解除精异丙甲草胺对水稻药害的有效成分,通过高速逆流色谱法(HSCCC)一步分离获得活性成分,对其进行了结构鉴定和活性测定,并初步研究其作用机理。为活性成分的开发应用提供了必要的实验基础。获得的主要研究成果如下：
1川芎解除精异丙甲草胺对水稻药害的有效成分提取
CO2-SFE提取川芎活性成分,优化CO2-SFE萃取条件,优化条件为：萃取温度70℃、萃取压力35MPa、萃取时间2.5h和提取率4.45%。以Z-藁本内酯和洋川芎内酯A为指标,对川芎提取物进行质量控制,提取物中洋川芎内酯A和Z-藁本内酯的含量为17.85%和40.58%。
2川芎提取物室内和田间生物活性测定
室内生物测定表明提取物明显缓解精异丙甲草胺对水稻药害。提取物在琼脂培养基中能够完全恢复除草剂对水稻株高的抑制,对根长的恢复接近对照水平；在土壤基质培养中对株高的恢复接近对照水平。
提取物的田间试验表明60g/hm2和90g/hm2精异丙甲草胺对水稻有明显的抑制作用,影响水稻整个生育期。川芎提取物能够很好的缓解除草剂的伤害作用,对60g/hm2除草剂的伤害可以完全恢复到空白处理的水平；对90g/hm2除草剂的恢复作用下降；过量的提取物反而对水稻有伤害作用,影响对水稻的恢复作用；对照安全剂解草啶对水稻的解毒效果一般。测产结果证明240g/hm2提取物和60g/hm2除草剂组合处理的产量最高,空白处理因为受杂草的影响,产量减少。
稗草防效调查结果表明2个除草剂用量对禾本科杂草防效很好,低剂量除草剂的防效接近90%,高剂量除草剂的防效95%左右,2个时间点内稗草防效稳定。提取物和解草啶对除草剂的防效没有显著的影响。
3川芎提取物中生物活性成分的分离与鉴定
提取物四个主要成分对应的目标峰1-4的K值在溶剂体系正己烷-乙酸乙酯-乙醇-水[5：4：3：2(v/v)]中分别为0.18、0.50、2.01和3.40。经HSCCC分离获得四个主要成分,其中目标峰1和2经过HPLC或者GC-MS检测,纯度没有达到结构鉴定的要求,另外两个目标峰3和4经NMR鉴定确认为Z-藁本内酯和洋川芎内酯A,分子量分别为190和192。两者结构极为相似,只有C8和C9之间双键和单键之差,两者属于苯酞类化合物。
4室内生物活性测定
Z-藁本内酯明显缓解精异丙甲草胺对水稻药害。其在琼脂培养基中能够完全恢复除草剂对水稻株高的抑制,对根长的恢复接近对照水平；其在土壤基质培养中对株高的恢复接近对照水平。洋川芎内酯A在两种培养方式中对水稻的恢复作用一般。
5活性成分Z-藁本内酯解除精异丙甲草胺对水稻药害的机理研究
藁本内酯提高GST活性,增强植物对除草剂的解毒代谢能力,恢复除草剂对水稻的抑制作用。除草剂对水稻根和茎叶GST活性的影响与空白处理无明显差异,能够抑制水稻生长。Z-藁本内酯的解毒处理后,随着Z-藁本内酯浓度增大,根和茎叶的GST活性随之提高,水稻幼苗根和茎叶的恢复率也随之提高；当浓度为4mg/L,根和茎叶的GST活性分别是空白处理11倍和5倍左右,水稻幼苗的恢复率达到最大值；当浓度大于4mg/L,GST活性基本保持不变,此时对水稻幼苗恢复作用下降。
经Real-time PCR分析,水稻OsGSTU2基因的mRNA在空白处理、除草剂处理和除草剂与Z-藁本内酯组合处理中呈现差异表达。经除草剂和Z-藁本内酯组合处理,水稻OsGSTU2基因的mRNA表达量大于除草剂处理和清水处理。
Currently, it is an important way for development of pesticides that chemical compounds obtained from natural product are directly developed as new pesticides or structurally modified in an attempt to develop new compounds with higher activities.
L. chuanxiong belonged to Apiaceae is well-known in Traditional Chinese Medicine, which disperses blood stasis and is used extensively for the treatments of cardiovascular and cerebrovascular diseases, headache and menstrual disorders. It is also proved that L. chuanxiong could reverse the effect on rice caused by chloroacetamides in our lab. Hence, purpose of this paper was to obtain extract from L. chuanxiong by CO2-SFE and separate active compounds from the extract by HSCCC, which could protect rice from the injury of S-metolachlor. Finally, mode of action of active compounds as saferners was studied.
1Active extract from L. chuanxiong by CO2-SFE.
Extract was achieved to4.45%in extraction ratio by CO2-SFE under optimized condtions. The optimized process was to extract L. chuanxiong under temperature of70℃and pressure of35MPa for2.5h. Furthermore, the quality control of extract was conducted in terms of main active compounds Z-ligustilide and senkyunolide A, which were quantified by17.85%and40.58%respectively.
2Laboratory or field determination of activities of extract from L. chuanxiong.
In laboratory experiment, extract significantly protected rice from the damage of S-metolachlor. The level of Shoots height was totally recovered to that of the untreated and the level of roots length was close to that of the untreated after extract treatment in agar medium. Meanwhile, the level of shoots height was close to that of the untreated after extract treatment in soil-based medium.
The results of field experiments verified that S-metolachlor at ratio of60g/hm2or90g/hm2obviously inhibited the rice growth during entire period of rice growth. Extract could totally reverse the effect which caused by S-metolachlor at60g/hm2, with the reduced capability of reversing the effect on rice caused by S-metolachlor at90g/hm2. In contrast, overdose of extract could produce harm to rice. Results of the final rice yields verified that the highest rice yield was achieved after the detoxification of60g/hm2metolachlor by240g/hm2extact. and less achieved from the untreated due to the competitive growth of weeds.
Results demonstrated S-metolachlor effectively controlled barnyard grass with90%at60g/hm2and95%at90g/hm2in control efficacy. Extract and feclorim didn't significantly influenced barnyard grass control.
3Separation and identification of active compounds from extract
The targeted peaks1-4from extract was separated in a run of HSCCC by the appropriate solvent system which was n-hexane/ethyl acetate/ethanol/water [5:4:3:2(v/v)], corresponding to the K values of0.18,0.50,2.01and3.40separately. Among the compounds1-4, compounds1and2needed for further purification after analysis of HPLC and GC-MS. The other compounds3and4were identified as Z-ligustilide and senkyunolide A, corresponding to the molecule weight of190and192, respectively. The slight difference was found between C8and C9in bonding of compounds3and4which both belong to phthalide.
4Bioassay of separated compounds.
In laboratory experiment, protective effect on rice by Z-ligustilide was better than that by senkyunolide A. The level of shoots height was totally recovered to that of the untreated and the level of roots length was close to that of the untreated after Z-ligustilide treatment in agar medium. Meanwhile, the level of shoots height was close to that of the untreated after extract treatment in soil-based medium.
5Mode of action of Z-ligustilide protecting rice against S-metolachlor.
Z-ligustilide could enhance the ability for rice plants to detoxify S-metolachlor by increasing GST activities in plants, subsequently leading to reversion of effect on rice cause by S-metolachlor. GST activities in roots or shoots from S-metolachlor-treated rice seedlings presented no significant difference from the untreated control, while rice growth was severly inhibited by S-metolachlor. After detoxification of herbicide by Z-ligustilide ranging from1-4mg/L, GST activities of roots and shoots were increased, positively correlated to recoveries in roots and shoots. However, GST activities in roots or shoots maintained the highest level after detoxification treatment of more than4mg/L Z-ligustilide, on the contrary, recoveries in roots and shoots were reduced.
Further study was focused on mRNA of OsGSTU2in rice roots and shoots analyzed by Real-time PCR. Results showed that there were significant difference in expression level of OsGSTU2mRNA in roots and shoots between the untreated, the S-metolachlor-treated and combined treatment, suggesting expression level of OsGSTU2mRNA was positively correlated to GST activities.
引文
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