杠柳和昆明山海棠根皮杀虫活性成分研究
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摘要
从天然存在的化合物中寻找农药活性化合物,筛选先导化合物,并以其为模板进行人工合成筛选,是新农药创制的主要途径之一。基于这一思路,对杠柳Periploca sepium Bunge和昆明山海棠Tripterygium hypoglaucum (Levl.) Hutch杀虫活性成分进行了较为系统的研究,主要研究结果如下:
1.从杠柳根皮中分离鉴定出12个杠柳新苷类化合物、4个低聚糖类化合物以及杠柳毒苷、β-香树脂乙酸酯、异香草醛等共19个化合物,其中杠柳新苷R、杠柳新苷P、杠柳新苷Q、杠柳新苷X及低聚糖NW为未见文献报道的新化合物。
2.生测结果表明杠柳新苷D、F、A、X对3龄粘虫表现为胃毒活性,48h后胃毒致死中浓(LC50)依次为0.39、0.34、4.10和0.11mg?mL-1。杠柳新苷R、Q、D、F、A、X、杠柳毒苷及低聚糖NW对小菜蛾具有胃毒活性,48h后其胃毒LC50依次为2.03、1.30、1.21、1.39、3.62、0.89,1.16和1.17mg?mL-1。症状观察表明:杠柳新苷类化合物可能主要作用于昆虫的消化系统。
3.采用电喷雾多级质谱技术对杠柳新苷A和E的裂解规律进行了研究,结果表明杠柳新苷类化合物甾体骨架与二取代吡喃酮的断裂产生丢失140Da的碎片,各糖苷键的断裂导致形成不同组成的糖链。从质谱图中可以通过准分子离子峰减去糖链以及吡喃酮单元间接证实骨架的存在,同时D环开裂重排失去甲醛(-30Da)也是一个重要的结构特征,可以作为识别该骨架的依据。
4.从昆明山海棠根皮中分离鉴定7个二氢沉香呋喃大环吡啶生物碱类化合物:雷公藤春碱,雷公藤吉碱,雷公藤定碱,雷公藤榕碱,雷公藤植碱,peritassines A和wilfordinine G,其中wilfordinine G是首次从昆明山海棠中分离得到。
5.生测结果表明:雷公藤春碱和雷公藤吉碱对粘虫胃毒麻醉中量(ND50)为18.10μg/头和7.40μg/头,雷公藤定碱和雷公藤榕碱对粘虫触杀ND50分别为0.33μg/头和0.06μg/头,对小地老虎胃毒ND50分别为5.66μg/头、3.91μg/头,对小菜蛾胃毒LD50分别为5.62μg/头和1.24μg/头。peritassines A,K7和wilfordinine G对粘虫触杀致死中量分别为0.069μg/头,0.030μg/头和0.039μg/头。症状观察表明雷公藤大环生物碱可能作用于昆虫的神经系统或/和肌肉系统。
An available pathway to develop new kinds of insecticides is to find novel lead compounds from plants. For this purpose, insecticidal components of Periploca sepium and Tripterygium hypoglaucum were studied in this paper.
1. The totale of 19 compounds were isolated by means of bioassay-guided chromatography from P. sepium .The structures of these compounds were determined by 1H-NMR, 13C-NMR,X-ray crystal diffraction and mass spectral analysis as Periplocoside R, P, Q, D, F, L, K, E, A, X, A′, 2-O -acetyl-β-D-dit-(1→4)-β- D-cym -(1→4)-β- D-cym-(1→4) -β-D-cym- (1→4)- L- oleandronic acid–δ-lactone, Oligosaccharide D2, Oligosaccharide F2, Periplogenin, Isovanillin,β-amyrin acetate, Glycoside H1 and Oligosaccharide NW, Five of them were new compounds: Periplocoside R, Periplocoside P, Periplocoside Q, Periplocoside X and Oligosaccharide NW.
2. Bioassay results showed that periplocoside D, F, A and X had only stomach toxic activity against the 3rd larvae of Mythimna separata. After administration 48h, the stomach medium lethal concentrations values (LC50) of these compounds were 0.39, 0.34, 4.10 and 0.11 mg·mL-1, respectively. Periplocoside R,Q, D, F, A,X, Periplogenin and Oligosaccharide NW had stomach toxicity against the 3rd instar larvae of Plutella xyllostella. After administration 48h, the LC50 of these compounds were 2.03, 1.30, 1.21, 1.39, 3.62, 0.89, 1.16 and 1.17 mg·mL-1, respectively. The toxic symptoms of M. separata showed that digestive system might be the target of periplocosides.
3 The pathway of fragment forming and cleavage of compound Periplocoside E and A were investigated by ESI MSn. A MS method used to identify Periplocosides in the process of screening new compounds was developed.
4. Eight insecticidal constituents of T. hypoglaucum were isolated by means of bioassay-guided chromatography. The structures of 7 compounds were determined by 1H-NMR, 13C-NMR , X-ray Crystal diffraction and mass spectral analysis as wilfortrine,wilforgine,wilfordine ,wilforine, wilfordsuine,peritassines A and wilfordinine G. wilfordinine G is first isolated from T. hypoglaucum.
5. Bioassay results showed wilfortrine and wilforgine had only stomach toxic activity against the 3rd larvae of M. separata , but wilfordine and wilforine had strong contact activity against the 4th larvae of M. separata and stomach activity against the 3rd larvae of Agrotls ypsilon. Medium narcosis dose (ND50) values of wilfordine and wilforine were 0.33μg·larvae-1 and 0.06μg·larvae-1 respectively against M. separata, and 5.66μg·larvae-1 and 1.24μg·larvae-1 respectivelly against A. ypsilon. ND50 values of wilfortrine and wilforgine were 18.10μg·larvae-1 and 7.40μg·larvae-1 respectivelly against M. separata.
Peritassines A, K7 and wilfordinine G had strong contact activity against the 4th larvae of M. separata and medium leathal dose (LD50) values of them were 0.069μg·larvae-1, 0.030μg·larvae-1 and 0.060μg·larvae-1 respectivelly against M. separata. The toxic symptoms of M. separata showed that nerve or/and muscle system might be the target of these dihydroagarofuran sesquiterpene pyridine alkaloids.
1.从杠柳根皮中分离鉴定出12个杠柳新苷类化合物、4个低聚糖类化合物以及杠柳毒苷、β-香树脂乙酸酯、异香草醛等共19个化合物,其中杠柳新苷R、杠柳新苷P、杠柳新苷Q、杠柳新苷X及低聚糖NW为未见文献报道的新化合物。
2.生测结果表明杠柳新苷D、F、A、X对3龄粘虫表现为胃毒活性,48h后胃毒致死中浓(LC50)依次为0.39、0.34、4.10和0.11mg?mL-1。杠柳新苷R、Q、D、F、A、X、杠柳毒苷及低聚糖NW对小菜蛾具有胃毒活性,48h后其胃毒LC50依次为2.03、1.30、1.21、1.39、3.62、0.89,1.16和1.17mg?mL-1。症状观察表明:杠柳新苷类化合物可能主要作用于昆虫的消化系统。
3.采用电喷雾多级质谱技术对杠柳新苷A和E的裂解规律进行了研究,结果表明杠柳新苷类化合物甾体骨架与二取代吡喃酮的断裂产生丢失140Da的碎片,各糖苷键的断裂导致形成不同组成的糖链。从质谱图中可以通过准分子离子峰减去糖链以及吡喃酮单元间接证实骨架的存在,同时D环开裂重排失去甲醛(-30Da)也是一个重要的结构特征,可以作为识别该骨架的依据。
4.从昆明山海棠根皮中分离鉴定7个二氢沉香呋喃大环吡啶生物碱类化合物:雷公藤春碱,雷公藤吉碱,雷公藤定碱,雷公藤榕碱,雷公藤植碱,peritassines A和wilfordinine G,其中wilfordinine G是首次从昆明山海棠中分离得到。
5.生测结果表明:雷公藤春碱和雷公藤吉碱对粘虫胃毒麻醉中量(ND50)为18.10μg/头和7.40μg/头,雷公藤定碱和雷公藤榕碱对粘虫触杀ND50分别为0.33μg/头和0.06μg/头,对小地老虎胃毒ND50分别为5.66μg/头、3.91μg/头,对小菜蛾胃毒LD50分别为5.62μg/头和1.24μg/头。peritassines A,K7和wilfordinine G对粘虫触杀致死中量分别为0.069μg/头,0.030μg/头和0.039μg/头。症状观察表明雷公藤大环生物碱可能作用于昆虫的神经系统或/和肌肉系统。
An available pathway to develop new kinds of insecticides is to find novel lead compounds from plants. For this purpose, insecticidal components of Periploca sepium and Tripterygium hypoglaucum were studied in this paper.
1. The totale of 19 compounds were isolated by means of bioassay-guided chromatography from P. sepium .The structures of these compounds were determined by 1H-NMR, 13C-NMR,X-ray crystal diffraction and mass spectral analysis as Periplocoside R, P, Q, D, F, L, K, E, A, X, A′, 2-O -acetyl-β-D-dit-(1→4)-β- D-cym -(1→4)-β- D-cym-(1→4) -β-D-cym- (1→4)- L- oleandronic acid–δ-lactone, Oligosaccharide D2, Oligosaccharide F2, Periplogenin, Isovanillin,β-amyrin acetate, Glycoside H1 and Oligosaccharide NW, Five of them were new compounds: Periplocoside R, Periplocoside P, Periplocoside Q, Periplocoside X and Oligosaccharide NW.
2. Bioassay results showed that periplocoside D, F, A and X had only stomach toxic activity against the 3rd larvae of Mythimna separata. After administration 48h, the stomach medium lethal concentrations values (LC50) of these compounds were 0.39, 0.34, 4.10 and 0.11 mg·mL-1, respectively. Periplocoside R,Q, D, F, A,X, Periplogenin and Oligosaccharide NW had stomach toxicity against the 3rd instar larvae of Plutella xyllostella. After administration 48h, the LC50 of these compounds were 2.03, 1.30, 1.21, 1.39, 3.62, 0.89, 1.16 and 1.17 mg·mL-1, respectively. The toxic symptoms of M. separata showed that digestive system might be the target of periplocosides.
3 The pathway of fragment forming and cleavage of compound Periplocoside E and A were investigated by ESI MSn. A MS method used to identify Periplocosides in the process of screening new compounds was developed.
4. Eight insecticidal constituents of T. hypoglaucum were isolated by means of bioassay-guided chromatography. The structures of 7 compounds were determined by 1H-NMR, 13C-NMR , X-ray Crystal diffraction and mass spectral analysis as wilfortrine,wilforgine,wilfordine ,wilforine, wilfordsuine,peritassines A and wilfordinine G. wilfordinine G is first isolated from T. hypoglaucum.
5. Bioassay results showed wilfortrine and wilforgine had only stomach toxic activity against the 3rd larvae of M. separata , but wilfordine and wilforine had strong contact activity against the 4th larvae of M. separata and stomach activity against the 3rd larvae of Agrotls ypsilon. Medium narcosis dose (ND50) values of wilfordine and wilforine were 0.33μg·larvae-1 and 0.06μg·larvae-1 respectively against M. separata, and 5.66μg·larvae-1 and 1.24μg·larvae-1 respectivelly against A. ypsilon. ND50 values of wilfortrine and wilforgine were 18.10μg·larvae-1 and 7.40μg·larvae-1 respectivelly against M. separata.
Peritassines A, K7 and wilfordinine G had strong contact activity against the 4th larvae of M. separata and medium leathal dose (LD50) values of them were 0.069μg·larvae-1, 0.030μg·larvae-1 and 0.060μg·larvae-1 respectivelly against M. separata. The toxic symptoms of M. separata showed that nerve or/and muscle system might be the target of these dihydroagarofuran sesquiterpene pyridine alkaloids.
引文
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