CN101215278B - 抗植物真菌活性补骨脂二氢黄酮 - Google Patents
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Abstract
抗植物真菌活性补骨脂二氢黄酮，涉及一种化合物，特别是涉及一种抗真菌活性补骨脂二氢黄酮。该化合物是干燥补骨脂种子，用工业乙醇冷浸提取四次，浸出液减压浓缩得乙醇提取物，加适量水混溶，依次用石油醚、乙酸乙酯萃取；取乙酸乙酯萃取部位浸膏，经硅胶柱层析，用石油醚一乙酸乙酯梯度洗脱，分离得到补骨脂二氢黄酮(石油醚∶乙酸乙酯＝85∶15部分)。可以作为杀菌剂用于防治苹果腐烂病菌，苹果轮纹病菌，水稻稻瘟病菌，水稻纹枯病菌，黄瓜枯萎病菌，小麦赤霉病菌，黄瓜炭疽病菌辣椒疫霉病菌等多种植物病害。
Description
技术领域
本发明涉及一种抗植物真菌病害的化合物，特别是涉及一种抗植物真菌活性补骨脂二氢黄酮。
背景技术
补骨脂二氢黄酮(bavachin)对苹果腐烂病菌、苹果轮纹病菌、水稻稻瘟病菌、水稻纹枯病菌、黄瓜枯萎病菌、小麦赤霉病菌、黄瓜炭疽病菌、辣椒疫霉病菌等多种常见植物病害具有很好的抑菌活性。上述植物病害对我国的农业生产危害严重，据专家报道我国每年因苹果轮纹病危害造成直接经济损失就达30亿到50亿元人民币；水稻稻瘟病，是全世界稻区危害最严重的水稻病害之一，一般造成水稻减产10％～20％，以我国为例，20世纪90年代以来，该病的年发生面积均在380万hm2以上，年损失稻谷达数亿千克。
目前，化学农药的使用仍是防治上述植物病害行之有效的措施，但因一些常规品种的长期使用使病原菌产生抗药性，致使田间用药量逐年加大，对人类健康和生态环境造成极大危害。因此，高效、低毒、低残留、与环境友善同时具有自主知识产权新农药品种的创制迫在眉睫。天然有效成分补骨脂二氢黄酮(bavachin)新功能的发现，可以将其作为先导化合物为新药的创制提供理论依据。同时，补骨脂二氢黄酮(bavachin)作为先导化合物创制新药可以把植物农药和化学农药的优点集于一身，是国内外农药创制的热点之一。
发明内容
本发明的目的在于提供一种补骨脂二氢黄酮(bavachin)可以作为杀菌剂用于防治苹果腐烂病菌(Valsa mali)，苹果轮纹病菌(Physalospora piricola)，水稻稻瘟病菌(Pyricularia oryzae)，水稻纹枯病菌(Rhizoctonia solani Kuhn)，黄瓜枯萎病菌(Fusariumoxysporum)，小麦赤霉病菌(Gibberella zeae)，黄瓜炭疽病菌(Colletotrichum orbiculare)辣椒疫霉病菌(Phytophthora capsici)等多种植物病害。
本发明的目的是通过以下技术方案实现的：
抗植物真菌活性补骨脂二氢黄酮，是干燥补骨脂种子5Kg，用70％工业乙醇冷浸提取四次，浸出液减压浓缩得乙醇提取物，加适量水混溶，依次用石油醚、乙酸乙酯萃取。取乙酸乙酯萃取部位浸膏100g，经反复硅胶柱层析，用石油醚一乙酸乙酯梯度洗脱，分离得到补骨脂二氢黄酮(bavachin)17mg，石油醚∶乙酸乙酯＝85∶15部分。
所述的抗植物真菌活性补骨脂二氢黄酮，其补骨脂二氢黄酮，无色结晶；ESIMS：m/z 324，[M+H]+；HNMR(CD3OD)：d7.64(1H，s，H-5)，7.31(2H，d，J＝8.4Hz，H-2′，6′)，6.87(2H，d，J＝8.4Hz，H-3′，5′)，6.38(1H，s，H-8)，5.31(1H，dd，J＝13.2，3.0Hz，H-2)，5.35(1H，m，H-2″)，3.26(2H，d，J＝6.0Hz，H-2″)，3.03(1H，dd，J＝15.1，13.2Hz，H-3)，2.71(1H，dd，J＝15.9，2.9Hz，H-3)，1.75(3H，s)，1.71(3H，S)；13CNMR(CD3OD)：d192.0(S)，162.9(s)，162.0(s)，156.9(s)，132.3(s)，129.5(s)，127.3(d)，127.3(d)，127.0(d)，123.4(S)，121.4(d)，114.9(d)，114.9(d)，112.9(S)，101.8(d)，79.2(d)，43.5(t)，27.0(t)，24.9(q)，16.8(q)；
补骨脂二氢黄酮结构式：
本发明的优点与效果是：
补骨脂二氢黄酮(bavachin)作为农用杀菌剂具有以下优势：
1.补骨脂二氢黄酮(bavachin)是天然有效成分，本身作为农用杀菌剂具有高效、低毒、低残留、不易产生抗药性等特点。
2.药效高。补骨脂二氢黄酮、福美胂、银泰、甲基托布津、多菌灵5种原药对苹果腐烂病菌菌丝生长的抑制作用EC50分别为1.20、8.93、26.18、9.16、1.47mg/L，EC90分别为12.50、128.98、93.37、147.85、26.86mg/L。可见，补骨脂二氢黄酮的抑菌活性高于防治苹果腐烂病菌的其它药剂。
3.杀菌谱广。补骨脂二氢黄酮(bavachin)对苹果腐烂病菌、苹果轮纹病菌、水稻稻瘟病菌、水稻纹枯病菌、黄瓜枯萎病菌、小麦赤霉病菌、黄瓜炭疽病菌、辣椒疫霉病菌等多种常见植物病害均具有很好的抑制活性。
具体实施方式
本发明涉及的化合物补骨脂二氢黄酮(bavachin)，对苹果腐烂病菌(Valsa mali)，苹果轮纹病菌(Physalospora piricola)，水稻稻瘟病菌(Pyricularia oryzae)，水稻纹枯病菌(Rhizoctonia solani Kuhn)，黄瓜枯萎病菌(Fusarium oxysporum)，小麦赤霉病菌(Gibberellazeae)，黄瓜炭疽病菌(Colletotrichum orbiculare)，辣椒疫霉病菌(Phytophthora capsici)等多种植物病原菌具有很好的抑制活性。
本发明涉及的化合物是干燥补骨脂种子5Kg，用70％工业乙醇冷浸提取四次，浸出液减压浓缩得乙醇提取物，加适量水混溶，依次用石油醚、乙酸乙酯萃取。取乙酸乙酯萃取部位浸膏100g，经反复硅胶柱层析，用石油醚一乙酸乙酯梯度洗脱，分离得到补骨脂二氢黄酮(bavachin)(17mg)(石油醚∶乙酸乙酯＝85∶15部分)。
实例1：用丙酮或二甲基亚砜将补骨脂二氢黄酮溶解配成10g/L的粗提物母液。加入适量粗提物母液于50℃的PDA培养基中，充分混匀，配成粗提物终浓度分别为0.12mg/L、0.6mg/L、3mg/L、15mg/L、75mg/L的含药培养基，以等体积的丙酮或二甲基亚砜加入到PDA培养基中作对照，然后倒入直径90mm培养皿内制成平板，备用。用直径6mm的打孔器从事先在PDA平板上28℃下培养7～12d的各供试病菌菌落边缘处切取菌饼，并移植于上述含不同浓度的粗提物平板和对照平板中央，每次处理重复3次，置28℃下培养7～12d，测量菌落直径。每菌落取相交垂直线方向测其直径，以其均值减去菌饼直径即得菌落净生长直径(CK)，相对抑制率(％)＝(对照净生长量一处理净生长量)/对照净生长量×100。根据病菌抑制率等有关指标，采用相应的数据分析软件，计算出EC50值及EC90值限。
补骨脂二氢黄酮(bavachin)对几种常见植物病原菌菌丝生长的抑制作用。
| 抑制作用 | 苹果腐烂病菌 | 苹果轮纹病菌 | 水稻稻瘟病菌 | 水稻纹枯病菌 | 黄瓜炭疽病菌 | 黄瓜枯萎病菌 | 小麦赤霉病菌 | 辣椒疫霉病菌 |
| EC50(mg/L)EC90(mg/L) | 1.2012.50 | 37.22142.11 | 15.6675.98 | 55.3162.1 | 55.88196.66 | 40.12121.01 | 0.663.25 | 61.00229.31 |
实例2：试验方法同实例1，补骨脂二氢黄酮、福美胂、银泰、甲基托布津、多菌灵6种原药对苹果腐烂病菌菌丝生长的抑制作用如下：
5种药剂对苹果腐烂病菌菌丝生长的抑制作用。
| 抑制作用 | 补骨脂二氢黄酮 | 福美胂 | 银泰 | 甲基托布津 | 多菌灵 |
| EC50(mg/L)EC90(mg/L) | 1.2012.50 | 8.93128.98 | 26.1893.37 | 9.16147.85 | 1.4726.86 |
Claims (1)
1.抗植物真菌活性补骨脂二氢黄酮的提取方法，其特征在于，是干燥补骨脂种子5Kg，用70％工业乙醇冷浸提取四次，浸出液减压浓缩得乙醇提取物，加适量水混溶，依次用石油醚、乙酸乙酯萃取；取乙酸乙酯萃取部位浸膏100g，经反复硅胶柱层析，用石油醚一乙酸乙酯梯度洗脱，分离得到补骨脂二氢黄酮(bavachin)17mg，石油醚∶乙酸乙酯＝85∶15部分。
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