CN108424404B - 一种抗甘薯黑斑病菌的化合物及其制备方法和应用 - Google Patents
一种抗甘薯黑斑病菌的化合物及其制备方法和应用 Download PDFInfo
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Abstract
一种可用于抗甘薯黑斑病菌的化合物,经鉴定,其为2‑(1‑羟基‑2‑乙酰氧基)丙基‑7‑氧杂二环[4.1.0]‑2,4‑庚二烯。该化合物的制备方法为,将一株肉座目真菌(Hypocreales sp.)菌株活化培养后接种到培养基上进行发酵培养,再将发酵培养后的上清液用乙酸乙酯萃取,浓缩,得乙酸乙酯浸膏,最后将乙酸乙酯浸膏经两次柱层析纯化,得到目标产物。该化合物对甘薯黑斑病菌的抑制作用实验结果表明,其对甘薯黑斑病菌具有很好的抑制作用,可作为生物农药替代化学农药用于防治甘薯黑斑病。该化合物为天然产物,无污染、无毒素残留、对人畜和环境不构成危害。
Description
技术领域
本发明涉及生物农药领域,尤其涉及一种抗甘薯黑斑病菌的化合物及其制备方法和应用。
背景技术
甘薯黑斑病菌,又称甘薯长喙壳菌(Ceratocystis fimbriata EllisetHalsted),其侵染甘薯能引起甘薯黑斑病,是甘薯生产中的一种重要病害,分布广泛,对我国甘薯生产造成严重损失。目前,对甘薯黑斑病的防治技术主要包括农业防治和化学防治。农业防治是指防治农作物病害所使用的农业技术,即改变作物的生长环境,以增强作物对病害的抵抗力。农业防治的主要措施包括三个方面:一、育种,即选择具有抗病性的种子,从而得到健康种苗;二、田间管理,即合理施肥,及时灌溉松土;三、田间布局,即实施轮作和调节播种期等。农业防治措施的效果不能立竿见影,是随着逐年的积累显现出来的,因此只是具有一定的预防作用,且还受人力、季节和地区等多种因素的限制,效果不明显易见。化学防治是用化学药剂来防治植物病害的技术。化学农药具有经济效益高、效率高、效果明显、方便、快捷等优点,但如果使用不当不仅对植物产生伤害,杀害有益微生物,还会引起人畜中毒,甚至导致病原微生物产生抗药性。农药的高残留还会对生态环境造成严重污染。因此,寻找新的防治甘薯黑斑病菌的方法迫在眉睫。
生物防治是利用各个生物之间的关系,即用一种生物抑制另一种不同生物,或者是利用生物的代谢产物,即生物农药来防治病害的方法。生物防治具有特异性强、毒性低、病原菌不易产生抗药性、天然产物易降解、对环境污染小等优点,现已成为植物病害防治发展的一个重要方向,成为现代科技工作者研究的重点领域。目前,有关拮抗甘薯黑斑病菌的生物农药鲜有报道。
发明内容
本发明的一个目的在于提供一种可用于抗甘薯黑斑病菌的化合物,其结构式如下式(Ⅰ)所示,
本发明的另一个目的在于提供上述化合物的制备方法,包括步骤:
S1:将肉座目真菌(Hypocreales sp.)菌株活化培养后接种到培养基上进行发酵培养,其中,所用肉座目真菌(Hypocreales sp.)菌株保藏编号为CGMCC NO:14981;
S2:将发酵培养后的上清液用乙酸乙酯萃取,浓缩,得乙酸乙酯浸膏;
S3:将乙酸乙酯浸膏装柱、洗脱、柱层析纯化,得到目标产物。
优选的,所述步骤S3中的洗脱以石油醚-乙酸乙酯混合液、乙酸乙酯-甲醇混合液和纯甲醇为洗脱溶剂。
优选的,所述步骤S3中的柱层析纯化利用石油醚-丙酮混合液进行洗脱。
优选的,所述石油醚与丙酮的体积比为3:7。
本发明还提供了上述化合物在生物防治中的应用。
优选的,生物防治的对象为甘薯黑斑病菌。
本发明的有益效果:
1.本发明提供了一种新型的可用于防治甘薯黑斑病菌的化合物;
2.本发明的防治甘薯黑斑病菌的化合物制备方法,工艺简单易行、条件温和、易于控制;
3.以真菌发酵的产物防治甘薯黑斑病,成本低、使用简单,且无污染、无毒素残留、对人畜和环境不构成危害。
本发明所用的菌种保藏日期为2017年11月24日,保藏编号为:CGMCC No.14981。分类名称为:肉座菌目真菌(Hypocreales sp.),保藏单位名称为中国微生物菌种保藏管理委员会普通微生物中心,地址为北京市朝阳区北辰西路1号院3号,邮编100101。
附图说明
图1为本发明实施例1所述化合物2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯的1H NMR图谱(400MHz,CDCl3);
图2为本发明实施例1所述的化合物2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯的13C NMR图谱(100MHz,CDCl3);
图3为本发明实施例1所述的化合物2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯的1H-1H COSY图谱(CDCl3);
图4为本发明实施例1所述的化合物2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯的13C/DEPT135NMR图谱(CDCl3);
图5为本发明实施例1所述的化合物2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯的HSQC图谱(CDCl3);
图6为本发明实施例1所述的化合物2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯的HMBC图谱(CDCl3)。
具体实施方式:
实施例1:抗甘薯黑斑病菌的化合物的制备
将菌株KLBMP-Pt686发酵液30L与乙酸乙酯按1:1比例萃取3次,合并后减压浓缩干燥得乙酸乙酯浸膏(9.5g)。将所得的浸膏与硅胶(200-300目)进行拌样,混匀后干法上硅胶柱(450mm×55mm,200-300目)进行分离,以石油醚:乙酸乙酯(10:1和1:1),乙酸乙酯:甲醇(1:1)和甲醇为洗脱溶剂进行梯度洗脱,共收集60个组分。将收集的组分再次进行硅胶柱层析,利用石油醚:丙酮(3:7)混合液洗脱,流出液按10mL/瓶收集,挥干溶剂,得到淡黄色固体,即为目标化合物(31.0mg)。该化合物的表征为:淡黄色固体,熔点77.1℃-78.0℃,易溶于乙酸乙酯、丙酮、氯仿等,1H-NMR(500MHz,CDCl3),δH:1.57(s,3H,H-2”),1.76~1.80(d,3H,H-3'),2.90~2.94(b,1H,1'-OH),4.06~4.09(d,2H,H-1/H-6),4.24~4.27(m,1H,H-1'),4.34~4.39(m,1H,H-2'),5.68~5.73(m,1H,H-3),5.87~5.96(m,1H,H-4),6.85~6.87(m,1H,H-5),其中s表示单峰,d表示双峰,b表示宽峰,m表示多重峰;13C-NMR(100MHz,CDCl3),δc:79.79.20(C-1),133.82(C-2),125.84(C-3),131.19(C-4),133.04(C-5),63.97(C-6),79.75(C-1'),79.17(C-2'),18.12(C-3'),167.01(C-1”),18.78(C-2”)。该化合物的1H NMR图谱(400MHz)如图1所示,13C NMR图谱(100MHz)如图2所示,1H-1H COSY图谱如图3所示,13C/DEPT135NMR图谱如图4所示,HSQC图谱如图5所示,HMBC图谱如图6所示。根据以上数据确定该化合物为2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯,其结构式如下:
实施例2:化合物2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯的对甘薯黑斑病菌的抑制作用测定
吸取100μL的甘薯黑斑病孢子悬液(1×106cfu/mL)涂抹在PDA平板上,在平板中心位置垂直放上牛津杯,然后轻微加压使牛津杯与培养基表面无空隙。
将化合物2-(1-羟基-2-乙酰氧基)丙基-7-氧杂二环[4.1.0]-2,4-庚二烯用20%的DMSO溶解并配制成浓度为400μg/mL、200μg/mL和100μg/mL的溶液。
在牛津杯中分别加入上述不同浓度的样品溶液200μL(以20%DMSO无菌溶液做对照),重复三次。加好样品后的平板放置培养箱中培养4d,观察抑菌结果并测量抑菌圈直径。
结果显示,目标化合物浓度在400μg/mL时对甘薯黑斑病的平均抑菌圈直径为33.33±1.53mm,浓度在200μg/mL时对甘薯黑斑病的平均抑菌直径为25.33±0.58mm,当浓度在100μg/mL时对甘薯黑斑病的平均抑菌直径为16.00±1.00mm。实验结果表明,该化合物对甘薯黑斑病菌具有很好的抑制作用。
Claims (4)
2.制备权利要求1所述的抗甘薯黑斑病菌的化合物的方法,其特征在于,包括步骤:
S1:将肉座目真菌(Hypocreales sp .)菌株活化培养后接种到培养基上进行发酵培养,所述肉座目真菌(Hypocreales sp .)菌株保藏编号为CGMCC NO.14981;
S2:将发酵培养后的上清液用乙酸乙酯萃取,浓缩,得乙酸乙酯浸膏;
S3:将乙酸乙酯浸膏装柱、洗脱、两次柱层析纯化,得到目标产物;所述步骤S3中第一次柱层析纯化的洗脱以石油醚-乙酸乙酯混合液、乙酸乙酯-甲醇混合液和纯甲醇为洗脱溶剂;所述步骤S3中的第二次柱层析纯化以石油醚-丙酮混合液进行洗脱。
3.根据权利要求2所述的制备方法,其特征在于,所述石油醚与丙酮的体积比为3:7。
4.权利要求1所述的化合物在甘薯黑斑病菌防治中的应用。
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