CN112592269A - 镰刀霉属植物内生微生物中分离出的链状萜类衍生物及其分离方法和应用 - Google Patents
镰刀霉属植物内生微生物中分离出的链状萜类衍生物及其分离方法和应用 Download PDFInfo
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Abstract
镰刀霉属植物内生微生物中分离出的链状萜类衍生物及其分离方法和应用，属于生物农药领域。本发明从采集自长白红景天叶片部位的内生镰刀霉属微生物的固体发酵产物中分离得到三个新型链状萜类衍生物。本发明的原料为植物内生微生物发酵产物，安全易得，方法简单易操作，不引入有毒物质，成本低廉，可大规模持续开发利用。
Description
技术领域
本发明属于生物农药领域，具体涉及镰刀霉属植物内生微生物中分离出的链状萜类衍生物及其分离方法和应用。
背景技术
目前从微生物代谢产物中分离得到50000种以上的天然产物，其中多种化合物生物活性良好，具有被开发成为生物农药的潜质。随着研究的深入，从传统陆生微生物代谢产物中获得新型先导化合物的概率逐渐降低，速度逐年减缓，故开发特境微生物资源成为当务之急。植物内生微生物由于其生境特殊，能够代谢产生结构特殊，活性良好的化合物，是目前的研究热点之一。
发明内容
本发明涉及从采集自长白红景天叶片部位的内生镰刀霉属微生物的固体发酵产物中分离得到三个新型链状萜类衍生物，该类化合物对单子叶杂草野燕麦、早熟禾、稗草、马唐等有明显的抑制活性，对双子叶植物苜蓿，大豆等无明显抑制作用。
本发明分离出三种链状萜类衍生物，三种链状萜类衍生物的分子结构式如下：
化合物1为(E)-9,10-二羟基-2,6,10-三甲基-5-十一烯酸，化合物2为(E)-1,8-二羟基-4,8-二甲基-3-壬酸甲酯，化合物3为(3E,7E)-11,12-二羟基-4,8,12-三甲基-3,7-二烯十三酰胺。
本发明同时保护镰刀霉属植物内生微生物中分离出的链状萜类衍生物的分离方法，具体步骤如下：
(1)将采集自长白红景天叶片部位的内生镰刀霉属真菌接种于培养基发酵液的锥形瓶中摇床震荡培养2天，再将震荡培养后的发酵液连同菌丝按接种量10％的比例体接种于装有固体培养基的锥形瓶中静止发酵培养40天，培养温度为28摄氏度。其中固体培养基为大米和纯净水。
(2)代谢产物的提取：使用等体积丙酮对植物内生真菌固体发酵产物进行超声提取，提取3次，每次15分钟后经8层纱布过滤，将提取液与菌丝体及大米分离，提取液浓缩至干，加水将提取浸膏混悬，使用等体积乙酸乙酯溶液萃取3次，将萃取液减压回收有机溶剂得到乙酸乙酯层代谢产物。
(3)乙酸乙酯层用正相硅胶柱色谱分离纯化，采用二氯甲烷：甲醇(100︰0-0︰100)进行梯度洗脱，得到各梯度洗脱流份。
(4)步骤(3)的洗脱液经高效液相色谱分离纯化，通过60％甲醇水等度洗脱，210nm,保留时间16min得化合物1；通过60％甲醇水等度洗脱，210nm,保留时间10min得化合物2；通过20％-95％甲醇水梯度洗脱，254nm，保留时间31min得化合物3。
本发明同时保护镰刀霉属植物内生微生物中分离出的链状萜类衍生物在生物农药方面的应用。
有益效果：本发明的原料为植物内生微生物发酵产物，安全易得，方法简单易操作，不引入有毒物质，成本低廉，可大规模持续开发利用。在生物农药研究开发上具有非常重要的意义。
具体实施方式
下面结合实施例对本发明作进一步说明。
实施例1
(1)将采集自长白红景天叶片部位的内生镰刀霉属真菌进行固体发酵。
固体培养基配方：大米80g，哇哈哈纯净水120ml。
发酵条件：将菌株接种于4瓶装有200mL真菌4号培养基发酵液的500mL锥形瓶中摇床震荡培养2d(培养条件：28℃，120r/min)，再将震荡培养2d后的发酵液连同菌丝体按接种量10％的比例接种于100瓶装有固体培养基的500mL锥形瓶中静置发酵培养40d(培养条件：28℃)。
(2)代谢产物的提取：培养40d后的固体发酵产物用等体积丙酮溶液进行超声提取，提取3次每次15min，提取液使用8层纱布过滤，将菌丝体与大米残余物去除，使用旋转蒸发仪浓缩提取液至干，加适量的水将提取浸膏混悬，使用等体积乙酸乙酯溶液萃取3次，将萃取液减压回收有机溶剂得到乙酸乙酯层代谢产物(38.89g)。
(3)乙酸乙酯层用正相硅胶柱色谱分离纯化，采用二氯甲烷：甲醇(100︰0-0︰100)进行梯度洗脱，得到各梯度洗脱流份。
(4)步骤(3)的洗脱液经高效液相色谱分离纯化，通过60％甲醇水等度洗脱，210nm,保留时间16min得化合物1；通过60％甲醇水等度洗脱，210nm,保留时间10min得化合物2；通过20％-95％甲醇水梯度洗脱，254nm，保留时间31min得化合物3。
采用核磁共振(NMR)等波谱技术测定其结构，化合物1-3的波谱数据见下表。
表1化合物1氢谱(500MHz)和碳谱(125MHz)核磁数据(DMSO-d6)
表2化合物2氢谱(500MHz)和碳谱(125MHz)核磁数据(DMSO-d6)
表3化合物3氢谱(500MHz)和碳谱(125MHz)核磁数据(DMSO-d6)
实施例2
化合物1、化合物2和化合物3应用在农业除草方面。
上述实施例只是用于对本发明的举例和说明，而非意在将本发明限制于所描述的实施例范围内。此外本领域技术人员可以理解的是，本发明不局限于上述实施例，根据本发明的教导还可以做出更多种的变型和修改，这些变型和修改均落在本发明所要求保护的范围内。
Claims (5)
1.镰刀霉属植物内生微生物中分离出的链状萜类衍生物，其特征在于，镰刀霉属植物内生微生物中分离出的链状萜类衍生物为化合物1、化合物2和化合物3，三种化合物的分子结构式如下：
其中化合物1为(E)-9,10-二羟基-2,6,10-三甲基-5-十一烯酸，化合物2为(E)-1,8-二羟基-4,8-二甲基-3-壬酸甲酯，化合物3为(3E,7E)-11,12-二羟基-4,8,12-三甲基-3,7-二烯十三酰胺。
2.权利要求1中镰刀霉属植物内生微生物中分离出的链状萜类衍生物的分离方法，其特征在于，具体步骤如下：
S1.将采集自长白红景天叶片部位的内生镰刀霉属真菌接种于培养基发酵液的锥形瓶中摇床震荡培养2天，再将震荡培养后的发酵液连同菌丝按接种量10％的比例体接种于装有固体培养基的锥形瓶中静止发酵培养40天，培养温度为28摄氏度，其中固体培养基为大米和纯净水；
S2.代谢产物的提取：使用等体积丙酮对植物内生真菌固体发酵产物进行超声提取，经纱布过滤，将提取液与菌丝体及大米分离，提取液浓缩至干，加水将提取浸膏混悬，使用乙酸乙酯溶液萃取，将萃取液减压回收有机溶剂得到乙酸乙酯层代谢产物；
S3.乙酸乙酯层用正相硅胶柱色谱分离纯化，采用二氯甲烷：甲醇100︰0-0︰100进行梯度洗脱，得到各梯度洗脱流份；
S4.步骤S3的洗脱液经高效液相色谱分离纯化，得化合物1、化合物2和化合物3。
3.根据权利要求2所述的镰刀霉属植物内生微生物中分离出的链状萜类衍生物的分离方法，其特征在于，步骤S2中乙酸乙酯的加入量与混悬液体积相同，萃取次数为3次。
4.根据权利要求2所述的镰刀霉属植物内生微生物中分离出的链状萜类衍生物的分离方法，其特征在于，步骤S4中洗脱液经高效液相色谱分离纯化，通过60％甲醇水等度洗脱，210nm,保留时间16min得化合物1；通过60％甲醇水等度洗脱，210nm,保留时间10min得化合物2；通过20％-95％甲醇水梯度洗脱，254nm，保留时间31min得化合物3。
5.权利要求1中镰刀霉属植物内生微生物中分离出的链状萜类衍生物在生物农药方面的应用。
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| QI-LING LI 等: "Acyclic Isoprenoids of Endophytic Aspergillus sp. Y-12 from Panax notoginseng", 《LETTERS IN ORGANIC CHEMISTRY》 * |
| XUAN LU 等: "Terpenoid derivatives from the endophytic fungus Fusarium sp. HJT-P-2 of Rhodiola angusta Nakai", 《PHYTOCHEMISTRY LETTERS》 * |
| 魏磊 等: "长白红景天内生真菌Fusarium sp. HJT-P-5次级代谢产物研究", 《沈阳药科大学学报》 * |
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