CN105646430B - 一种可以开发成农业杀菌剂的天然产物及其制备方法 - Google Patents
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Abstract
本发明公开了一种可以开发成农业杀菌剂的天然产物及其制备方法，本发明提供的天然产物天然产物可有效地防治油菜菌核病、水稻纹枯病、草莓灰霉病、小麦赤霉病、辣椒炭疽病、番茄早疫病等，浓度30ppm对这几种病害抑制率分别为60.91％、66.99％、52.30％、44.67％、70.54％、44.66％，具体实验结果见表1；通过实验充分体现了本发明提供的天然产物的显著效果，尤其对真菌性病害油菜菌核病、水稻纹枯病及辣椒炭疽病防治效果明显。因此，可以将本发明提供的天然产物开发成农业杀菌剂，用于保护农作物不受有害生物的侵袭。
Description
技术领域
本发明属于农业领域，具体涉及一种可以开发成农业杀菌剂的天然产物及其制备方法。
背景技术
农作物的病害由于不像害虫和杂草那样容易被人们及时察觉，所以往往造成防治上的忽视和困难，因而其危害就更为严重。据报道，全世界单是由病原真菌引起的植物病害就多达一万种，所造成的损失占作物年度总损失的10％～30％。如果把病毒、细菌和线虫等引起的植物病害也算在内，其损失就更为可观。
为了满足人们对粮食和其它生活物质日益增长的需要，不得不采用化学品以保护作物不受有害生物的侵袭，其中杀菌剂起着重要作用。具有农用杀菌活性的天然产物，一般易被植物吸收和传导，对植物药害小或无药害，因此倍受重视。
发明内容
本发明的目的在于提供一种可以开发成农业杀菌剂的天然产物以及该天然产物的制备方法，该天然产物可以制成杀菌剂，以有效保护农作物不受有害生物的侵袭。
本发明的上述目的是通过下面的技术方案得以实现的：
一种可以开发成农业杀菌剂的天然产物，化学结构式如下：
一种农业杀菌剂，含有如上所述的天然产物和农药助剂或农药赋形剂。
进一步地，所述的农业杀菌剂为乳油、悬浮剂、水乳剂、可湿性粉剂、微乳剂或水分散颗粒剂。
上述的天然产物在防治农业真菌性病害方面的应用。
进一步地，所述的农业真菌性病害为油菜菌核病、水稻纹枯病、草莓灰霉病、小麦赤霉病、辣椒炭疽病和番茄早疫病。
上述的农业杀菌剂在防治农业真菌性病害方面的应用。
进一步地，所述的农业真菌性病害为油菜菌核病、水稻纹枯病、草莓灰霉病、小麦赤霉病、辣椒炭疽病和番茄早疫病。
本发明的优点：
本发明提供的天然产物对农业病害具有优异的防治效果，可以开发成农业杀菌剂，用于保护农作物不受有害生物的侵袭。
具体实施方式
下面结合实施例进一步说明本发明的实质性内容，但并不以此限定本发明保护范围。尽管参照较佳实施例对本发明作了详细说明，本领域的普通技术人员应当理解，可以对本发明的技术方案进行修改或者等同替换，而不脱离本发明技术方案的实质和范围。
实施例1：天然产物的制备和结构确证
分离方法：(a)将补骨脂的干燥成熟果实(5kg)粉碎，用75％乙醇热回流提取(20L×3次)，合并提取液，浓缩至无醇味(4L)，依次用石油醚(4L×3次)、乙酸乙酯(4L×3次)和水饱和的正丁醇(4L×3次)萃取，分别得到石油醚萃取物、乙酸乙酯萃取物和正丁醇萃取物；(b)步骤(a)中正丁醇萃取物用D101型大孔树脂除杂，先用8％乙醇洗脱6个柱体积，再用70％乙醇洗脱8个柱体积，收集70％洗脱液，减压浓缩得70％乙醇洗脱浓缩物；(c)步骤(b)中70％乙醇洗脱浓缩物用正相硅胶分离，依次用体积比为50:1(8个柱体积)、25:1(8个柱体积)、15:1(8个柱体积)和5:1(10个柱体积)的二氯甲烷-甲醇梯度洗脱得到4个组分；(d)步骤(c)中组分4用正相硅胶进一步分离，依次用体积比为10:1(8个柱体积)、5:1(10个柱体积)和2:1(5个柱体积)的二氯甲烷-甲醇梯度洗脱得到3个组分；(e)步骤(d)中组分2用十八烷基硅烷键合的反相硅胶分离，用体积百分浓度为70％的甲醇水溶液等度洗脱，收集8～15个柱体积洗脱液，洗脱液减压浓缩得到一种纯度大于98％的天然产物。
结构确证：HR-ESI-MS显示[M+H]+为m/z 423.2498，结合核磁特征可得分子式为C27H34O4，不饱和度为11。核磁共振氢谱数据δH(ppm，CD3OD，500MHz)：H-1(6.76，br，s)，H-4(5.96，s)，H-5(5.78，s)，H-9(2.12，s)，H-10(2.67，d，J＝11.4Hz)，H-11(2.08，m)，H-12(6.32，dd，J＝11.9，7.7Hz)，H-13(6.53，m)，H-14(2.37，m)，H-14(2.59，m)，H-16(1.02，d，J＝6.7Hz)，H-18(2.81，m)，H-18(3.27，dd，J＝17.1，1.9Hz)，H-20(2.64，m)，H-21(1.34，m)，H-21(1.67，m)，H-22(1.20，m)，H-22(1.26，m)，H-23(1.24，m，2H)，H-24(1.24，m，2H)，H-25(1.25，m，2H)，H-26(0.88，t，J＝7.2Hz)，H-27(1.21，d，J＝7.2Hz)；核磁共振碳谱数据δC(ppm，CD3OD，125MHz)：146.5(CH，1-C)，169.6(C，3-C)，115.8(CH，4-C)，147.2(C，4a-C)，108.1(CH，5-C)，189.8(C，6-C)，122.4(C，7-C)，153.5(C，8-C)，112.3(C，8a-C)，16.2(CH3，9-C)，62.1(CH，10-C)，21.1(CH，11-C)，133.6(CH，12-C)，123.2(CH，13-C)，43.3(CH2，14-C)，206.5(C，15-C)，19.5(CH3，16-C)，41.1(CH2，18-C)，209.3(C，19-C)，46.3(CH，20-C)，32.7(CH2，21-C)，27.6(CH2，22-C)，29.0(CH2，23-C)，31.3(CH2，24-C)，22.2(CH2，25-C)，14.2(CH3，26-C)，16.6(CH3，27-C)。红外波谱中的1710cm-1吸收带与UV谱中的224nm吸收带表明该化合物含有α，β-不饱和羰基结构。13C-NMR、DEPT和HSQC谱中显示有27个碳信号，包括四个甲基，七个亚甲基，八个次甲基(五个烯烃碳)，以及八个季碳(三个羰基碳和五个烯烃碳)，以上功能结构再结合不饱和数表明该化合物为三环结构。1H-NMR谱结合HSQC谱显示四个甲基质子信号δH 2.12(3H，s)、1.02(3H，d，J＝6.7Hz)、0.88(3H，t，J＝7.2Hz)、1.21(3H，d，J＝7.2Hz)，七组亚甲基质子信号δH 2.37(1H，m)与2.59(1H，m)、3.27(1H，dd，J＝17.1，1.9Hz)与2.81(1H，m)、1.67(1H，m)与1.34(1H，m)、1.26(1H，m)与1.20(1H，m)、1.24(2H，m)、1.24(2H，m)、1.25(2H，m)，五个烯烃质子信号δH 6.76(1H，br，s)、5.96(1H，s)、5.78(1H，s)、6.32(1H，dd，J＝11.9，7.7Hz)、6.53(1H，m)，三个次甲基质子信号δH 2.67(1H，d，J＝11.4Hz)、2.08(1H，m)、2.64(1H，m)。1H-1HCOSY谱中存在H-4/H-10/H-11/H-12/H-13/H2-14、H3-27/H-20/H2-21/H2-22/H2-23/H2-24/H2-25/H3-26相关信号，结合HMBC谱中显示的H-1与C-4a、C-8a和C-8，H-4与C-3、C-4a和C-8a，H-5与C-4、C-4a和C-6，H-10与C-3、C-11、C-15和C-16，H-12与C-11、C-13、C-14和C-16，H2-14与C-12、C-13和C-15，H2-18与C-8和C-19，H-20与C-19相关信号，通过上述NMR谱中的相关信息可以构建该化合物的连接方式，并且根据上述波谱数据确认该化合物为Cohaerin衍生物。综合氢谱、碳谱、HMBC谱和ROESY谱，以及文献关于相关类型核磁数据，可基本确定该化合物如下所示，立体构型进一步通过ECD试验确定，理论值与实验值基本一致。该天然产物化学结构和碳原子标记如下：
实施例2：对农业病害的防治
供试菌株核盘菌(Sclerotioia selerotiorum)从油菜菌核病菌株上分离得到；立枯丝核菌(Thanatephorus cucumeris)从水稻纹枯病病叶上分离；灰霉菌(Botrytiscinerea)，又称灰葡萄孢菌从草莓灰霉病上分离得到；禾谷镰孢菌(Fusarium.graminearm)从小麦赤霉病穗上分离得到；禾谷丝核菌(Rhizoctonia solani)从小麦纹枯病叶上分离得到；辣椒疫霉(phytophthora capsici)从辣椒病株上分离；辣椒刺盘孢[Colletotrichumcapsici(syd.)Butl.]从辣椒炭疽病果实上分离得到；茄链格孢菌(Alternaria solani.)从番茄早疫病叶上分离得到。
将实施例1制备的天然产物溶于甲醇制成1000μg/mL母液，4℃保存备用。PDA培养基：200g去皮马铃薯切成块，煮沸10min后，取汁，加入20g琼脂，加热至熔化，再加入20g葡萄糖，用水定容至1000mL。
采用菌丝生长速率测定法对菌丝生长的抑制测定，从PDA平板上预培养的供试菌边缘打取菌碟(直径5mm)，将供试药剂母液与培养基均匀混合，使供试药剂最终浓度为30ppm，混合液倾入直径为9cm的灭菌培养皿中制成平板，每皿接种一菌碟，菌丝面朝上，每处理重复3次。25℃培养至对照菌落布满培养皿三分之二以上时，十字交叉法测量菌落增长直径。
由菌落直径平均值(mm)计算生长抑制率。
以蛇床子素Osthol为阳性对照品，从结果中可以看出实施例1制备的天然产物可有效地防治油菜菌核病、水稻纹枯病、草莓灰霉病、小麦赤霉病、辣椒炭疽病、番茄早疫病等，浓度30ppm对这几种病害抑制率分别为60.91％、66.99％、52.30％、44.67％、70.54％、44.66％，具体实验结果见表1；通过实验充分体现了本发明提供的天然产物的显著效果，尤其对真菌性病害油菜菌核病、水稻纹枯病及辣椒炭疽病防治效果明显。
表1对农业病害的防治
试验结果表明，本发明提供的天然产物对农业病害具有优异的防治效果，可以开发成农业杀菌剂，用于保护农作物不受有害生物的侵袭。
可以将本发明提供的天然产物和农药助剂或农药赋形剂混合制备成农业杀菌剂，剂型可以为乳油、悬浮剂、水乳剂、可湿性粉剂、微乳剂或水分散颗粒剂。
上述实施例的作用在于说明本发明的实质性内容，但并不以此限定本发明的保护范围。本领域的普通技术人员应当理解，可以对本发明的技术方案进行修改或者等同替换，而不脱离本发明技术方案的实质和保护范围。
Claims (7)
1.一种可以开发成农业杀菌剂的天然产物，其特征在于，化学结构式如下：
2.一种农业杀菌剂，其特征在于：含有如权利要求1所述的天然产物和农药助剂或农药赋形剂。
3.根据权利要求2所述的农业杀菌剂，其特征在于：该农业杀菌剂为乳油、悬浮剂、水乳剂、可湿性粉剂、微乳剂或水分散颗粒剂。
4.权利要求1所述的天然产物在防治农业真菌性病害方面的应用。
5.根据权利要求4所述的应用，其特征在于：所述的农业真菌性病害为油菜菌核病、水稻纹枯病、草莓灰霉病、小麦赤霉病、辣椒炭疽病和番茄早疫病。
6.权利要求2所述的农业杀菌剂在防治农业真菌性病害方面的应用。
7.根据权利要求6所述的应用，其特征在于：所述的农业真菌性病害为油菜菌核病、水稻纹枯病、草莓灰霉病、小麦赤霉病、辣椒炭疽病和番茄早疫病。
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| Cohaerins A and B, azaphilo nes from the funus Hypoxylon cohaerens, and comparison of HPLC-based metabolite profiles in Hypoxylon sect. Annulata;Dang Ngoc Quang et al.;《Phytochemistry》;20050228;第66卷;797-809 * |
| Cohaerins C–F, four azaphilones from the xylariaceous fungus Annulohypoxylon cohaerens;Dang Ngoc Quang;《Tetrahedron》;20060511;第62卷;6349-6354 * |
| Cohaerins G–K, azaphilone pigments from Annulohypoxylon cohaerens and absolute stereochemistry of cohaerins C–K;Frank Surup et al.;《Phytochemistry》;20130819;第95卷;252-258 * |
| Inhibition of Nitric Oxide Production in RAW 264.7 Cells by Azaphilones from Xylariaceous Fungi;Dang Ngoc QUANG et al.;《Biol. Pharm. Bull.》;20050926;第29卷(第1期);34-37 * |
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