CN105104394B - 化合物23‑反式‑对‑香豆酰委陵菜酸的应用 - Google Patents
化合物23‑反式‑对‑香豆酰委陵菜酸的应用 Download PDFInfo
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Abstract
本发明公开了化合物23‑反式‑对‑香豆酰委陵菜酸的应用。该化合物的结构如式(一)所示，它对黄瓜灰霉病菌具有较好抑制活性，最小抑制浓度为4μg/mL，可以作为具有杀菌作用的新农药成分或先导化合物。式(一)所示化合物作为植物源天然产物，具有低毒、农药残留低、环境兼容性好等优点。
Description
技术领域
本发明涉及植物源杀菌剂，具体的说是一种委陵菜酸衍生物的应用。
背景技术
黄瓜作为我国主要栽培蔬菜之一，具有较高的经济价值，但每年因为植物病害造成的经济损失都难以估量。黄瓜灰霉病是黄瓜生产中较难防治的植物病害之一，虽然使用化学农药能够起到较好的防治作用，但是经常使用易产生抗药性，并存在对人畜的毒副作用与残留问题。而植物源杀菌剂具有生物活性好、对非靶标生物安全、环境相容性好等优点，已经成为研究开发新农药的热点。
De Tommasi等人自源于意大利的枇杷叶的氯仿提取物部分分离得到4个新的乌苏烷型的三萜酸类化合物：23-trans-p-coumaroyltormentic acid(1)、23-cis-p-coumaroyltormentic acid(2)、3-O-trans-p-caffeoyltormentic acid(3)、3-O-trans-p-coumaroyl rotundic acid(4)，此外还有3个一般的乌苏烷型的三萜酸类化合物(5-7)。进一步研究它们的抗病毒活性证明：仅3-O-trans-p-caffeoyltormentic acid具有明显降低鼻病毒的感染率的活性，但是它对于人类的HIV1和Sindbis病毒的复制无明显抑制作用(deTommasi N,deSimone F,Pizza C,et al.Constituene of Eriobotrya japonica,a studyof their antixiral properties.J.Nat.Prod.,1992,55(8):1067-1073)。在上述文献中，式(一)所示的23-反式-对-香豆酰委陵菜酸(23-trans-p-coumaroyl tormentic acid)不具有抗病毒活性。目前也没有对该化合物生物活性进一步研究的报道。
发明内容
本发明的目的是提供化合物23-反式-对-香豆酰委陵菜酸的应用。该化合物对黄瓜灰霉病具有较好的抑制活性，可用于制备农用杀菌剂。
本发明的技术方案是：化合物23-反式-对-香豆酰委陵菜酸的应用，其特征是，所述式(一)所示的化合物23-反式-对-香豆酰委陵菜酸对黄瓜灰霉病具有较好抑制活性，可用于制备农用杀菌剂。
所述的农用杀菌剂为：以式(一)所示的化合物23-反式-对-香豆酰委陵菜酸为活性成分，加入农业上常用的助剂制备成可湿性粉剂、颗粒剂或缓释剂等。
本发明所具有的优点：式(一)所示化合物23-反式-对-香豆酰委陵菜酸由枇杷叶经提取分离而获得，其对黄瓜灰霉病菌具有较好抑制活性，最小抑制浓度(MIC)为4μg/mL，可以作为具有杀菌作用的新农药成分或先导化合物。式(一)所示化合物作为植物源天然产物，具有低毒、农药残留低、环境兼容性好等优点。
具体实施方式
为阐明对本发明特征的理解，下面结合一些非限定性的实施例对本发明做进一步阐述。
实施例1：
式(一)所示的23-反式-对-香豆酰委陵菜酸(23-trans-p-coumaroyl tormenticacid)为乌苏烷型已知化合物。
式(一)所示的23-反式-对-香豆酰委陵菜酸的制备过程可参见文献de TommasiN,de Simone F,Pizza C,et al.Constituene of Eriobotrya japonica,a study oftheir antixiral properties.J.Nat.Prod.,1992,55(8):1067-1073中的记载进行。
实施例2：抑菌活性试验
采用微量稀释法，测定式(一)所示化合物对黄瓜灰霉病菌的抑菌活性(《从天然产物到新农药创制-原理方法》，吴文君，2006，化学工业出版社)。
1)菌悬液的制备
将供试真菌接种于PDA培养基表面于28℃培养72h后，吸取2mL无菌0.85％NaCl溶液(含0.25％吐温-20)洗涤培养物，并用玻璃刮刀将菌落轻轻刮下。吸取适量菌悬液于无菌试管中，调至0.5麦氏比浊(相当于1.5×108CFU/mL)，备用；
2)样品的配制
分别取1mg待测样品(式(一)化合物)和阳性对照(两性霉素B)，溶解于100μL DMSO中，充分混匀后，吸取50μL样品溶液到另一只离心管中，接着加入50μL DMSO，得到浓度减半的样品溶液。按照此方法，得到12组浓度依次减半的样品溶液。
3)MIC测定方法
(1)采用无菌操作，将倍比稀释后不同浓度的样品溶液分别加到无菌的96孔聚苯乙烯板中，第1至第12孔各加5μL的样品溶液，并以不加样品孔作为空白对照，加5μL DMSO溶液孔为溶剂对照；
(2)将相当于0.5麦氏比浊度的指示菌悬液，经沙氏培养基稀释1000倍后，取95μL依次加入到96孔板中，使得第1至第12孔的样品浓度依次为512、256、128、64、32、16、8、4、2、1、0.5和0.25μg/mL。以上所有样品均重复三次。轻轻震荡混匀后，将96孔板密封置于28℃生化培养箱中培养72h；
(3)在600nm波长下使用酶标仪测定每孔的吸光值，以在小孔内完全抑制指示菌生长的最低样品浓度为该化合物的MIC。(注意：当阴性对照孔内指示菌明显生长实验才有意义；当实验出现单一的跳孔时，应记录抑制菌株生长的最高药物浓度；如出现多处跳孔，则不应报告结果，需重复实验。)
试验结果为式(一)所示化合物对黄瓜灰霉病菌的MIC值为4μg/mL，具有较好抑菌活性。
上述实验结果证明本发明所涉及的化合物具有较好抑菌活性，可用于制备农用杀菌剂。
实施例3：可湿性粉剂
配方(重量比)：23-反式-对-香豆酰委陵菜酸粉末20％，白炭黑20％，十二烷基硫酸钠5％，CMC 1.0％和拉开粉3.0％，凹凸棒土余量。
制备方法：将上述原料混合均匀，控制加工温度0-50℃，在气流粉碎机或其它高目粉碎机中，粉碎到150目以上，水分控制在6-8％(质量百分含量)，pH控制在7-7.5。
使用方法：600倍液喷施，将植株叶片上下喷洒均匀。
Claims (2)
1.式(一)所示的化合物23-反式-对-香豆酰委陵菜酸在制备防治黄瓜灰霉病的农用杀菌剂中的应用，
2.如权利要求1所述的应用，其特征是，所述农用杀菌剂为可湿性粉剂、颗粒剂或缓释剂。
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101172131A (zh) * | 2006-11-01 | 2008-05-07 | 中国医药研究开发中心有限公司 | 委陵菜属植物总三萜提取物的制备方法 |
| CN104381343A (zh) * | 2013-09-17 | 2015-03-04 | 闽南师范大学 | 一种水溶性复配抑菌剂及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101172131A (zh) * | 2006-11-01 | 2008-05-07 | 中国医药研究开发中心有限公司 | 委陵菜属植物总三萜提取物的制备方法 |
| CN104381343A (zh) * | 2013-09-17 | 2015-03-04 | 闽南师范大学 | 一种水溶性复配抑菌剂及其制备方法 |
Non-Patent Citations (2)
| Title |
|---|
| Constituents of Eriobotrya japonica a study of their Antiviral Propreties;Tommasi ET AL;《Journal of Natural Products》;19920831;第55卷(第8期);1067-1073 * |
| 枇杷叶中三萜类化学成分的研究;吕寒等;《中药材》;20080925(第09期);1351-1353 * |
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