CN106946955A - 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 - Google Patents
真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 Download PDFInfo
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Abstract
本发明公开了真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用。本发明从落羽杉枝条内生菌中分离得到无柄盘菌(Pezicula sp.)SC1337，其能够产生五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的化合物，因此可以用其制备这五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的化合物，用于植物致病真菌的防治和水果的保鲜，具有广阔的应用前景。
Description
技术领域
本发明属于天然产物领域，具体涉及真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用。
背景技术
植物病害一直是农作物优质高产的重要制约因素之一。在植物病害中，70％～80％的病害是病原真菌侵染所引致的。植物真菌病害不仅直接造成农作物产量下降，农产品贮藏和运输期间大量腐烂变质，造成重大损失，而且部分病原真菌在侵染农作物和农产品过程中，可分泌产生多种对人畜有害的真菌毒素与有害代谢物，对农产品的安全性构成极大威胁。目前，农作物真菌病害的控制往往依赖化学防治，杀菌剂的使用不仅增大生产成本，而且其反复施用不可避免地带来环境污染与农产品农药残留问题。我国主要农作物重大真菌病害的化学防治主要依赖少数杀菌剂，病原真菌生产抗药性而导致杀菌剂丧失防治效果的风险性较高。因此，研发新型、高效的真菌抑制剂意义重大。
传统的化学合成的真菌抑制剂由于长期大量使用，病原菌产生部分抗药性，造成药效减弱，且在环境中不易分解，残留药剂会流失到周围环境中，对农林业生态系统及人类健康造成危害。而天然产物真菌抑制剂对防治对象多有较高选择性，且易于降解，残留较低，对人、畜和有益生物相对安全，环境污染较小，是近年植物病害防治研究的重点之一。目前常用的农用真菌抑制剂如井冈霉素、春雷霉素、多抗霉素、中生霉素、宁南霉素和申嗪霉素等，均来源于环境微生物(主要是植物根际土壤防线菌)次生代谢产物，来自真菌的较少。然而，植物内生真菌次生代谢产物种类丰富、结构多样，也是研发微生物源新型、高效的真菌抑制剂的重要资源。
发明内容
本发明的第一个目的是提供五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的三糖酯化合物。
本发明的三糖酯化合物，其为化合物1、2、3、4或5，所述的化合物1的结构式如式1所示，化合物2的结构式如式2所示，化合物3的结构式如式3所示，化合物4的结构式如式4所示，化合物5的结构式如式5所示，
本发明第二个目的是提供了上述化合物1、2、3、4或5在制备防治真菌病害药物中的应用。
所述的防治真菌病害药物是防治植物真菌病害药物。
一种防治植物真菌病害药物，含有权利要求1中的化合物1、2、3、4或5作为活性成分。
优选，所述的防治植物真菌病害药物是防治Alternaria属真菌、Botryospuaeria属真菌、Botrytis属真菌、Colletotrichum属真菌、Curvularia属真菌、Fusarium属真菌、Geotrichum属真菌、Helminthosporium属真菌、Penicillium属真菌、Peronophythora属真菌、Rhizoctonia属真菌、Ustilaginoidea属真菌的药物。
所述的防治植物真菌病害药物是防治番茄早疫病、苹果轮纹病、番茄灰霉病、芒果炭疽病、香蕉新月弯孢霉、香蕉、西瓜枯萎病、柑橘白地霉病、玉米小斑病、柑橘青霉病、荔枝霜疫霉、水稻纹枯病或稻曲病的药物。
本发明第三个目的是提供化合物1、2、3、4或5在制备水果保鲜剂中的应用。
一种水果保鲜剂，含有权利要求1中的化合物1、2、3、4或5作为活性成分。
优选，所述的水果保鲜剂为柑橘保鲜剂。
本发明从落羽杉枝条内生菌中分离得到无柄盘菌SC1337，其能够产生五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的化合物，因此可以用其制备这五个对12种植物常见致病真菌有明显的抑制活性以及对水果具有保鲜效果的化合物，用于植物致病真菌的防治和水果的保鲜，具有广阔的应用前景。
无柄盘菌(Pezicula sp.)SC1337于2017年2月15日保藏在广东省微生物菌种保藏中心(简称为GDMCC，地址：广州市先烈中路100号大院59号楼广东省微生物研究所，邮编：510070)，保藏号为GDMCC No：60144。
附图说明：
图1是无柄盘菌(Pezicula sp.)SC1337的菌落形态。
图2是无柄盘菌(Pezicula sp.)SC1337菌丝和孢子形态。
具体实施方式：
以下实施例是对本发明的进一步说明，而不是对本发明的限制。
实施例1：
本发明的无柄盘菌(Pezicula sp.)SC1337是从华南植物园的落羽杉枝条内生菌中分离获得，分离方法为：将采集好的落羽杉枝条样品经75％乙醇表面消毒30s，再经质量分数10％次氯酸钠消毒3min，无菌水冲洗3遍后晾干，接种至PDA培养基上，放至28℃培养箱培养5d，用无菌牙签挑取目标菌落即得，所述PDA培养基每升含马铃薯浸提物6g，葡萄糖20g，琼脂20g，其余为水，pH 6.0～6.5，由此分离得到无柄盘菌(Pezicula sp.)SC1337。
无柄盘菌(Pezicula sp.)SC1337的分类学特征：无柄盘菌(Pezicula sp.)SC1337的菌丝宽2～3μm；孢子长椭圆形，大小为14～22×4～6μm，菌落形态和菌丝(含孢子)的形态如图1和图2所示。菌丝体以经典的CTAB法提取得到DNA，通过以ITS4(5’-3’)：TCC TCC GCTTAT TGA TAT GC和ITS5(5’-3’)：GGA AGT AAA AGT CGT AAC AAG G为引物，在10×PCRbuffer 5μL，Mg2+(25mM)4μL，dNTPs(10mM)1μL，Primers(10μM/each)2μL，Taq酶(5U/μL)0.3μL，模板DNA(10ng/μL)5μL，ddH2O 32.7μL的体系中，在94℃5min，94℃40s，57-52℃1min，72℃1min，cycles 35，72℃6min程序下进行PCR扩增后，经测序得到的DNA核苷酸序列如SEQID NO.1所示。测序结果在Genbank数据库用Blast进行检索和同源性比较，其ITS序列片段(共917bp)同源性与Pezicula cinnamomea的同源性最高，ITS相似性为96％。因此将此菌命名为：无柄盘菌(Pezicula sp.)SC1337，于2017年2月15日保藏在广东省微生物菌种保藏中心(简称为GDMCC，地址：广州市先烈中路100号大院59号楼广东省微生物研究所，邮编510070)，保藏号为GDMCC No：60144。
实施例2：5种三糖酯衍生物的制备及其理化和波谱数据：
将无柄盘菌(Pezicula sp.)SC1337在小麦固体培养基(质量比1:1.5的小麦和水混合组成)上，黑暗中于28℃静置培养12d，得到固体发酵培养物。
将固体发酵培养物(3.6L)用等体积的体积分数95％乙醇水溶液浸泡三次，每次48h，浸泡液合并后过滤，然后减压浓缩除去乙醇，并加水定容至1L，再用等体积乙酸乙酯萃取3次，将得到的乙酸乙酯萃取物合并后，再浓缩得到乙酸乙酯提取物17.6g。
乙酸乙酯提取物上硅胶柱(硅胶为100～200目，300g)，以体积比90:10～70:30的氯仿-甲醇混合溶剂进行梯度洗脱，用薄层层析(硅胶板)检测合并相似的流份，收集薄层板上氯仿-甲醇体积比85:15展开时比移值0.3～0.4的流份，减压浓缩得流份A 1.69g，和比移值0.2～0.3的流份，减压浓缩得流份B 8.50g；
将流份A进行反相硅胶柱层析(Develosil ODS，75μm，150g，日本富士化学公司产品)，以体积分数88％的甲醇水溶液等度洗脱，收集主点集中的流份，合并后在高效液相色谱(LC-6AD型半制备高效液相色谱仪，RID-10A检测器，日本Shimadzu公司生产；层析柱为Shim-pack PRC-ODS，10×250mm，4.5μm)以体积分数88％的甲醇水溶液为流动相，流速为5ml/min，纯化得到白色粉末化合物5(0.030g，tR＝60min)。
取流份B 1.0g进行反相硅胶柱层析(Develosil ODS，75μm，150g)，以体积分数65％～85％的甲醇水溶液梯度洗脱，收集85％洗脱部分浓缩后经高效液相色谱(仪器和层析柱同前)，以体积分数87％的甲醇水溶液为流动相，流速为5ml/min，分离纯化得到四个白色粉末物质，分别为化合物1(0.122g，tR＝55min)，化合物2(0.120g，tR＝45min)，化合物3(0.010g，tR＝33min)和化合物4(0.122g，tR＝28min)。
化合物1，白色粉末，分子式为C41H72O19，正离子HRESIMS m/z 891.4552[M+Na]+(calcdfor C41H72O19Na,891.4560)，正离子ESIMS m/z 891[M+Na]+，907[M+K]+；负离子ESIMSm/z867[M－H]－，903[M+Cl]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表1。通过以上光谱数据和二维核磁共振等方法鉴定化合物1为6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-4-O-(8-甲基癸酰)-2-O-(4-甲基己酰)海藻糖，其结构式如式1所示。
其中化合物2，白色粉末，分子式为C40H70O19，正离子HRESIMS m/z 877.4411[M+Na]+(calcd for C40H70O19Na,877.4404)，正离子ESIMS m/z 877[M+Na]+；负离子ESIMS m/z853[M－H]－，889[M+Cl]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表1。通过以上光谱数据和二维核磁共振等方法鉴定化合物2为4-O-癸酰-6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-2-O-(4-甲基己酰)海藻糖，其结构式如式2所示。
其中化合物3，白色粉末，分子式为C39H68O19，正离子HRESIMS m/z 863.4255[M+Na]+(calcd for C39H68O19Na,863.4247)，正离子ESIMS m/z 863[M+Na]+；负离子ESIMS m/z839[M－H]－，875[M+Cl]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表1。通过以上光谱数据和二维核磁共振等方法鉴定化合物3为6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-2-O-(4-甲基己酰)-4-O-(6-甲基辛酰)海藻糖，其结构式如式3所示。
其中化合物4，白色粉末，分子式为C38H66O19，正离子HRESIMS m/z 849.4088[M+Na]+(calcd for C38H66O19Na,849.4091)，正离子ESIMS m/z 849[M+Na]+；负离子ESIMS m/z825[M－H]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表2。通过以上光谱数据和二维核磁共振等方法鉴定化合物4为6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-2-O-(4-甲基己酰)-4-O-辛酰海藻糖，其结构式如式4所示。
其中化合物5，白色粉末，分子式为C43H74O20，正离子ESIMS m/z 933[M+Na]+，949[M+K]+；负离子ESIMS m/z 909[M－H]－，945[M+Cl]－。1H NMR和13C NMR(溶剂：氘代甲醇)的数据见表2。通过以上光谱数据和二维核磁共振等方法鉴定化合物5为6-O-β-L-甘露糖基-3-O-(2-甲基丁酰)-4-O-(8-甲基癸酰)-2-O-(4-甲基己酰)-6'-O-乙酰基海藻糖，其结构式如式5所示。
表1化合物1～3的1H和13C NMR数据
*相应位置的暂定信号可以互换
表2化合物4和5的1H和13C NMR数据
*相应位置的暂定信号可以互换
实施例3：实施例2得到的三糖酯(化合物1～5)的对植物常见12种科属的致病真菌的体外抑制活性试验
所用测试菌种包括：1)Alternaria solani番茄早疫病菌；2)Botryospuaeriaberengeriana苹果轮纹病菌；3)Botrytis cinerea番茄灰霉病菌；4)Colletotrichumgloeosporioides芒果炭疽病菌；5)Curvularia lunata香蕉新月弯孢霉；6)Fusariumoxysporium香蕉、西瓜枯萎病菌；7)Geotrichum citri-aurantii柑橘白地霉病菌；8)Helminthosporium maydis玉米小斑病菌；9)Penicillium italicum柑橘青霉病菌；10)Peronophythora litchii荔枝霜疫霉菌；11)Rhizoctonia solani水稻纹枯病菌；12)Ustilaginoidea virens稻曲病菌。
以滤纸片琼脂扩散法测定化合物1～5的抗真菌活性：将活化好的测试菌分别接种到装有PDA固体培养基的培养皿中，用T型涂布器涂均匀备用；待测试样品以甲醇溶解，配成50mg/mL，实验时取10μL滴加到滤纸片(直径为6mm)上，于超净工作台上晾干，使每滤纸片最终含有样品500μg，然后将滤纸片贴放于上述培养皿中，28℃黑暗条件下培养72或96h后测量抑菌宽度(抑菌宽度为抑菌圈平均直径)，以加入等体积甲醇的滤纸片作阴性对照。
结果显示三糖酯提取物和化合物1～5均可以抑制以上所有真菌的生长，抑菌圈宽度为10～22mm，显示出广谱的真菌抑制活性，结果见表3。所述三糖酯提取物为含有化合物1～4的混合物，其中化合物1、2、3、4质量比约为60:35:4:1。
表3三糖酯提取物和化合物1～5对12种植物致病真菌的体外抑制活性
实施例4：实施例2得到的三糖酯提取物对采后柑橘贮藏中保鲜实验
供试样品：实施例2得到的三糖酯提取物(含化合物1、2、3、4质量比约为60:35:4:1)以少量乙醇溶解，用水稀释为200、400、600mg/L作为处理溶液。
将柑橘果实在处理溶液中浸泡5min，晾干后，将果实置于经75％酒精表面灭菌晾干的塑料筐中，用0.02mm的聚乙烯薄膜袋包装密封，于25℃贮藏15天，观察并记录其感病指数，感病指数计算方法为：0为无明显感染；1为轻微感染；2为感染面积为果实的≤1/4；3为感染面积为果实的1/4-1/2；4为感染面积≥1/2，感病指数＝∑(感病等级×相应果实数量)/(5×果实总数量)×100％。每处理设3个重复，每重复用果约60个。
供试水果：砂糖橘采自从化果园。
实验结果如表4所示。该三糖酯提取物对采后柑橘贮藏过程中的真菌发生发展有明显的抑制作用，优于常用化学抗真菌剂福美双，与特克多相当，具有明显的防腐保鲜作用。该三糖酯提取物的抑菌保鲜效果略差于化学抗真菌剂百可得，但百可得由于毒性较高，2004年已被欧盟禁止使用。
表4三糖酯提取物对采后柑橘果实贮藏中对致病真菌的抑制活性
序列表
<110> 中国科学院华南植物园
<120> 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用
<160> 1
<210> 1
<211> 917
<212> DNA
<213> 无柄盘菌（Pezicula sp.）SC1337
<400> 1
CGAGGTCACC TTGATAGATT GGGGGTTGCT GGCCAGCATC CGCCGGGCGT CTGTAGCGAG 60
AGTATGTACT ACGCTTAGAG CCAGACGGCG CCGCCACTGA TTTTAAGGCA CACCGGGACC 120
GGTGACGCCC AAGACCAAGC AGAGCTTGAG GGTGTAATGA CGCTCGAACA GGCATGCCCC 180
CCGGAATACC AAGGGGCGCA ATGTGCGTTC AAAGATTCGA TGATTCACTG AATTCTGCAA 240
TTCACATTAC TTATCGCATT TCGCTGCGTT CTTCATCGAT GCCAGAACCA AGAGATCCGT 300
TGTTGAAAGT TTTAACTATT ATATAGTACT CAGACGACAC TGACATTCAG GTTTGGGAGT 360
CCTCTGGCGG GCGCGCCCTA GCCGGAGCCA GGGGCAGGGC CGGAGCCCCG CGGCCCGCCA 420
AAGCAACAAA GGTATAACGA CACAGGGTGG GAGGTCTACC CGAAGGGCAG AGTCTCTGTA 480
ATGATCCCTC CGCAGGTTCA CCTACGGAGC GGTTTACGTT CTTGCGAATC CCCAGCACGT 540
TTCCGCGCCG GCCCGACTAT ATCTTAAGCA GGAGAACCTC CTACCCACAA CCACTTAGTC 600
TGTGAACGTT CCCCTGGTCT AGGGGCTTCG CTGCGGATCG TCCATTCCAG CACCTGACTG 660
GATCCTCCGG GGTTGTTACT CTACCCTGTG CAGTTAACAC AGGCCCCTAC TGCATCCCTA 720
CAGTAGGTTA GTACCCAGAG GCTTTAGGAC TTCCCCGCAA TTCGATCGTG TTGCAACTCC 780
GCCGTTGGGC GTCGTCACTT GCGTGCCTCC TTATTTAGAG TCGCGAGAGC CCCCTTTCGG 840
GGTGCAAAGG CTTCCTCAAG TTCGCTGCAG AGAGATCACT GCTCTACGGA GACCTTGTAC 900
TTTTTTTTAT TACTTCC 917
Claims (9)
1.三糖酯化合物，其为化合物1、2、3、4或5，所述的化合物1的结构式如式1所示，化合物2的结构式如式2所示，化合物3的结构式如式3所示，化合物4的结构式如式4所示，化合物5的结构式如式5所示，
2.权利要求1中的化合物1、2、3、4或5在制备防治真菌病害药物中的应用。
3.根据权利要求2所述的应用，其特征在于，所述的防治真菌病害药物是防治植物真菌病害药物。
4.根据权利要求3所述的应用，其特征在于，所述的防治植物真菌病害药物是防治Alternaria属真菌、Botryospuaeria属真菌、Botrytis属真菌、Colletotrichum属真菌、Curvularia属真菌、Fusarium属真菌、Geotrichum属真菌、Helminthosporium属真菌、Penicillium属真菌、Peronophythora属真菌、Rhizoctonia属真菌或Ustilaginoidea属真菌的药物。
5.一种防治植物真菌病害药物，其特征在于，含有权利要求1中的化合物1、2、3、4或5作为活性成分。
6.根据权利要求5所述的防治植物真菌病害药物，其特征在于，所述的防治植物真菌病害药物是防治Alternaria属真菌、Botryospuaeria属真菌、Botrytis属真菌、Colletotrichum属真菌、Curvularia属真菌、Fusarium属真菌、Geotrichum属真菌、Helminthosporium属真菌、Penicillium属真菌、Peronophythora属真菌、Rhizoctonia属真菌或Ustilaginoidea属真菌的药物。
7.根据权利要求5所述的防治植物真菌病害药物，其特征在于，所述的防治植物真菌病害药物是防治番茄早疫病、苹果轮纹病、番茄灰霉病、芒果炭疽病、香蕉新月弯孢霉、香蕉、西瓜枯萎病、柑橘白地霉病、玉米小斑病、柑橘青霉病、荔枝霜疫霉、水稻纹枯病或稻曲病的药物。
8.权利要求1中的化合物1、2、3、4或5在制备水果保鲜剂中的应用。
9.根据权利要求8所述的应用，其特征在于，所述的水果保鲜剂为柑橘保鲜剂。
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| WO2018166159A1 (zh) * | 2017-03-15 | 2018-09-20 | 中国科学院华南植物园 | 无柄盘菌sc1337菌株和利用它制备三糖酯衍生物的方法 |
| WO2018166158A1 (zh) * | 2017-03-15 | 2018-09-20 | 中国科学院华南植物园 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
| CN110038019A (zh) * | 2019-05-27 | 2019-07-23 | 惠州学院 | 一种三糖酯类化合物在制备抗细胞增殖性紊乱或抗癌药物中的应用 |
| CN110511878A (zh) * | 2019-07-31 | 2019-11-29 | 中国林业科学研究院亚热带林业研究所 | 具抑菌能力和木质纤维素降解活性的新孢无柄盘菌及用途 |
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| CN111887056B (zh) * | 2020-06-30 | 2022-11-01 | 阿克苏优能农业科技股份有限公司 | 促糖心防虫害的苹果果树调控剂及应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1269361A (zh) * | 2000-04-28 | 2000-10-11 | 吴忠 | 葡聚烯糖化合物及其合成方法与应用 |
| CN105506029A (zh) * | 2016-01-06 | 2016-04-20 | 西南大学柑桔研究所 | 用柑橘皮制备抗真菌果胶低聚糖的方法及其应用和柑橘保鲜方法 |
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| CN106946955B (zh) * | 2017-03-15 | 2019-06-21 | 中国科学院华南植物园 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
| CN106867917B (zh) * | 2017-03-15 | 2019-06-21 | 中国科学院华南植物园 | 无柄盘菌sc1337菌株和利用它制备三糖酯衍生物的方法 |
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| CN1269361A (zh) * | 2000-04-28 | 2000-10-11 | 吴忠 | 葡聚烯糖化合物及其合成方法与应用 |
| CN105506029A (zh) * | 2016-01-06 | 2016-04-20 | 西南大学柑桔研究所 | 用柑橘皮制备抗真菌果胶低聚糖的方法及其应用和柑橘保鲜方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018166159A1 (zh) * | 2017-03-15 | 2018-09-20 | 中国科学院华南植物园 | 无柄盘菌sc1337菌株和利用它制备三糖酯衍生物的方法 |
| WO2018166158A1 (zh) * | 2017-03-15 | 2018-09-20 | 中国科学院华南植物园 | 真菌三糖酯化合物及其在制备防治植物真菌病害药物中的应用 |
| CN110038019A (zh) * | 2019-05-27 | 2019-07-23 | 惠州学院 | 一种三糖酯类化合物在制备抗细胞增殖性紊乱或抗癌药物中的应用 |
| CN110511878A (zh) * | 2019-07-31 | 2019-11-29 | 中国林业科学研究院亚热带林业研究所 | 具抑菌能力和木质纤维素降解活性的新孢无柄盘菌及用途 |
| CN110511878B (zh) * | 2019-07-31 | 2021-06-11 | 中国林业科学研究院亚热带林业研究所 | 具抑菌能力和木质纤维素降解活性的新孢无柄盘菌及用途 |
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