CN102532081B - 佛马内酯和苜萨素类代谢产物及其应用 - Google Patents
佛马内酯和苜萨素类代谢产物及其应用 Download PDFInfo
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Abstract
本发明涉及佛马内酯和苜萨素类代谢产物及其应用,属微生物农药技术领域。本发明的生产菌株Paecilomyces cateniannulatus YMF 1.01773,菌株已于2010年5月10日保存于中国普通微生物菌种保藏管理中心,保藏号为CGMCC NO.3805。本发明由YMF1.01773经常规发酵、提取分离获得4种结构相似的内酯类代谢产物。本发明的佛马内酯和苜萨素类代谢产物在抗棉铃虫活性测试中显示出良好的抑制活性。本发明的内酯类代谢产物具有对环境无污染、成本低、毒杀线虫效果佳的优点,能作为制备杀虫药剂的应用。
Description
技术领域:
本发明涉及佛马内酯和苜萨素类代谢产物及其应用,属微生物农药技术领域。
背景技术:
棉铃虫是一种危害严重的植物病害,每年造成世界农业生产的损失巨大。目前,化学防治仍然是控制棉铃虫的重要措施之一,但长期使用巨毒化学杀虫剂给环境和人类的健康带来的危害日渐显露。因此,研究开发高效低毒的生物杀虫剂已成为农业可持续发展的重要问题。
国内外文献检索表明,目前没有将佛马内酯(Phomalactone)类化合物和苜萨素类(Musacin)作为抗虫生防剂的报道。因此利用佛马内酯类化合物制备抗虫剂是一条值得探索的途径。
发明内容:
本发明的目的是从具有毒杀昆虫功能的真菌中筛选出高毒力环链拟青霉YMF1.01773(Paecilomyces cateniannulatus YMF 1.01773),从该菌株的次生代谢产物中提取高毒力杀虫化合物,为研究开发生物杀线虫制剂和研究开发仿生生物农药奠定基础。本发明是这样实现的:
本发明人在前期研究中,筛选获得了具有良好抗植物寄生昆虫功能的真菌Paecilomyces cateniannulatus YMF 1.01773,菌株已于2010年5月10日保存于中国普通微生物菌种保藏管理中心,保藏号为CGMCC NO.3805。
本发明将YMF 1.01773菌株采用PDA培养基,用常规发酵方法培养,将发酵液低压浓缩后,用氯仿、乙酸乙酯萃取,然后将两部分合并浓缩后,再通过硅胶(氯仿/甲醇洗脱)和Sephedex-LH20凝胶柱(甲醇洗脱)层析,即得到本发明的无色的佛马内酯类和苜萨素化合物,该类化合物是经核磁共振波谱,质谱,红外光谱紫外和旋光光谱确定为3种结构相似的佛马内酯类代谢产物和一个苜萨素;其中产物2和3为两个结构新颖的化合物,命名为catenioblin A和catenioblin B。4种代谢产物的结构如下式1-4所示(以下分别简称为化合物1-4):
本发明的活性化合物1-4的理化性质:
物化特征为:
外观:无色油脂状物质;
溶解性:溶于氯仿、丙酮、二甲亚砜等,不溶于己烷和水等;
化合物2-3的氢谱和碳谱数据见下表。化合物1和4的数据已有文献报道,不在此累述。新化合物2和3的氢谱和碳谱见表2。
核磁谱特征见表1,其溶解溶剂为CD3COCD3,400MHz,δ:ppm.
佛马内酯(Phomalactone,1):Colorless oil; UV(MeOH)λmax(log ε)209.2(3.79)nm;IR(KBr)νmax 3420,2969,2940,2919,2857,1722,1629,1449,1381,1163,1101,1076,1035,969,935,893,830,709,643,560cm-1.
catenioblin A(2):Colorless oil; UV(MeOH)λmax(log ε)270.8(1.84),208.8(2.79)nm;IR(KBr)νmax 3443,2962,2939,2920,2858,1772,1673,1451,1419,1379,1289,1265,1189,1126,1081,1035,1001,970,918,815,648,567,539cm-1;1H NMR(Acetone-d6,400MHz)see Table 1;13C NMR(Acetone-d6,100MHz)see Table 1;Positive HRESI-MS m/z 179.0686[M+Na]+(calculated for C8H12O3Na,179.0684).。
catenioblin B(3):Colorless oil; UV(MeOH)λmax(log ε)281.8(2.61),209.6(3.19)nm;IR(KBr)νmax 3425,2960,2931,2873,1777,1729,1601,1451,1384,1288,1203,1123,1075,1030,970,910,858,796,746,669,652,569cm-1; 1H NMR(Acetone-d6,400MHz)see Table 1;13C NMR(Acetone-d6,100MHz)see Table 1;Positive HRESI-MS m/z 195.0633[M+Na]+(calculated for C8H12O4Na,195.0636).
苜萨素D(Musacin D,4):Colorless oil; UV(MeOH)λ max(log ε)285.2(2.84),209.0(3.52),195.4(2.94)nm;IR(KBr)νmax 3426,2960,2931,2873,1729,1628,1602,1462,1452,1384,1287,1122,1175,1040,964,942,838,745,706,651,568cm-1;1H NMR(Acetone-d6,400MHz)see Table 1;13C NMR(Acetone-d6,100MHz)see Table 1;Positive ESI-MS m/z 177[M+Na]+.
表1.化合物2-3的1H and 13C NMR数据a
aData were measured in acetone-d6 at 400MHz for 1H and 100MHz for 13C with reference to the solvent signals,δin ppm and Jin Hz.
实验表明:本发明的活性化合物在液体滴点法的抗虫活性测试中,在处理时间为48小时时,化合物1-4在浓度为25μg·ml-1对棉铃虫Helicoverpa armigera Hubner的生长抑制率分别为50%,15%,10%和30%,表现了抗虫活性。
因此,该类化合物能够作为制备抗虫药剂的应用。
本发明具有对环境无污染、成本低、毒杀线虫效果佳的优点。
具体实施方式:
实施例1:
化合物1-4的分离制备:
1.真菌ZK7的种子培养:
PDA培养基:马铃薯200g,葡萄糖20g,琼脂15g,水1000ml,自然PH,灭菌后倒成平板。将ZK7菌块接种到平板上,28℃培养5~7天。
2.真菌ZK7的液体发酵培养:
PD培养基:马铃薯200g,葡萄糖20g,水1000ml,自然PH.将平板菌种接种到500ml三角瓶中(每瓶装250ml)液体培养基,在28℃下摇床培养,转速180rpm,培养时间12天。
3.将发酵液过滤,滤液即发酵原液减压浓缩后,分别用氯仿、乙酸乙酯萃取,然后将两部萃取物合并后进行硅胶色谱分离,以甲醇/氯仿=0-25%为洗脱剂梯度洗脱。
4.收集2%~10%的甲醇/氯仿洗脱液,减压浓缩。将浓缩液再进行反复硅胶色谱分离
5.收集TLC板上硫酸显色为紫色的洗脱液浓缩得黄色粉末,经甲醇Sephedex-LH 20反复分离后得到化合物1-4。
实施例2:
用液体滴点法检测本发明化合物的单体抗虫活性的实验:
1.试验用药剂
将化合物1-4溶于10μl丙酮,再加入10%浓度的吐温-20溶液,分别制备200μg·ml-1、100μg·ml-1、50μg·ml-1和25μg·ml-1浓度的供试液,在该溶液中,丙酮的终浓度不超过3%,吐温-20的终浓度不超过0.5%。另将相同浓度的丙酮溶解于含有0.5%(v/v)的吐温-20水溶液作为对照。
2.棉铃虫的培养与制备
棉铃虫作为被测虫体,采购于河南济源白云实业有限公司,并用采购自该公司的人工饲料进行饲养,培养条件是温度为27±1℃,湿度为65-70%。本实验用棉铃虫新生幼虫进行实验,待采购的棉铃虫卵刚孵化后24h将棉铃虫幼虫放置在3.5cm*10cm的圆形玻璃管内,用封口膜封住并用针在封口膜上扎小孔,便于空气流通,同时放置人工饲料在圆形玻璃管底部。每个圆形玻璃管放置一条棉铃虫,避免棉铃虫的自相残杀。
3.试验方法
每个被测浓度设置30条棉铃虫,用移液枪将50μL的待测样品注射至棉铃虫的背部和腹部。分别在24h,48h,72h,96h观察虫子的生长情况和死亡率的情况。并用Image-Pro-ExPress(version 5.1.1.4 for windows 2000/XP professional)进行虫子长度和宽度的测量。
4.实验结果表1.化合物2-3的1H and 13C NMR数据a
aData were measured in acetone-d6 at 400MHz for 1H and 100MHz for 13C with reference to the solvent signals,δinppm and Jin Hz.
表2供试化合物对棉铃虫的生长长度情况影响(48h)
1 | 2 | 3 | 4 | |
0μg/mL | 549.6833+135.2680 | 549.6833+135.2680 | 549.6833+135.2680 | 549.6833+135.2680 |
25μg/mL | 368.9560+193.41796 | 541.1069+167.8970 | 568.1963+157.3664 | 538.8057+158.0906 |
50μg/mL | 273.3679+161.7760 | 528.6628+135.2340 | 564.3073+106.0045 | 552.1208+145.6251 |
100μg/mL | 333.5960+190.5307 | 551.2339+184.8242 | 548.5843+130.5135 | 532.0065+110.1362 |
200μg/mL | 293.9869+189.7650 | 562.3419+120.1361 | 580.2963+186.7541 | 564.5502+167.8251 |
表3供试化合物对棉铃虫的生长宽度情况的影响(48h)
1 | 2 | 3 | 4 | |
0μg/mL | 2715.4324+35.4612 | 2715.4329+35.4612 | 2715.4328+35.4612 | 2715.4325+35.4612 |
25μg/mL | 2243.7466+38.4233 | 2720.2348+28.9970 | 2691.2586+28.3901 | 2648.0912+24.6870 |
50μg/mL | 1772.2984+39.4475 | 2637.2726+27.1367 | 2635.6634+20.5686 | 2715.2215+29.3257 |
100μg/mL | 1969.8123+34.6756 | 2647.5388+26.3328 | 2637.1995+27.4568 | 2611.2927+28.5785 |
实验表明:本发明的活性化合物在液体滴点法的抗虫活性测试中,在处理时间为48小时时,化合物14-在浓度为25μg·ml-1对棉铃虫Helicoverpa armigera Hubner的生长抑制率分别为50%,15%,10%和30%,表现了抗虫活性。
因此,该类化合物能够作为制备抗虫药剂的应用。
本发明具有对环境无污染、成本低、毒杀线虫效果佳的优点。
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CN1631885A (zh) * | 2004-09-30 | 2005-06-29 | 云南大学 | 一类具有毒杀线虫活性的化合物及其应用 |
CN1861593A (zh) * | 2006-04-26 | 2006-11-15 | 云南大学 | 一类间苯酚环融入的大环内酯化合物及其应用 |
CN101830868A (zh) * | 2009-12-09 | 2010-09-15 | 云南大学 | 法尼基环六烷醇类衍生物及其应用 |
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CN1631885A (zh) * | 2004-09-30 | 2005-06-29 | 云南大学 | 一类具有毒杀线虫活性的化合物及其应用 |
CN1861593A (zh) * | 2006-04-26 | 2006-11-15 | 云南大学 | 一类间苯酚环融入的大环内酯化合物及其应用 |
CN101830868A (zh) * | 2009-12-09 | 2010-09-15 | 云南大学 | 法尼基环六烷醇类衍生物及其应用 |
Non-Patent Citations (2)
Title |
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Synthesis and stereochemistry of musacins isolated from Streptomyces griseoviridis (FH-S 1832);Toshihiko Ueki, et al.;《Org. Biomol. Chem.》;20041214;第3卷;295-302 * |
Toshihiko Ueki, et al..Synthesis and stereochemistry of musacins isolated from Streptomyces griseoviridis (FH-S 1832).《Org. Biomol. Chem.》.2004,第3卷295-302. |
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