CN103864733B - 一种丁烯酸内酯类代谢产物及其应用 - Google Patents
一种丁烯酸内酯类代谢产物及其应用 Download PDFInfo
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Abstract
本发明涉及一种丁烯酸内酯类代谢产物及其应用,属微生物农药技术领域。本发明的生产菌株为土壤来源的链霉菌YIM 120811(Streptomyces sp. YIM 120811),已于2013年9月9日保藏于中国典型培养物保藏中心,保藏号为CCTCC No: M2013466。本发明由菌株YIM 120811经发酵培养和提取分离获得两个新的丁烯酸内酯类化合物A和B。抗菌活性试验证实本发明的丁烯酸内酯类衍生物具有明显的抗植物病原真菌活性,具有作为制备新的农用抗菌剂的潜在用途。
Description
技术领域
本发明涉及一种丁烯酸内酯类代谢产物及其应用,属微生物农药技术领域。
背景技术
放线菌具有丰富的生物多样性,其天然产物有着广泛的生物学活性,是发现具有生物活性新型次生代谢产物的重要资源。目前临床和农业使用的抗生素约有75%是用放线菌生产的,而在放线菌产生的抗生素中,约有90%是由链霉菌属产生的。因此,从链霉菌中发现活性次生代谢产物具有重要的研究价值。国外研究者曾经从海洋来源的链霉菌中分离获得过丁烯酸内酯类化合物(Cho, et al, J. Nat. Prod. 2001, 64, 664; Mukku et al, J. Nat. Prod. 2000, 63, 1570)。然而,目前还没有将丁烯酸内酯类化合物用作农业抗菌剂的研究报道。
发明内容
本发明的目的在于提供一种从土壤来源的链霉菌YIM 120811 (Streptomyces sp. YIM 120811) 的发酵产物中获得的具有抗植物病原真菌活性的丁烯酸内酯类代谢产物及其应用。
本发明的生产菌株为链霉菌YIM 120811菌株。现在国家知识产权局指定的保藏单位保藏,保藏单位名称:中国典型培养物保藏中心,简称:CCTCC,保藏单位地址:中国,武汉大学,邮政编码:430072。保藏日期为2013年9月9日,保藏编号为CCTCC No: M 2013466。
本发明所述的丁烯酸内酯类代谢产物是从土壤链霉菌YIM 120811 (Streptomyces sp. YIM 120811) 的发酵产物中得到的两种结构类似的新化合物,两种新化合物分别为丁烯酸内酯化合物A,(4S)-4,10-dihydroxy-dodec-2-en-1,4-olide(简称化合物A)和丁烯酸内酯化合物B,(4S)-4,8,10-trihydroxy-10-methyl-dodec-2-en-1,4-olide(简称化合物B)。
丁烯酸内酯化合物A和丁烯酸内酯化合物B的结构式分别为:
丁烯酸内酯化合物A为无色油状物,分子式为C12H20O3;[a] = + 23.7° (c =0.26, CHCl3);UV l max(log ε) (CHCl3): 206 (3.55) nm;IR (KBr): ν max3445, 2950, 2854, 1755, 1612, 1458, 1376, 1158 cm-1;HRESIMS m/z 235.1316 [M + Na]+ (calcd for C12H20O3Na, 235.1310);1H 和13C NMR数据见表1。
丁烯酸内酯化合物B为无色油状物,分子式为C13H22O4;[a] = + 40.6° (c =0.21, CHCl3); UV l max(log ε) (CHCl3): 208 (3.61) nm; IR (KBr): ν max 3437, 2948, 2865, 1756, 1609, 1455, 1402, 1125 cm-1; HRESIMS m/z 265.1421 [M + Na]+ (calcd for C13H22O4Na, 265.1416);1H 和13C NMR数据见表1。
表1 化合物A和B的1H 和13C NMR数据:
化合物A和化合物B的测定溶剂为氘代氯仿,1H NMR数据为500 MHz,13C NMR数据为125 MHz;d in ppm, J in Hz。
本发明的丁烯酸内酯类代谢产物在抗植物病原真菌活性检测中显示较明显的抑制作用,具有作为制备新的农用抗菌剂的潜在用途。
具体实施方式:
实施例1:
化合物A和化合物B的分离制备:
1.链霉菌YIM 120811菌株的斜面培养:配制38#固体培养基 (葡萄糖4 g,酵母膏4 g,麦芽膏5 g,复合维生素微量3.7 mg,微量盐1 mL, 琼脂13 g,蒸馏水1000 mL,pH7.2),灭菌后,制作成试管斜面,挑取链霉菌YIM 120811菌种接入斜面培养基,培养得到斜面菌种;
2.链霉菌YIM 120811菌株的种子培养:配制38#液体培养基 (葡萄糖4 g,酵母膏4 g,麦芽膏10 g,复合维生素微量3.7 mg,微量盐1 mL, 蒸馏水1000 mL,pH7.2),灭菌后,得到种子培养基,将上述培养的斜面菌种转接到种子培养基中,28 ℃、200 r/min摇床培养3天后得到种子液;
3.链霉菌YIM 120811菌株的液体发酵培养:配制改良61#液体培养基 (蛋白胨2 g,葡萄糖20 g,淀粉5g,酵母膏2 g,NaCl 4 g,K2HPO4 0.5 g,MgSO4.7H2O 0.5 g,CaCO3 2 g,蒸馏水1000 mL,pH7.8),灭菌后,得到发酵培养基,将上述种子液转接到发酵培养基中,接种量为10%-20%,28 ℃、200 r/min摇床培养7天后得发酵液。
4.将发酵液离心,上清液用乙酸乙酯萃取,再将乙酸乙酯萃取液浓缩后,获得发酵粗提物,进行硅胶柱层析,以氯仿/甲醇溶剂系统从1:0到1:1梯度洗脱。收集含10%甲醇的氯仿/甲醇洗脱液,减压浓缩。将浓缩液经硅胶柱层析,用石油醚-乙酸乙酯(7:3)洗脱,再经RP-18反相柱层析,用甲醇-水(4:6)洗脱,得到化合物A和化合物B。
实施例2:
采用微量二倍稀释法对本发明的丁烯酸内酯类代谢产物,即化合物A和B进行抗菌活性检测。
1.植物病原真菌指示菌共7株:烟草赤星病菌(Alternaria alternata),稻瘟霉(Pyricularia oryzae),马铃薯干腐病菌(Fusarium coeruleum),番茄灰霉(Botrytis cinema),小麦赤霉病菌(Gibberella saubinetii),苹果炭疽病菌(Colletotrichum gloeosporioides),玉米弯孢霉(Curvularia lunata)。
2.试验方法:
在长有指示菌的固体斜面培养基中加入1mL无菌水,震荡片刻制成指示菌悬液。将待测样品溶解于甲基亚砜,配制成浓度为512 μg/mL的样品溶液,把样品加到96孔细胞板中,采用微量二倍稀释法稀释样品至终浓度为1 μg/mL。然后再将菌悬液依次加入到各孔中,放入恒温箱中25℃培养48小时,肉眼观察,以没有菌生长的最小的样品浓度作为最小抑制浓度(MIC)。未加待测样品只含指示菌的为阴性对照;只含培养基的为空白对照;阳性对照用制霉菌素。
3.试验结果
表2 化合物A和B的抗菌活性
结果表明,本发明的丁烯酸内酯类化合物A和B对7种植物病原真菌指示菌均显示较明显的抑制活性,尤其是化合物A对玉米弯孢霉和烟草赤星病菌的最小抑制浓度值分别为16μg /mL和32 μg/mL,化合物B对苹果炭疽病菌和玉米弯孢霉的最小抑制浓度值为32 μg/mL,具有作为制备新的农用抗菌剂的潜在用途。
Claims (3)
1.一种丁烯酸内酯类代谢产物,其特征在于分别为丁烯酸内酯化合物A和丁烯酸内酯化合物B,结构式分别为:
。
2.如权利要求1所述的丁烯酸内酯类代谢产物,其生产所用的菌株为链霉菌YIM 120811 (Streptomyces sp. YIM 120811),已于2013年9月9日保藏于中国典型培养物保藏中心,保藏号为CCTCC M 2013466。
3.如权利要求1所述的丁烯酸内酯类代谢产物在防治烟草赤星病菌、苹果炭疽病菌、玉米弯孢霉病菌的应用。
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