Department of Agricultural Chemistry and Biology, Institute of Agricultural Science and Technology.
J Agric Food Chem. 2011 Feb 9;59(3):934-8. doi: 10.1021/jf104027x. Epub 2010 Dec 30.
Microorganisms capable of growth on oils are potential sources of biopesticides, as they produce complex molecules such as biosurfactants and lipopeptides. These molecules have antimicrobial activity against plant pathogens, but few data are available on their insecticidal activity. The present study describes the insecticidal activity of a rhamnolipid isolated from diesel oil-degrading Pseudomonas sp. EP-3 (EP-3). The treatment of cell-free supernatants of EP-3 grown on glucose-mineral medium for 96 h led to > 80% mortality of aphids (Myzus persicae) within 24 h. Bioassay-guided chromatography coupled with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MADLDI-TOF MS) and (¹H, ¹³C) nuclear magnetic resonance (NMR) analyses was employed to isolate and identify the EP-3 insecticidal metabolites. Dirhamnolipid, with molecular formulas of C₃₂H₅₈O₁₃ and C₃₄H₆₂O₁₃, was identified as a main metabolite exhibiting insecticidal activity against aphids. Dirhamnolipid showed a dose-dependent mortality against aphids, producing about 50% mortality at 40 μg/mL and 100% mortality at 100 μg/mL. Microscopy analyses of aphids treated with dirhamnolipid revealed that dirhamnolipid caused insect death by affecting cuticle membranes. This is the first report of rhamnolipid as an insecticidal metabolite against M. persicae. Rhamnolipid shows potential for use as a pesticide to control agricultural pests.
能够以油类为生长基质的微生物是生物农药的潜在来源,因为它们可以产生复杂的分子,如生物表面活性剂和脂肽。这些分子对植物病原体具有抗菌活性,但关于它们的杀虫活性的数据很少。本研究描述了从柴油降解假单胞菌 EP-3 (EP-3) 中分离出的鼠李糖脂的杀虫活性。用葡萄糖-矿物培养基培养 EP-3 96 小时后,细胞上清液处理 24 小时内导致蚜虫(桃蚜)死亡率超过 80%。采用无细胞上清液进行生物测定指导的色谱分离,并结合基质辅助激光解吸/电离飞行时间质谱 (MADLDI-TOF MS) 和 (¹H, ¹³C) 核磁共振 (NMR) 分析,以分离和鉴定 EP-3 的杀虫代谢物。鉴定出具有分子式 C₃₂H₅₈O₁₃和 C₃₄H₆₂O₁₃的二鼠李糖脂是一种主要的杀虫代谢物,对蚜虫具有杀虫活性。二鼠李糖脂对蚜虫表现出剂量依赖性的死亡率,在 40 μg/mL 时产生约 50%的死亡率,在 100 μg/mL 时产生 100%的死亡率。用二鼠李糖脂处理的蚜虫的显微镜分析表明,二鼠李糖脂通过影响角质层膜导致昆虫死亡。这是首次报道二鼠李糖脂作为一种针对桃蚜的杀虫代谢物。二鼠李糖脂具有作为农药控制农业害虫的潜力。