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二苯并-α-吡喃酮类化合物:一种新型杀蚊幼虫代谢产物,来自内生真菌 Hyalodendriella sp. Ponipodef12。

Dibenzo-α-pyrones: a new class of larvicidal metabolites against Aedes aegypti from the endophytic fungus Hyalodendriella sp. Ponipodef12.

机构信息

Key Laboratory of Plant Pathology, Ministry of Agriculture/Department of Plant Pathology, College of Plant Protection, China Agricultural University, Beijing, China.

Department of Entomology, College of Plant Protection, China Agricultural University, Beijing, China.

出版信息

Pest Manag Sci. 2017 Jul;73(7):1478-1485. doi: 10.1002/ps.4481. Epub 2017 Jan 5.

DOI:10.1002/ps.4481
PMID:27862895
Abstract

BACKGROUND

In our search for new agrochemicals from endophytic fungi, the crude extract of the endophytic Hyalodendriella sp. Ponipodef12 associated with the hybrid 'Neva' of Populus deltoides Marsh × P. nigra L. was found to possess larvicidal activity against Aedes aegypti.

RESULTS

Fractionation of the extract has led to the isolation of 11 dibenzo-α-pyrones (1-11), including three new congeners: hyalodendriols A-C (1-3). The structures of the new compounds were elucidated by comprehensive spectroscopic analyses, including the modified Mosher's method for the assignment of the absolute configuration. Compounds 2-7 showed potent larvicidal activities against the fourth-instar larvae of A. aegypti with IC values ranging from 7.21 to 120.81 µg mL . Among them, penicilliumolide D (6) displayed the strongest activity (IC = 7.21 µg mL ). A structure-larvicidal activity relationship was discussed. The possible mode of action of these compounds was assessed for their acetylcholinesterase inhibitory activities. In addition, hyalodendriol C (3) displayed antibacterial activity against Bacillus subtilis and Xanthomonas vesicatoria, and exhibited strong inhibition against the spore germination of Magnaporthe oryzae.

CONCLUSION

Our study revealed dibenzo-α-pyrones to be a new class of larvicidal metabolites against A. aegypti. © 2016 Society of Chemical Industry.

摘要

背景

在寻找内生真菌源新农药的过程中,我们发现与杂交白杨‘Neva’(美洲黑杨×黑杨)相关的内生拟盘多毛孢 Ponipodef12 的粗提物具有杀蚊幼虫活性,可有效防治埃及伊蚊。

结果

提取物的分离导致了 11 种二苯并-α-吡喃酮(1-11)的分离,包括三种新同系物:hyalodendriols A-C(1-3)。新化合物的结构通过综合光谱分析阐明,包括莫舍尔法用于绝对构型的分配。化合物 2-7 对埃及伊蚊四龄幼虫表现出很强的杀蚊幼虫活性,IC 值范围为 7.21-120.81μg/mL。其中,penicilliumolide D(6)表现出最强的活性(IC = 7.21μg/mL)。讨论了结构与杀蚊幼虫活性的关系。评估了这些化合物对乙酰胆碱酯酶抑制活性的可能作用模式。此外,hyalodendriol C(3)对枯草芽孢杆菌和番茄细菌性斑点病菌具有抗菌活性,并对稻瘟病菌孢子萌发表现出强烈抑制作用。

结论

本研究表明二苯并-α-吡喃酮是一种新型的针对埃及伊蚊的杀蚊幼虫代谢产物。© 2016 英国化学学会。

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