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首页> 外文期刊>Journal of Agricultural and Food Chemistry >Novel Inhibitors of an Insect Pest Chitinase: Design and Optimization of 9-O-Aromatic and Heterocyclic Esters of Berberine
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Novel Inhibitors of an Insect Pest Chitinase: Design and Optimization of 9-O-Aromatic and Heterocyclic Esters of Berberine

机译：昆虫害虫胰蛋白酶的新型抑制剂：小檗碱90 o型芳香族和杂环酯的设计与优化

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摘要

OfChi-h, a lepidopteran-exclusive glycoside hydrolase family 18 (GH18) chitinase from the agricultural insect pest Ostrinia furnacalis, is a promising molecular target candidate for pest control and management. Berberine (BER), a traditional Chinese medicine, binds to a wide variety of glycosyl hydrolases via an identical mechanism, showing potential as a pesticide lead compound. In this work, we found that BER was a moderate inhibitor of OfChi-h with a Ki of 16.1 mu M. To improve its efficacy, a series of BER derivatives featuring an ester bond linked to an aromatic or heterocyclic aromatic ring at the 9-position were designed and evaluated as effective OfChi-h inhibitors. The most potent compound, compound 19e with a nicotinate group, exhibited a Ki of 0.093 mu M. Molecular docking analysis suggested that the common binding mode of BER derivatives featured a network of pi-pi stacking and electrostatic interactions and that the group at the 9-position enhanced the van der Waals and hydrogen bonding interactions. Administration of the BER derivative 19c to 4th-instar O. furnacalis larvae in an artificial diet led to their impaired growth and metamorphosis. This work provides a new starting point for the modification of BER for use in pest control.
机译：OfChi-h是一种鳞翅目特有的糖苷水解酶家族18（GH18）几丁质酶，来自农业害虫亚洲玉米螟，是一种很有前途的害虫防治分子靶标候选酶。小檗碱（Berberine，BER）是一种传统中药，通过相同的机制与多种糖基水解酶结合，显示出作为农药先导化合物的潜力。在这项工作中，我们发现BER是一种中度OfChi-h抑制剂，Ki为16.1μM。为了提高其功效，我们设计了一系列BER衍生物，这些衍生物具有与9位芳香或杂环芳香环相连的酯键，并评估其作为OfChi-h抑制剂的有效性。最有效的化合物是带有烟酸基团的化合物19e，其Ki为0.093μM。分子对接分析表明，BER衍生物的共同结合模式具有π-π堆积和静电相互作用网络，9位基团增强了范德华和氢键相互作用。在人工饲料中给4龄亚洲褐飞虱幼虫施用BER衍生物19c导致其生长和变态受损。这项工作为改良BER用于害虫防治提供了一个新的起点。

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