Semisynthesis and Pesticidal Activities of Derivatives of the Diterpenoid Andrographolide and Investigation on the Stress Response of Aphis citricola Van der Goot (Homoptera: Aphididae),Journal of Agricultural and Food Chemistry

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Semisynthesis and Pesticidal Activities of Derivatives of the Diterpenoid Andrographolide and Investigation on the Stress Response of Aphis citricola Van der Goot (Homoptera: Aphididae)
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-03-25 , DOI: 10.1021/acs.jafc.9b08242
Meng Hao ₁ , Zhiqiang Sun ₁ , Jianwei Xu ₁ , Min Lv ₁ , Hui Xu _{1,

2}

Affiliation

To discover natural-product-based pesticides, 7β-oxycarbonylandrographolide derivatives were stereoselectively constructed from a labdane diterpenoid andrographolide. Among them, 2′-(n)Pr-1′,3′-dioxin-7β-oxy(m-Cl)benzoylandrographolide (IIc), 2′-(n)Pr-1′,3′-dioxin-7β-oxyacetylandrographolide (IIf), 2′-(p-Me)Ph-1′,3′-dioxin-7β-oxy(o-Cl)benzoylandrographolide (Vb), and 2′-(p-Me)Ph-1′,3′-dioxin-7β-oxy(m-Cl)benzoylandrographolide (Vc) against Mythimna separata displayed the most promising growth inhibitory activity; 2′-(n)Pr-1′,3′-dioxin-7β-oxy(o-Cl)benzoylandrographolide (IIb: LC₅₀ = 0.406 mg/mL) and IIc (LC₅₀ = 0.415 mg/mL) exhibited the most pronounced acaricidal activity (andrographolide; LC₅₀: 5.106 mg/mL) and good control effects against Tetranychus cinnabarinus; compounds Ic, IIe, and Va–c (LD₅₀ = 0.035–0.039 μg/nymph) showed potent aphicidal activity (andrographolide: LD₅₀ = 0.178 μg/nymph), and compounds IIe and Vb showed good control effects against Aphis citricola. Moreover, it was found that Hsp70 of A. citricola was an important gene involved in stress response to andrographolide and its derivatives.

中文翻译：

二萜类穿心莲内酯衍生物的半合成和杀虫活性及柠檬蚜（Homooptera：Aphididae）的胁迫响应研究

为了发现基于天然产物的农药，从拉丹烷二萜类穿心莲内酯立体选择性地构建了7β-氧羰基穿心莲内酯衍生物。其中，2'-（n）Pr-1'，3'-二恶英-7β-氧基（m -Cl）苯并穿心莲内酯（IIc），2'-（n）Pr-1'，3'-二恶英-7β-氧乙酰基穿心莲内酯（IIf），2'-（p -Me）Ph-1'，3'-二恶英7β-氧基（o -Cl）苯并穿心莲内酯（Vb）和2'-（p- Me）Ph-1'， 3'-二恶英-7β-氧基（m -Cl）苯并紫菜内酯（Vc）对分离的Mythimna separata表现出最有希望的生长抑制活性。2′-（n）Pr-1'，3'-二恶英-7β-氧基（邻-Cl）苯并穿心莲内酯（IIb：LC ₅₀ = 0.406 mg / mL）和IIc（LC ₅₀ = 0.415 mg / mL）表现出最明显的杀螨活性穿心莲内酯； LC ₅₀：5.106 mg / mL），对朱砂叶螨有良好的防治作用；化合物Ic，IIe和Va – c（LD ₅₀ = 0.035–0.039μg/ nymph）显示出有效的杀蚜活性（穿心莲内酯：LD ₅₀ = 0.178μg / nymph），化合物IIe和Vb表现出对柠檬蚜的良好控制效果。此外，人们发现，热休克蛋白70的A.蚜是参与胁迫响应于穿心莲内酯和其衍生物的重要基因。

更新日期：2020-03-26

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