Modular and scalable synthesis of nematode pheromone ascarosides: implications in eliciting plant defense response.,Organic & Biomolecular Chemistry

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Modular and scalable synthesis of nematode pheromone ascarosides: implications in eliciting plant defense response.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-06-17 , DOI: 10.1039/d0ob00652a
Shuai Ning ₁ , Lei Zhang ₂ , Jinjin Ma ₁ , Lan Chen ₁ , Guangyao Zeng ₁ , Chao Yang ₂ , Yingjun Zhou ₁ , Xiaoli Guo ₂ , Xu Deng ₁

Affiliation

A highly efficient and modular synthesis of nematode pheromone ascarosides was developed, which highlights a 4-step scalable synthesis of the common intermediate 10 in 23% yield from commercially available L-rhamnose by using orthoesterification/benzylation/orthoester rearrangement as the key step. Six diverse ascarosides were synthesized accordingly. Notably, biological investigations revealed that ascr#1 and ascr#18 treatment resulted in enhanced callose accumulation in Arabidopsis leaves. And ascr#18 also increased the expression of defense-related genes such as PR1, PDF1.2, LOX2 and AOS, which might contribute to the enhanced plant defense responses. This study not only allows a facile access to 1-O, 2-O, and 4-O substituted ascarosides, but also provides valuable insights into their biological activities in inducing plant defense response, as well as their mode of action.

中文翻译：

线虫信息素a虫苷的模块化和可扩展合成：引发植物防御反应的含义。

已开发出一种高效，模块化的线虫信息素a虫苷合成方法，该方法突出了通过使用原酸酯化/苄基化/原酸酯重排作为关键步骤，可从市售L-鼠李糖以23％的产率对普通中间体10进行4步可扩展合成的过程。相应地合成了六种不同的scar螨。值得注意的是，生物学研究表明，ascr＃1和ascr＃18处理导致拟南芥叶片中愈伤组织的积累增加。ascr＃18还增加了与防御相关的基因（如PR1，PDF1.2，LOX2和AOS）的表达，这可能有助于增强植物的防御反应。这项研究不仅允许轻松访问1- O，2- O，4- O取代的scar虫甙，还提供了有关其在诱导植物防御反应中的生物学活性及其作用方式的宝贵见解。

更新日期：2020-07-08

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