Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection fromBaeckea frutescensand Its Biogenetic Origin Insight
Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection fromBaeckea frutescensand Its Biogenetic Origin Insight
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间苯三酚-萜烯加合物系列的发现和仿生合成及其生物起源洞察
DOI：
10.1002/chem.202001111
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发表时间：
2020
期刊：
影响因子：
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通讯作者：
Ye Wen-Cai
中科院分区：
文献类型：
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作者：
Luo Shi-Lin;Hu Li-Jun;Huang Xiao-Jun;Su Jun-Cheng;Shao Xue-Hua;Wang Lei;Xu Han-Hong;Li Chuang-Chuang;Wang Ying;Ye Wen-Cai
间苯三酚-萜类加合物(PTA)由24个分子组成，具有3个骨架。受其生物合成假说的启发，我们通过将稳定的间苯三酚前体还原活化为高活性邻苯二甲酸甲酯(o-QM)中间体，然后进行Diels-Alder环加成，合成了这个PTA系列。我们还首次通过动态核磁共振和高效液相色谱-质谱仪的监测实验，证明了活性基团的生成过程。此外，采集的PTA对小菜蛾具有显著的拒食作用。
A phloroglucinol‐terpene adduct (PTA) collection consisting of twenty‐four molecules featuring three skeletons was discovered fromBaeckea frutescens. Inspired by its biosynthetic hypothesis, we synthesized this PTA collection by reductive activation of stable phloroglucinol precursors into highly reactiveortho‐quinone methide (o‐QM) intermediates and subsequently Diels–Alder cycloaddition. We also demonstrated, for the first time, the generation process of the activeo‐QM by performing dynamic NMR and HPLC‐MS monitoring experiments. Moreover, the PTA collection showed significant antifeedant effect toward thePlutella xylostellalarvae.