Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection fromBaeckea frutescensand Its Biogenetic Origin Insight
文献类型： 外文期刊
作者： Luo, Shi-Lin 1 ; Hu, Li-Jun 1 ; Huang, Xiao-Jun 1 ; Su, Jun-Cheng 1 ; Shao, Xue-Hua 4 ; Wang, Lei 1 ; Xu, Han-Hong 5 ; Li 1 ;
作者机构： 1.Jinan Univ, Coll Pharm, Inst Tradit Chinese Med & Nat Prod, Guangzhou 510632, Peoples R China
2.Jinan Univ, Guangdong Prov Key Lab Pharmacodynam Constituents, Guangzhou 510632, Peoples R China
3.South Univ Sci & Technol China, Dept Chem, Shenzhen 518055, Peoples R China
4.Guangdong Acad Agr Sci, Inst Fruit Tree Res, Guangzhou 510640, Peoples R China
5.South China Agr Univ, State Key Lab Conservat & Utilizat Subtrop Agrobi, Guangzhou 510642, Peoples R China
关键词： Baeckea frutescensL; biomimetic synthesis; biosynthetic pathways; natural products; phloroglucinol-terpene adduct
期刊名称：CHEMISTRY-A EUROPEAN JOURNAL （ 影响因子：5.236； 五年影响因子：4.843 ）
ISSN： 0947-6539
年卷期： 2020 年 26 卷 49 期
页码：
收录情况： SCI
摘要： 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.
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