AI Article Synopsis
- A collection of twenty-four phloroglucinol-terpene adducts (PTAs) was discovered from the plant Baeckea frutescens, featuring three different molecular structures.
- The synthesis of these PTAs involved a method that activates stable phloroglucinol precursors into highly reactive intermediates, followed by a cycloaddition reaction.
- The study also revealed the generation process of these intermediates using advanced monitoring techniques and found that the PTA collection effectively deterred feeding in Plutella xylostella larvae.
Article Abstract
A phloroglucinol-terpene adduct (PTA) collection consisting of twenty-four molecules featuring three skeletons was discovered from Baeckea frutescens. Inspired by its biosynthetic hypothesis, we synthesized this PTA collection by reductive activation of stable phloroglucinol precursors into highly reactive ortho-quinone methide (o-QM) intermediates and subsequently Diels-Alder cycloaddition. We also demonstrated, for the first time, the generation process of the active o-QM by performing dynamic NMR and HPLC-MS monitoring experiments. Moreover, the PTA collection showed significant antifeedant effect toward the Plutella xylostella larvae.
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| http://dx.doi.org/10.1002/chem.202001111 | DOI Listing |
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