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Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection from Baeckea frutescens and Its Biogenetic Origin Insight |
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| Authors: | Dr Shi-Lin Luo Dr Li-Jun Hu Dr Xiao-Jun Huang Dr Jun-Cheng Su Dr Xue-Hua Shao Dr Lei Wang Prof Dr Han-Hong Xu Prof Dr Chuang-Chuang Li Prof Dr Ying Wang Prof Dr Wen-Cai Ye |
| Institution: | 1. Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China
Guangdong Province Key Laboratory of Pharmacodynamic Constituents of, TCM and New Drugs Research, Jinan University, Guangzhou, 510632 P. R. China These authors contributed equally to this work.;2. Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China;3. Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, 510632 P. R. China Guangdong Province Key Laboratory of Pharmacodynamic Constituents of, TCM and New Drugs Research, Jinan University, Guangzhou, 510632 P. R. China;4. Institute of Fruit Tree Research, Guangdong Academy of, Agricultural Sciences, Guangzhou, 510640 P. R. China;5. State Key Laboratory for Conservation and Utilization of, Subtropical Agro-bioresources, South China Agricultural University, Guangzhou, 510642 P. R. China;6. Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518055 P. R. China |
| 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. |
| Keywords: | Baeckea frutescens L biomimetic synthesis biosynthetic pathways natural products phloroglucinol-terpene adduct |