Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection fromBaeckea frutescensand Its Biogenetic Origin Insight

Luo, Shi-Lin1,2; Hu, Li-Jun1,2; Huang, Xiao-Jun1,2; Su, Jun-Cheng1,2; Shao, Xue-Hua4; Wang, Lei1,2; Xu, Han-Hong5; Li, Chuang-Chuang3; Wang, Ying1,2; Ye, Wen-Cai1,2

2020-07-28

10.1002/chem.202001111

CHEMISTRY-A EUROPEAN JOURNAL   影响因子和分区

0947-6539

1521-3765

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.

Baeckea frutescensL biomimetic synthesis biosynthetic pathways natural products phloroglucinol-terpene adduct

SCI ; EI

英语

通讯

National Key R&D Program of China[2017YFC1703800] ; National Mega-Project for Innovative Drugs[2019ZX09735002] ; National Natural Science Foundation of China[81630095][81622045][81903493] ; Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program[2017BT01Y036] ; Natural Science Foundation of Guangdong Province[2019A1515011478]

Chemistry

Chemistry, Multidisciplinary

WOS:000553008700001

WILEY-V C H VERLAG GMBH

20203108999326

Quinone ; Biosynthesis

Biotechnology:461.8 ; Energy Storage:525.7 ; Biochemistry:801.2 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

CHEMISTRY

Web of Science

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

Luo, Shi-Lin,Hu, Li-Jun,Huang, Xiao-Jun,et al. Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection fromBaeckea frutescensand Its Biogenetic Origin Insight[J]. CHEMISTRY-A EUROPEAN JOURNAL,2020,26(49):11104-11108.

Luo, Shi-Lin.,Hu, Li-Jun.,Huang, Xiao-Jun.,Su, Jun-Cheng.,Shao, Xue-Hua.,...&Ye, Wen-Cai.(2020).Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection fromBaeckea frutescensand Its Biogenetic Origin Insight.CHEMISTRY-A EUROPEAN JOURNAL,26(49),11104-11108.

Luo, Shi-Lin,et al."Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection fromBaeckea frutescensand Its Biogenetic Origin Insight".CHEMISTRY-A EUROPEAN JOURNAL 26.49(2020):11104-11108.