Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine

Jun He,Xue-Mei Tang,Feng Peng,Wei Xue,Qing Zhou,Ming He,Li-Wei Liu,Ting-Ting Liu

doi:10.1007/s11696-020-01363-3

Abstract

Myricetin derivatives containing sulfonylpiperazine were synthesized and their structures were confirmed by NMR and HRMS. The antibacterial activity results indicated that some compounds showed good antibacterial activity against Xanthomonas oryzaepv. oryzae (Xoo), Xanthomonas axonopodispv. citri (Xac) and Ralstonia solanacearum (Rs). Among them, compounds 4m and 4p revealed excellent antibacterial activities against Rs with a concentration for 50% of maximal effect (EC50) value of 4 and 4 μg/mL, which were better than the control drugs bismerthiazol (13 μg/mL) and thiodiazole-copper (185 μg/mL). As observed using scanning electron microscope (SEM), these compounds act by causing folding and deformation of the bacterial surface, resulting in incomplete bacterial structure, so as to achieve the goal of bacteriostasis. The myricetin derivatives synthesized are expected to guide the research direction of new antibacterial agents.

Highlights

Plant diseases have always been a headache in agricultural production
Twenty-five myricetin derivative containing sulfonylpiperazine were obtained in this study, all their structures were identified via 1H nuclear magnetic resonance (NMR), 13C NMR, 19F NMR and high resolution mass spectrometry (HRMS)
In the 1H NMR spectrum, multiplet signals at δ 7.68–6.28 ppm revealed the presence of aromatic nuclei, and a triplet peak at δ 3.91–3.94 ppm indicated the presence of O–CH2–C group

Summary

Introduction

Plant diseases have always been a headache in agricultural production. The plant bacterial diseases are extremely difficult to control in agricultural production, such as rice bacterial blight, tobacco bacterial wilt, citrus canker and so on (Zou et al 2011; Li et al 2017). The bacteriostatic activity of the compounds were measured by turbidimetric method (Zhong et al 2017; Li et al 2013), using Xac, Xoo and Rs as test strains, while using the commercial antibacterial agents bismerthiazol and thiodiazolecopper as control drugs.

Results

Conclusion