Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine
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ORIGINAL PAPER
Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine Jun He1 · Xue‑Mei Tang1 · Ting‑Ting Liu1 · Feng Peng1 · Qing Zhou1 · Li‑Wei Liu1 · Ming He1 · Wei Xue1 Received: 10 June 2020 / Accepted: 15 September 2020 © The Author(s) 2020
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. Keywords Myricetin derivative · Sulfonylpiperazine · Antibacterial activity · Concentration for 50% of maximal effect · Scanning electron microscope
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). Since the earliest fungicide bordeaux liquid, a lot of agricultural fungicides have been developed successively. With the development of chemistry, new types of nano-antibacterial agents have also come into the sight of chemists (Khatoon et al. 2017, 2018). Until today, there have been many commercial antibacterial agents with good activity, such as bismerthiazol and thiodiazole-copper etc. However, with the increase in the Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-020-01363-3) contains supplementary material, which is available to authorized users. * Wei Xue [email protected] 1
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China
use of traditional fungicides, the resistance of plant bacteria to them has gradually increases (Yan et al. 2016; Jiang et al. 2020a, b). Therefore, the development of new antibacterial agents is of great significance. Flavonoids are widely existed in plants in nature, and belong to the secondary metabolites of plants (Manthey and Guthrie 2002). It plays an important role in plant growth, development, flowering, fruiting, antibacterial and disease prevention. Moreover, many studies in recent y
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