Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Chengwei Xie,Tingting Liu,Wei Xue,Shijun Su,Ming He,Xuemei Tang,Liwei Liu,Qing Zhou,Feng Peng

doi:10.1007/s00706-021-02739-1

Chengwei Xie, Tingting Liu + Show 7 more

Open Access

https://doi.org/10.1007/s00706-021-02739-1

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Abstract

A series of myricetin derivatives containing sulfonate groups were designed and synthesized. Preliminary antibacterial activity showed that most of the target compounds exhibited significant biological activities against Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the EC50 value of compound 3e was 13.76 μg/cm3 against Xac, which was better than commercial reagents bismerthiazol (50.32 µg/cm3) and thiodiazole copper. (83.27 µg/cm3), and the EC50 value of compound 3j was 11.92 μg/cm3 against Xoo in vitro, The result was better than that of bismerthiazol (72.08 µg/cm3) and thiodiazole copper (99.26 µg/cm3). Compound 3j displayed the better in vivo activity against rice bacterial leaf blight than bismerthiazol and thiodiazole copper. Meanwhile, the antibacterial mechanism of compounds 3e and 3j was studied by scanning electron microscope (SEM). These results suggested that myricetin derivatives containing sulfonate can be considered as a new antibacterial reagents.Graphic abstract

Highlights

Plant bacterial diseases are frequently encountered in agricultural production and difficult to manage, such as citrus canker, tobacco bacterial wilt and rice bacterial leaf blight, which can be caused by Xanthomonas axonopodis pv
In the 1H NMR spectrum, the multiple signal δ = 6.57–7.57 ppm demonstrated the presence of aromatic ring protons, the singlet signal of 3.6–4.0 ppm belonged to -OCH3 on myricetin, and the singlet signal of 2.34 ppm indicates the presence of –CH3 group
The results indicated that compounds 3e, 3i, 3k, 3n, and 3o exhibited prominent antibacterial activity against Xanthomonas axonopodis pv. Citri (Xac) with EC50 values of 13.72, 23.19, 19.81, 16.89, and 19.19 μg/cm3 (Table 3), which were superior to BT (50.32 μg/cm3) and TC (83.27 μg/cm3)

Summary

Introduction

Plant bacterial diseases are frequently encountered in agricultural production and difficult to manage, such as citrus canker, tobacco bacterial wilt and rice bacterial leaf blight, which can be caused by Xanthomonas axonopodis pv. Sulfonate derivatives, owing to physicochemical properties, have a strong affinity for lipid phases and can cross the cuticle membrane to bind to target sites [23], and compounds containing aryl sulfonate moieties have received considerable attention due to extensive biological activities, and it has been proven to possess antiviral [24, 25], antibacterial [26,27,28], insecticidal [29, 30], anticancer [31, 32], and other biological activity [33] They were widely used in agricultural industries, medicine researches and other fields. Scheme 1 antibacterial activity evaluation of myricetin derivatives containing sulfonate moiety

Results and discussion

Conclusions

Evaluation of the antibacterial activity