Design, synthesis and antimicrobial activity of novel berberine derivatives

• Published in: Pest management science Vol. 80; no. 12; pp. 6344 - 6355
• Main Authors: Zhang, Bao‐Qi, Li, Fu‐Ping, An, Jun‐Xia, Ma, Li, Jin, Ya‐Rui, Zhang, Zhi‐Jun, Qin, Lu‐Lu, Wang, Deng‐Tuo, Jing, Cheng‐Xin, Chen, Gui‐Sha, Mou, Guo‐Liang, Liu, Ying‐Qian
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.12.2024; Wiley Subscription Services, Inc
• Subjects: 3D‐QSAR; Agrochemicals; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antifungal activity; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; antifungal properties; Antimicrobial activity; Antimicrobial agents; Ascomycota - drug effects; Bacteria; Berberine; Berberine - analogs & derivatives; Berberine - chemical synthesis; Berberine - chemistry; Berberine - pharmacology; Bioassays; Botrytis - drug effects; Botrytis cinerea; Chemical activity; Chemical synthesis; Drug Design; Fungi; Fungicides; Fungicides, Industrial - chemical synthesis; Fungicides, Industrial - chemistry; Fungicides, Industrial - pharmacology; Germination; In vivo methods and tests; Lead compounds; Leaf blight; Microbial Sensitivity Tests; pest management; Plant Diseases - microbiology; Plant Diseases - prevention & control; Quantitative Structure-Activity Relationship; rice; Sclerotinia sclerotiorum; Spore germination; spore germination test; structural modification; Structure-activity relationships; Xanthomonas - drug effects; Xanthomonas campestris; Xanthomonas campestris - drug effects; Xanthomonas oryzae pv. oryzae; Berberine; spore germination test; antimicrobial activity; 3D‐QSAR; structural modification
• ISSN: 1526-498X; 1526-4998; 1526-4998
• DOI: 10.1002/ps.8363

BACKGROUND The threats to the safety of humans and the environment and the resistance of agricultural chemicals to plant pathogenic fungi and bacteria highlight an urgent need to find safe and efficient alternatives to chemical fungicides and bactericides. In this study, a series of Berberine (BBR) derivatives were designed, synthesized and evaluated for in vitro and in vivo antimicrobial activity against plant pathogenic fungi and bacteria. RESULTS Bioassay results indicated that compounds A11, A14, A20, A21, A22, A25, A26, E1, E2, E3, Z1 and Z2 showed high inhibitory activity against Sclerotinia sclerotiorum and Botrytis cinerea. Especially, A25 showed a broad spectrum and the highest antifungal activity among these compounds. Its EC50 value against Botrytis cinerea was 1.34 μg mL−1. Compound E6 possessed high inhibitory activity against Xanthomonas oryzae and Xanthomonas Campestris, with MIC90 values of 3.12 μg mL−1 and 1.56 μg mL−1. A Topomer CoMFA model was generated for 3D‐QSAR studies based on anti‐B. cinerea effects, with high predictive accuracy, showed that the addition of an appropriate substituent group at the para‐position of benzyl of BBR derivatives could effectively improve the anti‐B. cinerea activity. In addition, compound A25 could significantly inhibit the spore germination of Botrytis cinerea at low concentration, and compound F4 exhibited remarkable curative and protective efficiencies on rice bacterial leaf blight. CONCLUSION This study indicates that the BBR derivatives are hopeful for further exploration as the lead compound with novel antimicrobial agents. © 2024 Society of Chemical Industry. In this study, a series of BBR derivatives were synthesized with significant antimicrobial activity against agricultural pathogens.