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Food microbiology. 2025 Sep:130:104779. doi: 10.1016/j.fm.2025.104779 Q14.52024

N-Acetyl-O-methyl-tyrosine from Bipolaris bicolor: A novel fungicide for postharvest anthracnose and citrus preservation

来自Bipolaris bicolor的N-乙酰基-O-甲基酪氨酸：一种用于采后炭疽病和柑橘保鲜的新颖杀菌剂 翻译改进

Zikui Zheng  1, Yicheng Xu  2, Hui-Xi Zou  3, Xiufeng Yan  4, Peng Cao  5

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作者单位

  • 1 National and Local Joint Engineering Research Center of Ecological Treatment Technology for Urban Water Pollution, Zhejiang Provincial Key Laboratory for Water Environment and Marine Biological Resources Protection, College of Life and Environmental Science, Wenzhou University, Wenzhou, 325035, China; School of Environmental Studies, China University of Geosciences, Wuhan, 430074, China.
  • 2 National and Local Joint Engineering Research Center of Ecological Treatment Technology for Urban Water Pollution, Zhejiang Provincial Key Laboratory for Water Environment and Marine Biological Resources Protection, College of Life and Environmental Science, Wenzhou University, Wenzhou, 325035, China; State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Center for Biomanufacturing, East China University of Science and Technology, Shanghai, 200237, China.
  • 3 National and Local Joint Engineering Research Center of Ecological Treatment Technology for Urban Water Pollution, Zhejiang Provincial Key Laboratory for Water Environment and Marine Biological Resources Protection, College of Life and Environmental Science, Wenzhou University, Wenzhou, 325035, China.
  • 4 National and Local Joint Engineering Research Center of Ecological Treatment Technology for Urban Water Pollution, Zhejiang Provincial Key Laboratory for Water Environment and Marine Biological Resources Protection, College of Life and Environmental Science, Wenzhou University, Wenzhou, 325035, China; Institute for Eco-environmental Research of Sanyang Wetland, Wenzhou University, Ouhai Road, Wenzhou, 325014, China. Electronic address: yanxiufeng@wzu.edu.cn.
  • 5 National and Local Joint Engineering Research Center of Ecological Treatment Technology for Urban Water Pollution, Zhejiang Provincial Key Laboratory for Water Environment and Marine Biological Resources Protection, College of Life and Environmental Science, Wenzhou University, Wenzhou, 325035, China; Institute for Eco-environmental Research of Sanyang Wetland, Wenzhou University, Ouhai Road, Wenzhou, 325014, China. Electronic address: caopeng@wzu.edu.cn.

    • DOI: 10.1016/j.fm.2025.104779 PMID: 40210402

    摘要 中英对照阅读

    The necessity for safe and effective alternatives to conventional chemical fungicides is underscored by postharvest citrus fruit losses due to anthracnose, caused by Colletotrichum gloeosporioides. In this context, the biocontrol fungus Bipolaris bicolor WZU-HOG4, isolated from Ougan pericarp, was identified as possessing antimicrobial activity. Through bioassay-guided fractionation and subsequent metabolite profiling, N-Acetyl-O-methyl-tyrosine was identified as the active antifungal compound using NMR and HRESIMS. This compound demonstrated significant inhibitory effects against C. gloeosporioides and other pathogens, exhibiting a relatively broad-spectrum antifungal activity. Molecular docking analysis indicated that N-acetyl-O-methyl-tyrosine binds to tyrosinase with greater affinity than Vitamin C, effectively inhibiting its activity. Furthermore, Ougan fruits treated with the compound exhibited increased activities of antioxidant enzymes SOD, POD, and CAT, reduced MDA content, and decreased oxidative stress during storage. Cytotoxicity assays conducted on HEK-293 cells confirmed the compound's safety at the tested concentrations. N-acetyl-O-methyl-tyrosine emerges as a promising natural antifungal and tyrosinase inhibitor for citrus postharvest preservation, providing a safe alternative to chemical preservatives for extending shelf life.

    Keywords: Antifungal activity; Bipolaris bicolor WZU-HOG4; Citrus preservation; N-Acetyl-O-methyl-tyrosine; Postharvest anthracnose.

    Keywords：N-Acetyl-O-methyl-tyrosine; Bipolaris bicolor; Fungicide; Postharvest anthracnose; Citrus preservation

    由于由 Colletotrichum gloeosporioides 引起的柑橘采后炭疽病造成的损失，开发安全有效的传统化学杀菌剂替代品的需求变得尤为重要。在这种背景下，从瓯柑果皮中分离出的生物控制真菌 Bipolaris bicolor WZU-HOG4 被鉴定为具有抗菌活性。通过生化分析引导的分馏和随后的代谢物谱分析，并使用 NMR 和 HRESIMS 确定了 N-乙酰基-O-甲基酪氨酸作为有效的抗真菌化合物。该化合物对 C. gloeosporioides 以及其他病原体表现出显著的抑制作用，显示出相对较广谱的抗真菌活性。分子对接分析表明，N-乙酰基-O-甲基酪氨酸与酪氨酸酶的结合亲和力大于维生素C，有效地抑制其活性。此外，在储存期间用该化合物处理瓯柑果实显示抗氧化酶 SOD、POD 和 CAT 的活性增加，MDA 含量降低以及氧化应激减少。在 HEK-293 细胞上进行的细胞毒性试验确认了测试浓度下该化合物的安全性。N-乙酰基-O-甲基酪氨酸作为柑橘采后保存的一种有前途的天然抗真菌和酪氨酸酶抑制剂，为化学保鲜剂提供了一种安全替代品，可以延长保质期。

    关键词：

    抗真菌活性；Bipolaris bicolor WZU-HOG4；柑橘保存；N-乙酰基-O-甲基酪氨酸；采后炭疽病。

    关键词：N-乙酰-O-甲基酪氨酸; 二型双极链格孢; 杀菌剂; 采后炭疽病; 柑橘保鲜

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    期刊名：Food microbiology

    缩写：FOOD MICROBIOL

    ISSN：0740-0020

    e-ISSN：1095-9998

    IF/分区：4.5/Q1

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    N-Acetyl-O-methyl-tyrosine from Bipolaris bicolor: A novel fungicide for postharvest anthracnose and citrus preservation