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从天然产物衍生物到六棱柱超分子:强大的生物膜瓦解作用、增强的叶面亲和力以及对番茄溃疡病的有效治理

From Natural Product Derivative to Hexagonal Prism Supermolecule: Potent Biofilm Disintegration, Enhanced Foliar Affinity, and Effective Management of Tomato Bacterial Canker.

作者信息

Chen Xue, Yang Run, Liu Kongjun, Liu Min, Shi Qingchuan, Yang Jinghan, Hao Gefei, Luo Laixin, Du Fengpei, Wang Peiyi

机构信息

State National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals of Guizhou University, Guiyang, 550025, China.

Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, 563000, China.

出版信息

Angew Chem Int Ed Engl. 2025 Feb 17;64(8):e202416079. doi: 10.1002/anie.202416079. Epub 2025 Jan 28.

DOI:10.1002/anie.202416079
PMID:39825489
Abstract

Clavibacter michiganensis (Cmm), designated as an A2 quarantine pest by the European and Mediterranean Plant Protection Organization (EPPO), incites bacterial canker of tomato, which presently eludes rapid and effective control methodologies. Dense biofilms formed by Cmm shield internal bacteria from host immune defenses and obstruct the ingress of agrochemicals. Even when agrochemicals disintegrate biofilms, splashing and bouncing during application disperse active ingredients away from target sites. Herein, we present a supramolecular strategy to fabricate a hexagonal prism-shaped material, BPGA@CB[8], assembled from an 18β-glycyrrhetinic acid derivative (PBGA) and host molecule-cucurbit[8]uril (CB[8]) via host-guest recognition. This positively charged material manifests multifaceted functionalities, notably the ability to surmount biofilm barriers, annihilate the encased pathogenic bacteria, and enhance foliar affinity of droplets. The strong in vitro potency and effective deposition of BPGA@CB[8] foster optimal conditions for robust in vivo efficacy, demonstrating superior protective and curative activities (56.9 %/53.4 %) against canker of tomato at a low-dose of 100 μg⋅mL compared to BPGA (44.6 %/42.2 %), kasugamycin (30.1 %/28.4 %), and thiodiazole copper (35.4 %/31.0 %). This supramolecular material, based on natural product derivatives, provides a potent treatment for high-risk canker of tomato, and exemplifies the utility of supramolecular strategies in optimizing the attributes of natural products for managing plant bacterial diseases.

摘要

密执安棒形杆菌(Cmm)被欧洲和地中海植物保护组织(EPPO)指定为A2类检疫性有害生物,它会引发番茄细菌性溃疡病,目前尚无快速有效的防治方法。Cmm形成的致密生物膜可保护内部细菌免受宿主免疫防御,并阻碍农用化学品的进入。即使农用化学品能分解生物膜,在施用过程中的飞溅和反弹也会使活性成分从目标部位分散开。在此,我们提出一种超分子策略,以制备一种六棱柱形材料BPGA@CB[8],它由18β-甘草次酸衍生物(PBGA)和主体分子葫芦[8]脲(CB[8])通过主客体识别组装而成。这种带正电荷的材料具有多方面的功能,特别是能够克服生物膜屏障、消灭被包裹的病原菌,并增强液滴与叶片的亲和力。BPGA@CB[8]强大的体外效力和有效沉积为其在体内发挥强大功效创造了最佳条件,与BPGA(44.6%/42.2%)、春雷霉素(30.1%/28.4%)和噻菌铜(35.4%/31.0%)相比,在低剂量100μg·mL时对番茄溃疡病表现出卓越的保护和治疗活性(56.9%/53.4%)。这种基于天然产物衍生物的超分子材料为番茄高风险溃疡病提供了有效的治疗方法,并例证了超分子策略在优化天然产物属性以管理植物细菌病害方面的效用。

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