Rhein-Amino Acid Ester Conjugates as Potential Antifungal Agents: Synthesis and Biological Evaluation. 2023

Shunshun Chen, and Meimei Wang, and Linhua Yu, and Jinchao Shi, and Yong Zhang, and Yao Tian, and Li Li, and Xiang Zhu, and Junkai Li
Institute of Pesticides, College of Agriculture, Yangtze University, Jingzhou 434025, China.

In the search for crop protectants, amino acid ester conjugates have been widely investigated as potential antifungal agents. In this study, a series of rhein-amino acid ester conjugates were designed and synthesized in good yields, and their structures were confirmed by 1H-NMR, 13C-NMR and HRMS. The bioassay results revealed that most of the conjugates exhibited potent inhibitory activity against R. solani and S. sclerotiorum. In particular, conjugate 3c had the highest antifungal activity against R. solani with an EC50 value of 0.125 mM. For S. sclerotiorum, conjugate 3m showed the highest antifungal activity with an EC50 value of 0.114 mM. Satisfactorily, conjugate 3c exhibited better protective effects than that of the positive control, physcion, against powdery mildew in wheat. This research supports the role of rhein-amino acid ester conjugates as potential antifungal agents for plant fungal diseases.

UI MeSH Term Description Entries
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D005659 Fungicides, Industrial Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. Industrial Fungicides
D000596 Amino Acids Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins. Amino Acid,Acid, Amino,Acids, Amino
D000880 Anthraquinones Compounds based on ANTHRACENES which contain two KETONES in any position. Substitutions can be in any position except on the ketone groups. Anthracenedione,Anthracenediones,Anthranoid,Anthraquinone,Anthraquinone Compound,Anthraquinone Derivative,Dianthraquinones,Dianthrones,Anthranoids,Anthraquinone Compounds,Anthraquinone Derivatives,Compound, Anthraquinone,Derivative, Anthraquinone
D000935 Antifungal Agents Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. Anti-Fungal Agents,Antifungal Agent,Fungicides, Therapeutic,Antibiotics, Antifungal,Therapeutic Fungicides,Agent, Antifungal,Anti Fungal Agents,Antifungal Antibiotics
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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