Mycotoxins from Fusarium proliferatum : new inhibitors of papain-like cysteine proteases
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ENVIRONMENTAL MICROBIOLOGY - RESEARCH PAPER
Mycotoxins from Fusarium proliferatum: new inhibitors of papain-like cysteine proteases Taynara Lopes Silva 1 & Leonardo Toffano 2 & João Batista Fernandes 1 & Maria Fátima das Graças Fernandes da Silva 1 & Lorena Ramos Freitas de Sousa 3 Paulo Cezar Vieira 1,4
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Received: 10 December 2019 / Accepted: 6 March 2020 # Sociedade Brasileira de Microbiologia 2020
Abstract Papain-like cysteine proteases (PLCPs) in plants are essential to prevent phytopathogen invasion. In order to search for cysteine protease inhibitors and to investigate compounds that could be associated to pineapple Fusarium disease, a chemistry investigation was performed on Fusarium proliferatum isolated from Ananas comosus (pineapple) and cultivated in Czapek medium. From F. proliferatum extracts, nine secondary metabolites were isolated and characterized by nuclear magnetic resonance spectroscopy and mass spectrometry experiments: beauvericin (1), fusaric acid (2), N-ethyl-3-phenylacetamide (3), Nacetyltryptamine (4), cyclo(L-Val-L-Pro) cyclodipeptide (5), cyclo(L-Leu-L-Pro) cyclodipeptide (6), cyclo(L-Leu-L-Pro) diketopiperazine (7), 2,4-dihydroxypyrimidine (8), and 1H-indole-3-carbaldehyde (9). Compounds 1, 3, and 6 showed significant inhibition of papain, with IC50 values of 25.3 ± 1.9, 39.4 ± 2.5, and 7.4 ± 0.5 μM, respectively. Compound 1 also showed significant inhibition against human cathepsins V and B with IC50 of 46.0 ± 3.0 and 6.8 ± 0.7 μM, respectively. The inhibition of papain by mycotoxins (fusaric acid and beauvericin) may indicate a mechanism of Fusarium in the roles of infection process. Keywords Cathepsin . Cysteine peptidases . Fusaric acid . Fusarium proliferatum, papain
Introduction Protease inhibitors in plants are key factors for defense and promotion of balance of the ecological system interaction between plants, microorganisms, and insects [1, 2]. Most
Responsible Editor: Luis Augusto Nero. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s42770-020-00256-7) contains supplementary material, which is available to authorized users. * Paulo Cezar Vieira [email protected] 1
Department of Chemistry, Federal University of São Carlos, São Carlos, SP 13565-905, Brazil
2
Department of Agronomy, Brasil University, Campus Descalvado, Descalvado, SP 13565-905, Brazil
3
Special Academic Unit of Chemistry, Federal University of Goiás, Catalão regional, Catalão, GO 75704-020, Brazil
4
School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Ribeirão Preto, SP 14040-903, Brazil
proteolytic enzymes are papain-like cysteine proteases (PLCPs), and they play an important role in plant immunity preventing pathogen invaders [3]. In humans, PLCPs are known as cathepsins, and the upregulation of these enzymes in the organism is related to pathologic disorders (osteoporosis, arthritis, cancer, metastasis, etc.) [4, 5]. Plants’ PLCPs belong to protease family C1A of clan CA, which catalytic triad contains the amino acids C
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