Antifungal Activity against Botrytis cinerea of 2,6-Dimethoxy-4-(phenylimino)cyclohexa-2,5-dienone Derivatives

Castro, Paulo de Tarso Oliveira e; Mendoza, Leonora; Vásquez, Claudio C.; Pereira, Paz Cornejo; Navarro, Fernanda Keley Silva Pereira; Lizama, Karin; Santander, Rocío; Cotoras, Milena

doi:10.3390/molecules24040706

Cited by 10 publications

(9 citation statements)

References 45 publications

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“…The products possessed a higher efficacy against Botrytis cinerea than the parent substances and may be used as pesticides in agriculture. The antifungal activity of the dimers is probably based on a destructive effect on the fungal cell wall possibly caused by the interaction with enzymes involved in chitin and glucan synthesis (Mendoza et al 2016 ; Castro et al 2019 ).…”

Section: Further Compoundsmentioning

confidence: 99%

“…An increase of the catechol concentration from 1 to 1.25 mmol compared to the reaction partner 2-mercaptobenzothiazole resulted in a 16% higher yield of the hybrid dimer (Abdel-Mohsen et al 2014 ). The laccase-mediated synthesis of dimers consisting of syringic acid and different anilines was most effective for an equal amount of the reactants (0.1 mmol) than with an excess of one of the two partners (Castro et al 2019 ). But, in case of a targeted synthesis of trimers consisting e.g.…”

Section: Further Compoundsmentioning

confidence: 99%

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Potential of the enzyme laccase for the synthesis and derivatization of antimicrobial compounds

Hahn

2023

World J Microbiol Biotechnol

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Laccases [E.C. 1.10.3.2, benzenediol:dioxygen oxidoreductase] can oxidize phenolic substances, e.g. di- and polyphenols, hydroxylated biaryls, aminophenols or aryldiamines. This large substrate spectrum is the basis for various reaction possibilities, which include depolymerization and polymerization reactions, but also the coupling of different substance classes. To catalyze these reactions, laccases demand only atmospheric oxygen and no depletive cofactors. The utilization of mild and environmentally friendly reaction conditions such as room temperature, atmospheric pressure, and the avoidance of organic solvents makes the laccase-mediated reaction a valuable tool in green chemistry for the synthesis of biologically active compounds such as antimicrobial substances. In particular, the production of novel antibiotics becomes vital due to the evolution of antibiotic resistances amongst bacteria and fungi. Therefore, laccase-mediated homo- and heteromolecular coupling reactions result in derivatized or newly synthesized antibiotics. The coupling or derivatization of biologically active compounds or its basic structures may allow the development of novel pharmaceuticals, as well as the improvement of efficacy or tolerability of an already applied drug. Furthermore, by the laccase-mediated coupling of two different active substances a synergistic effect may be possible. However, the coupling of compounds that have no described efficacy can lead to biologically active substances by means of laccase. The review summarizes laccase-mediated reactions for the synthesis of antimicrobial compounds valuable for medical purposes. In particular, reactions with two different reaction partners were shown in detail. In addition, studies with in vitro and in vivo experimental data for the confirmation of the antibacterial and/or antifungal efficacy of the products, synthesized with laccase, were of special interest. Analyses of the structure–activity relationship confirm the great potential of the novel compounds. These substances may represent not only a value for pharmaceutical and chemical industry, but also for other industries due to a possible functionalization of surfaces such as wood or textiles.

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Section: Further Compoundsmentioning

confidence: 99%

Section: Further Compoundsmentioning

confidence: 99%

Potential of the enzyme laccase for the synthesis and derivatization of antimicrobial compounds

Hahn

2023

World J Microbiol Biotechnol

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“…Namely, due to their ability to transform a wide range of organic compounds, laccases have been reported to catalyze the synthesis of a number of biologically active molecules. Among recent reports, a set of 2,6-dimethoxy-4-(phenylimino)cyclohexa-2,5-dienones was synthesized by T. versicolor laccase-catalyzed oxidative coupling, and their activity against Botrytis cinerea phytopathogen was assessed [100]. Likewise, a series of 1,4-naphthoquinone-2,3-bis-sulfides, synthesized with the aid of Novozym ® 51003 (M. thermophila laccase expressed in Aspergillus oryzae) catalysis, showed activity against melanoma (UACC62), prostate (PC3), breast (MCF7), and renal (TK10) cancer cell lines, with some compounds having IC 50 values under 10 µM [101].…”

Section: Pharma/cosmetics/agrochemicalsmentioning

confidence: 99%

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

et al. 2019

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There is a high number of well characterized, commercially available laccases with different redox potentials and low substrate specificity, which in turn makes them attractive for a vast array of biotechnological applications. Laccases operate as batteries, storing electrons from individual substrate oxidation reactions to reduce molecular oxygen, releasing water as the only by-product. Due to society’s increasing environmental awareness and the global intensification of bio-based economies, the biotechnological industry is also expanding. Enzymes such as laccases are seen as a better alternative for use in the wood, paper, textile, and food industries, and they are being applied as biocatalysts, biosensors, and biofuel cells. Almost 140 years from the first description of laccase, industrial implementations of these enzymes still remain scarce in comparison to their potential, which is mostly due to high production costs and the limited control of the enzymatic reaction side product(s). This review summarizes the laccase applications in the last decade, focusing on the published patents during this period.

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“…The use of synthetic fungicides is the main strategy to control this pathogen. The mechanisms of action of these fungicides are as diverse as their structures [4]. Succinate dehydrogenase inhibitors (SDHI), belonging to the carboxamide family, are the most used fungicides to control B. cinerea [5].…”

Section: Introductionmentioning

confidence: 99%

Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides

Melo

Armstrong

Navarro

et al. 2021

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A total of 12 compounds were synthesized from the natural sesquiterpene (-) drimenol (compounds 4 to 15). The synthesized compounds corresponded to N-phenyl-driman-9-carboxamide derivatives, similar to some fungicides that inhibit the electron-transport chain. Their structures were characterized and confirmed by 1H NMR, 13C NMR spectroscopy, and mass spectrometry. Compounds 5 to 15 corresponded to novel compounds. The effect of the compounds on the mycelial growth of Botrytis cinerea was evaluated. Methoxylated and chlorinated compounds in the aromatic ring (compounds 6, 7, 12, and 13) exhibited the highest antifungal activity with IC50 values between 0.20 and 0.26 mM. On the other hand, the effect on conidial germination of B. cinerea of one methoxylated compound (6) and one chlorinated compound (7) was analyzed, and no inhibition was observed. Additionally, compound 7 decreased 36% the rate of oxygen consumption by germinating conidia.

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Antifungal Activity against Botrytis cinerea of 2,6-Dimethoxy-4-(phenylimino)cyclohexa-2,5-dienone Derivatives

Cited by 10 publications

References 45 publications

Potential of the enzyme laccase for the synthesis and derivatization of antimicrobial compounds

Potential of the enzyme laccase for the synthesis and derivatization of antimicrobial compounds

Applications of Microbial Laccases: Patent Review of the Past Decade (2009–2019)

Characterization of the Fungitoxic Activity on Botrytis cinerea of N-phenyl-driman-9-carboxamides

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