Synthesis and Anti-Saprolegnia Activity of New 2’,4’-Dihydroxydihydrochalcone Derivatives

Werner, Enrique; Montenegro, Iván; Said, Bastián; Godoy, Patrício; Besoaín, Ximena; Caro, Nelson; Madrid, Alejandro

doi:10.3390/antibiotics9060317

Cited by 4 publications

(4 citation statements)

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“…However, the MIC values of compound 8 for growth inhibition of S. parasitica and P. cinnamomi were 50 and 75 µg/mL, respectively, while for compound 9, which differs by hydroxyl group with 1 , these values decreased to 75 µg/mL for the two strains, respectively. These data confirm what has been suggested in previous studies about the importance of the relationship between aldehydic and alcohol compounds and anti-oomycete activity [ 37 , 38 ]. It also confirms that aldehydic compounds ( 1 – 2 ) and compound 4 have a similar structure, where the anti-oomycete activity decreases in the tested microorganisms due to the absence of an α,β-unsaturated carbonyl system [ 38 ].…”

Section: Discussionsupporting

confidence: 92%

“…These data confirm what has been suggested in previous studies about the importance of the relationship between aldehydic and alcohol compounds and anti-oomycete activity [ 37 , 38 ]. It also confirms that aldehydic compounds ( 1 – 2 ) and compound 4 have a similar structure, where the anti-oomycete activity decreases in the tested microorganisms due to the absence of an α,β-unsaturated carbonyl system [ 38 ].…”

Section: Discussionsupporting

confidence: 92%

“…The nordrimanic compounds 5 and 7 with ketone group α,β-unsaturated carbonyl system exhibited moderate anti-Saprolegnia activity at concentrations (125–150 µg/mL), and only compound 6 showed low activity with similar effect to positive control fluconazole and bronopol against the two oomycetes tested. This decrease in the anti-oomycete activity of the drimane compounds could be related to the higher reactivity of the aldehyde groups over the keton groups and over the lactone compound 6, leading to a decrease in the anti-Saprolegnia activity of 6 as occurs with other fungal microorganisms in this same assay [ 27 , 38 ]. In order to establish the possible route of death of the anti-oomycete strains, the membrane damage experiment was therefore carried out.…”

Section: Discussionmentioning

confidence: 99%

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Antimicrobial Activity of Drimanic Sesquiterpene Compounds from Drimys winteri against Multiresistant Microorganisms

Montenegro,

Pazmiño,

Araque

et al. 2024

Molecules

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In this work, a group of ten sesquiterpene drimanes, including polygodial (1), isopolygodial (2), and drimenol (3) obtained from the bark of Drimys winteri F. and seven synthetic derivatives, were tested in vitro against a unique panel of bacteria, fungi, and oomycetes with standardized procedures against bacterial strains K. pneumoniae, S. tiphy, E. avium, and E. coli. The minimum inhibitory concentrations and bactericidal activities were evaluated using standardized protocols. Polygodial (1) was the most active compound, with MBC 8 μg/mL and MIC 16 μg/mL in E. avium; MBC 16 μg/mL and MIC 32 μg/mL in K. pneumoniae; MBC 64 μg/mL and MIC 64 μg/mL in S. typhi; and MBC 8 μg/mL and MIC 16 μg/mL and MBC 32 μg/mL and MIC 64 μg/mL in E. coli, respectively. The observed high potency could be attributed to the presence of an aldehyde group at the C8–C9 position. The antifungal activity of 1 from different microbial isolates has been evaluated. The results show that polygodial affects the growth of normal isolates and against filamentous fungi and oomycetes with MFC values ranging from 8 to 64 μg/mL. Sesquiterpene drimanes isolated from this plant have shown interesting antimicrobial properties.

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Section: Discussionsupporting

confidence: 92%

Section: Discussionsupporting

confidence: 92%

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Antimicrobial Activity of Drimanic Sesquiterpene Compounds from Drimys winteri against Multiresistant Microorganisms

Montenegro,

Pazmiño,

Araque

et al. 2024

Molecules

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“…Research efforts have continued till date to seek alternatives and develop new strategies for the control of Saprolegniasis in aquaculture, with special attention on toxicity and safety (Ali et al, 2019; Meneses et al, 2022; Werner et al, 2020; Zhang et al, 2019). Based on the known antimicrobial activity of copper, we evaluated a new strategy that can increase the antimicrobial efficiency of copper against S. parasitica by combining low doses of ionophores and copper sulfate (Straus et al, 2020).…”

Section: Discussionmentioning

confidence: 99%

Modulation ofSaprolegnia parasiticagrowth with copper and ionophores

Ogunwa,

Thornhill,

Ledezma

et al. 2024

Preprint

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Saprolegnia parasiticais an oomycete pathogen responsible for saprolegniasis diseases that result in large production losses in the catfish and salmon aquaculture industry. The use of copper sulfate as an anti-Saprolegnia treatment has been reported as an alternative to malachite green, formaldehyde and hydrogen peroxide treatment methods. The current study investigates a new strategy to inhibitSaprolegnia parasiticagrowth by combining copper and ionophores at low levels. The chemical agents tetraethylthiuram disulfide (TDD), ciclopirox olamine (CLP), 2-mercaptopyridine N-oxide (MPO), 5-chloro-8-hydroxy-7-iodoquinoline (CHI), 5,7-dichloro-8-hydroxyquinoline (DHQ) and 8-Quinolinol (8QN) were identified to inhibitS. parasiticagrowth in a copper-dependent manner. At concentrations below the lethal dose of individual ionophore, increasing copper concentrations resulted in synergeticS. parasiticagrowth inhibition. The addition of the exogenous copper chelator bathocuproine sulfate (BCS), reversed the inhibition ofS. parasiticagrowth by TDD, CLP, MPO, and 8QN but not CHI and DHQ. Our data demonstrates that ionophores, in combination with low levels of copper, can effectively limitS. parasiticagrowth both in a liquid and solid support growth environment. Investigations into the underlying mechanism of Cu-ionophore toxicity are discussed.

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Anti‐saprolegnia Effect of Oxyprenylated Derivatives of Naturally Occurring Prenylated Dihydrochalcone

Madrid,

Silva,

Muñoz

et al. 2024

ChemistrySelect

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Oomycetes such as Saprolegnia sp. are responsible for serious economic losses in aquaculture, the strategies for their control lead to concerns about their efficacy and environmental repercussions, so alternatives for their regulation are being sought. The aim of this study was to evaluate the in vitro susceptibility of 2 representative strains of Saprolegnia sp. toward 2,4‐dihydroxy‐5′‐prenyl‐dihydrochalcone (A); dihydrochalcone isolated from the Chilean shrub Adesmia balsamica; and their derivatives oxyprenylated (B‐‐G) with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. The minimum inhibitory concentration (MIC) and minimum oomycetocidal concentration (MOC) values were then determined for the series of compounds tested, in comparison with the conventional fungicides bronopol® and fluconazole plus the natural compound safrole, by quantifying fungal growth. Significant growth inhibition was observed for prenylated derivatives B–G, evidencing dihydrochalcone E as the most active. This compound presented MIC and MOC values (0.24–0.26 μM and 0.30–0.33 μM, respectively) superior to those determined for commercial antifungal in both of the tested pathogenic strains.

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Synthesis and Anti-Saprolegnia Activity of New 2’,4’-Dihydroxydihydrochalcone Derivatives

Cited by 4 publications

References 28 publications

Antimicrobial Activity of Drimanic Sesquiterpene Compounds from Drimys winteri against Multiresistant Microorganisms

Antimicrobial Activity of Drimanic Sesquiterpene Compounds from Drimys winteri against Multiresistant Microorganisms

Modulation ofSaprolegnia parasiticagrowth with copper and ionophores

Anti‐saprolegnia Effect of Oxyprenylated Derivatives of Naturally Occurring Prenylated Dihydrochalcone

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