<i>In vitro</i> Evaluation of the Antileishmanial and Antischistosomal Activities of <i>p</i>‐Coumaric Acid Prenylated Derivatives

Vieira, Tatiana M.; Barco, Júlia G.; Paula, Lucas A. L.; Felix, Paulo C. A.; Bastos, Jairo K.; Magalhães, Lizandra G.; Crotti, Antônio E. M.

doi:10.1002/cbdv.202400491

Chemistry & Biodiversity

2024

DOI: 10.1002/cbdv.202400491

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In vitro Evaluation of the Antileishmanial and Antischistosomal Activities of p‐Coumaric Acid Prenylated Derivatives

Tatiana M. Vieira,

Júlia G. Barco,

Lucas A. L. Paula

et al.

Abstract: We have evaluated eight p‐coumaric acid prenylated derivatives in vitro for their antileishmanial activity against Leishmania amazonensis promastigotes and their antischistosomal activity against Schistosoma mansoni adult worms. Compound 7 ((E)‐3,4‐diprenyl‐4‐isoprenyloxycinnamic alcohol) was the most active against L. amazonensis (IC50 = 45.92 µM) and S. mansoni (IC50 = 64.25 µM). Data indicated that the number of prenyl groups, the presence of hydroxyl at C9, and a single bond between C7 and C8 are important… Show more

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Cited by 4 publications

References 34 publications

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Antibacterial and Antileishmanial Activity of 1,4‐Dihydropyridine Derivatives

Oliveira,

Silva,

Silva

et al. 2024

Chemistry & Biodiversity

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: We have synthesized twenty‐three 1,4‐dihydropyridine derivatives (1,4‐DHPs) by using a microwave‐assisted one‐pot multicomponent Hantzsch reaction and evaluated their antibacterial activity against a representative panel of cariogenic bacteria and their in vitro antileishmanial activity against Leishmania (L.) amazonensis promastigotes and amastigotes. Thirteen compounds were moderately active against Streptococcus sanguinis, Streptococcus mitis, and Lactobacillus paracasei. Compound 22 (diethyl 4‐(3‐methoxy‐4‐hydroxyphenyl)‐2,6‐dimethyl‐1,4‐dihydropyridine‐3,5‐dicarboxylate) displayed moderate antibacterial activity against S. mitis and S. sanguinis, with a Minimum Inhibitory Concentration (MIC) of 500 µg/mL); compounds 8 (ethyl 2,7,7‐trimethyl‐4‐(3‐chlorophenyl)‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate) and 10 (ethyl 2,7,7‐trimethyl‐4‐(3‐nitrophenyl)‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate) were moderately active against S. sanguinis (MIC = 500 µg/mL) and very active against L. amazonensis promastigotes (IC50 = 43.08 and 34.28 µM, respectively). Among the eight 1,4‐DHPs that were active (IC50 < 50 µM) against L. amazonensis promastigotes, compound 13 (ethyl 2,7,7‐trimethyl‐4‐(3,4,5‐trimethoxyphenyl)‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate) was the most active (IC50 = 24.62 µM) and had a Selectivity Index (SI) higher than 4 compared to GM07492A cells. On the other hand, compound 9 (ethyl 2,7,7‐trimethyl‐4‐(2‐nitrophenyl)‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline‐3‐carboxylate) was the most active against L. amazonensis amastigotes (IC50 = 16.27 µM and SI = 6.1) after 24 h of treatment. Based on our results, asymmetric 1,4‐DHPs derived from dimedone exhibit antileishmanial potential.

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Antibacterial and Antileishmanial Activity of 1,4‐Dihydropyridine Derivatives

Oliveira,

Silva,

Silva

et al. 2024

Chemistry & Biodiversity

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Cupressus sempervirens recovers disturbance of normal male fertilization in Schistosoma mansoni-infected mice

Koriem,

El-Gohary

2024

J Parasit Dis

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Chemical Synthesis of Monolignols: Traditional Methods, Recent Advances, and Future Challenges in Sustainable Processes

Tiz,

Tofani,

Vicente

et al. 2024

Antioxidants

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Monolignols represent pivotal alcohol-based constituents in lignin synthesis, playing indispensable roles in plant growth and development with profound implications for industries reliant on wood and paper. Monolignols and their derivates have multiple applications in several industries. Monolignols exhibit antioxidant activity due to their ability to donate hydrogen atoms or electrons to neutralize free radicals, thus preventing oxidative stress and damage to cells. Characterized by their alcohol functionalities, monolignols present three main forms: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol. In nature, particularly in plants, monolignols with geometry (E) predominate over their Z counterparts. The methods for obtaining the three canonical monolignols, two less-common monolignols, and a monolignol analogue are addressed to present an overview of these phenol-based compounds, particularly from a synthetic standpoint. A SWOT (Strengths, Weaknesses, Opportunities, and Threats) analysis is used to explain the advantages and disadvantages of synthesizing monolignols, key alcohol-containing raw materials with enormous significance in both plant biology and industrial applications, using bench chemical methods. The uniqueness of this work is that it provides an overview of the synthetic pathways of monolignols to assist researchers in pharmaceutical and biological fields in selecting an appropriate procedure for the preparation of their lignin models. Moreover, we aim to inspire scientists, particularly chemists, to develop more sustainable synthetic protocols for monolignols.

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In vitro Evaluation of the Antileishmanial and Antischistosomal Activities of p‐Coumaric Acid Prenylated Derivatives

Cited by 4 publications

References 34 publications

Antibacterial and Antileishmanial Activity of 1,4‐Dihydropyridine Derivatives

Antibacterial and Antileishmanial Activity of 1,4‐Dihydropyridine Derivatives

Cupressus sempervirens recovers disturbance of normal male fertilization in Schistosoma mansoni-infected mice

Chemical Synthesis of Monolignols: Traditional Methods, Recent Advances, and Future Challenges in Sustainable Processes

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