Natural Cinnamic Acid Derivatives: A Comprehensive Study on Structural, Anti/Pro-Oxidant, and Environmental Impacts

Gryko, Kamila; Kalinowska, Monika; Ofman, Piotr; Choińska, Renata; Świderski, Grzegorz; Świsłocka, Renata; Lewandowski, W.

doi:10.3390/ma14206098

Cited by 7 publications

(3 citation statements)

References 53 publications

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“…Its derivatives are important promising substances with great potential in the search for new pharmacologically active substances [ 5 , 6 ]. Cinnamic acid and its derivatives have attracted the attention of scientists in recent decades due to low toxicity and a wide range of biological activities such as antibacterial, antiviral, anti-inflammatory, cytotoxic, antidiabetic, hepatoprotective, antioxidant, neuroprotective, anxiolytic, and antituberculotic [ 7 , 8 , 9 , 10 , 11 , 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides

Strhársky

Pindjakova

Kos

et al. 2022

IJMS

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A series of eighteen 4-chlorocinnamanilides and eighteen 3,4-dichlorocinnamanilides were designed, prepared and characterized. All compounds were evaluated for their activity against gram-positive bacteria and against two mycobacterial strains. Viability on both cancer and primary mammalian cell lines was also assessed. The lipophilicity of the compounds was experimentally determined and correlated together with other physicochemical properties of the prepared derivatives with biological activity. 3,4-Dichlorocinnamanilides showed a broader spectrum of action and higher antibacterial efficacy than 4-chlorocinnamanilides; however, all compounds were more effective or comparable to clinically used drugs (ampicillin, isoniazid, rifampicin). Of the thirty-six compounds, six derivatives showed submicromolar activity against Staphylococcus aureus and clinical isolates of methicillin-resistant S. aureus (MRSA). (2E)-N-[3,5-bis(trifluoromethyl)phenyl]- 3-(4-chlorophenyl)prop-2-enamide was the most potent in series 1. (2E)-N-[3,5-bis(Trifluoromethyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide, (2E)-3-(3,4-dichlorophenyl)-N-[3-(trifluoromethyl)phenyl]prop-2-enamide, (2E)-3-(3,4-dichloro- phenyl)-N-[4-(trifluoromethyl)phenyl]prop-2-enamide and (2E)-3-(3,4-dichlorophenyl)- N-[4-(trifluoromethoxy)phenyl]prop-2-enamide were the most active in series 2 and in addition to activity against S. aureus and MRSA were highly active against Enterococcus faecalis and vancomycin-resistant E. faecalis isolates and against fast-growing Mycobacterium smegmatis and against slow-growing M. marinum, M. tuberculosis non-hazardous test models. In addition, the last three compounds of the above-mentioned showed insignificant cytotoxicity to primary porcine monocyte-derived macrophages.

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Section: Introductionmentioning

confidence: 99%

Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides

Strhársky

Pindjakova

Kos

et al. 2022

IJMS

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“…In the present study, maximum inhibition of 95.7% occurred at 200 μg/mL concentration using standard gallic acid whereas the IC50 values of cinnamic derivative compounds 3a (OH derivatives) and 3b (-OH-OH derivatives) were found to be 81.27μg/mL and 129.27μg/mL respectively. Thus signifying derivatives of cinnamic acid as a potential scavenger with antiradical activity enhanced by an increased number of hydroxyl derivative groups (-OH p-hydroxy < dihydroxy < hydroxydimethyl) caused by a decrease in the kinetic stability, and influence of aromatic substitution as a result of symmetrization of the electronic charge dissemination of these 3a and 3b compound molecules [9].…”

Section: Discussionmentioning

confidence: 99%

Assessment of Therapeutic Bio-Activity of Cinnamoyl Sulfonamide Hydroxamate in Squamous Cell Carcinoma

Cherian,

Goyal,

Mittal

et al. 2023

Cureus

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BackgroundCancer is the second most common cause of death. Oral squamous cell carcinoma (OSCC) represents the most frequent of all oral neoplasms. Many treatment modalities such as chemotherapy, radiotherapy, surgery, and immunotherapy are emerging but still, the patients' quality of life is questionable. Despite the advances in therapeutic approaches, the percentages of morbidity and mortality of OSCC have not improved significantly during the last 30 years. Treatment using natural products can act as a potent anti-cancer agent with reduced adverse effects. Cinnamic acid derivatives exhibit anti-cancer potential through histone deacetylase inhibitor (HDAC) enzyme inhibition. MethodologyIn an experimental study design, cinnamoyl hydroxamate derivatives were prepared. The structure was confirmed using ultraviolet-visible spectroscopy (UV-Vis), nuclear magnetic resonance (NMR), infrared spectroscopy, and mass spectrophotometry. An in-vitro antioxidant assay using nitric oxide scavenging and reducing power assay was done and an in-vitro cytotoxic (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide) (MTT) assay and viability assay were carried out using tryphan blue dye. ResultsStatistical analysis was performed using SPSS (IBM Corp. Released 2013. IBM SPSS Statistics for Windows, Version 22.0. Armonk, NY: IBM Corp). Cinnamoyl hydroxamate derivatives were obtained and named as compounds 3a (E)-N-Hydroxy-3-(4-(N-(phenyl bromo) sulfamoyl) phenyl) acrylamide-) and 3b ((E)-N-Hydroxy-3-(4-(N-(phenyl nitro) sulfamoyl) phenyl) acrylamide). In the nitric oxide scavenging assay, compound 3a showed good antioxidant activity than 3b. Reducing power assay was higher in 3a compared to 3b. Cell viability using tryphan blue exhibited a concentration decrease in % cell viability with an increase in the concentration of human oral cavity squamous cell carcinoma cell line (OECM 1), a unique head and neck squamous carcinoma cell line (UM SCC 6) & human oral squamous cell carcinoma forming metastatic foci (HSC 3) cell lines. ConclusionThe results of the present study revealed that the study compounds play a vital role in the up-regulation of apoptotic pathways and regulation of terminal differentiation pathways. The compounds showed good antioxidant and anti-cancer activities in lesser concentrations, hence they can be used as a therapeutic agent for oral squamous cell carcinoma.

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“…Phenolic acids constitute a subclass of polyphenols characterized by the presence of at least one hydroxyl-substituted phenolic group and a carboxylic group. They can be commonly found in plant matrices bound to small organic acids (quinic, maleic, or tartaric) or linked to structural components of plant cells (cellulose, proteins, or lignin) and are rarely found in their free form [50,51]. The results of the Arnov assay demonstrate that the content of phenolic acids in BOE and LE is very similar and corresponds to approximately 40% of the total phenols.…”

Section: Antioxidant Performances Of the Extractsmentioning

confidence: 99%

Formulation of Antioxidant Gummies Based on Gelatin Enriched with Citrus Fruit Peels Extract

Aiello,

Caputo,

Oliviero Rossi

et al. 2024

Foods

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In this work, the peels of red and blonde oranges as well as lemons were efficiently (5.75–9.65% yield) extracted by hydroalcoholic solution with ultrasound assistance and employed as active molecule sources in the preparation of functional gummies. Antioxidant performances of the hydroalcoholic extracts were characterized by colorimetric assays, whereas LC–HRMS analyses identified the main bioactive compounds (phenolic acids and flavonoids). The highest scavenging activity was recorded for lemon extract in an aqueous environment (IC50 = 0.081 mg mL−1). An ecofriendly grafting procedure was performed to anchor polyphenols to gelatin chains, providing macromolecular systems characterized by thermal analysis and antioxidant properties. Scavenger abilities (IC50 = 0.201–0.454 mg mL−1) allowed the employment of the conjugates as functional ingredients in the preparation of gummies with remarkable antioxidant and rheological properties over time (14 days). These findings confirmed the possible employment of highly polluting wastes as valuable sources of bioactive compounds for functional gummies preparation.

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Natural Cinnamic Acid Derivatives: A Comprehensive Study on Structural, Anti/Pro-Oxidant, and Environmental Impacts

Cited by 7 publications

References 53 publications

Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides

Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides

Assessment of Therapeutic Bio-Activity of Cinnamoyl Sulfonamide Hydroxamate in Squamous Cell Carcinoma

Formulation of Antioxidant Gummies Based on Gelatin Enriched with Citrus Fruit Peels Extract

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