Synthesis and Antioxidant Ability of Novel Derivatives Based on <i>para</i>‐Coumaric Acid Containing Isobornyl Groups

Буравлев, Е. В.; Dvornikova, I. A.; Schevchenko, Oksana G.; Kutchin, A. V.

doi:10.1002/cbdv.201900362

Cited by 17 publications

(8 citation statements)

References 58 publications

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“…Leaf extracts of Zanthoxylum bungeanum showed strong antioxidant effects in a previous study and were attributed to specific polyphenols such as trifolin (31.24 mg/g) [ 41 ]. In our study, p -coumaric acid showed noticeable antioxidant effects, which is in agreement with pervious investigations on other plants [ 42 , 43 ]. Rosmarinic acid antioxidant activities were comparable to antioxidant standards.…”

Section: Discussionsupporting

confidence: 93%

Polyphenols of Frangula alnus and Peganum harmala Leaves and Associated Biological Activities

Elansary

Szopa

Kubica

et al. 2020

Plants

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Frangula alnus and Peganum harmala populations growing in Saudi Arabia might be rich sources of natural compounds with important biological activities. A high performance liquid chromatography diode array revealed several polyphenols in the leaf extracts for the first time, including p-coumaric acid, rosmarinic acid, chlorogenic acid, ferulic acid, quercitrin, rutoside, quercetin and trifolin in F. alnus; and hydrocaffeic acid, protocatechuic acid, rosmarinic acid, caffeic acid and cynaroside in P. harmala. F. alnus and P. harmala showed strong antioxidant effects attributed to the polyphenolic composition of leaves and reduction of reactive oxygen species (ROS) accumulation. F. alnus and P. harmala leaf extracts showed cytotoxic effects against Jurkat, MCF-7, HeLa, and HT-29 cancer cells using MTT and flow cytometry assays. These activities were attributed to the polyphenolic composition of leaves including quercitrin, trifolin and cymaroside, as well as the activation of caspase family enzymes 2, 6, 8 and 9 in treated cancer cells compared to control. The current findings of this study include a novel comprehensive investigation on the polyphenol composition and anticancer effects of leaf extracts of F. alnus and P. harmala from natural populations in Saudi Arabia.

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Section: Discussionsupporting

confidence: 93%

Polyphenols of Frangula alnus and Peganum harmala Leaves and Associated Biological Activities

Elansary

Szopa

Kubica

et al. 2020

Plants

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“…Gallic acid (3,4,5-trihydroxybenzoic acid) is a known triphenolic compound that has strong antioxidant activities, as found in this study [ 50 ]. It was found that p -coumaric acid is a strong antioxidant, which is in agreement with previous investigations [ 51 , 52 ]. In L. inermis , moderate antioxidant activities were found, and these were attributed to the polyphenolic composition of leaf extracts including apigenin 5-glucoside.…”

Section: Discussionsupporting

confidence: 92%

Antioxidant and Biological Activities of Acacia saligna and Lawsonia inermis Natural Populations

Elansary

Szopa

Kubica

et al. 2020

Plants

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Acacia saligna and Lawsonia inermis natural populations growing in Northern Saudi Arabia might be a valuable source of polyphenols with potent biological activities. Using high-performance liquid chromatography–diode array detection (HPLC-DAD), several polyphenols were detected tentatively in considerable amounts in the methanolic leaf extracts of A. saligna and L. inermis. A. saligna mainly contained rutoside, hyperoside, quercetin 3-glucuronide, gallic acid and p-coumaric acid, whereas those of L. inermis contained apigenin 5-glucoside, apigetrin and gallic acid. Strong antioxidant activities were found in the leaf extracts of both species due to the presence of hyperoside, quercetin 3-glucuronide, gallic acid, isoquercetin, p-coumaric acid, quercitrin and rutoside. A. saligna and L. inermis leaf extracts as well as hyperoside, apigenin 5-glucoside, and quercetin 3-glucuronide significantly reduced reactive oxygen species accumulation in all investigated cancer cells compared to the control. Methanolic leaf extracts and identified polyphenols showed antiproliferative and cytotoxic activities against cancer cells, which may be attributed to necrotic cell accumulation during apoptotic periods. Antibacterial activities were also found in both species leaf extracts and were twice as high in A. saligna than L. inermis due to the high composition of rutoside and other polyphenols. Finally, strong antifungal activities were detected, which were associated with specific phenols such as rutoside, hyperoside, apigenin 5-glucoside and p-coumaric acid. This is the first study exploring the polyphenolic composition of A. saligna and L. inermis natural populations in northern Saudi Arabia and aiming at the detection of their biological activities.

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“…To assess the antioxidant potential of the synthesized compounds 2 – 5 , 7a – 12 , we used an already established set of methods [13,15–21,36,37] . Sesamol ( 1 ) and the standard antioxidant BHT (2,6‐di‐ tert ‐butyl‐4‐methylphenol) [38,39] were taken as the most suitable reference compounds.…”

Section: Resultsmentioning

confidence: 99%

“…It should be noted that often we were unable to identify significant relationships between RSA (DPPH‐test) and the parameters obtained using the above test systems. This fact indicates that the ability to interact with radicals is an important, but not the sole mechanism responsible for the AOA compounds in relation to biomolecules and living cells [18,21] . It is known that, in addition to the role of radical occludents and/or metal chelators, antioxidant molecules, including sesamol ( 1 ), can exhibit surface‐active properties, which allow them to reduce the interfacial tension and create more stable reverse micelles in emulsions [3,40] .…”

Section: Resultsmentioning

confidence: 99%

“…The aim of this work was to synthesize and evaluate the antioxidant potential ( in vitro ) of sesamol derivatives at the C‐6 position, as well as to identify the most promising products for further studies among them. The presented study is a continuation of our work searching for effective antioxidants among derivatives based on natural and synthetic phenolic compounds [13–21] . In our study, a comprehensive assessment of the AOA of the derivatives was carried out using both simple and widespread methods (e. g., radical scavenging activity (RSA) in the DPPH‐test) and more biologically relevant approaches (such as the ability of compounds to inhibit the oxidation of a model substrate containing animal lipids, as well as to protect mammalian RBCs from death under conditions of acute oxidative stress).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antioxidant Capacity of Some Derivatives of Sesamol at the C‐6 Position

Буравлев

Шевченко

Suponitsky

2021

Chemistry & Biodiversity

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Several synthetic approaches (aminomethylation, alkylation, condensation, etc.) have been used to synthesize derivatives based on the sesamol (1), natural phenol. The set of methods, including the study of antioxidant activity (AOA) by the ability to inhibit the initiated oxidation of animal lipids, radical scavenging activity, Fe2+‐chelation ability, as well as a comparative assessment of membrane‐protective activity under the conditions of H2O2‐induced hemolysis of mice red blood cells (RBCs), was used to analyze the antioxidant potential of the synthesized compounds. The synthesized derivatives have demonstrated different activity in the listed test systems, and we have identified compounds which appear to be most promising for a detailed study of their pharmacological properties.

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Synthesis and Antioxidant Ability of Novel Derivatives Based on para‐Coumaric Acid Containing Isobornyl Groups

Cited by 17 publications

References 58 publications

Polyphenols of Frangula alnus and Peganum harmala Leaves and Associated Biological Activities

Polyphenols of Frangula alnus and Peganum harmala Leaves and Associated Biological Activities

Antioxidant and Biological Activities of Acacia saligna and Lawsonia inermis Natural Populations

Synthesis and Antioxidant Capacity of Some Derivatives of Sesamol at the C‐6 Position

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