Antioxidant properties of terpene-substituted phenols

Chukicheva, I. Yu.; Буравлев, Е. В.; Федорова, И. В.; Borisenkov, Mikhail F.; Kutchin, A. V.

doi:10.1007/s11172-010-0388-5

Cited by 25 publications

(6 citation statements)

References 9 publications

(5 reference statements)

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“…Novel para-coumaric acid derivatives were synthesized from 2,6-diisobornyl-4-methylphenol (1) 2 , which is a close analog of the known antioxidant 2,6-di-tertbutyl-4-methylphenol (BHT) and has terpene fragments with isobornyl (bicyclo[2.2.1]heptane) [17] structure instead of tert-butyl groups. As shown previously, compound 1 exhibits AO properties in vitro, [18,19] surpassing the activity of BHT by a number of parameters, and is characterized by low hemolytic efficiency. [20] During the experiments on laboratory animals, compound 1 showed rheologic activity in ischemia/reperfusion [21] conditions and cardioprotective properties.…”

Section: Resultssupporting

confidence: 64%

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

Буравлев

Dvornikova

Schevchenko

et al. 2019

Chemistry & Biodiversity

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A series of novel esters and amides was synthesized on the basis of para‐coumaric acid containing isobornyl groups in ortho‐positions relative to the phenolic hydroxy group. Antioxidant properties of the obtained compounds were evaluated and compared on in vitro models: radical‐scavenging ability, antioxidant activity on a substrate containing the lipids of animal brain, cytotoxicity of red blood cells, antioxidant and membrane‐protective properties on the model of oxidative red blood cells hemolysis. Statistically significant relationship was established between the antioxidant activity of the studied compounds in model system containing animal lipids and the parameters reflecting their antioxidant properties on the model of H2O2‐induced hemolysis of red blood cells. It was determined that an amide with a morpholine fragment has the highest antioxidant activity. The specified derivative significantly surpassed the reference substances (parent acid, BHT) and was not inferior to the effective antioxidant 2,6‐diisobornyl‐4‐methylphenol in terms of its properties.

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Section: Resultssupporting

confidence: 64%

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

Буравлев

Dvornikova

Schevchenko

et al. 2019

Chemistry & Biodiversity

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“…Evaluation of the antioxidant activity was performed by coulometric titration with electrogenerated bromine using an EKSPERT 006 coulometric analyzer (EkoniksEkspert, Moscow) with glassy carbon electrodes (Chukicheva et al, 2010). The reference (anode of was 2.3 cm2 in area) and the auxiliary (cathode) electrodes were glassy carbon rods of 3mm in diameter; needlelike platinum electrodes were the indicators; 0.2M potassium bromide in 0.1M sulphuric acid was the supporting electrolyte; the operating current was 5.27mA, the auxiliary current was 0.79mA; the level of measurement was 300mV, the level of reduction was 500mV.…”

Section: Measurement Of Antioxidant Activitymentioning

confidence: 99%

Influence of Freezing and Drying on Phytochemical Properties of Various Fruit

Семенов¹,

Krasnova²,

Suvorov³

et al. 2015

Biosci., Biotechnol. Res. Asia

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Initially the total antioxidant activity, the total flavonoid contents, the total phenolic contents and the ascorbic acid were measured in fresh fruits. Then samples for freezing and vacuum freeze-drying were frozen what led to a decrease in total antioxidant activity by 11% (persimmon)-28% (kiwi fruit), a reduction of total phenolic and total flavonoid contents for about 10% and the content of ascorbic acid decreases by 8% (kiwi fruit)-30% (apple). The remaining frozen purees were subjected to vacuum freeze-drying at the temperature plus 25-27 ºC and a chamber pressure of 80 Pa in the primary drying and the temperature plus 38-40 ºC and a chamber pressure of 80 Pa at the secondary drying. The total antioxidant activity of freeze dried samples in comparison with fresh fruit decreased by 20% (persimmon)-50-55% (apple), the total content of flavonoids and phenolic compounds decreased by 20-30%, reduction of the ascorbic acid ranged from 23-29% (apple and persimmon) to 55% (pear). The other part was subjected to convective drying and as a result the total antioxidant activity decreased by 46% (persimmon) to 68% (pear and apple), the total content of flavonoid contents compounds decreased by 42% (apple, kiwi, persimmon)-56% (pear). The total content of phenolic compounds in all samples decreased by 40-45% and the content of ascorbic acid reduced by 45-55%. The study results demonstrated that the antioxidant properties of the fruits studied in the following order: fresh fruit> frozen fruit> freeze-dried fruit> convective dried fruit.

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“…[6][7] It is known that isobornylphenols possess membrane-protecting properties [8] and can be used as bio-and technical antioxidants. [9] Therefore, the synthesis of porphyrin macrocycles with such substituents is of interest for the synthesis of hybrid antioxidants. In addition, isobornylphenols exhibit anti-inflammatory and hemorheological activity, [10][11][12][13] what allows to consider isobornylphenolic fragment as a potential pharmacophore group.…”

Section: Introductionmentioning

confidence: 99%