Antioxidant capacity of eugenol derivatives

Hidalgo, Mayra; Rosa, Carlos de; Carrasco, Héctor; Cardona, Wilson; Gallardo, C.; Espinoza, Luis

doi:10.1590/s0100-40422009000600020

Cited by 57 publications

(42 citation statements)

References 13 publications

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“…Structural differences or the ratio of the compounds to each other may account for the differences. Hidalgo et al (2009) studied the effect of donating electrons from eugenol derivatives; their results support our findings. They found that two eugenol derivatives displayed higher ORAC values due to their ability to stabilize the radical in the ortho (o) and para (p) positions of an aromatic ring.…”

Section: Oracsupporting

confidence: 79%

Synergistic Endo- and Exo-Interactions Between Blueberry Phenolic Compounds, Grape Variety Fractions, Chocolate Covered Strawberries, and Fruit Smoothies

Epps¹,

Stenquist²,

Lowder³

et al. 2013

JFR

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The presence of phytochemicals in fruits and vegetables is considered to be of nutritional importance in the prevention of chronic diseases, such as cancer and cardiovascular disease. Through overlapping or complementary effects, the complex mixture of phytochemicals in fruits and vegetables provides a better protective effect on health than single phytochemicals. Previous studies have shown that synergistic interactions between antioxidants in food result in a higher antioxidant capacity than individually isolated antioxidants. Further work is needed to explore other potential synergistic interactions between antioxidant mixtures within foods (endo-interactions) and between foods (exo-interactions) commonly eaten together. A series of studies examined potential synergy between various components of blueberries, grapes, chocolate covered strawberries, and fruit smoothies using multiple antioxidant assays (ORAC, TEAC and DPPH). At the ratio found in blueberries, significant synergy, antagonism, and patterns were found for many phenolic compound combinations, though they were dependent on the assay. Significant synergy was found in the combinations of skin and juice as well as skin, juice, and seed across three grape varieties. Significant synergy was found in the combination of strawberry and 88% cocoa chocolate in fully dipped strawberries. Fruit smoothies made with blueberries (as opposed to strawberries and raspberries) and soymilk (as opposed to water) exhibited significantly higher antioxidant capacity. The 3 assays measured correlated weakly with each other. This work furthers our understanding of the potential value of complex mixtures and foods in the human diet and is the first to report on the combinations and fractions described.

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Section: Oracsupporting

confidence: 79%

Synergistic Endo- and Exo-Interactions Between Blueberry Phenolic Compounds, Grape Variety Fractions, Chocolate Covered Strawberries, and Fruit Smoothies

Epps¹,

Stenquist²,

Lowder³

et al. 2013

JFR

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“…Miranda, Cardoso, Batista, Rodrigues, & Figueiredo (2016) The high values for the antioxidant activities presented by BHT and the low values presented by the essential oil can be explained by the fact that the reduction of DPPH occurs via transfer of a hydrogen atom or a mechanism of electron transfer from the antioxidant compound. In general, the constituents of the essential oil did not resemble the phenolic structure of BHT, which can donate the hydrogen atom of the hydroxyl group to form a phenol radical that can be stabilized by resonance with the double bonds of the aromatic ring (Hidalgo et al, 2009). Besides, terpenes show low solubility in the reaction medium of the assay, because this test utilizes methanol or ethanol as solvent.…”

Section: Antioxidant Activitymentioning

confidence: 97%

<b>Essential oil from <i>Chenopodium ambrosioides</i> L.: secretory structures, antibacterial and antioxidant activities

Santiago

Cardoso

Batista

et al. 2016

Acta Sci. Biol. Sci.

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ABSTRACT. The aim of this study was to evaluate the antibacterial and antioxidant activities of essential oil from Chenopodium ambrosioides L. and to determine its secretory structures. The essential oil was extracted through the hydrodistillation technique using a modified Clevenger apparatus (2 hours) and chemically characterized by GC/MS and GC-FID. The antioxidant activity was determined by monitoring the reduction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and by the oxidation of the β-carotene/linoleic acid system. The evaluation of antibacterial activity was performed by the agar cavity diffusion technique using the microorganisms Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella Cholerasuis. The characterization of trichomes was accomplished by Scanning Electron Microscopy (SEM) and histochemical tests with Nadi and Sudan IV reagents. The antioxidant activity demonstrated by the β-carotene/acid linoleic test, with IC 50 = 455.7 μg mL -1 . This oil also presented antibacterial activity for both Gram-negative and Gram-positive bacteria. The minimal inhibitory concentration ranged 62.5 to 250 μL mL -1. The presence of terpenes in the glandular trichomes was observed, suggesting that the essential oil is secreted by these structures.Keywords: natural products, antioxidant assays, antimicrobial, trichomes.Óleo essencial de Chenopodium ambrosioides L.: estruturas secretoras, atividade antibacteriana e antioxidante RESUMO. Objetivou-se neste trabalho avaliar as atividades antibacteriana e antioxidante do óleo essencial de Chenopodium ambrosioides L. e determinar as suas estruturas secretoras. A extração do óleo essencial foi realizada pelo método de hidrodestilação, utilizando o aparelho de Clevenger modificado com duração de 2 horas, sendo, posteriormente, analisado por CG/EM e CG-DIC. A atividade antioxidante foi determinada monitorando-se a redução do radical livre DPPH (2,2-difenil-1-picril-hidrazila) e utilizando o ensaio de oxidação do sistema β-caroteno/ácido linoleico. A avaliação da atividade antibacteriana foi realizada por meio da técnica difusão cavidade em ágar, utilizando os micro-organismos Staphylococcus aureus, Listeria monocytogenes, Escherichia coli e Salmonella Cholerasuis. A caracterização dos tricomas foi realizada por Microscopia Eletrônica de Varredura (MEV) e pelos testes histoquímicos com os reagentes de Nadi e Sudan IV. A atividade antioxidante foi evidenciada pelo teste β-caroteno/ácido linoleico, com CI 50 455,7 μg mL -1. O óleo também apresentou atividade antibacteriana tanto para bactérias Gram-negativas como para Gram-positivas. A concentração mínima inibitória do mesmo variou entre 62,5 e 250 μL mL -1. Constatouse a presença de compostos terpênicos nos tricomas glandulares, inferindo-se que o óleo essencial seja secretado nessas estruturas.Palavras-chave: produtos naturais, ensaios antioxidantes, antimicrobiano, tricomas.

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“…Eugenol derivatives exhibited a haemolysis percentage lower than 1%, which indicate very low toxicity for red blood cell membranes. 3 In vitro studies carried out on two human cancer cell lines: DU-145 (androgen-insensitive prostate cancer cells) and KB (oral squamous carcinoma cells) measuring cell viability by the tetrazolium salt assay. Lactic dehydrogenase (LDH) release was also measured to evaluate cell toxicity as a result of cell disruption, subsequent to membrane rupture.…”

Section: Introductionmentioning

confidence: 99%

“…Safrole (1) and its synthetic derivatives (2)(3)(4)(5)(6)(7)(8) were tested in vitro for antiproliferative effect on two human tumor breast cancer cell lines (MDA-MB-231, MCF-7), one human colorectal cancer cell line (DLD-1) and one dermal human fibroblast cell line (DHF). The in vitro growth inhibition assay used was based on sulphorhodamine dye, widely used to quantify cell viability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Espinoza

Madrid

Liber

et al. 2010

J. Chil. Chem. Soc.

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Safrole from sassafras oil (Ocotea pretiosa Mez., Lauraceae), is an abundant natural product showing interesting functionality and chemical structure. Starting from safrole, nine derivatives were prepared and assessed for antiproliferative effect using different human cell lines. The in vitro growth inhibition assay was based on the sulphorhodamine dye to quantify cell viability. Some safrole derivatives, (2E)-3-(3',4'-methylenedioxi)phenyl acrylaldehyde (3) and 4-allyl-5-nitrobenzene-1,2-diol (4) presented better antiproliferative effect than the parent compound on two breast cancer cell lines (MCF-7 and MDA-MB-231) and one human colorectal cancer cell line (DLD-1) with IC 50 values of 55.0 + 7.11 µM, 37.5 + 2.65 µM and 44.0 + 6.92 µM, respectively, without toxicity towards dermal human fibroblast (DHF cells).

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Antioxidant capacity of eugenol derivatives

Cited by 57 publications

References 13 publications

Synergistic Endo- and Exo-Interactions Between Blueberry Phenolic Compounds, Grape Variety Fractions, Chocolate Covered Strawberries, and Fruit Smoothies

Synergistic Endo- and Exo-Interactions Between Blueberry Phenolic Compounds, Grape Variety Fractions, Chocolate Covered Strawberries, and Fruit Smoothies

<b>Essential oil from <i>Chenopodium ambrosioides</i> L.: secretory structures, antibacterial and antioxidant activities

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

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