scholarly journals Enhancement of the Antioxidant and Skin Permeation Properties of Eugenol by the Esterification of Eugenol to New Derivatives

2020 ◽  
Author(s):  
EDYTA MAKUCH ◽  
Anna Nowak ◽  
Andrzej Günther ◽  
Robert Pełech ◽  
Łukasz Kucharski ◽  
...  

Abstract The aim of the study was to determine the antioxidant activity and assess the lipophilicity and skin penetration of eugenyl chloroacetate (EChA), eugenyl dichloroacetate (EDChA), and eugenyl trichloroacetate (ETChA). Identification of the obtained products was based on gas chromatography (GC), infrared spectroscopy (FTIR/ATR), gas chromatography coupled with mass spectrometry (GC-MS), and the analysis of 13C-NMR and 1H-NMR spectra. The antioxidative capacity of the derivatives obtained was determined by the DPPH free radical reduction method, while the octanol/water partition coefficient (shake-flask method) was tested to determine the lipophilicity of these compounds. In the next stage of testing EDChA and ETChA–(compounds characterized by the highest degree of free radical scavenging), the penetration of DPPH through pig skin and its accumulation in the skin were evaluated. For comparison, penetration studies of eugenol alone as well as dichloroacetic acid (DChAA) and trichloroacetic acid (TChAA) were also carried out. The antioxidant activity (DPPH, ABTS, and Folin–Ciocalteu methods) of the fluid that penetrated through pig skin was also evaluated. The in vitro pig skin penetration study showed that eugenol derivatives are particularly relevant for topical application. The obtained derivatives were characterized by a high level of antioxidant activity estimated after 24 hours of conducting the experiment, which indicates long-term protection against reactive oxygen species (ROS) in the deeper layers of the skin.


AMB Express ◽  
2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Edyta Makuch ◽  
Anna Nowak ◽  
Andrzej Günther ◽  
Robert Pełech ◽  
Łukasz Kucharski ◽  
...  

Abstract The aim of the study was to determine the antioxidant activity and assess the lipophilicity and skin penetration of eugenyl chloroacetate (EChA), eugenyl dichloroacetate (EDChA), and eugenyl trichloroacetate (ETChA). Identification of the obtained products was based on gas chromatography (GC), infrared spectroscopy (FTIR/ATR), gas chromatography coupled with mass spectrometry (GC-MS), and the analysis of 13C-NMR and 1H-NMR spectra. The antioxidative capacity of the derivatives obtained was determined by the DPPH free radical reduction method, while the octanol/water partition coefficient (shake-flask method) was tested to determine the lipophilicity of these compounds. In the next stage of testing EDChA and ETChA–(compounds characterized by the highest degree of free radical scavenging), the penetration of DPPH through pig skin and its accumulation in the skin were evaluated. For comparison, penetration studies of eugenol alone as well as dichloroacetic acid (DChAA) and trichloroacetic acid (TChAA) were also carried out. The antioxidant activity (DPPH, ABTS, and Folin–Ciocalteu methods) of the fluid that penetrated through pig skin was also evaluated. The in vitro pig skin penetration study showed that eugenol derivatives are particularly relevant for topical application. The obtained derivatives were characterized by a high level of antioxidant activity estimated after 24 h of conducting the experiment, which indicates long-term protection against reactive oxygen species (ROS) in the deeper layers of the skin.



Author(s):  
Edyta Makuch ◽  
Anna Nowak ◽  
Andrzej Günther ◽  
Robert Pełech ◽  
Łukasz Kucharski ◽  
...  

The main focus of this work is to extend the knowledge about the complexity of issues of oxidative stress. Natural compounds play a serious role in multiple aspects of both human, leading to clear health-promoting effects. This work is focused on the potential application cosmetic formulations containing including but not limited to of clove water and isolated clove oils on their aid in the control of the diseases. The aim of our work was to prepare to evaluate cosmetic formulations containing clove oil, eugenol or new eugenol ester derivative (eugenyl dichloroacetate - EDChA) but also cosmetic formulations containing the aqueous phase obtained after separation of essential oil following the clove buds steam distillation. To evaluate the antioxidants transdermal delivery system, in vitro permeation experiments in a Franz diffusion cell were performed using pig skin. The antioxidative capacity of the cosmetic formulations obtained was determined by the DPPH free radical reduction method. In the next stage, the antioxidant activity (DPPH, ABTS, and Folin–Ciocalteu methods) of the fluid that penetrated through pig skin and of the fluid obtained after skin extraction, were also evaluated. For comparison, studies of cosmetic formulation containing alone dichloroacetic acid (DChAA) were as well carried out. The obtained cosmetic formulations were characterized by of antioxidant activity estimated after 24 hours of conducting the experiment, which indicates long-term protection against reactive oxygen species (ROS) in the deeper layers of the skin. The results of this work contribute to the development of cosmetic formulations with antioxidant potential, emphasizing that the water phases are waste from the process of cloves steam distillation and are not used to prepare cosmetic formulations. The use of waste water from the clove buds steam distillation process is environmentally friendly and not allows us to waste, containing however valuable biologically active compounds (furfural, methyl salicylate, 4-allilofenol, eugenol, α- and β-caryophyllene, eugenyl acetate, β-caryophyllene oxide). Together, these results suggest that cosmetic formulations may be potential drug candidates for chemopreventive, antineoplastic and antimutagenic therapy.



2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
G. Kiran ◽  
T. Maneshwar ◽  
Y. Rajeshwar ◽  
M. Sarangapani

A series of β-Isatin aldehyde-N,N′-thiocarbohydrazone derivatives were synthesized and assayed for theirin vitroantimicrobial and antioxidant activity. The new compounds were characterized based on spectral (FT-IR, NMR, MS) analyses. All the test compounds possessed a broad spectrum of activity having MIC values rangeing from 12.5 to 400 μg/ml against the tested microorganisms. Among the compounds3e,3jand3nshow highest significant antimicrobial activity. The free radical scavenging effects of the test compounds against stable free radical DPPH (α,α-diphenyl-β-picryl hydrazyl) and H2O2were measured spectrophotometrically. Compounds3j,3n,3l, and3e, respectively, had the most effective antioxidant activity against DPPH and H2O2scavenging activity.



2017 ◽  
Vol 9 (4) ◽  
pp. 615
Author(s):  
Mukesh Kumar Yadav ◽  
Santosh Kumar Singh ◽  
JS Tripathi ◽  
YB Tripathi

<p><em>Centella asiatica</em> also known as <em>mandukparni </em>or Indian pennywort or <em>jalbrahmi</em>, which has been used as a medicine in the Ayurveda from ancient times and mentioned in many classical texts of Ayurveda. <em>Centella asiatica</em> has long been used to improve memory and cognitive function.</p><p>The study aimed to identify the phytochemicals present in different solvent extracts of <em>Centella asiatica </em>(i.e. PECA- Petroleum ether extract of <em>C. asiatica, </em>CCA- Chloroform extract of <em>C. asiatica, </em>EACA- Ethyl acetate extract of <em>C. asiatica,</em> ECA- Ethanolic extract of <em>C. asiatica, </em>HACA- Hydro-alcoholic extract of <em>C. asiatica</em>)<em> </em>and evaluate the respective in-vitro antioxidant potentials. <em></em></p><p>The phytochemical screening of extracts was done with standardized procedures and the antioxidant potential of different solvent extracts of <em>Centella asiatica</em> was assessed by its free radical scavenging activity 2, 2-diphenyl -1- picrylhydrazyl (DPPH) as well as hydrogen peroxide scavenging assay respectively for reducing capability.</p><p>In all different solvent extracts of <em>C. asiatica</em> revealed excellent free radical scavenging activity as revealed by 2-2- diphenyl-1-picryl-hydrazyl (DPPH) assay with  EC<sub>50</sub> values for ECA=128.752±1.85 μg/ml, HACA=274.884±1.21 μg/ml and hydrogen peroxide assay against the standard (Butylated hydroxytoluene) BHT, with the EC<sub>50</sub> values ECA=429.69±0.92 μg/ml HACA=458.08±0.58 μg/ml while rest solvent extracts shown very less antioxidant activity.</p><p> The present study indicates that the <em>Centella asiatica</em> extracts have good antioxidant activity which can be used in stress and anxiety and also a good source to be used as natural drugs.</p>



2019 ◽  
Vol 123 (3) ◽  
pp. 241-254 ◽  
Author(s):  
T. Ruskovska ◽  
V. Maksimova ◽  
D. Milenkovic

AbstractOxidative damage of cells and tissues is broadly implicated in human pathophysiology, including cardiometabolic diseases. Polyphenols, as important constituents of the human diet and potent in vitro free radical scavengers, have been extensively studied for their beneficial effects on cardiometabolic health. However, it has been demonstrated that the in vivo antioxidant activity of polyphenols is distinct from their in vitro free radical-scavenging capacity. Indeed, bioavailability of nutritional polyphenols is low and conditioned by complex mechanisms of absorption, distribution, metabolism and excretion. Nowadays, it is commonly accepted that the cellular antioxidant activity of polyphenols is mainly carried out via modification of transcription of genes involved in antioxidant defence. Importantly, polyphenols also contribute to cardiometabolic health by modulation of a plethora of cellular processes that are not directly associated with antioxidant enzymes, through nutri(epi)genomic mechanisms. Numerous human intervention studies have demonstrated beneficial effects of polyphenols on the key cardiometabolic risk factors. However, inconsistency of the results of some studies led to identification of the inter-individual variability in response to consumption of polyphenols. In perspective, a detailed investigation of the determinants of this inter-individual variability will potentially lead us towards personalised dietary recommendations. The phenomenon of inter-individual variability is also of relevance for supplementation with antioxidant (pro)vitamins.



2010 ◽  
Vol 5 (2) ◽  
pp. 224-230 ◽  
Author(s):  
Boobalan Raja ◽  
Kodukkur Pugalendi

AbstractIn this study, an aqueous extract of leaves from Melothria maderaspatana was tested for in vitro antioxidant activity. Free radical scavenging assays, such as hydroxyl radical, hydrogen peroxide, superoxide anion radical and 2,2-diphenyl-1-picryl hydrazyl (DPPH), 2,2’-azinobis-(3-ethyl-enzothiazoline-6-sulfonic acid) (ABTS) radical scavenging, and reducing power assay, were studied. The extract effectively scavenged hydroxyl radical, hydrogen peroxide and superoxide anion radicals. It also scavenged DPPH and ABTS radicals. Furthermore, it was found to have reducing power. All concentrations of leaf extract exhibited free radical scavenging and antioxidant power, and the preventive effects were in a dose-dependent manner. The antioxidant activities of the above were compared to standard antioxidants such as butylated hydroxytoluene (BHT), ascorbic acid, and α-tocopherol. The results obtained in the present study indicate that the M. maderaspatana extract could be considered a potential source of natural antioxidant.



2008 ◽  
Vol 56 (24) ◽  
pp. 11694-11699 ◽  
Author(s):  
Anika E. Wagner ◽  
Patricia Huebbe ◽  
Tetsuya Konishi ◽  
M. Mamunur Rahman ◽  
Meiko Nakahara ◽  
...  


2014 ◽  
Vol 6 (3) ◽  
pp. 543-552 ◽  
Author(s):  
N. Jahan ◽  
M. S. Parvin ◽  
A. Khan ◽  
N. Das ◽  
M. S. Islam ◽  
...  

Pterygota alata is a large deciduous tree of Malvaceae family. The present study was designed to evaluate in vitro antioxidant activity of stem bark of the plant. Ferric reducing power (FRP) test, 1, 1- diphenyl-2-picryl hydrazyl (DPPH) free radical scavenging test and total antioxidant capacity (TAC) assay were used to detect the antioxidant activity. Total phenolic and flavonoid contents were also determined as they are well known phytochemicals with antioxidant property. The bark of the plant showed efficient reducing power as well as free radical scavenging property (IC50 values 52.25 - 172.05). The bark also found rich in total phenolic and flavonoid content. The highest amount of total phenolic content was found in chloroform soluble fraction (29.898 µg/mL) followed by ethyl acetate soluble fraction (15.88 µg/mL). The highest content of total flavonoid also detected in chloroform soluble fraction (107.56 µg/mL) but followed by crude ethanol extract (98.66 µg/mL). Overall, the bark of the plant possesses significant antioxidant activity, therefore can be used as a good natural source of antioxidant. © 2014 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved. doi: http://dx.doi.org/10.3329/jsr.v6i3.17586 J. Sci. Res. 6 (3), 543-552 (2014)



Author(s):  
Shubharani Ramnath ◽  
Sivaram Venkataramegowda

Antioxidants from the natural products are essential to prevent the progression of free radical mediated diseases. In the present study, ethanol extract of propolis collected from different geographical origin were evaluated for their free radical scavenging potential by employing different in-vitro assays such as DPPH, ABTS, Nitric oxide and Hydrogen peroxide. All the tested samples contained considerable amount of total phenols and vitamin C content. In the entire assay, the percentage of inhibition increased with the increase in concentration. Among the propolis samples collected, the highest activity was found in Tamil Nadu, Kerala, Karnataka and Haryana. The difference in the antioxidant activity level was obtained from the assay may reflect a relative difference in the ability of antioxidant compounds to scavenge different free radicals in the extract. Phenols and vitamin C are the major contributors to antioxidant activity in propolis. The propolis from these locations may be of considerable interest in preventing the ill effects of excessive free radical generation in the human body.



Author(s):  
Bindhu R. Kamath ◽  
Sabeena Kizhedath

Background: The use of medicinal plants for maintaining good health is getting attention worldwide. Antioxidants play an important role to protect damage caused by oxidative stress. In the present study methanolic extracts of Cassia fistula  was determined using DPPH for its antioxidant activity. Phytochemical investigation confirmed the presence of bioactive ingredients in the extract.Methods: The antioxidant activity of methanolic extract of Cassia fistula was evaluated using DPPH free radical assay. DPPH (1,1-diphenyl-2-picrylhydrazyine) free radical analysis is one of the accurate and frequently employed method for evaluating antioxidant activity.Results: The methanolic extracts showed increase in radical scavenging activity as concentration increases. The IC50 values were calculated for the methanolic extract. Ascorbic acid was used as control. Cassia fistula exhibited IC 50 of 79.42µg/ml.Conclusions: Scientific evidence suggests that antioxidants reduce the risk for chronic diseases including cancer and heart disease and infectious diseases. Further evaluation of pharmacological activities of Cassia fistula may prove useful in treatment of cancer and heart diseases.



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