Enhancement of the antioxidant and skin permeation properties of eugenol by the esterification of eugenol to new derivat
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ORIGINAL ARTICLE
Open Access
Enhancement of the antioxidant and skin permeation properties of eugenol by the esterification of eugenol to new derivatives Edyta Makuch1* , Anna Nowak2*, Andrzej Günther1, Robert Pełech1, Łukasz Kucharski2, Wiktoria Duchnik2 and Adam Klimowicz2
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. Keywords: Eugenol, New esters of eugenol, log P, Skin penetration, Franz cell, Antioxidant activity Key points • New esters of eugenol show potent antioxidant activity in vitro. • There are new eugenol derivatives to penetrate easily through biological membranes. *Correspondence: [email protected]; [email protected] 1 Department of Chemical Organic Technology and Polymeric Materials, Faculty of Chemical Technology and Engineering, West Pomeranian University of Technology, Szczecin, Pulaskiego 10, 70–322 Szczecin, Poland 2 Department of Cosmetic and Pharmaceutical Chemistry, Pomeranian Medical University in Szczecin, Powstańców Wielkopolskich Ave. 72, 70–111 Szczecin, Poland
• Presented esters can provide exogenous and endogenous action against free radicals.
Introduction Reactive oxygen species (ROS) are important factors in the ageing process that are formed during incomplete reduction of oxygen molecules in the respiratory chain. When there is an imbalance between reactive oxygen species and the body’s antioxidant potential, oxidative stress occurs. It is widely recognized that reactive oxygen species (ROS) contribute to the aging of the skin, which is the external barrier of our body. However, many
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