Dermal Delivery of Selected Polyphenols from Silybum marianum. Theoretical and Experimental Study

0503986 - MBÚ 2020 RIV CH eng J - Článek v odborném periodiku
Kosina, P. - Paloncýová, M. - Svobodová, A.R. - Zálešák, B. - Biedermann, David - Ulrichová, J. - Vostálová, J.
Dermal Delivery of Selected Polyphenols from Silybum marianum. Theoretical and Experimental Study.
Molecules. Roč. 24, č. 1 (2019), č. článku 61. E-ISSN 1420-3049
Institucionální podpora: RVO:61388971
Klíčová slova: Silybum marianum * experimental and computational hydrophobicity * lavonolignans
Obor OECD: Medicinal chemistry
Impakt faktor: 3.267, rok: 2019
Způsob publikování: Open access
https://www.mdpi.com/1420-3049/24/1/61

Silymarin is a well-known standardized extract from the seeds of milk thistle (Silybum marianum L., Asteraceae) with a pleiotropic effect on human health, including skin anticancer potential. Detailed characterization of flavonolignans properties affecting interactions with human skin was of interest. The partition coefficients log P-ow of main constitutive flavonolignans, taxifolin and their respective dehydro derivatives were determined by a High Performance Liquid Chromatography (HPLC) method and by mathematical (in silico) approaches in n-octanol/water and model lipid membranes. These parameters were compared with human skin intake ex vivo. The experimental log P-ow values for individual diastereomers were estimated for the first time. The replacement of n-octanol with model lipid membranes in the theoretical lipophilicity estimation improved the prediction strength. During transdermal transport, all the studied compounds permeated the human skin ex vivo, none of them reached the acceptor liquid. Both experimental/theoretical tools allowed the studied polyphenols to be divided into two groups: low (taxifolin, silychristin, silydianin) vs. high (silybin, dehydrosilybin, isosilybin) lipophilicity and skin intake. In silico predictions can be usefully applied for estimating general lipophilicity trends, such as skin penetration or accumulation predictions. However, the theoretical models cannot yet provide the dermal delivery differences of compounds with very similar physico-chemical properties, e.g., between diastereomers.
Trvalý link: http://hdl.handle.net/11104/0295736