Next Article in Journal
The Effect of Microwave Pretreatment on Micronutrient Contents, Oxidative Stability and Flavor Quality of Peanut Oil
Next Article in Special Issue
A New Class of Synthetic Flavonolignan-Like Dimers: Still Few Molecules, but with Attractive Properties
Previous Article in Journal
Optimization of the Steam Explosion Pretreatment Effect on Total Flavonoids Content and Antioxidative Activity of Seabuckthom Pomace by Response Surface Methodology
Previous Article in Special Issue
O-Aminoalkyl-O-Trimethyl-2,3-Dehydrosilybins: Synthesis and In Vitro Effects Towards Prostate Cancer Cells
Open AccessArticle

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

1
Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, 775 15 Olomouc, Czech Republic
2
Regional Centre of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacký University, tř. 17 listopadu 12, 771 46 Olomouc, Czech Republic
3
KTH Royal Institute of Technology, School of Engineering Sciences in Chemistry, Biotechnology and Health, Department of Theoretical Chemistry & Biology, S-106 91 Stockholm, Sweden
4
Department of Plastic and Aesthetic Surgery, University Hospital Olomouc, I. P. Pavlova 6, 779 00 Olomouc, Czech Republic
5
Institute of Microbiology, Laboratory of Biotransformation, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20 Prague, Czech Republic
*
Author to whom correspondence should be addressed.
The contribution as the first author was equal.
Molecules 2019, 24(1), 61; https://doi.org/10.3390/molecules24010061
Received: 6 December 2018 / Revised: 20 December 2018 / Accepted: 21 December 2018 / Published: 24 December 2018
(This article belongs to the Special Issue Silymarin and Derivatives: From Biosynthesis to Health Benefits)
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 Pow 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 Pow 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. View Full-Text
Keywords: Silybum marianum; flavonolignans; flavonoids; experimental and computational hydrophobicity; theoretical lipid membrane models; skin intake Silybum marianum; flavonolignans; flavonoids; experimental and computational hydrophobicity; theoretical lipid membrane models; skin intake
Show Figures

Graphical abstract

MDPI and ACS Style

Kosina, P.; Paloncýová, M.; Rajnochová Svobodová, A.; Zálešák, B.; Biedermann, D.; Ulrichová, J.; Vostálová, J. Dermal Delivery of Selected Polyphenols from Silybum marianum. Theoretical and Experimental Study. Molecules 2019, 24, 61.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop