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Dermal Delivery of Selected Polyphenols from Silybum marianum. Theoretical and Experimental Study
Palacky Univ, Fac Med & Dent, Dept Med Chem & Biochem, Hnevotinska 3, Olomouc 77515, Czech Republic..ORCID iD: 0000-0003-1991-1990
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology. Palacky Univ, Fac Sci, Dept Phys Chem, Reg Ctr Adv Technol & Mat, Tr 17 Listopadu 12, Olomouc 77146, Czech Republic..
Palacky Univ, Fac Med & Dent, Dept Med Chem & Biochem, Hnevotinska 3, Olomouc 77515, Czech Republic..
Univ Hosp Olomouc, Dept Plast & Aesthet Surg, IP Pavlova 6, Olomouc 77900, Czech Republic..
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2019 (English)In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 24, no 1, article id 61Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
MDPI , 2019. Vol. 24, no 1, article id 61
Keywords [en]
Silybum marianum, flavonolignans, flavonoids, experimental and computational hydrophobicity, theoretical lipid membrane models, skin intake
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-244139DOI: 10.3390/molecules24010061ISI: 000457150200061PubMedID: 30586949Scopus ID: 2-s2.0-85059244691OAI: oai:DiVA.org:kth-244139DiVA, id: diva2:1289461
Note

QC 20190218

Available from: 2019-02-18 Created: 2019-02-18 Last updated: 2019-02-18Bibliographically approved

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