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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, Skolan för kemi, bioteknologi och hälsa (CBH), Teoretisk kemi och biologi. 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 (Engelska)Ingår i: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 24, nr 1, artikel-id 61Artikel i tidskrift (Refereegranskat) 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.

Ort, förlag, år, upplaga, sidor
MDPI , 2019. Vol. 24, nr 1, artikel-id 61
Nyckelord [en]
Silybum marianum, flavonolignans, flavonoids, experimental and computational hydrophobicity, theoretical lipid membrane models, skin intake
Nationell ämneskategori
Kemi
Identifikatorer
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
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QC 20190218

Tillgänglig från: 2019-02-18 Skapad: 2019-02-18 Senast uppdaterad: 2019-02-18Bibliografiskt granskad

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Kosina, PavelPaloncyova, Marketa
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