Novel insights for permeant lead structures through in vitro skin diffusion assays of Prunus lusitanica L., the Portugal Laurel

Costa, Maria do Céu; Duarte, Patrícia; Neng, N. R.; Nogueira, J. M. F.; Costa, M. Filomena; Rosado, Catarina

http://hdl.handle.net/10400.9/2953

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Abstract(s)

As a contribution for the generation of libraries in which a natural product (NP) is used as the guiding structure, this work sought to investigate molecular features of triterpenes as deliver leads to cross the stratum corneum at a significant rate. Seeking a bioguided investigation of the dermocosmetic lead-like potential of triterpenes in Prunus lusitanica L., various extracts were obtained by two different methods (Soxhlet extractor and Accelerated Solvent Extraction-ASE) and analyzed by GC–MS and NMR. In vitro assays were conducted to quantify the friedelin 1 and crude plant extract permeation through a membrane of polydimethylsiloxane (PDMS), as well as their skin penetration enhancement capacity using two model molecules, caffeine 19 and ibuprofen 20. Friedelin 1 was identified as the major component (16–77%, GC) with isolated yield of 51% w/w (94%, GC) from Soxhlet residue (1.7% p/p) of the dried aerial parts of the plant harvested when in early flowering stage. Friedelin 1 promoted the penetration of the lipophilic molecule 20, however, it did not influence the permeation of the hydrophilic permeant 20. On the other hand, the crude extract acted as a retardant of the penetration of both substances. Molecular characteristics for the applicability of P. lusitanica L. in the development of dermocosmetics, as well as a new potential use for friedelin 1 in particular, are demonstrated. Probable mechanisms for chemical penetration enhancement using triterpenes as models for transdermal administration are herein discussed.

Keywords

Natural products Prunus lusitanica L.

URI

http://hdl.handle.net/10400.9/2953

Citation

Costa, M. do Céu; Duarte, P.; Neng, N.R. [et.al.]. - Novel insights for permeant lead structures through in vitro skin diffusion assays of Prunus lusitanica L., the Portugal Laurel. In: Journal of Molecular Structure, 2015, Vol. 1079, p. 327-336