Preparação e avaliação farmacológica de derivados dos lipídios fenólicos do líquido da casca da castanha de caju

AUTOR(ES)

Wellington Alves Gonzaga

DATA DE PUBLICAÇÃO

2008

RESUMO

The present work describes the utilization of Cashew Nut-Shell Liquid (CNSL), abundant source of phenolic non-isoprenoids lipids from our country, as raw material for preparation of compounds with synthetic applications as well as biological useful. The extraction, separation and characterization of CNSL phenolic nonisoprenoids lipids were done by procedures well-known in our research group. Moderates modifications (e.g. hydrogenation, acetylation, metylation) were accomplished on functional groups of anacardic acids and cardanols. Additionally, were done more complex modifications aiming the preparation of 4-hydroxycoumarin derivatives. The natural lipids, all intermediates and derivatives involved at this study were purified by chromatographic column or recrystalization, and characterization by spectrometric methods (IR, 1H and 13C NMR). Simultaneously, all substances were submitted to biological assays. By Artemia salina assay only saturated anacardic acid shown activity (DL50 0,252 ppm). The other CNSL derivatives were not evaluated Artemia salina test because they were not soluble on the assay conditions. The reduction phosphomolybdenum complex assay was done by a modification on Prietos method. For validation and construction of standard curve, salicylic acid, BHT and quercetin were used as standard. Among all assayed compounds, 1-(2- hydroxi-4-pentadecyl) acetophenone (46), methyl 2-hydroxi-6- pentadecylbenzoate (48), 2-(acetyloxy)-6-pentadecylbenzoic acid (49) and anacardyl acetate (32) exhibited antioxidant property similar to BHT. In relation to the fotoproctetion activity the methyl ester of anacardic acid exhibited best result on UVB region. By ex vivo cellular inhibition assay using OSCC, the compounds 46, 49 and 32 showed activity. On the other hand, the assay with MCF-7 cells the 3-pentadecylphenol, methyl 2-hydroxi-6-pentadecylbenzoate and CNSL exhibited better activity.

ASSUNTO(S)

modificações químicas testes biológicos/farmacológicos phenolic lipids and biological/pharmacological assays 4-hydroxicoumarin ciencias da saude lipídeos fenólicos cnsl chemical modifications lcc derivados 4- hidroxicumarínicos

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