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Polyhydroxy-2,3-diarylxanthones as antioxidants

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Detalhes bibliográficos
Resumo:Xanthones are a class of oxygenated heterocyclic compounds widely occurring in nature.[1] The biological properties of these compounds have been extensively reported in the literature and one of the most promising is their potential application as antioxidant agents.[2] This fact led us to start a programme on the synthesis of 2,3-diarylxanthones bearing hydroxyl groups in certain positions of their skeleton for further structure- antioxidant activity studies. In this communication we will describe the synthesis of 2,3-diarylxanthones starting with 2’-hydroxyacetophenone and cinnamic acid derivatives (Scheme 1). The Heck reaction of 3-bromo-2-styrylchromones 3 with styrenes give the methoxyxanthones 4 which, after cleavage of the protecting groups, give the desired polyhydroxy-2,3-diarylxanthones 5.[3] We will also report the inhibitory effect of the synthesized xanthones 5 on Cu2+-induced oxidation of isolated human serum low-density lipoproteins (LDLs). The formation of conjugated dienes and the consumption of carotenoids were chosen as markers of LDL lipid peroxidation.[4] The induction of oxidative stress studies in NCTC 2544 cells will also be presented.
Autores principais:Santos, Clementina M.M.
Outros Autores:Morlière, Patrice; Silva, Artur; Maziére, Jean-Claude; Cavaleiro, José; Santus, René
Assunto:Diarylxanthones LDL Copper oxidation Oxidative stress
Ano:2008
País:Portugal
Tipo de documento:documento de conferência
Tipo de acesso:acesso aberto
Instituição associada:Instituto Politécnico de Bragança
Idioma:inglês
Origem:Biblioteca Digital do IPB
Descrição
Resumo:Xanthones are a class of oxygenated heterocyclic compounds widely occurring in nature.[1] The biological properties of these compounds have been extensively reported in the literature and one of the most promising is their potential application as antioxidant agents.[2] This fact led us to start a programme on the synthesis of 2,3-diarylxanthones bearing hydroxyl groups in certain positions of their skeleton for further structure- antioxidant activity studies. In this communication we will describe the synthesis of 2,3-diarylxanthones starting with 2’-hydroxyacetophenone and cinnamic acid derivatives (Scheme 1). The Heck reaction of 3-bromo-2-styrylchromones 3 with styrenes give the methoxyxanthones 4 which, after cleavage of the protecting groups, give the desired polyhydroxy-2,3-diarylxanthones 5.[3] We will also report the inhibitory effect of the synthesized xanthones 5 on Cu2+-induced oxidation of isolated human serum low-density lipoproteins (LDLs). The formation of conjugated dienes and the consumption of carotenoids were chosen as markers of LDL lipid peroxidation.[4] The induction of oxidative stress studies in NCTC 2544 cells will also be presented.