%0 Journal Article
%T Stability and Antioxidant Activity of Semi-synthetic Derivatives of 4-Nerolidylcatechol
%A Emerson Silva Lima
%A Ana Cristina Silva Pinto
%A Karla Lagos Nogueira
%A Luiz Francisco Rocha e Silva
%A Patricia Danielle Oliveira de Almeida
%A Marne Carvalho de Vasconcellos
%A Francisco Celio Maia Chaves
%A Wanderli Pedro Tadei
%A Adrian Martin Pohlit
%J Molecules
%D 2013
%I MDPI AG
%R 10.3390/molecules18010178
%X 4-nerolidylcatechol (4-NC) is an unstable natural product that exhibits important antioxidant, anti-inflammatory and other properties. It is readily obtainable on a multi-gram scale through straightforward solvent extraction of the roots of cultivated Piper peltatum or P. umbellatum, followed by column chromatography on the resulting extract. Semi-synthetic derivatives of 4-NC with one or two substituent groups (methyl, acetyl, benzyl, benzoyl) on the O atoms have been introduced that have increased stability compared to 4-NC and significant in vitro inhibitory activity against the human malaria parasite Plasmodium falciparum. Antioxidant and anti-inflammatory properties may be important for the antiplasmodial mode of action of 4-NC derivatives. Thus, we decided to investigate the antioxidant properties, cytotoxicity and stability of 4-NC derivatives as a means to explore the potential utility of these compounds. 4-NC showed high antioxidant activity in the DPPH and ABTS assays and in 3T3-L1 cells (mouse embryonic fibroblast), however 4-NC was more cytotoxic (IC 50 = 31.4 ¦ÌM) and more unstable than its derivatives and lost more than 80% of its antioxidant activity upon storage in solution at £¿20 ¡ãC for 30 days. DMSO solutions of mono- O-substituted derivatives of 4-NC exhibited antioxidant activity and radical scavenging activity in the DPPH and ABTS assays that was comparable to that of BHA and BHT. In the cell-based antioxidant model, most DMSO solutions of derivatives of 4-NC were less active on day 1 than 4-NC, quercetin and BHA and more active antioxidants than BHT. After storage for 30 days at £¿20 ¡ãC, DMSO solutions of most of the derivatives of 4-NC were more stable and exhibited more antioxidant activity than 4-NC, quercetin and BHA and exhibited comparable antioxidant activity to BHT. These findings point to the potential of derivatives of 4-NC as antioxidant compounds.
%K ABTS
%K antioxidants
%K bioactivity
%K cytotoxicity
%K DPPH
%K natural product derivatives
%K 4-NC
%K Piper peltatum
%K radical scavenger activity
%K stability
%U http://www.mdpi.com/1420-3049/18/1/178