Stability and Antioxidant Activity of Semi-synthetic Derivatives of 4-Nerolidylcatechol.

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 (IC50 = 31.4 µM) and more unstable than its derivatives and lost more than 80% of its antioxidant activity upon storage in solution at −20 °C 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 °C, 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.

Bibliographic Details

Main Authors:	LIMA, E. S., PINTO, A. C. S., NOGUEIRA, K. L., SILVA, L. F. R. e, ALMEIDA, P. D. O. de, VASCONCELLOS, M. C. de, CHAVES, F. C. M., TADEI, W. P., POHLIT, A. M.
Other Authors:	Emerson Silva Lima, UFAM; Ana Cristina Silva Pinto, INPA; Karla Lagos Nogueira, INPA; Luiz Francisco Rocha e Silva, INPA; Patricia Danielle Oliveira de Almeida, UFAM; Marne Carvalho de Vasconcellos, UFAM; FRANCISCO CELIO MAIA CHAVES, CPAA; Wanderli Pedro Tadei, INPA; Adrian Martin Pohlit, INPA.
Format:	Separatas biblioteca
Language:	English eng
Published:	2013-04-04
Subjects:	Piper peltatum, Antioxidantes,
Online Access:	http://www.alice.cnptia.embrapa.br/alice/handle/doc/954997
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