Molecules 2013, 18(1), 178-189; doi:10.3390/molecules18010178
Article

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

Received: 26 October 2012; in revised form: 16 November 2012 / Accepted: 20 November 2012 / Published: 24 December 2012
(This article belongs to the Special Issue Antioxidants 2012)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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.
Keywords: ABTS; antioxidants; bioactivity; cytotoxicity; DPPH; natural product derivatives; 4-NC; Piper peltatum; radical scavenger activity; stability
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MDPI and ACS Style

Lima, E.S.; Pinto, A.C.S.; Nogueira, K.L.; Silva, L.F.R.; Almeida, P.D.O.; Vasconcellos, M.C.; Chaves, F.C.M.; Tadei, W.P.; Pohlit, A.M. Stability and Antioxidant Activity of Semi-synthetic Derivatives of 4-Nerolidylcatechol. Molecules 2013, 18, 178-189.

AMA Style

Lima ES, Pinto ACS, Nogueira KL, Silva LFR, Almeida PDO, Vasconcellos MC, Chaves FCM, Tadei WP, Pohlit AM. Stability and Antioxidant Activity of Semi-synthetic Derivatives of 4-Nerolidylcatechol. Molecules. 2013; 18(1):178-189.

Chicago/Turabian Style

Lima, Emerson S.; Pinto, Ana C.S.; Nogueira, Karla L.; Silva, Luiz F.R.; Almeida, Patricia D.O.; Vasconcellos, Marne C.; Chaves, Francisco C.M.; Tadei, Wanderli P.; Pohlit, Adrian M. 2013. "Stability and Antioxidant Activity of Semi-synthetic Derivatives of 4-Nerolidylcatechol." Molecules 18, no. 1: 178-189.

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