Redox-Active Phenolic Compounds Mediate the Cytotoxic and Antioxidant Effects of Carpodesmia tamariscifolia (=Cystoseira tamariscifolia).

Carpodesmia tamariscifolia is a brown alga rich in (poly)phenols with important cytotoxic and antioxidant effects. However, the relationship between its chemical composition and its effects is unknown. The aim of this study is to identify the potential compounds and mechanisms responsible for its main effects. The alga was extracted consecutively with hexane, dichloromethane and methanol and further fractionated using Sephadex LH-20 and silica gel columns when appropriate. The fractions were subjected to thin-layer chromatography and liquid chromatography-mass spectrometry analysis and evaluated for their total phenolic content (Folin-Ciocalteu assay), radical scavenging activity (DPPH assay), cytotoxic activity (MTT assay on the SH-SY5Y cell line), and ability to generate H O (Amplex Red assay). Chromatographic and phenolic analyses of the fractions indicate that abundant redox-active phenols are present in all the fractions and that a high amount of prenylated hydroquinone derivatives is present in the apolar ones. In the hexane and dichloromethane fractions, the cytotoxic and antioxidant activities are closely related to their phenolic content, whereas in the methanol fractions, the cytotoxicity is negatively related to the phenolic content and the antioxidant activity is positively related to it. In the same tests, hydroquinone behaves as both strong cytotoxic and antioxidant agent. H O assay shows that C. tamariscifolia fractions and hydroquinone can autoxidize and generate H O . Our results suggest that redox-active phenols produce the pharmacological effects described for C. tamariscifolia and that the hydroquinone moiety of prenylated hydroquinone derivatives is responsible for both cytotoxic (through a pro-oxidant mechanism secondary to its autoxidation) and antioxidant effects of the apolar fractions.