Departamento de Farmacología, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782, Santiago de Compostela, Spain.
Present adress, Applied Phycology-Mycology Group (PMA), Applied Botany Laboratory, Department of Biology, Faculty of Sciences, Abdelmalek Essaâdi University, 93030, Tétouan, Morocco.
Chem Biodivers. 2020 Jul;17(7):e2000121. doi: 10.1002/cbdv.202000121. Epub 2020 Jun 23.
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.
卡拉胶是一种富含（多）酚类化合物的褐藻，具有重要的细胞毒性和抗氧化作用。然而，其化学成分与其作用之间的关系尚不清楚。本研究旨在鉴定其主要作用的潜在化合物和机制。将藻类依次用正己烷、二氯甲烷和甲醇提取，然后根据需要用 Sephadex LH-20 和硅胶柱进一步分馏。将各馏分进行薄层色谱和液相色谱-质谱分析，并测定其总酚含量（福林-肖卡尔特法）、自由基清除活性（DPPH 法）、细胞毒性活性（SH-SY5Y 细胞系 MTT 法）和产生 H O 的能力（Amplex Red 法）。各馏分的色谱和酚类分析表明，所有馏分中均存在大量的氧化还原活性酚类，而极性较小的馏分中则存在大量的类异戊二烯基氢醌衍生物。在正己烷和二氯甲烷馏分中，细胞毒性和抗氧化活性与其酚类含量密切相关，而在甲醇馏分中，细胞毒性与酚类含量呈负相关，抗氧化活性与酚类含量呈正相关。在相同的测试中，氢醌表现出较强的细胞毒性和抗氧化作用。H O 测定表明，卡拉胶的馏分和氢醌可以自动氧化并产生 H O 。我们的结果表明，氧化还原活性酚类产生了卡拉胶所描述的药理作用，而类异戊二烯基氢醌衍生物的氢醌部分负责极性较小馏分的细胞毒性（通过其自动氧化产生的促氧化机制）和抗氧化作用。
