Centre of Marine Sciences, Faculty of Sciences and Technology, University of Algarve, Campus of Gambelas, 8005-139 Faro, Portugal.
LEPABE-Laboratory of Engineering of Processes, Environment, Biotechnology and Energy, Department of Chemical Engineering, University of Porto, Rua Dr. Roberto Frias s/n, 4200-465 Porto, Portugal.
Mar Drugs. 2020 Nov 19;18(11):567. doi: 10.3390/md18110567.
is a marine haptophyte rich in omega-3 polyunsaturated fatty acids (e.g., docosahexaenoic acid (DHA)) and carotenoids (e.g., fucoxanthin). Because of the nutraceutical applications of these compounds, this microalga is being used in aquaculture to feed oyster and shrimp larvae. In our earlier report, organic crude extracts exhibited in vitro cytotoxic activity against human hepatocarcinoma (HepG2) cells. However, so far, the compound(s) accountable for the observed bioactivity have not been identified. Therefore, the aim of this study was to isolate and identify the chemical component(s) responsible for the bioactivity observed. Bioassay-guided fractionation through a combination of silica-gel column chromatography, followed by preparative thin layer chromatography (PTLC), led to the isolation of two diastereomers of a monoterpenoid lactone, namely, loliolide () and -loliolide (), isolated for the first time in this species. The structural elucidation of both compounds was carried out by GC-MS and 1D (H and C APT) and 2D (COSY, HMBC, HSQC-ed, and NOESY) NMR analysis. Both compounds significantly reduced the viability of HepG2 cells and were considerably less toxic towards a non-tumoral murine stromal (S17) cell line, although -loliolide was found to be more active than loliolide.
是一种富含 ω-3 多不饱和脂肪酸（如二十二碳六烯酸（DHA））和类胡萝卜素（如岩藻黄质）的海洋甲藻。由于这些化合物具有营养保健品的应用，这种微藻正被用于水产养殖来喂养牡蛎和虾类幼虫。在我们之前的报告中，有机粗提取物对人肝癌（HepG2）细胞表现出体外细胞毒性。然而，到目前为止，负责观察到的生物活性的化合物尚未被确定。因此，本研究的目的是分离和鉴定负责观察到的生物活性的化学成分。通过硅胶柱色谱和制备薄层层析（PTLC）相结合的生物测定指导的分级分离，导致分离出两种单萜内酯的非对映异构体，即，内消旋-贝壳杉烯内酯（）和 -贝壳杉烯内酯（），这两种化合物均为首次在该物种中分离得到。通过 GC-MS 以及 1D（H 和 C APT）和 2D（COSY、HMBC、HSQC-ed 和 NOESY）NMR 分析对两种化合物的结构进行了阐明。这两种化合物均显著降低了 HepG2 细胞的活力，并且对非肿瘤鼠基质（S17）细胞系的毒性要小得多，尽管 -贝壳杉烯内酯比内消旋-贝壳杉烯内酯更具活性。
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