Anti-Hepatocellular Carcinoma (HepG2) Activities of Monoterpene Hydroxy Lactones Isolated from the Marine Microalga Tisochrysis Lutea
| Autor: | Luísa Barreira, Helena Gaspar, João Varela, F. Xavier Malcata, Hugo Pereira, Maria João Rodrigues, Katkam N. Gangadhar |
|---|---|
| Přispěvatelé: | Faculdade de Engenharia |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
0106 biological sciences
Carcinoma Hepatocellular Cell Survival Hepatocellular carcinoma Monoterpene Tisochrysis lutea Pharmaceutical Science Antineoplastic Agents 01 natural sciences Article Lactones 03 medical and health sciences chemistry.chemical_compound Column chromatography loliolide Drug Discovery Microalgae Humans Fucoxanthin lcsh:QH301-705.5 Pharmacology Toxicology and Pharmaceutics (miscellaneous) Carotenoid Benzofurans 030304 developmental biology chemistry.chemical_classification 0303 health sciences Molecular Structure Liver Neoplasms Loliolide Hep G2 Cells hepatocellular carcinoma Thin-layer chromatography lcsh:Biology (General) Biochemistry chemistry Docosahexaenoic acid Monoterpenes Lactone 010606 plant biology & botany Polyunsaturated fatty acid |
| Zdroj: | Marine Drugs Volume 18 Issue 11 Repositório Científico de Acesso Aberto de Portugal Repositório Científico de Acesso Aberto de Portugal (RCAAP) instacron:RCAAP Marine Drugs, Vol 18, Iss 567, p 567 (2020) |
| ISSN: | 1660-3397 |
| DOI: | 10.3390/md18110567 |
| Popis: | Tisochrysis lutea 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, T. lutea 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 (1) and epi-loliolide (2), isolated for the first time in this species. The structural elucidation of both compounds was carried out by GC-MS and 1D (1H and 13C 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 epi-loliolide was found to be more active than loliolide. FCT, Portugal: UID/Multi/04326/2019, UID/MAR/04292/2020 (MARE), UID/Multi/04046/2020 (BioISI) and from the grant of 0055 ALGARED +5E—INTERREG V-A; SFRH/BD/116604/2016; SFRH/BD/105541/2014 info:eu-repo/semantics/publishedVersion |
| Databáze: | OpenAIRE |
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