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Article

Anti-Hepatocellular Carcinoma (HepG2) Activities of Monoterpene Hydroxy Lactones Isolated from the Marine Microalga Tisochrysis Lutea

1
Centre of Marine Sciences, Faculty of Sciences and Technology, University of Algarve, Campus of Gambelas, 8005-139 Faro, Portugal
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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
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Green Colab-Associação Oceano Verde, Universidade do Algarve, Campus de Gambelas, 8005-139 Faro, Portugal
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BioISI—Biosystems & Integrative Sciences Institute, Faculty of Sciences, University of Lisbon, Campo Grande, C8, 1749-016 Lisbon, Portugal
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MARE—Marine and Environmental Sciences Centre, Polytechnic of Leiria, Edifício CETEMARES, Avenida do Porto de Pesca, 2520-630 Peniche, Portugal
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2020, 18(11), 567; https://doi.org/10.3390/md18110567
Received: 26 October 2020 / Revised: 9 November 2020 / Accepted: 16 November 2020 / Published: 19 November 2020
(This article belongs to the Special Issue Bioactive Compounds Derived from Marine Microalgae 2.0)
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. View Full-Text
Keywords: Tisochrysis lutea; loliolide; hepatocellular carcinoma Tisochrysis lutea; loliolide; hepatocellular carcinoma
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MDPI and ACS Style

Gangadhar, K.N.; Rodrigues, M.J.; Pereira, H.; Gaspar, H.; Malcata, F.X.; Barreira, L.; Varela, J. Anti-Hepatocellular Carcinoma (HepG2) Activities of Monoterpene Hydroxy Lactones Isolated from the Marine Microalga Tisochrysis Lutea. Mar. Drugs 2020, 18, 567. https://doi.org/10.3390/md18110567

AMA Style

Gangadhar KN, Rodrigues MJ, Pereira H, Gaspar H, Malcata FX, Barreira L, Varela J. Anti-Hepatocellular Carcinoma (HepG2) Activities of Monoterpene Hydroxy Lactones Isolated from the Marine Microalga Tisochrysis Lutea. Marine Drugs. 2020; 18(11):567. https://doi.org/10.3390/md18110567

Chicago/Turabian Style

Gangadhar, Katkam N., Maria J. Rodrigues, Hugo Pereira, Helena Gaspar, F. X. Malcata, Luísa Barreira, and João Varela. 2020. "Anti-Hepatocellular Carcinoma (HepG2) Activities of Monoterpene Hydroxy Lactones Isolated from the Marine Microalga Tisochrysis Lutea" Marine Drugs 18, no. 11: 567. https://doi.org/10.3390/md18110567

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