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

2020-11-19Journal article Open access
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datacite.subject.fosCiências Médicas::Ciências da Saúde
datacite.subject.sdg12:Produção e Consumo Sustentáveis
datacite.subject.sdg13:Ação Climática
datacite.subject.sdg14:Proteger a Vida Marinha
dc.contributor.authorGangadhar, Katkam N.
dc.contributor.authorRodrigues, Maria João
dc.contributor.authorPereira, Hugo
dc.contributor.authorGaspar, Helena
dc.contributor.authorMalcata, F. Xavier
dc.contributor.authorBarreira, Luísa
dc.contributor.authorVarela, João
dc.date.accessioned2025-07-18T17:03:51Z
dc.date.available2025-07-18T17:03:51Z
dc.date.issued2020-11-19
dc.descriptionArticle number - 567
dc.description.abstractTisochrysis 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 (1 H and13 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 epi-loliolide was found to be more active than loliolide. © 2020 by the authors.eng
dc.description.sponsorshipFunding: The present work was funded by the Foundation for Science and Technology (FCT, Portugal) under the projects of the 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 España-Portugal. K.N.G is an auxiliary researcher (Decree-Law no. 57/2016 as amended by Law No 57/2017) funded by University of Algarve. FCT also funded M.J.R (SFRH/BD/116604/2016) and H.P. (SFRH/BD/105541/2014). Acknowledgments: We would like to acknowledge NECTON S.A, Portugal, for kindly supplying T. lutea biomass. We also thank Vera Marques and Nuno Santos, CBME, University of Algarve (Portugal) for providing the hepatocellular carcinoma (HepG2) and non-tumoral murine bone marrow stromal (S17) cell lines, respectively.
dc.identifier.citationGangadhar, K. N., Rodrigues, M. J., Pereira, H., Gaspar, H., Malcata, F. X., Barreira, L., & Varela, J. (2020). Anti-Hepatocellular Carcinoma (HepG2) Activities of Monoterpene Hydroxy Lactones Isolated from the Marine Microalga Tisochrysis Lutea. Marine Drugs, 18(11), 567. https://doi.org/10.3390/md18110567.
dc.identifier.doi10.3390/md18110567
dc.identifier.issn1660-3397
dc.identifier.urihttp://hdl.handle.net/10400.8/13723
dc.language.isoeng
dc.peerreviewedyes
dc.publisherMDPI
dc.relationCentre of Marine Sciences
dc.relation.hasversionhttps://www.mdpi.com/1660-3397/18/11/567
dc.relation.ispartofMarine Drugs
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectTisochrysis lutea
dc.subjectloliolide
dc.subjecthepatocellular carcinoma
dc.titleAnti-Hepatocellular Carcinoma (HepG2) Activities of Monoterpene Hydroxy Lactones Isolated from the Marine Microalga Tisochrysis Luteaeng
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleCentre of Marine Sciences
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UID%2FMulti%2F04326%2F2019/PT
oaire.citation.endPage10
oaire.citation.issue11
oaire.citation.startPage1
oaire.citation.titleMarine Drugs
oaire.citation.volume18
oaire.fundingStream6817 - DCRRNI ID
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85
person.familyNameGuerreiro Galla Gaspar
person.givenNameHelena Margarida
person.identifierE-6798-2012
person.identifier.ciencia-id761C-044C-995B
person.identifier.orcid0000-0002-1613-7023
person.identifier.scopus-author-id7003891380
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
relation.isAuthorOfPublication580efc75-e17e-4380-ae50-e5bc1d0bc10d
relation.isAuthorOfPublication.latestForDiscovery580efc75-e17e-4380-ae50-e5bc1d0bc10d
relation.isProjectOfPublication9105577c-d1db-4d3e-a3d0-28c9b3daad56
relation.isProjectOfPublication.latestForDiscovery9105577c-d1db-4d3e-a3d0-28c9b3daad56

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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 (1 H and13 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 epi-loliolide was found to be more active than loliolide. © 2020 by the authors.
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