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Use of metabolomic and dereplication tools in the study of the chemical composition of some octocorals of the colombian caribbean and their cytotoxic activity
| dc.contributor.advisor | Camacho, Edisson T. | |
| dc.contributor.advisor | Thomas, Olivier P. | |
| dc.contributor.author | Santacruz Cifuentes, Liliana Andrea | |
| dc.date.accessioned | 8/24/2020 10:45 | |
| dc.date.available | 8/24/2020 10:45 | |
| dc.date.issued | 2020-06-11 | |
| dc.identifier.uri | http://hdl.handle.net/10818/42976 | |
| dc.description | 102 páginas | es_CO |
| dc.description.abstract | Los océanos cubren un poco mas de dos terceras partes de la superficie de la tierra y los organismos que en ellos viven constituyen cerca del 2% de la materia orgánica presente en los mares; en particular, las aguas cálidas del Mar Caribe contribuyen a la diversidad de la fauna marina, en donde, los octocorales son la macrofauna arrecifal más visible. Estos organismos, son fuente productiva de una gran diversidad de compuestos químicos los cuales les sirven como defensa química contra depredadores, pero también mucho de ellos han presentado actividades biológicas importantes para combatir diferentes enfermedades; por lo cual, es importante investigar sobre nuevas herramientas de estudio que permitan explorar este gran potencial. Por lo anterior, en este proyecto se estudió la relación de la actividad citotóxica de algunos octocorales del Caribe Colombiano con respecto a su composición metabólica, usando diferentes herramientas como la dereplicación, útil en la identificación temprana de compuestos nuevos o conocidos con actividad biológica, el uso de Redes Moleculares de Productos Naturales (GNPS) que con el uso del software Cytoscape permitió observar “cluster” o agrupaciones de moléculas con patrones de fragmentación similares y finalmente; la herramienta metabolómica, que permitió detectar un gran número de metabolitos presentes en los organismos estudiados. Para el desarrollo de este proyecto, se utilizaron técnicas cromatográficas de alta eficiencia: cromatografía líquida ultra eficiente junto con espectrometría de masas de alta resolución (UPLCHRMS / Agilent 6540) y resonancia magnética nuclear (RMN / Agilent 600 MHz); que ayudó en la determinación del perfil global de los metabolitos presentes en los extractos octocorales; además, en los modelos generados a partir del análisis multivariado de componentes principales (PCA) y análisis discriminantes. | es_CO |
| dc.format | application/pdf | es_CO |
| dc.language.iso | eng | es_CO |
| dc.publisher | Universidad de La Sabana | es_CO |
| dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 International | * |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
| dc.source | Universidad de La Sabana | |
| dc.source | Intellectum Repositorio Universidad de La Sabana | |
| dc.subject | Animales marinos | es_CO |
| dc.subject | Organismos marinos | es_CO |
| dc.subject | Biotecnología molecular | es_CO |
| dc.subject | Resonancia magnética nuclear | es_CO |
| dc.subject | Análisis multivariante | es_CO |
| dc.title | Use of metabolomic and dereplication tools in the study of the chemical composition of some octocorals of the colombian caribbean and their cytotoxic activity | en |
| dc.type | doctoral thesis | es_CO |
| dc.identifier.local | 277707 | |
| dc.identifier.local | TE10735 | |
| dc.type.hasVersion | publishedVersion | es_CO |
| dc.rights.accessRights | openAccess | es_CO |
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| dcterms.references | Chiu, C.Y.; Yeh, K.W.; Lin, G.; Chiang, M.H.; Yang, S.C.; Chao, W.J.; Yao, T.C.; Tsai, M.H.; Hua, M.C.; Liao, S.L.; et al. Metabolomics reveals dynamic metabolic changes associated with age in early childhood. PLoS ONE 2016, 11, e0149823. [CrossRef] [PubMed] | en |
| dcterms.references | Xia, J.; Sinelnikov, I.V.; Han, B.; Wishart, D.S. MetaboAnalyst 3.0—Making metabolomics more meaningful. Nucleic Acids Res. 2015, 43, W251–W257. [CrossRef] [PubMed] | en |
| dcterms.references | Hubert, J.; Nuzillard, J.M.; Renault, J.H. Dereplication strategies in natural product research: How many tools and methodologies behind the same concept? Phytochem. Rev. 2017, 16, 55–95. [CrossRef] | en |
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| dcterms.references | National Center for Biotechnology Information Dolabellatrienone. Available online: https://pubchem.ncbi. nlm.nih.gov/compound/10469260 (accessed on 25 September 2018). | en |
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| dcterms.references | Look, S.A.; Fenical, W. New Bicyclic Diterpenoids from the Caribbean Gorgonian Octocoral Eunicea calyculata. J. Org. Chem. 1982, 47, 4129–4134. [CrossRef] | en |
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| dcterms.references | Gao, Y.; Xiao, W.; Liu, H.C.; Wang, J.R.; Yao, L.G.; Ouyang, P.K.; Wang, D.C.; Guo, Y.W. Clavirolide G, a new rare dolabellane-type diterpenoid from the Xisha soft coral Clavularia viridis. Chin. Chem. Lett. 2017, 28, 905–908. [CrossRef] | en |
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| dcterms.references | Dyshlovoy, S.; Honecker, F. Marine Compounds and Cancer: 2017 Updates. Mar. Drugs 2018, 16, 41. [CrossRef] [PubMed] | eng |
| dcterms.references | Ruiz Torres, V.; Encinar, J.A.; Herranz López, M.; Pérez Sánchez, A.; Galiano, V.; Barrajón Catalán, E.; Micol, V. An updated review on marine anticancer compounds: The use of virtual screening for the discovery of small-molecule cancer drugs. Molecules 2017, 22, 1037. [CrossRef] [PubMed] | eng |
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| dcterms.references | Ojima, I.; Chakravarty, S.; Inoue, T.; Lin, S.; He, L.; Horwitz, S.B.; Kuduk, S.D.; Danishefsky, S.J. A common pharmacophore for cytotoxic natural products that stabilize microtubules. Proc. Natl. Acad. Sci. USA 1999, 96, 4256–4261. [CrossRef] [PubMed] | eng |
| dcterms.references | Correa, H.; Valenzuela, A.L.; Ospina, L.F.; Duque, C. Anti-inflammatory effects of the gorgonian Pseudopterogorgia elisabethae collected at the Islands of Providencia and San Andrés (SW Caribbean). J. Inflamm. 2009, 6, 5. [CrossRef] [PubMed] | eng |
| dcterms.references | Correa, H.; Aristizabal, F.; Duque, C.; Kerr, R. Cytotoxic and antimicrobial activity of pseudopterosins and seco-pseudopterosins isolated from the octocoral Pseudopterogorgia elisabethae of San Andrés and Providencia Islands (Southwest Caribbean Sea). Mar. Drugs 2011, 9, 334–343. [CrossRef] [PubMed] | eng |
| dcterms.references | Marrero, J.; Rodríguez, A.D.; Baran, P.; Raptis, R.G. Ciereszkolide: Isolation and structure characterization of a novel rearranged cembrane from the caribbean sea plume Pseudopterogorgia kallos. Eur. J. Org. Chem. 2004, 3909–3912. [CrossRef] | eng |
| dcterms.references | Look, S.A.; Fenical, W.; Jacobst, R.S.; Clardyt, J.O.N. The pseudopterosins: Anti-inflammatory and analgesic natural products from the sea whip Pseudopterogorgia elisabethae. Proc. Natl. Acad. Sci. USA 1986, 83, 6238–6240. [CrossRef] [PubMed] | eng |
| dcterms.references | Deng, L.; Gu, H.; Zhu, J.; Nagana Gowda, G.A.; Djukovic, D.; Chiorean, E.G.; Raftery, D. Combining NMR and LC/MS using backward variable elimination: Metabolomics analysis of colorectal cancer, polyps, and healthy controls. Anal. Chem. 2016, 88, 7975–7983. [CrossRef] [PubMed] | eng |
| dcterms.references | Lindon, J.C.; Holmes, E.; Bollard, M.E.; Stanley, E.G.; Nicholson, J.K. Metabonomics technologies and their applications in physiological monitoring, drug safety assessment and disease diagnosis. Biomarkers 2004, 9, 1–31. [CrossRef] [PubMed] | eng |
| dcterms.references | Tistaert, C.; Chataigné, G.; Dejaegher, B.; Rivière, C.; Hoai, N.N.; Van, M.C.; Quetin-leclercq, J.; Heyden, Y. Vander Multivariate data analysis to evaluate the fingerprint peaks responsible for the cytotoxic activity of Mallotus species. J. Chromatogr. B 2012, 910, 103–113. [CrossRef] [PubMed] | eng |
| dcterms.references | Leal, M.C.; Madeira, C.; Brandão, C.A.; Puga, J.; Calado, R. Bioprospecting of marine invertebrates for new natural products—A chemical and zoogeographical perspective. Molecules 2012, 17, 9842–9854. [CrossRef] [PubMed] | eng |
| dcterms.references | Wei, X.; Rodríguez, A.D.; Baran, P.; Raptis, R.G. Dolabellane-type diterpenoids with antiprotozoan activity from a southwestern Caribbean gorgonian octocoral of the genus Eunicea. J. Nat. Prod. 2010, 73, 925–934. [CrossRef] [PubMed] | eng |
| dcterms.references | Maille, G.; Qin, C.; Siuzdak, G. Nonlinear Data Alignment for UPLC—MS and HPLC—MS Based Metabolomics: Quantitative Analysis of Endogenous and Exogenous Metabolites in Human Serum. Anal. Chem. 2006, 78, 3289–3295. [CrossRef] | eng |
| dcterms.references | Szymanska, E.; Saccenti, E.; Smilde, A.K.; Westerhuis, J.A. Double-check: Validation of diagnostic statistics for PLS-DA models in metabolomics studies. Metabolomics 2012, 14. [CrossRef] [PubMed] | eng |
| dcterms.references | Rantalainen, M.; Cloarec, O.; Nicholson, J.K.; Holmes, E.; Trygg, J. OPLS discriminant analysis: Combining the strengths of PLS-DA and SIMCA classification. J. Chemiometr. 2006, 20, 341–351. [CrossRef] | eng |
| dcterms.references | Goecks, J.; Nekrutenko, A.; Taylor, J.; Afgan, E.; Ananda, G.; Baker, D.; Blankenberg, D.; Chakrabarty, R.; Coraor, N.; Goecks, J.; et al. Galaxy: A comprehensive approach for supporting accessible, reproducible and transparent computational research in the life sciences. Genome Biol. 2010, 11, 13. [CrossRef] | eng |
| dcterms.references | Haug, K.; Salek, R.M.; Conesa, P.; Hastings, J.; De Matos, P.; Rijnbeek, M.; Mahendraker, T.; Williams, M.; Neumann, S.; Rocca-Serra, P.; et al. MetaboLights—An open-access general-purpose repository for metabolomics studies and associated meta-data. Nucleic Acids Res. 2013, 41, 781–786. [CrossRef] | eng |
| dcterms.references | Hostettman, K. Methods in Plant Biochemistry. Assays for Bioactivity; Academic Press: London, UK, 1991. | eng |
| dcterms.references | Xia, J.; Psychogios, N.; Young, N.; Wishart, D.S. MetaboAnalyst: A web server for metabolomic data analysis and interpretation. Nucleic Acids Res. 2009, 37, 652–660. [CrossRef] [PubMed] | eng |
| dcterms.references | Moltu, S.J.; Sachse, D.; Blakstad, E.W.; Strømmen, K.; Nakstad, B.; Almaas, A.N.; Westerberg, A.C.; Rønnestad, A.; Brække, K.; Veierød, M.B.; et al. Urinary metabolite profiles in premature infants show early postnatal metabolic adaptation and maturation. Nutrients 2014, 6, 1913–1930. [CrossRef] [PubMed] | eng |
| dcterms.references | Chiu, C.Y.; Yeh, K.W.; Lin, G.; Chiang, M.H.; Yang, S.C.; Chao, W.J.; Yao, T.C.; Tsai, M.H.; Hua, M.C.; Liao, S.L.; et al. Metabolomics reveals dynamic metabolic changes associated with age in early childhood. PLoS ONE 2016, 11, e0149823. [CrossRef] [PubMed] | eng |
| dcterms.references | Xia, J.; Sinelnikov, I.V.; Han, B.; Wishart, D.S. MetaboAnalyst 3.0—Making metabolomics more meaningful. Nucleic Acids Res. 2015, 43, W251–W257. [CrossRef] [PubMed] | eng |
| dcterms.references | Hubert, J.; Nuzillard, J.M.; Renault, J.H. Dereplication strategies in natural product research: How many tools and methodologies behind the same concept? Phytochem. Rev. 2017, 16, 55–95. [CrossRef] | eng |
| dcterms.references | National Center for Biotechnology Information Eduenone. Available online: https://pubchem.ncbi.nlm.nih. gov/compound/10424127 (accessed on 25 September 2018). | eng |
| dcterms.references | National Center for Biotechnology Information Dolabellatrienone. Available online: https://pubchem.ncbi. nlm.nih.gov/compound/10469260 (accessed on 25 September 2018). | eng |
| dcterms.references | Wolf, S.; Schmidt, S.; Müller Hannemann, M.; Neumann, S. In silico fragmentation for computer assisted identification of metabolite mass spectra. BMC Bioinform. 2010, 1, 43. [CrossRef] | eng |
| dcterms.references | Look, S.A.; Fenical, W. New Bicyclic Diterpenoids from the Caribbean Gorgonian Octocoral Eunicea calyculata. J. Org. Chem. 1982, 47, 4129–4134. [CrossRef] | eng |
| dcterms.references | Patel, S.; Gheewala, N.; Suthar, A.; Shah, A. In-Vitro cytotoxicity activity of Solanum Nigrum extract against Hela cell line and Vero cell line. Int. J. Pharm. Pharm. Sci. 2009, 1, 38–47. | eng |
| dcterms.references | Gao, Y.; Xiao, W.; Liu, H.C.; Wang, J.R.; Yao, L.G.; Ouyang, P.K.; Wang, D.C.; Guo, Y.W. Clavirolide G, a new rare dolabellane-type diterpenoid from the Xisha soft coral Clavularia viridis. Chin. Chem. Lett. 2017, 28, 905–908. [CrossRef] | eng |
| dcterms.references | Shen, Y.C.; Pan, Y.L.; Ko, C.L.; Kuo, Y.H.; Chen, C.Y. New dolabellanes from the Taiwanese soft coral clavularia inflata. J. Chin. Chem. Soc. 2003, 50, 471–476. [CrossRef] | eng |
| dcterms.references | Chang, K.C.; Duh, C.Y.; Chen, I.S.; Tsai, I.L. A cytotoxic butenolide, two new dolabellane diterpenoids, a chroman and a benzoquinol derivative formosan Casearia membranacea. Planta Med. 2003, 69, 667–672. [CrossRef] [PubMed] | eng |
| dcterms.references | Duh, C.Y.; Chia, M.C.; Wang, S.K.; Chen, H.J.; El-Gamal, A.A.H.; Dai, C.F. Cytotoxic dolabellane diterpenes from the Formosan soft coral Clavularia inflata. J. Nat. Prod. 2001, 64, 1028–1031. [CrossRef] [PubMed] | eng |
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| dcterms.references | Correa, H. Estudios de Bioprospección del coral blando Pseudopterogorgia Elisabethae como Fuente de Sustancias con Actividad Biológica Fase IV. Ph.D. Thesis, National University of Colombia, Bogotá, Colombia, 2012. | es_CO |
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| thesis.degree.discipline | Facultad de Ingeniería | es_CO |
| thesis.degree.level | Doctorado en Biociencias | es_CO |
| thesis.degree.name | Doctor en Biociencias | es_CO |
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