Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)

ilustraciones, diagramas, tablas

Autores:: Gómez López, Karen Daniela

Tipo de recurso:

Fecha de publicación:: 2021

Institución:: Universidad Nacional de Colombia

Repositorio:: Universidad Nacional de Colombia

Idioma:: spa

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repository_id_str
dc.title.spa.fl_str_mv	Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)
dc.title.translated.eng.fl_str_mv	Synthesis of 1-oxo-indane-4-carboxylic acid derivatives and evaluation of their elicitor effect on bioactive isoflavonoids in soybean (Glycine max L)
title	Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)
spellingShingle	Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L) 540 - Química y ciencias afines Isoflavonoide Elicitor Actividad antioxidante Isoflavonoid Antioxidant activity
title_short	Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)
title_full	Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)
title_fullStr	Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)
title_full_unstemmed	Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)
title_sort	Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)
dc.creator.fl_str_mv	Gómez López, Karen Daniela
dc.contributor.advisor.none.fl_str_mv	Gil Gonzalez, Jesús Humberto Durango Restrepo, Diego Luis
dc.contributor.author.none.fl_str_mv	Gómez López, Karen Daniela
dc.contributor.researchgroup.spa.fl_str_mv	Química de Productos Naturales y de los Alimentos
dc.subject.ddc.spa.fl_str_mv	540 - Química y ciencias afines
topic	540 - Química y ciencias afines Isoflavonoide Elicitor Actividad antioxidante Isoflavonoid Antioxidant activity
dc.subject.proposal.spa.fl_str_mv	Isoflavonoide Elicitor Actividad antioxidante
dc.subject.proposal.eng.fl_str_mv	Isoflavonoid Antioxidant activity
description	ilustraciones, diagramas, tablas
publishDate	2021
dc.date.issued.none.fl_str_mv	2021-12
dc.date.accessioned.none.fl_str_mv	2022-03-24T20:06:46Z
dc.date.available.none.fl_str_mv	2022-03-24T20:06:46Z
dc.type.spa.fl_str_mv	Trabajo de grado - Maestría
dc.type.driver.spa.fl_str_mv	info:eu-repo/semantics/masterThesis
dc.type.version.spa.fl_str_mv	info:eu-repo/semantics/acceptedVersion
dc.type.content.spa.fl_str_mv	Other
dc.type.redcol.spa.fl_str_mv	http://purl.org/redcol/resource_type/TM
status_str	acceptedVersion
dc.identifier.uri.none.fl_str_mv	https://repositorio.unal.edu.co/handle/unal/81377
dc.identifier.instname.spa.fl_str_mv	Universidad Nacional de Colombia
dc.identifier.reponame.spa.fl_str_mv	Repositorio Institucional Universidad Nacional de Colombia
dc.identifier.repourl.spa.fl_str_mv	https://repositorio.unal.edu.co/
url	https://repositorio.unal.edu.co/handle/unal/81377 https://repositorio.unal.edu.co/
identifier_str_mv	Universidad Nacional de Colombia Repositorio Institucional Universidad Nacional de Colombia
dc.language.iso.spa.fl_str_mv	spa
language	spa
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Detection of the phytotoxin coronatine by ELISA and localization in infected plant tissue. Physiological and Molecular Plant Pathology, 58(6). pp 247-258. Zheng, X., Spivey, N., Zeng, W., Liu, P., Fu, Z., Klessig, D., He, SY & Dong, X. (2012). Coronatine promotes Pseudomonas syringae virulence in plants by activating a signaling cascade that inhibits salicylic acid accumulation. Cell Host & Microbe, 11(6), pp 587-596. Zimmermann, S., Nürnberger, T., Frachisse, J., Wirtz, W & Guern, J (1997). Receptor-mediated activation of a plant Ca2+-permeable ion channel involved in pathogen defense. Proceedings of the National Academy of Sciences, 94(6). pp 2751-2755.
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dc.publisher.spa.fl_str_mv	Universidad Nacional de Colombia
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spelling	Reconocimiento 4.0 Internacionalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Gil Gonzalez, Jesús Humbertof55194c9c7c861744d9c6d413d221f72600Durango Restrepo, Diego Luis1b4cbd36eb2a707cfb816d7c27dfe8e7600Gómez López, Karen Daniela42f76975c33f322336e90ce5f7f64a77Química de Productos Naturales y de los Alimentos2022-03-24T20:06:46Z2022-03-24T20:06:46Z2021-12https://repositorio.unal.edu.co/handle/unal/81377Universidad Nacional de ColombiaRepositorio Institucional Universidad Nacional de Colombiahttps://repositorio.unal.edu.co/ilustraciones, diagramas, tablasIn this work, the production and accumulation of isoflavonoids present in soybeans (Glycine max L.) is synthesized by evaluating the application of derivatives obtained from 1-oxo-indane-4- carboxylic acid and 6-bromo-1-oxo-indane-4-carboxylic acid with permutation at the carboxylic position (amino acid coupling, esterification and nucleophilic substitution), reduction of the 1-oxo group and Suzuki-Miyaura coupling at position 6. Methodologically, the work included the identification and characterization of isoflavonoids and synthetic derivatives by different chromatographic techniques (TLC, CC and HPLC) and the confirmation of their structures by some spectroscopic and spectrometric methods (1H and 13C NMR 1D 2D, UV, LC-MS, IR). Additionally, a liquid chromatography method was developed to detect and quantify these metabolites. Once the analysis methods were established, the accumulation of isoflavonoids was evaluated in soybean seedlings in response to the synthesized derivatives. The analyzes carried out involved the determination of isoflavonoids in different plant tissues (cotyledons and stem/root), in the course of time, dose-response effect due to the application of MeJA, exogenous application of synthetic derivatives and finally the evaluation of the antioxidant activity. The results revealed that the accumulation of isoflavonoids for the proposed conditions presents different distribution depending on the growth phase (VC), plant tissue, incubation time (maximum accumulation at 24 h), elicitor dose (0.16 mM) and type of elicitor (1-oxo-indanoyl-isoleucine methyl ester induced the highest contents). Finally, it was possible to find antioxidant activity in the extracts evaluated. These results provide valuable information on the improvement processes in obtaining secondary metabolites with biological activity from soybeans.En el presente trabajo se sintetiza la producción y acumulación de isoflavonoides presentes en soya (Glycine max L.) evaluando la aplicación de derivados obtenidos de los ácido 1-oxo-indano-4-carboxílico y ácido 6-bromo-1-oxo-indano-4-carboxílico con permutación en la posición carboxílica (acoplamiento de aminoácidos, esterificación y sustitución nucleofílica), reducción del grupo 1-oxo y acoplamientos tipo Suzuki-Miyaura en la posición 6. Metodológicamente, el trabajo abarcó la identificación y caracterización de isoflavonoides y derivados sintéticos por diferentes técnicas cromatográficas (CCF, CC y CLAE) y la confirmación de sus estructuras por algunos métodos espectroscópicos y espectrométricos (1H y 13C RMN 1D 2D, UV, LC-MS, IR). Adicionalmente, se desarrolló un método por cromatografía líquida para detectar y cuantificar dichos metabolitos. Establecidos los métodos de análisis, la acumulación de los isoflavonoides fue evaluada en plántulas se soya como respuesta a los derivados sintetizado. Los análisis ejecutados involucraron la determinación de isoflavonoides en diferentes tejidos de la planta (cotiledones y tallo/raíz), en el curso del tiempo, efecto dosis-respuesta por la aplicación de MeJA, aplicación exógena derivados sintéticos y finalmente la evaluación de la actividad antioxidante. Los resultados revelaron que la acumulación de isoflavonoides para las condiciones planteadas presenta distribución diferente dependiendo de la fase de crecimiento (VC), tejido de la planta, tiempo de incubación (máxima acumulación a las 24 h), dosis de elicitor (0.16 mM) y tipo de elicitor (1-oxo-indanoil-isoleucina metil éster indujo los mayores contenidos). Por último fue posible encontrar actividad antioxidante en los extractos evaluados. Estos resultados aportan información valiosa sobre los procesos de mejora en la obtención de metabolitos secundarios con actividad biológica a partir de soya. (Texto tomado de la fuente)MaestríaMagíster en Ciencias - QuímicaQuímica de Productos NaturalesÁrea Curricular en Ciencias Naturalesxx, 106 páginasapplication/pdfspaUniversidad Nacional de ColombiaMedellín - Ciencias - Maestría en Ciencias - QuímicaEscuela de químicaFacultad de CienciasMedellín, ColombiaUniversidad Nacional de Colombia - Sede Medellín540 - Química y ciencias afinesIsoflavonoideElicitorActividad antioxidanteIsoflavonoidAntioxidant activitySíntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)Synthesis of 1-oxo-indane-4-carboxylic acid derivatives and evaluation of their elicitor effect on bioactive isoflavonoids in soybean (Glycine max L)Trabajo de grado - Maestríainfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/acceptedVersionOtherhttp://purl.org/redcol/resource_type/TMAkula, R & Ravisha, G. (2011). 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Proceedings of the National Academy of Sciences, 94(6). pp 2751-2755.InvestigadoresORIGINAL1117535160.2021.pdf1117535160.2021.pdfTesis de Maestría en Ciencias - Químicaapplication/pdf3012753https://repositorio.unal.edu.co/bitstream/unal/81377/5/1117535160.2021.pdf24ec5e901bf80e8a4106186dcc309635MD55LICENSElicense.txtlicense.txttext/plain; charset=utf-84074https://repositorio.unal.edu.co/bitstream/unal/81377/6/license.txt8153f7789df02f0a4c9e079953658ab2MD56THUMBNAIL1117535160.2021.pdf.jpg1117535160.2021.pdf.jpgGenerated Thumbnailimage/jpeg4845https://repositorio.unal.edu.co/bitstream/unal/81377/7/1117535160.2021.pdf.jpg917fafb3c2d31fe2919a7645d2abfa14MD57unal/81377oai:repositorio.unal.edu.co:unal/813772024-08-05 23:10:15.729Repositorio Institucional Universidad Nacional de Colombiarepositorio_nal@unal.edu.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

Síntesis de derivados del ácido 1-oxo-indano-4-carboxílico y evaluación de su efecto elicitor de isoflavonoides bioactivos en soya (Glycine max L)

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