Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis

Detalhes bibliográficos
Ano de defesa: 2014
Autor(a) principal: Niculau, Edenilson dos Santos
Orientador(a): Silva, Maria Fátima das Graças Fernandes da lattes
Banca de defesa: Não Informado pela instituição
Tipo de documento: Tese
Tipo de acesso: Acesso embargado
Idioma: por
Instituição de defesa: Universidade Federal de São Carlos
Programa de Pós-Graduação: Programa de Pós-Graduação em Química - PPGQ
Departamento: Não Informado pela instituição
País: BR
Palavras-chave em Português:
Área do conhecimento CNPq:
Link de acesso: https://repositorio.ufscar.br/handle/20.500.14289/6329
Resumo: Citrus canker, caused by the bacteria Xanthomonas axonopodis pv. citri (Xac), is a disease that causes serious problems to the global citrus industry, especially to orange(Citrus sinensis). In this regard, this thesis describes the development of new methodologies for the diagnosis of citrus canker by volatile biomarkers or macromolecules produced by the C. sinensis-Xac association, as well, performed the chemical study of the wild strain of bacteria Xac searching to isolate and/or identify chemical compounds that may be associated to pathogenicity. The methods for diagnosis of citrus canker involved: dynamic headspace-GC-MS, HS-SPME/GC-MS and MALDI-TOF/MS. The main volatile biomarker identified by dynamic headspace-GC-MS was isoamyl benzoate and by HS-SPME/GC-MS aromatic compounds (benzaldehyde, phenyl methanol, methyl benzoate, 2-phenyl ethanol, benzyl acetate and ethyl benzoate) when N2 was used in the sample preparation, while without N2, benzothiazole and 2-ethylhexyl benzoate were the main biomarkers. The MALDI-TOF/MS technique was effective to differentiate statistically macromolecules produced by the healthy leaves of C. sinensis when in comparation to symptomatic leaves of citrus canker. The chemical study of Xac allowed the isolation or identification of 15 substances, some of them acting as signaling molecules in other bacteria with genomic similarity. Among the substances are: cyclo (Pro-Leu), cyclo (Pro-Val) and two diastereoisomers of cyclo (Pro-Phe), for which the relative configurations were determined, cyclo (Phe-Phe), quinolin-4-carboxaldehyde, fatty acid amides (octadecanamide, cis-9-octadecenamide, cis-13-docosenamide) and cis-11-methyl-2-dodecenoic acid (signaling molecule in X. campestris pv. campestris). According to several studies in literature, some of these compounds are involved in cell communication of some microorganisms or can be phytoxins released by the bacteria into the plant.
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spelling Niculau, Edenilson dos SantosSilva, Maria Fátima das Graças Fernandes dahttp://lattes.cnpq.br/0457632122660653http://lattes.cnpq.br/60722574381653854283b760-dac4-475d-b43a-3bb0ec3c655a2016-06-02T20:34:59Z2015-01-282016-06-02T20:34:59Z2014-12-17NICULAU, Edenilson dos Santos. Chemical study of Xanthomonas axonopodis pv. citri and its influence on the chemical profile in Citrus sinensis. 2014. 1 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014.https://repositorio.ufscar.br/handle/20.500.14289/6329Citrus canker, caused by the bacteria Xanthomonas axonopodis pv. citri (Xac), is a disease that causes serious problems to the global citrus industry, especially to orange(Citrus sinensis). In this regard, this thesis describes the development of new methodologies for the diagnosis of citrus canker by volatile biomarkers or macromolecules produced by the C. sinensis-Xac association, as well, performed the chemical study of the wild strain of bacteria Xac searching to isolate and/or identify chemical compounds that may be associated to pathogenicity. The methods for diagnosis of citrus canker involved: dynamic headspace-GC-MS, HS-SPME/GC-MS and MALDI-TOF/MS. The main volatile biomarker identified by dynamic headspace-GC-MS was isoamyl benzoate and by HS-SPME/GC-MS aromatic compounds (benzaldehyde, phenyl methanol, methyl benzoate, 2-phenyl ethanol, benzyl acetate and ethyl benzoate) when N2 was used in the sample preparation, while without N2, benzothiazole and 2-ethylhexyl benzoate were the main biomarkers. The MALDI-TOF/MS technique was effective to differentiate statistically macromolecules produced by the healthy leaves of C. sinensis when in comparation to symptomatic leaves of citrus canker. The chemical study of Xac allowed the isolation or identification of 15 substances, some of them acting as signaling molecules in other bacteria with genomic similarity. Among the substances are: cyclo (Pro-Leu), cyclo (Pro-Val) and two diastereoisomers of cyclo (Pro-Phe), for which the relative configurations were determined, cyclo (Phe-Phe), quinolin-4-carboxaldehyde, fatty acid amides (octadecanamide, cis-9-octadecenamide, cis-13-docosenamide) and cis-11-methyl-2-dodecenoic acid (signaling molecule in X. campestris pv. campestris). According to several studies in literature, some of these compounds are involved in cell communication of some microorganisms or can be phytoxins released by the bacteria into the plant.O cancro cítrico, causado pela bactéria Xanthomonas axonopodis pv. citri (Xac), é uma doença que provoca sérios problemas à citricultura mundial, principalmente à cultura da laranjeira, Citrus sinensis. Neste sentido, esta tese descreveu o desenvolvimento de novas metodologias para a diagnose do cancro cítrico por meio de biomarcadores voláteis ou macromoléculas produzidas por associação C. sinensis-Xac, bem como, realizou o estudo químico da linhagem selvagem da bactéria Xac buscando isolar e/ou identificar compostos químicos que de algum modo podem estar associados ao mecanismo de patogenicidade. As metodologias para diagnóstico do cancro cítrico envolveram: headspace dinâmico-GC-MS, HS-SPME/GC-MS e MALDI-TOF/MS. O principal biomarcador volátil identificado por headspace dinâmico-GC-MS foi o benzoato de isoamila e por HS-SPME/GC-MS foram identificados uma série de compostos aromáticos (benzaldeído, fenilmetanol, benzoato de metila, 2-feniletanol, acetato de benzila e benzoato de etila), quando utilizado N2 no preparo de amostra, enquanto que sem N2, benzotiazol e benzoato de 2-etilexila foram os principais biomarcadores identificados. A técnica MALDI-TOF/MS foi eficiente para diferenciar estatisticamente macromoléculas produzidas por folhas de C. sinensis sadias de folhas sintomáticas com cancro cítrico tanto de plantas em que o processo de infecção ocorreu artificialmente quanto naturalmente. O estudo químico de Xac levou ao isolamento e/ou identificação de 15 substâncias, algumas delas sinalizadoras em outras bactérias com similaridade genômica. Entre estas substâncias destacam-se: ciclo (Pro-Leu), ciclo (Pro-Val), dois diastereoisômeros de ciclo (Pro-Phe), às quais as configurações relativas foram determinadas, ciclo (Phe-Phe), quinolina-4-carboxaldeído, amidas de ácidos graxos (octadecanamida, cis-9-octadecenamida, cis-13-docosenamida) e o ácido 11-metil-cis-2-dodecenóico (sinalizador em X. campestris pv. campestris). De acordo com vários estudos existentes na literatura, alguns desses compostos são envolvidos na comunicação celular de diferentes micro-organismos ou podem ser fitotoxinas lançadas pela bactéria na planta.Universidade Federal de Minas Geraisapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRQuímica orgânicaCancro cítricoEstudo químico in vitro e in vivoBiomarcadores voláteisMacromoléculasCIENCIAS EXATAS E DA TERRA::QUIMICAEstudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensisChemical study of Xanthomonas axonopodis pv. citri and its influence on the chemical profile in Citrus sinensisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesis-1-124b0ac94-885a-4e7b-b93a-7cad21b9592einfo:eu-repo/semantics/embargoedAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALTeseESN.pdfTeseESN.pdfapplication/pdf8202376https://repositorio.ufscar.br/bitstreams/6c152a79-b4b9-40f4-a510-160c7da65178/download7b49647f65fd758f827a304f33c3dcabMD51trueAnonymousREADTEXTTeseESN.pdf.txtTeseESN.pdf.txtExtracted texttext/plain325625https://repositorio.ufscar.br/bitstreams/5fc7d4c4-ece9-42cf-9da7-1aa99b5c9e7b/download2b344c2961a6df26113c756655563e9fMD54falseAnonymousREADTHUMBNAILTeseESN.pdf.jpgTeseESN.pdf.jpgIM Thumbnailimage/jpeg7200https://repositorio.ufscar.br/bitstreams/e14d9b26-f3b5-4b06-af3f-23b59c79e3b4/download9225dee27b5d4d30724e41751f3f3bc1MD55falseAnonymousREAD20.500.14289/63292025-02-05 15:33:48.075open.accessoai:repositorio.ufscar.br:20.500.14289/6329https://repositorio.ufscar.brRepositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestrepositorio.sibi@ufscar.bropendoar:43222025-02-05T18:33:48Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false
dc.title.por.fl_str_mv Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis
dc.title.alternative.eng.fl_str_mv Chemical study of Xanthomonas axonopodis pv. citri and its influence on the chemical profile in Citrus sinensis
title Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis
spellingShingle Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis
Niculau, Edenilson dos Santos
Química orgânica
Cancro cítrico
Estudo químico in vitro e in vivo
Biomarcadores voláteis
Macromoléculas
CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis
title_full Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis
title_fullStr Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis
title_full_unstemmed Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis
title_sort Estudo químico de Xanthomonas citri subsp. citri e sua influência no perfil químico de Citrus sinensis
author Niculau, Edenilson dos Santos
author_facet Niculau, Edenilson dos Santos
author_role author
dc.contributor.authorlattes.por.fl_str_mv http://lattes.cnpq.br/6072257438165385
dc.contributor.author.fl_str_mv Niculau, Edenilson dos Santos
dc.contributor.advisor1.fl_str_mv Silva, Maria Fátima das Graças Fernandes da
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/0457632122660653
dc.contributor.authorID.fl_str_mv 4283b760-dac4-475d-b43a-3bb0ec3c655a
contributor_str_mv Silva, Maria Fátima das Graças Fernandes da
dc.subject.por.fl_str_mv Química orgânica
Cancro cítrico
Estudo químico in vitro e in vivo
Biomarcadores voláteis
Macromoléculas
topic Química orgânica
Cancro cítrico
Estudo químico in vitro e in vivo
Biomarcadores voláteis
Macromoléculas
CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.cnpq.fl_str_mv CIENCIAS EXATAS E DA TERRA::QUIMICA
description Citrus canker, caused by the bacteria Xanthomonas axonopodis pv. citri (Xac), is a disease that causes serious problems to the global citrus industry, especially to orange(Citrus sinensis). In this regard, this thesis describes the development of new methodologies for the diagnosis of citrus canker by volatile biomarkers or macromolecules produced by the C. sinensis-Xac association, as well, performed the chemical study of the wild strain of bacteria Xac searching to isolate and/or identify chemical compounds that may be associated to pathogenicity. The methods for diagnosis of citrus canker involved: dynamic headspace-GC-MS, HS-SPME/GC-MS and MALDI-TOF/MS. The main volatile biomarker identified by dynamic headspace-GC-MS was isoamyl benzoate and by HS-SPME/GC-MS aromatic compounds (benzaldehyde, phenyl methanol, methyl benzoate, 2-phenyl ethanol, benzyl acetate and ethyl benzoate) when N2 was used in the sample preparation, while without N2, benzothiazole and 2-ethylhexyl benzoate were the main biomarkers. The MALDI-TOF/MS technique was effective to differentiate statistically macromolecules produced by the healthy leaves of C. sinensis when in comparation to symptomatic leaves of citrus canker. The chemical study of Xac allowed the isolation or identification of 15 substances, some of them acting as signaling molecules in other bacteria with genomic similarity. Among the substances are: cyclo (Pro-Leu), cyclo (Pro-Val) and two diastereoisomers of cyclo (Pro-Phe), for which the relative configurations were determined, cyclo (Phe-Phe), quinolin-4-carboxaldehyde, fatty acid amides (octadecanamide, cis-9-octadecenamide, cis-13-docosenamide) and cis-11-methyl-2-dodecenoic acid (signaling molecule in X. campestris pv. campestris). According to several studies in literature, some of these compounds are involved in cell communication of some microorganisms or can be phytoxins released by the bacteria into the plant.
publishDate 2014
dc.date.issued.fl_str_mv 2014-12-17
dc.date.available.fl_str_mv 2015-01-28
2016-06-02T20:34:59Z
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dc.identifier.citation.fl_str_mv NICULAU, Edenilson dos Santos. Chemical study of Xanthomonas axonopodis pv. citri and its influence on the chemical profile in Citrus sinensis. 2014. 1 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014.
dc.identifier.uri.fl_str_mv https://repositorio.ufscar.br/handle/20.500.14289/6329
identifier_str_mv NICULAU, Edenilson dos Santos. Chemical study of Xanthomonas axonopodis pv. citri and its influence on the chemical profile in Citrus sinensis. 2014. 1 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014.
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