CYP712K4 Catalyzes the C-29 Oxidation of Friedelin in the Maytenus ilicifolia Quinone Methide Triterpenoid Biosynthesis Pathway

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Autor(es): dc.contributorGhent University-
Autor(es): dc.contributorVIB Center for Plant Systems Biology-
Autor(es): dc.contributorUniversidade Estadual Paulista (Unesp)-
Autor(es): dc.contributorVIB Metabolomics Core-
Autor(es): dc.creatorBicalho, Keylla U [UNESP]-
Autor(es): dc.creatorSantoni, Mariana M [UNESP]-
Autor(es): dc.creatorArendt, Philipp-
Autor(es): dc.creatorZanelli, Cleslei F [UNESP]-
Autor(es): dc.creatorFurlan, Maysa [UNESP]-
Autor(es): dc.creatorGoossens, Alain-
Autor(es): dc.creatorPollier, Jacob-
Data de aceite: dc.date.accessioned2022-02-22T00:27:53Z-
Data de disponibilização: dc.date.available2022-02-22T00:27:53Z-
Data de envio: dc.date.issued2020-12-11-
Data de envio: dc.date.issued2020-12-11-
Data de envio: dc.date.issued2019-10-31-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1093/pcp/pcz144-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/199628-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/199628-
Descrição: dc.descriptionThe native Brazilian plant Maytenus ilicifolia accumulates a set of quinone methide triterpenoids with important pharmacological properties, of which maytenin, pristimerin and celastrol accumulate exclusively in the root bark of this medicinal plant. The first committed step in the quinone methide triterpenoid biosynthesis is the cyclization of 2,3-oxidosqualene to friedelin, catalyzed by the oxidosqualene cyclase friedelin synthase (FRS). In this study, we produced heterologous friedelin by the expression of M. ilicifolia FRS in Nicotiana benthamiana leaves and in a Saccharomyces cerevisiae strain engineered using CRISPR/Cas9. Furthermore, friedelin-producing N. benthamiana leaves and S. cerevisiae cells were used for the characterization of CYP712K4, a cytochrome P450 from M. ilicifolia that catalyzes the oxidation of friedelin at the C-29 position, leading to maytenoic acid, an intermediate of the quinone methide triterpenoid biosynthesis pathway. Maytenoic acid produced in N. benthamiana leaves was purified and its structure was confirmed using high-resolution mass spectrometry and nuclear magnetic resonance analysis. The three-step oxidation of friedelin to maytenoic acid by CYP712K4 can be considered as the second step of the quinone methide triterpenoid biosynthesis pathway, and may form the basis for further discovery of the pathway and heterologous production of friedelanes and ultimately quinone methide triterpenoids.-
Descrição: dc.descriptionDepartment of Plant Biotechnology and Bioinformatics Ghent University-
Descrição: dc.descriptionVIB Center for Plant Systems Biology-
Descrição: dc.descriptionDepartment of Organic Chemistry Institute of Chemistry so Paulo State University (UNESP)-
Descrição: dc.descriptionDepartment of Biological Sciences School of Pharmaceutical Sciences so Paulo State University (UNESP)-
Descrição: dc.descriptionVIB Metabolomics Core-
Descrição: dc.descriptionDepartment of Organic Chemistry Institute of Chemistry so Paulo State University (UNESP)-
Descrição: dc.descriptionDepartment of Biological Sciences School of Pharmaceutical Sciences so Paulo State University (UNESP)-
Formato: dc.format2510-2522-
Idioma: dc.languageen-
Relação: dc.relationPlant and Cell Physiology-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectCelastrol-
Palavras-chave: dc.subjectCYP712K4-
Palavras-chave: dc.subjectFriedelin-
Palavras-chave: dc.subjectMaytenoic acid-
Palavras-chave: dc.subjectMaytenus ilicifolia-
Palavras-chave: dc.subjectQuinone methide triterpenoids-
Título: dc.titleCYP712K4 Catalyzes the C-29 Oxidation of Friedelin in the Maytenus ilicifolia Quinone Methide Triterpenoid Biosynthesis Pathway-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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