CYP712K4 Catalyzes the C-29 Oxidation of Friedelin in the Maytenus ilicifolia Quinone Methide Triterpenoid Biosynthesis Pathway
| Autor: | Jacob Pollier, Alain Goossens, Philipp Arendt, Cleslei Fernando Zanelli, Keylla U Bicalho, Mariana Marchi Santoni, Maysa Furlan |
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| Přispěvatelé: | Ghent University, VIB Center for Plant Systems Biology, Universidade Estadual Paulista (Unesp), VIB Metabolomics Core |
| Rok vydání: | 2019 |
| Předmět: |
0106 biological sciences
0301 basic medicine Magnetic Resonance Spectroscopy Physiology PROTEIN Nicotiana benthamiana Plant Science 01 natural sciences Mass Spectrometry chemistry.chemical_compound CYP712K4 Maytenoic acid ATP synthase biology food and beverages General Medicine Celastrol VECTORS TRANSIENT EXPRESSION Pentacyclic Triterpenes Oxidation-Reduction Stereochemistry Saccharomyces cerevisiae Friedelin 03 medical and health sciences Tobacco PLANTS YEAST Indolequinones fungi Biology and Life Sciences PLATFORM Cytochrome P450 Cell Biology Maytenus biology.organism_classification Quinone methide Yeast Triterpenes Plant Leaves 030104 developmental biology chemistry Quinone methide triterpenoids biology.protein Maytenus ilicifolia SYSTEM 010606 plant biology & botany |
| Zdroj: | PLANT AND CELL PHYSIOLOGY Scopus Repositório Institucional da UNESP Universidade Estadual Paulista (UNESP) instacron:UNESP |
| ISSN: | 1471-9053 0032-0781 |
| Popis: | Made available in DSpace on 2020-12-12T01:45:00Z (GMT). No. of bitstreams: 0 Previous issue date: 2019-11-01 The 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. Department of Plant Biotechnology and Bioinformatics Ghent University VIB Center for Plant Systems Biology Department of Organic Chemistry Institute of Chemistry so Paulo State University (UNESP) Department of Biological Sciences School of Pharmaceutical Sciences so Paulo State University (UNESP) VIB Metabolomics Core Department of Organic Chemistry Institute of Chemistry so Paulo State University (UNESP) Department of Biological Sciences School of Pharmaceutical Sciences so Paulo State University (UNESP) |
| Databáze: | OpenAIRE |
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