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The CYP71AZ P450 Subfamily: A Driving Factor for the Diversification of Coumarin Biosynthesis in Apiaceous Plants

The production of coumarins and furanocoumarins (FCs) in higher plants is widely considered a model illustration of the adaptation of plants to their environment. In this report, we show that the multiplication of cytochrome P450 variants within the CYP71AZ subfamily has contributed to the diversifi...

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Autores principales: Krieger, Célia, Roselli, Sandro, Kellner-Thielmann, Sandra, Galati, Gianni, Schneider, Bernd, Grosjean, Jérémy, Olry, Alexandre, Ritchie, David, Matern, Ulrich, Bourgaud, Frédéric, Hehn, Alain
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6018538/
https://www.ncbi.nlm.nih.gov/pubmed/29971079
http://dx.doi.org/10.3389/fpls.2018.00820
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author Krieger, Célia
Roselli, Sandro
Kellner-Thielmann, Sandra
Galati, Gianni
Schneider, Bernd
Grosjean, Jérémy
Olry, Alexandre
Ritchie, David
Matern, Ulrich
Bourgaud, Frédéric
Hehn, Alain
author_facet Krieger, Célia
Roselli, Sandro
Kellner-Thielmann, Sandra
Galati, Gianni
Schneider, Bernd
Grosjean, Jérémy
Olry, Alexandre
Ritchie, David
Matern, Ulrich
Bourgaud, Frédéric
Hehn, Alain
author_sort Krieger, Célia
collection PubMed
description The production of coumarins and furanocoumarins (FCs) in higher plants is widely considered a model illustration of the adaptation of plants to their environment. In this report, we show that the multiplication of cytochrome P450 variants within the CYP71AZ subfamily has contributed to the diversification of these molecules. Multiple copies of genes encoding this enzyme family are found in Apiaceae, and their phylogenetic analysis suggests that they have different functions within these plants. CYP71AZ1 from Ammi majus and CYP71AZ3, 4, and 6 from Pastinaca sativa were functionally characterized. While CYP71AZ3 merely hydroxylated esculetin, the other enzymes accepted both simple coumarins and FCs. Superimposing in silico models of these enzymes led to the identification of different conformations of three regions in the enzyme active site. These sequences were subsequently utilized to mutate CYP71AZ4 to resemble CYP71AZ3. The swapping of these regions lead to significantly modified substrate specificity. Simultaneous mutations of all three regions shifted the specificity of CYP71AZ4 to that of CYP71AZ3, exclusively accepting esculetin. This approach may explain the evolution of this cytochrome P450 family regarding the appearance of FCs in parsnip and possibly in the Apiaceae.
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spelling pubmed-60185382018-07-03 The CYP71AZ P450 Subfamily: A Driving Factor for the Diversification of Coumarin Biosynthesis in Apiaceous Plants Krieger, Célia Roselli, Sandro Kellner-Thielmann, Sandra Galati, Gianni Schneider, Bernd Grosjean, Jérémy Olry, Alexandre Ritchie, David Matern, Ulrich Bourgaud, Frédéric Hehn, Alain Front Plant Sci Plant Science The production of coumarins and furanocoumarins (FCs) in higher plants is widely considered a model illustration of the adaptation of plants to their environment. In this report, we show that the multiplication of cytochrome P450 variants within the CYP71AZ subfamily has contributed to the diversification of these molecules. Multiple copies of genes encoding this enzyme family are found in Apiaceae, and their phylogenetic analysis suggests that they have different functions within these plants. CYP71AZ1 from Ammi majus and CYP71AZ3, 4, and 6 from Pastinaca sativa were functionally characterized. While CYP71AZ3 merely hydroxylated esculetin, the other enzymes accepted both simple coumarins and FCs. Superimposing in silico models of these enzymes led to the identification of different conformations of three regions in the enzyme active site. These sequences were subsequently utilized to mutate CYP71AZ4 to resemble CYP71AZ3. The swapping of these regions lead to significantly modified substrate specificity. Simultaneous mutations of all three regions shifted the specificity of CYP71AZ4 to that of CYP71AZ3, exclusively accepting esculetin. This approach may explain the evolution of this cytochrome P450 family regarding the appearance of FCs in parsnip and possibly in the Apiaceae. Frontiers Media S.A. 2018-06-19 /pmc/articles/PMC6018538/ /pubmed/29971079 http://dx.doi.org/10.3389/fpls.2018.00820 Text en Copyright © 2018 Krieger, Roselli, Kellner-Thielmann, Galati, Schneider, Grosjean, Olry, Ritchie, Matern, Bourgaud and Hehn. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Plant Science
Krieger, Célia
Roselli, Sandro
Kellner-Thielmann, Sandra
Galati, Gianni
Schneider, Bernd
Grosjean, Jérémy
Olry, Alexandre
Ritchie, David
Matern, Ulrich
Bourgaud, Frédéric
Hehn, Alain
The CYP71AZ P450 Subfamily: A Driving Factor for the Diversification of Coumarin Biosynthesis in Apiaceous Plants
title The CYP71AZ P450 Subfamily: A Driving Factor for the Diversification of Coumarin Biosynthesis in Apiaceous Plants
title_full The CYP71AZ P450 Subfamily: A Driving Factor for the Diversification of Coumarin Biosynthesis in Apiaceous Plants
title_fullStr The CYP71AZ P450 Subfamily: A Driving Factor for the Diversification of Coumarin Biosynthesis in Apiaceous Plants
title_full_unstemmed The CYP71AZ P450 Subfamily: A Driving Factor for the Diversification of Coumarin Biosynthesis in Apiaceous Plants
title_short The CYP71AZ P450 Subfamily: A Driving Factor for the Diversification of Coumarin Biosynthesis in Apiaceous Plants
title_sort cyp71az p450 subfamily: a driving factor for the diversification of coumarin biosynthesis in apiaceous plants
topic Plant Science
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6018538/
https://www.ncbi.nlm.nih.gov/pubmed/29971079
http://dx.doi.org/10.3389/fpls.2018.00820
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