Recent Advances in Molecular Genetics of Furanocoumarin Synthesis in Higher Plants

Bourgaud, Frédéric; Olry, Alexandre; Hehn, Alain

doi:10.1007/978-94-017-8953-0_14

Cited by 13 publications

(16 citation statements)

References 42 publications

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“…Intriguingly, no CYP71AZ could be identified in other plants producing FCs such as Rutaceae (citrus for example) or Moraceae (Ficus for example). Although we could not test all the plants belonging to these plant species because of the absence of available databases, it might be possible that the synthesis of these molecules in other plants is realized by other genes and is in favor of a convergent evolution as suggested previously ( Berenbaum, 1983 ; Bourgaud et al, 2014 , Munakata et al, 2016 ).…”

Section: Discussionmentioning

confidence: 99%

“…They have been detected in only a few plant families, and these families are not phylogenetically related. Linear (psoralens) and angular FCs may have arisen by convergent evolution ( Bourgaud et al, 2014 ) and are distinguished by the position of the furan-ring on the coumarin core molecule ( Figure 1 ). Plants first acquired the ability to produce linear isomers, and the formation of the angular analogs evolved later ( Berenbaum, 2002 ).…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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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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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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“…It would be interesting now to investigate the substrate specificity of other Apiaceae and Rutaceae orthologous dioxygenases to check if this reflects a general rule or not. This study might also be extended to other furanocoumarin producer plants such as Moraceae and Fabaceae (Bourgaud et al ., ).…”

Section: Discussionmentioning

confidence: 99%

“…Two structural isomers of furanocoumarins were described based on the position of the furan ring on the coumarin core molecule, leading to either linear or angular isomers (Ellis and Brown, ) (Figure ). While linear forms have been reported in all plants that synthesize furanocoumarins, angular forms have only been detected in Fabaceae, Apiaceae and Moraceae (Bourgaud et al ., ). The appearance of angular furanocoumarins has been described as an arms race between plants and herbivores (Berenbaum and Feeny, ; Berenbaum, ).…”

Section: Introductionmentioning

confidence: 99%

A bacterial artificial chromosome (BAC) genomic approach reveals partial clustering of the furanocoumarin pathway genes in parsnip

et al. 2017

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Furanocoumarins are specialized metabolites that are involved in the defense of plants against phytophagous insects. The molecular and functional characterization of the genes involved in their biosynthetic pathway is only partially complete. Many recent reports have described gene clusters responsible for the biosynthesis of specialized metabolites in plants. To investigate possible co-localization of the genes involved in the furanocoumarin pathway, we sequenced parsnip BAC clones spanning two different gene loci. We found that two genes previously identified in this pathway, CYP71AJ3 and CYP71AJ4, were located on the same BAC, whereas a third gene, PsPT1, belonged to a different BAC clone. Chromosome mapping using fluorescence in situ hybridization (FISH) indicated that PsPT1 and the CYP71AJ3-CYP71AJ4 clusters are located on two different chromosomes. Sequencing the BAC clone harboring PsPT1 led to the identification of a gene encoding an Fe(II) α-ketoglutarate-dependent dioxygenase (PsDIOX) situated in the neighborhood of PsPT1 and confirmed the occurrence of a second gene cluster involved in the furanocoumarin pathway. This enzyme metabolizes p-coumaroyl CoA, leading exclusively to the synthesis of umbelliferone, an important intermediate compound in furanocoumarin synthesis. This work provides an insight into the genomic organization of genes from the furanocoumarin biosynthesis pathway organized in more than one gene cluster. It also confirms that the screening of a genomic library and the sequencing of BAC clones represent a valuable tool to identify genes involved in biosynthetic pathways dedicated to specialized metabolite synthesis.

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“…FCs have been classified into two distinct subgroups, linear and angular, based on the positions of the furan ring associated with the coumarin core structure (Seiger, ; Bourgaud et al ., , ). These molecules contribute to plant chemical defences, mainly against biotic stresses, such as herbivores and pathogens (Bourgaud et al ., ), and are also a key element in the arms race between Apiaceae and Lepidopteran insects (Berenbaum & Feeny, ). FCs show a scattered distribution in angiosperms, with a chemotaxonomical tendency towards four distant plant families: Apiaceae, Fabaceae, Moraceae and Rutaceae (Supporting Information Fig.…”

Section: Introductionmentioning

confidence: 99%

Convergent evolution of the UbiA prenyltransferase family underlies the independent acquisition of furanocoumarins in plants

et al. 2019

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Furanocoumarins (FCs) are plant-specialized metabolites with potent allelochemical properties. The distribution of FCs is scattered with a chemotaxonomical tendency towards four distant families with highly similar FC pathways. The mechanism by which this pathway emerged and spread in plants has not been elucidated. Furanocoumarin biosynthesis was investigated in Ficus carica (fig, Moraceae), focusing on the first committed reaction catalysed by an umbelliferone dimethylallyltransferase (UDT). Comparative RNA-seq analysis among latexes of different fig organs led to the identification of a UDT. The phylogenetic relationship of this UDT to previously reported Apiaceae UDTs was evaluated.The expression pattern of F. carica prenyltransferase 1 (FcPT1) was related to the FC contents in different latexes. Enzymatic characterization demonstrated that one of the main functions of FcPT1 is UDT activity. Phylogenetic analysis suggested that FcPT1 and Apiaceae UDTs are derived from distinct ancestors, although they both belong to the UbiA superfamily. These findings are supported by significant differences in the related gene structures.This report describes the identification of FcPT1 involved in FC biosynthesis in fig and provides new insights into multiple origins of the FC pathway and, more broadly, into the adaptation of plants to their environments.

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Recent Advances in Molecular Genetics of Furanocoumarin Synthesis in Higher Plants

Cited by 13 publications

References 42 publications

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

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

A bacterial artificial chromosome (BAC) genomic approach reveals partial clustering of the furanocoumarin pathway genes in parsnip

Convergent evolution of the UbiA prenyltransferase family underlies the independent acquisition of furanocoumarins in plants

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