The evolution of foliar terpene diversity in Myrtaceae

Padovan, Amanda; Keszei, András; Külheim, Carsten; Foley, William J.

doi:10.1007/s11101-013-9331-3

Cited by 66 publications

(54 citation statements)

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“…The trees are grown for industrial purposes such as the production of pulp for paper, firewood, charcoal, and essential oils. Eucalyptus plants synthesize a broad spectrum of specialized metabolites, including terpenes, phenolics, formylated phloroglucinols, and cyanogenic glucosides (Eschler et al, 2000;Gleadow et al, 2008;Padovan et al, 2014;Marsh et al, 2017). Very little is known about the biosynthesis of specialized metabolites in Eucalyptus trees.…”

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confidence: 99%

Reconfigured Cyanogenic Glucoside Biosynthesis in Eucalyptus cladocalyx Involves a Cytochrome P450 CYP706C55

et al. 2018

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Cyanogenic glucosides are a class of specialized metabolites widespread in the plant kingdom. Cyanogenic glucosides are αhydroxynitriles, and their hydrolysis releases toxic hydrogen cyanide, providing an effective chemical defense against herbivores. Eucalyptus cladocalyx is a cyanogenic tree, allocating up to 20% of leaf nitrogen to the biosynthesis of the cyanogenic monoglucoside, prunasin. Here, mass spectrometry analyses of E. cladocalyx tissues revealed spatial and ontogenetic variations in prunasin content, as well as the presence of the cyanogenic diglucoside amygdalin in flower buds and flowers. The identification and biochemical characterization of the prunasin biosynthetic enzymes revealed a unique enzyme configuration for prunasin production in E. cladocalyx. This result indicates that a multifunctional cytochrome P450 (CYP), CYP79A125, catalyzes the initial conversion of l-phenylalanine into its corresponding aldoxime, phenylacetaldoxime; a function consistent with other members of the CYP79 family. In contrast to the single multifunctional CYP known from other plant species, the conversion of phenylacetaldoxime to the α-hydroxynitrile, mandelonitrile, is catalyzed by two distinct CYPs. CYP706C55 catalyzes the dehydration of phenylacetaldoxime, an unusual CYP reaction. The resulting phenylacetonitrile is subsequently hydroxylatedby CYP71B103 to form mandelonitrile. The final glucosylation step to yield prunasin is catalyzed by a UDP-glucosyltransferase, UGT85A59. Members of the CYP706 family have not been reported previously to participate in the biosynthesis of cyanogenic glucosides, and the pathway structure in E. cladocalyx represents an example of convergent evolution in the biosynthesis of cyanogenic glucosides in plants.www.plantphysiol.org on August 1, 2020 -Published by Downloaded from Metabolite data were analyzed in SigmaPlot (version 13.0) using oneway ANOVA. Normality (Kolmogorov-Smirnov) and equal variance (Brown-Forsythe) were tested to cutoffs of P > 0.02 and P > 0.04, respectively, and when assumptions were not met, the data were transformed by natural logarithm. Pearson correlation was used to analyze gene expression. PK, Svendsen I, Møller BL (2000) Cytochromes P-450 from cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin: cloning, functional expression in Pichia pastoris, and substrate specificity of the isolated recombinant enzymes. J Biol Chem 275: 1966-1975 Bak S, Kahn RA, Nielsen HL, Møller BL, Halkier BA (1998) Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin. Plant Mol Biol 36: 393-405 Bassard JE, Møller BL, Laursen T (2017) Assembly of dynamic P450-mediated metabolons: order versus chaos. Curr Mol Biol Rep 3: 37-51 Bjarnholt N, Li B, D'Alvise J, Janfelt C (2014) Mass...

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Reconfigured Cyanogenic Glucoside Biosynthesis in Eucalyptus cladocalyx Involves a Cytochrome P450 CYP706C55

et al. 2018

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“…Given that 1) we understand the quantitative and qualitative variation of terpenes in eucalypts well [45,46], and 2) a commercial coppice system for pharmaceutical terpene production exists [47], we can estimate commercial-scale production of biofuels from have the potential to produce 686 kg of essential oil ha -1 y -1 [51].…”

Section: Plant Terpenes As a Source For Specialty Biofuelsmentioning

confidence: 99%

“…The refining steps of these terpenes include hydrotreatment and fractionation to produce biodiesel. The composition of crude oil extracted by steam-distillation from eucalypt leaves is highly variable both between and within species [45]. For example, current populations of E. polybractea contain between 8-98% 1,8-cineole (Kainer et al, unpublished results).…”

Section: Plant Terpenes As a Source For Specialty Biofuelsmentioning

confidence: 99%

“…These technologies are able to resolve structural details on length scales from ~1 nm to 100 µm [76][77][78] and have the potential to elucidate the internal structure of oil glands. [45]. Of these eucalypts, fifteen species have oil profiles dominated by α-pinene, β-pinene, or p-cymene (Table 2), and most have good abilities to re-sprout after coppicing and are able to grow in the semi-arid sub-tropic climate zones.…”

Section: A Systems-level Understanding Of Terpene Biosynthesismentioning

confidence: 99%

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Plant-Derived Terpenes: A Feedstock for Specialty Biofuels

Mewalal

Rai

Kainer

et al. 2017

Trends in Biotechnology

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148

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Research toward renewable and sustainable energy has identified specific terpenes capable of supplementing or replacing current petroleum-derived fuels. Despite being naturally produced and stored by many plants, there are few examples of commercial recovery of terpenes from plants because of low yields. Plant terpene biosynthesis is regulated at multiple levels, leading to wide variability in terpene content and chemistry. Advances in the plant molecular toolkit, including annotated genomes, high-throughput omics profiling, and genome editing, have begun to elucidate plant terpene metabolism, and such information is useful for bioengineering metabolic pathways for specific terpenes. We review here the status of terpenes as a specialty biofuel and discuss the potential of plants as a viable agronomic solution for future terpene-derived biofuels.

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“…The family is also known for the significant qualitative and quantitative variations seen between taxa, populations and individuals (Keszei et al 2008). Previously, there has been significant effort in cataloguing the chemical diversity found within the family (Boland et al 1991;Brophy et al 2013;Padovan et al 2014), but it is only recently that the genetics and biochemical process that underlie this variation have begun to be investigated.…”

Section: Introductionmentioning

confidence: 99%

The genetic basis of foliar terpene yield: Implications for breeding and profitability of Australian essential oil crops

Webb

Foley

Külheim

2015

Plant Biotechnology

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The family Myrtaceae is known for its high foliar terpene concentrations as well as significant qualitative and quantitative variation in foliar terpenes between taxa, populations and individuals. To date, few studies have investigated the genetic and biochemical processes, which underlie this variation, much of which is known to be under genetic control. Differences in yield are both ecologically and commercially important and a better understanding of its basis will allow a greater understanding of Australian ecosystems as well as improve commercial viability of essential oil industries. Over the past decade a good understanding of the genes involved in terpene biosynthesis has developed in other species and several important regulatory steps have been identified. Much of this work has been done in transgenic plants, so our understanding at a molecular level is strong. Nonetheless, it remains unclear if these processes are transferrable to wild populations, or indeed how ecologically important quantitative variation in terpenoids arise and are maintained in natural ecosystems. In this review we will summarize what is known about terpene biosynthesis and the control of flux through the terpene biosynthetic pathways. We will then argue that this platform of work provides a great resource for Myrtaceae, as well as other plants, to identify candidate genes that control flux through the biosynthetic pathways and how this will inform further studies into the ecological implications of quantitative variation of terpenes. Work into terpene biosynthesis would also provide a framework to improve the profitability of essential oil crops.

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The evolution of foliar terpene diversity in Myrtaceae

Cited by 66 publications

References 78 publications

Reconfigured Cyanogenic Glucoside Biosynthesis in Eucalyptus cladocalyx Involves a Cytochrome P450 CYP706C55

Reconfigured Cyanogenic Glucoside Biosynthesis in Eucalyptus cladocalyx Involves a Cytochrome P450 CYP706C55

Plant-Derived Terpenes: A Feedstock for Specialty Biofuels

The genetic basis of foliar terpene yield: Implications for breeding and profitability of Australian essential oil crops

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