Biosynthesis of cyanogenic glucosides in <i>Phaseolus lunatus</i> and the evolution of oxime‐based defenses

Lai, Daniela; Maimann, Alexandra Bianca; Macea, Eliana; Ocampo, C.; Cardona, Gustavo A.; Pičmanová, Martina; Darbani, Behrooz; Olsen, Carl Erik; Debouck, Daniel G.; Raatz, Bodo; Møller, Birger Lindberg; Rook, Fred

doi:10.1002/pld3.244

Cited by 24 publications

(19 citation statements)

References 56 publications

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“…In recent decades, advances in genomics, combined with biochemical and physiological studies, have provided important insights into the molecular bases of these defense metabolite pathways and their macroevolutionary origins (e.g. Zhuang et al ., 2012; Edger et al ., 2015; Xu et al ., 2017; Lai et al ., 2020). On a microevolutionary timescale, species that are polymorphic for chemical defense production have served as especially valuable systems for studying the molecular basis of adaptive variation and the roles of natural selection and other forces in maintaining it (Brachi et al ., 2015; Wager & Li, 2018; Keith & Mitchell‐Olds, 2019; Lowry et al ., 2019).…”

Section: Introductionmentioning

confidence: 99%

Dual‐species origin of an adaptive chemical defense polymorphism

et al. 2021

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Allopolyploid speciation and chemical defense diversification are two of the most characteristic features of plant evolution; although the former has likely shaped the latter, this has rarely been documented. Here we document allopolyploidy-mediated chemical defense evolution in the origin of cyanogenesis (HCN release upon tissue damage) in white clover (Trifolium repens).We combined linkage mapping of the loci that control cyanogenesis (Ac, controlling production of cyanogenic glucosides; and Li, controlling production of their hydrolyzing enzyme linamarase) with genome sequence comparisons between white clover, a recently evolved allotetraploid, and its diploid progenitors (Trifolium pallescens, Trifolium occidentale).The Ac locus (a three-gene cluster comprising the cyanogenic glucoside pathway) is derived from T. occidentale; it maps to linkage group 2O (occidentale subgenome) and is orthologous to a highly similar cluster in the T. occidentale reference genome. By contrast, Li maps to linkage group 4P (pallescens subgenome), indicating an origin in the other progenitor species.These results indicate that cyanogenesis evolved in white clover as a product of the interspecific hybridization that created the species. This allopolyploidization-derived chemical defense, together with subsequent selection on intraspecific cyanogenesis variation, appears to have contributed to white clover's ecological success as a globally distributed weed species.

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Section: Introductionmentioning

confidence: 99%

Dual‐species origin of an adaptive chemical defense polymorphism

et al. 2021

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“…Cyanogenic glycosides are derived from the amino acids phenylalanine, tyrosine, valine, leucine, and isoleucine, and from the non-protein amino acid cyclopentenylglycine (Olafsdottir et al, 1991; Gleadow and Møller, 2014). The full biosynthetic pathway for cyanogenic glucosides has been characterized in several angiosperm species including sorghum ( Sorghum bicolor; (Koch et al, 1995; Bak et al, 1998b; Jones et al, 1999), cassava ( Manihot esculenta; Andersen et al, 2000; Jørgensen et al, 2011; Kannangara et al, 2011), barley ( Hordeum vulgare; Knoch et al ., 2016), Lotus japonicus (Forslund, 2004; Takos et al, 2011), Eucalyptus cladocalyx (Hansen et al, 2018), almond ( Prunus dulcis ; Thodberg et al, 2018) and green bean ( Phaseolus vulgaris; Lai et al, 2020), and has been partially identified in conifers (Luck et al, 2017). Comparison of the biosynthetic pathways reveal that the biosynthesis has arisen independently several times in the plant kingdom (Takos et al, 2011; Hansen et al, 2018; Thodberg et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

The fern CYPome: Fern-specific cytochrome P450 family involved in convergent evolution of chemical defense

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Hansen

Takos

et al. 2021

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Plant natural products encompass an enormous chemical diversity bearing witness to great molecular innovation that occured throughout land plant evolution. Cytochrome P450 monooxygenases (CYPs) catalyze a wide variety of monooxygenation reactions essential to the metabolic repertoire of plants natural products. Ferns constitute the second largest group of vascular plants and hold a significant phylogenetic position in land evolution, lying sister to seed plants. To date, CYP diversity has not been described for this taxon and pathway discovery in ferns in general is scarce, despite possessing a rich diversity of natural products. We analysed over 8000 available fern CYPs, classifing and characterizing the landscape of this super-enzyme group. Fern CYPs are dominated by fern-specific families (∼60%), with the largest family – CYP981 – constituting approximately 15% of all predicted fern CYPs in the dataset. The abundancy and dynamics of the CYP981 family suggest a position equivalent to the CYP71 family present in seed plants, with potential roles in natural product biosynthesis. Ferns are the evolutionary oldest group to biosynthesize cyanogenic glycosides; amino acid-derived defense compounds. We show that CYP981F5 from the highly cyanogenic fern Phlebodium aureum catalyzes the conversion of phenylacetonitrile to mandelonitrile, an intermediate step in cyanogenic glycoside biosynthesis. The fern CYPome provides an important platform to further understand evolution of metabolite biosynthesis throughout the plant kingdom, and in ferns specifically.

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“…A T-DNA insertion in the CYP83B gene leads to plants with a phenotype of auxin overproduction, whereas CYP83B overexpression leads to the loss of apical dominance, typical of an auxin deficit [ 57 , 58 ]. In addition, in Phaseolus lunatus , CYP83E is involved in the biosynthesis of cyanogenic glucoside via indole aldoxime oxidation [ 59 ]. Although the biochemical function of DzCYP83F is still unknown and neither glucosinolates nor cyanogenic glucosides have been found in durian fruit, it potentially utilizes IAA as a substrate to maintain auxin homeostasis during durian fruit ripening.…”

Section: Resultsmentioning

confidence: 99%

Genome-wide identification and expression profiling of durian CYPome related to fruit ripening

et al. 2021

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Durian (Durio zibethinus L.) is a major economic crop native to Southeast Asian countries, including Thailand. Accordingly, understanding durian fruit ripening is an important factor in its market worldwide, owing to the fact that it is a climacteric fruit with a strikingly limited shelf life. However, knowledge regarding the molecular regulation of durian fruit ripening is still limited. Herein, we focused on cytochrome P450, a large enzyme family that regulates many biosynthetic pathways of plant metabolites and phytohormones. Deep mining of the durian genome and transcriptome libraries led to the identification of all P450s that are potentially involved in durian fruit ripening. Gene expression validation by RT-qPCR showed a high correlation with the transcriptome libraries at five fruit ripening stages. In addition to aril-specific and ripening-associated expression patterns, putative P450s that are potentially involved in phytohormone metabolism were selected for further study. Accordingly, the expression of CYP72, CYP83, CYP88, CYP94, CYP707, and CYP714 was significantly modulated by external treatment with ripening regulators, suggesting possible crosstalk between phytohormones during the regulation of fruit ripening. Interestingly, the expression levels of CYP88, CYP94, and CYP707, which are possibly involved in gibberellin, jasmonic acid, and abscisic acid biosynthesis, respectively, were significantly different between fast- and slow-post-harvest ripening cultivars, strongly implying important roles of these hormones in fruit ripening. Taken together, these phytohormone-associated P450s are potentially considered additional molecular regulators controlling ripening processes, besides ethylene and auxin, and are economically important biological traits.

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Biosynthesis of cyanogenic glucosides in Phaseolus lunatus and the evolution of oxime‐based defenses

Cited by 24 publications

References 56 publications

Dual‐species origin of an adaptive chemical defense polymorphism

Dual‐species origin of an adaptive chemical defense polymorphism

The fern CYPome: Fern-specific cytochrome P450 family involved in convergent evolution of chemical defense

Genome-wide identification and expression profiling of durian CYPome related to fruit ripening

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