Maize specialized metabolome networks reveal organ-preferential mixed glycosides

Desmet, Sandrien; Saeys, Yvan; Verstaen, Kevin; Dauwe, Rébecca; Kim, Hoon; Niculaes, Claudiu; Fukushima, Atsushi; Goeminne, Geert; Vanholme, Ruben; Ralph, John; Boerjan, Wout; Morreel, Kris

doi:10.1016/j.csbj.2021.01.004

Cited by 16 publications

(27 citation statements)

References 67 publications

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“…These included not only caffeoyl shikimate ( 16 ), the known substrate of CSE, but also p ‐coumaroyl shikimate ( 15 ), feruloyl shikimate ( 18 ) and sinapoyl shikimate ( 22 ). In total, 21 characterized metabolites (including isomers) were hexosylated ( 1 – 14 , 17 , 20 , 21 , 23 ), most likely to reduce their toxicity and for storage in the vacuole (Desmet et al ., 2021; Dima et al ., 2015; Le Roy et al ., 2016). There were 244 metabolites that were significantly decreased (with a minimal 10‐fold change) in the mutants versus WTs, of which 36 could be characterized ( 26 – 51 , including 13 isomers; Table 2, Figure 1, Dataset S2, Figure S6).…”

Section: Resultsmentioning

confidence: 99%

CRISPR‐Cas9 editing of CAFFEOYL SHIKIMATE ESTERASE 1 and 2 shows their importance and partial redundancy in lignification in Populus tremula × P. alba

Vries

Brouckaert

Chanoca

et al. 2021

Plant Biotechnology Journal

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Summary Lignins are cell wall‐located aromatic polymers that provide strength and hydrophobicity to woody tissues. Lignin monomers are synthesized via the phenylpropanoid pathway, wherein CAFFEOYL SHIKIMATE ESTERASE (CSE) converts caffeoyl shikimate into caffeic acid. Here, we explored the role of the two CSE homologs in poplar (Populus tremula × P. alba). Reporter lines showed that the expression conferred by both CSE1 and CSE2 promoters is similar. CRISPR‐Cas9‐generated cse1 and cse2 single mutants had a wild‐type lignin level. Nevertheless, CSE1 and CSE2 are not completely redundant, as both single mutants accumulated caffeoyl shikimate. In contrast, the cse1 cse2 double mutants had a 35% reduction in lignin and associated growth penalty. The reduced‐lignin content translated into a fourfold increase in cellulose‐to‐glucose conversion upon limited saccharification. Phenolic profiling of the double mutants revealed large metabolic shifts, including an accumulation of p‐coumaroyl, 5‐hydroxyferuloyl, feruloyl and sinapoyl shikimate, in addition to caffeoyl shikimate. This indicates that the CSEs have a broad substrate specificity, which was confirmed by in vitro enzyme kinetics. Taken together, our results suggest an alternative path within the phenylpropanoid pathway at the level of the hydroxycinnamoyl‐shikimates, and show that CSE is a promising target to improve plants for the biorefinery.

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Section: Resultsmentioning

confidence: 99%

CRISPR‐Cas9 editing of CAFFEOYL SHIKIMATE ESTERASE 1 and 2 shows their importance and partial redundancy in lignification in Populus tremula × P. alba

Vries

Brouckaert

Chanoca

et al. 2021

Plant Biotechnology Journal

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“…For example, morphine, an alkaloid originally isolated from Papaver somniferum (commonly known as opium poppy), is generally known for the treatment of severe pain. A dominant alkaloid class in monocots, such as maize, are the benzoxazinoids [6,51]. Within plants, alkaloids are believed to serve as a storage form of nitrogen and as protection against herbivory [47].…”

Section: Alkaloidsmentioning

confidence: 99%

“…For example, morphine, an alkaloid originally isolated from Papaver somniferum (commonly known as opium poppy), is generally known for the treatment of severe pain. A dominant alkaloid class in monocots, such as maize, are the benzoxazinoids [6,51]. These indole-derived metabolites have been shown to be produced in response to European corn borer (Ostrinia nubilalis)-herbivory [52], and inoculation of maize leaves with pathogenic Curvularia lunata resulted in the accumulation of HDMBOA-glucoside [53].…”

Section: Alkaloidsmentioning

confidence: 99%

“…In the specialized metabolite profile of a plant extract, the common decorations are reflected in an overrepresentation of certain mass differences corresponding to the difference between two core structures. For example, in the maize specialized metabolome, the mass difference of 108.021 Da, corresponding to the difference between a phenylpropanoid and a flavonoid core structure, is observed between p-coumaric acid and naringenin, but also between caffeoyl hexose and eriodictyol 7-O-hexoside (hydroxylation and addition of a hexose to both) or between sinapoyl hexose and methoxy-homoeriodictyol (two methoxylations of both), as well as between dihydroxyindole-3-acetic acid (caffeoyl) hexoside and dihydroxyindole-3-acetic acid (eriodictyol-O-) hexoside (hydroxylation and addition of dihydroxyindole-3-acetic acid and hexose to both) [6]. The majority of plant specialized metabolites are glycosylated and/or acylated, with acylations being aromatic (p-coumaric, caffeic, ferulic, sinapic, gallic or p-hydroxybenzoic acids) or aliphatic (malonic, acetic, malic, succinic or oxalic acids).…”

Section: Diversity Of Decorationsmentioning

confidence: 99%

“…With the development of new metabolomics techniques, the improvement of detection methods and, in parallel, the ever-expanding number of metabolomics profiling studies performed on different plant species or plants subjected to different treatments or mutations, the number of known specialized plant metabolites is continuously increasing, hence leading to the impression that the number of different structures is infinite [1][2][3][4][5][6][7][8]. An aspect of plant biology that is not understood yet is the benefit of this huge structural diversity for plants.…”

Section: Introductionmentioning

confidence: 99%

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Origin and Function of Structural Diversity in the Plant Specialized Metabolome

Desmet

Morreel

Dauwe

2021

Plants

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The plant specialized metabolome consists of a multitude of structurally and functionally diverse metabolites, variable from species to species. The specialized metabolites play roles in the response to environmental changes and abiotic or biotic stresses, as well as in plant growth and development. At its basis, the specialized metabolism is built of four major pathways, each starting from a few distinct primary metabolism precursors, and leading to distinct basic carbon skeleton core structures: polyketides and fatty acid derivatives, terpenoids, alkaloids, and phenolics. Structural diversity in specialized metabolism, however, expands exponentially with each subsequent modification. We review here the major sources of structural variety and question if a specific role can be attributed to each distinct structure. We focus on the influences that various core structures and modifications have on flavonoid antioxidant activity and on the diversity generated by oxidative coupling reactions. We suggest that many oxidative coupling products, triggered by initial radical scavenging, may not have a function in se, but could potentially be enzymatically recycled to effective antioxidants. We further discuss the wide structural variety created by multiple decorations (glycosylations, acylations, prenylations), the formation of high-molecular weight conjugates and polyesters, and the plasticity of the specialized metabolism. We draw attention to the need for untargeted methods to identify the complex, multiply decorated and conjugated compounds, in order to study the functioning of the plant specialized metabolome.

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Energy‐Resolved Mass Spectrometry as a Tool for Identification of Lignin Depolymerization Products

et al. 2022

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Lignin is the largest source of bio-based aromatic compounds in nature, and its valorization is essential to the sustainability of lignocellulosic biorefining. Characterizing lignin-derived compounds remains challenging due to the heterogeneity of this biopolymer. Tandem mass spectrometry is a promising tool for lignin structural analytics, as fragmentation patterns of model compounds can be extrapolated to identify characteristic moieties in complex samples. This work extended previous resonance excitation-type collision-induced dissociation (CID) methods that identified lignin oligomers containing β-O-4, β-5, and β-β bonds, to also identify characteristics of 5-5, β-1, and 4-O-5 dimers, enabled by quadrupole time-of-flight (QTOF) CID with energy-resolved mass spectrometry (ERMS). Overall, QTOF-ERMS offers in-depth structural information and could ultimately contribute to tools for high-throughput lignin dimer identification.

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Maize specialized metabolome networks reveal organ-preferential mixed glycosides

Abstract: Graphical abstract

Cited by 16 publications

References 67 publications

CRISPR‐Cas9 editing of CAFFEOYL SHIKIMATE ESTERASE 1 and 2 shows their importance and partial redundancy in lignification in Populus tremula × P. alba

CRISPR‐Cas9 editing of CAFFEOYL SHIKIMATE ESTERASE 1 and 2 shows their importance and partial redundancy in lignification in Populus tremula × P. alba

Origin and Function of Structural Diversity in the Plant Specialized Metabolome

Energy‐Resolved Mass Spectrometry as a Tool for Identification of Lignin Depolymerization Products

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