The Pattern of Acetylation Defines the Priming Activity of Chitosan Tetramers

Basa, Sven; Nampally, Malathi; Honorato, Talita Lopes; Das, Subha Narayan; Podile, Appa Rao; Gueddari, Nour Eddine El; Moerschbacher, Bruno M.

doi:10.1021/jacs.9b11466

Cited by 77 publications

(62 citation statements)

References 66 publications

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“…It is furthermore well known that chitosan treatment can act as plant priming, enabling a faster and more efficient response to upcoming biotic or abiotic challenges ( Frost et al., 2008 ; Mauch-Mani et al., 2017 ), and chitosan has recently been shown to induce priming in rice cells ( Basa et al., 2020 ). Priming agents are thought to act on redox signaling, altering the overall oxidative environment of plant cells which eventually puts plants in an alarm state ( González-Bosch, 2018 ).…”

Section: Discussionmentioning

confidence: 99%

Transcriptome Analysis of Solanum Tuberosum Genotype RH89-039-16 in Response to Chitosan

2020

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Potato ( Solanum tuberosum L.) is the worldwide most important nongrain crop after wheat, rice, and maize. The autotetraploidy of the modern commercial potato makes breeding of new resistant and high-yielding cultivars challenging due to complicated and time-consuming identification and selection processes of desired crop features. On the other hand, plant protection of existing cultivars using conventional synthetic pesticides is increasingly restricted due to safety issues for both consumers and the environment. Chitosan is known to display antimicrobial activity against a broad range of plant pathogens and shows the ability to trigger resistance in plants by elicitation of defense responses. As chitosan is a renewable, biodegradable and nontoxic compound, it is considered as a promising next-generation plant-protecting agent. However, the molecular and cellular modes of action of chitosan treatment are not yet understood. In this study, transcriptional changes in chitosan-treated potato leaves were investigated via RNA sequencing. Leaves treated with a well-defined chitosan polymer at low concentration were harvested 2 and 5 h after treatment and their expression profile was compared against water-treated control plants. We observed 32 differentially expressed genes (fold change ≥ 1; p-value ≤ 0.05) 2 h after treatment and 83 differentially expressed genes 5 h after treatment. Enrichment analysis mainly revealed gene modulation associated with electron transfer chains in chloroplasts and mitochondria, accompanied by the upregulation of only a very limited number of genes directly related to defense. As chitosan positively influences plant growth, yield, and resistance, we conclude that activation of electron transfer might result in the crosstalk of different organelles via redox signals to activate immune responses in preparation for pathogen attack, concomitantly resulting in a generally improved metabolic state, fostering plant growth and development. This conclusion is supported by the rapid and transient production of reactive oxygen species in a typical oxidative burst in the potato leaves upon chitosan treatment. This study furthers our knowledge on the mode of action of chitosan as a plant-protecting agent, as a prerequisite for improving its ability to replace or reduce the use of less environmentally friendly agro-chemicals.

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Section: Discussionmentioning

confidence: 99%

Transcriptome Analysis of Solanum Tuberosum Genotype RH89-039-16 in Response to Chitosan

2020

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“…Clearly, such studies will open up a whole new dimension of chitosan research and development and will pave the way for third-generation chitosans with known and defined patterns of acetylation. A few studies already hint at the crucial role of PA on properties and bioactivities of chitosans, as recently reviewed [ 6 , 18 ], and a very recent publication unequivocally proved for the first time that the α-mono-acetylated chitosan tetramer with the GlcNAc unit at its non-reducing end had strong disease resistance priming activities in rice cells, while the priming activities sequentially decreased in the other three isomeric paCOS, and the ω-mono-acetylated one with the GlcNAc unit at the reducing end was completely inactive [ 79 ]. Importantly, this priming-active tetramer possessed no elicitor activity, i.e., it prepares plant cells to efficiently react to even low concentrations of a resistance reaction-inducing elicitor that would not trigger a naïve cell, but it does not induce such an energy-consuming and potentially self-destructing cellular resistance reaction by itself.…”

Section: Discussionmentioning

confidence: 99%

Preparation of Defined Chitosan Oligosaccharides Using Chitin Deacetylases

Bonin

Sreekumar

Cord‐Landwehr

et al. 2020

IJMS

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During the past decade, detailed studies using well-defined ‘second generation’ chitosans have amply proved that both their material properties and their biological activities are dependent on their molecular structure, in particular on their degree of polymerisation (DP) and their fraction of acetylation (FA). Recent evidence suggests that the pattern of acetylation (PA), i.e., the sequence of acetylated and non-acetylated residues along the linear polymer, is equally important, but chitosan polymers with defined, non-random PA are not yet available. One way in which the PA will influence the bioactivities of chitosan polymers is their enzymatic degradation by sequence-dependent chitosan hydrolases present in the target tissues. The PA of the polymer substrates in conjunction with the subsite preferences of the hydrolases determine the type of oligomeric products and the kinetics of their production and further degradation. Thus, the bioactivities of chitosan polymers will at least in part be carried by the chitosan oligomers produced from them, possibly through their interaction with pattern recognition receptors in target cells. In contrast to polymers, partially acetylated chitosan oligosaccharides (paCOS) can be fully characterised concerning their DP, FA, and PA, and chitin deacetylases (CDAs) with different and known regio-selectivities are currently emerging as efficient tools to produce fully defined paCOS in quantities sufficient to probe their bioactivities. In this review, we describe the current state of the art on how CDAs can be used in forward and reverse mode to produce all of the possible paCOS dimers, trimers, and tetramers, most of the pentamers and many of the hexamers. In addition, we describe the biotechnological production of the required fully acetylated and fully deacetylated oligomer substrates, as well as the purification and characterisation of the paCOS products.

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“…The DP of COS is crucial for the biological response, as size‐dependent recognition was observed in plant chitin receptors as well as in toll‐like receptors (TLR2) [7] . It has been suggested that the acetylation pattern (AP) of COS modulates the biological activity [8] and may explain the existence of sequence‐specific chitosan hydrolases in most organisms [9]…”

Section: Figurementioning

confidence: 99%

“…Sequence specificity or regioselectivity may be achieved enzymatically, [13] but only few of the required enzymes are available. To date, no general method to produce all possible patterns exists [8] . Alternatively, well‐defined but simple COS can be prepared by chemical synthesis using orthogonal protecting groups [14] and glycosylation conditions [15] .…”

Section: Figurementioning

confidence: 99%

Systematic Structural Characterization of Chitooligosaccharides Enabled by Automated Glycan Assembly

Tyrikos‐Ergas

Bordoni

Fittolani

et al. 2021

Chemistry A European J

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Chitin, ap olymer composed of b(1-4)-linked Nacetyl-glucosamine monomers,a nd its partially deacetylated analogue chitosan,a re abundantb iopolymersw ith outstandingm echanical as well as elastic properties. Their degradation products,c hitooligosaccharides (COS), can trigger the innate immune response in humans and plants.B othm aterial and biological propertiesa re dependent on polymer length, acetylation,a sw ell as the pH. Withoutw ell-defined samples, ac omplete molecular descriptiono ft hese factors is still missing. Automated glycan assembly (AGA)e nabled rapid access to synthetic well-defined COS. Chitin-cellulose hybrid oligomers were prepared as importantt ools for as ystematic structural analysis. Intramolecular interactions, identified by molecular dynamics simulations and NMR analysis,u nderscore the importanceo ft he chitosana mino group for the stabilization of specific geometries.

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The Pattern of Acetylation Defines the Priming Activity of Chitosan Tetramers

Cited by 77 publications

References 66 publications

Transcriptome Analysis of Solanum Tuberosum Genotype RH89-039-16 in Response to Chitosan

Transcriptome Analysis of Solanum Tuberosum Genotype RH89-039-16 in Response to Chitosan

Preparation of Defined Chitosan Oligosaccharides Using Chitin Deacetylases

Systematic Structural Characterization of Chitooligosaccharides Enabled by Automated Glycan Assembly

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