Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins

Río, José C. del; Rencoret, Jorge; Gutiérrez, Ana; Kim, Hoon; Ralph, John

doi:10.1104/pp.17.00362

Cited by 81 publications

(52 citation statements)

References 44 publications

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“…Extractive content was reported 7-10% (Li et al, 2018;Queirós et al, 2019) with a high amount of phenolics, including flavonoids and tannins (Queirós et al, 2019). Recently hydroxystilbenes, a class of nonflavonoid polyphenolics, have been found to be part of the lignin structure of palm fruit endocarps based on nuclear magnetic resonance spectroscopy (Carlos Del Rio et al, 2017;Rencoret et al, 2018). The incorporation of piceatannol into the lignin polymer was suggested to have a role in seed protection (Rencoret et al, 2018).…”

Section: Maturation Of the Shell By Impregnation And Dehydrationmentioning

confidence: 99%

From the Soft to the Hard: Changes in Microchemistry During Cell Wall Maturation of Walnut Shells

et al. 2020

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The walnut shell is a hard and protective layer that provides an essential barrier between the seed and its environment. The shell is based on only one unit cell type: the polylobate sclerenchyma cell. For a better understanding of the interlocked walnut shell tissue, we investigate the structural and compositional changes during the development of the shell from the soft to the hard state. Structural changes at the macro level are explored by X-ray tomography and on the cell and cell wall level various microscopic techniques are applied. Walnut shell development takes place beneath the outer green husk, which protects and delivers components during the development of the walnut. The cells toward this outer green husk have the thickest and most lignified cell walls. With maturation secondary cell wall thickening takes place and the amount of all cell wall components (cellulose, hemicelluloses and especially lignin) is increased as revealed by FTIR microscopy. Focusing on the cell wall level, Raman imaging showed that lignin is deposited first into the pectin network between the cells and cell corners, at the very beginning of secondary cell wall formation. Furthermore, Raman imaging of fluorescence visualized numerous pits as a network of channels, connecting all the interlocked polylobate walnut shells. In the final mature stage, fluorescence increased throughout the cell wall and a fluorescent layer was detected toward the lumen in the inner part. This accumulation of aromatic components is reminiscent of heartwood formation of trees and is suggested to improve protection properties of the mature walnut shell. Understanding the walnut shell and its development will inspire biomimetic material design and packaging concepts, but is also important for waste valorization, considering that walnuts are the most widespread tree nuts in the world.

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Section: Maturation Of the Shell By Impregnation And Dehydrationmentioning

confidence: 99%

From the Soft to the Hard: Changes in Microchemistry During Cell Wall Maturation of Walnut Shells

et al. 2020

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“…What could be the functional and ecological significances of the three different types of sco clusters? In addition to the inhibitory effects of diverse stilbenes against fungi colonizing both living and decaying plant tissues (Celimene et al, ; Jeandet et al, ), some stilbenes (e.g., piceatannol and resveratrol) were recently shown to cross‐couple with monolignols during lignification of the cell wall (Carlos Del Río et al, ), where they may be expected to be released during lignin degradation processes typically carried out by saprotrophic fungi. Consequently, as particular fungal lineages frequently shift between different hosts and nutritional modes, the benefit of acquiring and optimizing mechanisms to degrade different types of stilbenes may wax and wane as populations disperse across heterogeneous environments.…”

Section: Discussionmentioning

confidence: 99%

“…Stilbene biosynthesis has convergently evolved at least four times across the plant kingdom (Han, Zhao, Wang, Zhu, & Liu, ; Tropf, Lanz, Rensing, Schröder, & Schröder, ), and numerous plant lineages produce distinct suites of stilbene derivatives (Chong et al, ). Stilbenes are important components of constitutive and inducible plant defences, often with broad‐spectrum antifungal activity (Celimene, Micales, Ferge, & Young, ; Celimene, Smith, Young, & Stanosz, ; Jeandet et al, ), and some form lignin monomers that contribute to plant cell wall integrity (Carlos Del Río et al, ). The ability to degrade or neutralize stilbenes in some fungal pathogens can be directly associated with their ability to colonize host tissue (Hammerbacher et al, ; Wadke et al, ).…”

Section: Introductionmentioning

confidence: 99%

Fungal adaptation to plant defences through convergent assembly of metabolic modules

2018

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The ongoing diversification of plant defence compounds exerts dynamic selection pressures on the microorganisms that colonize plant tissues. Evolutionary processes that generate resistance towards these compounds increase microbial fitness by giving access to plant resources and increasing pathogen virulence. These processes entail sequence‐based mechanisms that result in adaptive gene functions, and combinatorial mechanisms that result in novel syntheses of existing gene functions. However, the priority and interactions among these processes in adaptive resistance remain poorly understood. Using a combination of molecular genetic and computational approaches, we investigated the contributions of sequence‐based and combinatorial processes to the evolution of fungal metabolic gene clusters encoding stilbene cleavage oxygenases (SCOs), which catalyse the degradation of biphenolic plant defence compounds known as stilbenes into monophenolic molecules. We present phylogenetic evidence of convergent assembly among three distinct types of SCO gene clusters containing alternate combinations of phenolic catabolism. Multiple evolutionary transitions between different cluster types suggest recurrent selection for distinct gene assemblages. By comparison, we found that the substrate specificities of heterologously expressed SCO enzymes encoded in different clusters types were all limited to stilbenes and related molecules with a 4′‐OH group, and differed modestly in substrate range and activity under the experimental conditions. Together, this work suggests a primary role for genome structural rearrangement, and the importance of enzyme modularity, in promoting fungal metabolic adaptation to plant defence chemistry.

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“…What could be the functional and ecological significances of the three different types of sco clusters? In addition to the inhibitory effects of diverse stilbenes against fungi colonizing both living and decaying plant tissues (Celimene et al 1999; 2001; Jeandet et al 2010), some stilbenes (e.g., piceatannol and resveratrol) were recently shown to cross-couple with monolignols during lignification of the cell wall (Del Río et al 2017), where they may be expected to be released during lignin degradation processes typically carried out by saprotrophic fungi. Consequently, as particular fungal lineages frequently shift between different hosts and nutritional modes, the benefit of acquiring and optimizing mechanisms to degrade different types of stilbenes may wax and wane as populations disperse across heterogeneous environments.…”

Section: Discussionmentioning

confidence: 99%

“…Stilbene biosynthesis has convergently evolved at least four times across the plant kingdom (Tropf et al 1994; Han et al 2014), and numerous plant lineages produce distinct suites of stilbene derivatives (Chong et al 2009). Stilbenes are important components of constitutive and inducible plant defenses, often with broad-spectrum antifungal activity (Celimene et al 1999; 2001; Jeandet et al 2010), and some form lignin monomers that contribute to plant cell wall integrity (Del Río et al 2017). The ability to degrade or neutralize stilbenes in some fungal pathogens can be directly associated with their ability to colonize host tissue (Hammerbacher et al 2013; Wadke et al 2016).…”

Section: Introductionmentioning

confidence: 99%

Fungal adaptation to plant defenses through convergent assembly of metabolic modules

Gluck‐Thaler

Vijayakumar

Slot

2018

Preprint

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25The ongoing diversification of plant defense compounds exerts dynamic selection pressures on 26 the microorganisms that colonize plant tissues. Evolutionary processes that generate resistance 27 towards these compounds increase microbial fitness by giving access to plant resources and 28 increasing pathogen virulence. These processes entail sequence-based mechanisms that result in 29 adaptive gene functions, and combinatorial mechanisms that result in novel syntheses of existing 30 gene functions. However, the priority and interactions among these processes in adaptive 31 resistance remains poorly understood. Using a combination of molecular genetic and 32 computational approaches, we investigated the contributions of sequence-based and 33 combinatorial processes to the evolution of fungal metabolic gene clusters encoding stilbene 34 cleavage oxygenases (SCOs), which catalyze the degradation of biphenolic plant defense 35 compounds known as stilbenes into monophenolic molecules. We present phylogenetic evidence 36 of convergent assembly among three distinct types of SCO gene clusters containing alternate 37 combinations of phenolic catabolism. Multiple evolutionary transitions between different cluster 38 types suggest recurrent selection for distinct gene assemblages. By comparison, we found that 39 the substrate specificities of heterologously expressed SCO enzymes encoded in different 40 clusters types were all limited to stilbenes and related molecules with a 4'-OH group, and 41 differed modestly in substrate range and activity under the experimental conditions. Together, 42 this work suggests a primary role for genome structural rearrangement, and the importance of 43 enzyme modularity, in promoting fungal metabolic adaptation to plant defense chemistry. 44 45 106 remodeling can operate independently of sequence-based evolution. We analyzed the substrate 107 specificities of four heterologously expressed SCOs from different cluster types and unclustered 108 genomic regions, and found evidence for broad conservation of substrate specificity in both 109 unclustered and clustered SCOs, with only modest variation in the substrate specificity of SCOs 110 found in alternate cluster types. Conversely, we found evidence for multiple independent origins 111 of and repeated transitions between different types of sco clusters, consistent with selection 112 acting upon recurrent combinations of enzyme-encoding genes. These results suggest that the 113 6 reorganization of sco clusters may underpin adaptive shifts in stilbene degradation pathways, 114 while changes in enzymatic function may play a secondary role. 115 116 Methods 117 sco cluster retrieval and annotation 118 sco clusters were identified in publicly available genomes of 550 fungi (Table S1) as previously 119 described (Gluck-Thaler & Slot 2018). Briefly, all hits to a previously functionally characterized 120 SCO amino acid query (accession: EAA32528.1) were retrieved from predicted proteomes using 121 BLASTp from the BLAST suite v.2.2.25+ (Altschul et al....

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Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins

Cited by 81 publications

References 44 publications

From the Soft to the Hard: Changes in Microchemistry During Cell Wall Maturation of Walnut Shells

From the Soft to the Hard: Changes in Microchemistry During Cell Wall Maturation of Walnut Shells

Fungal adaptation to plant defences through convergent assembly of metabolic modules

Fungal adaptation to plant defenses through convergent assembly of metabolic modules

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