Highly Decorated Lignins in Leaf Tissues of the Canary Island Date Palm <i>Phoenix canariensis</i>

Karlen, Steven D.; Smith, Rebecca A.; Kim, Hoon; Padmakshan, Dharshana; Bartuce, Allison; Mobley, Justin K.; Free, Heather C. A.; Smith, Bronwen G.; Harris, Philip J.; Ralph, John

doi:10.1104/pp.17.01172

Cited by 39 publications

(46 citation statements)

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“…The detailed procedure can be found in the Experimental Section below,a sw ell as in severalr ecent papers that have applied this methodt ot he analysiso fm onolignol conjugates. [29,30,34] In the course of our model compound studies, we found monolignol conjugate yields to be unusually lowi nc omparison to general yields published in theo riginal DFRC method paper,a lthoughm onomer yields were as expected. [35] As the data demonstrate (Figure 2), yield varied as af unctiono ft he moiety acylating the g-hydroxylu nit.…”

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confidence: 69%

Reductive Cleavage Method for Quantitation of Monolignols and Low‐Abundance Monolignol Conjugates

et al. 2018

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confidence: 69%

Reductive Cleavage Method for Quantitation of Monolignols and Low‐Abundance Monolignol Conjugates

et al. 2018

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“…All compounds synthesized for the determination of “theoretical” DFRC reaction yields, for authentication of products, and for use as internal standards, along with details regarding reaction kinetics can be found in the Supporting Information. The detailed procedure can be found in the Experimental Section below, as well as in several recent papers that have applied this method to the analysis of monolignol conjugates …”

Section: Methodsmentioning

confidence: 99%

Reductive Cleavage Method for Quantitation of Monolignols and Low‐Abundance Monolignol Conjugates

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As interest in biomass utilization has grown, the manipulation of lignin biosynthesis has received significant attention, such that recent work has demanded more robust lignin analytical methods. As the derivatization followed by reductive cleavage (DFRC) method is particularly effective for structurally characterizing natively acylated lignins, we used an array of synthetic β‐ether γ‐acylated model compounds to determine theoretical yields for all monolignol conjugates currently known to exist in lignin, and we synthesized a new set of deuterated analogs as internal standards for quantification using GC–MS/MS. Yields of the saturated ester conjugates ranged from 40 to 90 %, and NMR analysis revealed the presence of residual unsaturated conjugates in yields of 20 to 35 %. In contrast to traditional selected‐ion‐monitoring, we demonstrated the superior sensitivity and accuracy of multiple‐reaction‐monitoring detection methods, and further highlighted the inadequacy of traditional standards relative to isotopically labeled analogs.

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“…In addition, we performed thioacidolysis (Lapierre et al, 1986;Yamamura et al, 2012) and derivatization followed by reductive cleavage (DFRC) methods Ralph, 1997, 1999;Ralph and Lu, 1998;Smith et al, 2017). Ralph, 1997, 1999;Smith et al, 2017), along with its modification, DFRC-Pr (Ralph and Lu, 1998;Karlen et al, 2017), cleaves b-O-4 ether bonds without disrupting any c-ester linkages present and consequently releases quantifiable amounts of acylated degradation products (H DFRC-pCA , G DFRC-Ac , H DFRC-FA , G DFRC-pCA , G DFRC-Ac , G DFRC-FA , S DFRC-pCA , S DFRC-Ac and S DFRC-FA ) from c-acylated units along with non-acylated products (H DFRC-OH , G DFRC-OH and S DFRC-OH ) from c-OH units ( Figure 3). We also quantified wall-bound pCA and FA via saponification (Yamamura et al, 2011;Petrik et al, 2014) as well as cell wall polysaccharide units via a combination of trifluoroacetic acid (TFA) and sulfuric acid-catalyzed hydrolysis (Chen et al, 2012;Lam et al, 2017).…”

Section: Chemical Analysis Of Osc3 0 H1-kd Rice Cell Wallsmentioning

confidence: 99%

“…Extractive-free CWRs for chemical analysis were prepared according to Yamamura et al (2012) and further processed for NMR analysis according to Mansfield et al (2012) and Tobimatsu et al (2013) as described in Materials and Methods S1. Klason lignin assay (Hatfield et al, 1994), thioglycolic acid lignin assay (Suzuki et al, 2009), thioacidolysis (Yamamura et al, 2011;Yue et al, 2012), DFRC Regner et al, 2018), DFRC-Pr (Karlen et al, 2017), determination of cell-wall-bound pCA and FA content (Yamamura et al, 2012), and amorphous and crystalline neutral sugar composition analysis (Lam et al, 2017) were performed largely according to literature methods and as further described in Materials and Methods S1. Analytical parameters and multiple reaction monitoring (MRM) parameters used for DFRC analysis are shown in Tables S6 and S7.…”

Section: Cell Wall Analysismentioning

confidence: 99%

Downregulation of p‐COUMAROYL ESTER 3‐HYDROXYLASE in rice leads to altered cell wall structures and improves biomass saccharification

et al. 2018

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p-Coumaroyl ester 3-hydroxylase (C3'H) is a key enzyme involved in the biosynthesis of lignin, a phenylpropanoid polymer that is the major constituent of secondary cell walls in vascular plants. Although the crucial role of C3'H in lignification and its manipulation to upgrade lignocellulose have been investigated in eudicots, limited information is available in monocotyledonous grass species, despite their potential as biomass feedstocks. Here we address the pronounced impacts of C3'H deficiency on the structure and properties of grass cell walls. C3'H-knockdown lines generated via RNA interference (RNAi)-mediated gene silencing, with about 0.5% of the residual expression levels, reached maturity and set seeds. In contrast, C3'H-knockout rice mutants generated via CRISPR/Cas9-mediated mutagenesis were severely dwarfed and sterile. Cell wall analysis of the mature C3'H-knockdown RNAi lines revealed that their lignins were largely enriched in p-hydroxyphenyl (H) units while being substantially reduced in the normally dominant guaiacyl (G) and syringyl (S) units. Interestingly, however, the enrichment of H units was limited to within the non-acylated lignin units, with grass-specific γ-p-coumaroylated lignin units remaining apparently unchanged. Suppression of C3'H also resulted in relative augmentation in tricin residues in lignin as well as a substantial reduction in wall cross-linking ferulates. Collectively, our data demonstrate that C3'H expression is an important determinant not only of lignin content and composition but also of the degree of cell wall cross-linking. We also demonstrated that C3'H-suppressed rice displays enhanced biomass saccharification.

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Highly Decorated Lignins in Leaf Tissues of the Canary Island Date Palm Phoenix canariensis

Cited by 39 publications

References 38 publications

Reductive Cleavage Method for Quantitation of Monolignols and Low‐Abundance Monolignol Conjugates

Reductive Cleavage Method for Quantitation of Monolignols and Low‐Abundance Monolignol Conjugates

Reductive Cleavage Method for Quantitation of Monolignols and Low‐Abundance Monolignol Conjugates

Downregulation of p‐COUMAROYL ESTER 3‐HYDROXYLASE in rice leads to altered cell wall structures and improves biomass saccharification

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