A novel (possibly unique) lignin isolated from kenaf bast fibers had a high syringyl:guaiacyl ratio, was highly etherified, and was high in β-ether units with predominantly erythro stereochemistry. Moreover, it was extensively side-chain acetylated (primarily at γ), implicating 4-hydroxycinnamyl acetates as monomers in its biosynthesis.

Kenaf

Bast fibre

Side chain

10.1021/np960143s

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Citations (139)

Maize specialized metabolome networks reveal organ-preferential mixed glycosides

Computational and Structural Biotechnology Journal (2021)

Sandrien Desmet Yvan Saeys Kevin Verstaen Rébecca Dauwe Hoon Kim

Despite the scientific and economic importance of maize, little is known about its specialized metabolism. Here, five maize organs were profiled using different reversed-phase liquid chromatography-mass spectrometry methods. The resulting spectral metadata, combined with candidate substrate-product pair (CSPP) networks, allowed the structural characterization of 427 of the 5,420 profiled compounds, including phenylpropanoids, flavonoids, benzoxazinoids, and auxin-related compounds, among others. Only 75 of the 427 compounds were already described in maize. Analysis of the CSPP networks showed that phenylpropanoids are present in all organs, whereas other metabolic classes are rather organ-enriched. Frequently occurring CSPP mass differences often corresponded with glycosyl- and acyltransferase reactions. The interplay of glycosylations and acylations yields a wide variety of mixed glycosides, bearing substructures corresponding to the different biochemical classes. For example, in the tassel, many phenylpropanoid and flavonoid-bearing glycosides also contain auxin-derived moieties. The characterized compounds and mass differences are an important step forward in metabolic pathway discovery and systems biology research. The spectral metadata of the 5,420 compounds is publicly available (DynLib spectral database, https://bioit3.irc.ugent.be/dynlib/).

Phenylpropanoid

Metabolome

10.1016/j.csbj.2021.01.004

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Citations (18)

Discovery of Lignin in Seaweed Reveals Convergent Evolution of Cell-Wall Architecture

Current Biology (2009)

Patrick T. Martone José M. Estevez Fachuang Lu K. Ruel Mark W. Denny

Convergent evolution

Secondary cell wall

Red algae

10.1016/j.cub.2008.12.031

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Citations (424)

Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol

Journal of Agricultural and Food Chemistry (1992)

Stéphane Quideau John Ralph

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTFacile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcoholStephane. Quideau and John. RalphCite this: J. Agric. Food Chem. 1992, 40, 7, 1108–1110Publication Date (Print):July 1, 1992Publication History Published online1 May 2002Published inissue 1 July 1992https://doi.org/10.1021/jf00019a003RIGHTS & PERMISSIONSArticle Views2012Altmetric-Citations144LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (323 KB) Get e-Alertsclose Get e-Alerts

Coniferyl alcohol

Altmetrics

10.1021/jf00019a003

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Citations (171)

Understanding the Physicochemical Characteristics and the Improved Enzymatic Saccharification of Corn Stover Pretreated with Aqueous and Gaseous Ammonia

BioEnergy Research (2015)

Chang Geun Yoo Hoon Kim Fachuang Lu Ali Azarpira Xuejun Pan

Abstract Physicochemical characteristics of corn stover pretreated by soaking in aqueous ammonia (SAA) and low-moisture anhydrous ammonia (LMAA) were compared and investigated. The glucan digestibility of the treated biomass reached 90 % (SAA) and 84 % (LMAA). The LMAA pretreatment enhanced the digestibility by cleaving cross-linkages between cell wall components, whereas the SAA pretreatment additionally improved the digestibility by efficiently removing a major portion of the lignin under mild reaction conditions without significant loss of carbohydrates. Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and gel permeation chromatography (GPC) revealed the structural and chemical transformations of lignin during the pretreatments. Both pretreatments effectively cleaved ferulate cell wall cross-linking that is associated with the recalcitrance of grass lignocellulosics toward enzymatic saccharification. Extracted lignin from SAA pretreatment was extensively depolymerized but retained “native” character, as evidenced by the retention of β-ether linkages.

Corn stover

Enzymatic Hydrolysis

Lignocellulosic Biomass

Gel permeation chromatography

10.1007/s12155-015-9662-6

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Citations (53)

A cinnamoyl esterase from Aspergillus niger can break plant cell wall cross-links without release of free diferulic acids

María‐Teresa García‐Conesa Paul A. Kroon John Ralph Fred A. Mellon I.J. Colquhoun

Aspergillus niger

Esterase

Source

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Citations (4)

Lignin-hydroxycinnamyl model compounds related to forage cell wall structure. 1. Ether-linked structures

Journal of Agricultural and Food Chemistry (1992)

Richard F. Helm John Ralph

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTLignin-hydroxycinnamyl model compounds related to forage cell wall structure. 1. Ether-linked structuresRichard F. Helm and John. RalphCite this: J. Agric. Food Chem. 1992, 40, 11, 2167–2175Publication Date (Print):November 1, 1992Publication History Published online1 May 2002Published inissue 1 November 1992https://pubs.acs.org/doi/10.1021/jf00023a025https://doi.org/10.1021/jf00023a025research-articleACS PublicationsRequest reuse permissionsArticle Views384Altmetric-Citations38LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

10.1021/jf00023a025

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Citations (46)

Hydroxycinnamaldehyde-derived benzofuran components in lignins

PLANT PHYSIOLOGY (2023)

Koichi Yoshioka Hoon Kim Fachuang Lu Nette De Ridder Ruben Vanholme

Abstract Lignin is an abundant polymer in plant secondary cell walls. Prototypical lignins derive from the polymerization of monolignols (hydroxycinnamyl alcohols), mainly coniferyl and sinapyl alcohol, via combinatorial radical coupling reactions and primarily via the endwise coupling of a monomer with the phenolic end of the growing polymer. Hydroxycinnamaldehyde units have long been recognized as minor components of lignins. In plants deficient in cinnamyl alcohol dehydrogenase, the last enzyme in the monolignol biosynthesis pathway that reduces hydroxycinnamaldehydes to monolignols, chain-incorporated aldehyde unit levels are elevated. The nature and relative levels of aldehyde components in lignins can be determined from their distinct and dispersed correlations in 2D 1H–13C-correlated nuclear magnetic resonance (NMR) spectra. We recently became aware of aldehyde NMR peaks, well resolved from others, that had been overlooked. NMR of isolated low-molecular-weight oligomers from biomimetic radical coupling reactions involving coniferaldehyde revealed that the correlation peaks belonged to hydroxycinnamaldehyde-derived benzofuran moieties. Coniferaldehyde 8-5-coupling initially produces the expected phenylcoumaran structures, but the derived phenolic radicals undergo preferential disproportionation rather than radical coupling to extend the growing polymer. As a result, the hydroxycinnamaldehyde-derived phenylcoumaran units are difficult to detect in lignins, but the benzofurans are now readily observed by their distinct and dispersed correlations in the aldehyde region of NMR spectra from any lignin or monolignol dehydrogenation polymer. Hydroxycinnamaldehydes that are coupled to coniferaldehyde can be distinguished from those coupled with a generic guaiacyl end-unit. These benzofuran peaks may now be annotated and reported and their structural ramifications further studied.

Monolignol

Coniferyl alcohol

Benzofuran

10.1093/plphys/kiad514

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Citations (4)