Diversity in lignan biosynthesis

Umezawa, Toshiaki

doi:10.1023/b:phyt.0000045487.02836.32

Cited by 277 publications

(250 citation statements)

References 76 publications

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“…Oligolignol profiling not only provides information about the lignin oligomers but also applies to the (neo) lignans: the secondary metabolites for which the biosynthesis also starts with the radical-radical (cross-) coupling of monolignols (Umezawa, 2003). (Neo)lignan biosynthesis might be more elaborate than previously thought.…”

Section: Discussionmentioning

confidence: 99%

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Morreel

Dima²,

Kim³

et al. 2010

Plant Physiol.

171

213

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Although the primary structure of proteins, nucleic acids, and carbohydrates can be readily determined, no sequencing method has been described yet for the second most abundant biopolymer on earth (i.e. lignin). Within secondary-thickened plant cell walls, lignin forms an aromatic mesh arising from the combinatorial radical-radical coupling of monolignols and many other less abundant monomers. This polymerization process leads to a plethora of units and linkage types that affect the physicochemical characteristics of the cell wall. Current methods to analyze the lignin structure focus only on the frequency of the major monomeric units and interunit linkage types but do not provide information on the presence of less abundant unknown units and linkage types, nor on how linkages affect the formation of neighboring linkages. Such information can only be obtained using a sequencing approach. Here, we describe, to our knowledge for the first time, a sequencing strategy for lignin oligomers using mass spectrometry. This strategy was then evaluated on the oligomers extracted from wild-type poplar (Populus tremula 3 Populus tremuloides) xylem. In total, 134 lignin trimers to hexamers were observed, of which 36 could be completely sequenced. Interestingly, based on molecular mass data of the unknown monomeric and dimeric substructures, at least 10 unknown monomeric units or interunit linkage types were observed, one of which was identified as an arylglycerol end unit.Lignin is an aromatic heteropolymer that is mainly present in secondary-thickened plant cell walls, allowing the transport of water and nutrients and providing the necessary strength for the plant to grow upwardly Vanholme et al., 2008Vanholme et al., , 2010. In angiosperms, lignin is predominantly composed of guaiacyl (G) and syringyl (S) units that are derived from combinatorial radical-radical coupling of the monolignols coniferyl and sinapyl alcohol, respectively Fig. 1A). Following oxidation of the monolignols by peroxidase and/or laccase, the resulting electron-delocalized radical has unpaired electron density at its 1-, 3-, O-4-, 5-, and 8-positions (Fig. 1B); note that much of the lignin literature uses Greek letters for the side chain, a, b, and g for the 7-, 8-, and 9-positions. As radical coupling at the 8-position is favored, coupling with another monolignol radical affords, after rearomatization, a mixture of dehydrodimers with 8-8-, 8-5-, and 8-O-4-linkages (Fig. 1C). Following dimerization, polymerization will continue by the coupling of the 8-position of an incoming monolignol radical to the O-4-position of the dimer's phenolic end. In the case of a G dimer, coupling can also occur, albeit at a lower frequency, to the 5-position. Thus, chain elongation creates 8-5-and 8-O-4-linkages (Adler, 1977). Besides the monolignols and other monomers that are present in minor amounts , the plasticity of lignin polymerization permits the incorporation of any phenolic that enters the lignification site, subject to its chemical cross-coupling propensit...

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Section: Discussionmentioning

confidence: 99%

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Morreel

Dima²,

Kim³

et al. 2010

Plant Physiol.

171

213

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“…The presence of Arg suggests that the common pathway of lignan biosynthesis, i.e. from Pin to Mat or Arg is also existed in A. thaliana as in other plant species (Davin and Lewis 2003;Suzuki and Umezawa 2007;Umezawa 2003).…”

Section: Discussionmentioning

confidence: 99%

Simultaneous quantification of lignans in Arabidopsis thaliana by highly sensitive capillary liquid chromatography-electrospray ionization-ion trap mass spectrometry

Okazawa

Hori

Okumura

et al. 2011

Plant Biotechnology

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“…Lignans are composed of two phenylpropanoid C 6 C 3 units linked by central carbon (C8) of their propyl side chains (Umezawa 2003;Suzuki and Umezawa 2007;Topcu and Demirkiran 2007). Their biosynthesis involves the shikimate pathway providing l-phenylalanine and required multiple enzymatic steps (Vogt 2010;Umezawa 2010;Thoge et al 2013;Wang et al 2013).…”

Section: Introductionmentioning

confidence: 99%

Lignan accumulation in two-phase cultures of Taxus x media hairy roots

Sykłowska-Baranek

Łysik

Jeziorek

et al. 2018

Plant Cell Tiss Organ Cult

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The biosynthetic potential for six lignans accumulation in two lines of Taxus x media hairy roots was investigated. The cultures of KT and ATMA hairy root lines were supplemented with precursors: coniferyl alcohol (CA 1, 10 or 100 µM) and/or l-phenylalanine (100 µM PHEN) and/or methyl jasmonate (100 µM MeJa). Moreover the two-phase in vitro cultures supported with perfluorodecalin (PFD) as a gas carrier and in situ extrahent were used. The hairy root lines differed in lignan production profiles. In the control untreated cultures KT roots did not accumulate secoisolariciresinol and lariciresinol while ATMA roots did not accumulate matairesinol. In ATMA roots the treatment with CA (1 or 10 µM) resulted in the production of lariciresinol and secoisolariciresinol whereas solely lariciresinol was present after 100 µM CA application. Elicitation with 1 µM CA and MeJa yielded with hydroxymatairesinol aglyca and lariciresinol glucosides with their highest content 37.88 and 3.19 µg/g DW, respectively. The stimulatory effect of simultaneous treatment with 1 µM CA, PHEN and MeJa on lignan production was observed when the cultures were supplemented with PFD-aerated or degassed. In ATMA root cultures these applied conditions were the most favourable for matairesinol content which amounted to 199.86 and 160.25 µg/g DW in PFD-aerated and PFD-degassed supported cultures, respectively. In KT root cultures solely, hydroxymatairesinol and coniferin/CA content was enhanced with their highest yield 59.29 and 134.60 µg/g DW in PFD-aerated and PFD-degassed cultures, respectively.

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Diversity in lignan biosynthesis

Cited by 277 publications

References 76 publications

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Mass Spectrometry-Based Sequencing of Lignin Oligomers

Simultaneous quantification of lignans in Arabidopsis thaliana by highly sensitive capillary liquid chromatography-electrospray ionization-ion trap mass spectrometry

Lignan accumulation in two-phase cultures of Taxus x media hairy roots

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