Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid

Yuki, Tobimatsu; Sasikumar, Elumalai; Grabber, John H.; Davidson, Christy L.; Xuejun, Pan; John, Ralph

doi:10.1002/cssc.201100573

Title: Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid

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Abstract

The plasticity of lignin biosynthesis should permit the inclusion of new compatible phenolic monomers, such as rosmarinic acid (RA) and analogous catechol derivatives, into cell-wall lignins that are consequently less recalcitrant to biomass processing. In vitro lignin polymerization experiments revealed that RA readily underwent peroxidase-catalyzed copolymerization with monolignols and lignin oligomers to form polymers with new benzodioxane inter-unit linkages. Incorporation of RA permitted extensive depolymerization of synthetic lignins by mild alkaline hydrolysis, presumably by cleavage of ester intra-unit linkages within RA. Copolymerization of RA with monolignols into maize cell walls by in situ peroxidases significantly enhanced alkaline lignin extractability and promoted subsequent cell wall saccharification by fungal enzymes. Incorporating RA also improved cell wall saccharification by fungal enzymes and by rumen microflora even without alkaline pretreatments, possibly by modulating lignin hydrophobicity and/or limiting cell wall cross-linking. Consequently, we anticipate that bioengineering approaches for partial monolignol substitution with RA and analogous plant hydroxycinnamates would permit more efficient utilization of plant fiber for biofuels or livestock production.

Authors:: Yuki, Tobimatsu; Sasikumar, Elumalai; Grabber, John H.; Davidson, Christy L.; Xuejun, Pan; John, Ralph

Publication Date:: Sun Apr 01 00:00:00 EDT 2012

Research Org.:: Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

OSTI Identifier:: 1152714

Resource Type:: Journal Article

Journal Name:: ChemSusChem

Additional Journal Information:: Journal Volume: 5; Journal Issue: 4; Journal ID: ISSN 1864-5631

Publisher:: ChemPubSoc Europe

Country of Publication:: United States

Language:: English

Citation Formats


                    Yuki, Tobimatsu, Sasikumar, Elumalai, Grabber, John H., Davidson, Christy L., Xuejun, Pan, and John, Ralph. Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid.  United States: N. p., 2012. 
        Web.  doi:10.1002/cssc.201100573.

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                    Yuki, Tobimatsu, Sasikumar, Elumalai, Grabber, John H., Davidson, Christy L., Xuejun, Pan, & John, Ralph. Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid.  United States.  https://doi.org/10.1002/cssc.201100573

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                    Yuki, Tobimatsu, Sasikumar, Elumalai, Grabber, John H., Davidson, Christy L., Xuejun, Pan, and John, Ralph. 2012.  
        "Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid".  United States.  https://doi.org/10.1002/cssc.201100573.

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@article{osti_1152714,

  title        = {Hydroxycinnamate Conjugates as Potential Monolignol Replacements: In vitro Lignification and Cell Wall Studies with Rosmarinic Acid},

  author       = {Yuki, Tobimatsu and Sasikumar, Elumalai and Grabber, John H. and Davidson, Christy L. and Xuejun, Pan and John, Ralph},

  abstractNote = {The plasticity of lignin biosynthesis should permit the inclusion of new compatible phenolic monomers, such as rosmarinic acid (RA) and analogous catechol derivatives, into cell-wall lignins that are consequently less recalcitrant to biomass processing. In vitro lignin polymerization experiments revealed that RA readily underwent peroxidase-catalyzed copolymerization with monolignols and lignin oligomers to form polymers with new benzodioxane inter-unit linkages. Incorporation of RA permitted extensive depolymerization of synthetic lignins by mild alkaline hydrolysis, presumably by cleavage of ester intra-unit linkages within RA. Copolymerization of RA with monolignols into maize cell walls by in situ peroxidases significantly enhanced alkaline lignin extractability and promoted subsequent cell wall saccharification by fungal enzymes. Incorporating RA also improved cell wall saccharification by fungal enzymes and by rumen microflora even without alkaline pretreatments, possibly by modulating lignin hydrophobicity and/or limiting cell wall cross-linking. Consequently, we anticipate that bioengineering approaches for partial monolignol substitution with RA and analogous plant hydroxycinnamates would permit more efficient utilization of plant fiber for biofuels or livestock production.},

  doi          = {10.1002/cssc.201100573},

  url          = {https://www.osti.gov/biblio/1152714},
  journal      = {ChemSusChem},

  issn         = {1864-5631},

  number       = 4,

  volume       = 5,

  place        = {United States},

  year         = {Sun Apr 01 00:00:00 EDT 2012},

  month        = {Sun Apr 01 00:00:00 EDT 2012}

}

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