Passive Membrane Transport of Lignin-Related Compounds

Joshua Vermaas, Michael Crowley, Gregg Beckham, Richard Dixon, Fang Chen, Shawn Mansfield, Wout Boerjan, John Ralph

Research output: Contribution to journalArticlepeer-review

89 Scopus Citations

Abstract

Lignin is an abundant aromatic polymer found in plant secondary cell walls. In recent years, lignin has attracted renewed interest as a feedstock for bio-based chemicals via catalytic and biological approaches and has emerged as a target for genetic engineering to improve lignocellulose digestibility by altering its composition. In lignin biosynthesis and microbial conversion, small phenolic lignin precursors or degradation products cross membrane bilayers through an unidentified translocation mechanism prior to incorporation into lignin polymers (synthesis) or catabolism (bioconversion), with both passive and transporterassisted mechanisms postulated. To test the passive permeation potential of these phenolics, we performed molecular dynamics simulations for 69 monomeric and dimeric lignin-related phenolics with 3 model membranes to determine the membrane partitioning and permeability coefficients for each compound. The results support an accessible passive permeation mechanism for most compounds, including monolignols, dimeric phenolics, and the flavonoid, tricin. Computed lignin partition coefficients are consistent with concentration enrichment near lipid carbonyl groups, and permeability coefficients are sufficient to keep pace with cellular metabolism. Interactions between methoxy and hydroxy groups are found to reduce membrane partitioning and improve permeability. Only carboxylate-modified or glycosylated lignin phenolics are predicted to require transporters for membrane translocation. Overall, the results suggest that most lignin-related compounds can passively traverse plant and microbial membranes on timescales commensurate with required biological activities, with any potential transport regulation mechanism in lignin synthesis, catabolism, or bioconversion requiring compound functionalization.

Original languageAmerican English
Pages (from-to)23117-23123
Number of pages7
JournalProceedings of the National Academy of Sciences of the United States of America
Volume116
Issue number46
DOIs
StatePublished - 12 Nov 2019

Bibliographical note

Publisher Copyright:
© 2019 National Academy of Sciences. All rights reserved.

NREL Publication Number

  • NREL/JA-2700-74621

Keywords

  • Biological funneling
  • Free energy calculation
  • Lignin biosynthesis
  • Lignin permeability
  • Molecular dynamics

Fingerprint

Dive into the research topics of 'Passive Membrane Transport of Lignin-Related Compounds'. Together they form a unique fingerprint.

Cite this