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Title: 31P NMR Characterization of Tricin and Its Structurally Similar Flavonoids

Abstract

Tricin, a flavonoid metabolite, has been recently identified as a component of lignin in select monocot plants. This finding has initiated consideration on updating the lignin biosynthesis pathway. Here, we report a rapid method of determination of tricin in corn stover lignin, based on 31P nuclear magnetic resonance (NMR) spectroscopy by phosphitylating with 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (TMDP). Nine other flavonoids, with similar structure to tricin, have also been examined using the current method. The application of 31P NMR enables rapid identification of tricin-like flavonoids in the heterogeneous lignin polymer. The well resolved spectroscopic peaks from these derivatized flavonoids and lignin functional groups provide important information for the determination of flavonoids individually or their association with lignin.

Authors:
 [1];  [1];  [1];  [2]
  1. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). BioEnergy Science Center (BESC), Biosciences Division; Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Joint Institute for Biological Sciences (JICS)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). BioEnergy Science Center (BESC), Biosciences Division; Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Joint Institute for Biological Sciences (JICS); Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemical and Biomolecular Engineering; Univ. of Tennessee, Knoxville, TN (United States). Inst. of Agriculture, Center for Renewable Carbon, Dept. of Forestry, Wildlife, and Fisheries
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). BioEnergy Science Center (BESC); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Joint Institute for Biological Sciences (JICS)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1356916
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Chemistry Select
Additional Journal Information:
Journal Volume: 2; Journal Issue: 12; Journal ID: ISSN 2365-6549
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; biomass; tricin; lavonoids; NMR spectroscopy; lignin

Citation Formats

Li, Mi, Pu, Yunqiao, Tschaplinski, Timothy J., and Ragauskas, Arthur J. 31P NMR Characterization of Tricin and Its Structurally Similar Flavonoids. United States: N. p., 2017. Web. doi:10.1002/slct.201700735.
Li, Mi, Pu, Yunqiao, Tschaplinski, Timothy J., & Ragauskas, Arthur J. 31P NMR Characterization of Tricin and Its Structurally Similar Flavonoids. United States. doi:10.1002/slct.201700735.
Li, Mi, Pu, Yunqiao, Tschaplinski, Timothy J., and Ragauskas, Arthur J. Mon . "31P NMR Characterization of Tricin and Its Structurally Similar Flavonoids". United States. doi:10.1002/slct.201700735. https://www.osti.gov/servlets/purl/1356916.
@article{osti_1356916,
title = {31P NMR Characterization of Tricin and Its Structurally Similar Flavonoids},
author = {Li, Mi and Pu, Yunqiao and Tschaplinski, Timothy J. and Ragauskas, Arthur J.},
abstractNote = {Tricin, a flavonoid metabolite, has been recently identified as a component of lignin in select monocot plants. This finding has initiated consideration on updating the lignin biosynthesis pathway. Here, we report a rapid method of determination of tricin in corn stover lignin, based on 31P nuclear magnetic resonance (NMR) spectroscopy by phosphitylating with 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane (TMDP). Nine other flavonoids, with similar structure to tricin, have also been examined using the current method. The application of 31P NMR enables rapid identification of tricin-like flavonoids in the heterogeneous lignin polymer. The well resolved spectroscopic peaks from these derivatized flavonoids and lignin functional groups provide important information for the determination of flavonoids individually or their association with lignin.},
doi = {10.1002/slct.201700735},
journal = {Chemistry Select},
number = 12,
volume = 2,
place = {United States},
year = {Mon Apr 24 00:00:00 EDT 2017},
month = {Mon Apr 24 00:00:00 EDT 2017}
}

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Cited by: 2 works
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Works referenced in this record:

Lignin Valorization: Improving Lignin Processing in the Biorefinery
journal, May 2014

  • Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.
  • Science, Vol. 344, Issue 6185, p. 1246843-1246843
  • DOI: 10.1126/science.1246843

Lignin Biosynthesis
journal, June 2003