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Tricin, a flavonoid monomer in monocot lignification

(2015) PLANT PHYSIOLOGY. 167(4). p.1284-1295
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Abstract
Tricin was recently discovered in lignin preparations from wheat (Triticum aestivum) straw and subsequently in all monocot samples examined. To provide proof that tricin is involved in lignification and establish the mechanism by which it incorporates into the lignin polymer, the 4'-O- beta-coupling products of tricin with the monolignols (p-coumaryl, coniferyl, and sinapyl alcohols) were synthesized along with the trimer that would result from its 4'-O-beta-couplingwith sinapyl alcohol and then coniferyl alcohol. Tricin was also found to cross couple with monolignols to form tricin-(4'-O-beta)-linked dimers in biomimetic oxidations using peroxidase/hydrogen peroxide or silver (I) oxide. Nuclear magnetic resonance characterization of gel permeation chromatography-fractionated acetylated maize (Zeamays) lignin revealed that the tricin moieties are found in even the highest molecular weight fractions, ether linked to lignin units, demonstrating that tricin is indeed incorporated into the lignin polymer. These findings suggest that tricin is fully compatible with lignification reactions, is an authentic lignin monomer, and, because it can only start a lignin chain, functions as a nucleation site for lignification in monocots. This initiation role helps resolve a long-standing dilemma that monocot lignin chains do not appear to be initiated by monolignol homodehydrodimerization as they are in dicots that have similar syringyl-guaiacyl compositions. The term flavonolignin is recommended for the racemic oligomers and polymers of monolignols that start from tricin (or incorporate other flavonoids) in the cell wall, in analogy with the existing term flavonolignan that is used for the low-molecular mass compounds composed of flavonoid and lignan moieties.
Keywords
BIOSYNTHESIS, FLAVONOLIGNANS, ALCOHOL, NMR METHOD, ERYTHRO RATIOS, OXIDE OXIDATION, BIOMIMETIC ROUTE, COUPLING REACTIONS, LIGNIN MODEL COMPOUNDS, WHEAT-STRAW

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MLA
Lan, Wu et al. “Tricin, a Flavonoid Monomer in Monocot Lignification.” PLANT PHYSIOLOGY 167.4 (2015): 1284–1295. Print.
APA
Lan, W., Lu, F., Regner, M., Zhu, Y., Rencoret, J., Ralph, S. A., Zakai, U. I., et al. (2015). Tricin, a flavonoid monomer in monocot lignification. PLANT PHYSIOLOGY, 167(4), 1284–1295.
Chicago author-date
Lan, Wu, Fachuang Lu, Matthew Regner, Yimin Zhu, Jorge Rencoret, Sally A Ralph, Uzma I Zakai, Kris Morreel, Wout Boerjan, and John Ralph. 2015. “Tricin, a Flavonoid Monomer in Monocot Lignification.” Plant Physiology 167 (4): 1284–1295.
Chicago author-date (all authors)
Lan, Wu, Fachuang Lu, Matthew Regner, Yimin Zhu, Jorge Rencoret, Sally A Ralph, Uzma I Zakai, Kris Morreel, Wout Boerjan, and John Ralph. 2015. “Tricin, a Flavonoid Monomer in Monocot Lignification.” Plant Physiology 167 (4): 1284–1295.
Vancouver
1.
Lan W, Lu F, Regner M, Zhu Y, Rencoret J, Ralph SA, et al. Tricin, a flavonoid monomer in monocot lignification. PLANT PHYSIOLOGY. 2015;167(4):1284–95.
IEEE
[1]
W. Lan et al., “Tricin, a flavonoid monomer in monocot lignification,” PLANT PHYSIOLOGY, vol. 167, no. 4, pp. 1284–1295, 2015.
@article{5986060,
  abstract     = {Tricin was recently discovered in lignin preparations from wheat (Triticum aestivum) straw and subsequently in all monocot samples examined. To provide proof that tricin is involved in lignification and establish the mechanism by which it incorporates into the lignin polymer, the 4'-O- beta-coupling products of tricin with the monolignols (p-coumaryl, coniferyl, and sinapyl alcohols) were synthesized along with the trimer that would result from its 4'-O-beta-couplingwith sinapyl alcohol and then coniferyl alcohol. Tricin was also found to cross couple with monolignols to form tricin-(4'-O-beta)-linked dimers in biomimetic oxidations using peroxidase/hydrogen peroxide or silver (I) oxide. Nuclear magnetic resonance characterization of gel permeation chromatography-fractionated acetylated maize (Zeamays) lignin revealed that the tricin moieties are found in even the highest molecular weight fractions, ether linked to lignin units, demonstrating that tricin is indeed incorporated into the lignin polymer. These findings suggest that tricin is fully compatible with lignification reactions, is an authentic lignin monomer, and, because it can only start a lignin chain, functions as a nucleation site for lignification in monocots. This initiation role helps resolve a long-standing dilemma that monocot lignin chains do not appear to be initiated by monolignol homodehydrodimerization as they are in dicots that have similar syringyl-guaiacyl compositions. The term flavonolignin is recommended for the racemic oligomers and polymers of monolignols that start from tricin (or incorporate other flavonoids) in the cell wall, in analogy with the existing term flavonolignan that is used for the low-molecular mass compounds composed of flavonoid and lignan moieties.},
  author       = {Lan, Wu and Lu, Fachuang and Regner, Matthew and Zhu, Yimin and Rencoret, Jorge and Ralph, Sally A and Zakai, Uzma I and Morreel, Kris and Boerjan, Wout and Ralph, John},
  issn         = {0032-0889},
  journal      = {PLANT PHYSIOLOGY},
  keywords     = {BIOSYNTHESIS,FLAVONOLIGNANS,ALCOHOL,NMR METHOD,ERYTHRO RATIOS,OXIDE OXIDATION,BIOMIMETIC ROUTE,COUPLING REACTIONS,LIGNIN MODEL COMPOUNDS,WHEAT-STRAW},
  language     = {eng},
  number       = {4},
  pages        = {1284--1295},
  title        = {Tricin, a flavonoid monomer in monocot lignification},
  url          = {http://dx.doi.org/10.1104/pp.114.253757},
  volume       = {167},
  year         = {2015},
}

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