31P NMR Characterization of Tricin and Its Structurally Similar Flavonoids

作者: Mi Li , Yunqiao Pu , Timothy J. Tschaplinski , Arthur J. Ragauskas

DOI: 10.1002/SLCT.201700735

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

参考文章(20)
A. J. Ragauskas, G. T. Beckham, M. J. Biddy, R. Chandra, F. Chen, M. F. Davis, B. H. Davison, R. A. Dixon, P. Gilna, M. Keller, P. Langan, A. K. Naskar, J. N. Saddler, T. J. Tschaplinski, G. A. Tuskan, C. E. Wyman, Lignin Valorization: Improving Lignin Processing in the Biorefinery Science. ,vol. 344, pp. 1246843- 1246843 ,(2014) , 10.1126/SCIENCE.1246843
Wu Lan, Fachuang Lu, Matthew Regner, Yimin Zhu, Jorge Rencoret, Sally A. Ralph, Uzma I. Zakai, Kris Morreel, Wout Boerjan, John Ralph, Tricin, A Flavonoid Monomer in Monocot Lignification Plant Physiology. ,vol. 167, pp. 1284- 1295 ,(2015) , 10.1104/PP.114.253757
F. Chen, Y. Tobimatsu, D. Havkin-Frenkel, R. A. Dixon, J. Ralph, A polymer of caffeyl alcohol in plant seeds Proceedings of the National Academy of Sciences of the United States of America. ,vol. 109, pp. 1772- 1777 ,(2012) , 10.1073/PNAS.1120992109
Stella Christophoridou, Apostolos Spyros, Photis Dais, 31P NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY OF POLYPHENOL-CONTAINING OLIVE OIL MODEL COMPOUNDS Phosphorus Sulfur and Silicon and The Related Elements. ,vol. 170, pp. 139- 157 ,(2001) , 10.1080/10426500108040591
Harri Heikkinen, Thomas Elder, Hannu Maaheimo, Stella Rovio, Jenni Rahikainen, Kristiina Kruus, Tarja Tamminen, Impact of steam explosion on the wheat straw lignin structure studied by solution-state nuclear magnetic resonance and density functional methods. Journal of Agricultural and Food Chemistry. ,vol. 62, pp. 10437- 10444 ,(2014) , 10.1021/JF504622J
Stella Christophoridou, Photis Dais, Novel Approach to the Detection and Quantification of Phenolic Compounds in Olive Oil Based on 31P Nuclear Magnetic Resonance Spectroscopy Journal of Agricultural and Food Chemistry. ,vol. 54, pp. 656- 664 ,(2006) , 10.1021/JF058138U
Mikhail Balakshin, Ewellyn Capanema, On the Quantification of Lignin Hydroxyl Groups With 31P and 13C NMR Spectroscopy Journal of Wood Chemistry and Technology. ,vol. 35, pp. 220- 237 ,(2015) , 10.1080/02773813.2014.928328
Hoon Kim, John Ralph, Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d6/pyridine-d5 Organic and Biomolecular Chemistry. ,vol. 8, pp. 576- 591 ,(2010) , 10.1039/B916070A
Y. Archipov, D. S. Argyropoulos, H. I. Bolker, C. Heitner, 31P NMR Spectroscopy in Wood Chemistry. I. Model Compounds Journal of Wood Chemistry and Technology. ,vol. 11, pp. 137- 157 ,(1991) , 10.1080/02773819108050267
D. S. Argyropoulos, 31P NMR in wood chemistry: A review of recent progress Research on Chemical Intermediates. ,vol. 21, pp. 373- 395 ,(1995) , 10.1007/BF03052265