Structural elucidation of the lignins from stems and foliage of Arundo donax Linn.

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 22, 2013, Pages 5361-5370

  You, Ting Ting ^a   Mao, Jian Zhen ^a   Yuan, Tong Qi ^a   Wen, Jia Long ^a   Xu, Feng ^a  

^a BEIJING FORESTRY UNIVERSITY   (China)

Author keywords

A. donax; DFRC; foliage; HSQC; lignin; stem; tricin

Indexed keywords

A. DONAX; DFRC; HSQC; STEM; TRICIN;

AGRICULTURE; ETHERS; MERCURY COMPOUNDS; ULTRAVIOLET SPECTROSCOPY; VEGETATION; WOOD;

LIGNIN;

BIOFUEL; FLAVONOID; LIGNIN; TRICIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CHINA; COMPARATIVE STUDY; CROP; GREENHOUSE EFFECT; HYDROLYSIS; ISOLATION AND PURIFICATION; MOLECULAR WEIGHT; PLANT LEAF; PLANT STEM; POACEAE;

BIOFUELS; CHINA; CROPS, AGRICULTURAL; FLAVONOIDS; GREENHOUSE EFFECT; HYDROLYSIS; LIGNIN; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; PLANT LEAVES; PLANT STEMS; POACEAE;

AGRICULTURE; ETHERS; LIGNINS; MERCURY COMPOUNDS; STEMS; WOOD;

ARUNDO DONAX;

EID: 84878627400     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf401277v     Document Type: Article

References (51)

1. Sarkhota, D. V.; Grunwalda, S.; Geb, Y.; Morgan, C. L. S. Total and available soil carbon fractions under the perennial grass Cynodon dactylon (L.) Pers and the bioenergy crop Arundo donax L Biomass Bioenerg. 2012, 41, 122-130
2. Nassi, N.; Angelini, L. G.; Bonari, E. Influence of fertilisation and harvest time on fuel quality of giant reed (Arundo donax L.) in central Italy Eur. J. Agronom. 2010, 32, 219-227
3. Bell, G. P. Ecology and management of Arundo donax, and approaches to riparian habitat restoration in southern California. In Book Plant Invasions: Studies from North America and Europe; Brock, J. H.; Wade, M.; Pysek, P.; Green, D., Eds.; Blackhuys Publishers: Leiden, The Netherlands, 1997; pp 103-113.
4. Mantineo, M.; D'Agosta, G. M.; Copani, V.; Patanè, C.; Cosentino, S. L. Biomass yield and energy balance of three perennial crops for energy use in the semi-arid Mediterranean environment Field Crop Res. 2009, 114, 204-213
5. Jeguirim, M.; Dorge, S.; Trouvé, G. Thermogravimetric analysis and emission characteristics of two energy crops in air atmosphere: Arundo donax and Miscanthus giganthus Bioresour. Technol. 2010, 101, 788-793
6. Barnoud, F.; Dutton, G. G. S.; Joseleau, J.-P. La d -xylane du roseau Aundo donax Carbohydr. Res. 1973, 27, 215-223
7. Shatalov, A. A.; Pereira, H. Carbohydrate behavior of Arundo donax L. in ethanol-alkali medium of variable composition during organosolv delignification Carbohydr. Polym. 2002, 49, 331-336 (Pubitemid 34466730)
8. Coelho, D.; Marques, G.; Gutiérrez, A.; Silvestre, A. J. D.; del Río, J. C. Chemical characterization of the lipophilic fraction of giant reed (Arundo donax) fibres used for pulp and paper manufacturing Ind. Crop Prod. 2007, 26, 229-236 (Pubitemid 46891788)
9. Fan, X. F.; Hou, X. C.; Zuo, H. T.; Wu, J. Y.; Duan, L. A. S. Biomass yield and quality of three kinds of bioenergy grasses in Beijing of China Sci. Agric. Sinica 2010, 43, 3316-3322
10. Ask, M.; Olofsson, K.; Di Felice, T.; Ruohonen, L.; Penttilä, M.; Lidén, G.; Olsson, L. Challenges in enzymatic hydrolysis and fermentation of pretreated Arundo donax revealed by a comparison between SHF and SSF Process Biochem. 2012, 47, 1452-1459
11. Boerjan, W.; Ralph, J.; Baucher, M. Lignin biosynthesis Annu. Rev. Plant Biol. 2003, 54, 519-546 (Pubitemid 37400004)
12. Ralph, J.; Lundquist, K.; Brunow, G.; Lu, F. C.; Kim, H.; Schatz, P. F.; Marita, J. M.; Hatfield, R. D.; Ralph, S. A.; Christensen, J. H.; Boerjan, W. Lignins: natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids Phytochem. Rev. 2004, 3, 29-60 (Pubitemid 41199638)
13. Zhang, X. H.; Chiang, V. L. Molecular cloning of 4-coumarate:coenzyme A ligase in loblolly pine and the roles of this enzyme in the biosynthesis of lignin in compression wood Plant Physiol. 1997, 113, 65-74 (Pubitemid 27111436)
14. Ikeda, T.; Holtman, K.; Kadla, J. F.; Chang, H. M.; Jameel, H. Studies on the effect of ball milling on lignin structure using a modified DFRC method J. Agric. Food Chem. 2002, 50, 129-135 (Pubitemid 34038520)
15. Björkman, A. Isolation of lignin from finely divided wood with neutral solvents Nature 1954, 174, 1057-1058
16. Lai, Y. Z.; Sarkanen, K. V. Isolation and structural studies. In Book Lignins: Occurrence, Formation, Structure and Reactions; Sarkanen, K. V.; Ludvig, C. H., Eds.; Wiley-Interscience: New York, 1971; pp 165-240.
17. Pew, J. C. Properties of powered wood and isolation of lignin by cellulytic enzymes Tappi J. 1957, 40, 553-558
18. Guerra, A.; Filpponen, I.; Lucia, L.; Argyropoulos, D. S. A comparative evaluation of three lignin isolation protocols with different wood species J. Agric. Food Chem. 2006, 54, 9696-9705 (Pubitemid 46158958)
19. Wu, S.; Argyropoulos, D. S. An improved method for isolating lignin in high yield and purity J. Pulp Paper Sci. 2003, 29, 235-240
20. Fasching, M.; Schröder, P.; Wollboldt, R. P.; Weber, H. K.; Sixta, H. A new and facile method for isolation of lignin from wood based on complete wood dissolution Holzforschung 2008, 62, 15-23 (Pubitemid 350223087)
21. Sun, R. C.; Lawther, M.; Banks, W. B. Effects of pretreatment temperature and alkali concentration on the composition of alkali-soluble lignins from wheat straw J. Appl. Polym. Sci. 1996, 62, 1473-1481 (Pubitemid 126535386)
22. Sette, M.; Wechselberger, R.; Crestini, C. Elucidation of lignin structure by quantitative 2D NMR J. Chem. Eur. 2011, 17, 9529-9535
23. del Río, J. C.; Rencoret, J.; Marques, G.; Gutiérrez, A.; Ibarra, D.; Santos, J. I.; Jiménez-Barbero, J.; Zhang, L.; Martínez, A. T. Highly acylated (acetylated and/or p -coumaroylated) native lignins from diverse herbaceous plants J. Agric. Food Chem. 2008, 56, 9525-9534
24. Lu, F. C.; Ralph, J. DFRC method for lignin analysis. 1. New method for β-aryl ether cleavage: lignin model studies J. Agric. Food Chem. 1997, 45, 4655-4660 (Pubitemid 127485821)
25. del Río, J. C.; Rencoret, J.; Gutierrez, A.; Nieto, L.; Jimenez-Barbero, J.; Martínez, A. T. Structural characterization of guaiacyl-rich lignins in flax (Linum usitatissimum) fibers and shives J. Agric. Food Chem. 2011, 59, 11088-11099
26. Sluiter, A.; Hames, B.; Ruiz, R.; Scarlata, C.; Sluiter, J.; Templeton, D.; Crocker, D. Determination of Structural Carbohydrates and Lignin in Biomass; Technical Report NREL/TP-510-42618; U.S. GPO: Washington, DC, 2008.
27. Asikkala, J.; Tamminen, T.; Argyropoulos, D. S. Accurate and reproducible determination of lignin molar mass by acetobromination J. Agric. Food Chem. 2012, 60, 8968-8973
28. 31P-NMR, FT-IR, and wet chemical methods Holzforschung 1994, 48, 387-394
29. del Río, J. C.; Rencoret, J.; Prinsen, P.; Martínez, A. T.; Ralph, J.; Gutiérrez, A. Structural characterization of wheat straw lignin as revealed by analytical pyrolysis, 2D-NMR, and reductive cleavage methods J. Agric. Food Chem. 2012, 60, 5922-5935
30. del Río, J. C.; Prinsen, P.; Rencoret, J.; Nieto, L.; Jiménez-Barbero, J.; Ralph, J.; Martínez, A. T.; Gutiérrez, A. Structural characterization of the lignin in the cortex and pith of elephant grass (Pennisetum purpureum) stems J. Agric. Food Chem. 2012, 60, 3619-3634
31. Hallac, B. B.; Sannigrahi, P.; Pu, Y.; Ray, M.; Murphy, R. J.; Ragauskas, A. J. Biomass characterization of Buddleja davidii: a potential feedstock for biofuel production J. Agric. Food Chem. 2009, 57, 1275-1281
32. Yuan, T. Q.; Sun, S. N.; Xu, F.; Sun, R. C. Structural characterization of lignin from triploid of Populus tomentosa Carr J. Agric. Food Chem. 2011, 59, 6605-6615
33. Buranov, A. U.; Mazza, G. Lignin in straw of herbaceous crops Ind. Crop Prod. 2008, 28, 237-259
34. Jääskeläinen, A. S.; Sun, Y.; Argyropoulos, D. S.; Tamminen, T.; Hortling, B. The effect of isolation method on the chemical structure of residual lignin Wood Sci. Technol. 2003, 37, 91-102
35. Seca, A. M.; Cavaleiro, J. A.; Domingues, F. M.; Silvestre, A. J.; Evtuguin, D.; Neto, C. P. Structural characterization of the lignin from the nodes and internodes of Arundo donax reed J. Agric. Food Chem. 2000, 48, 817-824 (Pubitemid 30194011)
36. Sun, R. C.; Lu, Q.; Sun, X. F. Physico-chemical and thermal characterization of lignins from Caligonum monogoliacum and Tamarix spp Polym. Degrad. Stab. 2001, 72, 229-238 (Pubitemid 32279445)
37. Faix, O. Classification of lignins from different botanical origins by FT-IR spectroscopy Holzforschung 1991, 45, 21-28
38. Boeriu, C. G.; Bravo, D.; Gosselink, R. J. A.; Dam, J. Characterisation of structure-dependent functional properties of lignin with infrared spectroscopy Ind. Crop Prod. 2004, 20, 205-218 (Pubitemid 39301118)
39. Jiao, J. J.; Zhang, Y.; Liu, C. M.; Liu, J. E.; Wu, X. Q.; Zhang, Y. Separation and purification of tricin from an antioxidant product derived from bamboo leaves J. Agric. Food Chem. 2007, 55, 10086-10092
40. Wen, J. L.; Sun, S. L.; Xue, B. L.; Sun, R..C. Quantitative structural characterization of the lignins from the stem and pith of bamboo (Phyllostachys pubescens). Holzforschung 2013, DOI: 10.1515/hf-2012-0162.
41. 31P and 2D NMR spectroscopy. The occurrence of ester bonds and α -O-4 substructures J. Agric. Food Chem. 1997, 45, 1212-1219 (Pubitemid 127476894)
42. Martínez, A. T.; Rencoret, J.; Marques, G.; Gutiérrez, A.; Ibarra, D.; Jiménez-Barbero, J.; del Río, J. C. Monolignol acylation and lignin structure in some nonwoody plants: a 2D NMR study Phytochemistry 2008, 69, 2831-2843
43. 5 Org. Biomol. Chem. 2010, 8, 576-591
44. del Río, J. C.; Rencoret, J.; Marques, G.; Li, J. B.; Gellerstedt, G.; Jimenez-Barbero, J.; Martínez, A. T.; Gutierrez, A. Structural characterization of the lignin from jute (Corchorus capsularis) fibers J. Agric. Food Chem. 2009, 57, 10271-10281
45. Lu, F. C.; Ralph, J. Novel tetrahydrofuran structures derived from β-β-coupling reactions involving sinapyl acetates in kenaf lignins Org. Biomol. Chem. 2008, 6, 3681-3694
46. Lu, F. C.; Ralph, J.; Novel β-β structures in lignins in corporating acylated monolignols Appita J. 2005, 223-237
47. Kuwabara, H.; Mouri, K.; Otsuka, H.; Kasai, R.; Yamasaki, K. Tricin from a Malagasy connaraceous plant with potent antihistaminic activity J. Nat. Prod. 2003, 66, 1273-1275 (Pubitemid 37204238)
48. Ralph, J.; Landucci, L. L. NMR of lignins. In Lignin and Lignans; Advances in Chemistry; Heitner, C.; Dimmel, D. R.; Schmidt, J. A., Eds.; CRC Press (Taylor & Francis Group): Boca Raton, FL, 2010; pp 137-234.
49. Lu, F. C.; Ralph, J. Detection and determination of p -coumaroylated units in lignins J. Agric. Food Chem. 1999, 47, 1988-1992 (Pubitemid 29438748)
50. Akiyama, T.; Matsumoto, Y.; Okuyama, T.; Meshitsuka, G. Ratio of erythro and thero form of β- O -4 structure in tension wood lignin Phytochemistry 2003, 64, 1157-1162 (Pubitemid 37295338)
51. Lu, F. C.; Ralph, J. The DFRC method for lignin analysis. 2. Monomers from isolated lignins J. Agric. Food Chem. 1998, 46, 547-552 (Pubitemid 128488420)