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Highly Acylated (Acetylated and/or p-Coumaroylated) Native Lignins from Diverse Herbaceous Plants
Abstract
The structure of lignins isolated from the herbaceous plants sisal ( Agave sisalana), kenaf ( Hibiscus cannabinus), abaca ( Musa textilis) and curaua ( Ananas erectifolius) has been studied upon spectroscopic (2D-NMR) and chemical degradative (derivatization followed by reductive cleavage) methods. The analyses demonstrate that the structure of the lignins from these plants is highly remarkable, being extensively acylated at the gamma-carbon of the lignin side chain (up to 80% acylation) with acetate and/or p-coumarate groups and preferentially over syringyl units. Whereas the lignins from sisal and kenaf are gamma-acylated exclusively with acetate groups, the lignins from abaca and curaua are esterified with acetate and p-coumarate groups. The structures of all these highly acylated lignins are characterized by a very high syringyl/guaiacyl ratio, a large predominance of beta- O-4' linkages (up to 94% of all linkages), and a strikingly low proportion of traditional beta-beta' linkages, which indeed are completely absent in the lignins from abaca and curaua. The occurrence of beta-beta' homocoupling and cross-coupling products of sinapyl acetate in the lignins from sisal and kenaf indicates that sinapyl alcohol is acetylated at the monomer stage and that, therefore, sinapyl acetate should be considered as a real monolignol involved in the lignification reactions.
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Citations
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Ibarra, D., Chávez, M. I., Rencoret, J., Del Río, J. C., Gutiérrez, A., Romero, J., Camarero, S., Martínez, M. J., Jiménez-Barbero, J., & Martínez, A. T. (2007) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf063728t · Cited by 139
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Cited by
del Río, J. C., Rencoret, J., Prinsen, P., Martínez, Á. T., Ralph, J., & Gutiérrez, A. (2012) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf301002n · Cited by 835
Self-citationSecondary cell wall biosynthesis
Zhong, R., Cui, D., & Ye, Z. (2019) · New Phytologist · doi:10.1111/nph.15537 · Cited by 373
Enzymatic delignification of plant cell wall: from nature to mill
Martínez, Á. T., Ruiz-Dueñas, F. J., Martínez, M. J., del Río, J. C., & Gutiérrez, A. (2009) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2009.05.002 · Cited by 334
Self-citationWang, H.-M., Yuan, T.-Q., Song, G.-Y., & Sun, R.-C. (2021) · Green Chemistry · doi:10.1039/d1gc00790d · Cited by 292
Unmasking the structural features and property of lignin from bamboo
Wen, J.-L., Xue, B.-L., Xu, F., Sun, R.-C., & Pinkert, A. (2013) · Industrial Crops and Products · doi:10.1016/j.indcrop.2012.05.041 · Cited by 273
Metadata
- Authors
- del Río, J. C., Rencoret, J., Marques, G., Gutiérrez, A., Ibarra, D., Santos, J. I., Jiménez-Barbero, J., Zhang, L., & Martínez, Á. T.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-09-30
- Volume
- 56
- Issue
- 20
- Pages
- 9525-9534
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W2045478349
- Cited by
- 191
- References
- 1
- FWCI
- 7.89
- Type
- journal article
- Language
- en
- Open access
- closed
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- del Río, J. C., Rencoret, J., Marques, G., Gutiérrez, A., Ibarra, D., Santos, J. I., Jiménez-Barbero, J., Zhang, L., & Martínez, Á. T. (2008). Highly Acylated (Acetylated and/or p-Coumaroylated) Native Lignins from Diverse Herbaceous Plants. Journal of Agricultural and Food Chemistry. https://doi.org/10.1021/jf800806h
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