Naturally p-Hydroxybenzoylated Lignins in Palms

Fachuang Lu, Steven D. Karlen, Matt Regner, Hoon Kim, Sally A. Ralph, Run Cang Sun, Ken ichi Kuroda, Mary Ann Augustin, Raymond Mawson, Henry Sabarez, Tanoj Singh, Gerardo Jimenez-Monteon, Sarani Zakaria, Stefan Hill, Philip J. Harris, Wout Boerjan, Curtis G. Wilkerson, Shawn D. Mansfield, John Ralph

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

The industrial production of palm oil concurrently generates a substantial amount of empty fruit bunch (EFB) fibers that could be used as a feedstock in a lignocellulose-based biorefinery. Lignin byproducts generated by this process may offer opportunities for the isolation of value-added products, such as p-hydroxybenzoate (pBz), to help offset operating costs. Analysis of the EFB lignin by nuclear magnetic resonance (NMR) spectroscopy clearly revealed the presence of bound acetate and pBz, with saponification revealing that 1.1 wt% of the EFB was pBz; with a lignin content of 22.7 %, 4.8 % of the lignin is pBz that can be obtained as a pure component for use as a chemical feedstock. Analysis of EFB lignin by NMR and derivatization followed by reductive cleavage (DFRC) showed that pBz selectively acylates the γ-hydroxyl group of S units. This selectivity suggests that pBz, analogously with acetate in kenaf, p-coumarate in grasses, and ferulate in a transgenic poplar augmented with a feruloyl-CoA monolignol transferase (FMT), is incorporated into the growing lignin chain via its γ-p-hydroxybenzoylated monolignol conjugate. Involvement of such conjugates in palm lignification is proven by the observation of novel p-hydroxybenzoylated non-resinol β–β-coupled units in the lignins. Together, the data implicate the existence of p-hydroxybenzoyl-CoA:monolignol transferases that are involved in lignification in the various willows (Salix spp.), poplars and aspen (Populus spp., family Salicaceae), and palms (family Arecaceae) that have p-hydroxybenzoylated lignins. Even without enhancing the levels by breeding or genetic engineering, current palm oil EFB ‘wastes’ should be able to generate a sizeable stream of p-hydroxybenzoic acid that offers opportunities for the development of value-added products derived from the oil palm industry.

Original languageEnglish
Pages (from-to)934-952
Number of pages19
JournalBioenergy Research
Volume8
Issue number3
DOIs
Publication statusPublished - 8 Sep 2015

Fingerprint

Lignin
lignin
Fruits
Palm oil
fruits
value-added products
lignification
palm oils
feedstocks
transferases
Feedstocks
nuclear magnetic resonance spectroscopy
acetates
Nuclear magnetic resonance
Saponification
biorefining
kenaf
Genetic engineering
Salicaceae
lignocellulose

Keywords

  • DFRC method
  • Lignin acylation
  • Monolignol
  • NMR
  • p-Hydroxybenzoic acid
  • Poplar
  • Transferase

ASJC Scopus subject areas

  • Agronomy and Crop Science
  • Energy (miscellaneous)
  • Renewable Energy, Sustainability and the Environment

Cite this

Lu, F., Karlen, S. D., Regner, M., Kim, H., Ralph, S. A., Sun, R. C., ... Ralph, J. (2015). Naturally p-Hydroxybenzoylated Lignins in Palms. Bioenergy Research, 8(3), 934-952. https://doi.org/10.1007/s12155-015-9583-4

Naturally p-Hydroxybenzoylated Lignins in Palms. / Lu, Fachuang; Karlen, Steven D.; Regner, Matt; Kim, Hoon; Ralph, Sally A.; Sun, Run Cang; Kuroda, Ken ichi; Augustin, Mary Ann; Mawson, Raymond; Sabarez, Henry; Singh, Tanoj; Jimenez-Monteon, Gerardo; Zakaria, Sarani; Hill, Stefan; Harris, Philip J.; Boerjan, Wout; Wilkerson, Curtis G.; Mansfield, Shawn D.; Ralph, John.

In: Bioenergy Research, Vol. 8, No. 3, 08.09.2015, p. 934-952.

Research output: Contribution to journalArticle

Lu, F, Karlen, SD, Regner, M, Kim, H, Ralph, SA, Sun, RC, Kuroda, KI, Augustin, MA, Mawson, R, Sabarez, H, Singh, T, Jimenez-Monteon, G, Zakaria, S, Hill, S, Harris, PJ, Boerjan, W, Wilkerson, CG, Mansfield, SD & Ralph, J 2015, 'Naturally p-Hydroxybenzoylated Lignins in Palms', Bioenergy Research, vol. 8, no. 3, pp. 934-952. https://doi.org/10.1007/s12155-015-9583-4
Lu F, Karlen SD, Regner M, Kim H, Ralph SA, Sun RC et al. Naturally p-Hydroxybenzoylated Lignins in Palms. Bioenergy Research. 2015 Sep 8;8(3):934-952. https://doi.org/10.1007/s12155-015-9583-4
Lu, Fachuang ; Karlen, Steven D. ; Regner, Matt ; Kim, Hoon ; Ralph, Sally A. ; Sun, Run Cang ; Kuroda, Ken ichi ; Augustin, Mary Ann ; Mawson, Raymond ; Sabarez, Henry ; Singh, Tanoj ; Jimenez-Monteon, Gerardo ; Zakaria, Sarani ; Hill, Stefan ; Harris, Philip J. ; Boerjan, Wout ; Wilkerson, Curtis G. ; Mansfield, Shawn D. ; Ralph, John. / Naturally p-Hydroxybenzoylated Lignins in Palms. In: Bioenergy Research. 2015 ; Vol. 8, No. 3. pp. 934-952.
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