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Title: Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins

Abstract

Lignin, the plant cell wall polymer that binds fibers together but makes processing difficult, is traditionally formed from three monomers, the so-called monolignols (p-coumaryl, coniferyl, and sinapyl alcohols). Recently, we discovered, in grass lignins, a phenolic monomer that falls outside the canonical lignin biosynthetic pathway, the flavone tricin. As we show here, palm fruit (macaúba [Acrocomia aculeata], carnauba [Copernicia prunifera], and coconut [Cocos nucifera]) endocarps contain lignin polymers derived in part from a previously unconsidered class of lignin monomers, the hydroxystilbenes, including the valuable compounds piceatannol and resveratrol. Piceatannol could be released from these lignins upon derivatization followed by reductive cleavage, a degradative method that cleaves b-ether bonds, indicating that at least a fraction is incorporated through labile ether bonds. Nuclear magnetic resonance spectroscopy of products from the copolymerization of piceatannol and monolignols confirms the structures in the natural polymer and demonstrates that piceatannol acts as an authentic monomer participating in coupling and cross-coupling reactions during lignification. Therefore, palm fruit endocarps contain a new class of stilbenolignin polymers, further expanding the definition of lignin and implying that compounds such as piceatannol and resveratrol are potentially available in what is now essentially a waste product.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [2]
  1. Instituto de Recursos Naturales y Agrobiología de Sevilla, Consejo Superior de Investigaciones Científicas, 41012 Seville, Spain
  2. Department of Energy Great Lakes Bioenergy Research Center, Wisconsin Energy Institute, University of Wisconsin, Madison, Wisconsin 53726, Department of Biochemistry, University of Wisconsin, Madison, Wisconsin 53706
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1573088
Alternate Identifier(s):
OSTI ID: 1427576
Grant/Contract Number:  
AGL2014-53730-R; CTQ2014-60764-JIN; 2014-40E-097; FC02-07ER64494
Resource Type:
Published Article
Journal Name:
Plant Physiology (Bethesda)
Additional Journal Information:
Journal Name: Plant Physiology (Bethesda) Journal Volume: 174 Journal Issue: 4; Journal ID: ISSN 0032-0889
Publisher:
American Society of Plant Biologists (ASPB)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Carlos del Río, José, Rencoret, Jorge, Gutiérrez, Ana, Kim, Hoon, and Ralph, John. Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins. United States: N. p., 2017. Web. doi:10.1104/pp.17.00362.
Carlos del Río, José, Rencoret, Jorge, Gutiérrez, Ana, Kim, Hoon, & Ralph, John. Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins. United States. doi:10.1104/pp.17.00362.
Carlos del Río, José, Rencoret, Jorge, Gutiérrez, Ana, Kim, Hoon, and Ralph, John. Tue . "Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins". United States. doi:10.1104/pp.17.00362.
@article{osti_1573088,
title = {Hydroxystilbenes Are Monomers in Palm Fruit Endocarp Lignins},
author = {Carlos del Río, José and Rencoret, Jorge and Gutiérrez, Ana and Kim, Hoon and Ralph, John},
abstractNote = {Lignin, the plant cell wall polymer that binds fibers together but makes processing difficult, is traditionally formed from three monomers, the so-called monolignols (p-coumaryl, coniferyl, and sinapyl alcohols). Recently, we discovered, in grass lignins, a phenolic monomer that falls outside the canonical lignin biosynthetic pathway, the flavone tricin. As we show here, palm fruit (macaúba [Acrocomia aculeata], carnauba [Copernicia prunifera], and coconut [Cocos nucifera]) endocarps contain lignin polymers derived in part from a previously unconsidered class of lignin monomers, the hydroxystilbenes, including the valuable compounds piceatannol and resveratrol. Piceatannol could be released from these lignins upon derivatization followed by reductive cleavage, a degradative method that cleaves b-ether bonds, indicating that at least a fraction is incorporated through labile ether bonds. Nuclear magnetic resonance spectroscopy of products from the copolymerization of piceatannol and monolignols confirms the structures in the natural polymer and demonstrates that piceatannol acts as an authentic monomer participating in coupling and cross-coupling reactions during lignification. Therefore, palm fruit endocarps contain a new class of stilbenolignin polymers, further expanding the definition of lignin and implying that compounds such as piceatannol and resveratrol are potentially available in what is now essentially a waste product.},
doi = {10.1104/pp.17.00362},
journal = {Plant Physiology (Bethesda)},
number = 4,
volume = 174,
place = {United States},
year = {2017},
month = {6}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1104/pp.17.00362

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Cited by: 10 works
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Works referencing / citing this record:

Fungal adaptation to plant defences through convergent assembly of metabolic modules
journal, December 2018

  • Gluck‐Thaler, Emile; Vijayakumar, Vinod; Slot, Jason C.
  • Molecular Ecology
  • DOI: 10.1111/mec.14943

Fungal adaptation to plant defences through convergent assembly of metabolic modules
journal, December 2018

  • Gluck‐Thaler, Emile; Vijayakumar, Vinod; Slot, Jason C.
  • Molecular Ecology
  • DOI: 10.1111/mec.14943

Lignins: Biosynthesis and Biological Functions in Plants
journal, January 2018

  • Liu, Qingquan; Luo, Le; Zheng, Luqing
  • International Journal of Molecular Sciences, Vol. 19, Issue 2
  • DOI: 10.3390/ijms19020335