DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Characteristics of Hot Water Extracts from the Bark of Cultivated Willow (Salix sp.)

Abstract

Willow bark is a rich source of heterogeneous polyphenolic compounds and a potential feedstock for biorefinery processes aiming at chemicals and fiber production. Here, mild hot water treatment of willow hybrid Karin was studied to find a practical means of isolating its non-cell-wall components for their utilization in a willow biorefinery proposed to aid valorization of the willow biomass. A short aqueous treatment of the bark at 80 °C liberated the extract in >20% yield under unpressurized conditions. The extract was characterized using mainly gas chromatography-mass spectrometry and one- and two-dimensional NMR techniques. Authentic analytes were applied to confirm the identification and quantification of the main components that were picein, (+)-catechin, triandrin, glucose, and fructose. Fructose was converted into 5-hydroxymethylfurfural in an acidic treatment which led to its condensation with the phenolic components and formation of a recalcitrant precipitate that should be avoided.

Authors:
 [1]; ORCiD logo [2];  [1];  [3];  [3];  [4];  [2];  [2]; ORCiD logo [3]; ORCiD logo [1]
  1. Aalto Univ. (Finland)
  2. Åbo Akademi Univ., Turku (Finland)
  3. Univ. of Wisconsin, Madison, WI (United States)
  4. Univ. of Helsinki (Finland); Technische Univ. Berlin (Germany)
Publication Date:
Research Org.:
Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER)
OSTI Identifier:
1505796
Grant/Contract Number:  
SC0018409
Resource Type:
Accepted Manuscript
Journal Name:
ACS Sustainable Chemistry & Engineering
Additional Journal Information:
Journal Volume: 6; Journal Issue: 4; Journal ID: ISSN 2168-0485
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; (+)-Catechin; 5-Hydroxymethylfurfural; Fructose; Picein; Triandrin; Willow bark

Citation Formats

Dou, Jinze, Xu, Wenyang, Koivisto, Jari J., Mobley, Justin K., Padmakshan, Dharshana, Kögler, Martin, Xu, Chunlin, Willför, Stefan, Ralph, John, and Vuorinen, Tapani. Characteristics of Hot Water Extracts from the Bark of Cultivated Willow (Salix sp.). United States: N. p., 2018. Web. doi:10.1021/acssuschemeng.8b00498.
Dou, Jinze, Xu, Wenyang, Koivisto, Jari J., Mobley, Justin K., Padmakshan, Dharshana, Kögler, Martin, Xu, Chunlin, Willför, Stefan, Ralph, John, & Vuorinen, Tapani. Characteristics of Hot Water Extracts from the Bark of Cultivated Willow (Salix sp.). United States. https://doi.org/10.1021/acssuschemeng.8b00498
Dou, Jinze, Xu, Wenyang, Koivisto, Jari J., Mobley, Justin K., Padmakshan, Dharshana, Kögler, Martin, Xu, Chunlin, Willför, Stefan, Ralph, John, and Vuorinen, Tapani. Wed . "Characteristics of Hot Water Extracts from the Bark of Cultivated Willow (Salix sp.)". United States. https://doi.org/10.1021/acssuschemeng.8b00498. https://www.osti.gov/servlets/purl/1505796.
@article{osti_1505796,
title = {Characteristics of Hot Water Extracts from the Bark of Cultivated Willow (Salix sp.)},
author = {Dou, Jinze and Xu, Wenyang and Koivisto, Jari J. and Mobley, Justin K. and Padmakshan, Dharshana and Kögler, Martin and Xu, Chunlin and Willför, Stefan and Ralph, John and Vuorinen, Tapani},
abstractNote = {Willow bark is a rich source of heterogeneous polyphenolic compounds and a potential feedstock for biorefinery processes aiming at chemicals and fiber production. Here, mild hot water treatment of willow hybrid Karin was studied to find a practical means of isolating its non-cell-wall components for their utilization in a willow biorefinery proposed to aid valorization of the willow biomass. A short aqueous treatment of the bark at 80 °C liberated the extract in >20% yield under unpressurized conditions. The extract was characterized using mainly gas chromatography-mass spectrometry and one- and two-dimensional NMR techniques. Authentic analytes were applied to confirm the identification and quantification of the main components that were picein, (+)-catechin, triandrin, glucose, and fructose. Fructose was converted into 5-hydroxymethylfurfural in an acidic treatment which led to its condensation with the phenolic components and formation of a recalcitrant precipitate that should be avoided.},
doi = {10.1021/acssuschemeng.8b00498},
journal = {ACS Sustainable Chemistry & Engineering},
number = 4,
volume = 6,
place = {United States},
year = {Wed Feb 28 00:00:00 EST 2018},
month = {Wed Feb 28 00:00:00 EST 2018}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 29 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Beyond Petrochemicals: The Renewable Chemicals Industry
journal, October 2011

  • Vennestrøm, P. N. R.; Osmundsen, C. M.; Christensen, C. H.
  • Angewandte Chemie International Edition, Vol. 50, Issue 45
  • DOI: 10.1002/anie.201102117

Platform biochemicals for a biorenewable chemical industry
journal, May 2008


Bio-Refinery as the Bio-Inspired Process to Bulk Chemicals
journal, February 2007

  • Sanders, Johan; Scott, Elinor; Weusthuis, Ruud
  • Macromolecular Bioscience, Vol. 7, Issue 2
  • DOI: 10.1002/mabi.200600223

Willow biomass obtained from different soils as a feedstock for energy
journal, November 2015


Valorization of bark for chemicals and materials: A review
journal, October 2013

  • Feng, Shanghuan; Cheng, Shuna; Yuan, Zhongshun
  • Renewable and Sustainable Energy Reviews, Vol. 26
  • DOI: 10.1016/j.rser.2013.06.024

High value triterpenic compounds from the outer barks of several Eucalyptus species cultivated in Brazil and in Portugal
journal, January 2011


Valorisation of softwood bark through extraction of utilizable chemicals. A review
journal, November 2017


Spruce bark as an industrial source of condensed tannins and non-cellulosic sugars
journal, January 2014


Characterization of condensed tannins and carbohydrates in hot water bark extracts of European softwood species
journal, December 2015


Morphology and Overall Chemical Characterization of Willow ( Salix sp.) Inner Bark and Wood: Toward Controlled Deconstruction of Willow Biomass
journal, June 2016

  • Dou, Jinze; Galvis, Leonardo; Holopainen-Mantila, Ulla
  • ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 7
  • DOI: 10.1021/acssuschemeng.6b00641

Pressurized hot water extraction (PHWE)
journal, April 2010


Pressurized hot water flow-through extraction of birch sawdust – Effects of sawdust density and sawdust size
journal, December 2014


Sustainable Films and Coatings from Hemicelluloses: A Review
journal, May 2008

  • Hansen, Natanya M. L.; Plackett, David
  • Biomacromolecules, Vol. 9, Issue 6
  • DOI: 10.1021/bm800053z

Hemicelluloses for fuel ethanol: A review
journal, July 2010


Bark salicylates and condensed tannins reduce vole browsing amongst cultivated dark-leaved willows (Salix myrsinifolia)
journal, September 2007


HPLC-MS/MS analysis of willow bark extracts contained in pharmaceutical preparations
journal, January 2005

  • Kammerer, Bernd; Kahlich, Rainer; Biegert, Claudia
  • Phytochemical Analysis, Vol. 16, Issue 6
  • DOI: 10.1002/pca.873

Medicinal potential of willow: A chemical perspective of aspirin discovery
journal, July 2010


Treatment of low back pain exacerbations with willow bark extract: a randomized double-blind study
journal, July 2000


Phenylpropanoids as the biologically active compounds of the medicinal plants and phytopharmaceuticals
journal, January 2013


Isolation, identification and antioxidative capacity of water-soluble phenylpropanoid compounds from Rhodiola crenulata
journal, October 2012


GC-MS determination of catechin and epicatechin levels in human plasma
journal, November 1997

  • Luthria, Devanand L.; Jones, A. Daniel; Donovan, Jennifer L.
  • Journal of High Resolution Chromatography, Vol. 20, Issue 11
  • DOI: 10.1002/jhrc.1240201111

Phenolic constituents in the leaves of northern willows: methods for the analysis of certain phenolics
journal, March 1985

  • Julkunen-Tiitto, Riitta
  • Journal of Agricultural and Food Chemistry, Vol. 33, Issue 2
  • DOI: 10.1021/jf00062a013

Two new phenolic water-soluble constituents from branch bark of Davidia involucrata
journal, April 2008


Preparation of Epimers of Tea Catechins by Heat Treatment
journal, January 1997

  • Seto, Ryota; Nakamura, Hironori; Nanjo, Fumio
  • Bioscience, Biotechnology, and Biochemistry, Vol. 61, Issue 9
  • DOI: 10.1271/bbb.61.1434

Studies on the Dehydrogenative Polymerizations of Monolignol β‐Glycosides. Part 1. Syntheses of Monolignol β‐glycosides, ( E )‐Isoconiferin, ( E )‐Isosyringin, and ( E )‐Triandrin
journal, September 2006

  • Takano, Toshiyuki; Tobimatsu, Yuki; Hosoya, Takashi
  • Journal of Wood Chemistry and Technology, Vol. 26, Issue 3
  • DOI: 10.1080/02773810601023305

Chromatographic analysis of salicylic compounds in different species of the genusSalix
journal, November 2007

  • Pobłocka-Olech, Loretta; van Nederkassel, Anne-Marie; Vander Heyden, Yvan
  • Journal of Separation Science, Vol. 30, Issue 17
  • DOI: 10.1002/jssc.200700137

Cell-wall polysaccharides in growing poplar bark tissue
journal, January 1995

  • Viëtor, R. J.; Renard, C. M. G. C.; Goldberg, R.
  • International Journal of Biological Macromolecules, Vol. 17, Issue 6
  • DOI: 10.1016/0141-8130(96)81843-5

Chemical and biological characterization of polysaccharides from the bark of Avicennia marina
journal, February 2015

  • Fang, Xubo; Yin, Xiaoxiong; Yuan, Gaofeng
  • European Food Research and Technology, Vol. 241, Issue 1
  • DOI: 10.1007/s00217-015-2430-1

Conversion of biomass into 5-hydroxymethylfurfural using solid acid catalyst
journal, February 2011


Determination of Furfural and Hydroxymethylfurfural Formed From Biomass Under Acidic Conditions
journal, November 2009

  • Chi, Congcong; Zhang, Zeng; Chang, Hou-min
  • Journal of Wood Chemistry and Technology, Vol. 29, Issue 4
  • DOI: 10.1080/02773810903096025

Reactions of aromatic structures in brightness reversion of fully-bleached eucalyptus kraft pulps
journal, May 2009

  • Jääskeläinen, Anna-Stiina; Toikka, Katri; Lähdetie, Anni
  • Holzforschung, Vol. 63, Issue 3
  • DOI: 10.1515/HF.2009.047

Humin based by-products from biomass processing as a potential carbonaceous source for synthesis gas production
journal, January 2015

  • Hoang, T. M. C.; van Eck, E. R. H.; Bula, W. P.
  • Green Chemistry, Vol. 17, Issue 2
  • DOI: 10.1039/C4GC01324G

Raman spectroscopy of polyconjugated molecules and materials: confinement effect in one and two dimensions
journal, September 2004

  • Castiglioni, Chiara; Tommasini, Matteo; Zerbi, Giuseppe
  • Philosophical Transactions of the Royal Society of London. Series A: Mathematical, Physical and Engineering Sciences, Vol. 362, Issue 1824
  • DOI: 10.1098/rsta.2004.1448

Formation, Molecular Structure, and Morphology of Humins in Biomass Conversion: Influence of Feedstock and Processing Conditions
journal, July 2013

  • van Zandvoort, Ilona; Wang, Yuehu; Rasrendra, Carolus B.
  • ChemSusChem, Vol. 6, Issue 9
  • DOI: 10.1002/cssc.201300332

Structural characterization of 13 C-enriched humins and alkali-treated 13 C humins by 2D solid-state NMR
journal, January 2015

  • van Zandvoort, Ilona; Koers, Eline J.; Weingarth, Markus
  • Green Chemistry, Vol. 17, Issue 8
  • DOI: 10.1039/C5GC00327J

Recovery, concentration and purification of phenolic compounds by adsorption: A review
journal, July 2011


Techniques for extraction of bioactive compounds from plant materials: A review
journal, August 2013


Works referencing / citing this record:

The Health-Promoting Potential of Salix spp. Bark Polar Extracts: Key Insights on Phenolic Composition and In Vitro Bioactivity and Biocompatibility
journal, November 2019

  • Ramos, Patrícia A. B.; Moreirinha, Catarina; Silva, Sara
  • Antioxidants, Vol. 8, Issue 12
  • DOI: 10.3390/antiox8120609

Biomordanting willow bark dye on cellulosic materials
journal, December 2019

  • Lohtander, Tia; Arola, Suvi; Laaksonen, Päivi
  • Coloration Technology, Vol. 136, Issue 1
  • DOI: 10.1111/cote.12442

Biomass Recalcitrance in Willow Under Two Biological Conversion Paradigms: Enzymatic Hydrolysis and Anaerobic Digestion
journal, December 2019


Phytochemicals in bioenergy crops
journal, June 2019


The Health-Promoting Potential of Salix spp. Bark Polar Extracts: Key Insights on Phenolic Composition and In Vitro Bioactivity and Biocompatibility
journal, November 2019

  • Ramos, Patrícia A. B.; Moreirinha, Catarina; Silva, Sara
  • Antioxidants, Vol. 8, Issue 12
  • DOI: 10.3390/antiox8120609