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:
-
- Aalto Univ. (Finland)
- Åbo Akademi Univ., Turku (Finland)
- Univ. of Wisconsin, Madison, WI (United States)
- 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}
}
Web of Science
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
Platform biochemicals for a biorenewable chemical industry
journal, May 2008
- Nikolau, Basil J.; Perera, M. Ann D. N.; Brachova, Libuse
- The Plant Journal, Vol. 54, Issue 4
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
The development of short-rotation willow in the northeastern United States for bioenergy and bioproducts, agroforestry and phytoremediation
journal, August 2006
- Volk, T.; Abrahamson, L.; Nowak, C.
- Biomass and Bioenergy, Vol. 30, Issue 8-9
Willow biomass obtained from different soils as a feedstock for energy
journal, November 2015
- Krzyżaniak, Michał; Stolarski, Mariusz J.; Szczukowski, Stefan
- Industrial Crops and Products, Vol. 75
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
High value triterpenic compounds from the outer barks of several Eucalyptus species cultivated in Brazil and in Portugal
journal, January 2011
- Domingues, R. M. A.; Sousa, G. D. A.; Silva, C. M.
- Industrial Crops and Products, Vol. 33, Issue 1
Valorisation of softwood bark through extraction of utilizable chemicals. A review
journal, November 2017
- Jablonsky, M.; Nosalova, J.; Sladkova, A.
- Biotechnology Advances, Vol. 35, Issue 6
Spruce bark as an industrial source of condensed tannins and non-cellulosic sugars
journal, January 2014
- Kemppainen, K.; Siika-aho, M.; Pattathil, S.
- Industrial Crops and Products, Vol. 52
Characterization of condensed tannins and carbohydrates in hot water bark extracts of European softwood species
journal, December 2015
- Bianchi, Sauro; Kroslakova, Ivana; Janzon, Ron
- Phytochemistry, Vol. 120
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
Pressurized hot water extraction (PHWE)
journal, April 2010
- Teo, Chin Chye; Tan, Swee Ngin; Yong, Jean Wan Hong
- Journal of Chromatography A, Vol. 1217, Issue 16
Pressurized hot water flow-through extraction of birch sawdust – Effects of sawdust density and sawdust size
journal, December 2014
- Kilpeläinen, Petri; Kitunen, Veikko; Ilvesniemi, Hannu
- Nordic Pulp & Paper Research Journal, Vol. 29, Issue 4
Comparison of the Chemical Composition of Extracts from Scutellaria lateriflora Using Accelerated Solvent Extraction and Supercritical Fluid Extraction versus Standard Hot Water or 70% Ethanol Extraction
journal, March 2005
- Bergeron, Chantal; Gafner, Stefan; Clausen, Edgar
- Journal of Agricultural and Food Chemistry, Vol. 53, Issue 8
Sustainable Films and Coatings from Hemicelluloses: A Review
journal, May 2008
- Hansen, Natanya M. L.; Plackett, David
- Biomacromolecules, Vol. 9, Issue 6
Hemicelluloses for fuel ethanol: A review
journal, July 2010
- Gírio, F. M.; Fonseca, C.; Carvalheiro, F.
- Bioresource Technology, Vol. 101, Issue 13
Bark salicylates and condensed tannins reduce vole browsing amongst cultivated dark-leaved willows (Salix myrsinifolia)
journal, September 2007
- Heiska, Susanne; Tikkanen, Olli-Pekka; Rousi, Matti
- Chemoecology, Vol. 17, Issue 4
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
Medicinal potential of willow: A chemical perspective of aspirin discovery
journal, July 2010
- Mahdi, Jassem G.
- Journal of Saudi Chemical Society, Vol. 14, Issue 3
Comprehensive analysis of commercial willow bark extracts by new technology platform: Combined use of metabolomics, high-performance liquid chromatography–solid-phase extraction–nuclear magnetic resonance spectroscopy and high-resolution radical scavenging assay
journal, November 2012
- Agnolet, Sara; Wiese, Stefanie; Verpoorte, Robert
- Journal of Chromatography A, Vol. 1262
Treatment of low back pain exacerbations with willow bark extract: a randomized double-blind study
journal, July 2000
- Chrubasik, Sigrun; Eisenberg, Elon; Balan, Edith
- The American Journal of Medicine, Vol. 109, Issue 1
Phenylpropanoids as the biologically active compounds of the medicinal plants and phytopharmaceuticals
journal, January 2013
- Kurkin, Vladimir A.
- Advances in Biological Chemistry, Vol. 03, Issue 01
Isolation, identification and antioxidative capacity of water-soluble phenylpropanoid compounds from Rhodiola crenulata
journal, October 2012
- Chen, Danjun; Fan, Junting; Wang, Peng
- Food Chemistry, Vol. 134, Issue 4
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
Analysis of Phenolic and Cyclic Compounds in Plants Using Derivatization Techniques in Combination with GC-MS-Based Metabolite Profiling
journal, February 2015
- Rohloff, Jens
- Molecules, Vol. 20, Issue 2
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
Preparative biosynthesis of natural glucosides and fluorogenic substrates for β-glucosidases followed by in vivo 13C NMR with high density plant cell cultures
journal, January 1996
- Schroeder, Cornelia; Lutterbach, Ralf; Stöckigt, Joachim
- Tetrahedron, Vol. 52, Issue 3
Two new phenolic water-soluble constituents from branch bark of Davidia involucrata
journal, April 2008
- Wu, Zu-Jian; Ouyang, Ming-An; Wang, Shi-Bin
- Natural Product Research, Vol. 22, Issue 6
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
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
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
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
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
Conversion of biomass into 5-hydroxymethylfurfural using solid acid catalyst
journal, February 2011
- Yang, Fengli; Liu, Qishun; Bai, Xuefang
- Bioresource Technology, Vol. 102, Issue 3
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
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
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
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
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
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
Recovery, concentration and purification of phenolic compounds by adsorption: A review
journal, July 2011
- Soto, María Luisa; Moure, Andrés; Domínguez, Herminia
- Journal of Food Engineering, Vol. 105, Issue 1
Techniques for extraction of bioactive compounds from plant materials: A review
journal, August 2013
- Azmir, J.; Zaidul, I. S. M.; Rahman, M. M.
- Journal of Food Engineering, Vol. 117, Issue 4
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
Biomordanting willow bark dye on cellulosic materials
journal, December 2019
- Lohtander, Tia; Arola, Suvi; Laaksonen, Päivi
- Coloration Technology, Vol. 136, Issue 1
Biomass Recalcitrance in Willow Under Two Biological Conversion Paradigms: Enzymatic Hydrolysis and Anaerobic Digestion
journal, December 2019
- Ohlsson, Jonas A.; Harman-Ware, Anne E.; Sandgren, Mats
- BioEnergy Research, Vol. 13, Issue 1
Phytochemicals in bioenergy crops
journal, June 2019
- Oleszek, Marta; Kowalska, Iwona; Oleszek, Wieslaw
- Phytochemistry Reviews, Vol. 18, Issue 3
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