Antimicrobial Properties of Corn Stover Lignin Fractions Derived from Catalytic Transfer Hydrogenolysis in Supercritical Ethanol with a Ru/C Catalyst

Kalinoski, Ryan M.; Li, Wenqi; Mobley, Justin K.; Asare, Shardrack O.; Dorrani, Masoumeh; Lynn, Bert C.; Chen, Xiaowen; Shi, Jian

doi:10.1021/acssuschemeng.0c05812

Title: Antimicrobial Properties of Corn Stover Lignin Fractions Derived from Catalytic Transfer Hydrogenolysis in Supercritical Ethanol with a Ru/C Catalyst

Journal Article · Fri Dec 04 00:00:00 EST 2020 · ACS Sustainable Chemistry & Engineering

DOI:https://doi.org/10.1021/acssuschemeng.0c05812· OSTI ID:1760677

Kalinoski, Ryan M. ^[1];

^[1];

^[1]; Asare, Shardrack O. ^[1]; Dorrani, Masoumeh ^[1];

^[1];

^[2];

^[1]

Univ. of Kentucky, Lexington, KY (United States)
National Renewable Energy Lab. (NREL), Golden, CO (United States)

Converting lignin to value-added products at high yields provides an avenue for making ethanol biorefineries more profitable while reducing the carbon footprint of products generally derived from petroleum. In this study, corn stover lignin was depolymerized by catalytic transfer hydrogenolysis (CTH) in supercritical ethanol with a Ru/C catalyst. The lignin-derived bio-oil was then sequentially extracted utilizing hexane, petroleum ether, chloroform, and ethyl acetate as solvents in order of less polar to polar, and the subsequent bio-oils were characterized using GPC, GC/MS, and HSQC NMR. In this work, results show that the monomers in the bio-oil fractions contained primarily alkylated phenols, hydrogenated hydroxycinnamic acid derivatives, syringol and guaiacol-type lignins created from reductive cleavages of ether linkages, which were sequentially extracted into groups depending on the solvent polarity. The antimicrobial properties of the bio-oils were screened against Gram-positive (Bacillus subtilis, Lactobacillus amylovorus, and Staphylococcus epidermidis) and Gram-negative (Escherichia coli) bacteria and yeast (Saccharomyces cerevisiae) by examining microbial growth inhibition. Results show that CTH-derived bio-oils inhibited all tested organisms at concentrations less than 3 mg/mL. Total monomer concentration and the presence of specific monomers (i.e., syringyl propane) showed correlations to antimicrobial activity, likely due to cell death or membrane damage. This study provides insights into using sequential extraction to fractionate lignin-derived compounds and correlations between the properties of the extracted compounds and their antimicrobial activity.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: National Renewable Energy Lab. (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Bioenergy Technologies Office; National Science Foundation (NSF); National Institute of Food and Agriculture (NIFA); USDA

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 1760677

Report Number(s):: NREL/JA-5100-77631; MainId:29557; UUID:615063a0-44c3-4c5d-94d5-6fd725b201af; MainAdminID:19142

Journal Information:: ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 50; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (62)

Selective separation of aromatic hydrocarbons through supported liquid membranes based on ionic liquids Matsumoto, Michiaki; Inomoto, Yasushi; Kondo, Kazuo Journal of Membrane Science, Vol. 246, Issue 1 https://doi.org/10.1016/j.memsci.2004.08.013	journal	January 2005
Hydrothermal degradation of alkali lignin to bio-phenolic compounds in sub/supercritical ethanol and water–ethanol co-solvent Cheng, Shuna; Wilks, Carolynne; Yuan, Zhongshun Polymer Degradation and Stability, Vol. 97, Issue 6 https://doi.org/10.1016/j.polymdegradstab.2012.03.044	journal	June 2012
Recovery of renewable phenolic fraction from pyrolysis oil Fele Žilnik, Ljudmila; Jazbinšek, Alma Separation and Purification Technology, Vol. 86 https://doi.org/10.1016/j.seppur.2011.10.040	journal	February 2012
Bright Side of Lignin Depolymerization: Toward New Platform Chemicals Sun, Zhuohua; Fridrich, Bálint; de Santi, Alessandra Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00588	journal	January 2018
Catalytic Depolymerization of Lignin in Supercritical Ethanol Huang, Xiaoming; Korányi, Tamás I.; Boot, Michael D. ChemSusChem, Vol. 7, Issue 8 https://doi.org/10.1002/cssc.201402094	journal	May 2014
Sequential Extraction and Characterization of Lignin-Derived Compounds from Thermochemically Processed Biorefinery Lignins Dodge, Luke A.; Kalinoski, Ryan M.; Das, Lalitendu Energy & Fuels, Vol. 33, Issue 5 https://doi.org/10.1021/acs.energyfuels.9b00376	journal	March 2019
Liquid–Liquid Extraction of Biomass Pyrolysis Bio-oil Wei, Yi; Lei, Hanwu; Wang, Lu Energy & Fuels, Vol. 28, Issue 2 https://doi.org/10.1021/ef402490s	journal	February 2014
Lignin Depolymerization and Conversion A Review of Thermochemical Methods Pandey, M. P.; Kim, C. S. Chemical Engineering & Technology, Vol. 34, Issue 1, p. 29-41 https://doi.org/10.1002/ceat.201000270	journal	November 2010
Antimicrobial and Antiradical Activity of Extracts Obtained from Leaves of Five Species of the Genus Bergenia: Identification of Antimicrobial Compounds Żbikowska, Beata; Franiczek, Roman; Sowa, Alina Microbial Drug Resistance, Vol. 23, Issue 6 https://doi.org/10.1089/mdr.2016.0251	journal	September 2017
Separation of phthalate esters from bio-oil derived from rice husk by a basification–acidification process and column chromatography Zeng, Fanxin; Liu, Wujun; Jiang, Hong Bioresource Technology, Vol. 102, Issue 2 https://doi.org/10.1016/j.biortech.2010.09.024	journal	January 2011
Selective production of 4-ethylphenolics from lignin via mild hydrogenolysis Ye, Yueyuan; Zhang, Yu; Fan, Juan Bioresource Technology, Vol. 118 https://doi.org/10.1016/j.biortech.2012.05.127	journal	August 2012
Bamboo biochar-catalytic degradation of lignin under microwave heating Tayier, Maimaitiaili; Zhao, Yunfeng; Duan, Dengle Journal of Wood Chemistry and Technology, Vol. 40, Issue 3 https://doi.org/10.1080/02773813.2020.1741643	journal	March 2020
Lignin depolymerization over Ni/C catalyst in methanol, a continuation: effect of substrate and catalyst loading Klein, Ian; Saha, Basudeb; Abu-Omar, Mahdi M. Catalysis Science & Technology, Vol. 5, Issue 6 https://doi.org/10.1039/C5CY00490J	journal	January 2015
Study on Solvent Extraction of Fast Pyrolysis Bio-Oil Tian, Qi Kui; He, Liang; Zhang, Hang Advanced Materials Research, Vol. 306-307 https://doi.org/10.4028/www.scientific.net/AMR.306-307.1532	journal	August 2011
Peroxidase-dependent cross-linking reactions of p-hydroxycinnamates in plant cell walls Ralph, John; Bunzel, Mirko; Marita, Jane M. Phytochemistry Reviews, Vol. 3, Issue 1-2, p. 79-96 https://doi.org/10.1023/B:PHYT.0000047811.13837.fb	journal	January 2004
High-Efficiency Liquid Chromatographic Separation Utilizing Long Monolithic Silica Capillary Columns Miyamoto, Kosuke; Hara, Takeshi; Kobayashi, Hiroshi Analytical Chemistry, Vol. 80, Issue 22 https://doi.org/10.1021/ac801042c	journal	November 2008
Naturally Occurring Phenolic Antibacterial Compounds Show Effectiveness against Oral Bacteria by a Quantitative Structure−Activity Relationship Study Greenberg, Michael; Dodds, Michael; Tian, Minmin Journal of Agricultural and Food Chemistry, Vol. 56, Issue 23 https://doi.org/10.1021/jf8020859	journal	December 2008
Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process Song, Qi; Wang, Feng; Cai, Jiaying Energy & Environmental Science, Vol. 6, Issue 3, p. 994-1007 https://doi.org/10.1039/c2ee23741e	journal	January 2013
Recent Efforts to Prevent Undesirable Reactions From Fractionation to Depolymerization of Lignin: Toward Maximizing the Value From Lignin Kim, Kwang Ho; Kim, Chang Soo Frontiers in Energy Research, Vol. 6 https://doi.org/10.3389/fenrg.2018.00092	journal	September 2018
Hydro- and solvothermolysis of kraft lignin for maximizing production of monomeric aromatic chemicals Lee, Hong-shik; Jae, Jungho; Ha, Jeong-Myeong Bioresource Technology, Vol. 203 https://doi.org/10.1016/j.biortech.2015.12.022	journal	March 2016
Ionophore resistance of ruminal bacteria and its potential impact on human health Russell, James B.; Houlihan, Adam J. FEMS Microbiology Reviews, Vol. 27, Issue 1 https://doi.org/10.1016/S0168-6445(03)00019-6	journal	April 2003
Antioxidant, antimicrobial, and antimutagenic properties of technical lignins and their applications Espinoza-Acosta, José Luis; Torres-Chávez, Patricia Isabel; Ramírez-Wong, Benjamín BioResources, Vol. 11, Issue 2 https://doi.org/10.15376/biores.11.2.Espinoza_Acosta	journal	February 2016
Effects of Sugars, Furans, and their Derivatives on Hydrodeoxygenation of Biorefinery Lignin‐Rich Wastes to Hydrocarbons Wang, Hongliang; Duan, Yuhua; Zhang, Qian ChemSusChem, Vol. 11, Issue 15 https://doi.org/10.1002/cssc.201801401	journal	July 2018
Cell membrane damage induced by phenolic acids on wine lactic acid bacteria Campos, F. M.; Couto, J. A.; Figueiredo, A. R. International Journal of Food Microbiology, Vol. 135, Issue 2 https://doi.org/10.1016/j.ijfoodmicro.2009.07.031	journal	October 2009
Catalytic transfer hydrogenolysis of ionic liquid processed biorefinery lignin to phenolic compounds Kim, Kwang Ho; Simmons, Blake A.; Singh, Seema Green Chemistry, Vol. 19, Issue 1 https://doi.org/10.1039/C6GC02473D	journal	January 2017
Predicting lignin depolymerization yields from quantifiable properties using fractionated biorefinery lignins Phongpreecha, Thanaphong; Hool, Nicholas C.; Stoklosa, Ryan J. Green Chem., Vol. 19, Issue 21 https://doi.org/10.1039/C7GC02023F	journal	January 2017
Lignin-based polyurethane doped with carbon nanotubes for sensor applications: Lignin-based polyurethane doped with carbon nanotubes Faria, Fernando AC; Evtuguin, Dmitry V.; Rudnitskaya, Alisa Polymer International, Vol. 61, Issue 5 https://doi.org/10.1002/pi.4140	journal	January 2012
Catalytic disassembly of an organosolv lignin via hydrogen transfer from supercritical methanol Barta, Katalin; Matson, Theodore D.; Fettig, Makayla L. Green Chemistry, Vol. 12, Issue 9 https://doi.org/10.1039/c0gc00181c	journal	January 2010
Reductive Catalytic Fractionation of Corn Stover Lignin Anderson, Eric M.; Katahira, Rui; Reed, Michelle ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 12 https://doi.org/10.1021/acssuschemeng.6b01858	journal	October 2016
Chemical Composition, Antioxidant, and Antibacterial Activity of Wood Vinegar from Litchi chinensis Yang, Jyh-Ferng; Yang, Cheng-Hong; Liang, Ming-Tsai Molecules, Vol. 21, Issue 9 https://doi.org/10.3390/molecules21091150	journal	August 2016
Acetic Acid Recovery from Fast Pyrolysis Oil. An Exploratory Study on Liquid-Liquid Reactive Extraction using Aliphatic Tertiary Amines Mahfud, F. H.; van Geel, F. P.; Venderbosch, R. H. Separation Science and Technology, Vol. 43, Issue 11-12 https://doi.org/10.1080/01496390802222509	journal	August 2008
Characterization and Catalytic Transfer Hydrogenolysis of Deep Eutectic Solvent Extracted Sorghum Lignin to Phenolic Compounds Das, Lalitendu; Li, Mi; Stevens, Joseph ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 8 https://doi.org/10.1021/acssuschemeng.8b01763	journal	June 2018
Lipid Production from Dilute Alkali Corn Stover Lignin by Rhodococcus Strains He, Yucai; Li, Xiaolu; Ben, Haoxi ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 3 https://doi.org/10.1021/acssuschemeng.6b02627	journal	January 2017
Techno-economic analysis for incorporating a liquid-liquid extraction system to remove acetic acid into a proposed commercial scale biorefinery Aghazadeh, Mahdieh; Engelberth, Abigail S. Biotechnology Progress, Vol. 32, Issue 4 https://doi.org/10.1002/btpr.2325	journal	July 2016
Staphylococcus epidermidis biofilms: importance and implications O'Gara, James P.; Humphreys, Hilary Journal of Medical Microbiology, Vol. 50, Issue 7 https://doi.org/10.1099/0022-1317-50-7-582	journal	July 2001
Understanding Low-Pressure Hydropyrolysis of Lignin Using Deuterated Sodium Formate Li, Wenqi; Zhou, Shuai; Xue, Yuan ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 10 https://doi.org/10.1021/acssuschemeng.7b01748	journal	August 2017
Base-Catalyzed Depolymerization of Biorefinery Lignins Katahira, Rui; Mittal, Ashutosh; McKinney, Kellene ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 3 https://doi.org/10.1021/acssuschemeng.5b01451	journal	December 2015
Polyether ionophores: broad-spectrum and promising biologically active molecules for the control of drug-resistant bacteria and parasites Kevin II, Dion A.; Meujo, Damaris AF; Hamann, Mark T. Expert Opinion on Drug Discovery, Vol. 4, Issue 2 https://doi.org/10.1517/17460440802661443	journal	February 2009
High-yield and high-calorific bio-oil production from concentrated sulfuric acid hydrolysis lignin in supercritical ethanol Riaz, Asim; Kim, Chang Soo; Kim, Yunje Fuel, Vol. 172 https://doi.org/10.1016/j.fuel.2015.12.051	journal	May 2016
Catalytic Hydrogenolysis of Aryl Ethers: A Key Step in Lignin Valorization to Valuable Chemicals Zaheer, Muhammad; Kempe, Rhett ACS Catalysis, Vol. 5, Issue 3 https://doi.org/10.1021/cs501498f	journal	February 2015
Catalytic in Situ Hydrogenolysis of Lignin in Supercritical Ethanol: Effect of Phenol, Catalysts, and Reaction Temperature Zhou, Minghao; Sharma, Brajendra K.; Liu, Peng ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 5 https://doi.org/10.1021/acssuschemeng.8b00701	journal	March 2018
Antibacterial and antifungal activities of pyroligneous acid from wood of Eucalyptus urograndis and Mimosa tenuiflora de Souza Araújo, E.; Pimenta, A. S.; Feijó, F. M. C. Journal of Applied Microbiology, Vol. 124, Issue 1 https://doi.org/10.1111/jam.13626	journal	December 2017
Lignin pyrolysis reactions Kawamoto, Haruo Journal of Wood Science, Vol. 63, Issue 2 https://doi.org/10.1007/s10086-016-1606-z	journal	January 2017
Effect of solvent evaporation method on phenolic compounds and the antioxidant activity of Moringa oleifera cultivated in Southern Tunisia Bennour, N.; Mighri, H.; Eljani, H. South African Journal of Botany, Vol. 129 https://doi.org/10.1016/j.sajb.2019.05.005	journal	March 2020
Mode of antimicrobial action of vanillin against Escherichia coli, Lactobacillus plantarum and Listeria innocua Fitzgerald, D. J.; Stratford, M.; Gasson, M. J. Journal of Applied Microbiology, Vol. 97, Issue 1 https://doi.org/10.1111/j.1365-2672.2004.02275.x	journal	July 2004
Antimicrobial Activity of Vanillin against Spoilage Microorganisms in Stored Fresh-Cut Mangoes Ngarmsak, Manatchaya; Delaquis, Pascal; Toivonen, Peter Journal of Food Protection, Vol. 69, Issue 7 https://doi.org/10.4315/0362-028X-69.7.1724	journal	July 2006
Matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry analysis for characterization of lignin oligomers using cationization techniques and 2,5‐dihydroxyacetophenone (DHAP) matrix Bowman, Amber S.; Asare, Shardrack O.; Lynn, Bert C. Rapid Communications in Mass Spectrometry, Vol. 33, Issue 8 https://doi.org/10.1002/rcm.8406	journal	March 2019
Storage Effect on Phenols and on the Antioxidant Activity of Extracts from Anemopsis californica and Inhibition of Elastase Enzyme Del-Toro-Sánchez, Carmen Lizette; Gutiérrez-Lomelí, Melesio; Lugo-Cervantes, Eugenia Journal of Chemistry, Vol. 2015 https://doi.org/10.1155/2015/602136	journal	January 2015
Antibiotic properties of lignin components Zemek, J.; Košíková, B.; Augustín, J. Folia Microbiologica, Vol. 24, Issue 6 https://doi.org/10.1007/BF02927180	journal	December 1979
Techno‐economic analysis of jet‐fuel production from biorefinery waste lignin Shen, Rongchun; Tao, Ling; Yang, Bin Biofuels, Bioproducts and Biorefining, Vol. 13, Issue 3 https://doi.org/10.1002/bbb.1952	journal	December 2018
Recent Advances in Characterization of Lignin Polymer by Solution-State Nuclear Magnetic Resonance (NMR) Methodology Wen, Jia-Long; Sun, Shao-Long; Xue, Bai-Liang Materials, Vol. 6, Issue 1 https://doi.org/10.3390/ma6010359	journal	January 2013
Phenolic Compounds in Antimicrobial Therapy Mandal, Santi M.; Dias, Renata O.; Franco, Octavio L. Journal of Medicinal Food, Vol. 20, Issue 10 https://doi.org/10.1089/jmf.2017.0017	journal	October 2017
Ethanol as capping agent and formaldehyde scavenger for efficient depolymerization of lignin to aromatics Huang, Xiaoming; Korányi, Tamás I.; Boot, Michael D. Green Chemistry, Vol. 17, Issue 11 https://doi.org/10.1039/C5GC01120E	journal	January 2015
Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization Shuai, Li; Amiri, Masoud Talebi; Questell-Santiago, Ydna M. Science, Vol. 354, Issue 6310 https://doi.org/10.1126/science.aaf7810	journal	October 2016
Preventing Lignin Condensation to Facilitate Aromatic Monomer Production Lan, Wu; Luterbacher, Jeremy S. CHIMIA International Journal for Chemistry, Vol. 73, Issue 7 https://doi.org/10.2533/chimia.2019.591	journal	August 2019
Separation of chemical groups from bio-oil water-extract via sequential organic solvent extraction Ren, Shoujie; Ye, X. Philip; Borole, Abhijeet P. Journal of Analytical and Applied Pyrolysis, Vol. 123 https://doi.org/10.1016/j.jaap.2017.01.004	journal	January 2017
Spores of Bacillus subtilis: their resistance to and killing by radiation, heat and chemicals Setlow, P. Journal of Applied Microbiology, Vol. 101, Issue 3 https://doi.org/10.1111/j.1365-2672.2005.02736.x	journal	September 2006
Catalytic transfer hydrogenolysis as an efficient route in cleavage of lignin and model compounds Zhang, Jiaguang Green Energy & Environment, Vol. 3, Issue 4 https://doi.org/10.1016/j.gee.2018.08.001	journal	October 2018
Peracetic Acid Depolymerization of Biorefinery Lignin for Production of Selective Monomeric Phenolic Compounds Ma, Ruoshui; Guo, Mond; Lin, Kuan-ting Chemistry - A European Journal, Vol. 22, Issue 31 https://doi.org/10.1002/chem.201600546	journal	July 2016
Antibacterial Activity and Membrane-Disruptive Mechanism of 3-p-trans-Coumaroyl-2-hydroxyquinic Acid, a Novel Phenolic Compound from Pine Needles of Cedrus deodara, against Staphylococcus aureus Wu, Yanping; Bai, Jinrong; Zhong, Kai Molecules, Vol. 21, Issue 8 https://doi.org/10.3390/molecules21081084	journal	August 2016
Towards high-yield lignin monomer production Shuai, Li; Saha, Basudeb Green Chemistry, Vol. 19, Issue 16 https://doi.org/10.1039/C7GC01676J	journal	January 2017
Modeling bacterial contamination of fuel ethanol fermentation Bischoff, Kenneth M.; Liu, Siqing; Leathers, Timothy D. Biotechnology and Bioengineering, Vol. 103, Issue 1 https://doi.org/10.1002/bit.22244	journal	May 2009

Similar Records

Reductive Catalytic Fractionation of Corn Stover Lignin

Journal Article · Sat Sep 03 00:00:00 EDT 2016 · ACS Sustainable Chemistry & Engineering · OSTI ID:1760677

Anderson, Eric M.; Katahira, Rui; Reed, Michelle; +4 more

Diol pretreatment to fractionate a reactive lignin in lignocellulosic biomass biorefineries

Journal Article · Wed Apr 24 00:00:00 EDT 2019 · Green Chemistry · OSTI ID:1760677

Dong, Chengyu; Meng, Xianzhi; Yeung, Chi Shun; +3 more

Low temperature hydrogenation of pyrolytic lignin over Ru/TiO₂: 2D HSQC and ¹³C NMR study of reactants and products

Journal Article · Thu Oct 15 00:00:00 EDT 2015 · Green Chemistry · OSTI ID:1760677

Chen, Wen; McClelland, Daniel J.; Azarpira, Ali; +3 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Ru/C catalyst
DMR
jet fuel
lignin upgrading
hydrogenolysis
catalysis
antimicrobial
liquid−liquid extraction
depolymerization

Title: Antimicrobial Properties of Corn Stover Lignin Fractions Derived from Catalytic Transfer Hydrogenolysis in Supercritical Ethanol with a Ru/C Catalyst

Citation Formats

References (62)

Similar Records

Related Subjects