The Generation of Quinones from Lignin and Lignin-Related Compounds

Wozniak, John C.; Dimmel, Donald R.; Malcolm, Earl W.

doi:10.1080/02773818908050312

Cited by 21 publications

(9 citation statements)

References 17 publications

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“…These quinones are generated by the oxidation of phenolic compounds. For example, BQ comes from the oxidation of p-hydroxyphenyl compounds of 4-hydroxybenzoic acid, 4-hydroxybenzyl aldehyde, and 4-hydroxybenzyl alcohol (11); methoxybenzoquinone (MBQ) is produced from guaiacyl compounds of vanillic acid, vanillin, and vanillyl alcohol (12); and 2,6-dimethoxyhydroquinone (DMHQ) is produced from syringic acid, syringaldehyde, and syringyl alcohol (12). Quinones were found to strongly inhibit Saccharomyces cerevisiae.…”

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confidence: 99%

Mechanism of Tolerance to the Lignin-Derived Inhibitor p -Benzoquinone and Metabolic Modification of Biorefinery Fermentation Strains

Zhao

Gao

et al. 2019

Appl Environ Microbiol

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p-Benzoquinone (BQ) is a lignin-derived inhibitor of biorefinery fermentation strains produced during pretreatment of lignocellulose. Unlike the well-studied inhibitors furan aldehydes, weak acids, and phenolics, the inhibitory properties of BQ, the microbial tolerance mechanism, and the detoxification strategy for this inhibitor have not been clearly elucidated. Here, BQ was identified as a by-product generated during acid pretreatment of various lignocellulose feedstocks, including corn stover, wheat straw, rice straw, tobacco stem, sunflower stem, and corncob residue. BQ at 20 to 200 mg/liter severely inhibited the cell growth and fermentability of various bacteria and yeast strains used in biorefinery fermentations. The BQ tolerance of the strains was found to be closely related to their capacity to convert BQ to nontoxic hydroquinone (HQ). To identify the key genes responsible for BQ tolerance, transcription levels of 20 genes potentially involved in the degradation of BQ in Zymomonas mobilis were investigated using real-time quantitative PCR in BQ-treated cells. One oxidoreductase gene, one hydroxylase gene, three reductase genes, and three dehydrogenase genes were found to be responsible for the conversion of BQ to HQ. Overexpression of the five key genes in Z. mobilis (ZMO1696, ZMO1949, ZMO1576, ZMO1984, and ZMO1399) accelerated its cell growth and cellulosic ethanol production in BQ-containing medium and lignocellulose hydrolysates. IMPORTANCE This study advances our understanding of BQ inhibition behavior and the mechanism of microbial tolerance to this inhibitor and identifies the key genes responsible for BQ detoxification. The insights here into BQ toxicity and tolerance provide the basis for future synthetic biology to engineer industrial fermentation strains with enhanced BQ tolerance.

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confidence: 99%

Mechanism of Tolerance to the Lignin-Derived Inhibitor p -Benzoquinone and Metabolic Modification of Biorefinery Fermentation Strains

Zhao

Gao

et al. 2019

Appl Environ Microbiol

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“…Oxidation of lignin and lignin-derived compounds, such as p -hydroxybenzyl alcohols, p -hydroxybenzaldehydes and p -hydroxybenzoic acids, can result in the formation of p -benzoquinones (Sarkanen and Ludwig 1971 ; Saa et al 1986 ). For example, Wozniak et al ( 1989 ) investigated the use of chemical oxidants to generate o -quinones and p -quinones from lignin and lignin model compounds. Oxidation of various lignin samples and of syringyl-type compounds resulted in the formation of DMBQ (Wozniak et al 1989 ).…”

Section: Discussionmentioning

confidence: 99%

“…For example, Wozniak et al ( 1989 ) investigated the use of chemical oxidants to generate o -quinones and p -quinones from lignin and lignin model compounds. Oxidation of various lignin samples and of syringyl-type compounds resulted in the formation of DMBQ (Wozniak et al 1989 ). Pretreatment of lignocellulosic feedstocks under acidic conditions can result in formation of compounds with syringyl units (Martín et al 2002a ; Du et al 2010 ; Mitchell et al 2014 ) that could serve as precursors of DMBQ.…”

Section: Discussionmentioning

confidence: 99%

Identification of benzoquinones in pretreated lignocellulosic feedstocks and inhibitory effects on yeast

2015

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Pretreatment of lignocellulosic biomass under acidic conditions gives rise to by-products that inhibit fermenting microorganisms. An analytical procedure for identification of p-benzoquinone (BQ) and 2,6-dimethoxybenzoquinone (DMBQ) in pretreated biomass was developed, and the inhibitory effects of BQ and DMBQ on the yeast Saccharomyces cerevisiae were assessed. The benzoquinones were analyzed using ultra-high performance liquid chromatography-electrospray ionization-triple quadrupole-mass spectrometry after derivatization with 2,4-dinitrophenylhydrazine. Pretreatment liquids examined with regard to the presence of BQ and DMBQ originated from six different lignocellulosic feedstocks covering agricultural residues, hardwood, and softwood, and were produced through impregnation with sulfuric acid or sulfur dioxide at varying pretreatment temperature (165–204 °C) and residence time (6–20 min). BQ was detected in all six pretreatment liquids in concentrations ranging up to 6 mg/l, while DMBQ was detected in four pretreatment liquids in concentrations ranging up to 0.5 mg/l. The result indicates that benzoquinones are ubiquitous as by-products of acid pretreatment of lignocellulose, regardless of feedstock and pretreatment conditions. Fermentation experiments with BQ and DMBQ covered the concentration ranges 2 mg/l to 1 g/l and 20 mg/l to 1 g/l, respectively. Even the lowest BQ concentration tested (2 mg/l) was strongly inhibitory to yeast, while 20 mg/l DMBQ gave a slight negative effect on ethanol formation. This work shows that benzoquinones should be regarded as potent and widespread inhibitors in lignocellulosic hydrolysates, and that they warrant attention besides more well-studied inhibitory substances, such as aliphatic carboxylic acids, phenols, and furan aldehydes.

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“…[16][17][18][19][20] They are found in plants, fungi, bacteria, and a few animals and can be synthesized from lignin derived from biomass. [21] Some studies showed that commercial and unmodified lignin, which partially possess quinone structures, are already usable as battery materials. [22,23] Our group has conducted extensive studies on the utilization of quinones as active materials for energy storage devices.…”

Section: Introductionmentioning

confidence: 99%

Quinone‐Based Redox Supercapacitor Using Highly Conductive Hard Carbon Derived from Oak Wood

Katsuyama

Nakayasu

Ōizumi

et al. 2019

Advanced Sustainable Systems

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In this study, the use of biorefined wood materials in the fabrication of organic redox supercapacitors is proposed. Oak‐derived hard carbon (HC) is revealed to have a nanographite domain structure, showing conductivity as high as that of artificial graphite. The CO2‐activated hard carbon (A–HC) has a conductivity one order higher than that of commercial activated carbon, with a surface area of 1126 m2 g−1. The energy densities of supercapacitors composed of a tetrachlorohydroquinone cathode and anthraquinone (AQ) or 1,5‐dichloroanthraquinone (DCAQ) anode are 19.0 and 13.8 Wh kg−1, respectively. The utilization rate of AQ with A–HC is 97.6% (250.9 mAh g−1), which is much higher than those in previous reports (≈80%). After 1000 cycles, 91.0% of the discharge capacity is retained when the DCAQ anode is used. Biorefined wood materials lead to a remarkable improvement in the operation of organic supercapacitors. This is intriguing, because the functional carbon material herein is easily prepared from a natural resource, wood, whereas numerous studies have prepared such materials from artificial chemical sources. Therefore, the use of oak‐derived HC enhances the usability of organic active materials for energy storage devices and potentially has a far‐reaching impact on the environment.

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The Generation of Quinones from Lignin and Lignin-Related Compounds

Cited by 21 publications

References 17 publications

Mechanism of Tolerance to the Lignin-Derived Inhibitor p -Benzoquinone and Metabolic Modification of Biorefinery Fermentation Strains

Mechanism of Tolerance to the Lignin-Derived Inhibitor p -Benzoquinone and Metabolic Modification of Biorefinery Fermentation Strains

Identification of benzoquinones in pretreated lignocellulosic feedstocks and inhibitory effects on yeast

Quinone‐Based Redox Supercapacitor Using Highly Conductive Hard Carbon Derived from Oak Wood

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