Volume 9 Issue 2
May  2024
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Yufeng Yuan, Xinyu Guo, Bo Jiang, Wenjuan Wu, Tingwei Zhang, Michael Sweeney, Mehraj Ahmad, Yongcan Jin. Effect of various aromatic compounds with different functional groups on enzymatic hydrolysis of microcrystalline cellulose and alkaline pretreated wheat straw[J]. Journal of Bioresources and Bioproducts, 2024, 9(2): 211-221. doi: 10.1016/j.jobab.2023.12.006
Citation: Yufeng Yuan, Xinyu Guo, Bo Jiang, Wenjuan Wu, Tingwei Zhang, Michael Sweeney, Mehraj Ahmad, Yongcan Jin. Effect of various aromatic compounds with different functional groups on enzymatic hydrolysis of microcrystalline cellulose and alkaline pretreated wheat straw[J]. Journal of Bioresources and Bioproducts, 2024, 9(2): 211-221. doi: 10.1016/j.jobab.2023.12.006

Effect of various aromatic compounds with different functional groups on enzymatic hydrolysis of microcrystalline cellulose and alkaline pretreated wheat straw

doi: 10.1016/j.jobab.2023.12.006
Funds:

No. 21704045) and Jiangsu Provincial Key Research and Development Program, China (No. BE2021368) for supporting the work.

Authors are thankful to National Natural Science Foundation of China (No. 31730106

  • Publish Date: 2023-12-26
  • Low molecular aromatic compounds are detrimental to the enzymatic hydrolysis of lignocellulose. However, the specific role of their functional groups remains unclear. Here, a series of nine aromatic compounds as additives were tested to understand their effect on the hydrolysis yield of microcrystalline cellulose (MCC) and alkaline pretreated wheat straw. Based on the results, the inhibition of aldehyde groups on MCC was greater than that of carboxyl groups, whereas for the alkaline pretreated wheat straw case, the inhibitory effect of aldehyde groups was lower than that of carboxyl groups. Increased methoxyl groups of aromatic compounds reduced the inhibitory effect on enzymatic hydrolysis of both substrates. Stronger inhibition of aromatic compounds on MCC hydrolysis was detected in comparison with the alkaline pretreated wheat straw, indicating that the substrate lignin can offset the inhibition to a certain extent. Among all aromatic compounds, syringaldehyde with one aldehyde group and two methoxyl groups improved the glucan conversion of the alkaline pretreated wheat straw.

     

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  • [1]
    Akimkulova, A., Zhou, Y., Zhao, X.B., Liu, D.H., 2016. Improving the enzymatic hydrolysis of dilute acid pretreated wheat straw by metal ion blocking of non-productive cellulase adsorption on lignin. Bioresour. Technol. 208, 110-116.
    [2]
    Banu Jamaldheen, S., Kurade, M.B., Basak, B., Yoo, C.G., Oh, K.K., Jeon, B.H., Kim, T.H., 2022. A review on physico-chemical delignification as a pretreatment of lignocellulosic biomass for enhanced bioconversion. Bioresour. Technol. 346, 126591.
    [3]
    Boukari, I., O'Donohue, M., Rémond, C., Chabbert, B., 2011. Probing a family GH11 endo-β-1, 4-xylanase inhibition mechanism by phenolic compounds: role of functional phenolic groups. J. Mol. Catal. B Enzym. 72, 130-138.
    [4]
    Chen, H., Mao, J.Y., Jiang, B., Wu, W.J., Jin, Y.C., 2021. Carbonate-oxygen pretreatment of waste wheat straw for enhancing enzymatic saccharification. Process. Biochem. 104, 117-123.
    [5]
    Chen, X.X., Zhai, R., Li, Y., Yuan, X.C., Liu, Z.H., Jin, M.J., 2020. Understanding the structural characteristics of water-soluble phenolic compounds from four pretreatments of corn stover and their inhibitory effects on enzymatic hydrolysis and fermentation. Biotechnol. Biofuels 13, 44.
    [6]
    Du, B.W., Sharma, L.N., Becker, C., Chen, S.F., Mowery, R.A., van Walsum, G.P., Chambliss, C.K., 2010. Effect of varying feedstock-pretreatment chemistry combinations on the formation and accumulation of potentially inhibitory degradation products in biomass hydrolysates. Biotechnol. Bioeng. 107, 430-440.
    [7]
    Fan, M.S., Lei, M., Xie, J., Zhang, H.D., 2022. Further insights into the solubilization and surface modification of lignin on enzymatic hydrolysis and ethanol production. Renew. Energy 186, 646-655.
    [8]
    Ghose, T.K., 1987. Measurement of cellulase activities. Pure Appl. Chem. 59, 257-268.
    [9]
    Gillet, S., Aguedo, M., Petitjean, L., Morais, A.R.C., da Costa Lopes, A.M., Łukasik, R.M., Anastas, P.T., 2017. Lignin transformations for high value applications: towards targeted modifications using green chemistry. Green Chem. 19, 4200-4233.
    [10]
    Haldar, D., Purkait, M.K., 2020. Lignocellulosic conversion into value-added products: a review. Process. Biochem. 89, 110-133.
    [11]
    Huang, C.X., He, J., Min, D.Y., Lai, C.H., Yong, Q., 2016. Understanding the nonproductive enzyme adsorption and physicochemical properties of residual lignins in moso bamboo pretreated with sulfuric acid and kraft pulping. Appl. Biochem. Biotechnol. 180, 1508-1523.
    [12]
    Jiang, X.X., Zhai, R., Leng, Y., Deng, Q.F., Jin, M.J., 2022. Understanding the toxicity of lignin-derived phenolics towards enzymatic saccharification of lignocellulose for rationally developing effective in situ mitigation strategies to maximize sugar production from lignocellulosic biorefinery. Bioresour. Technol. 349, 126813.
    [13]
    Jing, X.Y., Zhang, X.X., Bao, J., 2009. Inhibition performance of lignocellulose degradation products on industrial cellulase enzymes during cellulose hydrolysis. Appl. Biochem. Biotechnol. 159, 696-707.
    [14]
    Kellock, M., Rahikainen, J., Marjamaa, K., Kruus, K., 2017. Lignin-derived inhibition of monocomponent cellulases and a xylanase in the hydrolysis of lignocellulosics. Bioresour. Technol. 232, 183-191.
    [15]
    Kim, Y., Ximenes, E., Mosier, N.S., Ladisch, M.R., 2011. Soluble inhibitors/deactivators of cellulase enzymes from lignocellulosic biomass. Enzyme Microb. Technol. 48, 408-415.
    [16]
    Kumar, S., Ahluwalia, V., Kundu, P., Sangwan, R.S., Kansal, S.K., Runge, T.M., Elumalai, S., 2018. Improved levulinic acid production from agri-residue biomass in biphasic solvent system through synergistic catalytic effect of acid and products. Bioresour. Technol. 251, 143-150.
    [17]
    Lai, C.H., Yang, C.D., Jia, Y., Xu, X., Wang, K., Yong, Q., 2022. Lignin fractionation to realize the comprehensive elucidation of structure-inhibition relationship of lignins in enzymatic hydrolysis. Bioresour. Technol. 355, 127255.
    [18]
    Li, Y., Qi, B.K., Wan, Y.H., 2014. Inhibitory effect of vanillin on cellulase activity in hydrolysis of cellulosic biomass. Bioresour. Technol. 167, 324-330.
    [19]
    Ling, R.X., Wei, W.Q., Jin, Y.C., 2022. Pretreatment of sugarcane bagasse with acid catalyzed ethylene glycol-water to improve the cellulose enzymatic conversion. Bioresour. Technol. 361, 127723.
    [20]
    Liu, H., Sun, J.L., Leu, S.Y., Chen, S.C., 2016. Toward a fundamental understanding of cellulase-lignin interactions in the whole slurry enzymatic saccharification process. Biofuels Bioprod. Biorefin. 10, 648-663.
    [21]
    Mabee, W.E., Saddler, J.N., 2010. Bioethanol from lignocellulosics: status and perspectives in Canada. Bioresour. Technol. 101, 4806-4813.
    [22]
    Manzanares, P., 2020. The role of biorefinering research in the development of a modern bioeconomy. Acta Innov. 37, 47-56.
    [23]
    Oh, H.I., Hoff, J.E., Armstrong, G.S., Haff, L.A., 1980. Hydrophobic interaction in tannin-protein complexes. J. Agric. Food Chem. 28, 394-398.
    [24]
    Oliveira, D.M., Hoshino, É.P., Mota, T.R., Marchiosi, R., Ferrarese-Filho, O., dos Santos, W.D., 2020. Modulation of cellulase activity by lignin-related compounds. Bioresour. Technol. Rep. 10, 100390.
    [25]
    Orejuela-Escobar, L.M., Landázuri, A.C., Goodell, B., 2021. Second generation biorefining in Ecuador: circular bioeconomy, zero waste technology, environment and sustainable development: the nexus. J. Bioresour. Bioprod. 6, 83-107.
    [26]
    Pan, X.J., 2008. Role of functional groups in lignin inhibition of enzymatic hydrolysis of cellulose to glucose. J. Biobased Mater. Bioenergy 2, 25-32.
    [27]
    Patel, A., Shah, A.R., 2021. Integrated lignocellulosic biorefinery: gateway for production of second generation ethanol and value added products. J. Bioresour. Bioprod. 6, 108-128.
    [28]
    Qin, L., Li, W.C., Liu, L., Zhu, J.Q., Li, X., Li, B.Z., Yuan, Y.J., 2016. Inhibition of lignin-derived phenolic compounds to cellulase. Biotechnol. Biofuels 9, 70.
    [29]
    Sang, S., Zhuang, X.S., Chen, H.Y., Qin, Y.Y., Cao, J.X., Fan, F.L., Lan, T.Q., 2022. Effect of supramolecular structural changes during the crystalline transformation of cellulose on its enzymatic hydrolysis. Ind. Crops Prod. 180, 114687.
    [30]
    Shen, X.J., Meng, Q.L., Mei, Q.Q., Xiang, J.F., Liu, H.Z., Han, B.X., 2020. The production of 4-ethyltoluene via directional valorization of lignin. Green Chem. 22, 2191-2196.
    [31]
    Silveira, M.H.L., Morais, A.R.C., da Costa Lopes, A.M., Olekszyszen, D.N., Bogel-Łukasik, R., Andreaus, J., Pereira Ramos, L., 2015. Current pretreatment technologies for the development of cellulosic ethanol and biorefineries. ChemSusChem 8, 3366-3390.
    [32]
    Sluiter, A., Hames, B., Ruiz, R., Scarlata, C., Sluiter, J., Templeton, D., Crocker, D. 2008. Determination of structural carbohydrates and lignin in biomass. Lab. Anal. Proced., NREL, Report No. TP-510-42618.
    [33]
    Song, Y.L., Chandra, R.P., Zhang, X., Saddler, J.N., 2020. Non-productive celluase binding onto deep eutectic solvent (DES) extracted lignin from willow and corn stover with inhibitory effects on enzymatic hydrolysis of cellulose. Carbohydr. Polym. 250, 116956.
    [34]
    Stamogiannou, I., Van Camp, J., Smagghe, G., Van de Walle, D., Dewettinck, K., Raes, K., 2021. Impact of phenolic compound as activators or inhibitors on the enzymatic hydrolysis of cellulose. Int. J. Biol. Macromol. 186, 174-180.
    [35]
    Tejirian, A., Xu, F., 2011. Inhibition of enzymatic cellulolysis by phenolic compounds. Enzyme Microb. Technol. 48, 239-247.
    [36]
    Tian, Y., Jiang, Y., Ou, S.Y., 2013. Interaction of cellulase with three phenolic acids. Food Chem. 138, 1022-1027.
    [37]
    Vignesh, N., Chandraraj, K., 2021. Improved high solids loading enzymatic hydrolysis and fermentation of cotton microdust by surfactant addition and optimization of pretreatment. Process. Biochem. 106, 60-69.
    [38]
    Ximenes, E., Kim, Y., Mosier, N., Dien, B., Ladisch, M., 2010. Inhibition of cellulases by phenols. Enzyme Microb. Technol. 46, 170-176.
    [39]
    Ximenes, E., Kim, Y., Mosier, N., Dien, B., Ladisch, M., 2011. Deactivation of cellulases by phenols. Enzyme Microb. Technol. 48, 54-60.
    [40]
    Xu, C., Liu, F., Alam, M.A., Chen, H.J., Zhang, Y., Liang, C.Y., Xu, H.J., Huang, S.S., Xu, J.L., Wang, Z.M., 2020. Comparative study on the properties of lignin isolated from different pretreated sugarcane bagasse and its inhibitory effects on enzymatic hydrolysis. Int. J. Biol. Macromol. 146, 132-140.
    [41]
    Yang, Q., Pan, X.J., 2016. Correlation between lignin physicochemical properties and inhibition to enzymatic hydrolysis of cellulose. Biotechnol. Bioeng. 113, 1213-1224.
    [42]
    Yao, F.P., Xu, S.G., Jiang, Z.C., Zhao, J., Hu, C.W., 2022a. The inhibition of p-hydroxyphenyl hydroxyl group in residual lignin on enzymatic hydrolysis of cellulose and its underlying mechanism. Bioresour. Technol. 346, 126585.
    [43]
    Yao, J.H., Li, C.L., Xiao, L., Wu, Y.Y., Wu, Q.W., Cui, Z.F., Wang, B., 2022b. Influence of natural deep eutectic solvents on stability and structure of cellulase. J. Mol. Liq. 346, 118238.
    [44]
    Yoo, C.G., Meng, X.Z., Pu, Y.Q., Ragauskas, A.J., 2020. The critical role of lignin in lignocellulosic biomass conversion and recent pretreatment strategies: a comprehensive review. Bioresour. Technol. 301, 122784.
    [45]
    Zhai, R., Hu, J.G., Saddler, J.J.N., 2018a. Extent of enzyme inhibition by phenolics derived from pretreated biomass is significantly influenced by the size and carbonyl group content of the phenolics. ACS Sustain. Chem. Eng. 6, 3823-3829.
    [46]
    Zhai, R., Hu, J.G., Saddler, J.N., 2018b. Minimizing cellulase inhibition of whole slurry biomass hydrolysis through the addition of carbocation scavengers during acid-catalyzed pretreatment. Bioresour. Technol. 258, 12-17.
    [47]
    Zhang, F., Zhang, J., Tong, C.L., Chen, Y.D., Zhuang, S.L., Liu, W.P., 2013. Molecular interactions of benzophenone UV filters with human serum albumin revealed by spectroscopic techniques and molecular modeling. J. Hazard. Mater. 263 Pt 2, 618-626.
    [48]
    Zhang, Q.T., Wan, G.C., Li, M.F., Jiang, H.R., Wang, S.F., Min, D.Y., 2020. Impact of bagasse lignin-carbohydrate complexes structural changes on cellulase adsorption behavior. Int. J. Biol. Macromol. 162, 236-245.
    [49]
    Zhao, J.Y., Chen, H.Z., 2014. Stimulation of cellulases by small phenolic compounds in pretreated stover. J. Agric. Food Chem. 62, 3223-3229.
    [50]
    Zhao, X.X., Huang, C.X., Lin, W.Q., Bian, B., Lai, C.H., Ling, Z., Yong, Q., 2022. A structure-activity understanding of the interaction between lignin and various cellulase domains. Bioresour. Technol. 351, 127042.
    [51]
    Zheng, W.Q., Lan, T.Q., Li, H., Yue, G.J., Zhou, H.F., 2020. Exploring why sodium lignosulfonate influenced enzymatic hydrolysis efficiency of cellulose from the perspective of substrate-enzyme adsorption. Biotechnol. Biofuels 13, 19.
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