Volume 11 Issue 2
May  2026
Turn off MathJax
Article Contents
Article Navigation >  Journal of Bioresources and Bioproducts  > 2026  >  11(2): 100233
Huali Zeng, Linlin Liang, Liuli Zhu, Xianting Zeng, Yanling Bin, Renman Wu, Baojie Liu, Chengrong Qin, Shuangfei Wang, Shuangquan Yao. Mechanistic hydrogen bond mediated screening of hydroxyl functionalized additives for lignin condensation suppression[J]. Journal of Bioresources and Bioproducts, 2026, 11(2): 100233. doi: 10.1016/j.jobab.2026.100233
Citation: Huali Zeng, Linlin Liang, Liuli Zhu, Xianting Zeng, Yanling Bin, Renman Wu, Baojie Liu, Chengrong Qin, Shuangfei Wang, Shuangquan Yao. Mechanistic hydrogen bond mediated screening of hydroxyl functionalized additives for lignin condensation suppression[J]. Journal of Bioresources and Bioproducts, 2026, 11(2): 100233. doi: 10.1016/j.jobab.2026.100233
shu

Mechanistic hydrogen bond mediated screening of hydroxyl functionalized additives for lignin condensation suppression

doi: 10.1016/j.jobab.2026.100233

  • Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control, School of Light Industrial and Food Engineering, Guangxi University, Nanning 530004, China

More Information
  • Corresponding author: E-mail address: liubaojie@gxu.edu.cn (B. Liu); E-mail address: yaoshuangquan@gxu.edu.cn (S. Yao)
  • Received Date: 2025-09-26
  • Accepted Date: 2026-01-04
  • Rev Recd Date: 2025-12-27
    • Available Online: 2026-01-20
  • Publish Date: 2026-05-01
    Abstract
  • Hydroxyl functionalized additives (Ga-OHs) that can inhibit lignin re-polymerization have demonstrated significant potential in biomass resource conversion and utilization. However, the molecular mechanisms underlying this inhibitory effect remain poorly understood. This study systematically compares the lignin condensation inhibition capabilities of four hydroxyl functionalized additives with distinct functional group effects: salicylic acid, mannitol, 2-naphthol, and glycolic acid. Results indicate that lignin condensation inhibition is primarily associated with hydrogen bonding interactions formed between hydroxyl functionalized additives and oxygen containing functionalities on lignin side chains, while van der Waals interactions contribute as non-specific stabilizing contacts at the early stages. Rapid electron flow in short-chain compounds molecules stabilized the lignin structure. The strong hydrogen bond interaction between mannitol and oxygen groups in lignin branches (−80.38 kJ/mol) enhanced the stability of a separated lignin in a strong acidic environment, which resulted in a high β-O-4 content (up to 47.12 per 100 aromatic units). Here, we comparatively screened hydroxyl functionalized additives with different structures under dilute acid pretreatment and linked the quantitative outcomes of lignin condensation inhibition to density functional theory (DFT) validated noncovalent interactions. This work provides insight into the separation of low condensation lignin and informs the screening of additives with lignin condensation inhibition potential.

     

    • Data availability
    Data available on request from the authors.
    Declaration of competing interest
    The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
    Supplementary materials
    Supplementary material associated with this article can be found, in the online version, at doi:10.1016/j.jobab.2026.100233
    Peer review under the responsibility of Editorial Office of Journal of Bioresources and Bioproducts.
    FullText(HTML)
  • loading
    • References(45)
  • Abdelaziz, O.Y., Brink, D.P., Prothmann, J., Ravi, K., Sun, M.Z., García-Hidalgo, J., Sandahl, M., Hulteberg, C.P., Turner, C., Lidén, G., Gorwa-Grauslund, M.F., 2016. Biological valorization of low molecular weight lignin. Biotechnol. Adv. 34, 1318–1346. doi: 10.1016/j.biotechadv.2016.10.001
    Chen, C.J., Xu, P.F., Wang, X.H., 2024. Structure and mechanical properties of windmill palm fiber with different delignification treatments. J. Bioresour. Bioprod. 9, 102–112.
    Chu, Q.L., Tong, W.Y., Wu, S.F., Jin, Y.C., Hu, J.G., Song, K., 2021. Eco-friendly additives in acidic pretreatment to boost enzymatic saccharification of hardwood for sustainable biorefinery applications. Green Chem. 23, 4074–4086. doi: 10.1039/d1gc00738f
    Ci, Y.H., Yu, F., Zhou, C.X., Mo, H.E., Li, Z.Y., Ma, Y.Q., Zang, L.H., 2020. New ternary deep eutectic solvents for effective wheat straw deconstruction into its high-value utilization under near-neutral conditions. Green Chem. 22, 8713–8720. doi: 10.1039/d0gc03240a
    Cronin, D.J., Dunn, K., Zhang, X., Doherty, W.O.S., 2017. Relating dicarboxylic acid yield to residual lignin structural features. ACS Sustain. Chem. Eng. 5, 11695–11705. doi: 10.1021/acssuschemeng.7b03164
    Deng, B.J., Hou, Y.J., Wang, F., Bao, Y.Q., Zeng, F.Y., Qin, C.R., Liang, C., Huang, C.X., Ma, J.L., Yao, S.Q., 2022. Highly selective separation of Eucalyptus hemicellulose by salicylic acid treatment with both aromatic and hydroxy acids. Bioresour. Technol. 355, 127304. doi: 10.1016/j.biortech.2022.127304
    de Souza Rodrigues, J., Senna, A.M., de Oliveira, C.T., Botaro, V.R., 2021. New methodology for separating lignin fractions: GPC on a preparative scale with stationary phase of hydrogel derived from cellulose acetate. Ind. Crops Prod. 166, 113492. doi: 10.1016/j.indcrop.2021.113492
    Elmore, J.R., Dexter, G.N., Salvachúa, D., Martinez-Baird, J., Hatmaker, E.A., Huenemann, J.D., Klingeman, D.M., Peabody, G.L., Peterson, D.J., Singer, C., Beckham, G.T., Guss, A.M., 2021. Production of itaconic acid from alkali pretreated lignin by dynamic two stage bioconversion. Nat. Commun. 12, 2261. doi: 10.1038/s41467-021-22556-8
    Han, S.M., Wang, R.Z., Wang, K., Jiang, J.C., Xu, J.M., 2022. Low-condensed lignin and high-purity cellulose production from poplar by synergistic deep eutectic solvent-hydrogenolysis pretreatment. Bioresour. Technol. 363, 127905. doi: 10.1016/j.biortech.2022.127905
    Hotor, P., Hassanin, A.H., Akatwijuka, O., Gepreel, M.A.H., Yamamoto, M., Saito, Y., Abdel-Mawgood, A., 2024. Evaluating mechanism of banana pseudo-stem retting using seawater: A cost-effective surface pre-treatment approach. J. Bioresour. Bioprod. 9, 322–335.
    Jindal, M., Uniyal, P., Thallada, B., 2023. Reductive catalytic fractionation as a novel pretreatment/lignin-first approach for lignocellulosic biomass valorization: A review. Bioresour. Technol. 385, 129396. doi: 10.1016/j.biortech.2023.129396
    Li, P.H., Yang, C., Jiang, Z.W., Jin, Y.C., Wu, W.J., 2023. Lignocellulose pretreatment by deep eutectic solvents and related technologies: A review. J. Bioresour. Bioprod. 8, 33–44.
    Li, N., Yan, K.X., Rukkijakan, T., Liang, J.F., Liu, Y.T., Wang, Z.P., Nie, H.R., Muangmeesri, S., Castiella-Ona, G., Pan, X.J., Zhou, Q.F., Jiang, G.B., Zhou, G.Y., Ralph, J., Samec, J.S.M., Wang, F., 2024a. Selective lignin arylation for biomass fractionation and benign bisphenols. Nature 630, 381–386. doi: 10.1038/s41586-024-07446-5
    Li, R.Y., Zhang, D.H., Shen, B.Z., Lai, C.H., Yong, Q., 2024b. Alleviating lignin repolymerization facilitated the combined acid and deep eutectic solvent pretreatment of Populus. Ind. Crops Prod. 207, 117778. doi: 10.1016/j.indcrop.2023.117778
    Liu, H.F., Li, H.J., Lu, J.M., Zeng, S., Wang, M., Luo, N.C., Xu, S.T., Wang, F., 2018. Photocatalytic cleavage of C–C bond in lignin models under visible light on mesoporous graphitic carbon nitride through π–π stacking interaction. ACS Catal. 8, 4761–4771. doi: 10.1021/acscatal.8b00022
    Liu, Y.Z., Deak, N., Wang, Z.W., Yu, H.P., Hameleers, L., Jurak, E., Deuss, P.J., Barta, K., 2021. Tunable and functional deep eutectic solvents for lignocellulose valorization. Nat. Commun. 12, 5424. doi: 10.1038/s41467-021-25117-1
    Liu, Z.H., Li, B.Z., Yuan, J.S., Yuan, Y.J., 2022. Creative biological lignin conversion routes toward lignin valorization. Trends. Biotechnol. 40, 1550–1566. doi: 10.1016/j.tibtech.2022.09.014
    Liu, L., Liu, B.J., Li, X.Y., Wang, Z.L., Mu, L.L., Qin, C.R., Liang, C., Huang, C.X., Yao, S.Q., 2023. Mannitol assisted oxalic acid pretreatment of poplar for the deconstruction and separation of hemicellulose. Ind. Crops Prod. 200, 116811. doi: 10.1016/j.indcrop.2023.116811
    Luo, Y.D., Liu, B.J., Deng, B.J., Long, X., Du, Z.C., Qin, C.R., Liang, C., Huang, C.X., Yao, S.Q., 2024. Efficient and accurate fractionation of Eucalyptus using glycolic acid-catalyzed hydrothermal treatment and alkali treatment comprehensive technology. Ind. Crops Prod. 208, 117791. doi: 10.1016/j.indcrop.2023.117791
    Madadi, M., Elsayed, M., Song, G.J., Shafiei-Alavijeh, R., Denayer, J.F.M., Kargaran, E., Al Azad, S., Karimi, K., Sun, F.B., Gupta, V.K., 2025a. Transformative biorefinery model for biomass valorization into biofuel and renewable platform chemicals. J. Energy Chem. 110, 109–123. doi: 10.1016/j.jechem.2025.06.016
    Malayil, S., Loughran, L., Ulken, F.M., Satyavolu, J., 2024. Exploring hemp seed hull biomass for an integrated C-5 biorefinery: Xylose and activated carbon. J. Bioresour. Bioprod. 9, 310–321.
    Nisha, S.S., Nikzad, M., Al Kobaisi, M., Truong, V.K., Sbarski, I., 2019. The role of ionic-liquid extracted lignin micro/nanoparticles for functionalisation of an epoxy-based composite matrix. Compos. Sci. Technol. 174, 11–19. doi: 10.1016/j.compscitech.2019.02.009
    Rath, S., Pradhan, D., Du, H.S., Mohapatra, S., Thatoi, H., 2024. Transforming lignin into value-added products: Perspectives on lignin chemistry, lignin-based biocomposites, and pathways for augmenting ligninolytic enzyme production. Adv. Compos. Hybrid Mater. 7, 27.
    Rigo, D., Fechter, T., Capanema, E., Diment, D., Alopaeus, M., Tarasov, D., Cantero, D., Balakshin, M., 2024. Isolation of β-O-4-rich lignin from birch in high yields enabled by continuous-flow supercritical water treatment. ChemSusChem 18, e202401683.
    Savenko, E.S., Kostjukov, V.V., 2023. Theoretical study of the excitation of proflavine H-dimers in an aqueous solution: The effect of functionals and dispersion corrections. Phys. Chem. Chem. Phys. 25, 12259–12276. doi: 10.1039/d3cp00882g
    Seidi, F., Liu, Y.Q., Huang, Y., Xiao, H.N., Crespy, D., 2025. Chemistry of lignin and condensed tannins as aromatic biopolymers. Chem. Soc. Rev. 54, 3140–3232. doi: 10.1039/d4cs00440j
    Shao, Y., Xia, Q.N., Dong, L., Liu, X.H., Han, X., Parker, S.F., Cheng, Y.Q., Daemen, L.L., Ramirez-Cuesta, A.J., Yang, S.H., Wang, Y.Q., 2017. Selective production of arenes via direct lignin upgrading over a niobium-based catalyst. Nat. Commun. 8, 16104. doi: 10.1038/ncomms16104
    Shuai, L., Amiri, M.T., Questell-Santiago, Y.M., Héroguel, F., Li, Y.D., Kim, H., Meilan, R., Chapple, C., Ralph, J., Luterbacher, J.S., 2016. Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization. Science 354, 329–333. doi: 10.1126/science.aaf7810
    Song, G.J., Madadi, M., Meng, X.Z., Sun, C.H., Aghbashlo, M., Sun, F.B., Ragauskas, A.J., Tabatabaei, M., Ashori, A., 2024. Double in-situ lignin modification in surfactant-assisted glycerol organosolv pretreatment of sugarcane bagasse towards efficient enzymatic hydrolysis. Chem. Eng. J. 481, 148713. doi: 10.1016/j.cej.2024.148713
    Tan, X., Yang, C.D., Li, Y.B., Zhang, Q., Sheng, Y.Q., Lai, C.H., 2025. Lignin fractionation and condensation in aromatic-additive-assisted acidic pretreatment and their influence on lignin’s effect on the enzymatic hydrolysis. Int. J. Biol. Macromol. 295, 139471.
    Wang, W.X., Kong, Y., Peng, J.J., Li, B., Xu, H.F., 2022. Probing the mechanism of green solvent solubilization of hemicellulose based on molecular dynamics simulations. Ind. Crops Prod. 186, 115159.
    Wang, Y.L., Wu, J., Shen, R.H., Li, Y.B., Ma, G.F., Qi, S., Wu, W.J., Jin, Y.C., Jiang, B., 2023. A mild iodocyclohexane demethylation for highly enhancing antioxidant activity of lignin. J. Bioresour. Bioprod. 8, 306–317. doi: 10.3390/brainsci13020306
    Wang, X., Liu, Y., Luo, S.Y., Liu, B.J., Yao, S.Q., Qin, C.R., Wang, S.F., Liang, C., 2025. Structural characteristics of hemicelluloses and lignin-carbohydrate complexes in alkaline-extracted bamboo green, core, and yellow. J. Bioresour. Bioprod. 10, 386–396. doi: 10.47577/tssj.v72i1.12892
    Wang, Z.W., Deuss, P.J., 2023. The isolation of lignin with native-like structure. Biotechnol. Adv. 68, 108230.
    Wong, S.S., Shu, R.Y., Zhang, J.G., Liu, H.C., Yan, N., 2020. Downstream processing of lignin derived feedstock into end products. Chem. Soc. Rev. 49, 5510–5560. doi: 10.1039/d0cs00134a
    Xiao, T.Y., Hou, M.J., Guo, X., Cao, X.Y., Li, C.G., Zhang, Q., Jia, W.C., Sun, Y.N., Guo, Y.Z., Shi, H.Q., 2024. Recent progress in deep eutectic solvent(DES) fractionation of lignocellulosic components: A review. Renew. Sustain. Energy Rev. 192, 114243.
    Xie, W.L., Hu, B., Xia, Y.G., Song, G.Y., Liu, J., Liu, Y., Lu, Q., 2023. A novel insight into the bimolecular concerted interaction in lignin pyrolysis: Tautomer-assisted hydrogen transfer mechanism. Chem. Eng. J. 463, 142513.
    Xu, H.F., Kong, Y., Peng, J.J., Wang, W.X., Li, B., 2021. Mechanism of deep eutectic solvent delignification: Insights from molecular dynamics simulations. ACS Sustain. Chem. Eng. 9(20), 7101–7111. doi: 10.1021/acssuschemeng.1c01260
    Yang, H.Y., Jin, Y., Shi, Z.J., Wang, D.W., Zhao, P., Yang, J., 2020. Effect of hydrothermal pretreated bamboo lignin on cellulose saccharification for bioethanol production. Ind. Crops Prod. 156, 112865.
    Zeng, H.L., Liu, B.J., Li, J., Li, M., Peng, M.J., Qin, C.R., Liang, C., Huang, C.X., Li, X.P., Yao, S.Q., 2022. Efficient separation of bagasse lignin by freeze–thaw-assisted p-toluenesulfonic acid pretreatment. Bioresour. Technol. 351, 126951.
    Zhang, Y.Q., He, H.Y., Dong, K., Fan, M.H., Zhang, S.J., 2017. A DFT study on lignin dissolution in imidazolium-based ionic liquids. RSC Adv. 7, 12670–12681.
    Zhang, C.Y., Yang, X.P., Yang, S., Liu, Z.Q., Zhang, L., He, H.L., Qiu, W.M., Zhuo, R.Y., Xu, J., Wang, L., 2023a. Valorization of heavy metal enriched phytoremediation biomass using a deep eutectic solvent (DES). Green Chem. 25, 771–778. doi: 10.1039/d2gc04190a
    Zhang, Y.L., Ren, H.W., Li, B.C., Udin, S.M., Maarof, H., Zhou, W., Cheng, F.F., Yang, J.R., Liu, Y.Z., Alias, H., Duan, E.H., 2023b. Mechanistic insights into the lignin dissolution behavior in amino acid based deep eutectic solvents. Int. J. Biol. Macromol. 242, 124829.
    Zhao, Y.L., Zhao, D.Q., He, J.P., Ma, K.B., Zhu, J.T., Liu, J.R., Zhang, Y.Q., Xia, Q.Q., Li, T., 2025. Protective fractionation of highly uncondensed lignin with high purity and high yield: New insights into propanediol-blocked lignin condensation. Green Chem. 27, 4244–4258. doi: 10.1039/d5gc00024f
    Zhou, X., Zeng, X., Hu, S.N., Zhou, Y., Xie, M.T., Yue, F.X., 2024. Highly uncondensed lignin extraction in the novel green L-cysteine/lactic acid cosolvent system. Chem. Eng. J. 497, 154340.
    • Relative Articles
    • Supplements(0)
    • Cited By
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Figures(5)  / Tables(4)

    Get Citation
    PDF
    XML

    Article Metrics

    Article views (25) PDF downloads(0) Cited by()
    Proportional views
    Related
    • Wechat: JBB生物质资源与工程

    Copyright © 2019 Editorial Office of Journal of Bioresources and Bioproducts

    Supported by: Beijing Renhe Information Technology Co. Ltd  support: info@rhhz.net

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return