Role Evaluation of Active Groups in Lignin on UV-Shielding Performance

Li, Yarong; Zhao, Siyu; Hu, Dongbin; Ragauskas, Arthur J.; Cao, Danyu; Liu, Wenqing; Si, Chuanling; Xu, Ting; Zhao, Peitao; Song, Xueping; Li, Kai

doi:10.1021/acssuschemeng.2c02714

Role Evaluation of Active Groups in Lignin on UV-Shielding Performance

Journal Article · Tue Aug 30 00:00:00 EDT 2022 · ACS Sustainable Chemistry & Engineering

DOI:https://doi.org/10.1021/acssuschemeng.2c02714· OSTI ID:1885231

Li, Yarong ^[1]; Zhao, Siyu ^[2]; Hu, Dongbin ^[1]; ^[3]; Cao, Danyu ^[4]; Liu, Wenqing ^[4]; ^[5]; Xu, Ting ^[5]; Zhao, Peitao ^[6]; ^[7]; Li, Kai ^[1]

Guangxi Univ., Nanning (China); Provincial and Ministerial Collaborative Innovation Center for Sugar Industry, Nanning (China); Engineering Research Center for Sugar Industry and Comprehensive Utilization, Ministry of Education, Nanning (China)
Guangxi Univ., Nanning (China); Key Laboratory of Clean Pulp & Papermaking and Pollution Control, Nanning (China)
Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Guangxi Univ., Nanning (China)
Tianjin Univ. of Technology, Tianjin (China)
China Univ. of Mining and Technology, Xuzhou, Jiangsu (China)
Guangxi Univ., Nanning (China); Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control, Nanning (China)

The contribution of the active groups in lignin to ultraviolet (UV)-shielding performance still remains unclear. In this study, we employed 16 lignin model compounds and theoretical calculations to ascertain the contribution of different functional groups to UV-shielding performance. These results showed that the order of UV-shielding performance on functional groups was -C=C–CHO > -C=C–COOH > -C=C–CH₂OH > --C=C > quinone > -COOH > -OCH₃ ≈ -OH. Moreover, the synergism between the para-substituted electron-donating group -OH and the electron-withdrawing group allyl on the aromatic ring played a major role in UV-shielding performance of lignin models, whereas the additive effect of meta/ortho-substituted -OCH₃ played a secondary role. Furthermore, we found that the hydrophile–lipophile balance (HLB) value of lignin models also greatly affected the sunscreen protection factor (SPF) of lignin model-based sunscreens. A closer HLB value of lignin to 8.89 corresponded with a higher SPF of the lignin model-based sunscreen. The commercial photoprotective ingredient ethylhexyl methoxycinnamate (EHMC) and lignin models had a synergistic effect on UV-shielding performance caused by the π–π stacking interaction between the parallel-displaced stacked aromatic rings of lignin models and EHMC. Additionally, the UV irradiation test showed that these sunscreens prepared using lignin models and EHMC exhibited good photostability.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: Foundation of Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control; Guangxi Innovation Driven Development Special Fund Project, China; National Key Research and Development Program of China; National Natural Science Foundation of China; Natural Science Foundation of Guangxi Province, China; USDOE

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1885231

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 36 Vol. 10; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (35)

New Opportunities in the Valorization of Technical Lignins Balakshin, Mikhail Yu.; Capanema, Ewellyn A.; Sulaeva, Irina ChemSusChem, Vol. 14, Issue 4 https://doi.org/10.1002/cssc.202002553	journal	January 2021
UV‐Shielding Performance and Color of Lignin and its Application to Sunscreen Li, Yarong; Zhao, Siyu; Song, Xueping Macromolecular Materials and Engineering, Vol. 307, Issue 2 https://doi.org/10.1002/mame.202100628	journal	November 2021
Non-adiabatic Dynamics Mechanism in Excited State of Novel UV Protective Sunscreen in Rice: Conical Intersection Promotes Internal Conversion Zhao, Xiaoying; Wu, Yanqing; Shi, Yanan Journal of Cluster Science, Vol. 32, Issue 4 https://doi.org/10.1007/s10876-020-01819-2	journal	August 2020
Physico-chemical characterization of lignins from different sources for use in phenol–formaldehyde resin synthesis Tejado, A.; Peña, C.; Labidi, J. Bioresource Technology, Vol. 98, Issue 8 https://doi.org/10.1016/j.biortech.2006.05.042	journal	May 2007
A review on biopolymer production via lignin valorization Rajesh Banu, J.; Kavitha, S.; Yukesh Kannah, R. Bioresource Technology, Vol. 290 https://doi.org/10.1016/j.biortech.2019.121790	journal	October 2019
Challenges and future of chemical assisted heavy oil recovery processes Ahmadi, Mohammadali; Chen, Zhangxin Advances in Colloid and Interface Science, Vol. 275 https://doi.org/10.1016/j.cis.2019.102081	journal	January 2020
Atomic Force Microscopy Measurement in the Lignosulfonate/Inorganic Silica System: From Dispersion Mechanism Study to Product Design Wang, Jingyu; Qian, Yong; Zhou, Yijie Engineering, Vol. 7, Issue 8 https://doi.org/10.1016/j.eng.2021.07.004	journal	August 2021
Lignin for white natural sunscreens Lee, Sang Cheon; Tran, Thi Minh Thu; Choi, Joon Weon International Journal of Biological Macromolecules, Vol. 122 https://doi.org/10.1016/j.ijbiomac.2018.10.184	journal	February 2019
Current advancement on the isolation, characterization and application of lignin Liao, Jing Jing; Latif, Nur Hanis Abd; Trache, Djalal International Journal of Biological Macromolecules, Vol. 162 https://doi.org/10.1016/j.ijbiomac.2020.06.168	journal	November 2020
Fabrication of uniform lignin colloidal spheres for developing natural broad-spectrum sunscreens with high sun protection factor Qian, Yong; Zhong, Xiaowen; Li, Ying Industrial Crops and Products, Vol. 101 https://doi.org/10.1016/j.indcrop.2017.03.001	journal	July 2017
Review of environmental effects of oxybenzone and other sunscreen active ingredients Schneider, Samantha L.; Lim, Henry W. Journal of the American Academy of Dermatology, Vol. 80, Issue 1 https://doi.org/10.1016/j.jaad.2018.06.033	journal	January 2019
Theoretical insights on flavanones as antioxidants and UV filters: A TDDFT and NLMO study Ajmala Shireen, P.; Abdul Mujeeb, V. M.; Muraleedharan, K. Journal of Photochemistry and Photobiology B: Biology, Vol. 170 https://doi.org/10.1016/j.jphotobiol.2017.04.021	journal	May 2017
Photoprotection assessment of olive (Olea europaea L.) leaves extract standardized to oleuropein: In vitro and in silico approach for improved sunscreens da Silva, Anne C. P.; Paiva, Juliana P.; Diniz, Raiane R. Journal of Photochemistry and Photobiology B: Biology, Vol. 193 https://doi.org/10.1016/j.jphotobiol.2019.03.003	journal	April 2019
Photostability of sunscreens Kockler, Jutta; Oelgemöller, Michael; Robertson, Sherryl Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 13, Issue 1 https://doi.org/10.1016/j.jphotochemrev.2011.12.001	journal	March 2012
The Nature and Applications of π–π Interactions: A Perspective Thakuria, Ranjit; Nath, Naba K.; Saha, Binoy K. Crystal Growth & Design, Vol. 19, Issue 2 https://doi.org/10.1021/acs.cgd.8b01630	journal	January 2019
Phenol and Toluene Stacking Interactions, Including Interactions at Large Horizontal Displacements. Study of Crystal Structures and Calculation of Potential Energy Surfaces Živković, Jelena M.; Stanković, Ivana M.; Ninković, Dragan B. Crystal Growth & Design, Vol. 20, Issue 2 https://doi.org/10.1021/acs.cgd.9b01353	journal	December 2019
Occurrence, Distribution, and Fate of Organic UV Filters in Coral Communities Tsui, Mirabelle M. P.; Lam, James C. W.; Ng, T. Y. Environmental Science & Technology, Vol. 51, Issue 8 https://doi.org/10.1021/acs.est.6b05211	journal	April 2017
Fabrication of Light-Colored Lignin Microspheres for Developing Natural Sunscreens with Favorable UV Absorbability and Staining Resistance Zhang, Hui; Liu, Xinxin; Fu, Shiyu Industrial & Engineering Chemistry Research, Vol. 58, Issue 31 https://doi.org/10.1021/acs.iecr.9b02086	journal	July 2019
Long-Acting and Safe Sunscreens with Ultrahigh Sun Protection Factor via Natural Lignin Encapsulation and Synergy Qiu, Xueqing; Li, Ying; Qian, Yong ACS Applied Bio Materials, Vol. 1, Issue 5 https://doi.org/10.1021/acsabm.8b00138	journal	September 2018
Sunscreen Performance of Lignin from Different Technical Resources and Their General Synergistic Effect with Synthetic Sunscreens Qian, Yong; Qiu, Xueqing; Zhu, Shiping ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 7 https://doi.org/10.1021/acssuschemeng.6b00934	journal	May 2016
Synergistic Antioxidant Performance of Lignin and Quercetin Mixtures Liu, Di; Li, Ying; Qian, Yong ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 9 https://doi.org/10.1021/acssuschemeng.7b02282	journal	August 2017
The nature of .pi.-.pi. interactions Hunter, Christopher A.; Sanders, Jeremy K. M. Journal of the American Chemical Society, Vol. 112, Issue 14 https://doi.org/10.1021/ja00170a016	journal	July 1990
Molecular Modeling Studies of the Structural, Electronic, and UV Absorption Properties of Benzophenone Derivatives Corrêa, Bianca A. M.; Gonçalves, Arlan S.; de Souza, Alessandra M. T. The Journal of Physical Chemistry A, Vol. 116, Issue 45 https://doi.org/10.1021/jp306130y	journal	November 2012
Lignin: a nature-inspired sun blocker for broad-spectrum sunscreens Qian, Yong; Qiu, Xueqing; Zhu, Shiping Green Chemistry, Vol. 17, Issue 1 https://doi.org/10.1039/c4gc01333f	journal	January 2015
Towards lignin-based functional materials in a sustainable world Kai, Dan; Tan, Mein Jin; Chee, Pei Lin Green Chemistry, Vol. 18, Issue 5 https://doi.org/10.1039/c5gc02616d	journal	January 2016
Photoprotection: extending lessons learned from studying natural sunscreens to the design of artificial sunscreen constituents Baker, Lewis A.; Marchetti, Barbara; Karsili, Tolga N. V. Chemical Society Reviews, Vol. 46, Issue 12 https://doi.org/10.1039/c7cs00102a	journal	January 2017
A practicable process for lignin color reduction: fractionation of lignin using methanol/water as a solvent Zhang, Hui; Bai, Youcan; Yu, Boming Green Chem., Vol. 19, Issue 21 https://doi.org/10.1039/c7gc01974b	journal	January 2017
Spherical lignin particles: a review on their sustainability and applications Österberg, Monika; Sipponen, Mika H.; Mattos, Bruno D. Green Chemistry, Vol. 22, Issue 9 https://doi.org/10.1039/d0gc00096e	journal	January 2020
Revisiting lignin: a tour through its structural features, characterization methods and applications Melro, Elodie; Filipe, Alexandra; Sousa, Dora New Journal of Chemistry, Vol. 45, Issue 16 https://doi.org/10.1039/d0nj06234k	journal	January 2021
Review on lignin modifications toward natural UV protection ingredient for lignin-based sunscreens Tran, My Ha; Phan, Dieu-Phuong; Lee, Eun Yeol Green Chemistry, Vol. 23, Issue 13 https://doi.org/10.1039/d1gc01139a	journal	January 2021
Mechanisms of sunscreen failure Wright, Mandy Wartha; Wright, Steven T.; Wagner, Richard F. Journal of the American Academy of Dermatology, Vol. 44, Issue 5 https://doi.org/10.1067/mjd.2001.113685	journal	May 2001
Quantifying Direct DNA Damage in the Basal Layer of Skin Exposed to UV Radiation from Sunbeds Barnard, Isla Rose Mary; Tierney, Patrick; Campbell, Catherine Louise Photochemistry and Photobiology, Vol. 94, Issue 5 https://doi.org/10.1111/php.12935	journal	June 2018
Sunscreen Products as Emerging Pollutants to Coastal Waters Tovar-Sánchez, Antonio; Sánchez-Quiles, David; Basterretxea, Gotzon PLoS ONE, Vol. 8, Issue 6 https://doi.org/10.1371/journal.pone.0065451	journal	June 2013
Current Understanding of the Correlation of Lignin Structure with Biomass Recalcitrance Li, Mi; Pu, Yunqiao; Ragauskas, Arthur J. Frontiers in Chemistry, Vol. 4 https://doi.org/10.3389/fchem.2016.00045	journal	November 2016
Repurposing of Drug Candidates for Treatment of Skin Cancer Cortés, Hernán; Reyes-Hernández, Octavio D.; Alcalá-Alcalá, Sergio Frontiers in Oncology, Vol. 10 https://doi.org/10.3389/fonc.2020.605714	journal	January 2021

Similar Records

Revealing the relationship between molecular weight of lignin and its color, UV-protecting property

Journal Article · Sun Nov 13 19:00:00 EST 2022 · International Journal of Biological Macromolecules · OSTI ID:1969806

Lignin as a bioactive polymer and heavy metal absorber- an overview

Journal Article · Wed Sep 21 20:00:00 EDT 2022 · Chemosphere · OSTI ID:1896978

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
59 BASIC BIOLOGICAL SCIENCES
Functional groups
Lignin models
Sunscreen
UV-shielding performance
π-π stacking interaction

Role Evaluation of Active Groups in Lignin on UV-Shielding Performance

Citation Formats

References (35)

Similar Records

Related Subjects