Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient
Phenolation is one of the effective strategies to synthesize lignin-based polyphenols, improve lignin's properties, and extend its value-added applications in biological, medicinal and cosmetic fields. Herein, by taking the structural feature advantage of lignin, an effective and green strategy...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co., Ltd.
2024-05-01
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| Series: | Journal of Bioresources and Bioproducts |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2369969824000203 |
| _version_ | 1797210034356092928 |
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| author | Yuanlong Guo Pengcheng Liu Lei Deng Changwei Lui Michael North Gang Hu Qitian Huang Zongbao Kent Zhao Haibo Xie |
| author_facet | Yuanlong Guo Pengcheng Liu Lei Deng Changwei Lui Michael North Gang Hu Qitian Huang Zongbao Kent Zhao Haibo Xie |
| author_sort | Yuanlong Guo |
| collection | DOAJ |
| description | Phenolation is one of the effective strategies to synthesize lignin-based polyphenols, improve lignin's properties, and extend its value-added applications in biological, medicinal and cosmetic fields. Herein, by taking the structural feature advantage of lignin, an effective and green strategy was developed to molecularly engineer lignin into a robust lignin-3-(2-hydroxyphenyl)propionate ester (LPPE) derivative via a transesterification reaction between 3,4-dihydrocoumarin (DHC) and the aliphatic hydroxyls in lignin under organocatalysis. The strategy is optimized and the novel derivative was systematically characterized by 1H, 13C and 31P nuclear magnetic resonance (NMR) and Fourier transform infrared (FT-IR) spectroscopy. The findings indicated that the successful introduction of 3-(2-hydroxyphenyl)propionate groups using a OH groups/DHC/organic base molar ratio of 1꞉1꞉0.3 at 120 °C for 6 h increased the content of phenolic hydroxyl groups from 1.793 1 to 3.017 9 mmol/g, and the LPPE exhibited excellent ultraviolet-absorbing and antioxidant performance with up to 90% free radical scavenging activity within 20 min using 5 mg/mL of LPPE. In addition, good biocompatibility and a high Sun protection factor (SPF) value of 40.9 were achieved at 5% (w) dosage of LPPE in the cream, indicating its significant application potential in sunscreen. |
| first_indexed | 2024-04-24T10:04:10Z |
| format | Article |
| id | doaj.art-5f0944d0e522448ab0abdff420435ded |
| institution | Directory Open Access Journal |
| issn | 2369-9698 |
| language | English |
| last_indexed | 2024-04-24T10:04:10Z |
| publishDate | 2024-05-01 |
| publisher | KeAi Communications Co., Ltd. |
| record_format | Article |
| series | Journal of Bioresources and Bioproducts |
| spelling | doaj.art-5f0944d0e522448ab0abdff420435ded2024-04-13T04:21:26ZengKeAi Communications Co., Ltd.Journal of Bioresources and Bioproducts2369-96982024-05-0192197210Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredientYuanlong Guo0Pengcheng Liu1Lei Deng2Changwei Lui3Michael North4Gang Hu5Qitian Huang6Zongbao Kent Zhao7Haibo Xie8Department of Polymeric Materials & Engineering, Guizhou University, Guiyang 550025, ChinaDepartment of Polymeric Materials & Engineering, Guizhou University, Guiyang 550025, ChinaKZJ New Materials Group Guizhou Co. Ltd., Guizhou 551200, ChinaKZJ New Materials Group Guizhou Co. Ltd., Guizhou 551200, ChinaGreen Chemistry Centre of Excellence, Department of Chemistry, University of York, York YO10 5DD, UKDepartment of Polymeric Materials & Engineering, Guizhou University, Guiyang 550025, ChinaDalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, ChinaDalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, ChinaDepartment of Polymeric Materials & Engineering, Guizhou University, Guiyang 550025, China; Corresponding author.Phenolation is one of the effective strategies to synthesize lignin-based polyphenols, improve lignin's properties, and extend its value-added applications in biological, medicinal and cosmetic fields. Herein, by taking the structural feature advantage of lignin, an effective and green strategy was developed to molecularly engineer lignin into a robust lignin-3-(2-hydroxyphenyl)propionate ester (LPPE) derivative via a transesterification reaction between 3,4-dihydrocoumarin (DHC) and the aliphatic hydroxyls in lignin under organocatalysis. The strategy is optimized and the novel derivative was systematically characterized by 1H, 13C and 31P nuclear magnetic resonance (NMR) and Fourier transform infrared (FT-IR) spectroscopy. The findings indicated that the successful introduction of 3-(2-hydroxyphenyl)propionate groups using a OH groups/DHC/organic base molar ratio of 1꞉1꞉0.3 at 120 °C for 6 h increased the content of phenolic hydroxyl groups from 1.793 1 to 3.017 9 mmol/g, and the LPPE exhibited excellent ultraviolet-absorbing and antioxidant performance with up to 90% free radical scavenging activity within 20 min using 5 mg/mL of LPPE. In addition, good biocompatibility and a high Sun protection factor (SPF) value of 40.9 were achieved at 5% (w) dosage of LPPE in the cream, indicating its significant application potential in sunscreen.http://www.sciencedirect.com/science/article/pii/S2369969824000203Phenolation of ligninOrganocatalysis3,4-dihydrocoumarinAntioxidantSunscreen cream |
| spellingShingle | Yuanlong Guo Pengcheng Liu Lei Deng Changwei Lui Michael North Gang Hu Qitian Huang Zongbao Kent Zhao Haibo Xie Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient Journal of Bioresources and Bioproducts Phenolation of lignin Organocatalysis 3,4-dihydrocoumarin Antioxidant Sunscreen cream |
| title | Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient |
| title_full | Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient |
| title_fullStr | Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient |
| title_full_unstemmed | Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient |
| title_short | Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient |
| title_sort | molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient |
| topic | Phenolation of lignin Organocatalysis 3,4-dihydrocoumarin Antioxidant Sunscreen cream |
| url | http://www.sciencedirect.com/science/article/pii/S2369969824000203 |
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