Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives
Efficient and highly regioselective synthesis of the potential 6′′-O-sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was achieved using Candida antarctica lipase B for the first time. Under the optimal conditions, the initial reaction rate, maximum substrate conversion...
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ftpubmed:oai:pubmedcentral.nih.gov:5030401 2023-05-15T13:56:31+02:00 Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives Wang, Zhaoyu Bi, Yanhong Yang, Rongling Zhao, Xiangjie Jiang, Ling Zhu, Chun Zhao, Yuping Jia, Jianbo 2016 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5030401/ http://www.ncbi.nlm.nih.gov/pubmed/27668253 https://doi.org/10.1155/2016/4357052 en eng Hindawi Publishing Corporation http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5030401/ http://www.ncbi.nlm.nih.gov/pubmed/27668253 http://dx.doi.org/10.1155/2016/4357052 Copyright © 2016 Zhaoyu Wang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. CC-BY Research Article Text 2016 ftpubmed https://doi.org/10.1155/2016/4357052 2016-10-02T00:12:24Z Efficient and highly regioselective synthesis of the potential 6′′-O-sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was achieved using Candida antarctica lipase B for the first time. Under the optimal conditions, the initial reaction rate, maximum substrate conversion, and 6′′-regioselectivity were as high as 8.65 mM/h, 100%, and 100%, respectively. Kinetic and operational stability investigations evidently demonstrated excellent enzyme compatibility of the 2-MeTHF compared to the traditional organic solvents. With respect to the antioxidant properties, three unsaturated ester derivatives showed slightly lower DPPH radical scavenging activities than the parent agent. Interestingly, further studies also revealed that the antiradical capacities of the acylates decreased with the elongation of the unsaturated aliphatic chain length from C4 to C11. The reason might be attributed to the increased steric hindrance derived from the acyl residues in derivatives. Text Antarc* Antarctica PubMed Central (PMC) BioMed Research International 2016 1 7 |
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Research Article Wang, Zhaoyu Bi, Yanhong Yang, Rongling Zhao, Xiangjie Jiang, Ling Zhu, Chun Zhao, Yuping Jia, Jianbo Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
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Research Article |
description |
Efficient and highly regioselective synthesis of the potential 6′′-O-sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was achieved using Candida antarctica lipase B for the first time. Under the optimal conditions, the initial reaction rate, maximum substrate conversion, and 6′′-regioselectivity were as high as 8.65 mM/h, 100%, and 100%, respectively. Kinetic and operational stability investigations evidently demonstrated excellent enzyme compatibility of the 2-MeTHF compared to the traditional organic solvents. With respect to the antioxidant properties, three unsaturated ester derivatives showed slightly lower DPPH radical scavenging activities than the parent agent. Interestingly, further studies also revealed that the antiradical capacities of the acylates decreased with the elongation of the unsaturated aliphatic chain length from C4 to C11. The reason might be attributed to the increased steric hindrance derived from the acyl residues in derivatives. |
format |
Text |
author |
Wang, Zhaoyu Bi, Yanhong Yang, Rongling Zhao, Xiangjie Jiang, Ling Zhu, Chun Zhao, Yuping Jia, Jianbo |
author_facet |
Wang, Zhaoyu Bi, Yanhong Yang, Rongling Zhao, Xiangjie Jiang, Ling Zhu, Chun Zhao, Yuping Jia, Jianbo |
author_sort |
Wang, Zhaoyu |
title |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_short |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_full |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_fullStr |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_full_unstemmed |
Enzymatic Synthesis of Sorboyl-Polydatin Prodrug in Biomass-Derived 2-Methyltetrahydrofuran and Antiradical Activity of the Unsaturated Acylated Derivatives |
title_sort |
enzymatic synthesis of sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran and antiradical activity of the unsaturated acylated derivatives |
publisher |
Hindawi Publishing Corporation |
publishDate |
2016 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5030401/ http://www.ncbi.nlm.nih.gov/pubmed/27668253 https://doi.org/10.1155/2016/4357052 |
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Antarc* Antarctica |
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Antarc* Antarctica |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5030401/ http://www.ncbi.nlm.nih.gov/pubmed/27668253 http://dx.doi.org/10.1155/2016/4357052 |
op_rights |
Copyright © 2016 Zhaoyu Wang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
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CC-BY |
op_doi |
https://doi.org/10.1155/2016/4357052 |
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BioMed Research International |
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2016 |
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1 |
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7 |
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1766264015491694592 |