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Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems
Vinyl stearate was added to enzymatic transesterification of (−)-Epigallocatechin-3-O-gallate (EGCG) to enhance its lipophilicity and antioxidant ability in a non-aqueous system. The lipase DF “Amano” 15 was used as the catalyst. The optimal reaction conditions were: acetonitrile as the solvent, the...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8389292/ https://www.ncbi.nlm.nih.gov/pubmed/34439530 http://dx.doi.org/10.3390/antiox10081282 |
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author | Jiang, Chengyu Wang, Li Huang, Xin Zhu, Song Ma, Chaoyang Wang, Hongxin |
author_facet | Jiang, Chengyu Wang, Li Huang, Xin Zhu, Song Ma, Chaoyang Wang, Hongxin |
author_sort | Jiang, Chengyu |
collection | PubMed |
description | Vinyl stearate was added to enzymatic transesterification of (−)-Epigallocatechin-3-O-gallate (EGCG) to enhance its lipophilicity and antioxidant ability in a non-aqueous system. The lipase DF “Amano” 15 was used as the catalyst. The optimal reaction conditions were: acetonitrile as the solvent, the molar ratio of vinyl stearate: EGCG as 3:1, an enzyme amount of 4.0% (ratio of substrate mass), and a reaction temperature and time of 50 °C and 96 h, respectively, achieving 65.2% EGCG conversion. HPLC–MS and NMR were used to determine the structure of EGCG stearyl derivative (3″,5″-2-O-stearyl-EGCG). The lipophilicity of EGCG stearyl derivatives (3.49 ± 0.34) was higher (5.06 times) than that of the parent EGCG (0.69 ± 0.08). Furthermore, EGCG stearyl derivatives had excellent lipid oxidation compared with BHT, BHA, and parent EGCG. The POVs of soybean oil with EGCG stearyl derivatives (18.17 ± 0.92 mEq/kg) were significantly reduced (by 62.5%) at 21 d compared with those of EGCG (48.50 ± 1.23 mEq/kg). These results indicate that EGCG derivatives have broad antioxidant application prospects in lipophilic environments/high-fat food. |
format | Online Article Text |
id | pubmed-8389292 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-83892922021-08-27 Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems Jiang, Chengyu Wang, Li Huang, Xin Zhu, Song Ma, Chaoyang Wang, Hongxin Antioxidants (Basel) Article Vinyl stearate was added to enzymatic transesterification of (−)-Epigallocatechin-3-O-gallate (EGCG) to enhance its lipophilicity and antioxidant ability in a non-aqueous system. The lipase DF “Amano” 15 was used as the catalyst. The optimal reaction conditions were: acetonitrile as the solvent, the molar ratio of vinyl stearate: EGCG as 3:1, an enzyme amount of 4.0% (ratio of substrate mass), and a reaction temperature and time of 50 °C and 96 h, respectively, achieving 65.2% EGCG conversion. HPLC–MS and NMR were used to determine the structure of EGCG stearyl derivative (3″,5″-2-O-stearyl-EGCG). The lipophilicity of EGCG stearyl derivatives (3.49 ± 0.34) was higher (5.06 times) than that of the parent EGCG (0.69 ± 0.08). Furthermore, EGCG stearyl derivatives had excellent lipid oxidation compared with BHT, BHA, and parent EGCG. The POVs of soybean oil with EGCG stearyl derivatives (18.17 ± 0.92 mEq/kg) were significantly reduced (by 62.5%) at 21 d compared with those of EGCG (48.50 ± 1.23 mEq/kg). These results indicate that EGCG derivatives have broad antioxidant application prospects in lipophilic environments/high-fat food. MDPI 2021-08-13 /pmc/articles/PMC8389292/ /pubmed/34439530 http://dx.doi.org/10.3390/antiox10081282 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Jiang, Chengyu Wang, Li Huang, Xin Zhu, Song Ma, Chaoyang Wang, Hongxin Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems |
title | Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems |
title_full | Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems |
title_fullStr | Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems |
title_full_unstemmed | Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems |
title_short | Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems |
title_sort | identification and antioxidant abilities of enzymatic-transesterification (−)-epigallocatechin-3-o-gallate stearyl derivatives in non-aqueous systems |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8389292/ https://www.ncbi.nlm.nih.gov/pubmed/34439530 http://dx.doi.org/10.3390/antiox10081282 |
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