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Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro
BACKGROUND: Flavonoid glycosides have many beneficial effects on health, but these bioactivities tend to decrease after oral administration owing to their poor lipophilicity. In this study, a facile whole-cell-based method was developed for selective preparation of monoester or diester of troxerutin...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
BioMed Central
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6106897/ https://www.ncbi.nlm.nih.gov/pubmed/30134913 http://dx.doi.org/10.1186/s12934-018-0976-x |
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author | Xin, Xuan Zhang, Mengmeng Li, Xiaofeng Lai, Furao Zhao, Guanglei |
author_facet | Xin, Xuan Zhang, Mengmeng Li, Xiaofeng Lai, Furao Zhao, Guanglei |
author_sort | Xin, Xuan |
collection | PubMed |
description | BACKGROUND: Flavonoid glycosides have many beneficial effects on health, but these bioactivities tend to decrease after oral administration owing to their poor lipophilicity. In this study, a facile whole-cell-based method was developed for selective preparation of monoester or diester of troxerutin, a flavonoid derivative. In addition, the bioavailabilities and antioxidant properties of troxerutin and its acylated derivatives were also investigated in cells. RESULTS: Pseudomonas aeruginosa and Pseudomonas stutzeri cells showed high catalytic efficiency (substrate conversion > 90%) and different preferences for troxerutin, resulting in the production of its monoester (TME) and diester (TDE), respectively. The logP values of troxerutin, TME, and TDE were − 2.04 ± 0.10, − 0.75 ± 0.08, and 1.51 ± 0.05 and their P(app) values were 0.34 × 10(−6) ± 0.05, 0.99 × 10(−6) ± 0.12, and 1.54 × 10(−6) ± 0.17 cm/s, respectively. The results of hydroxyl radical, ABTS, and ORAC assays indicated that the antiradical activities of acylated derivatives did not exceed that of troxerutin, but showed higher inhibition effects upon 2,2′-azobis(2-amidinopropane) dihydrochloride-induced erythrocyte hemolysis than that of troxerutin (P < 0.05). CONCLUSION: A facile and efficient whole-cell biocatalysis method was developed to synthesize troxerutin-acylated derivatives, markedly enhancing the bioavailability and antioxidant activities of troxerutin in cells. Additionally, the mechanism underlying the observed difference in the antioxidant activities of troxerutin and its esters was ascribed to both their free radical scavenging abilities and distribution on the cell membrane surface. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s12934-018-0976-x) contains supplementary material, which is available to authorized users. |
format | Online Article Text |
id | pubmed-6106897 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | BioMed Central |
record_format | MEDLINE/PubMed |
spelling | pubmed-61068972018-08-29 Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro Xin, Xuan Zhang, Mengmeng Li, Xiaofeng Lai, Furao Zhao, Guanglei Microb Cell Fact Research BACKGROUND: Flavonoid glycosides have many beneficial effects on health, but these bioactivities tend to decrease after oral administration owing to their poor lipophilicity. In this study, a facile whole-cell-based method was developed for selective preparation of monoester or diester of troxerutin, a flavonoid derivative. In addition, the bioavailabilities and antioxidant properties of troxerutin and its acylated derivatives were also investigated in cells. RESULTS: Pseudomonas aeruginosa and Pseudomonas stutzeri cells showed high catalytic efficiency (substrate conversion > 90%) and different preferences for troxerutin, resulting in the production of its monoester (TME) and diester (TDE), respectively. The logP values of troxerutin, TME, and TDE were − 2.04 ± 0.10, − 0.75 ± 0.08, and 1.51 ± 0.05 and their P(app) values were 0.34 × 10(−6) ± 0.05, 0.99 × 10(−6) ± 0.12, and 1.54 × 10(−6) ± 0.17 cm/s, respectively. The results of hydroxyl radical, ABTS, and ORAC assays indicated that the antiradical activities of acylated derivatives did not exceed that of troxerutin, but showed higher inhibition effects upon 2,2′-azobis(2-amidinopropane) dihydrochloride-induced erythrocyte hemolysis than that of troxerutin (P < 0.05). CONCLUSION: A facile and efficient whole-cell biocatalysis method was developed to synthesize troxerutin-acylated derivatives, markedly enhancing the bioavailability and antioxidant activities of troxerutin in cells. Additionally, the mechanism underlying the observed difference in the antioxidant activities of troxerutin and its esters was ascribed to both their free radical scavenging abilities and distribution on the cell membrane surface. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1186/s12934-018-0976-x) contains supplementary material, which is available to authorized users. BioMed Central 2018-08-22 /pmc/articles/PMC6106897/ /pubmed/30134913 http://dx.doi.org/10.1186/s12934-018-0976-x Text en © The Author(s) 2018 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated. |
spellingShingle | Research Xin, Xuan Zhang, Mengmeng Li, Xiaofeng Lai, Furao Zhao, Guanglei Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro |
title | Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro |
title_full | Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro |
title_fullStr | Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro |
title_full_unstemmed | Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro |
title_short | Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro |
title_sort | biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro |
topic | Research |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6106897/ https://www.ncbi.nlm.nih.gov/pubmed/30134913 http://dx.doi.org/10.1186/s12934-018-0976-x |
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