Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro
Abstract 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 tr...
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| Format: | Article |
| Language: | English |
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BMC
2018-08-01
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| Series: | Microbial Cell Factories |
| Subjects: | |
| Online Access: | http://link.springer.com/article/10.1186/s12934-018-0976-x |
| _version_ | 1828260739739025408 |
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| author | Xuan Xin Mengmeng Zhang Xiaofeng Li Furao Lai Guanglei Zhao |
| author_facet | Xuan Xin Mengmeng Zhang Xiaofeng Li Furao Lai Guanglei Zhao |
| author_sort | Xuan Xin |
| collection | DOAJ |
| description | Abstract 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. |
| first_indexed | 2024-04-13T03:27:39Z |
| format | Article |
| id | doaj.art-d0076d642720409b806ad6d9fd88a8a9 |
| institution | Directory Open Access Journal |
| issn | 1475-2859 |
| language | English |
| last_indexed | 2024-04-13T03:27:39Z |
| publishDate | 2018-08-01 |
| publisher | BMC |
| record_format | Article |
| series | Microbial Cell Factories |
| spelling | doaj.art-d0076d642720409b806ad6d9fd88a8a92022-12-22T03:04:37ZengBMCMicrobial Cell Factories1475-28592018-08-0117111110.1186/s12934-018-0976-xBiocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitroXuan Xin0Mengmeng Zhang1Xiaofeng Li2Furao Lai3Guanglei Zhao4School of Food Science and Engineering, South China University of TechnologySchool of Food Science and Engineering, South China University of TechnologySchool of Food Science and Engineering, South China University of TechnologySchool of Food Science and Engineering, South China University of TechnologyState Key Laboratory of Pulp and Paper Engineering, South China University of TechnologyAbstract 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.http://link.springer.com/article/10.1186/s12934-018-0976-xTroxerutinPropionyl derivativesWhole-cell biocatalysisBioavailabilityAntioxidant activity |
| spellingShingle | Xuan Xin Mengmeng Zhang Xiaofeng Li Furao Lai Guanglei Zhao Biocatalytic synthesis of acylated derivatives of troxerutin: their bioavailability and antioxidant properties in vitro Microbial Cell Factories Troxerutin Propionyl derivatives Whole-cell biocatalysis Bioavailability Antioxidant activity |
| 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 | Troxerutin Propionyl derivatives Whole-cell biocatalysis Bioavailability Antioxidant activity |
| url | http://link.springer.com/article/10.1186/s12934-018-0976-x |
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