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Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities
Enzymatic conjugation with fatty acids including omega-3 polyunsaturated fatty acids (ω-3 PUFAs) derived from fish oil to three citrus fruit-derived flavonoids: grapefruit extract, naringin, and neohesperidin dihydrochalcone were investigated. The conversions were achieved over 85% under the catalys...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5673637/ https://www.ncbi.nlm.nih.gov/pubmed/29163154 http://dx.doi.org/10.3389/fphar.2017.00759 |
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author | Sun, Cynthia Q. Johnson, Keryn D. Wong, Herbert Foo, L. Y. |
author_facet | Sun, Cynthia Q. Johnson, Keryn D. Wong, Herbert Foo, L. Y. |
author_sort | Sun, Cynthia Q. |
collection | PubMed |
description | Enzymatic conjugation with fatty acids including omega-3 polyunsaturated fatty acids (ω-3 PUFAs) derived from fish oil to three citrus fruit-derived flavonoids: grapefruit extract, naringin, and neohesperidin dihydrochalcone were investigated. The conversions were achieved over 85% under the catalysis of lipase Novozyme 435 in acetone at 45°C at semi-preparative scale. The conjugates were purified via solvent partition and silica gel chromatography and achieved 90–98% in purity. The NMR analysis of the conjugates confirmed that the fatty acid carbon chain was linked onto the primary –OH group on the glucose moiety of the flavonoids. The purified flavonoid conjugates alongside their original flavonoids were analyzed for antioxidant activities via 2,2-diphenyl-1-picrylhydrazyl scavenging assay, and anti-peroxidation test via peroxide values measured during a 1-week fish oil storage trial. Vascular endothelial growth factor (VEGF) assay was conducted with 1, 10, and 100 μM of naringin and grapefruits and their conjugates, respectively, and total VEGF levels were measured at 24 and 48 h, respectively, using ELISA and dot blot analysis. The results from these functionality experiments demonstrated that flavonoid FA conjugates have at least comparable (if not higher) antioxidant activity, anti-peroxidation activity, and anti-angiogenic activity. |
format | Online Article Text |
id | pubmed-5673637 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-56736372017-11-21 Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities Sun, Cynthia Q. Johnson, Keryn D. Wong, Herbert Foo, L. Y. Front Pharmacol Pharmacology Enzymatic conjugation with fatty acids including omega-3 polyunsaturated fatty acids (ω-3 PUFAs) derived from fish oil to three citrus fruit-derived flavonoids: grapefruit extract, naringin, and neohesperidin dihydrochalcone were investigated. The conversions were achieved over 85% under the catalysis of lipase Novozyme 435 in acetone at 45°C at semi-preparative scale. The conjugates were purified via solvent partition and silica gel chromatography and achieved 90–98% in purity. The NMR analysis of the conjugates confirmed that the fatty acid carbon chain was linked onto the primary –OH group on the glucose moiety of the flavonoids. The purified flavonoid conjugates alongside their original flavonoids were analyzed for antioxidant activities via 2,2-diphenyl-1-picrylhydrazyl scavenging assay, and anti-peroxidation test via peroxide values measured during a 1-week fish oil storage trial. Vascular endothelial growth factor (VEGF) assay was conducted with 1, 10, and 100 μM of naringin and grapefruits and their conjugates, respectively, and total VEGF levels were measured at 24 and 48 h, respectively, using ELISA and dot blot analysis. The results from these functionality experiments demonstrated that flavonoid FA conjugates have at least comparable (if not higher) antioxidant activity, anti-peroxidation activity, and anti-angiogenic activity. Frontiers Media S.A. 2017-11-02 /pmc/articles/PMC5673637/ /pubmed/29163154 http://dx.doi.org/10.3389/fphar.2017.00759 Text en Copyright © 2017 Sun, Johnson, Wong and Foo. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Pharmacology Sun, Cynthia Q. Johnson, Keryn D. Wong, Herbert Foo, L. Y. Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities |
title | Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities |
title_full | Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities |
title_fullStr | Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities |
title_full_unstemmed | Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities |
title_short | Biotransformation of Flavonoid Conjugates with Fatty Acids and Evaluations of Their Functionalities |
title_sort | biotransformation of flavonoid conjugates with fatty acids and evaluations of their functionalities |
topic | Pharmacology |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5673637/ https://www.ncbi.nlm.nih.gov/pubmed/29163154 http://dx.doi.org/10.3389/fphar.2017.00759 |
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