Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate
(–)-Epigallocatechin gallate (EGCG), the predominant catechin (≥50%) in green tea (Camellia sinensis), displays several bioactive properties but its stability and bioavailability are low. In this work, the properties of two α-glucosyl derivatives of EGCG (3′- and 7-O-α-D-glucopyranoside), obtained b...
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| Format: | Article |
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Frontiers Media S.A.
2019-03-01
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| Series: | Frontiers in Nutrition |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fnut.2019.00030/full |
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| author | Jose L. Gonzalez-Alfonso Pablo Peñalver Antonio O. Ballesteros Juan C. Morales Francisco J. Plou |
| author_facet | Jose L. Gonzalez-Alfonso Pablo Peñalver Antonio O. Ballesteros Juan C. Morales Francisco J. Plou |
| author_sort | Jose L. Gonzalez-Alfonso |
| collection | DOAJ |
| description | (–)-Epigallocatechin gallate (EGCG), the predominant catechin (≥50%) in green tea (Camellia sinensis), displays several bioactive properties but its stability and bioavailability are low. In this work, the properties of two α-glucosyl derivatives of EGCG (3′- and 7-O-α-D-glucopyranoside), obtained by enzymatic synthesis, were assessed. The α-glucosylation enhanced the pH and thermal stability of EGCG. The analysis of scavenging activity toward ABTS·+ radicals showed that the α-glucosylation at C-7 of A-ring caused a higher loss of antioxidant activity compared with the sugar conjugation at C-3′ of B-ring. The 3′-glucoside also showed higher potential to alleviate intracellular reactive oxygen species (ROS) levels and to boost REDOX activity. The toxicity of EGCG and its monoglucosides was tested in human SH-S5Y5 neurons, RAW 264.7 macrophages, MRC5 fibroblasts, and HT-29 colon cancer cells. Interestingly, the 3′-O-α-D-glucoside increased the viability of neural cells in vitro (2.75-fold at 100 μM) in the presence of H2O2, whilst EGCG gave rise only to a 1.7-fold enhancement. In conclusion, the α-glucoside of EGCG at C-3′ has a great potential for nutraceutical, cosmetic and biomedical applications. |
| first_indexed | 2024-12-20T17:02:09Z |
| format | Article |
| id | doaj.art-5a2891f7a1ae43caafecd46027d28256 |
| institution | Directory Open Access Journal |
| issn | 2296-861X |
| language | English |
| last_indexed | 2024-12-20T17:02:09Z |
| publishDate | 2019-03-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Nutrition |
| spelling | doaj.art-5a2891f7a1ae43caafecd46027d282562022-12-21T19:32:29ZengFrontiers Media S.A.Frontiers in Nutrition2296-861X2019-03-01610.3389/fnut.2019.00030436471Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin GallateJose L. Gonzalez-Alfonso0Pablo Peñalver1Antonio O. Ballesteros2Juan C. Morales3Francisco J. Plou4Instituto de Catálisis y Petroleoquímica, CSIC, Madrid, SpainInstituto de Parasitología y Biomedicina López–Neyra, CSIC, Granada, SpainInstituto de Catálisis y Petroleoquímica, CSIC, Madrid, SpainInstituto de Parasitología y Biomedicina López–Neyra, CSIC, Granada, SpainInstituto de Catálisis y Petroleoquímica, CSIC, Madrid, Spain(–)-Epigallocatechin gallate (EGCG), the predominant catechin (≥50%) in green tea (Camellia sinensis), displays several bioactive properties but its stability and bioavailability are low. In this work, the properties of two α-glucosyl derivatives of EGCG (3′- and 7-O-α-D-glucopyranoside), obtained by enzymatic synthesis, were assessed. The α-glucosylation enhanced the pH and thermal stability of EGCG. The analysis of scavenging activity toward ABTS·+ radicals showed that the α-glucosylation at C-7 of A-ring caused a higher loss of antioxidant activity compared with the sugar conjugation at C-3′ of B-ring. The 3′-glucoside also showed higher potential to alleviate intracellular reactive oxygen species (ROS) levels and to boost REDOX activity. The toxicity of EGCG and its monoglucosides was tested in human SH-S5Y5 neurons, RAW 264.7 macrophages, MRC5 fibroblasts, and HT-29 colon cancer cells. Interestingly, the 3′-O-α-D-glucoside increased the viability of neural cells in vitro (2.75-fold at 100 μM) in the presence of H2O2, whilst EGCG gave rise only to a 1.7-fold enhancement. In conclusion, the α-glucoside of EGCG at C-3′ has a great potential for nutraceutical, cosmetic and biomedical applications.https://www.frontiersin.org/article/10.3389/fnut.2019.00030/fullglycosylationtea polyphenolsantioxidantscatechinsneuroprotective properties |
| spellingShingle | Jose L. Gonzalez-Alfonso Pablo Peñalver Antonio O. Ballesteros Juan C. Morales Francisco J. Plou Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate Frontiers in Nutrition glycosylation tea polyphenols antioxidants catechins neuroprotective properties |
| title | Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate |
| title_full | Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate |
| title_fullStr | Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate |
| title_full_unstemmed | Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate |
| title_short | Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate |
| title_sort | effect of α glucosylation on the stability antioxidant properties toxicity and neuroprotective activity of epigallocatechin gallate |
| topic | glycosylation tea polyphenols antioxidants catechins neuroprotective properties |
| url | https://www.frontiersin.org/article/10.3389/fnut.2019.00030/full |
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