Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability
Catechin and epicatechin are the health beneficial flavan-3-ols in tea and many fruits. However, their extreme hydrophilicity renders drawbacks for them to pass through the bio-membranes. We prepared lipophilic flavan-3-ol derivatives by acetylation or by acetone-conjugation. The structures of these...
Main Authors: | , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
Elsevier
2015-01-01
|
Series: | Journal of Functional Foods |
Subjects: | |
Online Access: | http://www.sciencedirect.com/science/article/pii/S1756464614003685 |
id |
doaj-01e4abfc4a044c7cb11bba53bf795485 |
---|---|
record_format |
Article |
spelling |
doaj-01e4abfc4a044c7cb11bba53bf7954852021-04-29T04:43:23ZengElsevierJournal of Functional Foods1756-46462015-01-0112256261Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration abilityHao-Cong Meng0Jie Gao1Hua-Chuan Zheng2Alatangaole Damirin3Chao-Mei Ma4College of Life Sciences, Inner Mongolia University, Huhhot, Inner Mongolia, ChinaCollege of Life Sciences, Inner Mongolia University, Huhhot, Inner Mongolia, ChinaCancer Research Center, Liaoning Medical University, Jinzhou, Liaoning, 121001, ChinaCollege of Life Sciences, Inner Mongolia University, Huhhot, Inner Mongolia, ChinaCollege of Life Sciences, Inner Mongolia University, Huhhot, Inner Mongolia, China; Corresponding author. College of Life Sciences, Inner Mongolia University, Huhhot, Inner Mongolia, China. Tel.: +86 471 4992435; fax: +86 471 4992435.Catechin and epicatechin are the health beneficial flavan-3-ols in tea and many fruits. However, their extreme hydrophilicity renders drawbacks for them to pass through the bio-membranes. We prepared lipophilic flavan-3-ol derivatives by acetylation or by acetone-conjugation. The structures of these derivatives were determined based on their NMR and MS spectra. The 3,5- and 3,7-diacetyl derivatives showed radical scavenging activity slightly weaker than catechin and epicatechin, but showed significantly enhanced capacity to penetrate into living cells. Moreover, the diacetyl derivatives released flavan-3-ols inside cells, while catechin or epicatechin themselves could not penetrate into the cells. The acetone conjugates showed strong antioxidant activity and were able to enter into living cells in the intact form. The acetylated and acetone-conjugated derivatives protected H2O2-induced erythrocyte hemolysis more effectively than catechin and epicatechin. These results indicated that acetylated and acetone-conjugated flavan-3-ols are promising compounds with less hydrophilicity and better bioactivities in biological systems.http://www.sciencedirect.com/science/article/pii/S1756464614003685Flavan-3-olsLow-polar derivative3,5-O-diacetylcatechin3,5-O-diacetylepicatechinLiving cell penetration |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Hao-Cong Meng Jie Gao Hua-Chuan Zheng Alatangaole Damirin Chao-Mei Ma |
spellingShingle |
Hao-Cong Meng Jie Gao Hua-Chuan Zheng Alatangaole Damirin Chao-Mei Ma Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability Journal of Functional Foods Flavan-3-ols Low-polar derivative 3,5-O-diacetylcatechin 3,5-O-diacetylepicatechin Living cell penetration |
author_facet |
Hao-Cong Meng Jie Gao Hua-Chuan Zheng Alatangaole Damirin Chao-Mei Ma |
author_sort |
Hao-Cong Meng |
title |
Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability |
title_short |
Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability |
title_full |
Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability |
title_fullStr |
Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability |
title_full_unstemmed |
Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability |
title_sort |
diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability |
publisher |
Elsevier |
series |
Journal of Functional Foods |
issn |
1756-4646 |
publishDate |
2015-01-01 |
description |
Catechin and epicatechin are the health beneficial flavan-3-ols in tea and many fruits. However, their extreme hydrophilicity renders drawbacks for them to pass through the bio-membranes. We prepared lipophilic flavan-3-ol derivatives by acetylation or by acetone-conjugation. The structures of these derivatives were determined based on their NMR and MS spectra. The 3,5- and 3,7-diacetyl derivatives showed radical scavenging activity slightly weaker than catechin and epicatechin, but showed significantly enhanced capacity to penetrate into living cells. Moreover, the diacetyl derivatives released flavan-3-ols inside cells, while catechin or epicatechin themselves could not penetrate into the cells. The acetone conjugates showed strong antioxidant activity and were able to enter into living cells in the intact form. The acetylated and acetone-conjugated derivatives protected H2O2-induced erythrocyte hemolysis more effectively than catechin and epicatechin. These results indicated that acetylated and acetone-conjugated flavan-3-ols are promising compounds with less hydrophilicity and better bioactivities in biological systems. |
topic |
Flavan-3-ols Low-polar derivative 3,5-O-diacetylcatechin 3,5-O-diacetylepicatechin Living cell penetration |
url |
http://www.sciencedirect.com/science/article/pii/S1756464614003685 |
work_keys_str_mv |
AT haocongmeng diacetylatedandacetoneconjugatedflavan3olsaspotentantioxidantswithcellpenetrationability AT jiegao diacetylatedandacetoneconjugatedflavan3olsaspotentantioxidantswithcellpenetrationability AT huachuanzheng diacetylatedandacetoneconjugatedflavan3olsaspotentantioxidantswithcellpenetrationability AT alatangaoledamirin diacetylatedandacetoneconjugatedflavan3olsaspotentantioxidantswithcellpenetrationability AT chaomeima diacetylatedandacetoneconjugatedflavan3olsaspotentantioxidantswithcellpenetrationability |
_version_ |
1721501809698144256 |