کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1219748 1494552 2015 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آنالیزی یا شیمی تجزیه
پیش نمایش صفحه اول مقاله
Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability
چکیده انگلیسی


• Acetylated or acetone-conjugated flavan-3-ols were prepared.
• The 3, 5 or 3, 7-O-diacetyl flavan-3-ols have high cell penetration ability.
• The diacetyl flavan-3-ols released free flavan-3-ols in cells.
• Acetone conjugates of flavan-3-ols entered into cells in intact form.
• The derivatives protected oxidative hemolysis more effectively than flavan-3-ols.

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.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Functional Foods - Volume 12, January 2015, Pages 256–261
نویسندگان
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