Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability
Diacetylated and acetone-conjugated flavan-3-ols as potent antioxidants with cell penetration ability
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二乙酰化和丙酮结合的 flavan-3-ols 作为具有细胞渗透能力的有效抗氧化剂
DOI：
10.1016/j.jff.2014.11.018
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发表时间：
2015
影响因子：
5.6
通讯作者：
Ma Chao-Mei
中科院分区：
文献类型：
--
作者：
Meng Hao-Cong;Gao Jie;Zheng Hua-Chuan;Damirin Alatangaole;Ma Chao-Mei
儿茶素和表儿茶素是茶和许多水果中有益健康的黄烷醇。然而，它们的极端亲水性给它们通过生物膜带来了缺点。我们通过乙酰化或丙酮偶联的方法制备了亲脂性黄烷-3-醇衍生物。根据它们的核磁共振和质谱图确定了它们的结构。3，5-和3，7-双乙酰衍生物的自由基清除活性略弱于儿茶素和表儿茶素，但显著增强了穿透活细胞的能力。此外，双乙酰衍生物在细胞内释放黄烷-3-醇，而儿茶素或表儿茶素本身不能渗透到细胞内。丙酮结合物显示出很强的抗氧化活性，并且能够以完整的形式进入活细胞。乙酰化和丙酮结合的衍生物比儿茶素和表儿茶素更有效地保护过氧化氢诱导的红细胞溶血。这些结果表明，乙酰化和丙酮偶联的黄烷-3-醇是一类亲水性较差、生物活性较好的化合物。
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.
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DOI：
10.1038/nrc2641
发表时间：
2009-06
期刊：
Nature reviews. Cancer
影响因子：
--
作者：
通讯作者：
--
影响因子：
6.1
作者：
Zhong, Ying;Shahidi, Fereidoon
通讯作者：
Shahidi, Fereidoon
DOI：
10.1002/chin.199109306
发表时间：
1991-03
期刊：
ChemInform
影响因子：
--
作者：
J. V. D. Westhuizen;J. A. Steenkamp;D. Ferreira
通讯作者：
J. V. D. Westhuizen;J. A. Steenkamp;D. Ferreira
影响因子：
2.1
作者：
J. V. D. Westhuizen;J. A. Steenkamp;D. Ferreira
通讯作者：
J. V. D. Westhuizen;J. A. Steenkamp;D. Ferreira
影响因子：
6.1
作者：
F. Paiva‐Martins;Aníbal Silva;V. Almeida;M. Carvalheira;C. Serra;José Enrique Rodrígues-Borges;J. Fernandes;L. Belo;A. Santos-Silva
通讯作者：
F. Paiva‐Martins;Aníbal Silva;V. Almeida;M. Carvalheira;C. Serra;José Enrique Rodrígues-Borges;J. Fernandes;L. Belo;A. Santos-Silva