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Interaction of plant polyphenols with lipids and proteins

植物多酚与脂质和蛋白质的相互作用

基本信息

批准号：
15580110
负责人：
NAKAYAMA Tsutomu
金额：
$ 2.37万
依托单位：
University of Shizuoka
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2003
资助国家：
日本
起止时间：
2003 至 2004
项目状态：
已结题

项目摘要

(1) The amount of incorporated into liposomes was measured to determine lipophilicity of isoflavonoids. The presence of a hydroxyl group at 5-position of the A-ring and a methoxyl group at 4'-position of the B-ring in the isoflavonoid structure increased the amount incorporated. The cytotoxicity of isoflavonoids was investigated by a colony-formation assay with V79 cells. The structure-activity relationship of the cytotoxic activity reflected the amount incorporated.(2) The antibacterial activity of (+)-catechin derivatives increased with elongation of the alkyl chain length. The derivatives with a chain of three carbons or more showed strong affinity for the liposome membrane. The derivatives with chains longer than five carbons destroyed the membrane. These results implied that the lipophilicity and disrupting ability of the (+)-catechin derivatives to the liposome membrane participate in their antibacterial activity.(3) Antioxidant effects of the phenolic acids, caffeic acids, p-coumaric acid, and ferulic acid, were investigated by monitoring O_2 consumption in the linoleic acid micelles in the presence of H_2O_2 and metmyoglobin. The main antioxidant effects of the phenolic acids was ascribed to reduction of ferrylmyoglobin at pH 7.4 and inhibition of the chain reaction occurring inside of the micelles in the second phase at pH 3.4.(4) The interaction of a tea catechin, epigallocatechin gallate (EGCg), with the model membrane of dimyristoylphosphatidylcholine (DMPC) was studied by solid-state ^<31>P and ^2H NMR. The ^<31>P chemical shift anisotropy of the DMPC phosphate group decreased on addition of EGCg. The ^2H NMR spectrum of [4-^2H]EGCg in the DMPC liposomes gave deuterium nuclei with much smaller quadrupole splittings than those in the solid phase. These observations provide direct experimental evidence that the EGCg molecule interacts with the lipid bilayers.

(1)测定异黄酮入脂质体的量，测定其亲脂性。异黄酮结构中a环5位羟基和b环4′位甲氧基的存在增加了掺入量。用V79细胞集落形成实验研究了异黄酮的细胞毒性。细胞毒活性的构效关系反映了掺入量的大小。(2)(+)-儿茶素衍生物的抑菌活性随着烷基链长度的延长而增强。具有3个或更多碳链的衍生物对脂质体膜具有较强的亲和力。链长于5个碳的衍生物破坏了膜。这些结果表明(+)-儿茶素衍生物的亲脂性和对脂质体膜的破坏能力参与了它们的抗菌活性。(3)在H_2O_2和肌红蛋白存在的情况下，通过监测亚油酸胶束中O_2的消耗，考察了酚酸、咖啡酸、对香豆酸和阿威酸的抗氧化作用。酚酸的主要抗氧化作用是在pH 7.4时还原铁基肌红蛋白，在pH 3.4时抑制第二相胶束内发生的链式反应。(4)采用固态^<31>P和^2H NMR研究了茶儿茶素表没食子儿茶素没食子酸酯（EGCg）与二myristoylphosphatidycholine （DMPC）模型膜的相互作用。加入EGCg后，DMPC磷酸基团的^<31>P化学位移各向异性降低。DMPC脂质体中的[4-^2H]EGCg的^2H核磁共振谱显示氘原子核的四极分裂比固相中的四极分裂小得多。这些观察结果提供了EGCg分子与脂质双分子层相互作用的直接实验证据。

项目成果

期刊论文数量（18）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Ryuichi Kato: "Affinity of isoflavonoids for lipid bilayers evaluated with liposomal systems"BioFactors. 19・3,4. 179-187 (2003)

加藤龙一：“用脂质体系统评估异黄酮类化合物对脂质双层的亲和力”19・3,4（2003）。

DOI：
发表时间：
期刊：
影响因子：
0
作者：
通讯作者：

Advances in Planar Lipid Bilayers and Liposomes

DOI：
10.1016/b9780123965332000033
发表时间：
2012
期刊：
影响因子：
0
作者：
N. Goga;A. Rzepiela;de Melo;De Vries;A. Hadar;A. J. Markvoort;Sv Silvia Nedea;H. Berendsen
通讯作者：
N. Goga;A. Rzepiela;de Melo;De Vries;A. Hadar;A. J. Markvoort;Sv Silvia Nedea;H. Berendsen

Interaction of Plant Polyphenols with Liposomes