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）测量脂质体中掺入的量以确定异黄素的亲脂性。在异类黄酮结构中B环的4'位置在A形环的5位和甲氧基的5位存在羟基的存在增加了掺入的量。通过使用V79细胞的集型形成测定法研究了异黄素的细胞毒性。细胞毒性活性的结构活性关系反映了掺入的量。（2）（+） - 儿茶素衍生物的抗菌活性随烷基链长度的伸长而增加。具有三个或更多碳链的衍生物对脂质体膜表现出很强的亲和力。链条超过五碳的衍生物破坏了膜。这些结果暗示，（+） - 儿茶素衍生物对脂质体膜的破坏和破坏能力参与其抗菌活性。（3）酚酸，咖啡酸，P-coumaric Acid和Ferulic Acid的抗氧化效应，通过对O_2的摄入进行HAR-_2的抗氧化作用。 Metmyoglobin。酚酸的主要抗氧化作用归因于pH 7.4时渡轮甲蛋白的减少，并抑制第二阶段胶束内发生的链反应在pH 3.4的胶束内。固态 ^<31> p和 ^2h nmr。 DMPC磷酸组的 ^<31> P化学移位各向异性在添加EGCG时降低。 DMPC脂质体中[4- ^2H] EGCG的 ^2H NMR光谱给出的氘核的四核分裂比固相中的四倍分裂要小得多。这些观察结果提供了直接的实验证据，表明EGCG分子与脂质双层相互作用。

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）

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

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）。