(+)-6,8-bis(1-methylthiobutyl)catechin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (+)-6,8-bis(1-methylthiobutyl)catechin
• 英文别名: (2R,3S)-2-(3,4-dihydroxyphenyl)-6,8-bis(1-methylsulfanylbutyl)-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₂₅H₃₄O₆S₂
• 分子量: 494.673
• InChiKey: VHCJIZWAMJGWNE-GRQARGJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  161
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  正丁醛 、 儿茶提取物 、 sodium thiomethoxide 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以71.5%的产率得到(+)-6,8-bis(1-methylthiobutyl)catechin
  参考文献：
  名称：

  Relationship between Antibacterial Activity of (+)-Catechin Derivatives and Their Interaction with a Model Membrane

  摘要：

  从(+)-表儿茶素和各种直链烷基醛在甲硫醇存在下合成了具有不同烷基链长度的(+)-表儿茶素衍生物，并评估了它们对革兰氏阳性菌的抗菌活性。随着衍生物烷基链长度的增加，抗菌活性明显增强，并在链长为四个至七个碳时达到最大值。随后，利用脂质体研究了(+)-表儿茶素衍生物与模型膜的作用。发现具有三个或更多碳链的衍生物对膜表现出非常强的亲和力。通过将钙黄绿素包裹在脂质体中作为荧光指示剂，研究了衍生物对膜的损伤作用。观察到具有四个或更多碳链的衍生物导致荧光泄漏。特别是具有五个以上碳链的衍生物被认为能够破坏脂质体膜，从荧光泄漏的程度可以判断。这些结果表明，(+)-表儿茶素衍生物对脂质体膜的亲脂性和破坏能力参与了它们的抗菌活性。

  DOI：

  10.1021/jf0350111

文献信息

• Relationship between Antibacterial Activity of (+)-Catechin Derivatives and Their Interaction with a Model Membrane
  作者：Katsuko Kajiya、Hiroshi Hojo、Masayuki Suzuki、Fumio Nanjo、Shigenori Kumazawa、Tsutomu Nakayama

  DOI：10.1021/jf0350111

  日期：2004.3.1

  (+)-Catechin derivatives with different alkyl chain lengths were synthesized from (+)-catechin and various straight chain alkylaldehydes in the presence of methyl mercaptan, and their antibacterial activities against Gram-positive bacteria were evaluated. The antibacterial activity increased markedly with elongation of the alkyl chain lengths of the derivatives and reached a maximum at a chain of four to seven carbons. Subsequently, interaction of the (+)-catechin derivatives with a model membrane using liposome was investigated. The derivatives with a chain of three carbons or more were found to have very strong affinity for the membrane. The injury action of the derivatives against the membrane was examined with liposome in which calcein was enclosed as a fluorescent indicator. The leakage was observed in the derivatives with chain lengths of four carbons or more. Particularly the derivatives with chains longer than five carbons are considered to destroy the liposome membrane judging from the degree of the fluorescent leakage. These results implied that the lipophilicity and disrupting ability of the (+)-catechin derivatives to the liposome membrane participate in their antibacterial activity.

  从(+)-表儿茶素和各种直链烷基醛在甲硫醇存在下合成了具有不同烷基链长度的(+)-表儿茶素衍生物，并评估了它们对革兰氏阳性菌的抗菌活性。随着衍生物烷基链长度的增加，抗菌活性明显增强，并在链长为四个至七个碳时达到最大值。随后，利用脂质体研究了(+)-表儿茶素衍生物与模型膜的作用。发现具有三个或更多碳链的衍生物对膜表现出非常强的亲和力。通过将钙黄绿素包裹在脂质体中作为荧光指示剂，研究了衍生物对膜的损伤作用。观察到具有四个或更多碳链的衍生物导致荧光泄漏。特别是具有五个以上碳链的衍生物被认为能够破坏脂质体膜，从荧光泄漏的程度可以判断。这些结果表明，(+)-表儿茶素衍生物对脂质体膜的亲脂性和破坏能力参与了它们的抗菌活性。