Structure-Activity and Lipophilicity Relationships of Selected Antibacterial Natural Flavones and Flavanones of Chilean Flora.
Structure-Activity and Lipophilicity Relationships of Selected Antibacterial Natural Flavones and Flavanones of Chilean Flora.
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DOI：
10.3390/molecules22040608
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发表时间：
2017-04-10
期刊：
影响因子：
--
通讯作者：
Wilkens M
中科院分区：
文献类型：
--
作者：
Echeverría J;Opazo J;Mendoza L;Urzúa A;Wilkens M
在这项研究中，我们测试了八种天然存在的类黄酮——三种黄酮和五种黄酮——对四种革兰氏阳性和四种革兰氏阴性细菌可能的抗菌性能。黄酮类化合物以其抗菌特性和结构多样性而闻名；这些植物源性化合物是研究潜在新型抗菌机制的良好模型。亲脂性和抗菌化合物与细胞膜的相互作用决定了其成功或失败的目标。因此，通过非极性/水相分配系数的测定、亲脂性的估计以及不同黄酮类化合物、黄酮类化合物和黄酮类化合物的抗菌活性的量化，评估了这些参数之间的关系。活性类黄酮的扩散系数在9.4 × 10−10 ~ 12.3 × 10−10 m2/s之间，亲脂性在2.0 ~ 3.3之间。黄酮类化合物对革兰氏阴性菌的亲脂性值范围较窄，而对革兰氏阳性菌的亲脂性和细胞裂解性范围较广。高良姜是活性最高的类黄酮，其结构特征是在A环上有两个羟基，而在b环上没有极性基团。一个羟基的甲基化会降低3- o -甲基高良姜的活性，两个羟基的甲基化会导致失活，如3,7- o -二甲基高良姜。综上所述，黄酮类化合物的两亲性对其抗菌活性起着至关重要的作用。在这些化合物中，亲水和疏水部分必须存在，并且可以通过亲脂性分析来预测。
In this study, we tested eight naturally-occurring flavonoids—three flavanones and five flavones—for their possible antibacterial properties against four Gram-positive and four Gram-negative bacteria. Flavonoids are known for their antimicrobial properties, and due their structural diversity; these plant-derived compounds are a good model to study potential novel antibacterial mechanisms. The lipophilicity and the interaction of antibacterial compounds with the cell membrane define the success or failure to access its target. Therefore, through the determination of partition coefficients in a non-polar/aqueous phase, lipophilicity estimation and the quantification of the antibacterial activity of different flavonoids, flavanones, and flavones, a relationship between these parameters was assessed. Active flavonoids presented diffusion coefficients between 9.4 × 10−10 and 12.3 × 10−10 m2/s and lipophilicity range between 2.0 to 3.3. Active flavonoids against Gram-negative bacteria showed a narrower range of lipophilicity values, compared to active flavonoids against Gram-positive bacteria, which showed a wide range of lipophilicity and cell lysis. Galangin was the most active flavonoid, whose structural features are the presence of two hydroxyl groups located strategically on ring A and the absence of polar groups on ring B. Methylation of one hydroxyl group decreases the activity in 3-O-methylgalangin, and methylation of both hydroxyl groups caused inactivation, as shown for 3,7-O-dimethylgalangin. In conclusion, the amphipathic features of flavonoids play a crucial role in the antibacterial activity. In these compounds, hydrophilic and hydrophobic moieties must be present and could be predicted by lipophilicity analysis.
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DOI：
10.1085/jgp.75.4.427
发表时间：
1980-04
期刊：
The Journal of general physiology
影响因子：
--
作者：
Orbach E;Finkelstein A
通讯作者：
Finkelstein A
影响因子：
--
作者：
Peng C;Wang X;Chen J;Jiao R;Wang L;Li YM;Zuo Y;Liu Y;Lei L;Ma KY;Huang Y;Chen ZY
通讯作者：
Chen ZY
影响因子：
3.2
作者：
Masaoka, Y;Ueno, Y;Tsuchiya, T
通讯作者：
Tsuchiya, T
影响因子：
3.8
作者：
LAKS, PE;PRUNER, MS
通讯作者：
PRUNER, MS
影响因子：
1.6
作者：
Mendoza, L;Urzua, A
通讯作者：
Urzua, A