Synthesizing a Berberine Derivative and Evaluating Antimicrobial Activity To Reinforce with Students the Potential Significance of Small Chemical Structure Changes for Biological Systems,Journal of Chemical Education

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Synthesizing a Berberine Derivative and Evaluating Antimicrobial Activity To Reinforce with Students the Potential Significance of Small Chemical Structure Changes for Biological Systems
Journal of Chemical Education ( IF 2.5 ) Pub Date : 2018-01-30 00:00:00 , DOI: 10.1021/acs.jchemed.7b00458
Catarina A. B. Rodrigues ₁ , Iris Neto ₂ , Patricia Rijo _{1,

2} , Carlos A. M. Afonso ₁

Affiliation

The convenient synthesis of dihydroberberine by the reduction of berberine is described as an experiment for an upper-division undergraduate organic chemistry laboratory course. Students obtained up to 74% yield of the desired pure product without the use of chromatographic techniques. The antimicrobial activities of both compounds against Staphylococcus aureus and Candida albicans were then assessed and compared in an upper-division undergraduate microbiology laboratory course. The students verified that berberine shows higher antimicrobial activity than its derivative dihydroberberine, demonstrating that small changes in a chemical structure can result in great biological differences.

中文翻译：

合成小Ber碱衍生物并评估抗菌活性，以增强学生对生物系统小的化学结构变化的潜在意义

通过还原小ber碱方便地合成二氢小ber碱被描述为高等本科有机化学实验室课程的实验。学生无需使用色谱技术即可获得所需纯产品的最高74％的收率。然后评估了这两种化合物对金黄色葡萄球菌和白色念珠菌的抗菌活性，并在高等本科生微生物实验室课程中进行了比较。学生们证实小碱比其衍生的二氢小ber碱显示出更高的抗菌活性，表明化学结构的微小变化会导致巨大的生物学差异。

更新日期：2018-01-30

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