Synthesis and Antimicrobial Evaluation of Side-Chain Derivatives based on Eurotiumide A
Synthesis and Antimicrobial Evaluation of Side-Chain Derivatives based on Eurotiumide A
复制标题
DOI：
10.3390/md18020092
复制
发表时间：
2020-01
期刊：
影响因子：
5.4
通讯作者：
A. Nakayama;Hideo Sato;Tenta Nakamura;M. Hamada;Shuji Nagano;Shuhei Kameyama;Yui Furue;Naoki Hayashi;G. Kamoshida;Sangita Karanjit;M. Oda;K. Namba
中科院分区：
文献类型：
--
作者：
A. Nakayama;Hideo Sato;Tenta Nakamura;M. Hamada;Shuji Nagano;Shuhei Kameyama;Yui Furue;Naoki Hayashi;G. Kamoshida;Sangita Karanjit;M. Oda;K. Namba
合成了二氢异色满型天然产物铕硫酰胺A的侧链衍生物，并对其抗菌活性进行了研究。以铕硫菌胺A的关键中间体为原料，合成了16个衍生物，并对2种革兰氏阳性菌（耐甲氧西林和敏感的金黄色葡萄球菌）和1种革兰氏阴性菌（牙龈卟啉单胞菌）进行了抗菌活性评价。结果表明，在其芳环上具有碘原子而不是异戊二烯基部分的衍生物对MSSA和牙龈卟啉单胞菌的抗微生物活性优于铕硫酰胺A。此外，我们发现具有异戊基侧链的衍生物，其是铕硫酰胺A的氢化产物，是针对所有三种菌株（包括MRSA）的最强抗菌剂。
Side-chain derivatives of eurotiumide A, a dihydroisochroman-type natural product, have been synthesized and their antimicrobial activities described. Sixteen derivatives were synthesized from a key intermediate of the total synthesis of eurotiumide A, and their antimicrobial activities against two Gram-positive bacteria, methicillin-susceptible and methicillin-resistant Staphylococcus aureus (MSSA and MRSA), and a Gram-negative bacterium, Porphyromonas gingivalis, were evaluated. The results showed that derivatives having an iodine atom on their aromatic ring instead of the prenyl moiety displayed better antimicrobial activity than eurotiumide A against MSSA and P. gingivalis. Moreover, we discovered that a derivative with an isopentyl side chain, which is a hydrogenated product of eurotiumide A, is the strongest antimicrobial agent against all three strains, including MRSA.