Journal of Natural Medicines ( IF 3.3 ) Pub Date : 2022-10-26 , DOI: 10.1007/s11418-022-01657-8 Yuki Yoshino 1 , Naonobu Tanaka 1 , Daisuke Tsuji 1, 2 , Kohji Itoh 1 , Yoshiki Kashiwada 1
Three new farnesylated coumarins, communiferulins A–C (1–3), and a farnesylated chromone, ferchromone (4), were isolated from the roots of an Apiaceous plant Ferula communis. Their structures including the relative configurations were elucidated by a combination of spectroscopic analyses and calculations of the NMR data. Communiferulins A–C (1–3) had dihydrofuran rings fused to C-3 and C-4 of their coumarin moieties, while 3 possessed one additional furan ring. HPLC analyses using a chiral column showed 1–4 to be racemates, and the absolute configurations of (+)-1, (–)-1, (+)-2, and (–)-2 were deduced by comparison of their ECD spectra with TDDFT-calculated spectra. Communiferulins A (1) and B (2), and ferchromone (4) showed inhibitory activities on IL-1β production from LPS-stimulated microglial cells.
中文翻译:
来自阿魏根的Communiferulins、farnesylated 香豆素及其抗神经炎症活性
从伞形科植物阿魏的根部分离出三种新的法尼基化香豆素、communiferulins A–C ( 1–3 )和一种法尼基化色酮铁色酮 ( 4 ) 。它们的结构(包括相对构型)通过光谱分析和核磁共振数据计算的组合得到阐明。Communiferulins A–C ( 1 – 3 ) 具有与其香豆素部分的 C-3 和 C-4 融合的二氢呋喃环,而3具有一个额外的呋喃环。使用手性柱的 HPLC 分析显示1 – 4是外消旋体,(+)- 1 , (–)-的绝对构型1、(+)- 2和 (–)- 2是通过将它们的 ECD 光谱与 TDDFT 计算的光谱进行比较推导出来的。Communiferulins A ( 1 ) 和 B ( 2 ) 以及铁色酮 ( 4 ) 显示出对 LPS 刺激的小神经胶质细胞产生 IL-1β 的抑制活性。