Bioorganic Chemistry ( IF 4.5 ) Pub Date : 2020-09-11 , DOI: 10.1016/j.bioorg.2020.104275 Qi-Ji Li 1 , Peng-Fei Tang 1 , Xin Zhou 1 , Wei-Jia Lu 1 , Wen-Jun Xu 1 , Jun Luo 1 , Ling-Yi Kong 1
Acylphloroglucinol meroterpenoids are adducts of the acylphloroglucinol unit and polyprenylated fragments (terpenoids) with attractive structures and bioactivities. During study of the medicinal molecules of the genus Hypericum, the first example of dimethylated acylphloroglucinol meroterpenoids with pyran-fused 6/6/6 tricyclic skeletons ((+)/(−)-elodeoidols A-F (1–6)), along with three biogenetical homologues (7–9) were isolated from the herbaceous plant of Hypericum elodeoides. Their structures including absolute configurations were then identified by nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectroscopy (HRESIMS), electronic circular dichroism (ECD) analysis and calculations. The monoterpene moiety of 1–6 were cyclized as two cyclohexanes and fused with a dimethylated acylphloroglucinol unit through an additional ether linkage, which led to an interesting pyran-fused linear or angle type 6/6/6 tricyclic skeleton. Compounds 5, 8 and 9 showed preferable antibacterial activities against three oral bacteria, among the MIC value of (+)-5 was 6.25 μg/ml; Compounds 3, 7 and 8 exhibited significant NO inhibitory activity against LPS induced RAW264.7 cells (IC50: 10.39 ± 0.49 ~ 34.25 ± 2.32 μM).
中文翻译:
具有甲基化的金丝桃属植物的抗口腔细菌和抗炎活性的二甲基化酰基间苯三酚类胡萝卜素类化合物。
酰基间苯三酚甲萜类化合物是酰基间苯三酚单元和具有有吸引力的结构和生物活性的聚异戊二烯化片段(萜类化合物)的加合物。在属的药用分子的研究金丝桃,的第一例二甲基化的酰基间苯三meroterpenoids与吡喃稠合三环6/6/6骨架((+)/( - ) - elodeoidols AF(1 - 6)),用三沿biogenetical同源物(7 - 9)从的草本植物分离金丝桃elodeoides。然后通过核磁共振(NMR),高分辨率电喷雾电离质谱(HRESIMS),电子圆二色性(ECD)分析和计算来确定其结构,包括绝对构型。的单萜部分1 - 6被环化作为两个环己烷和通过一个附加的醚键,从而导致了一个有趣的吡喃稠合的直链或角型6/6/6三环骨架与二甲基化的酰基间苯三单元稠合。化合物5,8和9显示出优选的抗菌活性对三名口腔细菌,(+)的MIC值之间- 5为6.25微克/毫升; 化合物3,78和8对LPS诱导的RAW264.7细胞表现出显着的NO抑制活性(IC 50:10.39±0.49〜34.25±2.32μM)。