百里香daenensisCelak(唇科),被称为德纳安百里香,是一种伊朗特有植物,通常用于其驱风剂,祛痰药,抗菌和抗真菌特性。先前的研究报告了T.daenensis地上部分精油的化学特征,但对其非挥发性成分知之甚少。在这里,已经完成了对T.daenensis地上部分的极地提取物的植物化学和生物学研究,以进一步了解该植物的传统用途。进行MeOH提取物的高效液相色谱与线性离子阱和轨道阱高分辨率质谱(LC-ESI/LTQOrbitrap/MS/MS)分析,以指导特殊代谢物的分离和通过NMR分析的连续表征。MeOH提取物显示通过DPPH(EC50=48.99±1.47μg/mL)和TEAC测定(1.37mg/mL)评估的抗氧化活性。相继,提取物和分离化合物对大肠杆菌成熟生物膜的生物膜抑制活性,铜绿假单胞菌,鲍曼不动杆菌,单核细胞增生李斯特菌,和金黄色葡萄球菌,并评价了它们对无柄细菌细胞代谢的影响。已经鉴定了两种以前未报道的百里酚衍生物。分离的化合物的生物膜抑制活性突出了对测试化合物的有希望的抗微生物作用。特别是,香草酸,(3S,5R,6R,7E,9S)-megastigm-7-烯-3,5,6,9-四醇3-O-β-D-吡喃葡萄糖苷,胸腺嘧啶喹啉-2-O-β-D-吡喃葡萄糖苷和从未报道过的化合物daenol能够对所有病原菌产生抑制活性。在10μg/mL浓度下测试的所有化合物均以37.7%至77.39%的百分比抑制大肠杆菌的固着细胞的代谢,和单核细胞增生李斯特菌的百分比在21.79%和71.17%之间。
Thymus daenensis Celak (Lamiaceae family), known as denaian thyme, is an Iranian endemic plant, commonly used for its carminative, expectorant, antibacterial and antifungal properties. Previous studies report the chemical profile of the essential oil of T. daenensis aerial parts, but little is known about its non volatile constituents. Herein, phytochemical and biological investigation of the polar extract of T. daenensis aerial parts to provide further insight into traditional use of this plant has been accomplished. High-performance liquid chromatography coupled to linear ion-trap and orbitrap high-resolution mass spectrometry (LC-ESI/LTQOrbitrap/MS/MS) analysis of MeOH extract was performed to guide the isolation of specialized metabolites and successive characterization by NMR analysis. MeOH extract displayed antioxidant activity evaluated by DPPH (EC50 = 48.99 ± 1.47 μg/mL) and TEAC assay (1.37 mg/mL). Successively, the biofilm inhibitory activity of extract and isolated compounds against mature biofilms of Escherichia coli, Pseudomonas aeruginosa, Acinetobacter baumannii, Listeria monocytogenes, and Staphylococcus aureus, and their influence on the metabolism of sessile bacterial cells were evaluated. Two previously unreported thymol derivatives have been identified. The biofilm inhibitory activity of isolated compounds highlighted a promising antimicrobial action for the tested compounds. In particular, vanillic acid, (3S,5R,6R,7E,9S)-megastigm-7-ene-3,5,6,9-tetrol 3-O-β-D-glucopyranoside, thymoquinol-2-O-β-D-glucopyranoside and the never reported compound daenol resulted capable of exerting inhibitory activity vs all pathogenic strains. All compounds tested at a concentration of 10 μg/mL inhibited the metabolism of the sessile cells of E. coli at a percentage ranging between 37.7% and 77.39%, and of L.monocytogenes at a percentage ranging between 21.79% and 71.17%.