Ahn Jongmin, Chae Hee-Sung, Chin Young-Won, Kim Jinwoong
College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul 08826, Korea.
College of Pharmacy and Integrated Research Institute for Drug Development, Dongguk University-Seoul, Gyeonggi-do 10326, Korea.
Molecules. 2017 Jul 8;22(7):1138. doi: 10.3390/molecules22071138.
Dereplication allows for a rapid identification of known and unknown compounds in plant extracts. In this study, we performed liquid chromatography-mass spectroscopy (LC-MS)- based dereplication using data from ESI⁺ QTOF-MS for the analysis of phenylpropanoid-substituted diglycosides, the major active constituents of (C. A. Mey.) Beck. Using TOF-MS alone, the substructures of these compounds could be unambiguously confirmed based on the characteristic fragmentation patterns of various product ions. HPLC-MS based profiling of also allowed for the detection of new phenylpropanoid-substituted diglycosides from this plant. Of them, five new phenylpropanoid-substituted diglycosides, named cistansalsides A-E (, , , and ), were isolated. Their structures were elucidated through spectroscopic methods including NMR and MS analysis. All the isolates were tested for their inhibitory activity against NO production in RAW 264.7 cells stimulated by LPS. Of the tested compounds, compounds , , and showed moderate inhibitory activity on inducible NO synthase. Compounds , and also inhibited the phosphorylation of NF-κB in macrophages. None of the compounds displayed significant cytotoxicity.
去重复化有助于快速鉴定植物提取物中的已知和未知化合物。在本研究中,我们使用电喷雾电离正离子模式飞行时间质谱(ESI⁺ QTOF-MS)数据,基于液相色谱 - 质谱联用(LC-MS)对苯丙烷取代双糖苷进行去重复化分析,苯丙烷取代双糖苷是白花紫露草(Tradescantia albiflora (C. A. Mey.) Beck.)的主要活性成分。仅使用飞行时间质谱(TOF-MS),基于各种产物离子的特征性裂解模式,就可以明确确认这些化合物的亚结构。基于高效液相色谱 - 质谱联用(HPLC-MS)对白花紫露草的分析,还能够检测到该植物中的新型苯丙烷取代双糖苷。其中,分离出了五种新型苯丙烷取代双糖苷,命名为白花紫露草苷A - E(cistansalsides A - E)(化合物1、2、3、4和5)。通过包括核磁共振(NMR)和质谱(MS)分析在内的光谱方法阐明了它们的结构。对所有分离物进行了测试,以检测其对脂多糖(LPS)刺激的RAW 264.7细胞中一氧化氮(NO)产生的抑制活性。在测试的化合物中,化合物1、2、3和4对诱导型一氧化氮合酶表现出中等抑制活性。化合物2、3和5还抑制巨噬细胞中核因子κB(NF - κB)的磷酸化。所有化合物均未表现出明显的细胞毒性。