Su Bao-Ning, Jung Park Eun, Vigo Jose Schunke, Graham James G, Cabieses Fernando, Fong Harry H S, Pezzuto John M, Kinghorn A Douglas
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Phytochemistry. 2003 Jun;63(3):335-41. doi: 10.1016/s0031-9422(03)00112-2.
Activity-guided fractionation of an EtOAc-soluble extract of the leaves of Muntingia calabura collected in Peru, using an in vitro quinone reductase induction assay with cultured Hepa 1c1c7 (mouse hepatoma) cells, resulted in the isolation of a flavanone with an unsubstituted B-ring, (2R,3R)-7-methoxy-3,5,8-trihydroxyflavanone (5), as well as 24 known compounds, which were mainly flavanones and flavones. The structure including absolute stereochemistry of compound 5 was determined by spectroscopic (HRMS, 1D and 2D NMR, and CD spectra) methods. Of the isolates obtained, in addition to 5, (2S)-5-hydroxy-7-methoxyflavanone, 2',4'-dihydroxychalcone, 4,2',4'-trihydroxychalcone, 7-hydroxyisoflavone and 7,3',4'-trimethoxyisoflavone were found to induce quinone reductase activity.
利用培养的Hepa 1c1c7（小鼠肝癌）细胞进行体外醌还原酶诱导试验，对在秘鲁采集的刺篱木叶的乙酸乙酯可溶提取物进行活性导向分级分离，得到了一种B环未被取代的黄烷酮，即(2R,3R)-7-甲氧基-3,5,8-三羟基黄烷酮（5），以及24种已知化合物，主要为黄烷酮和黄酮。化合物5的结构包括绝对立体化学通过光谱方法（高分辨质谱、一维和二维核磁共振以及圆二色谱）确定。在所得到的分离物中，除了5之外，还发现(2S)-5-羟基-7-甲氧基黄烷酮、2',4'-二羟基查耳酮、4,2',4'-三羟基查耳酮、7-羟基异黄酮和7,3',4'-三甲氧基异黄酮可诱导醌还原酶活性。
