Department of Pharmaceutical Engineering, Institute of Biomolecule Reconstruction, Sun Moon University, Asan, 336-708, Korea.
Mol Cells. 2013 Oct;36(4):355-61. doi: 10.1007/s10059-013-0164-0. Epub 2013 Oct 22.
Apigenin, a member of the flavone subclass of flavonoids, has long been considered to have various biological activities. Its glucosides, in particular, have been reported to have higher water solubility, increased chemical stability, and enhanced biological activities. Here, the synthesis of apigenin glucosides by the in vitro glucosylation reaction was successfully performed using a UDP-glucosyltransferase YjiC, from Bacillus licheniformis DSM 13. The glucosylation has been confirmed at the phenolic groups of C-4' and C-7 positions ensuing apigenin 4'-O-glucoside, apigenin 7-O-glucoside and apigenin 4',7-O-diglucoside as the products leaving the C-5 position unglucosylated. The position of glucosylation and the chemical structures of glucosides were elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The parameters such as pH, UDP glucose concentration and time of incubation were also analyzed during this study.
芹菜素是类黄酮中黄酮类化合物的一个成员,长期以来一直被认为具有多种生物活性。特别是它的糖苷,据报道具有更高的水溶性、增强的化学稳定性和增强的生物活性。在这里,成功地使用来自地衣芽孢杆菌 DSM 13 的 UDP-葡萄糖基转移酶 YjiC 通过体外葡萄糖基化反应合成了芹菜素糖苷。葡萄糖基化已在 C-4'和 C-7 位置的酚羟基上得到证实,生成的产物为芹菜素 4'-O-葡萄糖苷、芹菜素 7-O-葡萄糖苷和芹菜素 4',7-O-二葡萄糖苷,C-5 位未发生葡萄糖基化。葡萄糖基化的位置和糖苷的化学结构通过液相色谱/质谱和核磁共振波谱进行了阐明。在这项研究中还分析了 pH、UDP 葡萄糖浓度和孵育时间等参数。