微生物转化法制备双脱甲氧基姜黄素糖苷化产物及其对HepG2肿瘤细胞的抑制作用

The preparation of bisdemethoxycurcumin-glucoside by microbial transformation method and its inhibitory effect to HepG2 Tumor cells

双脱甲氧基姜黄素是一种具有极强抗氧化活性和抗肿瘤活性的天然酚类成分,但是极差的水溶性和稳定性制约了其在食品、医药领域的广泛应用。通过微生物转化进行结构改造,引入亲水性的葡萄糖苷键基团是有效解决其水溶性的手段。该研究利用不同微生物体系对双脱甲氧基姜黄素进行微生物转化,发现华根霉Rhizopus chinensis IFFI 3043能够将双脱甲氧基姜黄素(Bisdemethoxycurcumin,BDMC)转化为双脱甲氧基姜黄素-O-葡萄糖苷(BDMC-O-glucoside),且转化效率达到63%。研究利用高效液相色谱-质谱联合(high performance liquid chromatography-mass spectormeter,HPLC-MS)、核磁共振(nuclear magnetic resonance,NMR)等检测手段,确认了BDMC-O-glucoside转化产物的化学结构,完成了其转化过程的动态曲线分析,并通过MTT细胞毒活性法发现BDMC-O-glucoside对Hep G2肿瘤细胞的抑制作用显著强于BDMC。

Bisdemethoxycurcumin is a nature-derived phenolic compound with potent anti-oxidant and anti-tumor activities. However,the application of bisdemethoxycurcumin in food and medicine industry was restricted by its poor solubility and stability. The introduction of glucoside bond by microbial transformation method to improve the water solubility through structural transformation is an effective way. In this paper,the transformation of bisdemethoxycurcumin by different microbial strains was studied. It was found that bisdemethoxycurcumin could be transformed to bisdemethoxycurcumin-glucoside by Rhizopus chinensis IFFI 3043,and the conversion rate was up to 63%. The chemical structure of bisdemethoxycurcumin-glucoside was confirmed by HPLC-MS and NMR methods. The analysis on dynamic curve of transformation was also completed. It was also discovered that the inhibitory effect of bisdemethoxycurcumin-glucoside on HepG2 tumor cells was stronger than that of bisdemethoxycurcumin by MTT method. The microbial transformation method established in this paper could have great potential in functional food and medicine industry.