Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Steroids. 2010 Jul;75(7):506-12. doi: 10.1016/j.steroids.2010.03.007. Epub 2010 Mar 30.
Synthesis, aggregation behavior and in vitro cholesterol solubilization studies of 16-epi-pythocholic acid (3 alpha,12 alpha,16 beta-trihydroxy-5 beta-cholan-24-oic acid, EPCA) are reported. The synthesis of this unnatural epimer of pythocholic acid (3 alpha,12 alpha,16 alpha-trihydroxy-5 beta-cholan-24-oic acid, PCA) involves a series of simple and selective chemical transformations with an overall yield of 21% starting from readily available cholic acid (CA). The critical micellar concentration (CMC) of 16-epi-pythocholate in aqueous media was determined using pyrene as a fluorescent probe. In vitro cholesterol solubilization ability was evaluated using anhydrous cholesterol and results were compared with those of other natural di- and trihydroxy bile acids. These studies showed that 16-epi-pythocholic acid (16 beta-hydroxy-deoxycholic acid) behaves similar to cholic acid (CA) and avicholic acid (3 alpha,7 alpha,16 alpha-trihydroxy-5 beta-cholan-24-oic acid, ACA) in its aggregation behavior and cholesterol dissolution properties.
报道了 16-epi-胆酸（3α，12α，16β-三羟基-5β-胆烷-24-酸，EPCA）的合成、聚集行为及体外胆固醇增溶研究。这种天然胆酸（3α，12α，16α-三羟基-5β-胆烷-24-酸，PCA）的非对映异构体 16-epi-胆酸的合成涉及一系列简单而选择性的化学转化，总收率为 21%，起始原料为易得的胆酸（CA）。使用芘作为荧光探针，在水介质中测定了 16-epi-胆酸盐的临界胶束浓度（CMC）。使用无水胆固醇评价了体外胆固醇增溶能力，并将结果与其他天然二羟基和三羟基胆酸进行了比较。这些研究表明，16-epi-胆酸（16β-羟基去氧胆酸）在聚集行为和胆固醇溶解性质上与胆酸（CA）和鹅去氧胆酸（3α，7α，16α-三羟基-5β-胆烷-24-酸，ACA）相似。
