Microbial Transformation Of Pregnane-3β,16β,20-Triol

Microbial transformation has been proven to be a useful addition to technology. Inertcarbon in a series of compounds could be catalyzed with the hydroxyl by the regioselectiveand stereo-selectivity synthesis of the technique and some complex organic reactions may beextremely specific and quickly completed. In addition, microorganisms can be used as areliable and efficient synthetic chemistry for obtaining sizable amounts of a number of drugderivativesSteroidal drugs are the second largest category of drugs only lower than antibiotics. Avariety of steroids are widely used as anti-inflammatory, diuretic, anabolic, contraceptive, andanticancer agents as well as in other applications. The effective method of direct oxidativedegradation of tigogenin into pregnane-3β,16β,20-triol has been developed. In order toconvert pregnane-3β,16β,20-triol into medicine and potentially useful organic molecules andthen applied to synthesize steroidal drugs, synthetic intermediates or natural steroids withimportant physiological activity, and further to utilize tigogenin rationally.In this article, the way which use biotransformation to modify the structure ofpregnane-3β,16β,20-triol by introducing the hydroxyl. The main contents and results areconcluded as follow:Screening scale experiments showed that Coriolus versicolor, Cunnonghamellablakesleeana, Cunnonghamella elegans and Cunnonghamella echinulata which are screenedfrom eleven microorganisms, have abilities to transform pregnane-3β,16β,20-triol into itsderivatives as determined by TLC. Cunninghamella echinulata had been selected astransforming bacteria form eleven test epiphytes and been used for a large scale liquidfermentation. Incubation of substrate pregnane-3β,16β,20-triol with Cunninghamellaechinulata yielded six major metabolites by multiple column chromatography on CC, ODS,Sephadex LH-20,et al., five of which were identified by various spectroscopic methods (1DNMR,2D NMR) in combination with HR-MS, MS and IR as pregnane-3β,14α,16β,20-tetrol(YZIII-1), pregnane-3-oxo-14α,16β,20-triol (YZIII-2), pregnane-3-oxo-7β,16β,20-triol(YZIII-3), pregnane-3β,7β,16β,20-tetrol (YZIV-4), and pregnane-3β,5,16β,20-tetrol (YZIV-5).These five metabolites were also new bioconversion products.