title: Synthesis of two new hydroxylated derivatives of spironolactone by microbial transformation.
abstract: Spironolactone is a medicinally important molecule that is clinically used in the treatment and management of many diseases such as oedema and ascites in cirrhosis of the liver, malignant ascites, nephrotic syndrome, chronic lung disease, resistant hypertension, congestive heart failure, and primary hyperaldosteronism. Microbial transformations of spironolactone by Cunninghamella elegans ATCC 9245 was carried out. Two new hydroxylated derivatives, 12β-hydroxy-spironolactone and 2α-hydroxy-spironolactone, were synthesized. Their structures were characterized on the basis of the spectroscopic data. The substrate can be efficiently converted into the products within 72 h after its addition to the fermentation broth of C. elegans ATCC 9245.
authors.affiliation: Department of Biological Engineering, Utah State University, 4105 Old Main Hill, Logan, UT 84322, United States; College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, Zhejiang 310032, China.
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Mei
authors.affiliation: Department of Biological Engineering, Utah State University, 4105 Old Main Hill, Logan, UT 84322, United States.
authors.forename: Luoyi
authors.initials: L
authors.lastname: Wang
authors.affiliation: Department of Biological Engineering, Utah State University, 4105 Old Main Hill, Logan, UT 84322, United States.
authors.forename: Siyuan
authors.initials: S
authors.lastname: Wang
authors.affiliation: Department of Biological Engineering, Utah State University, 4105 Old Main Hill, Logan, UT 84322, United States. Electronic address: jixun.zhan@usu.edu.
authors.forename: Jixun
authors.initials: J
authors.lastname: Zhan
mesh_terms: D000818:Animals; D020093:Cunninghamella / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D005285:Fermentation; D006900:Hydroxylation; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D013148:Spironolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D013148:Spironolactone
keywords: Biotransformation; Cunninghamella elegans; Selective hydroxylation; Spironolactone