Cyclodextrin-facilitated bioconversion of 17 beta-estradiol by a phenoloxidase from Mucuna pruriens cell cultures.
After complexation with beta-cyclodextrin, the phenolic steroid 17 beta-estradiol could be ortho-hydroxylated into a catechol, mainly 4-hydroxyestradiol, by a phenoloxidase from in vitro grown cells of Mucuna pruriens. By complexation with beta-cyclodextrin the solubility of the steroid increased from almost insoluble to 660 microM. The bioconversion efficiency after 72 hr increased in the following order: freely suspended cells (0%), immobilized cells (1%), cell homogenate (6%), phenoloxidase preparation (40%). Mushroom tyrosinase converted 17 beta-estradiol, as a complex with beta-cyclodextrin, solely into 2-hydroxyestradiol, with a maximal yield of 30% after 6-8 hr. Uncomplexed 17 beta-estradiol was not converted at all in any of these systems.
Woerdenbag
H J
HJ
Department of Pharmacognosy, University of Groningen, The Netherlands.
Pras
N
N
Frijlink
H W
HW
Lerk
C F
CF
Malingré
T M
TM
D001711:Biotransformation; D004156:Catechol Oxidase / Q000378:metabolism*; D002396:Catechols / Q000378:metabolism; D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003505:Cyclodextrins / Q000378:metabolism*; D003912:Dextrins / Q000378:metabolism*; D004958:Estradiol / Q000378:metabolism*; D007887:Fabaceae / Q000201:enzymology*; D014442:Monophenol Monooxygenase / Q000378:metabolism*; D010946:Plants, Medicinal; D012995:Solubility; D013213:Starch / Q000378:metabolism*; D047392:beta-Cyclodextrins
D002396:Catechols; D003505:Cyclodextrins; D003912:Dextrins; D047392:beta-Cyclodextrins; D004958:Estradiol; D013213:Starch; D004156:Catechol Oxidase; D014442:Monophenol Monooxygenase; C031215:betadex