Use of cyclodextrins in biotransformation reactions with cell cultures of Morus nigra: biosynthesis of prenylated chalcone isocordoin.
In vivo biotransformation experiments were performed by using a cell suspension culture of Morus nigra expressing a high PT (prenyltransferase) activity, fed with the target substrate 2',4'-dihydroxychalcone. In order to improve the reaction yields by enhancing the chalcone solubility, three different cyclodextrins have been used to host the substrate. The respective complexes have been studied by means of both spectroscopic and calorimetric techniques (Fourier-transform infrared, 1H-NMR and differential scanning calorimetry) and the solution behaviours have been characterized by solubility phase studies. The hydroxypropyl-beta-cyclodextrin complex was found to be the most suitable for biotransformation, and the reaction of prenylation resulted in a 6-fold higher yield of the final product when compared with the use of the free substrate. The reaction provided as the sole product the 3'-dimethylallyl derivative isocordoin, a biologically active plant compound. The results obtained allow the development of systems based on the use of biofermentors or the use of immobilized cells in order to enhance the biotransformation yields.
Bolasco
Adriana
A
Dip. di Chimica e Tecnologie del Farmaco, Università di Roma La Sapienza, P.le Aldo Moro, 5, 00185 Rome, Italy.
Fioravanti
Rossella
R
Rossi
Francesca
F
Rossi
Paola
P
Vitali
Alberto
A
D001711:Biotransformation; D002152:Calorimetry, Differential Scanning; D002396:Catechols / Q000302:isolation & purification / Q000378:metabolism*; D002478:Cells, Cultured; D047188:Chalcones / Q000302:isolation & purification / Q000378:metabolism*; D003505:Cyclodextrins / Q000737:chemistry / Q000378:metabolism*; D004122:Dimethylallyltranstransferase; D004355:Drug Stability; D031625:Morus / Q000254:growth & development / Q000378:metabolism*; D054876:Prenylation; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared
D002396:Catechols; D047188:Chalcones; D003505:Cyclodextrins; C438026:isocordoin; D004122:Dimethylallyltranstransferase