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Use of cyclodextrins in biotransformation reactions with cell cultures of Morus nigra : biosynthesis of prenylated chalcone isocordoin
Author(s) -
Bolasco Adriana,
Fioravanti Rossella,
Rossi Francesca,
Rossi Paola,
Vitali Alberto
Publication year - 2010
Publication title -
biotechnology and applied biochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 70
eISSN - 1470-8744
pISSN - 0885-4513
DOI - 10.1042/ba20100046
Subject(s) - biotransformation , chalcone , chemistry , prenyltransferase , substrate (aquarium) , solubility , prenylation , organic chemistry , stereochemistry , yield (engineering) , biosynthesis , combinatorial chemistry , enzyme , biology , materials science , ecology , metallurgy
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, 1 H‐NMR and differential scanning calorimetry) and the solution behaviours have been characterized by solubility phase studies. The hydroxypropyl‐β‐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.