Microbial transformations of chalcones to produce food sweetener derivatives
Tomasz Janeczko , Witold Gładkowski , Edyta Kostrzewa-Susłow
AbstractBiotransformations of two substrates: chalcone (1) and 2′-hydroxychalcone (4) were carried out using four yeast strains and five filamentous fungi cultures. Substrate 1 was effectively hydrogenated in all of tested yeast cultures (80–99% of substrate conversion after 1 h of biotransformation) affording dihydrochalcone 2. In the cultures of filamentous fungi the reaction was much slower, however, Chaetomium sp. gave product 2 in 97% yield. After 12 h of incubation a reduction of dihydrochalcone 2 to alcohol 3 was additionally observed. After 3 days of biotransformation in the culture of Rhodotorula rubra product (S)-3 was obtained with 75% ee (enantiomeric excess) and 99% of conversion. Also after a 3-day biotransformation using the strain Fusarium culmorum product (R)-3 was obtained with 98% ee and 97% of conversion. In most of the tested strains a change in enantiomeric excess of compound 3 during the biotransformation process was noticed. In the culture of Rhodotorula glutinis after 3 h of transformation alcohol (R)-3 was formed with 47% ee and 31% of substrate conversion, whereas after 6 days the (S)-3 enantiomer was obtained with 99% ee and 91% of conversion. In the case of 2′-hydroxychalcone (4), the hydrogenation proceeded much slower and led to 2′-hydroxydihydrochalcone (5) – in the culture of Yarrowia lipolytica 97% of conversion was observed after 3 days. In all cultures of the tested strains no products of 2′-hydroxydihydrochalcone reduction were detected.
|Journal series||Journal of Molecular Catalysis B-Enzymatic, ISSN 1381-1177, (A 30 pkt)|
|Publication size in sheets||0.5|
|Keywords in English||Chalcones; Biotransformation; Chemoselective hydrogenation; Enantiospecific reduction; Yarrowia lipolytica|
|ASJC Classification||; ; ;|
|Score|| = 30.0, 18-06-2020, ArticleFromJournal|
= 30.0, 18-06-2020, ArticleFromJournal
|Publication indicators||= 20; = 20; : 2013 = 1.378; : 2013 = 2.745 (2) - 2013=2.786 (5)|
|Citation count*||26 (2020-09-28)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.