Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites
Anna Gliszczyńska , Agnieszka Łysek , Tomasz Janeczko , Marta Świtalska , Joanna Wietrzyk , Czesław Wawrzeńczyk
AbstractSix metabolites were obtained as a result of microbial transformation of (+)-nootkatone (1) by the fungal strains: Botrytis, Didymosphaeria, Aspergillus, Chaetomium and Fusarium. Their structure were established as (+)-(4R,5S,7R,9R)-9α-hydroxynootkatone (2), (+)-(4R,5S,7R)-13- hydroxynootkatone (3) and (+)-(4R,5S,7R,9R,11S)-11,12-epoxy-9α- hydroxynootkatone (4), (+)-(4R,5S,7R,11S)-11,12-epoksynootkatone (5), (+)-(4R,5S,7R)-11,12-dihydroxynootkatone (6) and (+)-(4R,5S,7R)-7,11,12- trihydroxynootkatone (7) on the basis of their spectral data. Two products: (4) and (7) were not previously reported in the literature. The antiproliferative activity of (+)-nootkatone (1) and isolated metabolites (2-7) of its biotransformation has been evaluated.
|Journal series||Bioorganic & Medicinal Chemistry, [Bioorganic and Medicinal Chemistry], ISSN 0968-0896, e-ISSN 1464-3391, (A 30 pkt)|
|Publication size in sheets||0.5|
|Keywords in English||(+)-Nootkatone; Antiproliferative activity; Aspergillus niger MB; Aspergillus ochraceus; Biotransformation; Botrytis cinerea; Cancer cell lines: A549 (human lung adenocarcinoma) and HL-60 (human promyelocytic leukemia); Chaetomium sp.; Didymosphaeria igniaria; Fusarium culmorum; Sesquiterpenes|
|ASJC Classification||; ; ; ; ; ;|
|Publication indicators||= 26; = 25; : 2011 = 1.254; : 2011 = 2.921 (2) - 2011=3.157 (5)|
|Citation count*||34 (2020-08-05)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.