226547-04-2Relevant academic research and scientific papers
Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites
Gliszczyńska, Anna,?ysek, Agnieszka,Janeczko, Tomasz,?witalska, Marta,Wietrzyk, Joanna,Wawrzeńczyk, Czes?aw
experimental part, p. 2464 - 2469 (2011/05/12)
Six 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.
Biotransformation of citrus aromatics nootkatone and valencene by microorganisms
Furusawa, Mai,Hashimoto, Toshihiro,Noma, Yoshiaki,Asakawa, Yoshinori
, p. 1423 - 1429 (2007/10/03)
Biotransformations of the sesquiterpene ketone nootkatone (1) from the crude drug Alpiniae Fructus and grapefruit oil, and the sesquiterpene hydrocarbon valencene (2) from Valencia orange oil were carried out with microorganisms such as Aspergillus niger, Botryosphaeria dothidea, and Fusarium culmorum to afford structurally interesting metabolites. Their stereostructures were established by a combination of high-resolution NMR spectral and X-ray crystallographic analysis and chemical reaction. Metabolic pathways of compounds 1 and 2 by A. niger are proposed.
The Preparation and Microbiological Hydroxylation of the Sesquiterpenoid Nootkatone
Arantes, Simone F.,Farooq, Afgan,Hanson, James R.
, p. 801 - 812 (2007/10/03)
The sesquiterpenoid nootkatone has been prepared from valencene by copper(I) iodide catalysed oxidation with t-butylhydroperoxide and hydroxylated at C-9 by Mucor plumbeus and Cephalosporium aphidicola.
