Odor-active alcohols from the fungal transformation of alpha-farnesene.
Submerged microbial cultures were screened for their potential to oxifunctionalize alpha-farnesene. The major oxidation product in all transforming cultures, 3,7,11-trimethyldodeca-1,3(E),5(E)10-tetraen-7-ol, showed a pleasant citrus-like odor and peak concentrations of 170 mg L-1. An Aspergillus niger isolate from mango generated another two terpene alcohols identified as diastereomeric menth-1-en-3-[2-methyl-1,3-butadienyl]-8-ol, a new natural compound with an apricot-like odor. The regiospecifity of the oxygen attack with concurrent lack of stereoselectivity suggested that the initial step of the bioconversion resembled the chemical autoxidation starting with the generation of an intermediate resonance-stabilized carbon-centered radical or carbocation.
Krings
Ulrich
U
Zentrum für Angewandte Chemie, Institut für Lebensmittelchemie, Leibniz Universität Hannover, Wunstorfer Strasse 14, D-30453 Hannover, Germany.
Hardebusch
Björn
B
Albert
Dieter
D
Berger
Ralf G
RG
Maróstica
Mario
M
Pastore
Glaucia M
GM
D000438:Alcohols / Q000378:metabolism*; D001234:Aspergillus niger / Q000378:metabolism; D001711:Biotransformation; D020171:Botrytis / Q000378:metabolism; D002597:Chaetomium / Q000378:metabolism; D006801:Humans; D003904:Mitosporic Fungi / Q000378:metabolism*; D009812:Odorants; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000378:metabolism*
D000438:Alcohols; D012717:Sesquiterpenes; C062672:alpha-farnesene