Biotransformation of (S)-(+)-linalool by Aspergillus niger: an investigation of the culture conditions.
The biotransformation of (S)-(+)-linalool by different Aspergillus niger strains was studied, using submerged shaken liquid cultures. One strain, A. niger DSM 821, was able to convert the substrate to cis- and trans-furanoid linalool oxide (yield 30% and 5%, respectively) and cis- and trans-pyranoid linalool oxide (yield 14% and 1.5%, respectively). The main metabolites, cis-(2S,5R)-furanoid and cis-(3S,6S)-pyranoid linalool oxide, have a sweet, floral, creamy odor and are used in perfumery. The culture conditions involved, such as the composition of the broth and the type and concentration of cosolvent applied and possible adaptation to the substrate during inoculation, were investigated. It was found that (S)-(+)-linalool was converted much better than (R)-(-)-linalool and that no significant chemical conversion of the substrate occurred in control flasks at pH 3.5. Three cosolvents for improving the solubility of linalool in the culture broths were compared, namely MeOH, EtOH, and acetone. The highest bioconversion yields were obtained when the substrate was applied as a diluted solution in acetone. Screening of the fungi for their biotransformation capacity was performed by solid-phase microextraction.
Demyttenaere
J C
JC
Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium. Jan.Demyttenaere@rug.ac.be
Adams
A
A
Vanoverschelde
J
J
De Kimpe
N
N
D000080462:Acyclic Monoterpenes; D001234:Aspergillus niger / Q000254:growth & development / Q000378:metabolism*; D001711:Biotransformation; D007306:Insecticides / Q000737:chemistry / Q000493:pharmacokinetics*; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D039821:Monoterpenes; D010944:Plants; D013045:Species Specificity; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000493:pharmacokinetics*
D000080462:Acyclic Monoterpenes; D007306:Insecticides; D039821:Monoterpenes; D013729:Terpenes; C018584:linalool