Biotransformation of citronellal by Solanum aviculare suspension cultures: preparation of p-menthane-3,8-diols and determination of their absolute configurations.
Citronellal was transformed by Solanum aviculare suspension cultures to menthane-3,8-diols. cis-Menthane-3,8-diol dominated over the trans-isomer (39% and 15%, respectively). Absolute configurations of menthane-3,8-diols were assigned by critical analysis of 1H and 19F NMR spectra of prepared esters with 2-methoxy-2-phenyl-3,3,3-trifluoropropanoic acid. Citronellol and isopulegol were other products of the transformation (23% and 17%, respectively). The reaction course was identical for both citronellal enantiomers.
D000080462:Acyclic Monoterpenes; D000447:Aldehydes / Q000378:metabolism*; D001711:Biotransformation; D018929:Cell Culture Techniques; D000081005:Cyclohexane Monoterpenes; D000432:Methanol / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D039821:Monoterpenes / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular; D032322:Solanum / Q000378:metabolism*; D013237:Stereoisomerism; D013729:Terpenes / Q000378:metabolism
D000080462:Acyclic Monoterpenes; D000447:Aldehydes; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D013729:Terpenes; C409816:isopulegol; C007078:citronellol; C108217:citronellal; D000432:Methanol