Regio- and stereoselective oxidation of (+)-Delta(3)-carene by the larvae of common cutworm (Spodoptera litura).
Biotransformation of (+)-Delta(3)-carene (1) and (+)-(1S,3S,4R,6R)-3,4-epoxycarane (1-1) by larvae of Spodoptera litura was investigated. Compound 1 was transformed to (+)-(1S,3S,4R,6R,7S)-3,4-epoxycaran-9-ol (1-2) by S. litura. This structure was established by infrared, electron impact-mass spectrometry, one- and two-dimensional NMR spectral studies, and (+)-(1S,3S,4R,6R)-3,4-epoxycarane (1-1) was transformed for confirmation of a metabolic pathway. The results indicate that the metabolic reaction of compound 1 by the larvae of S. litura was regioselective hydroxylation at the methyl group of the geminal dimethyl (C-9 position) followed by stereoselective epoxidation at the carbon-carbon double bands (C-3 position). (+)-(1S,3S,4R,6R,7S)-3,4-Epoxycaran-9-ol (1-2) was a new compound.
Miyazawa
Mitsuo
M
Faculty of Science and Engineering, Department of Applied Chemistry, Kinki University, Higasiosaka-shi, Osaka, Japan. miyazawa@apch.kindai.ac.jp
Kano
Haruki
H
D000818:Animals; D000081008:Bicyclic Monoterpenes; D001711:Biotransformation; D001643:Bridged Bicyclo Compounds / Q000737:chemistry* / Q000378:metabolism*; D007814:Larva / Q000378:metabolism; D010084:Oxidation-Reduction; D018411:Spodoptera / Q000378:metabolism*; D013237:Stereoisomerism
D000081008:Bicyclic Monoterpenes; D001643:Bridged Bicyclo Compounds; C030218:3-carene