Metabolism of monoterpenes: specificity of the dehydrogenases responsible for the biosynthesis of camphor, 3-thujone, and 3-isothujone.
Sage (Salvia officinalis) is shown to contain two electrophoretically distinct dehydrogenases for the respective oxidations of (+)-borneol to (+)-camphor, and of (+)-cis-sabinol to (+)-sabinone en route to (-)-3-isothujone. Similarly, tansy (Tanacetum vulgare) is shown to contain two electrophoretically distinct dehydrogenases for the respective oxidations of (-)-borneol to (-)-camphor and of (+)-cis-sabinol to (+)-sabinone en route to (+)-3-thujone. These results demonstrate that separate dehydrogenases are responsible for the biosynthesis of camphor from borneol and of the thujyl ketones via cis-sabinol, and they also indicate that the previously reported oxidations of various thujanols by the borneol dehydrogenases are only coincidental activities not relevant to the formation of 3-thujone and 3-isothujone.
Dehal
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Institute of Biological Chemistry, Washington State University, Pullman 99164-6340.
Croteau
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D000429:Alcohol Oxidoreductases / Q000378:metabolism; D000081008:Bicyclic Monoterpenes; D002164:Camphor / Q000378:metabolism*; D002850:Chromatography, Gel; D004591:Electrophoresis, Polyacrylamide Gel; D008970:Molecular Weight; D039821:Monoterpenes; D009243:NAD / Q000494:pharmacology; D009249:NADP / Q000494:pharmacology; D010088:Oxidoreductases / Q000378:metabolism*; D010944:Plants / Q000201:enzymology*; D013729:Terpenes / Q000378:metabolism*
D000081008:Bicyclic Monoterpenes; D039821:Monoterpenes; D013729:Terpenes; D009243:NAD; D009249:NADP; D002164:Camphor; C005790:beta-thujone; D010088:Oxidoreductases; D000429:Alcohol Oxidoreductases; C053724:sabinol dehydrogenase; C053725:borneol dehydrogenase