title: Metabolism of monoterpenes: lactonization of (+)-camphor and conversion of the corresponding hydroxy acid to the glucoside-glucose ester in sage (Salvia officinalis).
abstract: The bicyclic monoterpene ketone (+)-camphor is a major constituent (up to 26%) of the volatile oil of immature sage (Salvia officinalis L.) leaves; however, as the plant matures the content of this ketone declines in the fully expanded leaves (to about 65% of maximum) as does the overall yield of oil (to roughly 60% of maximum). Examination of the metabolism of (+)-[G-3H]camphor in discs prepared from mature leaves of flowering sage plants revealed that this ketone was converted to a water-soluble metabolite which on chromatographic analysis proved to be considerably more polar than a simple monoterpenyl glycoside. Mass spectral analysis of several derivatives of the terpenoid moiety of the metabolite obtained from large-scale incubations allowed identification of the aglycone, while degradative studies and detailed radiochromatographic analyses indicated that the metabolite contained two glucose residues; one glycosidically linked and the other in ester linkage. All of the evidence was consistent with the initial lactonization of camphor to 1,2-campholide followed by conversion to the beta-D-glucoside-6-O-glucose ester of the corresponding hydroxy acid (1-carboxymethyl-3-hydroxy-2,2,3-trimethyl cyclopentane). Direct evidence for the intermediacy of 1,2-campholide was also obtained through isotopic dilution experiments and by direct testing of the labeled lactone. The lactonization of camphor in sage resembles a similar step in the catabolism of camphor by microorganisms, but appears to be the first report of this reaction type in higher plants.
mesh_terms: D002164:Camphor / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D005947:Glucose / Q000378:metabolism; D005960:Glucosides / Q000096:biosynthesis; D007783:Lactones / Q000378:metabolism*; D009822:Oils, Volatile / Q000378:metabolism; D010944:Plants / Q000378:metabolism*; D013729:Terpenes / Q000378:metabolism*
chemical_list: D005960:Glucosides; D007783:Lactones; D009822:Oils, Volatile; D013729:Terpenes; D002164:Camphor; C040289:1-carboxymethyl-3-hydroxy-2,2,3-trimethylcyclopentane; D005947:Glucose