Structure elucidation, enantioselective analysis, and biogenesis of nerol oxide in Pelargonium species.
A novel enantioselective synthesis of nerol oxide (3, 6-dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran) was used for the determination of the absolute configuration at C-2. The order of elution of the enantiomers on octakis-(2, 3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin in OV 1701-vi as the chiral stationary phase in enantioselective GC was determined as (2R) before (2S). Enantioselective multidimensional GC/MS (enantio-MDGC/MS) was used for the determination of the enantiomeric ratios of nerol oxide in different geranium oils. As a result, in all investigated oils nerol oxide occurs as a racemate. The biogenesis of nerol oxide in Pelargonium species was investigated by feeding experiments using deuterium-labeled neryl glucoside as the precursor. The Pelargonium plants were able to convert the fed precursor into racemic nerol oxide, which has to be considered as a "natural racemate".
Wüst
M
M
Institut für Lebensmittelchemie, Biozentrum, Johann Wolfgang Goethe-Universität, Frankfurt, Germany.
Reindl
J
J
Fuchs
S
S
Beck
T
T
Mosandl
A
A
D000080462:Acyclic Monoterpenes; D008401:Gas Chromatography-Mass Spectrometry; D019684:Magnoliopsida / Q000378:metabolism*; D015394:Molecular Structure; D039821:Monoterpenes; D010938:Plant Oils / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
D000080462:Acyclic Monoterpenes; D039821:Monoterpenes; D010938:Plant Oils; D011714:Pyrans; C412910:nerol oxide