ABSTRACT
The structures of two previously unknown sesquiterpene alcohols of the potato (Solanum tuberosum) were assigned. The potato alcohols were obtained by steam-distillation, preparative column chromatography, and separation into fractions by HPLC on a silica gel column. The fractions were studied by GC-FID, GC-MS, and NMR spectroscopy. The potato sesquiterpene alcohols were identified as kunzeaol (6-alpha-hydroxygermacra-1(10),4-diene) and ledol. These two compounds were used in feeding tests with larvae and beetles of the Colorado potato beetle (Leptinotarsa decemlineata Say). In a bioassay, kunzeaol was found to act as a feeding attractant for the beetles.
Subject(s)
Coleoptera/physiology , Plant Leaves/chemistry , Sesquiterpenes/analysis , Solanum tuberosum/chemistry , Animals , Chromatography, High Pressure Liquid , Eating/drug effects , Pheromones , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacologyABSTRACT
The qualitative and quantitative compositions of leaf cuticular waxes from potato (Solanum tuberosum) varieties were studied. The principal components of the waxes were very long chain n-alkanes, 2-methylalkanes and 3-methylalkanes (3.1-4.6 microg cm(-2)), primary alcohols (0.3-0.7 microg cm(-2)), fatty acids (0.3-0.6 microg cm(-2)), and wax esters (0.1-0.4 microg cm(-2)). Methyl ketones, sterols, beta-amyrin, benzoic acid esters and fatty acid methyl, ethyl, isopropyl and phenylethyl esters were found for the first time in potato waxes. The qualitative composition of the waxes was quite similar but there were quantitative differences between the varieties studied. A new group of cuticular wax constituents consisting of free 2-alkanols with odd and even numbers of carbon atoms ranging from C25 to C30 was identified.
Subject(s)
Plant Leaves/chemistry , Solanum tuberosum/chemistry , Waxes/chemistry , Alcohols/chemistry , Aldehydes/chemistry , Alkanes/chemistry , Esters/chemistry , Ketones/chemistry , Time Factors , Waxes/isolation & purificationABSTRACT
A comparative study of potato leaf sesquiterpenes was carried out. GC, GC-MS, and NMR analyses were used to identify and quantify the sesquiterpenes in the leaf surfaces of 10 potato (Solanum tuberosum) varieties. Two sesquiterpene alcohols and 17 sesquiterpene hydrocarbons were identified and quantitatively determined. The distribution of the sesquiterpenes was found to be variety-specific. The sesquiterpene contents of the different potato varieties were subjected to cluster and principal component analyses. The eight potato varieties of the main chemotype cluster were dominated by beta-caryophyllene (9-148 ng/cm2), germacrene D (2-46 ng/cm2), germacrene D-4-ol (0.4-31 ng/cm2), beta-sesquiphellandrene (1-34 ng/cm2), and an unknown sesquiterpene alcohol III (0.2-37 ng/cm2). Chemometric classification distinguished two varieties, Mila and Vistula, from a major cluster. The Vistula variety was distinguished from the others by its high contents of beta-caryophyllene, alpha-humulene, germacrene D, and germacrene D-4-ol and the Mila variety by beta-elemene, trans-alpha-bergamotene, (Z)-beta-farnesene, (E)-beta-farnesene, trans-beta-bergamotene, beta-sesquiphellandrene, and unknown sesquiterpene alcohols I, II, III.
