Biosynthesis of the sesquiterpene germacrene D in Solidago canadensis: 13C and (2)H labeling studies |
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Authors: | Steliopoulos Panagiotis Wüst Matthias Adam Klaus-Peter Mosandl Armin |
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Affiliation: | Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universit?t Frankfurt (Main), Marie-Curie-Str. 9, D-60439 Frankfurt (Main), Germany. |
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Abstract: | The biogenetic origin of the isoprenoid building blocks of the sesquiterpene germacrene D was studied in Solidago canadensis. Feeding experiments were carried out with 1-[5,5-D(2)]deoxy-D-xylulose-5-phosphate (D(2)-DOXP), [5-13C]mevalonolactone (13C-MVL) and [1-13C]-D-glucose. The hydrodistillate of a cut shoot fed with D(2)-DOXP was investigated by enantio-MDGC-MS and the volatile fraction of a shoot supplied with 13C-MVL was examined by GC-C-IRMS. The incorporation of [1-13C]-D-glucose was analyzed by quantitative 13C NMR spectroscopy after isolation of germacrene D from the essential oil. Our labeling studies revealed that the biosynthesis of the C-15 skeleton of sesquiterpene germacrene D in Solidago canadensis proceeds predominantly via the methylerythritol phosphate pathway. |
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Keywords: | Solidago canadensis Asteraceae Biosynthesis Methylerythritol phosphate pathway Sesquiterpenes Germacrene D Labeling studies |
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