Biosynthesis of the sesquiterpene germacrene D in Solidago canadensis: 13C and (2)H labeling studies.
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.
Steliopoulos
Panagiotis
P
Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universität Frankfurt (Main), Marie-Curie-Str. 9, D-60439 Frankfurt (Main), Germany.
Wüst
Matthias
M
Adam
Klaus-Peter
KP
Mosandl
Armin
A
D019659:Asteraceae / Q000737:chemistry / Q000378:metabolism*; D002247:Carbon Isotopes; D003903:Deuterium; D013058:Mass Spectrometry; D015394:Molecular Structure; D018520:Plant Shoots / Q000737:chemistry / Q000378:metabolism; D012717:Sesquiterpenes / Q000378:metabolism*; D045788:Sesquiterpenes, Germacrane; D013194:Staining and Labeling
D002247:Carbon Isotopes; D012717:Sesquiterpenes; D045788:Sesquiterpenes, Germacrane; D003903:Deuterium; C027259:germacrene D