Mechanistic aspects of the biogenesis of rose oxide in Pelargonium graveolens L'Héritier
✍ Scribed by Matthias Wüst; Annette Rexroth; Thomas Beck; Armin Mosandl
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 184 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
Mechanistic aspects of the biogenesis of the chiral monoterpenoid rose oxide in Pelargonium graveolens L'He ´ritier are investigated using deuterium-labelled precursors. After administration of the precursors using the cut-stem method, the dynamic headspace extracts of the plants are analysed using multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS). It is unequivocally shown that this plant is able to convert citronellol and menthocitronellol into cis-/trans-rose oxide. Menthocitronellol is converted into rose oxide with a clearly detectable enantiodiscrimination. These facts may be explained with the presence of an oxidase, which is able to oxidize citronellol and menthocitronellol in allylic position. A photooxygenation mechanism including singlet oxygen as the oxidizing agent is rather unlikely.