Chirality and biosynthesis of lilac compounds in Actinidia arguta flowers
| Autor: | Adam J. Matich, Daryl D. Rowan, D. Comeskey, Martin B. Hunt, Barry J. Bunn |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
Acyclic Monoterpenes
Monoterpene Actinidia Epoxide Alcohol Flowers Plant Science Horticulture Biochemistry Aldehyde Gas Chromatography-Mass Spectrometry chemistry.chemical_compound Linalool Actinidia arguta Organic chemistry Molecular Biology Actinidia deliciosa chemistry.chemical_classification Aldehydes Molecular Structure biology lilac Stereoisomerism General Medicine Deuterium biology.organism_classification chemistry Alcohols Monoterpenes |
| Zdroj: | Phytochemistry. 68:1746-1751 |
| ISSN: | 0031-9422 |
| DOI: | 10.1016/j.phytochem.2007.03.023 |
| Popis: | Biosynthesis of lilac compounds in ‘Hortgem Tahi’ kiwifruit (Actinidia arguta) flowers was investigated by treating inflorescences with d5-linalool. The incorporation of the deuterium label into 8-hydroxylinalool, 8-oxolinalool, the lilac aldehydes, alcohols, and alcohol epoxides was followed by GC-MS and enantioselective GC-MS. Both (R)- and (S)-linalool were produced naturally by the flowers, but 8-hydroxylinalool, 8-oxolinalool, and the lilac aldehydes and alcohols occurred predominantly as the (S) and 5′(S)-diastereoisomers, respectively. The enantioselective step in the biosynthesis of the lilac aldehydes and alcohols was concluded to be the oxidation of linalool to (S)-8-hydroxylinalool. In contrast, the lilac alcohol epoxides had a 5′(R):(S) ratio, the same as for linalool, which suggests that either these compounds are not synthesised from the 5′(S)-configured lilac aldehydes and alcohols, or that if indeed they are, then it is by an enantioselective step that favours utilisation of the 5′(R)-configured compounds. |
| Databáze: | OpenAIRE |
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