Chirality and biosynthesis of lilac compounds in Actinidia arguta flowers
- 作者：A.J. Matich ; B.J. Bunn ; D.J. Comeskey ; M.B. Hunt ; D.D. Rowan
- 关键词：Actinidia arguta ; Monoterpenes ; Linalool ; 8-Hydroxylinalool ; 8-Oxolinalool ; Lilac aldehydes ; Lilac alcohols ; Lilac alcohol epoxides ; Deuterium labelling ; Enantioselective GC-MS
- 刊名：Phytochemistry
- 出版年：2007
- 期刊代码：85_00319422
- 类别：ch
- 出版时间：July 2007
- 卷：68
- 期：13
- 页码：1746-1751
- 文件大小：322 K
摘要
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.