Biogenetic Studies in Syringa vulgaris L.: Synthesis and Bioconversion of Deuterium-Labeled Precursors into Lilac Aldehydes and Lilac Alcohols

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• 作者：Mirjam Kreck ; Susen Pü ; schel ; Matthias Wü ; st ; and Armin Mosandl
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2003
• 出版时间：January 15, 2003
• 年：2003
• 卷：51
• 期：2
• 页码：463 - 469
• 全文大小：180K
• 年卷期：v.51,no.2(January 15, 2003)
• ISSN：1520-5118

文摘

Syringa vulgaris L. inflorescences were fed with aqueous solutions of regioselectively deuteratedcompounds assumed to be precursors of lilac aldehyde and lilac alcohol, respectively. Volatiles wereextracted by stir bar sorptive extraction (SBSE) and analyzed using enantioselective multidimensionalgas chromatography/mass spectrometry (enantio-MDGC/MS); deuterium-labeled lilac aldehydes andlilac alcohols were separated from unlabeled stereoisomers on a fused silica capillary column, coatedwith heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)--cyclodextrin (DIME--CD) (30%) in SE 52(70%), as the chiral stationary phase. Feeding experiments with [5,5-²H₂]mevalonic acid lactone 22and [5,5-²H₂]deoxy-D-xylose 23 indicate that the novel mevalonate independent 1-deoxy-D-xylose5-phosphate/2C-methyl-D-erythritol 4-phosphate pathway is the dominant metabolic route for biosynthesis in lilac flowers. Additionally, bioconversion of deuterium-labeled d₅-(R/S)-linalool 3, d₆-(R)-linalool 21, d₅-(R/S)-8-hydroxylinalool 6, d₅-(R/S)-8-oxolinalool 7, d₅-lilac aldehydes 8-11 andd₅-lilac alcohols 12-15 into lilac during in vivo feeding experiments was investigated and the metabolicpathway is discussed. Incubation of petals with an aqueous solution of deuterated d₅-(R/S)-linalool3 indicates an autonomic terpene biosynthesis of lilac flavor compounds in the flower petals of lilac.Keywords: Syringa vulgaris L. biosynthesis; stir bar sorptive extraction (SBSE); enantioselectivemultidimensional gas chromatography/mass spectrometry (enantio-MDGC/MS); deuterium-labeled monoterpenes