Luan Fang, Hampel Daniela, Mosandl Armin, Wüst Matthias
Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universität Frankfurt am Main, Marie-Curie-Strasse 9, D-60439 Frankfurt (Main), Germany.
J Agric Food Chem. 2004 Apr 7;52(7):2036-41. doi: 10.1021/jf030701q.
The enantiomeric ratios of various free and glycosidically bound monoterpene polyols in musts of the aromatic grapes Vitis vinifera L. cvs. Morio Muscat and Muscat Ottonel were determined by means of enantioselective multidimensional gas chromatography-mass spectrometry. Reference compounds of defined stereochemistry were synthesized and permitted the unequivocal determination of the elution order of the target compounds on chiral columns with modified cyclodextrins as stationary phases. It could be shown for the first time that the linalool-derived polyol 3,7-dimethylocta-1,7-dien-3,6-diol occurs predominately as the (3S,6S)-configured stereoisomer, providing evidence that this compound is generated by an enzymatic process in grape berries. The involvement of a cytochrome P450 monooxygenase in the oxidative metabolism of monoterpenes in grapes is dicussed.
采用对映体选择性多维气相色谱-质谱联用技术，测定了芳香型葡萄品种欧亚种葡萄（Vitis vinifera L.）莫利麝香（Morio Muscat）和奥托内尔麝香（Muscat Ottonel）葡萄汁中各种游离和糖苷结合态单萜多元醇的对映体比例。合成了具有特定立体化学结构的参考化合物，从而能够明确目标化合物在手性柱上以改性环糊精为固定相时的洗脱顺序。首次发现，芳樟醇衍生的多元醇3,7-二甲基辛-1,7-二烯-3,6-二醇主要以(3S,6S)构型的立体异构体形式存在，这证明该化合物是在葡萄浆果中通过酶促过程生成的。本文还讨论了细胞色素P450单加氧酶在葡萄单萜氧化代谢中的作用。
