Unraveling the Enantiomeric Distribution of Glycosidically Bound Linalool in Teas (Camellia sinensis) and Their Acidolysis Characteristics and Pyrolysis Mechanism

芳樟醇 化学 香叶醇 乙酸芳樟酯 尼禄 山茶 对映体 有机化学 风味 质谱法 色谱法 精油 食品科学 植物 生物
作者
Han Yan,Zhiyuan Lin,Weixuan Li,Jianjian Gao,Pengliang Li,Qincao Chen,Haipeng Lv,Yue Zhang,Weidong Dai,Zhi Lin,Yin Zhu
出处
期刊:Journal of Agricultural and Food Chemistry [American Chemical Society]
标识
DOI:10.1021/acs.jafc.4c00037
摘要

Glycosidically bound linalool plays important roles in the formation of excellent tea flavor, while their enantiomeric distribution in teas and the actual transformations with free linalool are still unclear. In this study, a novel chiral ultrahigh performance liquid chromatography–mass spectrometry/mass spectrometry approach to directly analyze linalyl-β-primeveroside and linalyl-β-d-glucopyranoside enantiomers in teas was established and then applied in 30 tea samples. A close transformation relationship existed between the two states of linalool for their consistent dominant configurations (most S-form) and corresponding distribution trend in most teas (r up to 0.81). The acidolysis characterization indicated that free linalool might be slowly released from linalyl-β-primeveroside with stable enantiomeric ratios during long-term withering of white tea in a weakly acidic environment, along with other isomerized products, e.g., geraniol, nerol, α-terpineol, etc. Furthermore, a novel online thermal desorption-gas chromatography–mass spectrometry approach was established to simulate the pyrolysis releasing of linalyl-β-primeveroside during tea processing. Interestingly, free linalool was not the selected pyrolysis product of linalyl-β-primeveroside but rather trans/cis-2,6-dimethyl-2,6-octadiene during the high-fire roasting or baking step of oolong and green teas. The identification of above high-fire chemical marks presented great potential to scientifically evaluate the proper thermal conditions in the practical production of tea.
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