Separation, Analysis, and Degradation of Cembranoids in Flue-Cured Tobacco Leaves

IF 2.8 3区 工程技术 Q2 CHEMISTRY, ANALYTICAL
Yue Xie, Kailong Yuan, Junchen Zhu, Yonggang Zhang, Xiaobing Zhang, Hongru Feng, Yuanjiang Pan, Cuirong Sun
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引用次数: 0

Abstract

Cembranoids are significant flavor precursors found in flue-cured tobacco leaves. The degradation products can serve as important aromatic compounds. In this study, 16 cembranoids were discovered in flue-cured tobacco leaves by liquid chromatography–mass spectrometry (MS), and 1 cembranoid featuring both oxidation and dehydrogenation from α/β-cembranoid was identified for the first time. α- and β-cembranoids were confirmed to be precursors to various degradation products. Additionally, β-cembranoid was prone to epimerize into α-cembranoid while simultaneously undergoing allylic rearrangement, with the hydroxyl group undergoing migration. During the aging and curing processes, cembranoids can easily add oxygen atoms to the carbon–carbon double bonds, whereas the hydroxyl group in the structure may form epoxides, oxidize into ketones, or undergo dehydration reactions. Additionally, the microwave plasma torch interfaced with an MS was used to create and detect the pyrolysis and oxidized products of cembranoids. More degradation products were discovered, including oxidation products with the addition of one to three oxygen atoms, as well as a series of aromatic compounds such as 1,3,5-heptatriene and its range of homologs. This research presented the different degradation pathways of cembranoids in flue-cured tobacco during aging and curing processes, offering valuable insights for the enhancement of tobacco production techniques and quality control.

类樟脑是在烤烟叶片中发现的重要风味前体。降解产物可作为重要的芳香族化合物。本研究利用液相色谱-质谱联用技术在烤烟叶片中发现了16种类膜,其中1种类膜首次从α/β-类膜中分离出氧化脱氢特征。α-和β-类膜被证实是各种降解产物的前体。此外,β-类胶膜在烯丙基重排的同时,也容易向α-类胶膜异构化,羟基发生迁移。在老化和固化过程中,类膜很容易在碳碳双键上加入氧原子,而结构中的羟基可能形成环氧化物,氧化成酮,或发生脱水反应。此外,采用微波等离子体炬与质谱相结合的方法制备并检测了类膜的热解和氧化产物。更多的降解产物被发现,包括添加一到三个氧原子的氧化产物,以及一系列芳香族化合物,如1,3,5-庚三烯及其一系列同系物。本研究揭示了烤烟在陈化和烘烤过程中类膜类物质的不同降解途径,为提高烤烟生产技术和质量控制水平提供有价值的见解。
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来源期刊
Journal of separation science
Journal of separation science 化学-分析化学
CiteScore
6.30
自引率
16.10%
发文量
408
审稿时长
1.8 months
期刊介绍: The Journal of Separation Science (JSS) is the most comprehensive source in separation science, since it covers all areas of chromatographic and electrophoretic separation methods in theory and practice, both in the analytical and in the preparative mode, solid phase extraction, sample preparation, and related techniques. Manuscripts on methodological or instrumental developments, including detection aspects, in particular mass spectrometry, as well as on innovative applications will also be published. Manuscripts on hyphenation, automation, and miniaturization are particularly welcome. Pre- and post-separation facets of a total analysis may be covered as well as the underlying logic of the development or application of a method.
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