NMR-Based Studies on Odorant–Melanoidin Interactions in Coffee Beverages,Journal of Agricultural and Food Chemistry

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NMR-Based Studies on Odorant–Melanoidin Interactions in Coffee Beverages
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2021-12-07 , DOI: 10.1021/acs.jafc.1c06163
Michael Gigl ₁ , Thomas Hofmann ₁ , Oliver Frank ₁

Affiliation

A quantitative ¹H NMR-based approach was established, which allowed the direct and noninvasive analysis of molecular interactions between key coffee odorants and high-molecular-weight (HMW) melanoidin polymers. A clear distinction between covalent and noncovalent interactions was achieved by monitoring the time dependency of odorant–polymer interactions, resulting in four scenarios: covalent, π–π, covalent and π–π–, as well as no interactions. Evaluation of temperature influence on e.g. 2-furfurylthiol (FFT), revealed an altered behavior with increased π–π stacking at lower temperatures and accelerated covalent interactions at higher temperatures. Human sensory experiments with HMW material and a coffee aroma reconstitution model showed a drastic reduction of “roasty/sulfury” aroma notes, as well as an increased “sweetish/caramel-like” flavor. The lack of interactions between the “sweetish/caramel” smelling 4-hydroxy-2,5-dimethyl-3(2H)-furanone with the HMW melanoidins in combination with the high binding affinity of coffee thiols explains the sensory evaluation and is obviously the reason for the fast disappearance of the typical “roasty/sulfury” aroma impressions of a freshly prepared coffee brew.

中文翻译：

基于核磁共振的咖啡饮料中气味-类黑素相互作用的研究

一个数量¹建立了基于 H NMR 的方法，它允许对关键咖啡气味剂和高分子量 (HMW) 类黑素聚合物之间的分子相互作用进行直接和非侵入性分析。通过监测气味-聚合物相互作用的时间依赖性，明确区分了共价和非共价相互作用，产生了四种情况：共价、π-π、共价和 π-π-，以及无相互作用。评估温度对例如 2-糠基硫醇 (FFT) 的影响，揭示了在较低温度下增加 π-π 堆积和在较高温度下加速共价相互作用的行为改变。使用 HMW 材料和咖啡香气重构模型进行的人体感官实验表明，“烘焙/硫磺”香气明显减少，“甜味/焦糖样”风味增加。H )-呋喃酮与 HMW 类黑素结合咖啡硫醇的高结合亲和力解释了感官评价，并且显然是新鲜制备的咖啡冲泡典型的“烘焙/硫磺”香气印象迅速消失的原因。

更新日期：2021-12-22

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