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首页> 外文期刊>Journal of Agricultural and Food Chemistry >The Odorant (R)-Citronellal Attenuates Caffeine Bitterness by Inhibiting the Bitter Receptors TAS2R43 and TAS2R46
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The Odorant (R)-Citronellal Attenuates Caffeine Bitterness by Inhibiting the Bitter Receptors TAS2R43 and TAS2R46

机译：通过抑制苦受体TAS2R43和TAS2R46，气味（R）-Citrogellal衰减咖啡因苦味

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摘要

Sensory studies showed the volatile fraction of lemon grass and its main constituent, the odor-active citronellal, to significantly decrease the perceived bitterness of a black tea infusion as well as caffeine solutions. Seven citronellal-related derivatives were synthesized and shown to inhibit the perceived bitterness of caffeine in a structure-dependent manner. The aldehyde function at carbon 1, the (R)-configuration of the methyl-branched carbon 3, and a hydrophobic carbon chain were found to favor the bitter inhibitory activity of citronellal; for example, even low concentrations of 25 ppm were observed to reduce bitterness perception of caffeine solution (6 mmol/L) by 32%, whereas (R)-citronellic acid (100 pm) showed a reduction of only 21% and (R)-citronellol (100 pm) was completely inactive. Cell-based functional experiments, conducted with the human bitter taste receptors TAS2R7, TAS2R10, TAS2R14, TAS2R43, and TAS2R46 reported to be sensitive to caffeine, revealed (R)citronellal to completely block caffeine-induced calcium signals in TAS2R43-expressing cells, and, to a lesser extent, in TAS2R46-expressing cells. Stimulation of TAS2R43-expressing cells with structurally different bitter agonists identified (R)-citronellal as a general allosteric inhibitor of TAS2R43. Further structure/activity studies indicated 3-methyl-branched aliphatic aldehydes with a carbon chain of = 4 C atoms as best TAS2R43 antagonists. Whereas odor taste interactions have been mainly interpreted in the literature to be caused by a central neuronal integration of odors and tastes, rather than by peripheral events at the level of reception, the findings of this study open up a new dimension regarding the interaction of the two chemical senses.
机译：感官研究表明，柠檬草和它的主要成分，气味活性香茅醛的挥发性组分，以显著降低红茶输液的感知苦味和咖啡因的解决方案。七香茅醛相关衍生物的合成和显示出抑制咖啡因的苦味感知的结构依赖性。在碳1所述的醛官能团，所述（R）被发现的甲基支链的碳3和疏水碳链的构型以有利于香茅醛的苦味抑制活性;例如，观察到25ppm的的甚至低浓度的32％，以减少的咖啡因溶液（6毫摩尔/ L）苦味感觉，而（R）-citronellic酸（100微米）显示只减少21％和（R）香茅醇（100点）为完全失活。基于细胞的功能试验中，与人苦味味觉感受器TAS2R7，TAS2R10，TAS2R14，TAS2R43和TAS2R46进行报道为咖啡因敏感，表明（R）香茅醛完全阻断在TAS2R43表达细胞咖啡因诱导的钙信号，并且，在较小程度上，在TAS2R46表达细胞。的TAS2R43表达细胞与香茅醛作为TAS2R43的一般变构抑制剂鉴定结构上不同的苦味受体激动剂（R）刺激。进一步结构/活性研究表明3-甲基支链的脂族醛与＆ 0的碳链; = 4个碳原子的作为最佳TAS2R43拮抗剂。而气味味道相互作用进行了主要解释在文献中被气味和味道的中枢神经元的整合造成的，而不是在接待水平外围事件，这项研究的发现开辟了一个新的层面有关的相互作用两种化学感官。

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