Identification of 4′-Demethyl-3,9-dihydroeucomin as a Bitter-Masking Compound from the Resin of Daemonorops draco,Journal of Agricultural and Food Chemistry

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Identification of 4′-Demethyl-3,9-dihydroeucomin as a Bitter-Masking Compound from the Resin of Daemonorops draco
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-15 , DOI: 10.1021/acs.jafc.4c04583
Sonja Sterneder _{1,

2,

3} , Joachim Seitz ₁ , Johannes Kiefl ₄ , Eric Rottmann ₄ , Margit Liebig ₄ , Maria Blings ₄ , Stephan Seilwind ₄ , Yijun Zhou ₅ , Jianbing Wei ₅ , Haifeng Guan ₅ , Qianjin Zhu ₅ , Johanna Kreißl ₃ , Kai Lamottke _{5,

6} , Jakob P. Ley ₄ , Veronika Somoza _{1,

3,

7}

Affiliation

Masking the bitter taste of foods is one of the key strategies to improve their taste and palatability, particularly in the context of clean labeling, where natural compounds are preferred. Despite the demand, the availability of natural bitter-masking compounds remains limited. Here, we identified the bitter-masking compound 4′-demethyl-3,9-dihydroeucomin (DMDHE) isolated from the resin of Daemonorops draco by means of an activity-guided in vivo (sensory bitterness rating of quinine) and in vitro (cell-based bitter response assays) approach. First, a mean bitter-masking effect of −29.6 ± 6.30% on the bitterness perceived from quinine [10 ppm] was demonstrated for an organic solvent extract of the resin of D. draco (= DD [500 ppm]) in a sensory trial. The results were verified in a cell-based bitter assay in which the bitter taste receptor (TAS2R)-dependent proton secretion serves as an outcome measure of the cellular bitter response in parietal HGT-1 cells. By means of preparative RP-18 high-performance liquid chromatography (HPLC) analysis combined with activity-guided sensory evaluations, the most potent bitter-masking fractions were identified. Subsequent quantitative liquid chromatography/high-resolution mass spectrometry/charged aerosol detection/ultraviolet (LC-HRMS/CAD/UV), NMR analysis, followed by gram-scale synthesis, led to the characterization of DMDHE as bitter-masking homoisoflavanone. DMDHE decreased the sensory bitterness of quinine by 14.8 ± 5.00%. Functional involvement of TAS2R14 was demonstrated by means of a CRISPR-Cas9 approach, which revealed a reduction of the DMDHE-evoked bitter-masking effect by 40.4 ± 9.32% in HGT-1 TAS2R14ko versus HGT-1 wt cells.

中文翻译：

从 Daemonorops draco 树脂中鉴定 4′-Demethyl-3,9-dihydroeucomin 作为苦味掩蔽化合物

掩盖食品的苦味是改善食品味道和适口性的关键策略之一，尤其是在首选天然化合物的清洁标签的情况下。尽管需求旺盛，但天然苦味掩盖化合物的供应仍然有限。在这里，我们通过活性引导的体内（奎宁的感觉苦味等级）和体外（基于细胞的苦味反应测定）方法鉴定了从 Daemonorops draco 树脂中分离的苦掩化合物 4'-脱甲基-3,9-二氢真科明（DMDHE）。首先，在感官试验中，对 D. draco 树脂的有机溶剂提取物（= DD [500 ppm]）的苦味 [10 ppm] 的平均苦味掩盖作用为 -29.6 ± 6.30%。结果在基于细胞的苦味测定中得到验证，其中苦味受体（TAS2R）依赖性质子分泌作为壁层 HGT-1 细胞苦味反应的结果测量。通过制备型 RP-18 高效液相色谱（HPLC）分析结合活性引导的感官评估，确定了最有效的苦味掩盖组分。随后的定量液相色谱/高分辨率质谱/电雾式检测/紫外线（LC-HRMS/CAD/UV）、NMR 分析，然后是克级合成，导致 DMDHE 被表征为苦掩高异黄烷酮。DMDHE 使奎宁的感觉苦味降低了 14.8 ± 5.00%。通过 CRISPR-Cas9 方法证明了 TAS2R14 的功能参与，该方法显示与 HGT-1 wt 细胞相比，HGT-1 TAS2R14ko 中 DMDHE 诱发的苦掩作用降低了 40.4 ± 9.32%。

更新日期：2024-09-15

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