Department of Analytical Chemistry, University of Cádiz, Avda. República Saharaui, s/n, Puerto Real, Cádiz, Spain.
J Agric Food Chem. 2010 Mar 24;58(6):3342-9. doi: 10.1021/jf9035029.
We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestivum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.
我们描述了两种化合物家族——辣椒素类化合物和辣椒素类似物的合成方法，这是对结构与活性之间定量关系研究的一部分。我们总共合成了 14 种侧链长度不断增加的辣椒素类化合物，从 2 个碳原子到 16 个碳原子。此外，我们还合成了具有相同侧链的 14 种辣椒素类似物，以及辣椒碱和二氢辣椒碱，并开发了一种合成这些化合物的新方法。产率范围为 48.35%至 98.98%。研究发现，合成的辣椒素类化合物和辣椒素类似物表现出与天然化合物相似的亲脂性，并表现出相似的生物活性。与天然化合物相比，合成的辣椒素类化合物和辣椒素类似物的生物活性按亲脂性（更高或更低）的差异程度成比例降低。生物活性通过对黄化小麦（Triticum aestivum L.）胚芽鞘生物测定法和通过比较合成结果与天然对应化合物的结果来确定。发现的生物活性与合成化合物的亲脂性特性直接相关。
