Biothermodynamics, TUM School of Life and Food Sciences Weihenstephan, Technical University of Munich, 85354 Freising, Germany.
Biothermodynamics, TUM School of Life and Food Sciences Weihenstephan, Technical University of Munich, 85354 Freising, Germany.
Food Res Int. 2021 Mar;141:110123. doi: 10.1016/j.foodres.2021.110123. Epub 2021 Jan 11.
The plant genus Piper comprises extensively consumed spice taxa like black pepper (P. nigrum L.) or long pepper (P. longum L.). The chronic dietary use of different Piper spices has been associated with different health benefits, though the molecular mechanisms remain poorly understood. The aim of this work was to perform the liquid-chromatography-high-resolution tandem mass spectrometry (LC-HRMS/MS) profiling and LC-DAD quantification of piperamides in several Piper species and varieties and study their ability to modulate the endocannabinoid system (ECS). LC-HRMS/MS analysis revealed a number of 42 piperamides grouped into six structural classes, with 22 of them, notably piperine, retrofractamide B, guineensine, piperchabamide C, being also quantified by LC-DAD. The multivariate analysis showed that P. nigrum and P. longum are very similar with respect to their piperamide profile, while the other Piper spices (P. retrofractum, P. guineense, P. cubeba, P. borbonense) might have significantly different metabolite patterns. The results from the biological assays confirmed that guineensine and total piperamides are strongly correlated with anandamide (AEA) cellular uptake inhibition. While none of the Piper spice extracts showed binding activity at cannabinoid CB receptors, some P. nigrum varieties exhibited moderate binding interactions with CB receptors. Overall, the analytical profiling enabled global annotations of piperamides associated to cannabimimetic effects in Piper spices.
胡椒属植物包括广泛食用的香料类群，如黑胡椒（Piper nigrum L.）或荜澄茄（Piper longum L.）。不同胡椒香料的慢性饮食使用与不同的健康益处有关，但分子机制仍知之甚少。本工作的目的是对几种胡椒属植物和品种中的胡椒酰胺进行液相色谱-高分辨串联质谱（LC-HRMS/MS）分析和 LC-DAD 定量，并研究其对内源性大麻素系统（ECS）的调节能力。LC-HRMS/MS 分析显示了 42 种胡椒酰胺，分为 6 个结构类别，其中 22 种，特别是胡椒碱、反式胡椒酰胺 B、几内亚酰胺、胡椒查巴酰胺 C，也通过 LC-DAD 进行了定量。多变量分析表明，黑胡椒和荜澄茄在其胡椒酰胺谱方面非常相似，而其他胡椒香料（P. retrofractum、P. guineense、P. cubeba、P. borbonense）可能具有明显不同的代谢模式。生物测定结果证实，几内亚酰胺和总胡椒酰胺与花生四烯酸乙醇胺（AEA）细胞摄取抑制强烈相关。虽然没有一种胡椒香料提取物显示出与大麻素 CB 受体的结合活性，但一些黑胡椒品种与 CB 受体表现出中等的结合相互作用。总体而言，分析谱能够对胡椒香料中与大麻样作用相关的胡椒酰胺进行全面注释。
