School of Food and Nutritional Sciences and Global COE Program, University of Shizuoka, Suruga-ku, Shizuoka, Japan.
J Agric Food Chem. 2010 Mar 24;58(6):3627-31. doi: 10.1021/jf904280z.
N-Vanillyl-acylamides (NVAs) naturally occur as capsaicinoids in Capsicum plants. NVAs with a longer chain acyl moiety (LCNVAs) have been developed as attractive tools for medicinal usage because of their capsaicin-like bioactive and physiological properties, without harmful irritancy. In this study, we isolated four LCNVAs from Capsicum oleoresin. Their structures were determined to be N-vanillyl-hexadecanamide (palvanil, 2), N-vanillyl-octadecanamide (stevanil, 3), N-vanillyl-9E-octadecenamide (olvanil, 4), and N-vanillyl-9E,12E-octadecadienamide (livanil, 5) by spectroscopic analysis and gas chromatography-mass spectrometry analysis of their methanolysis products. Furthermore, the existence of two LCNVAs in oleoresin, N-vanillyl-tetradecanamide (myrvanil, 1) and N-vanillyl-9E,12E,15E-octadecatrienamide (linvanil, 6), was suggested. The contents of these LCNVAs and the major capsaicinoids-capsaicin and dihydrocapsaicin-in three Capsicum oleoresins and the fresh fruits of two hot peppers were measured by a liquid chromatography-tandem mass spectrometry system. The content ratios of the total LCNVAs, except for myrvanil, versus the capsaicin in the oleoresins (0.1-41%) was significantly larger than that in fresh fruits (<0.01%). The composition of these LCNVAs in each oleoresin was similar to that of fatty acids in the oil fraction of each oleoresin. We observed no relationship between the composition of these LCNVAs in the fresh fruits.
N-香草基酰基酰胺（NVAs）天然存在于辣椒植物中的辣椒素类化合物中。由于其具有类似辣椒素的生物活性和生理特性，而没有有害的刺激性，因此具有更长链酰基部分的 NVAs（LCNVAs）已被开发为有吸引力的药用工具。在这项研究中，我们从辣椒树脂中分离出四种 LCNVAs。通过对它们的甲醇解产物进行光谱分析和气相色谱-质谱分析，确定它们的结构分别为 N-香草基十六酰胺（palvanil，2）、N-香草基十八酰胺（stevanil，3）、N-香草基-9E-十八烯酰胺（olvanil，4）和 N-香草基-9E，12E-十八二烯酰胺（livanil，5）。此外，还表明树脂中存在两种 LCNVAs，即 N-香草基十四酰胺（myrvanil，1）和 N-香草基-9E，12E，15E-十八三烯酰胺（linvanil，6）。通过液相色谱-串联质谱系统测定了三种辣椒树脂和两种辣椒新鲜果实中的这些 LCNVAs 以及主要辣椒素-辣椒素和二氢辣椒素的含量。除 myrvanil 外，这些 LCNVAs 的总量与树脂中辣椒素的含量比（0.1-41%）明显大于新鲜果实中的含量比（<0.01%）。每种树脂中这些 LCNVAs 的组成与每种树脂中油部分的脂肪酸组成相似。我们没有观察到新鲜果实中这些 LCNVAs 组成之间的关系。
