Degradation and transformation mechanisms of numbing substances: Hydroxyl-α-sanshool & hydroxyl-β-sanshool from Zanthoxylum bungeanum exposed to acid environment
Luo, Jingjing | Hou, Xiaoyan | Li, Shanshan | Luo, Qingying | Wu, Hejun | Shen, Guanghui | Gu, Xuequan | Mo, Xiaoyan | Zhang, Zhiqing
In present work, Zanthoxylum bungeanum meal (ZBM) used as experimental material, the stability of typical alkylamides (hydroxyl-α-sanshool and hydroxyl-β-sanshool) in ZBM under different acidification conditions was investigated, in order to reveal degradation or transformation mechanism of numbing substances from Z. bungeanum exposed to acid environment and its transform direction. The alkylamides content of ZBM was detected by using HPLC after different conditions of acidification. The results indicated that hydroxyl-α-sanshool and hydroxyl-β-sanshool under the concentration of hydrochloric acid is 14% decreased by 80% after only 0.5 h. Moreover, some of the components undergo isomerization and addition reactions in the process of acidification, the products of isomerization are hydroxyl-ε-sanshool and (1Z,2E,4E,8E,10E)-N-(2-hydroxy-2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid; and the product of the addition reaction is (2E,6E,8E,10E)-1-chloro-1-(2-hydroxy-2-methylpropyl)amino)dodeca-2,6,8,10-tetraen-1-ol, which indicated that acid environment has greatly changed the numbing substances in Z. bungeanum and its products.
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