Degradation and Transformation Mechanisms of Zanthoxylum Alkylamides Exposed to UVB Light

Abstract

Zanthoxylum oleoresin, a concentrated extract derived from Zanthoxylum bungeanum, is rich in non-volatile, intensely flavorful substances and amide compounds, such as hydroxy-α-sanshool, hydroxy-β-sanshool, and hydroxy-ε-sanshool. The production process of Zanthoxylum oleoresin remains unstandardized, and there is still a lack of research on the precise classification and quantification of its key chemical constituents, as well as the stability of these compounds when produced using different extraction methods. This study utilized preparative liquid chromatography to extract and purify amide compounds from Zanthoxylum oleoresin, successfully isolating three sanshools: hydroxy-α-sanshool, hydroxy-β-sanshool, and hydroxy-ε-sanshool. The stability of three these sanshools under UVB irradiation in different solvents was explored in UVB-simulated sunlight conditions to investigate the degradation or transformation mechanism of Zanthoxylum alkylamides under UVB irradiation. The findings indicate a rapid decrease in the hydroxy-α-sanshool content under UVB ultraviolet light, aligning with the second-order kinetics. This study revealed alterations in the contents of hydroxy-α-sanshool, hydroxy-β-sanshool, and hydroxy-ε-sanshool and the formation of a new compound following exposure to UVB light. This new compound, along with the three sanshools, possesses a uniform m/z 264 and shares similar chemical structures. Further analysis also uncovered that these compounds are capable of undergoing isomerization reactions under UVB irradiation. This demonstrates that UVB irradiation of certain intensities can modify the concentrations and chemical structures of these Zanthoxylum alkylamides. These insights offer crucial guidance for future studies on the processing and preservation of Zanthoxylum alkylamides and their derivatives.