Fluorescence, Absorption, Chromatography and Structural Transformation of Chelerythrine and Ethoxychelerythrine in Protic Solvents: A Comparative Study

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 15; p. 4693
• Main Authors: Cao, Jinjin, Zheng, Yanhui, Liu, Ting, Liu, Jiamiao, Liu, Jinze, Wang, Jing, Sun, Qirui, Li, Wenhong, Wei, Yongju
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 22.07.2022; MDPI
• Subjects: absorbance; Absorption; Absorption spectra; Acids; Aqueous solutions; Chelerythrine; Chromatography; Comparative studies; Drug testing; Emission spectra; Ethanol; ethoxychelerythrine; Fluorescence; Herbal medicine; High performance liquid chromatography; Liquid chromatography; Molecular weight; Quality control; Solvents; Spectral emittance; Spectrum analysis; structural transformation; United States > US; Japan
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27154693

Chelerythrine (CH) and ethoxychelerythrine (ECH) are chemical reference substances for quality control of Chinese herbal medicines, and ECH is the dihydrogen derivative of CH. In this study, their fluorescence and absorption spectra, as well as their structural changes in different protic solvents were compared. It was observed that their emission fluorescence spectra in methanol were almost the same (both emitted at 400 nm), which may be attributed to the nucleophilic and exchange reactions of CH and ECH with methanol molecules with the common product of 6-methoxy-5,6-dihydrochelerythrine (MCH). When diluted with water, MCH was converted into CH, which mainly existed in the form of positively charged CH+ under acidic and near-neutral conditions with the fluorescence emission at 550 nm. With the increase of pH value of the aqueous solution, CH+ converted to 6-hydroxy-5,6-dihydrochelerythrine (CHOH) with the fluorescence emission at 410 nm. The fluorescence quantum yields of MCH and CHOH were 0.13 and 0.15, respectively, and both the fluorescence intensities were much stronger than that of CH+. It is concluded that CH and ECH can substitute each other in the same protic solvent, which was further verified by high-performance liquid chromatography. This study will help in the investigation of structural changes of benzophenanthridine alkaloids and will provide the possibility for the mutual substitution of standard substances in relevant drug testing.