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Zhongguo Zhong Yao Za Zhi. 2018 Aug;43(16):3315-3321. doi: 10.19540/j.cnki.cjcmm.20180511.002.

[Study on structural conversion of dihydrochelerythrine in different solvents].

[Article in Chinese]

Author information

1
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
2
College of Pharmaceutical Sciences, Qinghai University for Nationalities, Xining 810007, China.

Abstract

Dihydrochelerythrine was isolated from the ethanol extract of Corydalis yanhusuo by chromatographic and recrystallization techniques. To our knowledge, this is the first report that dihydrochelerythrine was found to be unstable. The NMR, HPLC, and LC-MS were applied to monitor the structural conversion process of dihydrochelerythrine. The results showed that when dissolved in polar deuteration solvent (e.g., DMSO-d₆ & MeOD), dihydrochelerythrine is directly converted to chelerythrine gradually. However, if used non-polar reagent (e.g.,CD₂Cl₂), the sample of dihydrochelerythrine undergoes the formation of pseudobase, chelerythrine, and bimolecular ether then followed by oxidation to oxychelerythrine as the major final product. Which leads to this phenomenon maybe is that the C-6 in dihydrochelerythrine is highly reactive to nucleophiles, and is easily converted to different derivatives in different solvents attributed to the solvent effect. This finding will contribute to the extraction and isolation, bioactivity screening, and quality evaluation of medicinal materials containing dihydrochelerythrine and other similar derivatives.

KEYWORDS:

benzo [c] phenanthridine alkaloids ; dihydrochelerythrine ; solvent effect ; structural conversion

Conflict of interest statement

The authors of this article and the planning committee members and staff have no relevant financial relationships with commercial interests to disclose.

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