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

Bo-Lin Qiu1, Ling-Yan Wang1, Gui-Yang Xia1

  • 1State 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.

Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica
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Summary

Dihydrochelerythrine, isolated from Corydalis yanhusuo, is unstable and converts to chelerythrine in polar solvents. In non-polar solvents, it forms pseudobase, chelerythrine, and oxychelerythrine, impacting its use in medicinal materials.

Keywords:
benzo [c] phenanthridine alkaloidsdihydrochelerythrinesolvent effectstructural conversion

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Pharmacognosy

Background:

  • Dihydrochelerythrine is a compound found in Corydalis yanhusuo.
  • Its stability and chemical behavior in different solvents were previously uncharacterized.

Purpose of the Study:

  • To investigate the stability and structural conversion of dihydrochelerythrine.
  • To understand the influence of solvent polarity on dihydrochelerythrine's chemical transformations.

Main Methods:

  • Isolation of dihydrochelerythrine using chromatography and recrystallization.
  • Monitoring structural conversion using Nuclear Magnetic Resonance (NMR), High-Performance Liquid Chromatography (HPLC), and Liquid Chromatography-Mass Spectrometry (LC-MS).

Main Results:

  • Dihydrochelerythrine is unstable and converts to chelerythrine in polar deuterated solvents (DMSO-d₆, MeOD).
  • In non-polar solvents (CD₂Cl₂), dihydrochelerythrine forms pseudobase, chelerythrine, bimolecular ether, and subsequently oxychelerythrine.
  • The C-6 position of dihydrochelerythrine exhibits high reactivity to nucleophiles, leading to solvent-dependent derivative formation.

Conclusions:

  • Dihydrochelerythrine's instability and solvent-dependent reactivity necessitate careful handling during extraction, isolation, and bioactivity screening.
  • Understanding these transformations is crucial for accurate quality evaluation of medicinal materials containing dihydrochelerythrine and related compounds.